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

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Podcast Mantra:
Build the dream messy, build it scared, just don’t build it small.

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