From Engineering to Landscaping COO: Recurring Revenue, Smart Hiring & Systems That Scale

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.

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 marketing budget, and why relationships—not just ad spend—are the real key to long-term business success. 🎧 What You’ll Learn in This Episode: * How to audit your digital footprint and uncover hidden marketing issues * The right way to calculate and prioritize your marketing budget * Why pay-per-click advertising may not be the best move for small businesses * The “presearch” method for building authentic LinkedIn relationships * How small businesses can compete with bigger brands strategically ⏱️ Episode Timestamps: * 00:01 – Welcome and guest introduction * 00:52 – Twin dad life and George’s personal journey * 01:53 – From corporate America to entrepreneurship * 03:07 – Launching EAG Advertising * 06:18 – The importance of niching down * 08:59 – Building relationships that drive business * 12:04 – LinkedIn outreach and the “presearch” strategy * 15:54 – Common digital marketing mistakes * 19:06 – Competing with big brands on a small budget * 24:04 – Why websites still matter * 28:37 – Growing and leading a team * 33:20 – Work-life balance as an entrepreneur * 37:49 – What “Do Small Business Like a Big Boss” means to George * 41:20 – Where to connect with George and EAG Advertising 👤 About the Guest: George Ennis is the Founder of EAG Advertising, a full-service marketing and advertising agency specializing in B2B, nonprofit, and complex industries. With more than 20 years of strategic agency experience, George helps small and mid-sized businesses create marketing strategies with big-business impact. Connect with George: LinkedIn: E.A.G. Advertising Website: eagadvertising.com [http://eagadvertising.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] 🔗 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.