Explorez tous les épisodes du podcast Do Small Business Like a Big Boss Podcast

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder of Sedgwick Andrews Legal & Consulting, LLC, sits down with Tonya Thomas, founder of Team Delegate, to discuss the entrepreneurial journey and the crucial skill of delegation.

Tonya shares her experiences transitioning from a solo entrepreneur to leading a successful virtual assistant agency. The conversation touches on the challenges of scaling a business, building trust with clients, and identifying when to hire a virtual assistant (VA) to manage overwhelm. They also discuss the tools and systems that can streamline task management and the value of working with US-based virtual assistants.

• Delegation is a learned skill—and it’s essential for business growth.
• Building trust with clients and VAs is key to a successful working relationship.
• How to know when it’s time to hire a virtual assistant to avoid burnout.
• Tools for effective task management and how they help in scaling a business.
• The importance of US-based virtual assistants and why they are a valuable asset to businesses.

• 00:00 – The entrepreneurial journey begins
• 03:10 – Navigating the early days of business
• 05:54 – Building Team Delegate: From solo to agency
• 09:05 – Transitioning from working in to working on
• 11:52 – Delegation: The art of letting go
• 15:08 – Identifying when to hire a virtual assistant
• 18:03 – Overcoming control issues in delegation
• 20:57 – Tools for effective task management
• 23:54 – Onboarding and building relationships with VAs
• 27:06 – Learning from mistakes and growing
• 30:01 – The value of US-based virtual assistants
• 32:57 – Finding fulfillment in helping others
• 35:58 – Staying grounded in entrepreneurship

• "Delegation is a skill set."
• "Communication is key."
• "Learn from your failures."
• "Identify when to hire a VA to manage overwhelm."
• "Trust is the foundation of client-VA relationships."

Tonya Thomas is the founder of Team Delegate, a virtual assistant agency offering US-based VAs to help businesses scale. Tonya’s entrepreneurial journey began in the early 2000s, and she now leads a growing agency focused on effective delegation, building trust, and supporting business owners as they grow their teams.

Connect with Tonya Thomas:
Website: teamdelegate.com
LinkedIn: linkedin.com/in/tonyathomas

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Build the dream messy, build it scared, just don’t build it small.

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In this episode of Do Small Business Like a Big Boss, host Aisha Massengill, Founder of Sedgwick Andrews Legal & Consulting, LLC, interviews Gregory Weiss, Managing Partner of Action Staffing Group. Gregory shares insights into leadership, hiring, and how the staffing industry is about changing lives—not just filling positions.

They discuss the challenges of navigating COVID-19, the costs of bad hires, and why human connection is irreplaceable in business, even in the age of AI. Gregory highlights how building meaningful partnerships and leading with heart are keys to success.

• Staffing isn’t just about filling positions—it’s about changing lives.
• Why titles don’t matter—team success is what drives business.
• The true cost of a bad hire and how to avoid it.
• Why AI can’t replace human-to-human connection in business.
• Leadership vs. Bossing: What makes a great leader.

• 00:00 – Introduction to Action Staffing Group
• 01:37 – The importance of partnerships in staffing
• 05:06 – Transitioning roles: From CEO to Managing Partner
• 06:20 – Navigating COVID-19
• 07:45 – Common hiring mistakes for small businesses
• 10:03 – Building client relationships
• 13:31 – The role of AI in recruitment
• 16:55 – Managing chaos in staffing
• 19:41 – The human element in business decisions
• 23:19 – Staying focused amidst competition
• 26:23 – Personal motivation and accountability
• 29:16 – The importance of listening in business
• 34:50 – Leadership vs. Bossing: A Philosophy

• "We are in the business of helping people change their lives for the better."
• "Titles don’t mean a thing; it’s about the success of the company."
• "Just pick up the phone and talk to people—that’s how partnerships are built."
• "Sell with your ears, not your mouth."
• "Don’t be a boss, be a leader."
• "AI is hurting businesses because you’re losing human-to-human interaction."

Gregory Weiss is the Managing Partner of Action Staffing Group, a staffing firm focused on changing lives through meaningful employment. Gregory believes in leadership built on accountability, relationships, and understanding that people—not positions—are at the heart of every business.

Connect with Gregory:
LinkedIn: linkedin.com/in/gregory-weiss-2591a935
Website: actionstaffing-group.com

Join Aisha Massengill for her FREE weekly webinar, Make Your Business Official, where she helps small business owners navigate the legal steps to build a legit, protected, and profitable business.
👉 Register here: Make Your Business Official

For legal tips and business strategies, follow us here:
👉 https://linktr.ee/Sedgwick_Andrews_LC

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder of Sedgwick Andrews Legal & Consulting, LLC, sits down with Carter Schoenberg, Chief Cybersecurity Officer at SoundWay Consulting, Inc., to discuss the human side of cybersecurity—why it’s the biggest threat and how small businesses can protect themselves.

Carter brings decades of cybersecurity experience, sharing insights into the human element’s role in organizational security. He also discusses the impact of AI on cybersecurity, the importance of HR and IT collaboration, and why cybersecurity is not just for big companies but for small businesses too.

This conversation highlights real-world lessons every entrepreneur needs to hear to ensure their business stays secure in today’s digital world.

• Cybersecurity is essential for businesses of all sizes: Understand why even small businesses are targets.
• The human element is the weakest link: Why employees must be educated and involved in protecting sensitive data.
• Best practices for employee onboarding and offboarding: Protect your business during employee transitions.
• The impact of AI on cybersecurity: How artificial intelligence is reshaping the security landscape.
• Balancing security with business growth: How to ensure security doesn't slow down your momentum.

