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

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, and the lessons that helped Familiar Creatures become one of Adweek’s fastest-growing agencies. 🎧 What You’ll Learn in This Episode: * How Justin transitioned from corporate life to launching his own agency * The realities of pricing professional services and avoiding undervaluing your work * How Familiar Creatures evaluates potential clients using its “Smiley Face System” * Why saying no to the wrong opportunities can accelerate long-term growth * How small, agile teams can outperform much larger competitors ⏱️ Episode Timestamps: * 00:03 – Introduction * 01:10 – Leaving a six-figure salary * 02:56 – Moving his family to start over * 03:26 – Why Richmond became home for the business * 07:09 – Landing the first anchor client * 09:20 – The financial realities of early entrepreneurship * 11:58 – Learning while building the business * 13:52 – Pricing professional services * 17:22 – Building a reputation over time * 18:33 – Making decisions as business partners * 21:47 – The creative process behind successful campaigns * 26:06 – Scaling the agency from 2 to 10 people * 29:30 – Choosing the right clients * 30:23 – The “Smiley Face System” explained * 33:23 – Why saying no can be the best business decision * 37:57 – How small teams outperform big agencies * 41:08 – What “Do Small Business Like a Big Boss” means to Justin * 43:06 – Where to connect with Justin and Familiar Creatures 👤 About the Guest: Justin Bajan is the Co-Founder and Creative Director of Familiar Creatures, an independent advertising agency based in Richmond, Virginia. Since launching in 2018, the agency has been recognized as one of Adweek’s 25 fastest-growing agencies and has helped challenger brands like Duke’s Mayonnaise, Crunch Fitness, and Bubba Burger achieve remarkable growth through strategic creative marketing. Website: familiarcreatures.com [http://familiarcreatures.com]Instagram: @familiarcreatures Want to see how your business stacks up? Download this business self-assessment: www.smallbizzlegalguide.com [http://www.smallbizzlegalguide.com] Stay Connected with Sedgwick Andrews: 👉 https://linktr.ee/Sedgwick_Andrews_LC [https://linktr.ee/Sedgwick_Andrews_LC] https://linktr.ee/Sedgwick_Andrews_LCBuild the dream messy, build it scared, just don't build it small. If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it. 🎧

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, making strategic hires, and implementing systems that support long-term growth. 🎧 What You’ll Learn in This Episode: Why recurring revenue is the foundation of a stable service-based business How to decide whether to hire, outsource, or acquire to fill business gaps The systems and software that transformed operations and job costing How Doug and his wife successfully work together in the business What every entrepreneur can learn from the landscaping industry's referral culture ⏱️ Episode Timestamps: 00:00 – Introduction 00:35 – Guest introduction: Doug Bonnell & True North Landscaping 01:17 – From automotive engineer to family business COO 03:03 – Taking the leap from corporate life 05:42 – Learning the business from the ground up 06:57 – Building recurring revenue through maintenance services 09:21 – Why recurring revenue matters 11:12 – Acquiring a competitor and expanding services 12:13 – Build, hire, or buy? 14:31 – Managing seasonality and workforce challenges 20:23 – Work-life balance as a business owner 23:43 – Running a business with your spouse 24:51 – Common mistakes customers make when hiring contractors 29:26 – Systems and technology that drive growth 32:12 – Advice for aspiring entrepreneurs 33:05 – What “Do Small Business Like a Big Boss” means to Doug 33:52 – Where to connect with Doug and True North Landscaping 👤 About the Guest: Doug Bonnell is the Owner and COO of True North Landscaping, a high-end residential design, build, and maintenance company serving Northern Michigan. After earning an engineering degree from Western Michigan University and spending six years in the automotive industry, Doug joined the family business and has helped grow it into a 50-person operation with multiple service lines, including maintenance, irrigation, fertilization, and snow removal. Connect with Doug: LinkedIn: Doug Bonnell Website: True North Landscaping 🚀 Ready to Make Your Business Official? Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence. 👉 Register here: https://www.igotnext.co/training [https://www.igotnext.co/training] 👉 Grab your FREE Legal Guide at: 📘 Free Guide: www.smallbizzlegalguide.com [http://www.smallbizzlegalguide.com] 🔗 Stay Connected with Sedgwick Andrews: Follow us across all platforms for legal tips, business strategy, and boss-level motivation: 👉 https://linktr.ee/Sedgwick_Andrews_LC [https://linktr.ee/Sedgwick_Andrews_LC] Podcast Mantra: Build the dream messy, build it scared, just don’t build it small. If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it. 🎧

