The Bootstrapped EdTech Playbook: Offshore Teams, DIY PR, and 20K Users

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.

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 rooted in relationships—what worked, what didn’t, and what every aspiring entrepreneur needs to hear. 🎧 What You’ll Learn in This Episode: * How to stop chasing money and start building through relationships * The “repeatable value” concept every founder must define before scaling * How to protect and maintain your business while stepping into a corporate role * Why mindset and self-worth are the biggest blockers to growth * What to focus on in your first 30 days before investing in branding or assets ⏱️ Episode Timestamps: * 00:00 – Introduction * 00:46 – Guest introduction: Joy L. King * 02:05 – Launching during the pandemic * 06:29 – Turning design into therapy and purpose * 09:21 – Building through referrals * 11:42 – “All money ain’t good money” * 17:34 – When chasing money backfires * 24:14 – Tools and systems Joy uses * 27:00 – Negotiating an executive role while keeping her businesses * 33:31 – The #1 mindset block * 38:15 – The first 30 days as a founder * 44:14 – What “Big Boss” means 👤 About the Guest: Joy L. King is a lifestyle architect, business coach, and executive. She is the founder of Lifestyles by Joy, a referral-based interior design firm, and Sweet Life Business Coaching, where she helps entrepreneurs define repeatable value and scale with intention. She also serves as a Chief at NCAN (National College Attainment Network), leading strategy and operations. 🔗 Connect with Joy: lifestylesbyjoy.com [http://lifestylesbyjoy.com]sweetlifebusinesscoaching.com [http://sweetlifebusinesscoaching.com]LinkedIn — linkedin.com/in/joyking912 [http://linkedin.com/in/joyking912] 🚀 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.

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 veterans connect with meaningful careers. This conversation dives deep into resilience, purpose, and practical business strategy, especially for founders building with limited resources but big vision. 🎧 What You’ll Learn in This Episode: * How Jordie turned a mission to serve veterans into a 30-person recruiting company * What the SkillBridge program is and how it supports both veterans and employers * Why the traditional resume model is becoming outdated * The most important hire to make when scaling a business * How to think about funding without giving up equity * Morning routines and time-blocking strategies from a serial entrepreneur * Why your first business should be designed to fail safely and teach quickly ⏱️ Episode Timestamps: * 00:04 – Welcome & intro to Jordie Kern and 7 Eagle Group * 00:49 – Growing up as the son of a WWII Army veteran * 04:21 – Early entrepreneurial ventures and working with the Clemente family * 07:23 – The moment Jordie started 7 Eagle Group * 10:06 – The reality of building the business from scratch * 12:48 – How the SkillBridge program works * 23:50 – The one-minute veteran video and why it works * 30:15 – Scaling a remote team of 30+ * 34:50 – Bootstrapping vs. investors * 36:35 – Systems, delegation, and protecting your genius zone * 43:50 – Advice for mission-driven entrepreneurs * 46:42 – What “Do Small Business Like a Big Boss” means to Jordie 👤 About the Guest: Jordie Kern is the founder of 7 Eagle Group, a mission-driven talent platform based in Amherst, Massachusetts that connects military veterans and transitioning service members with meaningful civilian careers. With over 35 years of entrepreneurship experience and seven businesses built, Jordie has grown 7 Eagle Group into a fully remote team serving 125+ SkillBridge participants daily through its career academy. The company partners with major organizations including Amazon, the Kansas City Chiefs, American Airlines, and Jack Daniel’s. Connect with Jordie: Website: 7eagle.com [http://7eagle.com] Email: jk@7eagle.com [jk@7eagle.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]