• 00:00 – “The human is the weakest link” – Opening discussion on the human factor in cybersecurity
• 04:55 – The importance of cybersecurity for small businesses
• 12:04 – The human element in cybersecurity
• 20:06 – Best practices for employee offboarding
• 25:04 – Balancing security with growth
• 34:00 – The impact of AI on cybersecurity
• 38:59 – Final thoughts on small business success

Carter Schoenberg is the Chief Cybersecurity Officer at SoundWay Consulting, Inc., with decades of experience in cybersecurity and risk management. Carter focuses on the critical role of human behavior in securing digital infrastructures for businesses of all sizes.

Connect with Carter Schoenberg:
LinkedIn: linkedin.com/in/carter-schoenberg-5122011
Website: soundwayconsulting.com

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
👉 Register here: Make Your Business Official

👉 Grab your FREE Legal Guide at:
Sedgwick Andrews Legal & Consulting - Where Value and Experience Intersect

Follow us for legal tips, business strategy, and boss-level motivation:
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Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, subscribe, download, and share with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Richard Yep, Vice President of Vetted Solutions, to talk about the real challenges of leadership—especially the difficult transition from being someone’s peer to becoming their boss.

Richard brings decades of leadership experience from nonprofit organizations and executive search, sharing hard-earned insights on building inclusive cultures, hiring the right people, and making values-based decisions even when they come at a cost. This conversation explores what worked, what didn’t, and what every entrepreneur, CEO, and emerging leader needs to hear as they grow their organization.

• How to navigate the awkward but essential transition from peer to boss without losing trust
• Why hiring for passion over perfect qualifications attracts the right talent to small businesses
• How to balance finances with growth—and why patience often matters more than speed
• How inclusive leadership improves decision-making and organizational effectiveness
• When to delegate, how to let go, and why listening is a leadership superpower
• The real cost of values-based decisions—and why they define organizational integrity
• Practical advice for entrepreneurs preparing to scale

• 00:00 – Introduction
• 02:54 – Navigating the challenges of leadership
• 05:53 – Hiring and attracting talent in small businesses
• 08:54 – Balancing finances and growth
• 11:55 – Common challenges for CEOs and nonprofit leaders
• 14:53 – The importance of communication and inclusivity
• 17:47 – Delegation and letting go
• 20:35 – Values-based decision making
• 23:35 – Building an inclusive culture
• 26:39 – Pivots and new ventures
• 29:24 – Advice for entrepreneurs
• 32:36 – Conclusion and resources

Richard Yep is the Vice President of Vetted Solutions, bringing decades of leadership experience from nonprofit organizations and executive search. He specializes in helping organizations navigate leadership transitions, build inclusive cultures, and make strategic decisions that align with core values.

Connect with Richard Yep:
LinkedIn: https://linkedin.com/in/richardyep

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
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In this episode of Do Small Business Like a Big Boss, host Aisha Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Nancy Belle Hansford, Founder of Watkinsville Wine, to talk about how she turned a passion discovered at 19 into a thriving winery business.

Nancy shares her inspiring journey from making wine in her parents’ house during the COVID quarantine to founding a federally licensed farm winery. She talks about navigating complex alcohol regulations, turning wine-making failures into new product lines, and balancing a full-time job with running a 24/7 passion. This conversation is a masterclass on how to start small, think big, and build a business that funds your passion without burning you out.

• Starting Young and Asking for Help: How Nancy learned to make wine with zero formal training, and why attending a dry college helped her business
• Navigating Legal and Regulatory Challenges: Decoding federal alcohol licensing and finding loopholes to launch a winery in a dry county
• Turning Mistakes Into Revenue Streams: How Nancy’s early wine failures led to profitable new product lines
• Building a Sustainable Business Model: How Nancy scaled her winery while keeping her passion and paycheck separate to prevent burnout
• Balancing Full-Time Work with a 24/7 Passion: Setting boundaries and making use of simple tools to manage both business and full-time work
• Redefining Success on Your Own Terms: Why Nancy defines success as loving what you do—and not just making money

• 00:00 – Introduction
• 03:23–03:58 – How Nancy learned to make wine with no formal background
• 10:01–10:28 – Cold-calling government officials to get wine-making approval
• 25:10–25:45 – How mistakes became new revenue streams, like pineapple-grapefruit wine
• 48:22 – Wrap-up & Calls to Action

Nancy Belle Hansford is the founder of Watkinsville Wine, a federally licensed farm winery. Starting her wine-making journey at just 19 during the COVID quarantine, Nancy has since grown her business while working full-time as a project manager in tech. She is passionate about creating quality wines, navigating complex legalities, and building a business that allows her to follow her passion without sacrificing her well-being.

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Karen Murphy, President of FBM Integrated Marketing, to discuss her journey from employee to owner of a 35-year-old B2B marketing agency. Karen shares what it’s really like stepping into leadership—feeling both excited and terrified—while navigating mentorship, remote work, and high-level decision-making. This conversation dives into building strong processes, simplifying complex marketing challenges, maintaining work-life balance, and leading with confidence in a women-owned business.

🎧 What You’ll Learn in This Episode:

• You don’t have to start from scratch to build something extraordinary
• Why leadership often feels both exciting and terrifying
• The power of mentorship in personal and professional growth
• How remote work has changed collaboration and leadership
• Why strong processes are essential for managing complex projects
• How to achieve work-life balance through trust and flexibility
• The value of women-owned business certifications
• Why a research-minded approach leads to better client outcomes
• How to simplify complex marketing challenges
• Advice for aspiring leaders facing tough decisions

⏱️ Episode Timestamps:

• 5:40-6:07– The importance of mentorship in leadership
• 23:02 - 25:15 – Research-minded approach to client work
• 34:07-34:34 – Doing small business like a big boss

👤 About the Guest:
Karen Murphy is the President of FBM Integrated Marketing, a B2B marketing and branding agency. She leads with a research-driven mindset, a passion for mentorship, and a commitment to simplifying complex marketing challenges for clients.

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof with confidence.
👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with David Girton, founder of LiveNow Fitness, to discuss the importance of having systems and coaches in place as a business owner. David shares his journey from working a corporate IT job to becoming a successful fitness coach and entrepreneur. He opens up about the hard lessons learned while transitioning from personal training to running a business and why many entrepreneurs struggle when they don’t treat their business like a real operation.

