From unemployed to an 8-figure exit with Chris Cobb

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Chris Cobb Interview on Freelance to Founder

In this episode, we interview Chris Cobb of Armstrong Transport. His story is very different from many we’ve told on Freelance to Founder. 

Our guest built his business with a dwindling cash reserve and with no knowledge of the business he was getting into. Only trust in his own work ethic, $15,000, and the expertise of his partner.

There’s no sexy email marketing software startup story here, no seven-figure online course on ‘course-building’, no niche community he developed and grew, no book, no agency – none of these things.

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Chris Cobb found success starting a freight brokerage, which evolved into a financial services firm, which he very recently cashed out to the tune of tens of millions. 

Here’s why you’re going to want to listen to this episode, even if transportation isn’t your thing. 

  • Get to learn about the creative, forward-thinking business that Chris exited in order to fund his freight startup
  • How and why Chris pivoted from freight brokerage to financial services firm 
  • How Chris broke through the mental barriers of hitting an intellectual wall with the business and survived a terrible decision which cost the company $300,000 as well as credibility with his business partner
  • How Chris views risk tolerance and manages his perceived deficiencies as a CEO and manager

We’ve never had a CEO of a company this size nor a founder story involving an exit.

We hope you enjoy this episode of Freelance to Founder.

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Brought to you by AND The Podglomerate podcast network, this is the show where we learn from entrepreneurs who understand focus and scale. They’ve started off as solo practitioners — developers, designers, product marketers, or creatives — and found out how to grow something to be bigger than themselves. What makes them unique is that in many cases they started these pursuits as freelance gigs… that ultimately took on a whole new life and scaled far beyond the founders’ expectations and definitely bigger than themselves.

You get to hear the details of what they did, how they did it, and what decisions were the hardest to make along the way.

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Support for this episode also comes from Penji. Penji is an on-demand graphic design service that offers unlimited designs. Not only will you be able to request a custom logo from a professional graphic designer, but you also have the opportunity to request unlimited revisions at no extra cost. Because of this, you know you’ll end up with a logo that you really love.

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