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-building to grow her business, navigate government contracting opportunities, and create a platform that empowers minority women entrepreneurs. 🎧 What You’ll Learn in This Episode: How the “Power of One” framework can help you grow without burnout Why focusing on one platform can outperform trying to be everywhere at once How to build a referral network and secure early testimonials through strategic partnerships The government contracting opportunities many small business owners overlook Why knowing your numbers and building the right advisory team is critical for growth ⏱️ Episode Timestamps: 00:04 – Welcome & guest introduction 01:04 – Building a business while raising a family 03:31 – The realities of building in the margins 07:25 – Knowing when it was time to leave her job 09:22 – Creating a structurally sound business 13:35 – Breaking into government contracting 16:12 – Diversifying revenue vs. stabilizing revenue 17:50 – The “always be marketing” mindset 18:57 – Knowing your numbers and building your dream team 22:38 – Finding the right platform for your audience 23:31 – The Power of One framework 26:04 – Organic marketing vs. paid advertising 31:10 – Building a referral network through bartering 35:59 – Using AI in small business 39:01 – The hardest lessons of entrepreneurship 40:26 – The mission behind The Prism Effect 46:22 – What “Do Small Business Like a Big Boss” means to Myown 48:22 – Where to connect with Myown 👤 About the Guest: Myown Holmes is the Owner and Senior Strategist of Socially Polished, a boutique digital marketing agency based in Washington, D.C., specializing in social media strategy, personal branding, B2B social selling, and brand management. She is also the Founder of The Prism Effect, a community dedicated to supporting the mindset, wellness, and business growth of minority women entrepreneurs. Connect with Myown: LinkedIn: https://www.linkedin.com/in/myownh/ [https://www.linkedin.com/in/myownh/] Website: https://socially-polished.com/ [https://socially-polished.com/] 🚀 Ready to Make Your Business Official? Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence. 👉 Register here: https://www.igotnext.co/training [https://www.igotnext.co/training] 👉 Grab your FREE Legal Guide at: https://www.topemployermistakes.com [https://www.topemployermistakes.com] https://smallbizzlegalguide.com [https://smallbizzlegalguide.com] 🔗 Stay Connected with Sedgwick Andrews: Follow us across all platforms for legal tips, business strategy, and boss-level motivation: 👉 https://linktr.ee/Sedgwick_Andrews_LC [https://linktr.ee/Sedgwick_Andrews_LC] Podcast Mantra: Build the dream messy, build it scared, just don’t build it small.

