Explore every episode of the podcast Business Insights

How to Cut Business Technology Costs and Avoid Costly IT Mistakes | Blake Patterson

Blake Patterson, founder and president of Exploring IT Solutions, joins Seth Krussman on the Business Insights podcast to share insights from more than a decade working with major technology and telecommunications providers, including Comcast, Verizon, and T-Mobile.

From hidden IT expenses and restrictive vendor contracts to cybersecurity, AI, and technology planning, Blake explains how business owners can make smarter technology decisions, reduce unnecessary costs, and avoid common purchasing mistakes. Discover why comparing providers, standardizing technology across locations, and working with an independent technology advisor can help businesses improve efficiency, strengthen operations, and plan for growth.

Key Takeaways:

• Hidden Technology Costs: How vendor incentives, bundled services, and contract renewals can lead businesses to overpay for technology they don't need.
• Smarter IT Purchasing: Why comparing multiple providers and creating competition can uncover better solutions, pricing, and contract terms.
• Technology Standardization: How inconsistent IT decisions across departments and locations create unnecessary expenses and operational complexity.
• Cybersecurity and AI: Why businesses need proactive security support and should implement AI based on practical needs without losing the human touch.
• The Value of Independent IT Advice: How an experienced technology advisor can help businesses navigate vendors, coordinate projects, and make better long-term technology decisions.

Connect with Blake:

Website:https://exploringitsolutions.com/

LinkedIn: https://www.linkedin.com/in/joshuablake18

Pathfinders: https://exploringitsolutions.com/pathfinders/

With your guest host Seth Krussman:

Seth Krussman is a seasoned financial advisor and partner at Brayshaw Financial Group, LLC, with over 30 years of experience in entrepreneurship, business development, and wealth management. A Registered Representative and Investment Advisor Representative with Osaic Wealth, Inc., Seth specializes in tax-efficient investment strategies, executive compensation, and succession planning for high-net-worth clients. Based in Hillsboro, Oregon, he is also the nationally recognized co-host of the radio show Money On Tap and an active community leader, husband, and father.

seth@brayshawfinancial.com

brayshawfinancial.com

Mike Milligan is the founder of OneOak Financial, an author, financial strategist, and entrepreneur who has built an Inc. 5000 company with a 30-plus-person team serving clients across the United States. His approach to financial planning emphasizes tax strategy alongside investments and retirement planning.

In this episode, Mike shares how his early experiences with money shaped his career, why taxes can be one of the biggest expenses in retirement, and how better planning can help individuals and business owners keep more of what they earn. He also explores advisor fees, Roth conversions, required minimum distributions, business growth, and the importance of having a financial plan clients can actually understand. 

Key Takeaways:

● Make Tax Strategy Part of Retirement Planning: Proactive tax planning can help retirees and business owners identify opportunities to reduce their long-term tax burden.

● Look Beyond Investment Returns: A comprehensive financial plan should address taxes, retirement goals, cash flow, and other financial decisions—not just portfolio performance.

● Understand What You’re Paying For: Knowing how financial firms and advisors earn money can help investors better evaluate the fees and value of the services they receive.

● Turn Your Financial Plan Into a Roadmap: A clearly documented plan can make financial decisions easier to understand and help clients become more informed about their own finances.

● Growth Creates New Business Challenges: As a company expands, overcoming obscurity and maintaining the founder’s original vision become increasingly important leadership priorities.

Connect with Mike:

Website: www.mikemilligan.com

LinkedIn: www.linkedin.com/in/mikemilligancfp

Book: www.amazon.com/author/oneofakind

Estate planning is about more than documents—it’s about making sure your assets, advisors, and intentions actually work together.

Chris Carns is a board-certified estate planning and probate attorney and partner at Hessie, Blythe & Carns in Plano, Texas, with roughly 15 years of experience serving families, business owners, and high-net-worth clients. In this episode, Chris breaks down common estate planning mistakes, planning considerations for blended families and business owners, and why coordination among attorneys, CPAs, and financial advisors becomes increasingly important as wealth grows.

Key Takeaways:

● Coordinate the Plan and the Assets: Estate planning documents alone aren’t enough; account ownership, beneficiary designations, insurance, IRAs, and other assets need to align with the overall plan.

● Planning Is an Ongoing Process: Changes in family relationships, assets, businesses, and laws can make an outdated estate plan less effective.

● Prepare for Complex Family Dynamics: Blended families, remarriage, children, and grandchildren can require carefully designed trusts and distribution strategies.

● Build a Collaborative Advisory Team: Attorneys, CPAs, and financial advisors can better serve high-net-worth families when recommendations are coordinated rather than made in isolation.

● Plan for the Business Before the Exit: Business owners can benefit from addressing succession, legal documents, deal structure, and tax considerations well before signing a letter of intent or selling the company.

Connect with Chris:

LinkedIn: https://www.linkedin.com/in/christopher-carns-b0aab22a

With your Guest Host Dana Gibson:

Dana Gibson is a Retirement Diagnostician and Certified Financial Fiduciary known as The Roth Doctor™. His approach was shaped by a life-changing 1995 assault and subsequent financial devastation, which taught him how quickly health, wealth, and financial security can change.

Today, Dana helps pre-retirees identify hidden risks involving taxes, RMDs, Social Security, retirement income, longevity, and wealth preservation. He also developed the Self-Completing Roth Conversion Strategy to help families reduce lifetime retirement taxes.

Dana’s philosophy is simple: every retirement deserves a thorough diagnosis before a financial prescription.

Website:  https://taxmitigation.net/tax-readiness-score.html

Joshua Kreitzman, CPA and owner of Kreitzman & Company, brings more than 20 years of experience spanning financial management, nonprofit leadership, entertainment production, and business advisory work. His firm serves hundreds of businesses and individuals, with particular experience working with contractors, construction companies, and family-owned businesses.

In this episode, Joshua joins guest host Peter Florio to discuss his unconventional journey from theater to accounting and how skills like active listening, communication, and collaboration shape his approach to advising business owners. They also explore the changing accounting profession, the impact of AI and virtual work, and why strong professional relationships go far beyond preparing tax returns.

Key Takeaways:

● Listening Is a Business Skill: Joshua explains how his theater background taught him to listen closely, understand what clients really need, and communicate financial information more effectively.

● Keep Financial Decisions Simple: Breaking complex financial concepts into understandable terms helps business owners make more informed decisions and avoid unnecessary confusion.

● Collaboration Creates Better Outcomes: Accountants, financial advisors, insurance professionals, and other specialists can provide greater value when they work together around the client.

● Technology Is Changing Accounting: Virtual meetings, cloud-based tools, and AI are helping smaller accounting firms become more efficient and access sophisticated research capabilities.

● Great Advisors Go Beyond Transactions: Building trust, understanding a client's goals, and supporting long-term growth can turn an accountant into a true business advisor.

Connect with Josh:

Website: www.kreitzmancpas.com

With Guest Host Peter Florio:

Peter F. Florio, CFP, CLU, ChFC, CExP, CLTC is a well-respected financial educator, author, speaker and wealth, tax and financial planner. For nearly 40 years, his advice and expertise have been sought out by high net worth individuals and small business owners to manage their wealth and protect their families and businesses from life’s unforeseen pratfalls. 

Peter regularly shares his knowledge of innovative ideas and concepts with CPA’s and attorneys. He serves the needs of over 500 clients located throughout the country with a concentration in the Long Island/New York City area.  

Peter is the Founder and Managing Partner of The Florio Wealth Management Group, a financial planning and wealth management firm located in Westbury, NY. He is a lifelong resident of Baldwin, New York, a member of the Kiwanis Club of Baldwin and an active supporter of the Long Island Cystic Fibrosis Foundation.  

Website: https://www.floriowmg.com

LinkedIn: https://www.linkedin.com/company/florio-wealth-management-group/

Facebook: https://www.facebook.com/floriowmg

Calendly: https://calendly.com/floriowmg

Marcelino Dodge is an Enrolled Agent, Certified Tax Representation Consultant, and founder of Cash Tracks Financial and Panther Tax Resolution, helping individuals and business owners resolve tax problems and plan more effectively.

In this episode, Marcelino breaks down common tax mistakes, from choosing the wrong business structure and relying on questionable tax advice to mishandling retirement withdrawals and waiting too long to address IRS problems. He also explains how tax resolution works, why planning ahead matters, and how tax and investment professionals can work together to help clients make better-informed financial decisions.

Key Takeaways:

● Choose the Right Business Structure: The wrong entity or tax election can lead business owners to pay more in taxes than necessary.

● Plan Before Major Financial Moves: Retirement withdrawals, business decisions, and other significant transactions can create unexpected tax consequences without advance planning.

● Understand Tax Resolution: Offers in compromise, installment agreements, and other IRS solutions have specific qualification requirements and are not automatic.

● Stay Current With the IRS: Filing required tax returns and maintaining compliance can be critical when trying to resolve an existing tax problem.

● Coordinate Financial and Tax Planning: Collaboration between tax and investment professionals can help clients anticipate tax consequences and

Connect with Marcelino:

Website: www.taxreliefcall.com

Website: www.cashtracksfinancial.com

Calendly: Select a Date & Time - Calendly

Facebook: https://www.facebook.com/CashTracksCOS/

YouTube: https://youtube.com/channel/UC9HIcpd8lTskcc2lwlGPZMA

With your Guest Host Dana Gibson:

Dana Gibson is a Retirement Diagnostician and Certified Financial Fiduciary known as The Roth Doctor™. His approach was shaped by a life-changing 1995 assault and subsequent financial devastation, which taught him how quickly health, wealth, and financial security can change.

Today, Dana helps pre-retirees identify hidden risks involving taxes, RMDs, Social Security, retirement income, longevity, and wealth preservation. He also developed the Self-Completing Roth Conversion Strategy to help families reduce lifetime retirement taxes.

Dana’s philosophy is simple: every retirement deserves a thorough diagnosis before a financial prescription.

Website: https://taxmitigation.net/tax-readiness-score.html

Jason Wiggam is the founding partner of Wiggam Law, an Atlanta-based tax controversy firm representing individuals, business owners, executives, and investors in disputes with the IRS and state tax authorities. His firm serves clients nationwide and has grown from a two-person operation to a team of 50.

In this episode, Jason explains what business owners should know when facing IRS audits, tax debt, collection notices, and settlement options. He breaks down common misconceptions about the IRS, why ignoring notices can be costly, how offers in compromise really work, and why taxpayers should understand their options before making decisions based on fear.

Key Takeaways:

● Respond to IRS Notices Quickly: Ignoring an IRS letter can cause taxpayers to miss important deadlines and lose valuable rights.

● Understand Your Settlement Options: Offers in compromise, penalty abatements, collection statutes, and bankruptcy may provide solutions depending on the circumstances.

● Beware of “Pennies on the Dollar” Claims: IRS tax settlements are possible, but aggressive advertising often makes these outcomes appear far more common than they are.

● Get Representation During an Audit: Business owners should consider having an experienced tax professional communicate with the IRS rather than handling an audit themselves.

● File Even If You Can’t Pay: Delaying a tax return because you cannot afford the balance can create additional penalties and make the problem more expensive.

Connect with Jason:

LinkedIn:  https://www.linkedin.com/in/jasonwiggam/

Website:  https://wiggamlaw.com

Armine Alajian is a CPA, entrepreneur, and founder and CEO of the Alajian Group, a full-service accounting and advisory firm serving startups, growing businesses, entrepreneurs, and high-net-worth individuals. With more than 20 years of experience spanning public accounting, corporate finance, fintech, tax strategy, and fractional CFO services, she helps business owners turn financial data into better decisions.

In this episode, Armine joins guest host Peter Florio to explain why accounting should go far beyond preparing tax returns. They discuss the importance of accurate financial reporting, cash flow management, fractional CFO support, AI and automation, and building the financial infrastructure businesses need to grow, raise capital, and prepare for future opportunities.

Key Takeaways:

● Accounting Goes Beyond Taxes: Strong accounting gives business owners the financial information they need to make informed decisions throughout the year.

● Cash Flow Is Critical: Understanding when money actually comes in and goes out helps businesses anticipate needs and avoid costly surprises.

● Financial Infrastructure Supports Growth: Reliable reporting, internal controls, and clean financial data become increasingly important as a company scales.

● Fractional CFOs Fill a Strategic Gap: Growing businesses can access projections, analytics, fundraising support, and higher-level financial guidance without building a full internal finance department.

● AI Is a Tool, Not a Replacement: AI and automation can make accounting more efficient, but professional expertise remains essential for evaluating information and applying it correctly.

Connect with Armine:

Website:  www.alajiangroup.com

With Guest Host Peter Florio:

Peter F. Florio, CFP, CLU, ChFC, CExP, CLTC is a well-respected financial educator, author, speaker and wealth, tax and financial planner. For nearly 40 years, his advice and expertise have been sought out by high net worth individuals and small business owners to manage their wealth and protect their families and businesses from life’s unforeseen pratfalls. 

Peter regularly shares his knowledge of innovative ideas and concepts with CPA’s and attorneys. He serves the needs of over 500 clients located throughout the country with a concentration in the Long Island/New York City area.  