This conversation highlights the power of mentorship, networking, and understanding your value—along with the role mental health and resilience play in long-term entrepreneurial success.

🎧 What You’ll Learn in This Episode:

• Why passion alone isn’t enough to build a successful business
• The biggest mistakes entrepreneurs make when they don’t have systems
• Why getting a business coach early can save years of frustration
• How to transition from being a service provider to a business owner
• The importance of knowing your value and standing by it
• How networking and coaching accelerate growth
• Why mental health and resilience matter in entrepreneurship
• Lessons learned from “doing it the hard way”

⏱️ Episode Timestamps:

• 25:17–25:58 — “We didn’t know how to run a business and learned too many hard lessons”
• 24:21–24:44 / 23:55 — Extended Clip: Get a business coach
• 10:04–11:13 — Know your value and stand by it

👤 About the Guest:
David Girton is the founder of LiveNow Fitness, a health and fitness business offering bootcamp-style training focused on strength, accountability, and sustainable results. David helps clients and fellow entrepreneurs build discipline, confidence, and structure—both inside and outside the gym.

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof with confidence.
👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

From Google Search to Six-Figure Solo Law Firm: Lauren Lester's Unconventional Path to Work-Life Balance
Podcast: Do Small Business Like a Big Boss

Episode Description:
In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Lauren Lester of Lester Law, a solo legal practitioner who built a thriving six-figure law firm in Denver, Colorado—without sacrificing her personal life. Lauren shares her unconventional journey from a surprising Google search that revealed her true career path to launching her own firm straight out of law school, despite being told it couldn’t be done.

Lauren opens up about the pivotal life moment that pushed her to implement radical boundaries in her practice, including her now-famous “no Fridays” rule. She explains how setting firm boundaries not only transformed her work-life balance but also attracted ideal clients who respect her values. The conversation also explores how Lauren leverages legal tech and automation, makes strategic business pivots, and has expanded into coaching other attorneys.

This episode is packed with practical wisdom for small business owners, solo entrepreneurs, and legal professionals who want to build a purpose-driven business without burnout.

🎧 What You’ll Learn in This Episode:

• How to uncover your true career path and act on unexpected opportunities
• What it really takes to launch a solo law firm and bet on yourself
• Why setting strong work-life boundaries can actually attract better clients
• How Lauren’s “no Fridays” rule reshaped her business and personal life
• Ways to leverage automation and legal technology to increase efficiency
• When and how to make strategic pivots as your values evolve
• Business resources that support sustainable growth, including Profit First and the StoryBrand framework

⏱️ Episode Timestamps:

• 15:07-15:25 (Boss) 
• 18:34-19:06 (Boundaries) 
• 30:22-30:32 (Taking the leap)

👤 About the Guest:
Lauren Lester is the founder of Lester Law, a solo law firm based in Denver, Colorado. She helps clients through a streamlined, values-driven legal practice and now coaches other attorneys on building sustainable firms with strong boundaries and systems.

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof with confidence.
👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

Episode Title:
From Selling Candy on the Playground to Building and Selling Multiple Seven-Figure Companies

Podcast:
Do Small Business Like a Big Boss

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Cheryl Perez, a seasoned entrepreneur and business coach, to talk about what it truly takes to scale a business from scratch.

Cheryl shares her journey from corporate employee to building and selling multiple seven-figure companies, breaking down the mindset shifts, systems, and resilience required to grow sustainably. This conversation covers the real-life lessons behind building a business from the ground up—what worked, what didn’t, and what every aspiring entrepreneur needs to hear.

• The difference between working IN your business versus ON your business—and why both are required to scale
• How to know when it’s time to hire your first team member (even when the numbers feel scary)
• Why lead generation systems are the most overlooked investment for new entrepreneurs
• How Cheryl uses a six-step meditation practice to make million-dollar decisions without burnout

• Guest introduction: Cheryl Perez
• 06:35 – Knowing when you’re truly “done” with playing small
• 27:59 – Why capacity limits revenue
• 38:57 – Stepping into Big Boss energy

Cheryl Perez is a seasoned entrepreneur and business coach who has built and sold multiple seven-figure companies. Through her coaching and educational services, she helps entrepreneurs transition from corporate careers, build scalable systems, and create freedom-driven businesses rooted in clarity, preparation, and resilience.

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

Podcast: Do Small Business Like a Big Boss

Episode Description:

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, breaks down her journey from the basketball courts of the Bronx to becoming a successful entrepreneur and attorney.

Aisha emphasizes the importance of claiming your space in business, having the right mindset, and treating your business with the seriousness it deserves. This conversation dives into the challenges faced by small business owners and the need for legal and strategic guidance to build a sustainable business. The podcast aims to empower entrepreneurs with real stories, insights, and practical advice to help them grow their businesses confidently.

🎧 What You’ll Learn in This Episode:

• Claim your spot in business like you did on the court.
• Your mentality is crucial for success in business.
• Stop treating your business like a side hustle.

• Big businesses have systems; so should you.

• You can't build an empire on a shaky foundation.

• Real success stories come from perseverance and learning.

• Legal guidance is essential for small businesses.

• Confidence is key to claiming opportunities.

• Think bigger and act with purpose.

• Your business journey is unique; embrace it.
  

⏱️ Episode Timestamps:

[00:00] – Guest introduction: Aisha Massengill

[02:55] – The 'I Got Next' Mentality in Business

[05:50] – Building a Business Like a Big Boss Businesses

👤 About the Guest:

Aisha Massengill is the founder of Sedgwick Andrews Legal & Consulting, LLC.

Connect with Aisha Massengill:

• Instagram: https://www.instagram.com/sedgwickandrews/
• LinkedIn: https://www.linkedin.com/in/aisha-jorge-massengill-shrm-scp-95bbba4/overlay/about-this-profile/
• Website: https://sedgwickandrews.com/

🚀 Ready to Make Your Business Official?

