REAL AF with Andy Frisella
Andy Frisella
Business
Do Small Business Like a Big Boss Podcast
by Aisha Massengill
Today: #176 in Business on our combined chart.
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| Date | Apple Podcasts |
|---|---|
| Oct 3 | #162 |
About the show
Ready to take your small business from basement startup to Big Boss success?
Welcome to Do Small Business Like a Big Boss! where we prove that with the right strategy, any up and coming business owner can compete with the big guys. Hosted by Aisha Jorge Massengill, founder of Sedgwick Andrews Legal & Consulting, a seasoned employment attorney who's advised large publicly traded companies for over two decades, this podcast is your courtside seat to business transformation.
Just like that fearless 13-year-old girl shouting ""I got next!"" on Bronx basketball courts, successful entrepreneurs don't just wait their turn—they prepare for it. They study the game, assess the competition, and build the skills they need to win when opportunity calls.
What You'll Discover:
Real Success Stories: In-depth interviews with business owners who've successfully scaled from side hustles to legitimate enterprises
Strategic Frameworks: Proven systems and structures that help small businesses compete like industry giants
Legal & HR Insights: Employment law guidance that protects your growing team while fostering company culture
Risk Management for Entrepreneurs: Smart ways to minimize liability while maximizing opportunity
Perfect for:
Entrepreneurs ready to legitimize their side hustles into scalable businesses
Small Business Owners (10-250 employees) seeking strategic growth frameworks
HR Professionals navigating employment challenges in growing companies
Ambitious Leaders who refuse to let limited resources limit their vision
Each episode features candid interviews with business owners and operators who have navigated the challenges of growth, overcome obstacles, and achieved extraordinary success. Whether you’re scaling your team, refining your business model, or developing a winning mindset, this podcast provides the inspiration and guidance you need to build with discipline, confidence, and purpose.
Your turn is coming. Are you ready?
New episodes drop every week because champions don't take days off.
Subscribe now and join thousands of entrepreneurs who refuse to wait on the sidelines. Your business growth journey starts here.
Latest episodes
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The No-Code Playbook for First-Time Founders
September 30, 2026 · 49 minIn 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 Dan Hafner, founder of Dapper No Code, to talk about building a…
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Why Digital Literacy Is the New Small Business Skill | Do Small Business like a Big Boss
July 29, 2026 · 47 minThinking 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…
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From Corporate Dropout to 6-Figure CEO: How Shan Thomas Built on Her Own Terms
July 22, 2026 · 43 minIn 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…
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How to Know When to Outsource
July 15, 2026 · 54 minIn 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…
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Outsmarting the Big Guys: Building a Challenger Brand Agency from Scratch
July 9, 2026 · 37 minIn 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…
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From Engineering to Landscaping COO: Recurring Revenue, Smart Hiring & Systems That Scale
July 1, 2026 · 29 minIn 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…
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Building Six-Figures Organically: Social Media, Government Contracts & Community
June 24, 2026 · 48 minIn 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…
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If You Don't Have a Client Plan, You Have a Time Bomb
May 27, 2026 · 34 minIn 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…