Peter is the Founder and Managing Partner of The Florio Wealth Management Group, a financial planning and wealth management firm located in Westbury, NY. He is a lifelong resident of Baldwin, New York, a member of the Kiwanis Club of Baldwin and an active supporter of the Long Island Cystic Fibrosis Foundation.  

Website: https://www.floriowmg.com

LinkedIn: https://www.linkedin.com/company/florio-wealth-management-group/

Facebook: https://www.facebook.com/floriowmg

Calendly: https://calendly.com/floriowmg

Behavioral economics may be the missing piece in how RIAs price and position their advice.

Etinosa Agbonlahor is a behavioral economist and CEO of Decision Alpha, where she applies behavioral economics to pricing, decision-making, product design, and growth. Her experience includes working with major banks in Australia and a large U.S. investment firm.

In this episode, Etinosa explores why RIAs and business owners often underprice their services, how clients perceive value, and why pricing requires both math and psychology. She also explains how anchoring, pricing options, client segmentation, and positioning can help advisors structure fees more effectively.

Key Takeaways:

● Underpricing Can Undermine Value: RIAs often price based on what feels fair to them rather than what their expertise is worth to clients.

● Pricing Is Both Art and Science: Sustainable pricing requires understanding margins and profitability while accounting for how clients make decisions.

● Give Clients Meaningful Choices: Offering structured pricing options gives prospects reference points and can make decisions easier than presenting one price or too many choices.

● Positioning Shapes Perceived Value: How and where an advisory service is presented can significantly influence what clients believe that service is worth.

● Use Anchoring Strategically: Advisors can establish relevant comparison points that help clients evaluate the value of their advice and pricing.

Connect with Etinosa:

Website: www.etinosaa.com

For businesses in fast-changing industries, the right CPA can be more than a tax preparer—they can become an essential part of the team.

Zachary Gordon, CPA, founder of Red Five Services, brings experience across public accounting, private equity, startups, and highly regulated industries including cannabis and technology. In this episode, Zach shares how proactive planning, clear communication, modern accounting practices, and a true advisory relationship can help business owners navigate complex regulations, manage growth, and make better financial decisions.

Key Takeaways:

● Proactive Planning Matters: Tax and financial decisions are far easier to manage when business owners plan ahead instead of waiting until deadlines or problems arise.

● Communication Builds Better Outcomes: Strong CPA-client relationships depend on consistent communication, realistic expectations, and a willingness to address issues early.

● Regulated Industries Require Specialized Knowledge: Businesses in emerging and highly regulated markets need advisors who understand evolving rules and know how to prepare for additional scrutiny.

● Modern Accounting Goes Beyond Compliance: Business owners can gain more value from CPAs who help evaluate opportunities, solve problems, and support strategic decisions rather than simply prepare forms.

Connect with Zachary:

LinkedIn: https://www.linkedin.com/in/zacharygordon-cpa/

Website: https://redfiveservices.com/

With your Guest Host Peter Florio:

Peter F. Florio, CFP, CLU, ChFC, CExP, CLTC is a well-respected financial educator, author, speaker and wealth, tax and financial planner. For nearly 40 years, his advice and expertise have been sought out by high net worth individuals and small business owners to manage their wealth and protect their families and businesses from life’s unforeseen pratfalls. 

Peter regularly shares his knowledge of innovative ideas and concepts with CPA’s and attorneys. He serves the needs of over 500 clients located throughout the country with a concentration in the Long Island/New York City area.  

Peter is the Founder and Managing Partner of The Florio Wealth Management Group, a financial planning and wealth management firm located in Westbury, NY. He is a lifelong resident of Baldwin, New York, a member of the Kiwanis Club of Baldwin and an active supporter of the Long Island Cystic Fibrosis Foundation.  

Website: https://www.floriowmg.com

LinkedIn: https://www.linkedin.com/company/florio-wealth-management-group/

Facebook: https://www.facebook.com/floriowmg

Calendly: https://calendly.com/floriowmg

California's New SaaS Tax Law Explained

State tax rules can quietly become one of the biggest risks facing growing businesses.

Penny Sweeting is a Senior Tax Manager at Withum specializing in state and local tax (SALT), nexus, and multi-state expansion. She helps businesses identify tax exposure before it becomes an expensive compliance problem, particularly as companies grow across state lines, hire remote employees, or prepare for mergers and acquisitions.

In this episode, Penny explains what tax nexus really means, how economic and physical presence create tax obligations, why California's new SaaS tax rules are a major development, and how proactive planning can reduce risk, uncover savings, and protect business value during growth.

Key Takeaways:

● Physical and economic nexus create different tax obligations that every growing business should understand.

● Remote employees, third-party inventory, and e-commerce expansion can unexpectedly trigger multi-state tax exposure.

● California's new SaaS tax rules make it critical for software companies selling into the state to prepare before 2027.

● M&A due diligence frequently uncovers hidden state tax liabilities that can impact valuation and deal structure.

● Regular nexus reviews help companies avoid costly penalties while identifying potential tax savings and refund opportunities.

Connect with Penny:

Website: https://www.withum.com/service/tax/state-and-local-tax/

Website: https://www.withum.com/state-and-local-tax-updates/

With Your Guest Host Seth Krussman:

Seth Krussman is a seasoned financial advisor and partner at Brayshaw Financial Group, LLC, with over 30 years of experience in entrepreneurship, business development, and wealth management. A Registered Representative and Investment Advisor Representative with Osaic Wealth, Inc., Seth specializes in tax-efficient investment strategies, executive compensation, and succession planning for high-net-worth clients. Based in Hillsboro, Oregon, he is also the nationally recognized co-host of the radio show Money On Tap and an active community leader, husband, and father.

Email: seth@brayshawfinancial.com

Website: brayshawfinancial.com

Podcast: https://www.brayshawfinancial.com/money-on-tap

Facebook: https://www.facebook.com/3Dinvesting/

Twitter: https://x.com/BFG_LLC/

Estate planning isn’t just about documents—it’s about protecting your family, your assets, and the legacy you leave behind.

Tammi Caress is the founder and principal attorney of Caress Law in Portland, Oregon, and one of the few trust and estate attorneys in the Pacific Northwest to hold an LL.M. in Estate Planning. With decades of experience in probate, trust administration, tax planning, and business succession, she helps families and business owners navigate complex estate planning decisions with clarity and confidence.

In this episode, Tammi joins Seth Krussman to discuss the most common estate planning mistakes, the importance of trusts and beneficiary coordination, planning for special needs family members, charitable giving strategies, business succession planning, and why collaboration between attorneys, financial advisors, and CPAs leads to better outcomes. She also shares practical guidance on keeping estate plans current and protecting loved ones from unnecessary taxes, delays, and complications.

Key Takeaways:

● Estate Planning Is More Than a Will: Effective planning starts with goals, strategy, and coordination across all assets and family circumstances.

● Review Your Plan Regularly: Major life events, tax law changes, and evolving family dynamics can quickly make an outdated plan ineffective.

● Trusts Can Solve Multiple Problems: Trusts can provide privacy, tax planning opportunities, asset protection, and support for beneficiaries with special needs.

● Business Succession Requires Early Planning: Owners who build businesses that can operate without them create more value and smoother transitions.

● Advisor Collaboration Matters: Coordinated planning between attorneys, financial advisors, and CPAs helps families avoid costly mistakes and achieve better outcomes.

Connect with Tammi:

Website: https://caresslaw.estate

LinkedIn: https://www.linkedin.com/company/caress-law/

Instagram: https://www.instagram.com/caresslaw/

Facebook: https://www.facebook.com/caresslaw.estate/

With Your Guest Host Seth Krussman:

Seth Krussman is a seasoned financial advisor and partner at Brayshaw Financial Group, LLC, with over 30 years of experience in entrepreneurship, business development, and wealth management. A Registered Representative and Investment Advisor Representative with Osaic Wealth, Inc., Seth specializes in tax-efficient investment strategies, executive compensation, and succession planning for high-net-worth clients. Based in Hillsboro, Oregon, he is also the nationally recognized co-host of the radio show Money On Tap and an active community leader, husband, and father.

Connect with Seth:

Website: https://www.brayshawfinancial.com/

Podcast: https://www.brayshawfinancial.com/money-on-tap

Facebook: https://www.facebook.com/3Dinvesting/

X: https://x.com/BFG_LLC/

Crypto taxes are getting more complicated fast — especially for investors, accountants, and financial advisors trying to keep up with new IRS reporting rules.

Perry Woodin is the CEO and co-founder of Node40, a digital asset accounting and analytics platform focused on crypto tax reporting, compliance, and financial reconciliation. In this episode, Perry breaks down the growing challenges around crypto taxes, 1099-DA reporting, digital asset compliance, and how financial advisors can better manage crypto within client portfolios.

He also explains how crypto investors create taxable events without realizing it, why many broker-issued crypto tax forms may be inaccurate, and how advisors and accountants can stay ahead as digital assets become more mainstream.

Key Takeaways:

● Crypto tax reporting is evolving quickly: New 1099-DA rules are creating confusion for investors, accountants, and advisors navigating digital asset compliance.

● Many crypto tax forms may be incomplete: Investors using multiple wallets or exchanges often receive inaccurate cost-basis reporting.

● Financial advisors need crypto visibility: Advisors increasingly need insight into digital asset holdings to manage full portfolio strategy and tax planning.

● Blockchain creates massive data complexity: Crypto transactions, staking rewards, liquidity pools, and yield strategies generate difficult-to-track tax events.

● Education remains the biggest hurdle: Many investors and professionals still underestimate the importance of understanding crypto tax obligations.

Estate planning isn’t just legal—it’s strategic, personal, and often misunderstood.

Natalie Smith, attorney at Sussman Shank LLP, specializes in advanced estate, trust, and tax planning for families, business owners, and advisors. With an LLM and deep experience at the intersection of tax law and real-world decision-making, she helps clients align wealth, values, and long-term intent.

In this episode, Natalie breaks down what “advanced” estate planning actually means, where high net worth families and business owners make costly mistakes, and how early coordination with advisors can dramatically improve outcomes. The conversation highlights practical strategies around trusts, gifting, tax mitigation, and family dynamics—while emphasizing that clarity, communication, and timing are what truly drive effective planning.

Key Takeaways:

● Know your assets: A complete, organized asset list is critical to ensure your estate plan actually works as intended.

● Titling matters: Even the best trust structure fails if assets aren’t properly aligned and funded.

● Plan before liquidity events: Early coordination helps avoid major tax consequences during sales or exits.

● Family dynamics drive strategy: Effective planning must account for relationships, roles, and communication.

● Start earlier than you think: Estate planning is most effective when treated as an ongoing, proactive process.

Connect with Natalie:

Website: https://www.sussmanshank.com/people/natalie-e-smith-ll-m/

LinkedIn: https://www.linkedin.com/in/natalieelizabethsmith/

With Your Guest Host Seth Krussman:

Seth Krussman is a seasoned financial advisor and partner at Brayshaw Financial Group, LLC, with over 30 years of experience in entrepreneurship, business development, and wealth management. A Registered Representative and Investment Advisor Representative with Osaic Wealth, Inc., Seth specializes in tax-efficient investment strategies, executive compensation, and succession planning for high-net-worth clients. Based in Hillsboro, Oregon, he is also the nationally recognized co-host of the radio show Money On Tap and an active community leader, husband, and father.

Connect with Seth:

Website: https://www.brayshawfinancial.com/

Podcast: https://www.brayshawfinancial.com/money-on-tap

Facebook: https://www.facebook.com/3Dinvesting/

X: https://x.com/BFG_LLC/

Helping seniors navigate one of life’s biggest transitions requires trust, empathy, and a true relationship-first approach.

Leroy Nashke, real estate agent with Silver Shores Realty and a Senior Real Estate Specialist, shares how he helps 55+ clients downsize, transition, and make confident decisions. He discusses building trust, coordinating services, avoiding costly mistakes, and why personal service and integrity separate advisors from transactional agents.

Key Takeaways:

● Relationship-first real estate: Building trust and personal connections leads to better outcomes and stronger referral-driven growth.

● Serving the 55+ market: Senior transitions require empathy, coordination, and guidance beyond a typical real estate transaction.

● Acting as a trusted advisor: Providing honest advice, even when it slows a deal, builds long-term credibility and client confidence.

● Negotiation and teamwork matter: Collaborating with agents and managing expectations helps deals stay together.

● Specialization creates differentiation: Focusing on senior downsizing and transitions helps stand out in a crowded real estate market.

Connect with Leroy:

Website:  https://www.silvershoresrealty.com

Connect with Mike Agol:

Website:  https://www.ridgecapitalmanagement.com/

What really happens when you owe the IRS—and how much of it is actually fixable?

In this episode of Sterling Insights, Tracy McCary sits down with Michael Raanan, Enrolled Agent and President of Landmark Tax Group. Together, they explore IRS back taxes and tax resolution, sharing valuable insights and practical tips for listeners. Michael draws from his experience as a former IRS revenue officer to discuss how tax debt is calculated, resolved, and sometimes reduced, offering actionable advice for individuals and business owners dealing with IRS issues. This episode is a must-listen for taxpayers, advisors, and anyone concerned about IRS debt, providing both knowledge and tools to navigate this important subject. 