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at: https://www.topemployermistakes.com

🔗 Stay Connected with Sedgwick Andrews:

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:

Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Massengill, Founder of Sedgwick Andrews Legal & Consulting, LLC, sits down with Bala Vishwanath, Founder and CEO of Novo Guild, to break down what it really takes to hire the right people in a startup.

Bala shares lessons from decades in entrepreneurship—from early startup failures to building a high-demand recruiting firm serving venture-backed companies. They discuss why hiring is harder than most founders expect, what makes a great early-stage hire, and how Lean principles and systems can improve hiring outcomes without losing the human element.

This conversation also explores the growing importance of go-to-market (GTM) talent and how immigration trends are impacting today’s tech talent pipeline.

• Why hiring is harder than most founders expect—and why great hires still fail
• What GTM talent is and why it’s critical for early-stage startups
• How to apply Lean principles and structured systems to hiring
• The key traits that predict success in startup environments
• How immigration trends are shaping the tech talent market

• 00:00 – Introduction & Novo Guild overview
• 01:08 – What GTM talent means
• 03:53 – Scaling a nonprofit globally
• 06:02 – From platform idea to recruiting firm
• 07:34 – Why hiring is harder than expected
• 10:46 – Building credibility with clients
• 12:20 – Applying Lean principles to hiring
• 17:29 – Using the scientific method in hiring
• 19:03 – Traits of successful startup hires
• 21:06 – Immigration and talent supply
• 23:04 – Work-life balance as a founder
• 24:13 – What “Big Boss” means to Bala

Bala Vishwanath is the Founder and CEO of Novo Guild, a talent firm helping venture-backed startups hire top engineering and go-to-market talent across the US and India. He previously founded United Prosperity, a nonprofit supporting small businesses through crowdsourced loan guarantees.

Connect with Bala Vishwanath:
Website: https://novoguild.com
Email: bala@novoguild.com
LinkedIn: Search “Bala Vishwanath”

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
👉 https://www.igotnext.co/training

👉 Grab your FREE Legal Guide:
https://www.topemployermistakes.com

👉 https://linktr.ee/Sedgwick_Andrews_LC

Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, subscribe, download, and share it with another boss who needs to hear it. 🎧

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Jordie Kern, founder of 7 Eagle Group, to explore what it really takes to build and rebuild businesses from the ground up—seven times over.

Jordie shares his 35-year entrepreneurial journey, the mindset behind mission-driven business, and how a simple one-minute video is transforming how military veterans connect with meaningful careers.

This conversation dives deep into resilience, purpose, and practical business strategy, especially for founders building with limited resources but big vision.

🎧 What You’ll Learn in This Episode:

• How Jordie turned a mission to serve veterans into a 30-person recruiting company
• What the SkillBridge program is and how it supports both veterans and employers
• Why the traditional resume model is becoming outdated
• The most important hire to make when scaling a business
• How to think about funding without giving up equity
• Morning routines and time-blocking strategies from a serial entrepreneur
• Why your first business should be designed to fail safely and teach quickly

⏱️ Episode Timestamps:

• 00:04 – Welcome & intro to Jordie Kern and 7 Eagle Group
• 00:49 – Growing up as the son of a WWII Army veteran
• 04:21 – Early entrepreneurial ventures and working with the Clemente family
• 07:23 – The moment Jordie started 7 Eagle Group
• 10:06 – The reality of building the business from scratch
• 12:48 – How the SkillBridge program works
• 23:50 – The one-minute veteran video and why it works
• 30:15 – Scaling a remote team of 30+
• 34:50 – Bootstrapping vs. investors
• 36:35 – Systems, delegation, and protecting your genius zone
• 43:50 – Advice for mission-driven entrepreneurs
• 46:42 – What “Do Small Business Like a Big Boss” means to Jordie

👤 About the Guest:
Jordie Kern is the founder of 7 Eagle Group, a mission-driven talent platform based in Amherst, Massachusetts that connects military veterans and transitioning service members with meaningful civilian careers. With over 35 years of entrepreneurship experience and seven businesses built, Jordie has grown 7 Eagle Group into a fully remote team serving 125+ SkillBridge participants daily through its career academy. The company partners with major organizations including Amazon, the Kansas City Chiefs, American Airlines, and Jack Daniel’s.

Connect with Jordie:
Website: 7eagle.com
Email: jk@7eagle.com

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Stephen Spence, Managing Director and Co-Owner of Project MAPIT, to talk about his unconventional journey from a 20-year career in special education to building a thriving software company.

Stephen shares how a chance opportunity with a former student led him into the world of startups—without formal business training, funding, or a clear roadmap. From surviving on $37,000 in his first year to cold-walking contractor offices with zero sales experience, to now co-owning a company competing with teams 25x their size, Stephen breaks down the real lessons behind resilience, leadership, and growth.

🎧 What You’ll Learn in This Episode:

• How to keep going when you're left alone in a business and everything is on the line
• Why cold outreach often fails—and what actually works for lead generation
• How radical transparency builds trust and drives revenue
• Why you should master roles before delegating them
• What EBITDA is and why it matters for long-term business value
• How systems, tools, and AI support growth in modern businesses
• The mindset needed to handle rejection and stay in the game
  

⏱️ Episode Timestamps:

• 00:25 – Welcome & What is Project MAPIT
• 02:47 – From teacher to tech startup: Stephen's origin story
• 04:30 – When the founder left and Stephen stayed in the fight
• 07:24 – The family decision and support system
• 10:50 – Wearing every hat in the early years
• 13:30 – Lead generation: what worked and what didn’t
• 16:05 – Handling rejection in sales
• 18:00 – Learning roles before delegating
• 21:34 – Buying out a founder
• 23:53 – Understanding EBITDA
• 25:45 – Systems, tools, and AI
• 31:30 – AI in small business
• 33:06 – Advice for entrepreneurs
• 36:35 – What “Do Small Business Like a Big Boss” means to Stephen
• 38:30 – Where to find Stephen
  

👤 About the Guest:
Stephen Spence is the Managing Director and Co-Owner of Project MAPIT, an all-in-one mapping, reputation, and sales platform for contractors in the home services industry. A former special education teacher and coach, Stephen transitioned into entrepreneurship in his 40s and helped scale Project MAPIT into a competitive software company serving hundreds of clients.

