Being an entrepreneur mirrors being an athlete: you put everything into it with no guarantee of what emerges, hoping for the best.

Moises Jimenez lives this reality. As a North Face-sponsored trail runner in Boulder and Vert.run co-founder, he navigates competing globally while building a coaching app that's served 170,000 athletes since 2019.

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Born in Venezuela and raised in Chilean Patagonia from age eight, Moises grew up staring at mountains wondering what existed on the other side. Despite playing multiple sports, he was never talented. What he could do was endure, earning a spot on the basketball team not for skill but stamina.

University life demanded an outlet to balance intense studies. Jogging twenty minutes became thirty. Then he saw a video of someone running trails to a summit. The combination clicked instantly. He grabbed a water bottle, tried running the closest hill, stopped halfway. Next weekend, three-quarters. Third weekend, he summited. It became his life.

By 2015, after winning races in Chile and Argentina, he tested himself against Europeans at Lavaredo in Italy. Camping to save money, taking down his tent race night to avoid fees, he finished top 10. That's when he committed seriously. His North Face partnership evolved from gear to financial support after becoming the first Chilean to win the competitive 50-miler at Endurance Challenge Chile.

His approach to growing brand partnerships centers on three pillars: global-level performance, consistent communication, and creative mountain projects beyond racing. For The North Face, FKTs and unique challenges that inspire the community carry significant weight. Understanding what each brand values proves critical.

This philosophy led to the Boulder Boys podcast with four training partners. Tuesday and Thursday evening runs turned into 90-minute conversations about contracts, athletes, races. They started recording those discussions. The purpose: capture conversations and create excuses to gather weekly over pizza. It's not about monetization. Revenue covers pizza and gear drops. Organic growth comes from authentic, fun conversations.

Trail running and digital innovation rarely coexist. ITRA's interface remained subpar for years. Ultrasignup's race search is notoriously challenging. Moises and co-founders Max and Kirsten (a photographer) saw opportunity.

The vision: make quality coaching scalable. Moises was coaching individually but hit a ceiling at maybe 50 people. Trail running presents more variables than road running. Road has three: time, distance, experience. Trail adds elevation gain, terrain type, weather, and distance is rarely constant.

They started scrappy in 2019 with a landing page and free weekly training plans via email. When 7,000-8,000 people used it weekly with strong open rates, they raised $100K from friends and coached athletes. That funded a web platform with dynamic plans and optional coach adjustments. They launched in 2020. Horrible timing.

COVID devastated the model. Trail runners pay for training when they have race goals. Canceled races throughout 2020-2021 meant people weren't signing up, so they didn't need plans. The trail running customer is conscious with subscriptions, not frivolous.

They survived staying lean. Then Silicon Valley Bank collapsed. Vert.run banked with SVB. Suddenly, no cash access.

"That's just entrepreneurship. The only thing constant is the amount of stuff that can go wrong at the same time. You just got to be resilient and stay afloat."

The main survival skill? Focus. They joined a Silicon Valley accelerator remotely, raised a few hundred thousand in seed capital, and funded improvements plus becoming UTMB World Series coaching partner for 12 races across 2023-2024.

In 2025, they rebuilt the entire architecture and developed AI coaching. Previously, every customer had a human coach manually checking plans. Hard to scale, limiting pricing flexibility. At $25/month with human coaching, it worked but constrained growth.

The new structure split into two tiers: Vert Pro ($19/month) for fully automated AI coaching trained on 170,000 coached runners, and Expert Tier ($45/month) for real human coaches with onboarding calls.

The genius move: offering Vert Pro annually at $119 (about $9.90/month). This shifted annual plan adoption from 3-5% to 50%. From a business perspective, this transforms customer lifetime value and cash flow, realizing $119 upfront instead of waiting months with cancellation risk.

The AI isn't inferior. It's trained on years of real coaching data, understanding how coaches adjust plans. The finish rate for Vert.run athletes exceeds 90%.

One critical learning: most free users stay free. The conversion window is narrow. Someone who will pay typically does so within the first week of experiencing value and getting the right engagement triggers.

Strava exemplifies this challenge. With 150 million users and only 2-5% paid, converting long-time free users proves extremely difficult. The key is converting warm leads quickly by demonstrating value immediately.

They've explored affiliated programs with nutrition and shoe brands. The data exists: thousands of daily coach-athlete interactions where coaches recommend gear. They could monetize those recommendations but focus prevents dilution.

The team is small. The product is young. Weekly releases are coming. Chasing extra revenue streams dilutes energy and increases risk for marginal gain.

The upcoming algorithm (V3) will create customized plans during onboarding rather than adapting templates. It reads your training history, understands your races, and crafts a plan specifically for you, adjusting in real-time.

Their workout library contains thousands of options for all conditions. London-based UTMB training differs completely from Boulder or Germany. This addresses reality: most ultra runners live in cities without daily trail access.

Vert.run is breaking even, not swimming in cash but profitable through strategic choices: dev team in Latin America, team members in Europe, and relentless product focus.

They're not building a growth machine for capital raising's sake. But opportunity exists: hundreds of thousands trail runners pay for coaching annually. Strategic brand partnerships with innovators like Hoka could accelerate growth more effectively than pure cash, creating symbiotic relationships that lower customer acquisition costs.

They've raised three times, most recently through internal crowdfunding with customers who wanted to become small shareholders. Success to Moises means current reality: working hard, training hard, traveling, racing, having a family, and supporting 10 full-time salaries. He's not waiting for success; he's living it in small daily achievements.

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Jon is a runner, cyclist, and podcast host from Boston, MA, who now lives in Boulder, CO. For The Long Run is aimed at exploring the why behind what keeps runners running long, strong, and motivated.

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