Key Takeaways:

● Not All Tax Debt Is Accurate: Many IRS balances are overstated due to substitute returns—fixing filings can significantly reduce what’s owed.

● Cause, Cure, Compliance Framework: Understanding why the debt happened, how to resolve it, and how to stay compliant is key to long-term success.

● Multiple Resolution Options Exist: Payment plans, hardship status, and offers in compromise depend on financial analysis—not negotiation.

● IRS Mistakes Happen: Even large payments can be misapplied, leading to major penalties and long disputes.

● Beware of Tax Relief Scams: Many firms overpromise “pennies on the dollar” but fail to deliver real results.

Quotes from Michael Raanan:

● “It’s not that big of a deal when you owe back taxes—you just have to address it.”

● “The IRS is very black and white. It’s about what you qualify for, not negotiation.”

● “We hear it all the time—‘they didn’t do anything for me’—that’s the reality with a lot of these tax relief firms.”

Understanding how the IRS actually works—and what options truly exist—can turn a stressful tax problem into a manageable plan forward.

Connect with Michael:

Website:  https://landmarktaxgroup.com/

What if your CPA could do far more than file taxes—and actually help you build wealth, avoid costly mistakes, and align your finances with your life goals?

In this episode of Sterling Insights, Mike Agol sits down with Jon Czerwinski, CPA and Managing Partner, a strategic tax advisor specializing in entrepreneurs, investors, and high-growth businesses. Together, they explore the evolving role of CPAs as strategic partners in business growth, sharing valuable insights and practical tips for listeners. Jon draws from his extensive experience to discuss common misconceptions about CPAs, the importance of proactive tax planning, and how business owners can better align their financial strategies with long-term goals, offering actionable advice for entrepreneurs, business owners, and high-income professionals. This episode is a must-listen for anyone looking to move beyond basic tax preparation and leverage financial strategy for growth, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

● CPAs Are Strategic Advisors—Not Just Tax Preparers:

Many people misunderstand the role of a CPA. The real value lies in strategic planning, not just filling out forms.

● Annual Tax Planning Is the Minimum Standard:

Business owners should meet with their CPA at least once a year—ideally before year-end—to proactively reduce tax liability and adjust strategy.

● Your Tax Plan Must Align With Your Life Goals:

Whether your goal is lifestyle, monetization, or legacy, your financial strategy should reflect and support that vision.

● Ideal Clients Are Growth-Oriented and Engaged:

Entrepreneurs, strategic investors, side hustlers, and startups benefit most when they actively engage in the planning process.

● AI Is an Opportunity—Not a Replacement:

While AI can enhance efficiency, it cannot replace the strategic insight and personalized guidance of a skilled CPA.

Quotes from Jon Czerwinski:

● “If the only thing your CPA does is fill out a form, you don’t have a CPA.”

● “You hire a CPA for what’s between their ears—not the tax return they produce.”

● “Your life goals and your tax plan have to be in sync—otherwise, you’re working against yourself.”

The most successful business owners don’t treat their CPA as a once-a-year necessity—they treat them as a year-round strategic partner who helps guide smarter decisions, minimize risk, and maximize long-term success.

Connect with Jon:

Website - https://www.jccpas.com/

Instagram - https://instagram.com/jccpas/

LinkedIn - https://linkedin.com/company/jccpas/about/

Facebook - https://www.facebook.com/profile.php?id=61561069991961

Are you leaving money on the table because of poor tax planning — or worse, setting yourself up for an unexpected Medicare or IRS surprise?

In this episode of Sterling Insights, Tracy McCary sits down with Dana Lashbaugh, CPA and Owner of The CPA Group, a tax strategist specializing in business owners earning between $2M–$20M in revenue. Together, they explore proactive tax planning for business owners and retirees, sharing valuable insights and practical strategies that go far beyond basic tax preparation. Dana draws from his extensive experience in public accounting and as a former controller to discuss Roth conversions, IRMAA planning, 1099 estimated tax mistakes, succession planning, and smart exit strategies—offering actionable advice for business owners, independent contractors, and retirees.

This episode is a must-listen for entrepreneurs, construction and restaurant owners, and high-income professionals who want to reduce taxes, avoid costly surprises, and build a smarter long-term financial strategy.

Key Takeaways:

● Proactive Tax Planning Beats Reactive Tax Filing: Tax preparation is compliance — tax planning is strategy. Business owners who plan ahead can significantly reduce lifetime tax liability.

● Roth Conversions & IRMAA Awareness Matter in Retirement: Strategic Roth conversions can reduce required minimum distributions (RMDs) and prevent costly Medicare premium increases tied to income thresholds.

● 1099 Income Requires Quarterly Payments: Independent contractors must make estimated tax payments to avoid penalties and painful April surprises.

● Exit & Succession Planning Has Major Tax Implications: Selling, expanding, or transitioning a business requires careful asset allocation and coordination with advisors to minimize tax impact.

● Staffing Is the Biggest Challenge in Accounting Today: With hundreds of thousands of CPAs exiting the profession, access to responsive, relationship-driven advisory services is becoming increasingly valuable.

Quotes from Dana Lashbaugh:

● “We’re not just preparing tax returns — we’re helping clients plan where they’re going.”

● “There’s really no such thing as a quick tax question — because the right answer depends on the details.”

● “The pain is a lot easier quarterly than getting one big surprise bill on April 15th.”

Smart tax planning isn’t about being aggressive — it’s about being intentional. The earlier business owners and retirees plan, the more control they maintain over taxes, cash flow, and long-term wealth.

How do high-net-worth investors reduce concentrated stock risk and taxes—without blowing up their long-term plan?In this episode of Sterling Insights, Roger sits down with Gary Pattengale, CFP®, CPA, Senior Vice President and Advanced Planning Specialist at Mesirow Wealth Management.

Together, they explore tax-efficient strategies for managing concentrated stock positions, Roth conversions, and holistic wealth planning for high-net-worth families. Gary draws from over 25 years of experience to discuss concentration risk, tax-aware diversification strategies, and advanced planning techniques, offering actionable advice for investors, executives, and advisors navigating complex financial decisions. This episode is a must-listen for high-net-worth individuals and financial professionals seeking smarter, more integrated planning strategies.

Key Takeaways:

● Concentration Risk Starts Around 10%: While 10% in a single stock is a common rule of thumb, true risk tolerance depends on age, goals, income sources, and overall net worth.

● Create a Rules-Based Liquidation Strategy: Removing emotion from selling appreciated stock by setting pre-defined triggers can help investors diversify systematically and tax-efficiently.

● Roth Conversions Require Careful Modeling: Conversions can increase lifetime wealth—but hidden “tax torpedoes” like Social Security taxation, capital gains brackets, and Medicare premiums must be considered.

● Integrate Tax, Estate, and Investment Planning: The most effective strategies align tax efficiency, legacy intent, and portfolio design into one coordinated plan.

● Advanced Tools Improve Planning Outcomes: Modern tax and financial planning software allows advisors to model “what-if” scenarios efficiently, enabling dynamic, data-driven decisions.

Quotes from Gary Pattengale:

● “Taxes are important—but first we assess the concentration risk. What happens if that stock drops 40 to 60%?”

● “Once the rule is triggered, we execute. It takes the emotion out of it.”

● “Roth conversions aren’t for everybody. You really have to analyze the full tax impact before you act.”True wealth management isn’t about chasing returns—it’s about integrating tax strategy, risk management, and long-term planning into one cohesive approach that protects and grows wealth across generations.

Connect with Gary:

Website:  https://www.mesirow.com/home

LinkedIn:  https://www.linkedin.com/in/gary-pattengale-cfp%C2%AE-3806b822/

Connect with Roger:

Website:  https://www.sterlingfoundations.com

Facebook:  https://www.facebook.com/sterlingfoundations/

Twitter:  https://x.com/SterlingFndMgt?mx=2

LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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In this episode of Sterling Insights, Mike Agol sits down with Angie Smith, Agency Owner at Farmers Insurance and full-service risk protection specialist. Together, they explore how to properly protect your assets, family, and legacy through strategic insurance planning, sharing valuable insights and practical tips for listeners. Angie draws from her extensive experience to discuss common coverage gaps, umbrella policies, lawsuits, and misconceptions about “cheap” insurance, offering actionable advice for homeowners, business owners, and high-net-worth families. This episode is a must-listen for anyone building wealth who wants to make sure it’s properly protected, providing both knowledge and tools to navigate this critical subject.

Key Takeaways:

● Value Over Price: The cheapest policy is rarely the best policy. Proper coverage protects everything you’ve worked hard to build.

● Umbrella Policies Matter: An umbrella policy is one of the most affordable ways to shield assets from major lawsuits and liability claims.

● Coverage Gaps Are Common: Jewelry, small business exposures, and liability risks are often underinsured or misunderstood.

● Advisors Should Collaborate: Insurance and financial advisors must work together to fully protect a client’s portfolio.

● Insurance Is Personal: True service goes beyond policies — it means showing up during freezes, hurricanes, and life’s toughest moments.

Quotes from Angie Smith:

● “On a bad day, I want to make sure what you’ve built is still protected.”

● “An umbrella policy is the cheapest attorney you’ll ever have protecting your assets.”

● “We don’t just sell a policy — we sell value and proper protection.”

Building wealth is only half the equation — protecting it is what secures your legacy.

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How do you build a client-first financial firm from the ground up—and keep it human at scale?

In this episode of Sterling Insights, Roger sits down with Susie Cranston, President and COO of Crescent, a $65+ billion multifamily office and private investment firm. Together, they explore what it takes to deliver deeply personalized wealth management at scale, sharing valuable insights and practical tips for leaders, founders, and families navigating complex financial landscapes. Susie draws from decades of experience at McKinsey, First Republic, and now Crescent to discuss the power of culture, the evolution of client expectations, and how RIAs are reshaping wealth advisory. This episode is a must-listen for ultra-high-net-worth families, founders approaching liquidity, and professionals building modern client-first financial firms, providing both knowledge and tools to navigate this important subject.
 Key Takeaways:

● 💼 Client-First DNA: Crescent’s model was literally built by clients, for clients, offering flexibility that traditional banks can’t match.
● 🏛️ RIAs vs. Banks: Regulatory constraints limit the services banks can provide—RIAs like Crescent offer broader, deeper support in tax and private investing.
● 🔍 Fit Over Size: Crescent’s ideal client isn’t just about net worth—it’s about mindset and the desire for holistic, customizable support.
● 🧑‍🤝‍🧑 Team Culture Drives Client Success: Exceptional service starts with exceptional culture—Crescent prioritizes servant leaders and long interview processes to build elite teams.
● 📈 Scale Matters—for the Right Reasons: Being “industrial-grade” at $50B+ AUM allows for better infrastructure, tech, and access—without losing the boutique client feel.
 Quotes from Susie Cranston:

● “Our origin story is unique—we were built by clients, for clients.”
● “You can’t outsource culture. It’s the best predictor of organizational success.”
● “We aim to be the co-pilot in a family's financial life—scaling with them across the journey.”
 🔗 Crescent offers what most firms can’t: customized service backed by enterprise-level infrastructure. Learn more at crescentcapital.com and tune into this episode to see what the future of wealth management looks like.

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What if your tax problem isn’t actually a tax problem—but a bookkeeping one? Or what if the IRS doesn’t need to be feared, just better understood? This episode dives into the overlooked strategies and real-world solutions that could change the financial future of high-income earners and business owners.

In this episode of Sterling Insights, guest host Tracy McCary sits down with Adam Remis, CPA and founder of The Accounting Doctor. Together, they explore how advanced tax strategy and resolution can transform a client’s financial—and even physical—well-being, sharing valuable insights and practical tips for listeners. Adam draws from his 28+ years of experience to discuss how to effectively handle tax debt, avoid costly mistakes, and optimize taxes for high earners, offering actionable advice for wealth advisors, business owners, and high-income individuals. This episode is a must-listen for advisors with high-net-worth clients or anyone seeking smarter, proactive ways to tackle tax complexity.

Key Takeaways:

● Tax Resolution is More Than Numbers: Addressing tax debt isn’t just financial—it can dramatically improve a client’s mindset, health, and quality of life.
● Don't DIY the IRS: Trying to resolve issues with the IRS yourself can backfire. Adam explains why professional representation matters.
● Virtual Firms Are Winning: Adam shares how his remote model helps him recruit top talent and serve clients nationwide without geographic limitations.
● Tax Misconceptions Hurt Clients: Many people unknowingly overpay or misreport—leading to years of unnecessary stress or tax court battles.
● Advanced Strategies for High Earners: Adam reveals how clients earning $400k+ can use overlooked strategies to reduce income and capital gains taxes.

Quotes from Adam Remis:
● "Helping clients resolve their IRS debt isn’t just about money—it’s about lifting a massive psychological burden."
● "Doing it yourself with the IRS is like representing yourself in criminal court. You need an expert in your corner."
● "The details matter. We’ve saved clients tens of thousands simply by doing the digging their previous CPAs didn’t."

