22: How Bootstrapping With $1,500 and Cold Calls Built a Multi-Million Dollar Ad Business

Matthew Diteljan co-founded a startup with just $1,500 and scaled it into a national advertising platform targeting high schools. After a partner buyout and burnout, he exited the company—but not without hard lessons. In this raw, honest conversation, Matthew shares how his dream exit turned into unexpected post-sale turmoil, what he’d do differently, and what every founder should consider before pulling the trigger on a deal.

Key Takeaways

• Starting with constraints forces creativity and sharpens focus.
• Bootstrapping helps you stay lean—but can limit scale if you resist outside capital.
• Partner alignment is critical; buyouts can get messy without strong communication.
• Abdicating leadership too early can trigger chaos; train successors with care.
• Walking away from a subpar offer can bring stronger, unexpected buyers.
• Your investment banker works for the deal—stay in control of your own vision.
• Financial freedom doesn’t guarantee peace—post-sale fallout can be brutal.
• Think beyond the exit: what kind of life and legacy do you really want?

 

Links & Resources

• Matthew Diteljan
  • LinkedIn: https://www.linkedin.com/in/diteljan/
  • Instagram: https://www.instagram.com/mattditeljan/

• Subscribe to the Podcast:

  • Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode.

• Newsletter & Exclusive Content:

  • Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates.

• Connect with Bruce & the Community:

  • LinkedIn: Bruce Eckfeldt

  • Instagram: @bruce_eckfeldt

  • Email:

    • [e-mail]

    • [e-mail]