Connect with Stephen:
Website: projectmapit.com
LinkedIn: Stephen Spence

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof with confidence.

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🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
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Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Stephen Conti, Founder and CEO of Tocar Spa, Tocar Sport, and Tocar Corporate Wellness. Stephen shares the remarkable story of how he went from running a small spa with Groupon deals to managing a multi-division wellness business in Howard County, Maryland. He reveals the real-life challenges, wins, and valuable lessons from his entrepreneurial journey, offering insights every aspiring entrepreneur can learn from.

🎧 What You’ll Learn in This Episode:

How Stephen transitioned from a marketing career to owning a thriving wellness business

The ups and downs of using Groupon as a launch strategy and what he would do differently

The importance of word-of-mouth referrals and leveraging networking through the Chamber of Commerce

How the Goldman Sachs 10,000 Small Businesses program helped accelerate his growth

The importance of hiring for cultural fit in a service-based business

How to scale a business without losing loyal clients, including transitioning them to other providers

⏱️ Episode Timestamps:

00:00 – Introduction

01:27 – Stephen’s life before Tocar Spa

07:17 – The side hustle: working at a massage franchise

09:27 – Early days of Tocar: no systems, just Groupon

11:20 – Networking: word-of-mouth & social media

14:47 – SCORE, Goldman Sachs, and finding the right CPA

17:18 – Funding the business and bootstrapping

18:35 – Identifying the revenue ceiling and scaling

20:27 – Hiring for culture fit

23:45 – Transitioning clients and leadership layers

32:40 – AI & robotic massage tech

40:35 – Advice to his younger self

45:14 – What Do Small Business Like a Big Boss means to Stephen

👤 About the Guest:

Stephen Conti is the Founder and CEO of Tocar Spa, Tocar Sport, and the newly launched Tocar Corporate Wellness, all located in the Columbia, Maryland area. Starting from a single treatment room and Groupon deals, Stephen has grown Tocar into a multi-division wellness company with 20+ team members across three business lines. He is also the creator of the Healing for Healers program, which provides free massages to caregivers of individuals with Alzheimer's, Parkinson's, and dementia.

Connect with Stephen:

Website: www.tocarspa.com

Location: 10630 Little Patuxent Parkway, Columbia, MD (by the mall) | Appointment only

🚀 Ready to Make Your Business Official?

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: Make Your Business Official

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Sedgwick Andrews Legal & Consulting

🔗 Stay Connected with Sedgwick Andrews:

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

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Podcast Mantra:

Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Joy L. King, founder of Lifestyles by Joy and Sweet Life Business Coaching, to talk about building intuitive, referral-based businesses while balancing a high-level executive role.

This conversation covers the real-life lessons behind starting messy, trusting your instincts, and creating a business rooted in relationships—what worked, what didn’t, and what every aspiring entrepreneur needs to hear.

🎧 What You’ll Learn in This Episode:

• How to stop chasing money and start building through relationships
• The “repeatable value” concept every founder must define before scaling
• How to protect and maintain your business while stepping into a corporate role
• Why mindset and self-worth are the biggest blockers to growth
• What to focus on in your first 30 days before investing in branding or assets

⏱️ Episode Timestamps:

• 00:00 – Introduction
• 00:46 – Guest introduction: Joy L. King
• 02:05 – Launching during the pandemic
• 06:29 – Turning design into therapy and purpose
• 09:21 – Building through referrals
• 11:42 – “All money ain’t good money”
• 17:34 – When chasing money backfires
• 24:14 – Tools and systems Joy uses
• 27:00 – Negotiating an executive role while keeping her businesses
• 33:31 – The #1 mindset block
• 38:15 – The first 30 days as a founder
• 44:14 – What “Big Boss” means

👤 About the Guest:
Joy L. King is a lifestyle architect, business coach, and executive. She is the founder of Lifestyles by Joy, a referral-based interior design firm, and Sweet Life Business Coaching, where she helps entrepreneurs define repeatable value and scale with intention. She also serves as a Chief at NCAN (National College Attainment Network), leading strategy and operations.

🔗 Connect with Joy:
lifestylesbyjoy.com
sweetlifebusinesscoaching.com
LinkedIn — linkedin.com/in/joyking912

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
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Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

 In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with George Ennis, founder of EAG Advertising, to talk about how small businesses can stop wasting money on marketing that doesn’t work and start building strategies that actually drive growth.

This conversation breaks down the biggest mistakes business owners make online, how to maximize a limited marketing budget, and why relationships—not just ad spend—are the real key to long-term business success.

🎧 What You’ll Learn in This Episode:

• How to audit your digital footprint and uncover hidden marketing issues
• The right way to calculate and prioritize your marketing budget
• Why pay-per-click advertising may not be the best move for small businesses
• The “presearch” method for building authentic LinkedIn relationships
• How small businesses can compete with bigger brands strategically
  

⏱️ Episode Timestamps:

• 00:01 – Welcome and guest introduction
• 00:52 – Twin dad life and George’s personal journey
• 01:53 – From corporate America to entrepreneurship
• 03:07 – Launching EAG Advertising
• 06:18 – The importance of niching down
• 08:59 – Building relationships that drive business
• 12:04 – LinkedIn outreach and the “presearch” strategy
• 15:54 – Common digital marketing mistakes
• 19:06 – Competing with big brands on a small budget
• 24:04 – Why websites still matter
• 28:37 – Growing and leading a team
• 33:20 – Work-life balance as an entrepreneur
• 37:49 – What “Do Small Business Like a Big Boss” means to George
• 41:20 – Where to connect with George and EAG Advertising
  

👤 About the Guest:
George Ennis is the Founder of EAG Advertising, a full-service marketing and advertising agency specializing in B2B, nonprofit, and complex industries. With more than 20 years of strategic agency experience, George helps small and mid-sized businesses create marketing strategies with big-business impact.

