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

Written By Bruce Eckfeldt

Matthew Diteljan, Co-Founder and former CEO, Glacier

In this compelling episode of From Angel to Exit, host Bruce Eckfeldt speaks with Matthew Diteljan, a founder who bootstrapped a company from a $1,500 university side hustle into a profitable advertising platform with national reach. Initially placing ads on his own campus, Matthew pivoted into high school advertising, bridging universities with potential students through physical and digital media. The business gained traction quickly, but behind the scenes, the stress of scale and misaligned visions with his co-founder began to take their toll.

After buying out his partner using a sizable personal loan, Matthew tried to step away and let a general manager take over. That decision led to operational breakdowns, culture shifts, and ultimately a full return to stabilize the business. COVID hit, revenue declined, and Matthew had to rebuild while grappling with whether to hold or sell.

He eventually decided to sell—but only after walking away from an initial offer that didn’t feel right. That moment of clarity led to a better deal with a new buyer… but what followed was far from ideal. Cut out of operations, caught in post-sale conflicts, and witnessing the company struggle under new leadership, Matthew now reflects candidly on what went wrong.

His key message: a founder's emotional and strategic readiness matters as much as financial metrics. Rather than fully exiting, he now believes a smarter path could have been raising capital, scaling with a leadership team, and staying lightly involved.

This episode is a must-listen for any founder considering an exit. Matthew’s hard-earned wisdom will resonate with anyone who has faced the emotional and strategic complexity of stepping away from a business they built from scratch.

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?

Contact Information:

Bruce Eckfeldt
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