Whether you're an advisor looking to better support high-net-worth clients or someone navigating complex tax issues yourself, this episode offers a rare behind-the-scenes look at how smart strategy—and the right partner—can make all the difference.
Connect with Adam:
Website:  https://www.theaccountingdoctor.comLinkedIn:  https://www.linkedin.com/in/adam-b-remis-msim-cpa-l-i-o-n-b354b1/

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Think your job termination was unfair—and maybe even illegal? You’re not alone. But the difference between “unfair” and “unlawful” is more complex than most people realize. This episode dives deep into what employees (and employers) need to know about their rights in the workplace.
In this episode of Sterling Insights, guest host Peter Florio sits down with employment attorney Raymond Nardo, a seasoned legal expert with over 30 years of experience in labor and employment law. Together, they explore the realities of employment law, sharing valuable insights and practical tips for listeners. Raymond draws from his extensive experience to discuss wrongful termination, wage and hour disputes, discrimination claims, and the misconceptions employees often have about their rights, offering actionable advice for anyone navigating workplace challenges. This episode is a must-listen for professionals, business owners, HR managers, and employees facing tough job transitions, providing both knowledge and tools to understand and protect your rights.

Key Takeaways:

● The Harsh Truth About Employment at Will: Most private-sector employees can be terminated for any reason—or no reason at all—unless specific legal protections apply.
● Unfair ≠ Illegal: Many workplace terminations may feel unfair but don't meet the legal threshold for wrongful termination or discrimination.
● Wage & Hour Laws Are a Legal Minefield for Employers: Employers often violate wage laws without realizing it—missing notices, misclassifying employees, or improperly calculating overtime.
● Discrimination Protections Exist—but Proof Is Key: Laws protect against discrimination based on race, gender, age, and more, but proving it can be difficult and requires strong documentation.
● Legal Action Isn’t the Only Path: Sometimes, a well-crafted letter or negotiation can resolve disputes without litigation, especially when handled by an experienced advocate.

Quotes from Raymond Nardo:

● "Law and justice are distant cousins when it comes to employment law."
● "Nine out of ten people who call me don’t have a case—because employment at will gives employers broad leeway."
● "Even if we don’t win a case, we raise awareness—and that can change how employers operate going forward."

🔗 Conclusion:
Whether you’re an employee wondering if your termination was legal, or an employer navigating compliance, understanding the realities of employment law is critical. This episode sheds light on the rights, risks, and real-world processes behind workplace disputes.
Connect with Raymond: 
Website:  https://www.raynardo.com/
With Your Guest Host Peter Florio:
Peter F. Florio, CFP®, CLU®, ChFC®, CExP™, CLTC®, is the Founder and Managing Partner of The Florio Wealth Management Group in Westbury, NY. With nearly 40 years of experience, he provides comprehensive wealth, tax, and financial planning for high-net-worth individuals and business owners across the country.
Connect with Peter:
Website: https://www.floriowmg.com
LinkedIn: https://www.linkedin.com/company/florio-wealth-management-group/
Facebook: https://www.facebook.com/floriowmg
Calendly: https://calendly.com/floriowmg

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Most business owners think of legal help as something they’ll need later—but what if legal strategy could actually drive better decisions and prevent costly problems before they ever appear?
In this episode of Sterling Insights, guest host Seth Krussman sits down with Blaine Clooten, attorney at Brownstein Rask and a seasoned advisor to entrepreneurs, executives, and closely held businesses. Together, they explore how legal strategy shows up in real business decisions—not just in the courtroom, sharing valuable insights and practical tips for business owners and advisors alike. Blaine draws from his diverse background in business, litigation, and judging to discuss the risks business owners often overlook, offering actionable advice for those navigating contracts, partnerships, growth, and succession. This episode is a must-listen for entrepreneurs, operating executives, and advisors who support business owners, providing both knowledge and tools to build stronger, more resilient businesses.
Key Takeaways:
● Proactive vs. Reactive Legal Strategy: Waiting until there’s a problem limits your options—early legal involvement can protect relationships and reduce costs.
● Contracts Are Business Marriages: Too many business owners rush contracts without aligning them to their actual goals, leading to future disputes.
● Legal Counsel as Strategic Advisor: Good lawyers aren’t just for lawsuits—they're part of your growth and decision-making team.
● AI Can’t Replace Legal Judgment: Online tools may generate documents, but they can’t spot your unique risks—or defend you in court.
● Annual Legal Checkups Matter: Businesses evolve, and so should your legal documents. Regular reviews help avoid compounding issues.
Quotes from Blaine Clooten:
● “Most people wait until the problem is at their doorstep—by then, your options are limited and expensive.”
● “Signing a contract is like getting married—if you wouldn’t rush that, don’t rush the paperwork that ties your finances to someone else’s.”
● “The farther we get with technology, the more important trust-based relationships become in law and business.”
🔗 Conclusion:
Legal strategy isn’t about slowing you down—it’s about giving you clarity, confidence, and control before problems arise. If you’re building something meaningful, this episode will help you protect it.

Connect with Blaine:
Website:  https://brownsteinrask.com/attorneys/blaine-clooten

YouTube:  https://www.youtube.com/@clootenlawyer

LinkedIn:  https://www.linkedin.com/in/clooten/

With Your Guest Host Seth Krussman:
Seth Krussman is a seasoned financial advisor and partner at Brayshaw Financial Group, LLC, with over 30 years of experience in entrepreneurship, business development, and wealth management. A Registered Representative and Investment Advisor Representative with Osaic Wealth, Inc., Seth specializes in tax-efficient investment strategies, executive compensation, and succession planning for high-net-worth clients. Based in Hillsboro, Oregon, he is also the nationally recognized co-host of the radio show Money On Tap and an active community leader, husband, and father.
Connect with Seth:
Website:  https://www.brayshawfinancial.com/
Podcast:  https://www.brayshawfinancial.com/money-on-tap
Facebook:  https://www.facebook.com/3Dinvesting/
X:  https://x.com/BFG_LLC/

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What does it really take to thrive in real estate for nearly three decades—through changing markets, interest rate spikes, and personal reinvention? This episode explores how longevity, trust, and adaptability can create a resilient real estate career. In this episode of Sterling Insights, guest host Tracy McCary sits down with Greg Roberts, a seasoned real estate consultant with expertise in both residential and commercial real estate. Together, they explore how building trust and adapting to market shifts has sustained Greg’s business since the mid-90s, sharing valuable insights and practical tips for listeners. Greg draws from his extensive experience to discuss interest rate fluctuations, client evolution, and the shift from cold calls to warm referrals, offering actionable advice for advisors, realtors, and professionals serving high-net-worth individuals. This episode is a must-listen for real estate professionals, financial advisors, and business owners navigating growth in volatile markets, providing both knowledge and tools to navigate this important subject. Key Takeaways: ● Adaptability is Key: Greg transitioned from pharmaceuticals to real estate and grew with the industry—adapting from entry-level buyers to million-dollar clients. ● Trust Drives Referrals: After decades in the business, most of Greg’s leads now come from word of mouth, not advertising. ● Commercial Real Estate as a Growth Lever: Expanding into commercial deals re-energized his business and client relationships. ● Interest Rates are Psychological as Much as Financial: Greg offers context on how consumers perceive 7% rates vs. the recent anomaly of 2–3%. ● Being a "Truth Teller" Pays Off: Greg’s honest approach—telling clients what they need to hear, not just what they want—has built long-term credibility. Quotes from Greg Roberts: ● "I tell you the truth—even if it costs me the listing." ● "You don't know what you don't know—and that's where a trusted advisor matters." ● "I become family to my clients for 30, 60, 90 days during a deal—and then I may not hear from them for two years." 🔗 Conclusion: Whether you're an advisor, real estate pro, or just curious about sustaining success over the long haul, this episode delivers powerful lessons on trust, client service, and staying relevant in a shifting market.

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What does it really take to thrive in real estate for nearly three decades—through changing markets, interest rate spikes, and personal reinvention?

This episode explores how longevity, trust, and adaptability can create a resilient real estate career.

In this episode of Sterling Insights, guest host Tracy McCary sits down with Greg Roberts, a seasoned real estate consultant with expertise in both residential and commercial real estate. Together, they explore how building trust and adapting to market shifts has sustained Greg’s business since the mid-90s, sharing valuable insights and practical tips for listeners. Greg draws from his extensive experience to discuss interest rate fluctuations, client evolution, and the shift from cold calls to warm referrals, offering actionable advice for advisors, realtors, and professionals serving high-net-worth individuals. This episode is a must-listen for real estate professionals, financial advisors, and business owners navigating growth in volatile markets, providing both knowledge and tools to navigate this important subject.
Key Takeaways:
● Adaptability is Key: Greg transitioned from pharmaceuticals to real estate and grew with the industry—adapting from entry-level buyers to million-dollar clients.
● Trust Drives Referrals: After decades in the business, most of Greg’s leads now come from word of mouth, not advertising.
● Commercial Real Estate as a Growth Lever: Expanding into commercial deals re-energized his business and client relationships.
● Interest Rates are Psychological as Much as Financial: Greg offers context on how consumers perceive 7% rates vs. the recent anomaly of 2–3%.
● Being a "Truth Teller" Pays Off: Greg’s honest approach—telling clients what they need to hear, not just what they want—has built long-term credibility.
Quotes from Greg Roberts:
● "I tell you the truth—even if it costs me the listing."
● "You don't know what you don't know—and that's where a trusted advisor matters."
● "I become family to my clients for 30, 60, 90 days during a deal—and then I may not hear from them for two years."

🔗 Conclusion:
Whether you're an advisor, real estate pro, or just curious about sustaining success over the long haul, this episode delivers powerful lessons on trust, client service, and staying relevant in a shifting market.

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Most business owners fear litigation—but what if the real danger lies in the mistakes made long before a lawsuit is ever filed?
In this episode of Sterling Insights, Seth Krussman sits down with Josi Kovacs, a seasoned commercial litigator from one of the Pacific Northwest’s top boutique firms. Together, they explore how business owners can navigate and avoid complex litigation, sharing valuable insights and practical tips for listeners. Our guest draws from extensive trial and mediation experience to discuss common legal pitfalls, emotional decision-making, and the true cost of waiting too long to call an attorney, offering actionable advice for entrepreneurs, founders, and leaders of closely held businesses. This episode is a must-listen for anyone leading a growing business, providing both knowledge and tools to navigate legal risk before it escalates.

Key Takeaways:

● Litigation Is Rarely the End: Most lawsuits aren’t catastrophic, and there are always paths forward—if you know your options.
● Write It Down: Business owners often skip documentation to preserve relationships, but this can create costly disputes later.
● Call a Lawyer Early: Bringing in litigation counsel before things escalate can help resolve issues before a suit is ever filed.
● Know Your Contracts: Many business leaders sign indemnity clauses without understanding them—until it’s too late.
● Understand the Emotional Toll: Lawsuits aren’t just financial; they’re emotionally draining. Knowing that can shape better decisions.

Quotes from the Josi:

● “Litigation is such a stressful experience—even for seasoned businesspeople.”
● “Litigation isn’t just expensive—it’s emotionally draining. You could be tied up for years, facing someone you no longer trust.”
● “So many problems could be avoided if people just wrote things down. You don’t need legalese—just an email that says, ‘This is what we agreed to.”

🔗 Conclusion:
Complex litigation isn’t just about courtrooms—it's about strategy, emotion, and preparation. This episode offers a roadmap for business owners to protect themselves long before disputes arise.
Connect with Josi:
Website:  https://www.markowitzherbold.com/Josephine-Josi-Kovacs LinkedIn:  https://www.linkedin.com/in/josephine-kovacs/\
With Your Guest Host Seth Krussman:
Seth Krussman is a seasoned financial advisor and partner at Brayshaw Financial Group, LLC, with over 30 years of experience in entrepreneurship, business development, and wealth management. A Registered Representative and Investment Advisor Representative with Osaic Wealth, Inc., Seth specializes in tax-efficient investment strategies, executive compensation, and succession planning for high-net-worth clients. Based in Hillsboro, Oregon, he is also the nationally recognized co-host of the radio show Money On Tap and an active community leader, husband, and father.
Connect with Seth:
Website:  https://www.brayshawfinancial.com/
Podcast:  https://www.brayshawfinancial.com/money-on-tap
Facebook:  https://www.facebook.com/3Dinvesting/
X:  https://x.com/BFG_LLC/

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In this episode of Sterling Insights, guest host Tracy McCary sits down with Taner Neighbors, a commercial real estate broker and third-generation real estate professional. Together, they explore the transition from residential real estate to commercial development, sharing valuable insights and practical tips for listeners navigating this complex industry. Tanner draws from his extensive experience to discuss the challenges of starting during a market crash, the evolving demands of the commercial sector, and how to bring value as a trusted advisor, offering actionable advice for professionals looking to elevate their role in real estate.

This episode is a must-listen for advisors, brokers, and anyone eyeing a move into commercial real estate or development, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

• Start Where You Are: Launching a real estate career during the 2008 crash taught Tanner resilience, creativity, and long-term grit.
  

• Residential vs. Commercial: Why Tanner moved away from residential sales and how commercial real estate offers deeper value and specialization.
  

• The Power of Partnerships: How working with a seasoned developer has opened doors in capital raising and ground-up projects.
  

• Market Impact of Interest Rates: Understanding how even small interest rate changes drastically shift commercial property valuations.
  

