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 business training, funding, or a clear roadmap. From surviving on $37,000 in his first year to cold-walking contractor offices with zero sales experience, to now co-owning a company competing with teams 25x their size, Stephen breaks down the real lessons behind resilience, leadership, and growth. 🎧 What You’ll Learn in This Episode: How to keep going when you're left alone in a business and everything is on the line Why cold outreach often fails—and what actually works for lead generation How radical transparency builds trust and drives revenue Why you should master roles before delegating them What EBITDA is and why it matters for long-term business value How systems, tools, and AI support growth in modern businesses The mindset needed to handle rejection and stay in the game ⏱️ Episode Timestamps: 00:25 – Welcome & What is Project MAPIT 02:47 – From teacher to tech startup: Stephen's origin story 04:30 – When the founder left and Stephen stayed in the fight 07:24 – The family decision and support system 10:50 – Wearing every hat in the early years 13:30 – Lead generation: what worked and what didn’t 16:05 – Handling rejection in sales 18:00 – Learning roles before delegating 21:34 – Buying out a founder 23:53 – Understanding EBITDA 25:45 – Systems, tools, and AI 31:30 – AI in small business 33:06 – Advice for entrepreneurs 36:35 – What “Do Small Business Like a Big Boss” means to Stephen 38:30 – Where to find Stephen 👤 About the Guest: Stephen Spence is the Managing Director and Co-Owner of Project MAPIT, an all-in-one mapping, reputation, and sales platform for contractors in the home services industry. A former special education teacher and coach, Stephen transitioned into entrepreneurship in his 40s and helped scale Project MAPIT into a competitive software company serving hundreds of clients. Connect with Stephen: Website: projectmapit.com LinkedIn: Stephen Spence 🚀 Ready to Make Your Business Official? Join Aisha’s FREE weekly webinar, Make Your Business Official, and learn how to build, brand, and bulletproof with confidence. 👉 Register here: https://www.igotnext.co/training 👉 Grab your FREE Legal Guide at: 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 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.