Podcasts · Business

Do Small Business Like a Big Boss Podcast

Aisha Massengill

28 episodes

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.

Episodes

  1. Don't Play Small: Brand Voice and Confidence for Founders | Do Small Business like a Big Boss

    · 36 min

    Learn how to find a brand voice that sounds like you, and how to ride the ups and downs of business ownership without panic. Becky Freemal spent 25 years as an Emmy Award-winning broadcast journalist before launching…

  2. PR for Small Business: Why Hyperlocal Beats Forbes

    · 47 min

    In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Nicole Blake Baxter, founder of The Blake Agency, to discuss how small businesses can use public relations (PR) to build…

  3. The $300K Mistake That Taught Him You Can’t Buy Trust

    · 42 min

    In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Marcus Smith, CEO of Cloud Trailz, a Salesforce support, management, and strategy firm, to talk about the systems and…

  4. The No-Code Playbook for First-Time Founders

    · 49 min

    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 Dan Hafner, founder of Dapper No Code, to…

  5. Why Digital Literacy Is the New Small Business Skill | Do Small Business like a Big Boss

    · 47 min

    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…

  6. From Corporate Dropout to 6-Figure CEO: How Shan Thomas Built on Her Own Terms

    · 43 min

    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…

  7. How to Know When to Outsource

    · 54 min

    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…

  8. Outsmarting the Big Guys: Building a Challenger Brand Agency from Scratch

    · 37 min

    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…

  9. From Engineering to Landscaping COO: Recurring Revenue, Smart Hiring & Systems That Scale

    · 29 min

    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…

  10. Building Six-Figures Organically: Social Media, Government Contracts & Community

    · 48 min

    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…

  11. If You Don't Have a Client Plan, You Have a Time Bomb

    · 34 min

    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,…

  12. The Bootstrapped EdTech Playbook: Offshore Teams, DIY PR, and 20K Users

    · 30 min

    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…

  13. Stop Guessing, Start Growing: Marketing Strategy for Small Business

    · 41 min

    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…

  14. How Joy L. King Built Two Businesses on Intuition + Referrals (While in a Chief Role)

    · 42 min

    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,…

  15. From Military Service to Mission-Driven Business: How Jordie Kern Built 7 Eagle Group

    · 45 min

    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…

  16. From Teacher to Tech CEO: How Stephen Spence Built a Software Company With No Startup Background

    · 37 min

    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…

  17. From Groupon Deals to Multiple Business Lines: How One Spa Owner Built Tocar From a Single Room

    · 47 min

    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,…

  18. Hiring Secrets for Startups: What Every Founder Needs to Know

    · 28 min

    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…

  19. Stop Drowning in Tasks — How to Delegate Like a Boss with Tanya Thomas

    · 36 min

    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…

  20. Don’t Be a Boss, Be a Leader — Building Partnerships That Change Lives with Gregory Weiss

    · 40 min

    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…

  21. Why Your Biggest Security Threat Isn’t Hackers – It’s Your Humans

    · 38 min

    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…

  22. The Leadership Skill Nobody Teaches (But Every CEO Needs) | Richard Yep

    · 35 min

    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…

  23. From Alcatraz to Budding Wine Dynasty

    · 49 min

    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…

  24. Excited and Terrified: The Dual Emotions Every New Leader Must Master

    · 37 min

    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…

  25. The Importance of Systems and Coaches as a Business Owner with David Girton of LiveNow Fitness

    · 50 min

    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…

  26. From Google Search to Six-Figure Solo Law Firm: Lauren Lester

    · 35 min

    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…

  27. From selling candy on the playground to building and selling multiple seven-figure companies

    · 43 min

    Episode Title: From Selling Candy on the Playground to Building and Selling Multiple Seven-Figure Companies Podcast: Do Small Business Like a Big Boss 🎧 Episode Description In this episode of Do Small Business Like…

  28. Why You Should Do Your Small Business Like a Big Boss!

    · 8:21

    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 &…

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