Do Small Business Like a Big Boss Podcast

by Aisha Massengill

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.

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Latest episodes

Showing 20 · updated from the feed

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

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 found

Jul 29
47 min

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

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 w

Jul 22
42 min

How to Know When to Outsource

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

Jul 15
54 min

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

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

Jul 9
37 min

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

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

Jul 1
29 min

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

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 Founde

Jun 24
47 min

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

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 realit

May 27
33 min

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

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 bui

May 20
29 min

Stop Guessing, Start Growing: Marketing Strategy for Small Business

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 busine

May 13
40 min

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

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 Coachin

May 6
42 min

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

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

Apr 22
45 min

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

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

Apr 8
36 min

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

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 w

Apr 1
47 min

Hiring Secrets for Startups: What Every Founder Needs to Know

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

Mar 25
27 min

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

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, found

Mar 11
35 min

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

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 Partn

Feb 25
39 min

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

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,

Feb 11
37 min

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

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 w

Feb 4
34 min

From Alcatraz to Budding Wine Dynasty

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 Na

Jan 28
48 min

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

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 journ

Jan 14
37 min