Best learning as an operator?

Ideas are cheap, execution is everything.

What is your favorite part about working with portfolio companies/entrepreneurs?

Founders have big, audacious visions and no one knows for sure whether it will be possible to achieve them. My favorite part of getting to work with our portfolio companies is watching them grow and accomplish their goals. From the small wins, to the big ones, to helping get through the inevitable low points, I like to be a partner on the journey and it’s really fulfilling to see the continued progress toward a dream.

How do you view your role with portfolio companies?

Generally I see our role as one of support and an advisor to the founder. I don’t pretend to understand the business as well as the founder, so I see our job as helping make sure they are asking the right questions and seeing the forest for the trees. As a VC we get a lot of breadth across business models and industries, and one of our jobs is to help founders leverage that.

What is one thing you wish more startup founders thought about earlier in their journey?

A compelling narrative for their company. Being able to tell a story is important in being able to raise money, hire key people, and to reach customers and media. Most founders don’t spend enough time developing a compelling narrative as it can be really hard and typically isn’t their core competency, but it can be so effective across a number of important vectors.

I get excited by companies where the founder is/ founders are….

Lifelong learners. No one has all the answers, so a thirst to learn and grow is so important. Creative problem-solving is also an important trait. Success is never a straight line, so being able to get creative in solving problems along the way is critical. Too many founders work from existing thinking and playbooks instead of being creative from first principles.

Favorite quote or saying?

You miss 100% of the shots you don’t take.
- Wayne Gretzky

What’s one thing people might not know about you?

I competed in a Red Bull Crashed Ice event. Essentially ice skating down a hill with moguls and jumps on it. It was one of the most insane and fun moments of my life.

What is your favorite hobby/outside of venture, how do you spend your time?

I still play hockey and am a budding grill/bbq fanatic.

What makes Redpoint unique?

Our team orientation.

Why did you choose to be a venture capitalist?

When I looked back on my career as an operator, I realized I most enjoyed the foundational stages of a company—when we were still charting the course, building the initial team and shaping the strategy. Venture is a way to be able to do that many times over, which is really fulfilling. I also love getting to work closely with so many different founders. They are built differently and it’s fulfilling to get to partner with people trying to invent the future.

What is the best trip you’ve taken and why?

I love Italy. The old, ancient towns, the incredible food and culture, the rolling hills, the people. It’s a magical place.

What job would you be doing if you were not a VC?

Probably something in hospitality. I love delivering great experiences to other people