• Become the Trusted Advisor: It’s not about being everywhere—it’s about evolving daily and being the expert people rely on.
  

Quotes from Taner Neighbors:

• "I don't like selling houses—I enjoy the commercial side of things tremendously."
  

• "Interest rates 100,000% drive the commercial real estate market."
  

• "A true professional can make your life very easy. Time is something we can never get back."
  

🔗 Conclusion:

This episode highlights what it takes to move beyond transactional real estate into a role of influence, strategy, and long-term impact. Whether you're advising high-net-worth clients or building your own real estate career, Taner’s journey offers both inspiration and a roadmap forward.

Connect with Taner:

LinkedIn:  https://www.linkedin.com/in/neighborssells/

Connect with Tracy:

Website:  https://tracwealthmanagement.com/

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Think your estate plan is “simple”? Think again. This episode will make you rethink what it really takes to protect your family, your assets, and your legacy.

In this episode of Sterling Insights, guest host Peter Florio sits down with attorney and estate planning expert Robin Maynard, partner at Marquesian Mayer. Together, they explore the complexities of estate planning for high-net-worth families, sharing valuable insights and practical tips for listeners. Robin draws from her extensive experience to discuss common pitfalls, tax-saving strategies, and why proper trust planning is essential. This episode is a must-listen for financial advisors, wealth managers, and families with significant assets, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

● Trusts Simplify—and Speed Up—the Estate Process: Avoid probate delays by ensuring assets are properly titled within a trust.
● Tax Law Is a Moving Target: Estate plans must include flexibility to adapt to evolving federal and state tax laws.
● Family Dynamics Can Complicate Estates: Proactive planning minimizes family conflict and emotional strain after a death.
● Everyone Thinks Their Estate Is “Simple”—Until It Isn’t: Even straightforward estates come with complexities most people overlook.
● Collaborating with Financial Advisors Is Critical: Integrated planning between legal and financial professionals leads to better outcomes for clients.

Quotes from Robin Maynard:

● “Every conversation starts with, ‘This is simple,’ and then it never is.”
● “People don’t realize their estate plan fails if their trust is empty.”
● “The bureau will take your money for tuition, but won’t give you a refund check without a power of attorney.”
🔗 Conclusion:
Estate planning isn’t just for the ultra-wealthy or the elderly—it’s for anyone who wants clarity, control, and peace of mind for the future. This episode lays out what smart planning looks like—and why it pays to get it right.

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What does it take to scale a $10B RIA while staying true to a client-first culture? This episode explores the systems, people, and strategies behind sustainable growth in wealth management.

In this episode of Sterling Insights, Roger sits down with Scott Brown, President of Pinnacle Associates, a multibillion-dollar RIA serving high net worth families and institutions. Together, they explore what it takes to build and grow a thriving independent advisory firm, sharing valuable insights and practical tips for listeners. Scott draws from his extensive legal and operational experience to discuss the evolution of the RIA space, the importance of culture, and how firms can stay competitive in a fast-changing landscape. This episode is a must-listen for financial advisors, firm leaders, and professionals serving HNW clients, providing both knowledge and tools to navigate growth, succession, and innovation in wealth management.

🔑 Key Takeaways:

● Culture Drives Client Experience: Pinnacle prioritizes internal culture, believing happy, respected employees create the best outcomes for clients.

● Built to Scale: From in-house investment management to advisor training programs, Pinnacle is structured to grow without sacrificing quality.

● Focus on the $2M–$20M Client: Their ideal client range allows for deep planning relationships, with business owners and entrepreneurs being a core audience.

● Organic + Inorganic Growth Strategy: Pinnacle targets 5%+ organic growth while selectively pursuing M&A to expand strategically.

● Future-Proofing the RIA: With initiatives like the Next Gen Committee and Pinnacle Academy, they’re investing in leadership, tech, and talent to stay ahead.

💬 Quotes from Scott Brown:

● "We’re trying to build a firm that thinks three chess moves ahead — not just one client meeting at a time."

● "Culture is the number one thing we care about. Good people lead to great client experiences."

● "It’s a unique time in the RIA world — consolidation, AI, and client expectations are all shifting. You need to be paying attention."

🔗 Conclusion: If you're serious about growing a client-first advisory business that lasts, this episode delivers real-world strategies from the front lines of a $10B RIA.

Connect with Scott:

Website:  https://www.pinnacle-associates.com

LinkedIn:  https://www.linkedin.com/in/scottbrown1999/

LinkedIn:  https://www.linkedin.com/company/pinnacle-associates/?viewAsMember=true

Connect with Roger:

Website:  https://www.sterlingfoundations.com

Facebook:  https://www.facebook.com/sterlingfoundations/

Twitter:  https://x.com/SterlingFndMgt?mx=2

LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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What happens when a pro basketball player trades the court for cash flow consulting? This episode dives into how blue-collar businesses can build wealth with the right CPA on their team.
In this episode of Sterling Insights, guest host Tracy McCary sits down with Mark Stiles, CPA and founder of MAS CPA. Together, they explore the power of proactive accounting and fractional CFO services, especially for trades and service-based businesses. Mark draws from his unique journey—from professional athlete to CPA—to discuss the challenges business owners face when scaling, including job costing, tax strategy, and navigating debt. This episode is a must-listen for advisors, accountants, and business owners working with high-net-worth individuals or growing blue-collar companies, offering both insights and action steps to take control of financial outcomes.

Key Takeaways:

• 🛠️ Know Your Niche: Trades businesses between $500K–$5M in revenue are often under-served—and wildly profitable with the right financial structure.
  
• 💰 Job Costing = Hidden Cash Flow: Most tradespeople don’t track profitability per job, leading to money left on the table.
  
• 📊 From Compliance to Strategy: CPAs must evolve from number crunchers to storytellers who help owners make smarter decisions.
  
• 🧠 DIY Pitfalls Are Real: Self-filing taxes or doing your own books often leads to costly mistakes—smart business owners delegate.
  
• 🚀 Charge for Your Value: Professionals need to stop pricing hourly and start pricing based on outcomes and real value delivered.
  

• “We’re not just pencil pushers. We’re storytellers—and that’s where the real value is.”
  
• “If you’re not resonating with your client, then you’re not a fit—and the relationship won’t be fruitful.”
  
• “Don’t penny-pinch on your professionals. That’s the lifeblood of your business.”
  

Quotes from Mark Stiles:

Connect with Mark:
Website:  https://www.markstilescpa.com
LinkedIn:  https://www.linkedin.com/company/mascpa/
Facebook:  https://www.facebook.com/share/1AscCpnvMy/?mibextid=wwXIfr
Instagram: https://www.instagram.com/mascpa_?igsh=Z2ZkYzk3c3RueDlm&utm_source=qr

Podcast: https://open.spotify.com/show/1Xgh8G0ENtln59anAwZwFI?si=nr6-xh12R26JcV9lqBtcqQ&nd=1&dlsi=27d11b68be02409a
Connect with Tracy:
Website:  https://tracwealthmanagement.com/
🔗 Conclusion:
This episode shows how CPAs can be growth engines—not just compliance officers—for trades and high-net-worth clients. With storytelling, strategy, and specialization, accounting becomes a superpower.

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What happens when a small-town kid from a dairy farm builds a modern, cloud-based accounting firm serving blue-collar business owners nationwide? You get a fresh take on holistic financial services that’s rooted in hard work and real-world impact.
In this episode of Sterling Insights, guest host Charles Trakas sits down with Cody Roos, Enrolled Agent and founder of FinPro Accounting. Together, they explore how to build a full-service, client-first accounting firm tailored to the unique needs of blue-collar entrepreneurs and financial professionals. Cody draws from his diverse background in farming, financial services, and tax planning to discuss the gaps small business owners face in accounting, payroll, and tax compliance, offering actionable advice for advisors and entrepreneurs alike. This episode is a must-listen for advisors, accountants, and business owners who want to deliver greater value while scaling smartly.

Key Takeaways:

• 💼 Holistic Service Wins: Cody shares how adding tax, payroll, and bookkeeping services filled critical gaps for clients—and grew his business.
  
• 🧠 AI as a Study Partner: He credits ChatGPT with helping him pass the Enrolled Agent exam quickly and effectively.
  
• 🧰 Supporting Blue-Collar Entrepreneurs: Many clients just want to do great work—Cody handles the rest so they can grow.
  
• 🌐 Cloud-Based, Nationwide Firm: Learn how FinPro serves clients across the U.S. with zero paper and 100% trust.
  
• 📊 Tiered Pricing = Smarter Scaling: A client told Cody he wasn’t charging enough—now he offers three tiers that align value with service.
  

• "I don’t necessarily think I’ve become an expert in any one area—my focus is adding as much value as possible."
  
• "Every person you meet knows something you don’t know."
  
• "I never want to become a tax return factory. Quality is everything."

Quotes from Cody Roos:

Connect with Cody:
Website:  https://www.finproaccounting.com/wp/wp-admin/LinkedIn: https://www.linkedin.com/in/cody-roos
Connect with Charles:
Website:  https://proactivetaxreductions.com/about-us/ LinkedIn:https://www.linkedin.com/in/businessownertaxreductionadvisor/ Facebook Business:https://www.facebook.com/TrakasFinancial  Facebook Personal:https://www.facebook.com/profile.php?id=100011447285280
🔗 Conclusion:
Whether you serve farmers, contractors, or financial advisors, delivering integrated, high-trust accounting services can transform your client relationships—and your business.

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What happens to your clients, your team, and your business if something happens to you tomorrow? This episode dives into why every financial advisor needs a documented succession plan—before it’s too late.

In this episode of Sterling Insights, Roger sits down with PJ McDaniel, Partner at Socium Advisors and a leader in advisor growth strategy within Northwestern Mutual. Together, they explore succession planning for financial advisors, sharing valuable insights and practical tips for listeners. PJ draws from his extensive experience in wealth management and M&A to discuss the demographic shift in the industry, the risks of poor planning, and how to transition client relationships and enterprise value effectively, offering actionable advice for advisors working with high-net-worth clients. This episode is a must-listen for advisors looking to protect their legacy, their clients, and their families, providing both knowledge and tools to navigate this critical business decision.

Key Takeaways:

● Most Advisors Lack a Plan: Up to 94% of advisors don’t have a documented succession plan—leaving clients and families vulnerable.
● Start Early: Succession planning isn’t just for retirement; it's risk management in case of unexpected events.
● Trusted Partnerships Matter: A successful transition hinges on finding the right next-gen partner and building trust over time.
● Valuation Confusion: Many advisors don’t fully understand what their business is worth or how M&A dynamics affect value.
● Culture Fit First: When considering a merger or acquisition, cultural alignment is more important than revenue or AUM.

Quotes from PJ McDaniel:

● “It’s like having a will—you hope you never need it soon, but if you do and don’t have it, the consequences can be huge.”
● “The most successful transitions we’ve seen are built over two to three years, not two to three months.”
● “If you’re not spending most of your time with clients, something needs to change—that’s where we come in.”
🔗 Conclusion:
If you’re an advisor without a clear, written succession plan—or just want a second opinion—this episode offers the clarity and next steps you need.
Connect with PJ:
Website:  https://sa.nm.com/
Connect with Roger:Website:  https://www.sterlingfoundations.comFacebook:  https://www.facebook.com/sterlingfoundations/Twitter:  https://x.com/SterlingFndMgt?mx=2LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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Think you understand how insurance companies operate behind the scenes? Think again. This episode dives deep into how businesses can protect themselves—and win—when insurers don't play fair.
In this episode of Sterling Insights, guest host Peter Florio sits down with Evan Schwartz, a nationally recognized attorney and insurance recovery expert. Together, they explore the complex world of insurance claims litigation and recovery, sharing valuable insights and practical tips for listeners. Evan draws from over 30 years of experience to discuss what businesses often misunderstand about legal battles with insurers, offering actionable advice for advisors, entrepreneurs, and business owners. This episode is a must-listen for professionals who work with high-net-worth clients or manage risk, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

● 📈 Understanding Insurance Recovery: Learn how businesses can fight back when insurance companies deny or delay legitimate claims.
● 💼 From Law to Business: Why many lawyers struggle running a firm—and what Evan did differently to build a successful, client-focused practice.
● 🧠 Empathy in Advocacy: Discover how emotional intelligence and listening deeply can set legal professionals apart.
● 🧩 Big Picture Strategy: Why Evan believes that lawyers must stop being “just lawyers” and start thinking like business owners.
● ⚖️ Landmark Legal Action: Hear how Evan’s class action lawsuit reshaped a national insurance company’s claims practices—and helped thousands of policyholders.

