Do Small Business Like a Big Boss Podcast

By Aisha Massengill

Listen to a podcast, please open Podcast Republic app. Available on Google Play Store and Apple App Store.


Category: Entrepreneurship

Open in Apple Podcasts


Open RSS feed


Open Website


Rate for this podcast

Subscribers: 0
Reviews: 0
Episodes: 24

Description

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.

Episode Date
Why Digital Literacy Is the New Small Business Skill | Do Small Business like a Big Boss
Jul 29, 2026
From Corporate Dropout to 6-Figure CEO: How Shan Thomas Built on Her Own Terms
Jul 22, 2026
How to Know When to Outsource
Jul 15, 2026
Outsmarting the Big Guys: Building a Challenger Brand Agency from Scratch
Jul 09, 2026
From Engineering to Landscaping COO: Recurring Revenue, Smart Hiring & Systems That Scale
Jul 01, 2026
Building Six-Figures Organically: Social Media, Government Contracts & Community
Jun 24, 2026
If You Don't Have a Client Plan, You Have a Time Bomb
May 27, 2026
The Bootstrapped EdTech Playbook: Offshore Teams, DIY PR, and 20K Users
May 20, 2026
Stop Guessing, Start Growing: Marketing Strategy for Small Business
May 13, 2026
How Joy L. King Built Two Businesses on Intuition + Referrals (While in a Chief Role)
May 06, 2026
From Military Service to Mission-Driven Business: How Jordie Kern Built 7 Eagle Group
Apr 22, 2026
From Teacher to Tech CEO: How Stephen Spence Built a Software Company With No Startup Background
Apr 08, 2026
From Groupon Deals to Multiple Business Lines: How One Spa Owner Built Tocar From a Single Room
Apr 01, 2026
Hiring Secrets for Startups: What Every Founder Needs to Know
Mar 25, 2026
Stop Drowning in Tasks — How to Delegate Like a Boss with Tanya Thomas
Mar 11, 2026
Don’t Be a Boss, Be a Leader — Building Partnerships That Change Lives with Gregory Weiss
Feb 25, 2026
Why Your Biggest Security Threat Isn’t Hackers – It’s Your Humans
Feb 11, 2026
The Leadership Skill Nobody Teaches (But Every CEO Needs) | Richard Yep
Feb 04, 2026
From Alcatraz to Budding Wine Dynasty
Jan 28, 2026
Excited and Terrified: The Dual Emotions Every New Leader Must Master
Jan 14, 2026
The Importance of Systems and Coaches as a Business Owner with David Girton of LiveNow Fitness
Jan 07, 2026
From Google Search to Six-Figure Solo Law Firm: Lauren Lester
Jan 01, 2026
From selling candy on the playground to building and selling multiple seven-figure companies
Dec 26, 2025
Why You Should Do Your Small Business Like a Big Boss!
Dec 17, 2025