From Trans America Racing to Building Businesses

When I first lined up at the start of the Trans America Bike Race, I had no idea I was actually preparing for a career in entrepreneurship. The 4,200km journey from Oregon to Virginia would teach me more about business strategy, resilience, and performance optimisation than any MBA course ever could.

The Race That Changed Everything

The Trans America Bike Race isn't just long—it's a masterclass in resource management, strategic thinking, and mental resilience. You're completely self-supported, carrying everything you need while racing against time and the elements. Every decision matters: when to sleep, what to eat, which route to take, how to manage your energy reserves.

Sound familiar? Because that's exactly what running a business feels like.

Lesson 1: Strategic Planning Under Pressure

During the race, you're constantly making strategic decisions with incomplete information. Do you take the mountain pass that's shorter but steeper? Do you stop for food now or push on to the next town? Do you sleep for three hours or push through the night?

In business, it's the same. Do you launch the product now or wait for more features? Do you hire more staff or invest in automation? Do you enter that new market or consolidate your existing position?

The race taught me that perfect information is a luxury. Great decisions come from understanding the core variables, assessing risk quickly, and committing fully to your choice.

Lesson 2: The Power of Systems

Ultra-distance cycling is all about systems. Your nutrition system, your sleep system, your bike maintenance system, your route planning system. If any system fails, the whole effort can collapse.

This translated directly to building businesses. At Postino, we developed systems for client onboarding, strategy development, and results measurement. At Glazing Supplies Direct, we built systems for inventory management, quality control, and customer service.

The businesses that scale are the ones with robust, repeatable systems.

Lesson 3: Mental Resilience Through the Dark Moments

Every ultra-distance race has dark moments. Hours when everything hurts, when you question why you started, when stopping seems like the only rational choice. The race continues in your head long before your legs give out.

Building businesses has identical moments. The client who doesn't pay. The product launch that flops. The team member who quits at the worst possible time. The cash flow crisis that keeps you awake at night.

The race taught me that these moments aren't failures—they're test points. How you respond when everything goes wrong determines whether you finish or not.

Lesson 4: Resource Optimisation

In ultra-distance racing, you can't carry everything you want. Every item has to justify its weight. Is this tool essential or just nice to have? Can this serve multiple purposes? How do I get maximum value from minimum resources?

This mindset became crucial in business. Every hire, every expenditure, every feature has to pass the same test. Small businesses don't have the luxury of waste. You learn to get remarkable results with limited resources.

Lesson 5: Community and Solitude

The race is largely solitary, but the ultra-cycling community is incredibly supportive. You help competitors with mechanical issues. You share information about road conditions. You celebrate each other's achievements.

Business feels lonely, but the best entrepreneurs understand the value of community. Sharing insights, helping competitors (yes, really), celebrating others' successes. The business community that supports each other succeeds together.

The ADHD Connection

What I didn't know during my racing years was that I had ADHD. The same neurological differences that made traditional office environments challenging made me exceptionally suited to ultra-distance racing and entrepreneurship.

ADHD brains thrive on:

Ultra-distance racing and building businesses both provide these in abundance.

Applying Racing Lessons to Business

**Goal Setting**: Break massive objectives into daily milestones. In racing, it's miles per day. In business, it's revenue targets, customer acquisition, or product development stages.

**Performance Monitoring**: Track the metrics that matter. In racing, it's speed, heart rate, and nutrition. In business, it's customer acquisition cost, lifetime value, and cash flow.

**Recovery and Maintenance**: Just as bikes need maintenance and bodies need recovery, businesses need regular attention to systems, team wellbeing, and strategic review.

**Adaptation**: Races never go according to plan. Weather changes, mechanical issues arise, route conditions vary. Successful racers adapt quickly. The same applies to business.

The Results

This racing mindset has been fundamental to building three successful businesses:

Each business faced its own "dark moments." Each required strategic thinking under pressure. Each demanded resource optimisation and systematic approaches.

The Journey Continues

I still cycle regularly, though competitive racing has taken a back seat to business building. But the lessons remain central to how I approach every challenge:

Whether you're racing across America or building a business from scratch, the fundamentals remain the same: strategic thinking, mental resilience, resource optimisation, and the courage to keep pedaling when the road gets tough.

The start line and the board room have more in common than you might think.