I spend much of my professional life in front of a screen, working at the intersection of digital platforms, artificial intelligence, content, live experiences, and the complicated institutional systems that shape participatory, college, and youth sports. Much of that work involves helping organizations raise capital, clarify strategy, develop partnerships, and grow. It also means identifying opportunities that are not always obvious: where technology can improve access and decision-making, where media can build deeper connection, where sports properties can create more sustainable commercial models, and where partners can align around shared objectives to create meaningful value.

I genuinely enjoy the work. I like the pressure of a complex problem, the process of finding a path through competing interests, and the moment when a conversation becomes a practical idea a team can actually execute. I enjoy the energy of meetings in New York City, the intensity of negotiations, the pace of building relationships, and the ambition that comes from being surrounded by people who are trying to make something happen.

At the same time, I have learned that the work remains meaningful only when another internal drive is fueled by something more elemental.

For me, that place is outside.

I Do Not Seek Balance

I do not think of the outdoors as a counterweight to work, and I do not seek “balance” in the conventional sense. Too often, balance suggests compromise between two competing forces: give a little here, take a little there, and settle somewhere in the middle to avoid falling. Balance is a form of settling for mediocrity.

That has never been especially compelling to me.

I do not want a life engineered to avoid failure, discomfort, or intensity. I do not believe that the goal is to reduce the peaks and valleys until everything becomes manageable. The summit is not reached through moderation alone. It requires commitment, preparation, discomfort, persistence, and, at times, an acceptance that the conditions will be difficult.

The outdoors does not diminish my professional ambition. It strengthens it. It gives it perspective, discipline, and energy. It reminds me that effort is not something to be avoided; when directed toward something meaningful, it is often the point.

Sport Before the Industry

Before sport became an industry of rights packages, recruiting systems, NIL strategies, audience analytics, creator platforms, and content calendars, it was fundamentally about movement. It was about using your body, testing yourself against distance or terrain, learning what you could handle, and sharing the experience with others who had chosen to do the same.

That is still what draws me to outdoor sport. Running, cycling, skiing, hiking, and open-water swimming have each given me something different over the years. Together, they have brought comfort, challenge, success, pain, loss, perspective, and community.

A long run can make a difficult business problem seem less fixed than it did an hour earlier. A ride can create enough space for an idea to develop without forcing it. Skiing can restore the simple pleasure of being fully engaged in the present, where the terrain and conditions demand your attention. Hiking slows the world down, while open-water swimming offers a more immediate lesson in focus, composure, and respect for the surrounding environment.

Those experiences do not remove the pressure of work. They put it into perspective and fuel the internal drive that makes sustained work possible.

A Colorado Sense of Place

I was born and raised in Colorado, and I still feel a powerful gravitational pull toward its outdoor lifestyle and culture whenever I return. The landscape has a way of making the world feel both larger and clearer: mountains that reset your sense of scale, weather that reminds you that you are not in control, and long stretches of trail or road that reward patience more than speed.

Colorado remains magical to me not simply because it is where I grew up, but because it shaped some of my earliest understanding of what sport could be. The outdoors was never merely a setting for activity. It was part of the experience itself, a place that demanded preparation, instilled humility, and made achievement feel earned.

The mountains taught me that progress often happens gradually. You reach a summit, complete a long ride, or navigate a difficult run not through a single burst of effort, but by continuing to move forward when the work becomes uncomfortable. They also taught me that the best experiences are often shared: meeting someone at a trailhead before sunrise, riding alongside a friend through changing weather, or recounting a difficult day over food afterward.

Those lessons have stayed with me, even as my professional life has moved into very different environments.

A Change of Scenery

Since relocating from New York to northwest Connecticut, I have found another version of that connection. It is different from Colorado, but it has become equally meaningful in its own way.

The wooded trails, quiet roads, lakes, and changing seasons create an outdoor life that feels close and accessible rather than distant or dramatic. A run can begin directly from home. A bike ride can become an extended stretch of solitude and thinking. A hike can transform an ordinary afternoon. A skin up a nearby ski hill offers a quick reset, while an open-water swim can make the rest of the day feel more grounded.

What I appreciate most is that the outdoor world here has become woven into daily life. It is not something reserved for a major trip, a special occasion, or a carefully planned weekend. It is part of the rhythm of where we live. That accessibility has created a genuine sense of peace and happiness while connecting us with people who understand the value of being active outdoors.

There is a particular kind of community that grows around outdoor sport. It is less concerned with status and more grounded in shared effort. People show up for the same early rides, choose the same difficult routes, wave or exchange a friendly word when passing, wait out the same weather, and learn to appreciate the small rituals that make a life outdoors sustainable over time.

