Do Small Business Like a Big Boss Podcast
Do Small Business Like a Big Boss is a podcast that helps small business owners compete with larger companies. Hosted by employment attorney Aisha Jorge Massengill, it features interviews with successful entrepreneurs and provides strategic frameworks for scaling a business. The show also covers legal and HR insights to protect growing teams and manage risk. Listeners get practical advice on building systems and structures to transform their ventures into legitimate enterprises.
Episodes
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 expanding access to tech education, digital literacy, and AI literacy. What started as a conversation with a s
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 thriving business on her own terms. Shan shares how she leveraged her corporate experience, developed prof
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 unexpected path that led him to build a 500+ employee offshore staffing company, and the systems, minds
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 shares how his team helps challenger brands outsmart larger competitors, the realities of entrepreneurship,
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 the real-life lessons behind building a sustainable service business, creating recurring revenue, makin
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 entrepreneurship.Myown shares how she leveraged social media, strategic relationships, and community-b
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 lessons he learned growing 4V Services from a small operation into a team of 18, the hard decisions that
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 platform that rewards K-12 students for academic engagement and now serves over 20,000 active students a
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 conversation breaks down the biggest mistakes business owners make online, how to maximize a limited marketi
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 covers the real-life lessons behind starting messy, trusting your instincts, and creating a business root
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 mindset behind mission-driven business, and how a simple one-minute video is transforming how military veter
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 shares how a chance opportunity with a former student led him into the world of startups—without formal bu
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 of how he went from running a small spa with Groupon deals to managing a multi-division wellness b
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 decades in entrepreneurship—from early startup failures to building a high-demand recruiting firm serving
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 transitioning from a solo entrepreneur to leading a successful virtual assistant agency. The conversa
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 lives—not just filling positions.They discuss the challenges of navigating COVID-19, the costs of ba
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 threat and how small businesses can protect themselves.Carter brings decades of cybersecurity experience
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 transition from being someone’s peer to becoming their boss.Richard brings decades of leadership exp
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 winery business.Nancy shares her inspiring journey from making wine in her parents’ house during the COV
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 leadership—feeling both excited and terrified—while navigating mentorship, remote work, and high-level decision-maki
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 successful fitness coach and entrepreneur. He opens up about the hard lessons learned while transitionin
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 BalancePodcast: Do Small Business Like a Big BossEpisode 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 solo legal practitioner who built a thriving six-figure law firm in Denver, Colorado—without sacrificing h
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 CompaniesPodcast:Do Small Business Like a Big Boss🎧 Episode DescriptionIn 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 Cheryl Perez, a seasoned entrepreneur and business coa
Why You Should Do Your Small Business Like a Big Boss!
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 Legal & Consulting, LLC, breaks down her journey from the basketball courts of the Bronx to becoming a successful entrepreneur and attorney.Aisha emphasizes the importance of claiming your space in bu