Quotes from Evan Schwartz:

● “Clients want to spend as little time and money with their lawyer as possible—and that’s the truth.”
● “Empathy is one of the great keys of life, especially for a lawyer. You need to truly listen with intent.”
● “You can learn about many different professions as a lawyer without actually being in those professions—that’s what keeps me engaged.”
🔗 Conclusion:
Whether you're advising clients, running a business, or navigating your own insurance dispute, this episode offers a front-row seat to the mindset and strategy behind real legal impact.
Connect with Evan:
Firm Website: https://schlawpc.com/LinkedIn Profile: https://www.linkedin.com/in/evansschwartz/
With Your Guest Host Peter Florio:
Peter F. Florio, CFP®, CLU®, ChFC®, CExP™, CLTC®, is the Founder and Managing Partner of The Florio Wealth Management Group in Westbury, NY. With nearly 40 years of experience, he provides comprehensive wealth, tax, and financial planning for high-net-worth individuals and business owners across the country.
Connect with Peter:
Website: https://www.floriowmg.com
LinkedIn: https://www.linkedin.com/company/florio-wealth-management-group/
Facebook: https://www.facebook.com/floriowmg
Calendly: https://calendly.com/floriowmgNew boost

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What if a few smart moves could save you millions in taxes on your tech equity or crypto gains? This episode dives into the real strategies high-earning professionals need to know—but most don’t.
In this episode of Sterling Insights, Roger sits down with a seasoned financial planner who specializes in working with high-net-worth professionals in tech and crypto. Together, they explore advanced tax planning strategies, sharing valuable insights and practical tips for listeners. Drawing from extensive experience with clients holding concentrated equity and crypto portfolios, the guest discusses how to manage equity compensation, minimize taxes, and plan charitable giving. This episode is a must-listen for tech and crypto professionals sitting on major unrealized gains, offering both clarity and tools to take control of their financial future.

Key Takeaways:

● 💼 Equity Compensation 101: Understand the differences between RSUs, ISOs, and NSOs—and why timing matters more than you think.
● 🧾 AMT Pitfalls: Learn how the Alternative Minimum Tax affects stock option planning and what to do before you exercise.
● 💸 CRT Strategy: Discover how a Charitable Remainder Trust can help you diversify and generate income without triggering a tax bomb.
● 🪙 Crypto Planning: Why crypto gains are taxable, how to manage your holdings, and the importance of getting your tokens "into the system."
● 🧠 Risk & Goals Alignment: How to evaluate your wealth not just by numbers, but by what it allows you to do—from buying real estate to funding early retirement.

Quotes from the guest:

● “We always start with: What do you want your money to do for you?”
● “You can look on paper and think, ‘I’ve got $3 million in stock,’ but if you don’t plan, you might only keep half.”
● “It’s not about just paying less tax—it’s about using that money to fuel the life you want.”
🔗 Conclusion:
If you're holding significant equity or crypto and want to avoid massive tax bills while securing your financial future, this episode is your roadmap.
Connect with Jennifer:
Website:  https://www.modernfamilyfinance.com/
Connect with Roger:Website:  https://www.sterlingfoundations.comFacebook:  https://www.facebook.com/sterlingfoundations/Twitter:  https://x.com/SterlingFndMgt?mx=2LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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What does it take to build a family office with a $25M minimum and serve first-generation entrepreneurs navigating complex wealth? This episode breaks it down.

In this episode of Sterling Insights, Roger sits down with Chad Willardson, founder of Pacific Capital and advisor to ultra-high-net-worth founders. Together, they explore how to serve first-gen entrepreneurs with complex financial lives, sharing valuable insights and practical tips for advisors and families alike. Chad draws from his extensive experience building a boutique family office to discuss client fit, private investments, multi-generational planning, and how to say no—even to $100M prospects, offering actionable advice for those working with high-net-worth individuals. This episode is a must-listen for financial advisors, family office professionals, and entrepreneurial families, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

● 💼 Know Your Ideal Client: Why Chad only serves first-gen founders with $25M+ and how he defines perfect-fit clients.

● 🧠 Be the Peer, Not Just the Planner: How being an entrepreneur himself makes Chad more effective as an advisor.

● 📊 Private Deals Are Everywhere: How his team evaluates hundreds of private investment opportunities each year for clients.

● 🧒 Smart, Not Spoiled: Why teaching kids about money early is essential—and how not to ruin the next generation.

● 🛩️ Lifestyle Decisions Matter: What to consider when clients ask, “Should I buy a jet?”

Quotes from Chad Willardson:

● "I’m more of a peer to my clients than just their advisor."

● "You don’t have to do business with people who aren’t a good personal fit."

● "Making money easy doesn’t make someone good with money."

🔗 Conclusion:

Serving ultra-wealthy entrepreneurs isn’t just about investing—it’s about simplifying their lives, protecting their time, and helping them think clearly in high-stakes moments.

Connect with Chad:

Website:  http://chadwillardson.com/

Connect with Roger:

Website:  https://www.sterlingfoundations.com

Facebook:  https://www.facebook.com/sterlingfoundations/

Twitter:  https://x.com/SterlingFndMgt?mx=2

LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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You might think you have time to plan your legacy—but waiting too long could cost your family dearly. In this episode of Sterling Insights, host Seth Krussman sits down with Aaron Frishman, of counsel at Gevurtz Menashe and an expert in estate, tax, and elder law planning. Together, they explore the complexities of estate planning for business owners and high-net-worth families, sharing valuable insights and practical tips to protect what matters most. Aaron draws from over two decades of legal experience to discuss common missteps, asset protection strategies, and long-term care planning, offering actionable advice for families, entrepreneurs, and financial professionals alike.
This episode is a must-listen for business owners, advisors, and affluent families looking to stay ahead of tax changes, preserve generational wealth, and avoid costly planning mistakes.

Key Takeaways:

• 🧠 Plan Early: Waiting too long to start estate planning often leads to unnecessary taxes, legal confusion, or family conflict.
  
• 🏠 Avoid Probate: Use revocable trusts and proper titling to ensure smooth transitions and privacy for heirs.
  
• ⚖️ State Taxes Matter: Oregon and Washington have aggressive estate tax thresholds that catch many families off guard.
  
• 👨‍👩‍👧 Family Assumptions Are Dangerous: Assigning roles based on tradition (like making the oldest child a trustee) can backfire—fit matters more than form.
  
• 🛡️ Long-Term Care Planning Is Crucial: Without insurance or trust-based strategies, healthcare costs can drain family wealth quickly.
  

• “Most people think they have more time. The truth is, things change fast—and if you wait, your options shrink.”
  
• “A trust with nothing in it is like a safe with no valuables. You have to fund it, or it’s just a document.”
  
• “Just because someone’s your oldest child doesn’t mean they’re the right person to manage your estate.”
  

Quotes from Aaron Frishman:

🔗 Conclusion: Estate planning isn’t just for the ultra-wealthy—it’s about protecting your legacy, your family, and your future. Starting now is the smartest move you can make.
Connect with Aaron:
Website:  www.gevurtzmenashe.com LinkedIn:  https://www.linkedin.com/in/aaronfrishman/
With Your Guest Host Seth Krussman:
Seth Krussman is a seasoned financial advisor and partner at Brayshaw Financial Group, LLC, with over 30 years of experience in entrepreneurship, business development, and wealth management. A Registered Representative and Investment Advisor Representative with Osaic Wealth, Inc., Seth specializes in tax-efficient investment strategies, executive compensation, and succession planning for high-net-worth clients. Based in Hillsboro, Oregon, he is also the nationally recognized co-host of the radio show Money On Tap and an active community leader, husband, and father.
Connect with Seth:
Website:  https://www.brayshawfinancial.com/
Podcast:  https://www.brayshawfinancial.com/money-on-tap
Facebook:  https://www.facebook.com/3Dinvesting/
X:  https://x.com/BFG_LLC/

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Most advisors manage money—but what separates the top 20% from the rest is how they manage relationships, structure their practice, and scale with intention. Are you investing your time where it matters most?

In this episode of Sterling Insights, Roger sits down with Duncan MacPherson, CEO of Pareto Systems and a practice management expert for top financial advisors. Together, they explore how elite advisors create enterprise value by professionalizing their client experience, sharing valuable insights and practical tips for listeners. Duncan draws from over 30 years of experience to discuss the pitfalls of plateauing, the power of process, and how to grow a business that truly serves your life. This episode is a must-listen for advisors who work with high-net-worth clients and want to grow by design—not by default, providing both knowledge and tools to navigate this critical evolution.

Key Takeaways:

● 🧠 The 80/20 Principle in Practice: How elite advisors focus 80% of their energy on the 20% of clients who drive results—and why most advisors still get it backward.

● 🛠️ Professionalizing the Client Experience: Why it’s no longer enough to rely on product and performance, and how to build a proprietary process that creates real differentiation.

● 📈 From Practice to Business: The stages of growth—growing, teaming, scaling, and exiting—and how to move from reactive to intentional.

● 🎯 Finding and Serving Your Ideal Client: Tools like the Practice Management Index (PMI) help advisors identify gaps and realign around what matters most.

● 🤝 Positioning vs. Pitching: Why complex clients don’t want to be sold—they want to buy into a vision, process, and partnership.

Quotes from Duncan MacPherson:

● "You’re not asking a client to buy something—you’re asking them to buy into something."

● "The business is supposed to serve your life, not the other way around."

● "If you're not adapting, you're plateauing. Minor adjustments over time can lead to major improvements."

🔗 Conclusion:

Success today isn’t just about assets under management—it’s about building a business with process, purpose, and professional contrast. If you want to scale intentionally and future-proof your practice, this episode is your starting point.

Connect with Duncan:

Website:  www.paretosystems.com

Podcast:  https://always-on-with-d-macpherson.blubrry.net/

Connect with Roger:

Website:  https://www.sterlingfoundations.com

Facebook:  https://www.facebook.com/sterlingfoundations/

Twitter:  https://x.com/SterlingFndMgt?mx=2

LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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Are CPA firms really ready for succession—or just hoping they’ll figure it out later? Discover why waiting is the costliest mistake a firm can make.
In this episode of Sterling Insights, guest host Charles Trakas sits down with a seasoned advisor and CPA-turned-growth consultant, Daniel McMahon. Together, they explore succession planning, governance, and building enterprise value in CPA firms, sharing valuable insights and practical tips for listeners. Drawing from decades of experience in public accounting and management consulting, the guest unpacks the common challenges firms face when planning for transition and offers actionable advice to create firms that are sustainable, transferable, and truly valuable.
This episode is a must-listen for firm leaders, partners, and advisors working with CPA firms, providing both knowledge and tools to navigate succession with confidence.

Key Takeaways:

● 🔁 Succession Is a Process, Not an Event: Planning early and treating succession like a process—rather than a one-time event—ensures smoother transitions and sustained firm value.
● 🧱 Strong Governance Builds Strong Firms: Implementing clear governance structures creates accountability, alignment, and sets the foundation for long-term growth.
● 🕰️ The Tyranny of the Now: Many firm owners delay planning because they’re overwhelmed by day-to-day demands—this mindset threatens future viability.
● 🧠 Intellect Isn’t Enough—Action Is Required: Even highly intelligent partners struggle to act on succession plans without outside support and structure.
● 💼 Build a Business, Not Just a Book: Firms that are sustainable and transferable command higher valuations and are more attractive to buyers or internal successors.

Quotes from Daniel McMahon:

● “I’m not here to outsmart my clients. I’m here to help them take a step forward.”
● “Governance isn’t just board minutes—it’s a cultural process that drives alignment.”
● “If your firm is sustainable and transferable, you’re not just selling a practice—you’ve built an enterprise.”
🔗 Conclusion:
Succession doesn’t start when you’re ready to exit—it starts when you decide to build a firm that can thrive without you.

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What happens when a corporate dealmaker hits midlife and chooses law school over a sports car? In this episode, discover how attorney Kevin Timson brings deep business insight to legal strategies that help entrepreneurs and auto dealers plan smarter exits and succession.

In this episode of Sterling Insights, guest host Peter Florio sits down with Kevin Timson, an attorney at ArentFox Schiff with over 25 years of combined business and legal experience. Together, they explore succession planning, business exits, and long-term legal strategy for entrepreneurs and automotive dealership owners, sharing valuable insights and practical tips for listeners. Kevin draws from his unique path—from business development to boutique law firms to a national firm—offering real-world advice on navigating ownership transitions, valuations, and family business complexities. This episode is a must-listen for advisors, attorneys, and business owners planning for the future, providing both knowledge and tools to navigate this critical phase of business life.

Key Takeaways:

● 🔁 Succession Planning Isn’t One-Size-Fits-All: Kevin explains how every succession plan must be tailored to the family dynamics, asset types, and future goals of each business owner.
● 💼 Valuation is More Art Than Science: Owners often cling to fixed numbers, but Kevin emphasizes that value is ultimately what a willing buyer and seller agree on.
● 🧠 Business Owners Struggle to Zoom Out: Many entrepreneurs get stuck in day-to-day operations and neglect long-term planning—until it's too late.
● 🧭 Trust is the Cornerstone of Advisory Relationships: Whether attorney or wealth advisor, success starts with mutual trust and a shared goal.
● 🛠️ Your Legal Partner Should Be a Problem-Solving Sherpa: Kevin sees himself as a flexible problem-solver who listens first and then curates legal strategies from a vast network of resources.

Quotes from Kevin Timson:

● "You never step in the same river twice—every business transition is unique."
● "The best valuation is what a willing buyer and a willing seller can agree on."
● "I aim to be a continuity-of-care provider—someone clients can trust across every phase of the journey."

