Patrick Oborn ran 250 miles through the Arizona desert at the Cocodona 250 — and came back with a blueprint for building businesses that don't quit. The Telarus co-founder and ultramarathon veteran breaks down why purpose-built teams, micro-goals, and embracing adversity are the real competitive advantages.
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Key takeaways
- Growth happens outside your comfort zone — the Cocodona 250 and Telarus both required pushing well beyond known limits before breakthroughs occurred.
- Purpose-built teams win: choose teammates for temperament and problem-solving ability, not just skill, and get their explicit commitment before the hard moments arrive.
- Break impossible goals into micro-targets: Patrick focused only on reaching mile 80 on day one; Telarus navigated growth one iteration at a time across five business pivots.
- Empathy beats rescue: the most effective support lets people feel their struggle while holding them accountable to keep moving — taking the pain away removes the lesson.
- Hiring a coach removed Patrick's performance plateau in ultrarunning — the same move (bringing in experienced outside perspective) unlocked growth at Telarus.
- Adversity exposure is a competitive advantage: the more you encounter hard situations, the better your real-time decision-making becomes under pressure.
- Perfectionism and distrust of others are compounding liabilities — recognizing and dismantling them is itself a form of leadership growth.
When 250 Miles Becomes a Business Case Study
Patrick Oborn didn’t start as a runner. He started as an engineer who did poorly at a local triathlon. That failure became a diagnostic exercise — identify weaknesses, find a coach, remove the ceiling — a process he applied identically at Telarus, the technical advising and consulting firm he co-founded. By the time he lined up at the Cocodona 250, a 250-mile foot race from Black Canyon City, Arizona, to Flagstaff with 42,000 feet of total elevation gain, the parallels between endurance sport and entrepreneurship had become impossible to ignore.
The Cocodona 250: What It Actually Demands
Unlike a standard ultramarathon, where aid stations appear every six or seven miles, the Cocodona 250 features four stretches with 17 miles between aid stations and a five-day cutoff. Runners must carry up to three liters of water. On race day, a supply shortage forced officials to cut water rations in half mid-course — leaving Patrick to filter cattle-pond water just to survive the next segment. Kidney failure, GI collapse, and sleep deprivation are not hypotheticals; several of his training partners have DNF’d for exactly those reasons.
Building the Purpose-Built Team
Patrick assembled a 12-person crew for a race where most competitors bring one or two. He approached roster-building like a baseball manager:
- A detail-oriented crew chief (and her husband) who brought supplies Patrick never requested — and needed by day two.
- Pacers selected not just for athletic ability but for temperament — people who radiate energy rather than drain it.
- A pre-race commitment from every team member to get him to the finish line, no matter what.
The first 80 miles were run solo. After that, a pacer ran every remaining mile alongside him. His mental anchor for day one was simple: just get to mile 80.
The Rock at Mile 138
Coming into Sedona — one of the most scenic stretches of the course — Patrick sat down on a rock and cried. He wasn’t planning to quit, but the weight of how far he’d already come, combined with how far remained, was overwhelming. Pacer Jill Wilkins sat beside him, let him feel it, and said: have your moment, and when you’re done, we’re going to get up and keep going. That response — empathy without rescuing — is what he identifies as the race’s most transferable lesson.
The Business Translation
Telarus has gone through five major iterations since its founding. Patrick draws a direct line between race strategy and company strategy:
- Micro-goals over macro-vision: The Cocodona plan sheet listed 35 aid stations. Focus on the next one, not the finish line.
- Knowing when to evolve vs. when to stay the course: Companies that pivot too early or hold old ideas too long both fail.
- Trusting the team: Patrick admits he was a perfectionist who struggled to delegate — the race forced him to dismantle that instinct entirely.
Squeeze CEO Carson Poppinger echoed the theme from a founder’s perspective: ten years of payroll anxiety and zero outside funding required the same one-aid-station-at-a-time mentality before anything clicked.
Giving It Back
Post-Cocodona, Patrick paced Jill for all 100 miles of the Wasatch 100, and planned to crew Adam Burke — his first Cocodona pacer — through the Havasu 100. The cycle of support, he argues, is how the lessons compound. No one achieves anything significant, whether running 250 miles or scaling a company, without a team willing to sit on the rock with them.
Growth happens on the other side of the boundary of your comfort zone — that area out there is where the good stuff happens.
— Patrick Oborn
Have your moment, and when you're done we're going to get up and we're going to keep going.
— Patrick Oborn
There's no one who does huge things in this world without a team, without a support system — whether you're president of the United States or running a company.
— Patrick Oborn
I was too stupid to quit.
— Carson Poppinger
Episode chapters
- 00:11 — Introductions & Patrick's connection to Squeeze
- 01:21 — From triathlete to ultramarathon runner
- 03:01 — Wasatch 100: failure, analysis, and the coaching breakthrough
- 04:43 — What is the Cocodona 250? Race mechanics explained
- 07:20 — Water crisis: filtering cattle-pond water mid-race
- 09:04 — Mental toughness and real-time decision-making
- 11:18 — Building a 12-person purpose-built crew
- 14:41 — Breaking down at mile 138 and the empathy lesson
- 19:30 — Business parallels: micro-goals, pivots, and team trust
- 29:52 — Final reflections and closing takeaways
Frequently asked questions
What is the Cocodona 250?
The Cocodona 250 is a 250-mile ultramarathon starting in Black Canyon City, Arizona, and finishing in Flagstaff, with 42,000 feet of total elevation gain and a five-day cutoff. It features some aid-station gaps of 17 miles, requiring runners to carry up to three liters of water.
Who is Patrick Oborn?
Patrick Oborn is the co-founder of Telarus, a technical advising and consulting company. He is also a competitive ultramarathon runner who has completed multiple 100-mile races and the Cocodona 250.
How does ultramarathon running translate to business lessons?
Patrick draws parallels around micro-goal setting, purpose-built team assembly, knowing when to pivot versus stay the course, and developing empathy through shared adversity — all skills he applied directly at Telarus.
What is a DNF in ultramarathon running?
DNF stands for 'Did Not Finish.' In extreme races like the Cocodona 250, DNFs often result from medical issues such as rhabdomyolysis (muscle breakdown) or kidney failure, not simply fatigue.
How important is a support crew for a 250-mile race?
Critically important. Patrick ran with a 12-person crew that included a crew chief, pacers selected for temperament, and RV support. Most 100-mile races require only one or two crew members.
What is Telarus?
Telarus is a technical advising and consulting company co-founded by Patrick Oborn. It has evolved through five major business iterations since its founding and is also an investor in Squeeze.