Do Small Business Like a Big Boss Podcast

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...

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, maki...

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-...

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 th...

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...

 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 market...

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 ro...

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 vete...

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...

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...

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 s...

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 co...

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...

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 expe...

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 leadersh...

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 t...

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-mak...

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 transitioni...

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 solo legal practitioner who built a thriving six-figure law firm in Denver, Colorado—without sacrifi...

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 Sedgwick Andrews Legal & Consulting, LLC , sits down with Cheryl Perez , a seasoned entrepreneur and bu...

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 becoming a successful entrepreneur and attorney. Aisha emphasizes the importance of claiming your space in...