Short bio
Kevin Oldham helps founders get unstuck. After watching his mom's skateboard shop consume everything the family had and living through his own agency collapse in 2023, he figured out something most business advisors miss: the same recovery principles that save lives can save companies. He's a CEPA and Kellogg-trained advisor who runs Founder HQ, BeTheFilament.com, and Diffactory, helping entrepreneurs either fall back in love with their business or walk away clean. Lifetime skater, black belt, person in recovery. Married to Andrea, dad to Landon and Lucy. His operating system: die empty, mind like water, chop wood daily.
Expanded bio
Kevin Oldham knows what it looks like when a business becomes a trap. He watched it happen to his mom, who poured everything into a skateboard shop that consumed the family and left them with nothing to show for it. Years later, he lived it himself when his agency collapsed in 2023. Those two experiences taught him something he couldn't have learned from any certification: most founders aren't struggling with strategy problems. They're struggling with identity problems. The business has become a prison they built with their own hands, and they can't tell the difference between the company and themselves anymore.
That's the problem Kevin solves. He helps entrepreneurs free themselves from the businesses they've created so they can make a real choice. Love the company and run it well, or list it and move on. No half-measures. No more white-knuckling through another year hoping things magically improve.
His approach is unusual. Kevin applies recovery principles to business stuckness, because the patterns are almost identical: denial, avoidance, the inability to ask for help, the slow erosion of everything that matters while you tell yourself you're fine. He's a person in recovery himself, and he's found that the framework translates with surprising precision to founders who are stuck.
He's not short on credentials. CEPA, Kellogg-trained. But the real education came from failure and from doing the work. Kevin runs Founder HQ, BeTheFilament.com, and Diffactory, each built to meet founders at different stages of that stuck-to-free journey.
Outside of work, Kevin is a lifetime skateboarder and black belt martial artist. He's married to Andrea and is dad to Landon and Lucy. He operates on a few simple principles: die empty, keep a mind like water, and chop wood every single day. Not because those sound good on a slide deck, but because they're the only things that have actually worked.
Mental models
Ventures
Photos
Photos by Steph Rupp. High-resolution files available upon request: koldham@diffactory.com.
Contact
koldham@diffactory.com (fastest response)