Connect with George:
LinkedIn: E.A.G. Advertising
Website: eagadvertising.com

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.
👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.topemployermistakes.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
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Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.

🎧 If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Regnault Drake Sanders, founder of School Economy Inc., to talk about building an EdTech company from scratch with no outside funding.

Starting with just $2,000 in Amazon gift cards, Regnault built a platform that rewards K-12 students for academic engagement and now serves over 20,000 active students across New York, Atlanta, and Dallas. This conversation dives into validation, partnerships, grassroots growth, AI automation, and what it really takes to build a mission-driven business that also generates sustainable revenue.

🎧 What You’ll Learn in This Episode:

• How to validate a business idea before investors or partners
• Why non-technical founders need a technical ally
• How AI tools like Zapier and N8N streamline operations
• How major partnerships and relationships drive growth
• Building mission-driven revenue with repeatable sponsorships
  

⏱️ Episode Timestamps:
00:02 – Intro & guest welcome
01:25 – Origin of School Economy
03:20 – Mission behind the business
06:52 – How the platform works
09:25 – Referral & growth system
11:25 – Sponsorship ROI model
12:05 – Starting with $2,000
12:58 – Scaling to 20,000 users
16:16 – Building partnerships
17:40 – First 50 users via outreach
20:03 – Tech companies as people businesses
21:04 – Managing offshore dev teams
24:25 – Bootstrapping without VC
26:10 – Scaling with AI automation
27:47 – DIY PR & media coverage
32:08 – “Do Small Business Like a Big Boss”
33:04 – Where to connect

👤 About the Guest:
Regnault Drake Sanders is a serial entrepreneur and EdTech founder based in Atlanta, Georgia. He is the founder of School Economy Inc., a platform that rewards K-12 students for academic achievement with redeemable prizes and incentives. His platform has grown to serve 20,000 active students across multiple cities and has been featured on Fox 5 Atlanta and at Microsoft education events.

Connect with Regnault:
LinkedIn: linkedin.com/in/regnault-drake-sanders-24797310b

Website: schoolconomy.com

🚀 Ready to Make Your Business Official?

👉If you’ll be in Maryland on June 10, 2026, come see

Aisha in Columbia, MD: 

https://www.eventbrite.com/e/1988791451769?aff=oddtdtcreator

 Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

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🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
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Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with David Cassel, co-founder and CTO of 4V Services, to talk about the realities of growing a consultancy, scaling a team, and building a business that doesn’t rely solely on referrals. 

David shares the lessons he learned growing 4V Services from a small operation into a team of 18, the hard decisions that came with scaling back, and why every entrepreneur needs a real client acquisition strategy before growth becomes a problem.

🎧 What You’ll Learn in This Episode:

• How David evaluates business ideas using a 4-category framework
• Why relying only on referrals can become a major business risk
• How to identify skill gaps and decide whether to learn, hire, or outsource
• What it’s like building and running a business with your spouse
• What a fractional CTO does and how it helps growing businesses scale strategically
  

⏱️ Episode Timestamps:

• 00:14 – Welcome & guest introduction
• 00:35 – David’s origin story and launching 4V Services
• 04:06 – The 4-category framework for evaluating business ideas
• 08:56 – Landing early clients through referrals
• 10:21 – Understanding the MarkLogic niche
• 11:37 – Why referrals alone are a “time bomb”
• 16:17 – Scaling back and lessons on focus
• 18:40 – Strategic hiring and organic growth
• 22:28 – The challenge of training clients too well
• 24:35 – Balancing big clients and smaller accounts
• 26:04 – Running a business with your spouse
• 29:44 – The shift into fractional CTO services
• 36:28 – Advice David would give his younger self
• 38:01 – What “Do Small Business Like a Big Boss” means to David
  

👤 About the Guest:
David Cassel is the co-founder and CTO of 4V Services, a consultancy focused on helping enterprise organizations maximize their MarkLogic investments while applying operational strategy to software development. After nearly a decade at MarkLogic, David launched 4V Services with his wife and grew the business organically to a team of 18. He now helps businesses through fractional CTO services, providing executive-level technology leadership without the cost of a full-time hire.

Connect with David:
 

LinkedIn: David Cassel
Website: 4vservices.com

🚀 Ready to Make Your Business Official?
Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:
https://www.smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:
Follow us across all platforms for legal tips, business strategy, and boss-level motivation:
👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.

🎧 If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Doug Bonnell, Owner and COO of True North Landscaping, to talk about his journey from automotive engineer to leading and scaling a successful family-owned landscaping company.

This conversation covers the real-life lessons behind building a sustainable service business, creating recurring revenue, making strategic hires, and implementing systems that support long-term growth.

🎧 What You’ll Learn in This Episode:

Why recurring revenue is the foundation of a stable service-based business

How to decide whether to hire, outsource, or acquire to fill business gaps

The systems and software that transformed operations and job costing

How Doug and his wife successfully work together in the business

What every entrepreneur can learn from the landscaping industry's referral culture

⏱️ Episode Timestamps:

00:00 – Introduction

00:35 – Guest introduction: Doug Bonnell & True North Landscaping

01:17 – From automotive engineer to family business COO

03:03 – Taking the leap from corporate life

05:42 – Learning the business from the ground up

06:57 – Building recurring revenue through maintenance services

09:21 – Why recurring revenue matters

11:12 – Acquiring a competitor and expanding services

12:13 – Build, hire, or buy?