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 came with scaling back, and why every entrepreneur needs a real client acquisition strategy before growth becomes a problem. 🎧 What You’ll Learn in This Episode: * How David evaluates business ideas using a 4-category framework * Why relying only on referrals can become a major business risk * How to identify skill gaps and decide whether to learn, hire, or outsource * What it’s like building and running a business with your spouse * What a fractional CTO does and how it helps growing businesses scale strategically ⏱️ Episode Timestamps: * 00:14 – Welcome & guest introduction * 00:35 – David’s origin story and launching 4V Services * 04:06 – The 4-category framework for evaluating business ideas * 08:56 – Landing early clients through referrals * 10:21 – Understanding the MarkLogic niche * 11:37 – Why referrals alone are a “time bomb” * 16:17 – Scaling back and lessons on focus * 18:40 – Strategic hiring and organic growth * 22:28 – The challenge of training clients too well * 24:35 – Balancing big clients and smaller accounts * 26:04 – Running a business with your spouse * 29:44 – The shift into fractional CTO services * 36:28 – Advice David would give his younger self * 38:01 – What “Do Small Business Like a Big Boss” means to David 👤 About the Guest: David Cassel is the co-founder and CTO of 4V Services, a consultancy focused on helping enterprise organizations maximize their MarkLogic investments while applying operational strategy to software development. After nearly a decade at MarkLogic, David launched 4V Services with his wife and grew the business organically to a team of 18. He now helps businesses through fractional CTO services, providing executive-level technology leadership without the cost of a full-time hire. Connect with David:   LinkedIn: David Cassel Website: 4vservices.com [http://4vservices.com] 🚀 Ready to Make Your Business Official? Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence. 👉 Register here: https://www.igotnext.co/training [https://www.igotnext.co/training] 👉 Grab your FREE Legal Guide at: https://www.smallbizzlegalguide.com [https://www.smallbizzlegalguide.com] 🔗 Stay Connected with Sedgwick Andrews: Follow us across all platforms for legal tips, business strategy, and boss-level motivation: 👉 https://linktr.ee/Sedgwick_Andrews_LC [https://linktr.ee/Sedgwick_Andrews_LC] Podcast Mantra: Build the dream messy, build it scared, just don’t build it small. 🎧 If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.

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 across New York, Atlanta, and Dallas. This conversation dives into validation, partnerships, grassroots growth, AI automation, and what it really takes to build a mission-driven business that also generates sustainable revenue. 🎧 What You’ll Learn in This Episode: * How to validate a business idea before investors or partners * Why non-technical founders need a technical ally * How AI tools like Zapier and N8N streamline operations * How major partnerships and relationships drive growth * Building mission-driven revenue with repeatable sponsorships ⏱️ Episode Timestamps: 00:02 – Intro & guest welcome 01:25 – Origin of School Economy 03:20 – Mission behind the business 06:52 – How the platform works 09:25 – Referral & growth system 11:25 – Sponsorship ROI model 12:05 – Starting with $2,000 12:58 – Scaling to 20,000 users 16:16 – Building partnerships 17:40 – First 50 users via outreach 20:03 – Tech companies as people businesses 21:04 – Managing offshore dev teams 24:25 – Bootstrapping without VC 26:10 – Scaling with AI automation 27:47 – DIY PR & media coverage 32:08 – “Do Small Business Like a Big Boss” 33:04 – Where to connect 👤 About the Guest: Regnault Drake Sanders is a serial entrepreneur and EdTech founder based in Atlanta, Georgia. He is the founder of School Economy Inc., a platform that rewards K-12 students for academic achievement with redeemable prizes and incentives. His platform has grown to serve 20,000 active students across multiple cities and has been featured on Fox 5 Atlanta and at Microsoft education events. Connect with Regnault: LinkedIn: linkedin.com/in/regnault-drake-sanders-24797310b [http://linkedin.com/in/regnault-drake-sanders-24797310b] Website: schoolconomy.com [http://schoolconomy.com] 🚀 Ready to Make Your Business Official? 👉If you’ll be in Maryland on June 10, 2026, come see Aisha in Columbia, MD:  https://www.eventbrite.com/e/1988791451769?aff=oddtdtcreator [https://www.eventbrite.com/e/1988791451769?aff=oddtdtcreator]  Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof your business with confidence. 👉 Register here: https://www.igotnext.co/training [https://www.igotnext.co/training] 👉 Grab your FREE Legal Guide at: https://www.smallbizzlegalguide.com [https://www.smallbizzlegalguide.com] 🔗 Stay Connected with Sedgwick Andrews: Follow us across all platforms for legal tips, business strategy, and boss-level motivation: 👉 https://linktr.ee/Sedgwick_Andrews_LC [https://linktr.ee/Sedgwick_Andrews_LC] Podcast Mantra: Build the dream messy, build it scared, just don’t build it small. If this episode helped you, don’t forget to subscribe, download, and share it with another boss who needs to hear it.