Do Small Business Like a Big Boss Podcast

Do Small Business Like a Big Boss Podcast

Aisha Massengill

Episodes 18
Avg. Duration 39m
Activity Active
Apple Rating 5.0 (8)
Since Dec 2025
Latest Episode May 2026

Publishing Details

Schedule
Weekly
Format
Episodic
Consistency
67%
Hosting
api.riverside.fm

Contact & Outreach

About This 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.

Podcasting 2.0 Features

transcript

Explore Statistics

Recent Episodes

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

May 27, 2026 33m Transcript

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 realities of growing a consultancy,…

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

May 20, 2026 29m Transcript

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 building an EdTech company from…

Stop Guessing, Start Growing: Marketing Strategy for Small Business

May 13, 2026 40m Transcript

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 businesses can stop wasting money on…

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

May 06, 2026 42m Transcript

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 Coaching, to talk about building…

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

Apr 22, 2026 45m Transcript

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 build and rebuild businesses…

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

Apr 08, 2026 36m Transcript

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 about his unconventional…

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

Apr 01, 2026 47m Transcript

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 with Stephen Conti,…

Hiring Secrets for Startups: What Every Founder Needs to Know

Mar 25, 2026 27m Transcript

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 and CEO of Novo Guild, to…

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

Mar 11, 2026 35m Transcript

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, founder of Team Delegate, to…

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

Feb 25, 2026 39m

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 Partner of Action Staffing…

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

Feb 11, 2026 37m

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, Chief Cybersecurity…

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

Feb 04, 2026 34m

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 with Richard Yep, Vice…

From Alcatraz to Budding Wine Dynasty

Jan 28, 2026 48m

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 Nancy Belle Hansford,…

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

Jan 14, 2026 37m

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 journey from employee to owner of…

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

Jan 09, 2026 37m

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 journey from employee to owner of…

The Importance of Systems and Coaches as a Business Owner with David Girton of LiveNow Fitness

Jan 07, 2026 49m

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with David Girton, founder of LiveNow Fitness, to discuss the importance of having systems and coaches in…

From Google Search to Six-Figure Solo Law Firm: Lauren Lester

Jan 01, 2026 35m

From Google Search to Six-Figure Solo Law Firm: Lauren Lester's Unconventional Path to Work-Life BalancePodcast: Do Small Business Like a Big BossEpisode Description:In this episode of Do Small…

From selling candy on the playground to building and selling multiple seven-figure companies

Dec 26, 2025 43m

Episode Title:From Selling Candy on the Playground to Building and Selling Multiple Seven-Figure CompaniesPodcast:Do Small Business Like a Big Boss🎧 Episode DescriptionIn this episode of Do Small…

Why You Should Do Your Small Business Like a Big Boss!

Dec 17, 2025 8m

Podcast: Do Small Business Like a Big BossEpisode Description:In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at Sedgwick Andrews…

Frequently Asked Questions

How many episodes does Do Small Business Like a Big Boss Podcast have?

Do Small Business Like a Big Boss Podcast has published 18 episodes since December 2025, covering topics in Business, Entrepreneurship.

Is Do Small Business Like a Big Boss Podcast still active?

Do Small Business Like a Big Boss Podcast is currently active with new episodes weekly. Average episode length is 39m.

How do I contact Do Small Business Like a Big Boss Podcast for sponsorship or guest appearances?

Sign up on Grep.FM to access contact details for Do Small Business Like a Big Boss Podcast, including email and social media links.

Similar Podcasts