14:31 – Managing seasonality and workforce challenges

20:23 – Work-life balance as a business owner

23:43 – Running a business with your spouse

24:51 – Common mistakes customers make when hiring contractors

29:26 – Systems and technology that drive growth

32:12 – Advice for aspiring entrepreneurs

33:05 – What “Do Small Business Like a Big Boss” means to Doug

33:52 – Where to connect with Doug and True North Landscaping

👤 About the Guest:

Doug Bonnell is the Owner and COO of True North Landscaping, a high-end residential design, build, and maintenance company serving Northern Michigan. After earning an engineering degree from Western Michigan University and spending six years in the automotive industry, Doug joined the family business and has helped grow it into a 50-person operation with multiple service lines, including maintenance, irrigation, fertilization, and snow removal.

Connect with Doug:

LinkedIn: Doug Bonnell

Website: True North Landscaping

🚀 Ready to Make Your Business Official?

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:

📘 Free Guide: www.smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:

Build the dream messy, build it scared, just don’t build it small.

If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it. 🎧

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Myown Holmes, Owner and Senior Strategist of Socially Polished and Founder of The Prism Effect, to talk about building a six-figure business organically while balancing family, a full-time career, and entrepreneurship.

Myown shares how she leveraged social media, strategic relationships, and community-building to grow her business, navigate government contracting opportunities, and create a platform that empowers minority women entrepreneurs.

🎧 What You’ll Learn in This Episode:

How the “Power of One” framework can help you grow without burnout

Why focusing on one platform can outperform trying to be everywhere at once

How to build a referral network and secure early testimonials through strategic partnerships

The government contracting opportunities many small business owners overlook

Why knowing your numbers and building the right advisory team is critical for growth

⏱️ Episode Timestamps:

00:04 – Welcome & guest introduction

01:04 – Building a business while raising a family

03:31 – The realities of building in the margins

07:25 – Knowing when it was time to leave her job

09:22 – Creating a structurally sound business

13:35 – Breaking into government contracting

16:12 – Diversifying revenue vs. stabilizing revenue

17:50 – The “always be marketing” mindset

18:57 – Knowing your numbers and building your dream team

22:38 – Finding the right platform for your audience

23:31 – The Power of One framework

26:04 – Organic marketing vs. paid advertising

31:10 – Building a referral network through bartering

35:59 – Using AI in small business

39:01 – The hardest lessons of entrepreneurship

40:26 – The mission behind The Prism Effect

46:22 – What “Do Small Business Like a Big Boss” means to Myown

48:22 – Where to connect with Myown

👤 About the Guest:

Myown Holmes is the Owner and Senior Strategist of Socially Polished, a boutique digital marketing agency based in Washington, D.C., specializing in social media strategy, personal branding, B2B social selling, and brand management. She is also the Founder of The Prism Effect, a community dedicated to supporting the mindset, wellness, and business growth of minority women entrepreneurs.

Connect with Myown:

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

Website: https://socially-polished.com/

🚀 Ready to Make Your Business Official?

Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence.

👉 Register here: https://www.igotnext.co/training

👉 Grab your FREE Legal Guide at:

https://www.topemployermistakes.com

https://smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:

Build the dream messy, build it scared, just don’t build it small.

Thinking about turning your side project into a nonprofit or small business? Ian Kimble breaks down exactly what to lock in early — starting with the two moves most founders put off too long.

Ian Kimble is the co-founder and executive director of Black Tech Philly, a Philadelphia nonprofit expanding access to tech education, digital literacy, and AI literacy. What started as a conversation with a stranger coding in a coffee shop back in 2019 is now a program running in four Philadelphia schools, hosting city-wide Tech Town Halls, and building a growing community of tech professionals and aspiring entrepreneurs. Aisha and Ian talk through the free legal resources that helped him formalize the organization, the importance of building the right kind of  culture that shaped how his team hires and holds people accountable, and how storytelling — not advertising — became his biggest lead source.

💡 What You'll Learn

• How to find free legal help for 501(c)(3) formation through pro bono lawyer programs like Philly VIP
• Why culture isn't your website's mission statement — it's the worst behavior you're willing to tolerate — and how to set that standard early
• How showing up in person and telling one specific, sticky story about your business turns into inbound leads

• How to balance a full-time job with building your business in the early days without burning out

⏱️ Episode Timestamps

00:02 – Welcome & meet Ian Kimble

00:55 – The coffee shop conversation that started Black Tech Philly

02:20 – What Black Tech Philly does today

05:20 – Is the appetite really there for tech & AI literacy?

09:39 – Deepfakes, media literacy, and “trust but verify”

12:23 – Getting free legal help early through Philly VIP

16:03 – The real definition of company culture

19:39 – How a LinkedIn shoutout sparked momentum

21:15 – Turning story and “being in the field” into inbound leads

28:27 – From political science to insurance sales to code

32:23 – The moment coding became “the thing”

33:53 – Building a sales pipeline for community partnerships

35:48 – Balancing a full-time job while building the org

43:06 – Why the name “Black Tech Philly” was intentional

44:57 – What “Do Small Business Like a Big Boss” means to Ian

46:06 – Where to find Black Tech Philly

🎤 About Our Guest

Ian Kimble is the co-founder and executive director of Black Tech Philly, a Philadelphia-based educational nonprofit founded in spring 2020, focused on expanding access to technology, digital literacy, and AI literacy across the city.

Website: https://blacktechphilly.org

Ian on LinkedIn: linkedin.com/in/iank6

Take the free Small Business Legal Risk Self-Assessment and get clarity before a contract, a lawsuit, or a bad partnership does it for you.

👉 Grab your assessment here: www.smallbizzlegalguide.com

🔗 Stay Connected with Sedgwick Andrews:

Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

👉 https://linktr.ee/Sedgwick_Andrews_LC

Podcast Mantra:

Build the dream messy, build it scared, just don't build it small.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews Legal & Consulting, LLC, sits down with Shan Thomas, founder of Credible Visibility Media, to discuss how she left a six-figure corporate career to build a thriving business on her own terms. Shan shares how she leveraged her corporate experience, developed profitable systems, and created a business that delivers both financial success and work-life balance.

