PODCAST · business
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 enterprisesStrategic Frameworks: Proven systems and structures that help small businesses compete like i
Episodes
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The No-Code Playbook for First-Time Founders
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 Dan Hafner, founder of Dapper No Code, to talk about building a successful software business without learning to code or...
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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 founders put off too long. Ian Kimble is the co-founder and executive director of Black Tech Philly, a Philadelphia nonprofit...
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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 with Shan Thomas, founder of Credible Visibility Media, to discuss how she left a six-figure corporate career to build a…
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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 when it's time to outsource and how to build a team that helps your business grow. Brad shares his entrepreneurial journey, the...
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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 talk about leaving a six-figure career to build an award-winning independent advertising agency from the ground up. Justin…
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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 journey from automotive engineer to leading and scaling a successful family-owned landscaping company. This conversation covers...
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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 Founder of The Prism Effect, to talk about building a six-figure business organically while balancing family, a full-time career, and...
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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 realities of growing a consultancy, scaling a team, and building a business that doesn’t rely solely on referrals. David shares the...
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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 building an EdTech company from scratch with no outside funding. Starting with just $2,000 in Amazon gift cards, Regnault built a...
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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 businesses can stop wasting money on marketing that doesn’t work and start building strategies that actually drive growth. This...
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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 Coaching, to talk about building intuitive, referral-based businesses while balancing a high-level executive role. This conversation...
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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 build and rebuild businesses from the ground up—seven times over. Jordie shares his 35-year entrepreneurial journey, the…
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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 about his unconventional journey from a 20-year career in special education to building a thriving software company. Stephen...
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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 with Stephen Conti, Founder and CEO of Tocar Spa, Tocar Sport, and Tocar Corporate Wellness. Stephen shares the remarkable story...
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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 and CEO of Novo Guild, to break down what it really takes to hire the right people in a startup. Bala shares lessons from…
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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, founder of Team Delegate, to discuss the entrepreneurial journey and the crucial skill of delegation. Tonya shares her experiences...
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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 Partner of Action Staffing Group. Gregory shares insights into leadership, hiring, and how the staffing industry is about changing...
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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, Chief Cybersecurity Officer at SoundWay Consulting, Inc., to discuss the human side of cybersecurity—why it’s the biggest…
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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 with Richard Yep, Vice President of Vetted Solutions, to talk about the real challenges of leadership—especially the difficult...
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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 Nancy Belle Hansford, Founder of Watkinsville Wine, to talk about how she turned a passion discovered at 19 into a thriving…
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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 journey from employee to owner of a 35-year-old B2B marketing agency. Karen shares what it’s really like stepping into...
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The Importance of Systems and Coaches as a Business Owner with David Girton of LiveNow Fitness
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 place as a business owner. David shares his journey from working a corporate IT job to becoming a...
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From Google Search to Six-Figure Solo Law Firm: Lauren Lester
From Google Search to Six-Figure Solo Law Firm: Lauren Lester's Unconventional Path to Work-Life Balance Podcast: Do Small Business Like a Big Boss Episode Description: In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Lauren Lester of Lester Law, a...
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From selling candy on the playground to building and selling multiple seven-figure companies
Episode Title: From Selling Candy on the Playground to Building and Selling Multiple Seven-Figure Companies Podcast: Do Small Business Like a Big Boss 🎧 Episode Description In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill, Founder and Principal Attorney at…
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Why You Should Do Your Small Business Like a Big Boss!
Podcast: Do Small Business Like a Big Boss Episode Description: 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, breaks down her journey from the basketball courts of the Bronx to…
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ABOUT THIS SHOW
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 enterprisesStrategic Frameworks: Proven systems and structures that help small businesses compete like i
HOSTED BY
Aisha Massengill
CATEGORIES
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Frequently Asked Questions
How many episodes does Do Small Business Like a Big Boss Podcast have?
Do Small Business Like a Big Boss Podcast currently has 25 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Do Small Business Like a Big Boss Podcast about?
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...
How often does Do Small Business Like a Big Boss Podcast release new episodes?
Do Small Business Like a Big Boss Podcast has 25 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Do Small Business Like a Big Boss Podcast?
You can listen to Do Small Business Like a Big Boss Podcast on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Do Small Business Like a Big Boss Podcast?
Do Small Business Like a Big Boss Podcast is created and hosted by Aisha Massengill.
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