In this episode, Oleksij Rak sits down with Jeremy Ostermiller — an eight-time founder who went from promoting hip-hop shows to building one of the first video ad exchanges, and who now runs two direct-to-consumer brands — to talk about positioning, community, and why so many founders never earn their first dollar.

About Jeremy

Jeremy Ostermiller has spent just past twenty years building companies — about 40,000 hours, by his own count. He started as a concert promoter, then used his ad background to launch Altitude Digital, one of the first video ad exchanges, growing it from zero to over a quarter billion in lifetime revenue before selling to private equity. He co-founded Edison Interactive next and now sits on its board, while running two DTC brands: Death Before Decaf, a ready-to-drink coffee company, and Steeltown Garage Co., a clothing brand he bought rather than built.

What we talked about

Zero to eight years. Why he hands every company over around year eight, and the kind of CEO he thinks should take it from there.

Buying a brand instead of starting one. How Steeltown Garage came off Flippa, and why starting from zero lost its appeal.

Positioning as the product. Why he took a coffee brand loud and masculine while the whole category was going the other way.

The launch that made the company. A Fourth of July party, a chance introduction, and a 7-Eleven shelf three weeks later.

Launch with a client. The rule he has used to ship technology since Edison Interactive, and why building for an imagined market is the expensive option.

The haves and the have-nots. His read on how AI split the field, and where he thinks the middle went.

Sharpest moments

He is blunt about where most founders actually get stuck:

"I tell people that the hardest dollar is the first dollar."

On the instinct to build your own infrastructure before you have customers:

"Does the world need another platform? Let's just be honest. Like does the world need another login?"

The Death Before Decaf break came at his own Fourth of July party, from a 7-Eleven franchise executive who had barely tasted the drink:

"I don't even care what's in this can, I know it's gonna be successful."

On knowing which years of a company he is good at:

"I'm kind of a zero to eight year type of guy."

And on what AI has done to the competitive field:

"It's the haves and have nots right now... I don't think there's anyone in the middle."

Key takeaways

• The first dollar is the hard one. Most founders never reach it because they are still perfecting a platform while the market moves past them.
• Build with a client who teaches you the market, rather than for a market you have imagined. Free or discounted first work is what buys you that education.
• Use established third-party tools until you can afford to peel pieces back and own them.
• In a commodity category, positioning can be the product. The coffee aisle went soft, so he went loud.
• Community compounds across industries. Four hundred concerts left him with an audience he could activate on day one of a completely unrelated business.
• Founder-market fit has a shelf life. Knowing which stage of a company you are good at is worth as much as knowing the industry.