Do Small Business Like a Big Boss Podcast

About Do Small Business Like a Big Boss Podcast

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.

Publisher

Aisha Massengill

Category

business

Language

en

Explicit

No

First episode

17 Dec 2025

Latest episode

14 Oct 2026

Latest episodes

25 of 27 episodes have a transcript.

1. 

   14 Oct 2026TRANSCRIPT

   PR for Small Business: Why Hyperlocal Beats Forbes

   Host Aisha Jorge Massengill interviews Nicole Blake Baxter, founder of The Blake Agency, about leveraging hyperlocal PR for small business growth and credibility.

2. 

   7 Oct 2026TRANSCRIPT

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

   Host Aisha Jorge Massengill interviews Marcus Smith, CEO of Cloud Trailz, about building a subscription business and the costly lesson that trust cannot be bought.

3. 

   30 Sept 2026TRANSCRIPT

   The No-Code Playbook for First-Time Founders

   Host Aisha Jorge Massengill interviews Dan Hafner, founder of Dapper No Code, about building successful software businesses using no-code tools and AI.

Inside a recent episode

PR for Small Business: Why Hyperlocal Beats Forbes

Published 14 Oct 2026 · Transcript excerpt

[…] And it's not just about Forbes because clients think they know where they need to be. But our role as a PR agency is really to show them where they need to be. This is your audience because you might be a small business owner. And I mean, Forbes is just not the place for you. If you're a tech startup and, you know, yeah, Forbes is great and we all like shiny things, but if you are, for example, you know, in the ed tech space, well, maybe you need to be in education week. Maybe you need to be where your core audience is going to see you. And that's going to be more valuable than a Forbes write-up. […]

Who has been a guest on Do Small Business Like a Big Boss Podcast

Names identified in recent episode analyses. Showing up to five guests.

• Nicole Blake Baxter
• Marcus Smith
• Dan Hafner
• Ian Kimble
• Shan Thomas

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

101 ratings

Spotify

5.0 / 5

3 ratings

Contact Do Small Business Like a Big Boss Podcast

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

Questions about Do Small Business Like a Big Boss Podcast