From Poker Tables to CrossFit Champion: Building a Business Around Elite Performance with Jason Grubb

A fireside chat with six-time CrossFit Games champion Jason Grubb reveals lessons in entrepreneurship, focus, and sustainable growth.

Jason Grubb's career trajectory reads like a masterclass in adaptation and entrepreneurial resilience. From psychotherapist to professional poker player, wedding photographer to CrossFit gym owner, and now CEO of Boulder Athlete—Grubb's journey offers valuable insights for anyone building a business while pursuing excellence in their craft.

The Discovery: Building Businesses, Not Just Careers

Early in his career as a psychotherapist, Grubb made a critical discovery: "I love building the business of therapy. But actually delivering therapy was not my jam." This realization became the throughline of his professional life—he's fundamentally a builder, someone energized by creating systems and businesses rather than just providing services.

This insight is crucial for entrepreneurs: understanding what actually drives you versus what you're credentialed to do can be the difference between burnout and fulfillment.

Identifying an Underserved Market

When Grubb decided to launch Boulder Athlete in 2023, he didn't just create another fitness program. He identified a glaring gap in the CrossFit market: "The majority of athletes in the CrossFit space are masters athletes over the age of 35, and they are not being served directly. No one is saying 'I am here for masters and that's it.'"

After pitching the concept to major training companies without finding the right partnership, Grubb took the entrepreneurial leap with a business-savvy partner who had previously sold tech companies. The key lesson? When you see a clear market need that others are ignoring, that's your opportunity.

The Lean Startup Approach

Boulder Athlete's growth trajectory demonstrates the power of starting lean and iterating quickly. Beginning with just 50 athletes in summer 2023, the company has grown to 800 members in two years—without significant outside investment.

Grubb admits to making mistakes early on: "I brutalized them for a couple of months. They were doing way too much work." But he credits his ability to adapt quickly, creating a tight feedback loop with early customers and continuously improving the product. "I'm fast at adaptation. I'm fast at learning. When I really get into something, I'm all in."

Today, Boulder Athlete maintains retention rates "way above industry standards," validating that the product-market fit is strong.

The Reality of Building While Competing

Grubb is remarkably honest about the imbalance required during startup phase: "I am completely imbalanced. I'm up doing zone 2 by 7 a.m. By 8 a.m. I'm at my desk programming for about 3 to 4 hours a day for three days of the week. Then I train from 1:00 till about 3:30. Then I have an afternoon session from about 4 till 6, sometimes 7 o'clock."

He wears every hat—CEO, programmer, marketer, community advisor. After two years of taking no salary, he's finally drawing income from the business. His perspective on work-life balance is pragmatic: "It's okay to be the best at what you do and to be building something else. There's seasons of imbalance that are just going to be part of it."

The key is awareness and communication, particularly with family.

Managing Multiple Revenue Streams

While building Boulder Athlete, Grubb maintains several revenue streams:

• Programming and coaching for 800+ Boulder Athlete members
• One-on-one coaching clients
• Content creation for brand sponsors (Barbell Apparel, Heart & Soil, and others)
• YouTube and Instagram content partnerships

This diversification provides financial stability during the startup phase while allowing him to focus on growing the core business. He views these as "side hustles" that fund the main venture until it reaches full profitability.

Content Creation as a Business Tool

Grubb's approach to content is refreshingly honest: "It is chaotic." Rather than rigid content calendars, he captures footage continuously throughout his day, building a library of B-roll that he can draw from when deadlines approach.

His environment is intentionally designed for content creation—a home gym, sauna, and cold plunge all serve dual purposes as training equipment and content backdrops. He's thoughtful about clothing choices and visual elements while training, knowing he might need that footage later.

When creativity doesn't flow naturally, Grubb leverages AI tools: "There's times when if I can't figure out how to say it, I can nudge ChatGPT to help me find the right way that I would talk about this particular brand."

The Non-Negotiable: Protecting Focus Time

Despite running a growing business, Grubb maintains strict boundaries around his 1:30 p.m. training session. "The workout is a non-negotiable. I have the commitment at 1:30 to train with the guys I train with."

This isn't just about athletic performance—it's about mental health and productivity. "I go train, I come home, I sit back down. It's legitimately two and a half to three hours later and I am in a completely different headspace and I'm much more productive."

He's learned that pushing through stress and skipping training actually reduces overall output: "When I try to work and I push training back, I'm not as productive as if I just stop."

Managing Distraction in a Digital World

Grubb struggles with focus like many entrepreneurs: "I have such a distracted brain. There's probably a spectrum of ADHD that I have." His strategies include:

• Keeping his phone upside down during work sessions
• Turning off all notifications during training
• Using multiple screens but dedicating all of them to a single task
• Avoiding his phone in the car after training, waiting to get home to respond to messages

"When I dedicate that time to the one thing and then the next thing and then the next thing, it's much less stressful actually. Much more healthy."

Building for the Long Game

Grubb is candid that the current pace isn't sustainable forever. He estimates needing "a couple more years" before achieving better balance—when he can finish work at 5 p.m. and not check his phone on weekends.

But he's playing the long game. By maintaining elite athletic performance while building Boulder Athlete, he's creating a business that leverages his unique expertise and credibility. The personal brand he's building as a six-time CrossFit Games champion directly feeds the authority and trust that powers his coaching business.

Lessons for Entrepreneurs

1. Know what energizes you: Building businesses versus delivering services are different skills. Align your work with what actually drives you.

2. Find the white space: Look for underserved markets where you have unique expertise and credibility.

3. Start lean and iterate: Launch with minimal resources, gather feedback quickly, and improve continuously.

4. Expect imbalance—but communicate it: High-performance seasons require sacrifice, but awareness and communication with stakeholders (especially family) is critical.

5. Protect non-negotiables: Whether it's training, meditation, or family dinner, some activities make everything else work better. Guard them fiercely.

6. Design your environment: Set up your physical space and daily rhythms to reduce friction for your most important work.

7. Diversify income during startup: Multiple revenue streams provide stability while building toward the main vision.

8. Leverage AI and tools: Use technology strategically to amplify your capabilities during high-demand periods.

9. Master single-tasking: Deep focus on one thing at a time produces better results than constant context-switching.

10. Build feedback loops: Stay close to your customers, learn quickly from mistakes, and adapt.