What the Work Can Learn

The relationship between my professional world and my outdoor life is not a contradiction. In many ways, it is the point.

I believe deeply in the potential of technology, AI, data, media, and new business models to improve sports. Those tools can help people navigate complex systems, increase access to useful information, reduce administrative friction, tell more meaningful stories, and make participation easier for athletes, families, coaches, schools, and communities.

But technology should strengthen the human experience of sport rather than replace it.

Sports organizations often speak about engagement, retention, belonging, wellness, participation, and community. Outdoor sport offers a powerful reminder that those ideas cannot be reduced to a metric, a marketing campaign, or an optimized funnel. People remain connected to sport because it gives them a reason to move, an opportunity to challenge themselves, a group to belong to, and memories that are difficult to replicate elsewhere.

The strongest sports organizations of the future will understand that their responsibility goes beyond attracting attention. Their real work is to create the conditions for people to participate, progress, connect, and develop a lasting relationship with a sport and the communities around it.

That is true whether the organization is a youth program, a college athletic department, an endurance event, a ski destination, a swim club, a professional league, or a media platform.

The event matters. The platform matters. The business model matters. But what matters most is the life people can build and the connections they can form around those experiences.

Returning to Center

I do not want less ambition in my work. I want ambition that remains connected to something real.

I enjoy the city, the meetings, the work of building, the negotiations, and the challenge of helping ideas become durable businesses or institutions. I want to continue working where sports, technology, media, and culture intersect, particularly when there is an opportunity to build systems that are more useful and more humane than those that came before.

At the same time, I sometimes dream about returning to my days as a ski bum or ski and snowboard instructor. I think about what it would mean to work in a role that helped more people get outside and discover that rare, magical moment of weightlessness; when worry, deadlines, meeting rooms, rings, beeps, and the constant hum of a connected world fall away.

I also know that I think best when I remain connected to the world beyond the screen.

Running reminds me that progress is built through consistency. Cycling creates distance from the immediate pressure of a problem and often makes the answer easier to see. Skiing demands presence because hesitation and distraction rarely serve you well. Hiking teaches patience and attentiveness. Open-water swimming reminds me that uncertainty can be uncomfortable without being dangerous, and that composure is often the difference between panic and possibility.

The outdoors does not pull me away from the work. It gives the work its proper context.

It reminds me that sport is not only an industry to modernize, a property to monetize, or a system to restructure. At its best, sport is a vehicle for confidence, connection, health, courage, friendship, and a fuller life.

That is why, before my day begins in earnest and after the meetings, deadlines, travel, calls, and work of trying to build what comes next, my return to center is outside.

Old-school and dangerous.

The next decade in sports, sports tech, and media-adjacent platforms will not reward founders who hire for optics and comfort. It will reward those who know the difference between people eager to please and those eager to win.

The Wrong Signal

Traditional hiring culture has spent decades rewarding people who fit neatly inside big systems. Stay in your lane. Be easy to manage. Accumulate tenure. Follow the expected path. In mature enterprises, that can be entirely rational. Large organizations genuinely do benefit from long-tenured, fully dedicated executives who carry institutional memory, internal trust, and the ability to shepherd multi-year agendas across complicated structures.

But startups are not mature enterprises. Growth-stage platforms with small teams, thin budgets, and unproven business models are playing a different game. Copying enterprise hiring logic into that environment is like lining up for a time trial on a beach cruiser: wrong equipment for the course.

The Sports Business Journal’s recent roundtable on “The Future of Jobs in Sports” underscores just how out of date many hiring instincts already are. The conversation centers on a post-COVID sports industry being reshaped by AI, private equity, evolving skill demands, and changing pathways into leadership. If the industry’s own CEOs, chief people officers, search executives, and athletic directors are acknowledging that talent models are changing, then dismissing experienced operators because their careers are non-linear or portfolio-driven is not discipline. It is a failure to recognize the market as it actually exists.

Fractional Is Often the Rational Choice

Fractional and portfolio leadership are no longer niche hacks. They exist because the underlying math changed.

Early-stage and growth-stage companies need senior judgment in operations, finance, product, and go-to-market. What they usually lack is the cash or stability to justify a full traditional C-suite. Fractional executives solve that gap by letting founders buy judgment, pattern recognition, and systems in stage-appropriate doses.

For a resource-constrained sports or sports tech startup, that is often the smarter move:

• Access proven operators without locking in fixed executive cost too early.

• Experiment with what kind of leadership the company actually needs before crystallizing the org chart.

• Keep the structure light enough to pivot while still avoiding obvious rookie mistakes.

