You might not expect snowboarding and venture capital to be connected, but for me, they are inseparable. Snowboarding has shaped how I approach nearly everything in life, including how I invest in and work with startups. It’s also why I named my firm Sidecut Ventures.
Let me explain.
At the relatively late age of 30, I fell in love with snowboarding. It wasn’t just a hobby—I became obsessed with mastering the sport and eventually teaching it. Over the last 20 years, I’ve built a part-time career in snowboarding, reaching the highest certifications in both able-bodied and adaptive instruction. I even spent three years on the PSIA-AASI National Team, working with adaptive athletes and helping set the direction for American snowsports education. I’m proud to say I was the first person of color on that team, and probably the first venture capitalist, too.
But this isn’t just about snowboarding. It’s about how it shaped my philosophy toward venture capital and why Sidecut is the perfect metaphor for how I think about investing.
In snowboarding and skiing, the sidecut refers to the curvature of the board or ski—the very thing that determines how you carve down the mountain. A deeper sidecut means tighter, quicker turns; a shallower sidecut allows for smoother, wider arcs. This geometry is fundamental—it shapes how you approach the slope and influences every turn you make.
I believe the same is true for early-stage startups. Just like the sidecut determines how a snowboard handles, the decisions made at the pre-seed stage shape the trajectory of a startup’s future. At Sidecut Ventures, we specialize in helping founders carve the right path, providing not just capital, but hands-on coaching to help them make the most critical decisions early on. These foundational choices can create a lifetime of efficiency, much like the right sidecut can make your ride smoother and more controlled.
Coaching is not just something I do; it’s who I am. I’ve often said that if I ever had to stop coaching—whether on the snow or in business—I would probably quit both. It’s what drives me, and it’s why I invest the way I do.
A few years ago, my then 10-year-old son, Sean, delivered a piece of feedback that changed the course of my life. He described my corporate job as "flying on planes and yelling at people." Brutal, but true. That comment hit hard and forced me to reevaluate what I was doing with my life. I decided to refocus my energy on what truly mattered to me—helping others grow and develop, whether through snowboarding or venture capital.
Coaching founders at the pre-seed stage, just like coaching athletes, is about being there at the most pivotal moments. It’s about giving them the tools, insights, and support to navigate their unique journey. This is also why I’m passionate about working with underrepresented founders and adaptive athletes—those who are often overlooked but possess immense potential.
As a solo GP, one of the most common questions I get is, "How do you scale?" The answer lies in my experience as a coach and examiner in snowboarding. For two decades, I’ve traveled the world, training and developing instructors. My role has been to help them become better coaches, preparing them for higher levels of certification and leadership in their own right.
At Sidecut Ventures, I take the same approach. We’ve built a network of exceptional Operating Partners—people I’ve worked with over the years who bring deep experience in Fortune 500 companies, zero-to-one startups, and industry-specific expertise. These partners are not just investors; they are startup coaches. Our goal is to provide founders with tailored guidance, not a one-size-fits-all approach.
For example, Christina Dragonetti, our first Operating Partner, played a key role in refining our due diligence process during our investment in Duet. She helped implement a more structured and data-driven approach, ensuring that our assessments were thorough and unbiased. This kind of collaboration, rooted in a coaching-first mindset, is what allows us to scale while maintaining the high-touch approach that’s core to Sidecut Ventures.
One of the toughest but most rewarding roles I’ve had in snowboarding is serving as an Examiner. I run exams where instructors either pass or fail their certifications based on their technical, teaching, and people skills. It’s a rigorous process, with only about 25% of candidates passing their highest-level certifications on the first try. This experience taught me the importance of objective, data-driven evaluation—an approach I’ve brought to venture capital.
At Sidecut Ventures, we’ve developed a meticulous due diligence process—what I call "Do Diligence." It’s based on the same framework I used as an Examiner: Observation → Evaluation → Prescription.
Without going too deep into skiing and snowboarding
Here’s how it works: Before offering a term sheet, we issue a "Learn Sheet," which is part investment memo, part consulting plan. During our 30-day due diligence process, we document everything a founder does—emails, transcripts, video meetings, and more. Each observation is tagged and classified within our deal framework. Only once we’ve gathered all the data do we evaluate the team’s performance and make a decision. It’s labor-intensive, but it’s how we ensure we’re making objective, informed investment decisions.
I learned from snowboarding that it doesn’t matter how good someone was last week—it’s about how they perform when it counts. The same applies to startups. At the end of the day, we need to see founders execute in real time. We value their history and potential, but we also need to see how they deliver under pressure.
So, why is my firm called Sidecut Ventures? Because just like the geometry of a snowboard determines the turns you make, the decisions made at the earliest stages of a startup define its future. At Sidecut Ventures, we are here to help founders carve the right path, combining coaching, precision, and a relentless focus on execution.
Coaching isn’t just a part of our investment process—it’s the heart of everything we do. Whether on the snow or in the startup world, the right cut makes all the difference.