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Freelance to Founder

175 EpisodesProduced by Millo / The PodglomerateWebsite

Clay and Preston have each grown their own one-person businesses to something much bigger and now they offer weekly coaching calls with freelancers ready to do the same. Your weekly dose of real-world, practical, actionable advice to take your service-based business to the next level—with occasional… read more


From unemployed to an 8-figure exit with Chris Cobb

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.

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 startupHow 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 partnerHow 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. Please do leave us an honest rating on iTunes.

Complete show notes for this episode can be found on

Thank you to our Sponsors for supporting this episode:

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This podcast is a production of Millo.

Recently from the Millo Blog:

What earning $33k from Fiverr taught me about building a freelance business


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Since you're listening to Freelance to Founder, we'd like to suggest you also try other Podglomerate shows surrounding entrepreneurship, business, and careers like and Creative Elements.

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