This conversation covers the real-life lessons behind building a business from the ground up—what worked, what didn't, and what every aspiring entrepreneur needs to hear.

🎧 What You'll Learn in This Episode:

How to leverage corporate experience to build credibility as an entrepreneur

The Bullseye Strategy for attracting ideal clients without limiting growth

A pricing framework to confidently raise your rates

How the TAGS Framework helps create a signature offer that stands out

Why your ideal client is often the person you were 5–10 years ago

⏱️ Episode Timestamps:

00:00 – Introduction

00:52 – Guest introduction: Shan Thomas

02:50 – From corporate career to entrepreneurship

08:34 – Overcoming challenges in a male-dominated industry

13:40 – Quitting without a plan and starting a business

19:36 – Faith, fear, and betting on yourself

25:00 – Profit strategy and revenue planning

27:08 – The Bullseye Strategy for client messaging

30:00 – The TAGS Framework

36:28 – Pricing with confidence

39:19 – Building the "10–4 Life"

42:41 – What "Do Small Business Like a Big Boss" means

44:24 – Wrap-up & calls to action

👤 About the Guest:

Shan Thomas is the founder of Credible Visibility Media, where she helps service-based business owners increase profitability through strategic positioning, signature offers, and scalable systems. Drawing from decades of Fortune 500 experience negotiating billion-dollar logistics contracts, Shan brings big-business strategies to small business owners. She is also the founder of Entrepreneur Her, an Atlanta-based community supporting women entrepreneurs.

Connect with Shan: LinkedIn — @shanthomasbiz

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Follow us across all platforms for legal tips, business strategy, and boss-level motivation:

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Podcast Mantra:

Build the dream messy, build it scared, just don't build it small.

If this episode helped you, don't forget to subscribe, download, and share it with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Brad Stevens, founder and CEO of Outsource Access, to talk about knowing when it's time to outsource and how to build a team that helps your business grow.

Brad shares his entrepreneurial journey, the unexpected path that led him to build a 500+ employee offshore staffing company, and the systems, mindset, and metrics that have fueled his rapid growth.

🎧 What You’ll Learn in This Episode:

• The two-question exercise to identify what you should outsource first
• How to view hiring as an investment instead of an expense
• Why Outsource Access serves businesses across 85 industries instead of specializing in one niche
• The key performance indicators Brad uses to measure outsourcing success
• How educational content and referrals helped grow the business without paid advertising
  

⏱️ Episode Timestamps
01:38 – Brad's origin story: renting Micro Machines toys in 4th grade
05:00 – Learning to spot problems worth solving
08:02 – The moment Brad knew entrepreneurship was the path
13:38 – How Brad thinks about building resilience
18:58 – The exploding pen disaster that led to Outsource Access
25:07 – Why Brad built his team in the Philippines
26:18 – Why Outsource Access serves 85 industries instead of niching down
29:49 – Building word-of-mouth marketing through content and education
33:45 – The two-question exercise for knowing what to outsource
40:14 – The 3 KPIs Brad watches most closely
44:27 – Brad's upcoming book, Automate and Delegate
48:38 – What "Do Small Business Like a Big Boss" means to Brad

🎤 About Our Guest
Brad Stevens is the founder and CEO of Outsource Access, an offshore virtual staffing firm he's grown to 500+ employees across 85 industries in just four and a half years. In 2021, Outsource Access was the only outsourcing company to receive Inc. magazine's Best in Business Award for firms making the biggest impact on their communities, industries, and the environment. His book, Automate and Delegate, is releasing soon.

🔗 Stay Connected with Sedgwick Andrews
👉 https://linktr.ee/Sedgwick_Andrews_LC

Want to see how your business stacks up? Download this business self-assessment: www.smallbizzlegalguide.com

Build the dream messy, build it scared, just don’t build it small.
If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it.

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Justin Bajan, Co-Founder and Creative Director of Familiar Creatures, to talk about leaving a six-figure career to build an award-winning independent advertising agency from the ground up.

Justin shares how his team helps challenger brands outsmart larger competitors, the realities of entrepreneurship, and the lessons that helped Familiar Creatures become one of Adweek’s fastest-growing agencies.

🎧 What You’ll Learn in This Episode:

• How Justin transitioned from corporate life to launching his own agency
• The realities of pricing professional services and avoiding undervaluing your work
• How Familiar Creatures evaluates potential clients using its “Smiley Face System”
• Why saying no to the wrong opportunities can accelerate long-term growth
• How small, agile teams can outperform much larger competitors

⏱️ Episode Timestamps:

• 00:03 – Introduction
• 01:10 – Leaving a six-figure salary
• 02:56 – Moving his family to start over
• 03:26 – Why Richmond became home for the business
• 07:09 – Landing the first anchor client
• 09:20 – The financial realities of early entrepreneurship
• 11:58 – Learning while building the business
• 13:52 – Pricing professional services
• 17:22 – Building a reputation over time
• 18:33 – Making decisions as business partners
• 21:47 – The creative process behind successful campaigns
• 26:06 – Scaling the agency from 2 to 10 people
• 29:30 – Choosing the right clients
• 30:23 – The “Smiley Face System” explained
• 33:23 – Why saying no can be the best business decision
• 37:57 – How small teams outperform big agencies
• 41:08 – What “Do Small Business Like a Big Boss” means to Justin
• 43:06 – Where to connect with Justin and Familiar Creatures

👤 About the Guest:
Justin Bajan is the Co-Founder and Creative Director of Familiar Creatures, an independent advertising agency based in Richmond, Virginia. Since launching in 2018, the agency has been recognized as one of Adweek’s 25 fastest-growing agencies and has helped challenger brands like Duke’s Mayonnaise, Crunch Fitness, and Bubba Burger achieve remarkable growth through strategic creative marketing.

Website: familiarcreatures.com
Instagram: @familiarcreatures

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