Do Small Business Like a Big Boss Podcast – Details, episodes & analysis

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

Follow us 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.

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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:
👉 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 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:
👉 https://linktr.ee/Sedgwick_Andrews_LC

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.