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.
Do Small Business Like a Big Boss Podcast
Claim This Podcastby Aisha Massengill
Podcast Overview
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.
Language
🇺🇲
Publishing Since
12/17/2025
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Recent Episodes
May 27, 2026
If You Don't Have a Client Plan, You Have a Time Bomb
Host Aisha Jorge Massengill interviews David Cassel, co-founder and CTO of 4V Services, about building a client acquisition strategy to avoid business risks and achieve sustainable growth.
May 20, 2026
The Bootstrapped EdTech Playbook: Offshore Teams, DIY PR, and 20K Users
Host Aisha Jorge Massengill interviews Regnault Drake Sanders, founder of School Economy Inc., about bootstrapping an EdTech company to 20,000 users through offshore teams and DIY PR.
May 13, 2026
Stop Guessing, Start Growing: Marketing Strategy for Small Business
Host Aisha Jorge Massengill interviews George Ennis, founder of EAG Advertising, about building effective marketing strategies that drive growth for small businesses.
18 total episodes available with 15 transcripts
Recent guests on Do Small Business Like a Big Boss Podcast
Guests from recent episodes — sign up to see every guest that has ever appeared on this show.
David Cassel
Guest
Regnault Drake Sanders
Guest
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Frequently asked questions
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- What is Do Small Business Like a Big Boss Podcast?
- How often does this podcast release new episodes?
This podcast updates daily.
- Where can I listen to this podcast?
This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
Yes, this podcast regularly features guests.
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