Do Small Business
LIKE A BIG BOSS!
P O D C A S T
"Stories of resilience and success while building from the ground up"
Welcome to Do Small Business Like a Big Boss : a podcast dedicated to the resilience, discipline, and strategies behind thriving small businesses. Each episode explores real stories of entrepreneurs who built from the ground up, uncovering their challenges, victories, and lessons learned along the way. With insights drawn from big-business strategies and applied to small-business realities, this show provides a roadmap for building smarter, scaling with confidence, and creating lasting success.
We invite you to join us as a featured guest as we share stories and strategies that empower small businesses to think bigger, grow stronger, and build like a boss, one conversation at a time.
Please Book Your Podcast Below
Questions We May Ask!
Origin Story: Tell us about your business or professional journey — how did you get started, and what inspired you to take the leap?
Boss Moment: Looking back, what was a turning point or breakthrough moment that shifted your business from surviving to thriving?
Big-Business Thinking: What’s one “big-business” strategy, system, or mindset you’ve successfully applied to your small business (or your clients’ businesses)?
Biggest Challenge: What’s been one of your toughest challenges as a leader or founder, and how did you navigate through it?
Smart Growth: How do you approach scaling — what’s helped you grow sustainably without losing control or culture?
Expert Edge (for specialists): For experts — what’s a common mistake you see small business owners make in your area of expertise, and how can they fix it?
Resilience Story: Share a moment when things didn’t go as planned — how did you bounce back or pivot?
Systems & Strategy: What tool, process, or principle has made the biggest difference in running your business more efficiently?
Building Like a Boss: When you hear the phrase “Do Small Business Like a Big Boss,” what does that mean to you personally?
Legacy & Lessons: What’s the one lesson or piece of advice you’d want every small business owner listening to take away from your story?
Meet Your Host
Aisha Jorge Massengill
Host, Do Small Business Like a Big Boss
About Our Host - Aisha Jorge Massengill
Aisha Jorge Massengill is a seasoned attorney, entrepreneur, and host of Do Small Business Like a Big Boss. With over two decades of legal experience and a fearless, competitive spirit shaped from her Bronx roots, she brings a bold and practical approach to helping businesses succeed.
Her journey has been dynamic and inspiring—spanning top schools like Phillips Academy, Boston College, and Georgetown Law, to founding Sedgwick Andrews Legal & Consulting, LLC. Today, she provides flexible legal services that empower small businesses to protect themselves and scale with confidence.
Aisha is passionate about equipping entrepreneurs with the tools, strategies, and mindset to think and act like big players. Through her work, podcast, and collaborations, she delivers actionable insights that help business owners unlock their potential and compete at the highest level.
Did You Know This About
Aisha Jorge Massengill?
I was the first person, male or female, in my high school's history, to earn 12 varsity letters. Though many have done it since, I will always be the first!
Want To Connect With
Aisha Jorge Massengill
before your interview?