🔗 Conclusion:
Whether you're a business owner nearing retirement or an advisor guiding clients through transitions, this episode delivers essential wisdom on how to plan with clarity, confidence, and the right team beside you.
Connect with Kevin:
Website:  https://www.afslaw.com/attorneys/kevin-timson
With Your Guest Host Peter Florio:
Peter F. Florio, CFP®, CLU®, ChFC®, CExP™, CLTC®, is the Founder and Managing Partner of The Florio Wealth Management Group in Westbury, NY. With nearly 40 years of experience, he provides comprehensive wealth, tax, and financial planning for high-net-worth individuals and business owners across the country.
Connect with Peter:
Website: https://www.floriowmg.com
LinkedIn: https://www.linkedin.com/company/florio-wealth-management-group/
Facebook: https://www.facebook.com/floriowmg
Calendly: https://calendly.com/floriowmg

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Most people obsess over hot stock tips — but what if true financial peace came from planning for what really matters? This episode challenges conventional thinking and offers a new lens on wealth, risk, and legacy.

In this episode of Sterling Insights, Roger sits down with Laura Rehbein, Private Wealth Advisor and Founder of Impavid Wealth Advisors. Together, they explore how to bring clarity and confidence to high-net-worth financial planning, sharing valuable insights and practical tips for listeners. Laura draws from her 30 years of experience to discuss emotional blind spots, legacy planning, digital assets, and the dangers of "bad math", offering actionable advice for affluent professionals and retirees. This episode is a must-listen for advisors, wealth builders, and those navigating complex financial lives, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

● 💼 Planning Is More Than Investing: True wealth management means planning for life events, risks, and what money needs to do for you — not just watching the markets.

● 📚 Why “Throw It in a Pile” Works: Laura’s simple but powerful method helps uncover forgotten accounts, misaligned goals, and missing documents.

● 🧠 Emotions Drive Money Decisions: Even smart, successful people struggle with fear and uncertainty around money — acknowledging that is key to great planning.

● 🐾 Don't Forget the Pets: Estate planning isn't complete without considering pets and digital assets — yes, even your Facebook page.

● ⚖️ Balance Assets for Flexibility: Too much in retirement accounts can cause tax headaches later. Strategic asset location matters.

Quotes from Laura Rehbein:

● “Measure money against the job it needs to do someday — and keep measuring, because life changes.”

● “People think they need investments. What they really need is clarity.”

● “You can have all the money in the world and still have a financial train wreck if you don’t plan beyond the numbers.”

🔗 Conclusion:

If you're still focused only on returns, you're missing the real value of planning. This episode will help you think bigger — and smarter — about wealth.

Connect with Laura:

LinkedIn: https://www.linkedin.com/in/laurarehbein/

LinkedIn: https://www.linkedin.com/company/impavid-wealth-advisors-a-private-wealth-advisory-practice-of-ameriprise-financial-services-llc 

Facebook: https://www.facebook.com/ImpavidWealthAdvisors

Connect with Roger:

Website:  https://www.sterlingfoundations.com

Facebook:  https://www.facebook.com/sterlingfoundations/

Twitter:  https://x.com/SterlingFndMgt?mx=2

LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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Are you a business owner wondering how to build wealth without giving up control of your cash? This episode will change how you think about financing, investing, and navigating economic uncertainty.
In this episode of Sterling Insights, guest host Charles Trakas sits down with M.C. Laubscher, founder and wealth strategist at Producers Wealth. Together, they explore how business owners can use infinite banking to grow and protect their wealth, while maintaining access to capital. M.C. draws from his extensive experience as an investor, entrepreneur, and immigrant success story to discuss the real challenges business owners face—like liquidity, control, and taxes—offering actionable strategies for long-term financial independence.
This episode is a must-listen for entrepreneurs, financial advisors, and business owners, providing both insights and tools to take control of cash flow and create sustainable wealth.

Key Takeaways:
● 💸 Be Your Own Bank: Infinite banking helps business owners keep control of their capital while still getting growth and protection.
● 🔄 Cash Flow Seasons: Every business has high and low seasons—this strategy helps smooth cash flow in “winter” months.
● 🔐 Keep Liquidity & Control: Traditional diversification often locks up money—this approach keeps your money accessible.
● 🧾 Tax Efficiency: Proper structuring with life insurance can unlock tax advantages that boost net worth.
● 💼 Real-World Application: M.C. shares how his clients leverage these tools to fund real estate, business expansion, and personal goals—even during crises like the pandemic.

Quotes from M.C. Laubscher:
● "The IRS code is literally a playbook that tells you how to pay the least amount of taxes—legally."
● "If you don’t understand the rules of the banking system, you’re just a piece on someone else’s board."
● "Infinite banking gave me certainty when everything else collapsed—real estate, oil, even cash flow."
🔗 Conclusion:
Infinite banking isn't just a theory—it’s a practical strategy for business owners who want more control, better tax outcomes, and greater flexibility to scale. If you want to protect and supercharge your assets, this episode is your blueprint.
Connect with M.C.:
Website:  www.getwealthforsure.com
With Your Guest Host Charles Trakas:
Charles Trakas is the President of Trakas Financial, LLC, Senior Wealth Advisor with Redwood Private Wealth, and Founder of Proactive Tax Reductions. For over 26 years, he has helped high-net-worth individuals and business owners grow, protect, and transfer wealth through tax-efficient strategies. A lifelong entrepreneur and financial coach, Charles collaborates with CPAs, attorneys, and advisors to deliver comprehensive planning that minimizes taxes and maximizes long-term financial success.
Connect with Charles:
Website:  https://proactivetaxreductions.com/about-us/ LinkedIn:https://www.linkedin.com/in/businessownertaxreductionadvisor/ Facebook Business:https://www.facebook.com/TrakasFinancial  Facebook Personal:https://www.facebook.com/profile.php?id=100011447285280New boost

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What happens when values and financial advice don’t align? This episode explores how purpose-driven planning can reshape the advisor-client relationship—and why it matters more than ever for high-net-worth families.

In this episode of Sterling Insights, Roger sits down with Darryl Lyons, co-founder of PAX Financial Group and a Certified Financial Planner. Together, they explore purpose-driven financial planning through a Judeo-Christian lens, sharing valuable insights and practical tips for advisors and clients alike. Darryl draws from his extensive experience working with business owners and high-net-worth families to discuss value alignment, charitable giving strategies, and navigating today’s complex economic environment, offering actionable advice for financial professionals and faith-driven investors. This episode is a must-listen for advisors who serve high-net-worth clients and want to lead with purpose, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

● ✝️ Aligning Faith and Finance: Why purpose-driven planning resonates with clients who want their investments to reflect their core values.

● 💼 Ideal Client Profile: How PAX Financial serves business owners with $10M+ net worth, especially those approaching succession.

● 📈 Net Asset Flow as Growth Metric: Why Darryl prefers tracking organic AUM growth over total assets.

● 🎁 Strategic Generosity: How donor-advised funds and thoughtful giving strategies can help clients give meaningfully—and tax-efficiently.

● 🧩 Navigating ESG & Proxy Voting: A candid look at how ESG investing intersects (and conflicts) with Judeo-Christian values.

Quotes from Darryl Lyons:

● "He didn’t want to wrestle with the why of giving—he wanted someone who already believed in it, and would focus on how to do it well."

● "If you're using the Lord’s name just to garner business, that’s using it in vain—and I take that seriously."

● "We charge a modest fee because people value what they pay for—and we want them to take action."

🔗 Conclusion: Purpose-driven financial planning isn’t just about performance—it’s about trust, alignment, and helping clients live out their values through their wealth.

Connect with Darryl:

Website:  https://paxfinancialgroup.com/

Connect with Roger:

Website:  https://www.sterlingfoundations.com

Facebook:  https://www.facebook.com/sterlingfoundations/

Twitter:  https://x.com/SterlingFndMgt?mx=2

LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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Think tax strategy is just for April? Think again—this episode dives into how proactive planning, multi-state considerations, and personal client relationships can save businesses big and help them scale smarter.

In this episode of Sterling Insights, guest host Seth Krussman sits down with Joseph Witzig, a seasoned CPA and founder of a thriving multi-state advisory firm. Together, they explore the evolving tax and accounting landscape, sharing valuable insights and practical tips for listeners. Joseph draws from a diverse background—ranging from military intelligence to boutique accounting firms—to discuss the real challenges business owners face when navigating complex tax codes and growth. This episode is a must-listen for advisors, CPAs, and business owners, providing both knowledge and tools to navigate this critical but often overlooked subject.

Key Takeaways:

● 🧭 Proactive Planning Pays Off: Why forecasting taxes and financials in advance can make or break a business.
● 🗺️ Multi-State Blind Spots: How hiring remotely or expanding into new states can create unexpected tax liabilities.
● 💼 The S-Corp Decision: A deep dive into whether S-Corp status actually makes sense—and how to know for sure.
● 🤝 Human First, Virtual Second: Why hybrid accounting firms with in-person options are standing out in a remote-first world.
● 🧠 Experience Over Speed: Advice to aspiring CPAs on why waiting and gaining experience is the best foundation for starting your own firm.

Quotes from the Joseph:

● “We started the firm on the idea of being proactive—not just reacting to what already happened.”
● “One employee in another state can trigger tax filing requirements you never planned for.”
● “The balance sheet matters just as much as the P&L—if not more.”
🔗 Conclusion:
This episode highlights the power of proactive strategy, cross-state awareness, and personalized client service—offering a refreshing lens on what modern advisory firms can and should be doing to stay ahead.
Connect with Joseph Witzig:
Website:  https://www.witzigcpa.com/
LinkedIn:  https://www.linkedin.com/company/witzig-cpa?trk=public_profile_experience-group-header
With Your Guest Host Seth Krussman:
Seth Krussman is a seasoned financial advisor and partner at Brayshaw Financial Group, LLC, with over 30 years of experience in entrepreneurship, business development, and wealth management. A Registered Representative and Investment Advisor Representative with Osaic Wealth, Inc., Seth specializes in tax-efficient investment strategies, executive compensation, and succession planning for high-net-worth clients. Based in Hillsboro, Oregon, he is also the nationally recognized co-host of the radio show Money On Tap and an active community leader, husband, and father.
Connect with Seth:
Website:  https://www.brayshawfinancial.com/
Podcast:  https://www.brayshawfinancial.com/money-on-tap
Facebook:  https://www.facebook.com/3Dinvesting/
X:  https://x.com/BFG_LLC/New boost

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Most advisors say they integrate tax and investments — but what does it look like when tax strategy truly leads the planning process? This episode explores that intersection and how it transforms outcomes for high net worth families.

In this episode of Sterling Insights, Roger sits down with Matt Fitzsimmons, Managing Partner at The Watchman Group and a veteran in investment and tax-integrated planning. Together, they explore how forward-looking tax planning changes the way wealth is managed, sharing valuable insights and practical tips for listeners. Matt draws from his extensive experience to discuss challenges like liquidity events, charitable giving, and business exits, offering actionable advice for advisors serving high net worth and ultra-high net worth clients. This episode is a must-listen for RIAs and fiduciaries managing complex client needs, providing both knowledge and tools to navigate this important subject.
Key Takeaways:
● 🧾 Lead with Tax Strategy: Clients rarely ask for investment alpha — they ask for clarity on taxes. Tax-first planning drives real value.
● 💰 Donor-Advised Funds Done Right: Bundling 10 years of giving into one year can lead to massive, tangible tax savings.
● 🏢 Planning Before the Liquidity Event: Donating illiquid assets pre-sale can unlock six-figure tax savings that are otherwise lost.
● 🏘️ Why Real Estate Is Back: Distress in multifamily housing presents rare buying opportunities — if you know where to look.
● 📉 Tax Alpha with Market-Neutral Strategies: Advanced approaches like accelerating capital losses or ordinary loss-generating funds are reshaping how portfolios are managed for the wealthy.
Quotes from Matt Fitzsimmons:
● “Clients don’t walk in asking about private credit — they walk in asking how to save on taxes.”
● “People value a dollar of tax savings more than a dollar of investment gains.”
● “We’re not just building portfolios — we’re building strategies around life events, tax brackets, and long-term outcomes.”

🔗 Conclusion:
Forward-looking tax planning isn’t just an add-on — it’s a competitive advantage for advisors serving high net worth clients.

Connect with Matt:
Website:  https://www.watchmangroup.com/

Connect with Roger:Website:  https://www.sterlingfoundations.comFacebook:  https://www.facebook.com/sterlingfoundations/Twitter:  https://x.com/SterlingFndMgt?mx=2LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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What if the key to explosive growth in your advisory firm isn’t more clients—but fewer of the right ones?

In this episode of Sterling Insights, Roger sits down with Jon Randall, founder of XFA and PhD in Performance Psychology who coaches top financial advisors across the U.S. Together, they explore how financial advisors can unlock scalable growth and profitability by identifying and removing hidden bottlenecks in their practice. Jon draws from decades of hands-on consulting experience to discuss why most advisors get stuck below the million-dollar ceiling—and how to break through it by focusing on revenue per client, team optimization, and ideal client acquisition.

This episode is a must-listen for growth-minded, AUM-based financial advisors who want to scale with intention, maximize profitability, and finally run their firms like CEOs.

Key Takeaways:

● 📈 Revenue per Client Matters: Advisors focused only on AUM miss the bigger picture—optimizing revenue per client is the true lever for growth.