A young company does not need every key role filled by a 10-year, non-fractional executive sitting in a chair five days a week. It needs the right experience showing up at the right times, in the right ways, and at the right price.

Non-Linear Does Not Mean Unserious

This is where the bias shows up most clearly. A non-linear career is still treated as a red flag by people who grew up in a one-company, one-ladder world. That might have been fair in a calmer era. It is not fair now.

Executives who built their careers across multiple platforms over the last decade have been dealing with COVID-19 disruptions, layoffs, restructurings, platform shifts, and new business models. Many deliberately chose portfolio careers and fractional work because they wanted ownership, range, and the ability to go where the hardest and most interesting work was, not because they could not hold a job.

That is not someone optimizing to be liked. That is someone optimizing to win.

There is a real difference between a career pleaser and a career competitor. One organizes a path around being easy to keep. The other organizes a path around chasing hard problems, upside, and real stakes, accepting that big wins and real misses come with the territory. On paper, those two careers look very different. In a disrupted market, the second one often produces more relevant experience.

The Title Inflation Problem

At the same time, many founders who are skeptical of seasoned fractional operators are very comfortable inflating titles for extremely young, untested talent.

Pull up a stack of sports and sports tech pitch decks, and you will see the pattern instantly:

• A team slide full of C-titles at pre-seed or seed.

• One founder with legitimate background.

• A ring of 22- to 26-year-olds listed as COO, CMO, CRO, or “Chief Athlete Officer,” with thin operating histories underneath.

Investors do not read that as ambition. They read it as compensation.

Over-titling early creates predictable problems:

• Top-heavy optics before a business has earned it.

• Confusion about who is actually accountable for product, revenue, or operations.

• A future collision when the company actually needs senior leadership and has to untangle symbolic titles from real scope.

Titles should follow scope and impact. They should not be used as résumé candy or a shortcut to maturity.

Athlete Cachet Is an Accelerant, Not an Operating System

The temptation is even stronger in athlete-led or athlete-adjacent businesses. The thinking goes like this: if we give the athlete or recent grad a big title and put them on the front of the deck, we will drive value just on the back of their name.

Athlete and creator cachet is powerful. It can open doors, drive attention, and lend authenticity that no performance marketing budget can buy. But even the most thoughtful investors in creator- and athlete-led brands will tell you that celebrity is an accelerator, not the core business model.

A real company still needs:

• A product and tech stack that works.

• A go-to-market motion that scales beyond the founder’s personal network.

• A business model and operating cadence that can survive injuries, seasonality, and the reality that stars age out.

Putting all of that weight on someone in a first job because they have a jersey or a blue-chip degree is not progressive. It is reckless.

What Investors Actually See

From an investor’s seat, the combination of fear of fractionals and love of big titles shows up as a clean red flag.

When seasoned sports investors look at a team slide, they are asking:

• Who has actually shipped and iterated a similar product?

• Who has sold into this buyer set and owned the revenue motion?

• Who has enough operational maturity to handle the upcoming pivots and personnel decisions?

If the answer is one person and a group of very young C-titles, that is a problem. Gaps are not the issue. Every early-stage team has gaps. Pretending those gaps are covered by titles and logos is the issue.

This is where fractional and portfolio executives are not a maybe. They are the obvious fix. A lean founding team that is honest about its holes and brings in real operators, even one day a week, is far more investable than a deck stacked with symbolic chiefs.

The Real Divide: Pleasing vs. Winning

Underneath all of this sits a simple divide.

Some people, and some companies, are optimized to please. They value smooth optics, stable résumés, and familiar patterns. They like careers that look good in a board packet. There is nothing inherently wrong with that, especially in mature, slow-moving organizations.

Others are optimized to win. They value hard problems, real stakes, and the freedom to move when the best opportunity shifts. They choose roles, platforms, and even sports that offer the chance to feel the full range of outcomes, not just a safe middle ground.

In a sports industry being rewritten by AI, private equity, shifting media models, NIL, global investment, and changing fan behavior, the second mindset is not a flaw. It is an asset.

Founders who cling to the old signals, linear tenure, big titles for youth, and skepticism of portfolio careers are screening out exactly the kind of operators they want in their corner when the game changes. Founders who get it will:

• Match leadership design to company stage.

• Combine young, ambitious talent and athlete cachet with experienced operators, fractional or full-time, who know how to build.

• Judge people by the quality of problems they have taken on and the outcomes they have driven, not just how long they sat in one chair.

Those founders will attract better talent, use capital more intelligently, and build more resilient platforms.

The ones who do not will keep hiring for comfort, titling for show, and wondering why the people who are actually wired to win keep choosing other games.