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Artwork for Do Small Business Like a Big Boss Podcast

Do Small Business Like a Big Boss Podcast

Aisha Massengill
Entrepreneurship
Action Staffing Group
Project MAPIT
Livenow Fitness
Black Tech Philly
School Economy Inc
Credible Visibility Media
Small Business
Novo Guild
Family Law
Technology
New York, United States
American Counseling Association
Social Media Marketing
4V Services
Leadership
Tocar Spa
Lean Management
Cybersecurity
Watkinsville Wine

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 ... more

PublishesWeeklyEpisodes24Founded8 months ago
Number of ListenersCategories
ManagementBusinessEntrepreneurship

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Artwork for Do Small Business Like a Big Boss Podcast

Latest Episodes

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 founders put off too long.

Ian Kimble is the co-founder and executive director of Bl... more

YouTube

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 Shan Thomas, founder of Credible Visibility Media, to discuss how she left a... more

YouTube

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 when it's time to outsource and how to build a team that helps your business gro... more

YouTube

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 talk about leaving a six-figure career to build an award-winning independent adv... more

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Recent Guests

Ian Kimble
Co-founder and executive director of Black Tech Philly
Black Tech Philly
Episode: Why Digital Literacy Is the New Small Business Skill | Do Small Business like a Big Boss
Shan Thomas
Business strategist and owner of multiple businesses, helps professional service owners get their lives back while making money
Credible Visibility Media (main business)
Episode: From Corporate Dropout to 6-Figure CEO: How Shan Thomas Built on Her Own Terms
Brad Stevens
Founder and CEO of Outsource Access
Outsource Access
Episode: How to Know When to Outsource
Justin Bajan
Co-founder and Creative Director of Familiar Creatures
Familiar Creatures (Advertising Agency)
Episode: Outsmarting the Big Guys: Building a Challenger Brand Agency from Scratch
Doug Bonnell
Owner, True North Landscaping
True North Landscaping
Episode: From Engineering to Landscaping COO: Recurring Revenue, Smart Hiring & Systems That Scale
Myown Holmes
Owner and senior strategist of Socially Polished
Socially Polished
Episode: Building Six-Figures Organically: Social Media, Government Contracts & Community
David Cassel
Co-founder and CTO of 4V Services
4V Services
Episode: If You Don't Have a Client Plan, You Have a Time Bomb
Regnault Drake Sanders
EdTech founder and serial entrepreneur behind School Economy Inc
School Economy Inc
Episode: The Bootstrapped EdTech Playbook: Offshore Teams, DIY PR, and 20K Users
George Ennis
Founder of EAG Advertising, a full-service marketing and advertising agency
EAG Advertising
Episode: Stop Guessing, Start Growing: Marketing Strategy for Small Business

Host

Aisha Jorge Massengill
Host of the show; branding and podcast sponsorship context vary; likely partner at a legal/consulting practice

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#61
United States/Business/Entrepreneurship
Apple Podcasts
#207
United States/Business
Apple Podcasts
#44
Canada/Business/Entrepreneurship
Apple Podcasts
#211
Canada/Business
Apple Podcasts
#17
Norway/Business/Entrepreneurship
Apple Podcasts
#77
Norway/Business

Talking Points

Recent interactions between the hosts and their guests.

Why Digital Literacy Is the New Small Business Skill | Do Small Business like a Big Boss
Q: Why the name Black Tech Philly and how did it influence outreach?
The name was chosen for intentional inclusivity and visibility, signaling a commitment to inclusive tech education from Philadelphia. It helped attract like-minded participants and supporters while remaining searchable and authentic, which in turn supported broader outreach and funding opportunities.
Why Digital Literacy Is the New Small Business Skill | Do Small Business like a Big Boss
Q: What were the early steps to form a 501(c)(3) and establish culture?
They focused on defining a clear scope to avoid overextension, obtaining legal establishment with support from Philly VIP, and then actively cultivating a culture centered on concrete practices and accountability, which proved essential as they scaled and hired the right people.
Why Digital Literacy Is the New Small Business Skill | Do Small Business like a Big Boss
Q: How did the initial coffee-shop conversation spark the creation of Black Tech Philly?
The encounter sparked a shared vision to expand access to technology and education in Philadelphia, leading to the formalization of a nonprofit focused on youth education, career pathways in tech, and community dialogue. The early synergy, values, and complementary viewpoints among the co-founders catalyzed the pivot from a networking concept to an educational program.
From selling candy on the playground to building and selling multiple seven-figure companies
Q: How did you approach the transition plan and when did you decide to go all in?
She created an 18-month transition plan to build side-hustle revenue until she could leap fully, then ultimately decided to go all in when those efforts and client relationships reached a level that could sustain her without the corporate job.
From selling candy on the playground to building and selling multiple seven-figure companies
Q: What inspired you to take the first entrepreneurial step while climbing the corporate ladder?
Hitting a ceiling in the corporate ladder and realizing there was more she could build on her own, plus a long-standing knack for entrepreneurship that she had quietly developed since childhood.

Audience Metrics

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Listeners per Episode
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Frequently Asked Questions About This Podcast

What is This Podcast about and what kind of topics does it cover?

This show focuses on turning small businesses and side hustles into scalable, legally sound operations through practical frameworks, real-world interviews, and what-works guidance. Episodes frequently explore growth strategy, hiring and HR considerations for expanding teams, and risk management from legal and operational angles. Listeners are likely entrepreneurs and managers who want repeatable systems, mentorship from experienced operators, and actionable steps to compete with larger players without sacrificing core values. A notable strength is the consistent emphasis on balancing compliance (employment law, contracts) with growth tactics, plus encouraging stories of perseverance and disciplined execution from diverse business models and... more

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1. The Amy Porterfield Show
2. Aspire with Emma Grede
3. The Martell Method w/ Dan Martell
4. Coaching Real Leaders
5. Body Bags with Joseph Scott Morgan

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this podcast launched 8 months ago and published 24 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on this podcast?

Recent guests on this podcast include:

1. Ian Kimble
2. Shan Thomas
3. Brad Stevens
4. Justin Bajan
5. Doug Bonnell
6. Myown Holmes
7. David Cassel
8. Regnault Drake Sanders

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