● 🧠 Break the Comfort Habit: Most advisors resist change due to mental conditioning. Identifying this bias is the first step to scaling effectively.

● ⏳ Capacity is Your Real Constraint: Too many clients—especially unprofitable ones—clog growth. Solving this can unlock massive opportunity.

● 💼 Scaling Doesn’t Require a Giant Team: You can double or triple revenue by going deeper with top clients—not always by adding headcount.

● 💸 Profitability ≠ Big Revenue: Even Barron’s Top 100 firms struggle with margins. Smart segmentation and delegation are essential.

Quotes from Jon Randall:

● "It’s way more efficient to light money on fire in the parking lot than to work with unprofitable clients."

● "Advisors hold onto low-revenue clients like a child holds onto a security blanket."

● "Capacity issues aren’t just slowing you down—they’re suffocating your growth."

🔗 Conclusion:

This episode offers a candid, expert look into the silent constraints sabotaging advisory firms—and how to fix them for lasting success.

Connect with Jon:

Website:  https://www.xfa.coach/

LinkedIn: https://www.linkedin.com/in/jonrandallcmc/

LinkedIn:  https://www.linkedin.com/company/xfa-coach/

Facebook:  https://www.facebook.com/XFA.COACH

Instagram:  https://www.instagram.com/xfa.coach

YouTube:  https://www.youtube.com/@xfacoach

Connect with Roger:

Website:  https://www.sterlingfoundations.com

Facebook:  https://www.facebook.com/sterlingfoundations/

Twitter:  https://x.com/SterlingFndMgt?mx=2

LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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Think cost segregation is just for big-time developers? Think again. This episode reveals how one strategy can unlock massive tax savings—even for everyday real estate investors and medical professionals.

In this episode of Sterling Insights, guest host Charles Trakas sits down with David Wiener, CEO of Cash Flow Strategies and one of the top cost segregation experts in the country. Together, they explore how cost segregation, bonus depreciation, and R&D credits can significantly boost cash flow and reduce tax burdens, sharing valuable insights and practical tips for listeners. David draws from his extensive experience helping doctors, dentists, and real estate investors uncover hidden savings, offering actionable advice for financial advisors and high-net-worth clients seeking smarter tax strategies.
This episode is a must-listen for advisors, CPAs, real estate professionals, and investors—providing both knowledge and tools to navigate this powerful (and often misunderstood) strategy.

Key Takeaways:

● 💸 Cost Seg Isn’t Just for Commercial Giants: Even a single-family rental can qualify for this tax strategy.
● 🧱 Break Down the Building: Learn how to reclassify assets for faster depreciation—and bigger deductions.
● 🧾 Bonus Depreciation Is Back (And Permanent): The “Big Beautiful Bill” makes this a golden opportunity for real estate owners.
● 🧠 Avoid DIY Pitfalls: Cheap cost seg studies can cost you more in audits. Engineering-based reports are IRS-recommended.
● 🔬 R&D Credits Expanded: More industries (including IT) can now qualify—and the credits are available upfront.

Quotes from David Wiener:

● “It’s your money—keep more of it.”
● “You wouldn’t price shop for a brain surgeon. Why do it for your taxes?”
● “We’ve done 50,000+ studies and never triggered an audit.”
🔗 Conclusion:
Cost segregation isn’t just a tax tool—it’s a cash flow supercharger. Advisors and investors who understand it can unlock serious financial leverage.
Connect with David:
Website:  https://costsegregation.infoYouTube:  https://youtube.com/cashflowstrategiesincInstagram:  https://www.instagram.com/david.wiener
Connect with Charles Trakas:
Website:  https://proactivetaxreductions.com/about-us/ LinkedIn:https://www.linkedin.com/in/businessownertaxreductionadvisor/ Facebook Business:https://www.facebook.com/TrakasFinancial  Facebook Personal:https://www.facebook.com/profile.php?id=100011447285280

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What if the biggest financial risks you face aren’t while building wealth—but when you start spending it?

In this episode of Sterling Insights, Roger sits down with Erik Brenner, CFP®, President & CEO of Hilltop Wealth and Tax Solutions. Together, they explore the complexities of transitioning from wealth accumulation to wealth distribution, sharing valuable insights and practical strategies for listeners. Erik draws from over 30 years of experience to discuss tax mitigation, retirement pitfalls, the Personal CFO model, and the challenges facing today’s high‑net‑worth families, offering actionable advice for anyone navigating the modern financial landscape. This episode is a must-listen for high‑net‑worth individuals, business owners, physicians, and advisors seeking deeper planning insights, providing both knowledge and tools to make smarter decisions on the way down the financial mountain.

Key Takeaways:

● 💼 Retirement Isn’t What It Used to Be: Today’s retirees face far more complexity—fewer pensions, more choices, and higher stakes.

● 🧭 The “Coming Down the Mountain” Risk: Most financial mistakes happen during the distribution phase, not the accumulation phase.

● 🧾 Tax Mitigation - Tax Planning: Erik explains why minimizing taxes this year—not deferring them—is essential for high-income and high‑net‑worth individuals.

● 🏛️ The Power of the Personal CFO Model: Comprehensive planning that integrates investments, tax, and estate strategy leads to better long-term outcomes.

● 🌅 Secure Act Changes Everything: New laws have reshaped inheritance, RMDs, and Roth strategy—making guidance more important than ever.

Quotes from Erik Brenner:

● “It’s not your parents’ or grandparents’ retirement anymore.”

● “Most deaths in mountain climbing happen on the way down—and financially, it’s no different.”

● “Tax mitigation means reducing tax today and never paying it back—not just kicking it down the road.”

🔗 Conclusion: Navigating wealth today requires more than investment management—it requires a coordinated, strategic Personal CFO guiding every major financial decision.

Connect with Erik:

Website: https://hilltopwealthtax.com/

LinkedIn: https://www.linkedin.com/in/erikbrenner/

LinkedIn:  https://www.linkedin.com/company/hilltopwealthtax/

Facebook: https://www.facebook.com/hilltopwealthtax

Instagram: https://www.instagram.com/hilltopwealthtax/

YouTube: https://www.youtube.com/@HilltopWealthTaxSolutions

Connect with Roger:

Website:  https://www.sterlingfoundations.com

Facebook:  https://www.facebook.com/sterlingfoundations/

Twitter:  https://x.com/SterlingFndMgt?mx=2

LinkedIn:  https://www.linkedin.com/company/sterling-foundation-management-llc/

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70% of family businesses fail to transition successfully — what if the right conversation could change that? Discover how proactive planning, people-first strategies, and a clear roadmap can turn succession chaos into clarity.

In this episode of Sterling Insights, guest host Ray O’Connell sits down with Chuck Cooper the founder of Whitewater Consulting, a seasoned business consultant specializing in HR, succession, and exit planning for family-owned and mid-sized businesses. Together, they explore the hidden pitfalls of business succession, sharing valuable insights and practical tips for listeners. The guest draws from decades of experience to discuss why most succession plans fail, how to navigate emotionally charged family dynamics, and how to build a roadmap that secures both legacy and value.
This episode is a must-listen for business owners, financial advisors, and professionals working with family enterprises, providing both knowledge and tools to navigate this critical stage of business growth and transition.

Key Takeaways:
● 🔄 Succession Is a Process, Not an Event: Business owners should start planning 3–5 years ahead, not 6–12 months before exiting.
● 🧭 Clarity Starts with Conversations: Open, facilitated conversations among family members are key to aligning vision and expectations.
● 💼 Value Is More Than EBITDA: Up to 80% of business value comes from human, structural, customer, and cultural capital — not financial statements.
● 🧠 Advisors Matter: Succession planning requires a trusted team — legal, financial, HR, and coaching professionals all play a role.
● 📚 The Tools Are There — Use Them: The guest’s book and toolkit provide business owners a DIY path or support for guided implementation.

Quotes from the Chuck:
● “70% of business owners we surveyed had no succession or exit plan in place.”
● “Most of your business’s value isn’t on your balance sheet — it’s in your people, your systems, and your relationships.”
● “Succession isn’t the end — it’s the start of a new chapter. The sooner you plan, the better your story ends.”
🔗 Conclusion:
Business owners can’t afford to wait. Whether you're focused on preserving your legacy, protecting your team, or maximizing your exit value, thoughtful succession planning is the bridge between what your business is today — and what it can become.
Connect with Chuck:
Website:  https://whitewaterconsulting.net/
With Your Guest Host Ray O'Connell:
Ray O’Connell, Accredited Investment Fiduciary® (AIF®), is founder and Managing Director of Altus Wealth Strategies, dba Altus Wealth and Tax. Altus Wealth and Tax uses a Proactive and Holistic Planning and Tax / Capital Gains Minimization process backed by a team of 50+ Family Office specialists. We have been in business for over 30 years, located in the Southeast, and work nationally. O’Connell has taught hundreds of advisors the principles of integrating tax planning strategies with investments and insurance. He has presented programs to physician groups, business owners and high net worth. He is also an author.
Connect with Ray:
Email: Ray@AltusWealthAndTax.com
Website:  https://altuswealthstrategies.com/

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Are you overpaying in taxes without even realizing it? Discover how one CPA helps small business owners uncover hidden savings and avoid costly mistakes most accountants overlook.
In this episode of Sterling Insights, guest host Charles Trakas sits down with Parth Mehta, CPA and owner of Parth Mehta CPA Professional Corporation. Together, they explore how proactive tax planning can save small business owners and self-employed professionals thousands, sharing valuable insights and practical tips for listeners. Parth draws from his extensive experience working with real estate investors, medical practices, and creatives in the entertainment industry to discuss common tax pitfalls, overlooked deductions, and strategic entity structures, offering actionable advice for entrepreneurs and high-income solo operators.
This episode is a must-listen for small business owners, independent contractors, and real estate investors, providing both knowledge and tools to navigate smarter tax planning.

Key Takeaways:
● 💼 Strategic Entity Selection: Choosing the right business structure (like an S Corp) can significantly reduce self-employment taxes.
● 🏡 Real Estate Tax Nuances: Real estate partnerships come with specific compliance requirements—getting it wrong can be costly.
● 📉 Bonus Depreciation & Tax Code: Understanding and using bonus depreciation can benefit startups, even before they’re profitable.
● 📊 Beyond Compliance: Tax savings come from planning, not just preparation—your CPA should be advising, not just filing.
● 🔍 Fraud & Ethics in Practice: Working independently allows for higher ethical standards and more client-focused service.

Quotes from Parth Mehta:
● "Tax preparation is not how you save money. It's with the planning and projections that you save on taxes."
● "If your accountant doesn’t give you actual advisory services, you're just paying them to input numbers into a computer."
● "I can charge clients less, pay myself more, and still give them the attention they deserve."
🔗 Conclusion:
Tax savings don’t come from filing on time—they come from planning ahead. Parth’s approach proves that proactive, personalized accounting creates long-term financial wins for small business owners.
Connect with Parth:
Website: https://parthmehtacpa.com/
LinkedIn: https://www.linkedin.com/in/parthmehtacpa/
Connect with Charles:
Website:  https://proactivetaxreductions.com/about-us/ LinkedIn:https://www.linkedin.com/in/businessownertaxreductionadvisor/ Facebook Business:https://www.facebook.com/TrakasFinancial  Facebook Personal:https://www.facebook.com/profile.php?id=100011447285280

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What if everything you thought about financial risk was wrong? Discover how redefining risk could help your high net worth clients achieve more—and sleep better at night.

In this episode of Sterling Insights, Roger sits down with Clark Richard, Co-Founder and CEO of Vineyard Global Advisors. Together, they explore a client-first approach to risk, portfolio design, and long-term planning, sharing valuable insights and practical tips for listeners. Clark draws from his extensive experience building financial businesses and guiding ultra-affluent families to discuss how to align wealth strategy with real-life goals, offering actionable advice for advisors who serve high net worth clients. This episode is a must-listen for financial advisors managing assets under management (AUM), providing both knowledge and tools to navigate planning, risk, and client expectations with greater confidence.

Key Takeaways:

• 📉 Risk Reimagined: True risk isn't volatility—it’s the probability of not achieving your goals. Clark explains how he reframes risk for clients.

• 🧮 Planning-First Philosophy: Start with goals, not products. Clark shows how planning leads investment strategy—not the other way around.

• 💼 Tailored Portfolios: How time-segmented strategies help align liquidity, volatility, and long-term growth in client portfolios.

• 🏛️ Private Market Insights: When and how private credit, private equity, and interval funds fit into high net worth portfolios.

• 🧾 Tax and Estate Integration: Why most financial plans fail to connect taxes, estate planning, and portfolio strategy—and how to fix it.

Quotes from Clark Richard:

• "Volatility is just one measure of risk. We define risk as the probability of not meeting your financial objectives."

• "Structure follows strategy. Without an integrated plan, even good ideas can fail to deliver."

• "It's not what you make. It’s what you keep."

🔗 Conclusion:

This episode challenges traditional thinking and equips advisors with a framework to better serve high net worth clients—by integrating planning, risk management, and wealth strategy into one cohesive approach.

Connect with Clark:

Website:  http://www.vineyardglobaladvisors.com/

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