Backing the Bold (Through the Noise)

Kyle was the guest on episode 17 of Alex Banks’s Through the Noise (“Startups and venture capital. Without the noise.”), published July 17th, 2022. Roughly 59 minutes. It was recorded on July 14th, 2022, two months after Kyle joined Contrary to co-found its later-stage practice. Episode page on Listen Notes.

Summary

The episode description introduces Kyle as a General Partner at Contrary Capital, which backs “some of the boldest entrepreneurs of our time” and whose portfolio includes Anduril, DoorDash, Ramp and Synthesis. It notes he joined Contrary in May 2022 to co-found the firm’s later-stage practice, after time as a partner at Index Ventures and as a growth investor at TCV and Coatue.

The questions Alex sent ahead of time (below) set out the arc: how Kyle came to his investing philosophy, what the later stage looks like from the inside, and where venture capital is heading.

Questions Sent Ahead of Time

The Start, Investing Philosophy to Contrary

1. Portfolio ideas section on your website, ‘art of investing’. Taking finite resources (time, energy, money, attention) and employing them to optimize an outcome. You said you’re fascinated by the first principles of what it means to simultaneously learn to become a great investor while reinventing the art form. How did you stumble across this philosophy?
   • West Wing story
2. You spent the better part of seven years across Index, Coatue, and TCV focused on working with founders later in their journeys, what fundamentally interests you about this stage within the growth lifecycle?
3. Investing at a later stage is often viewed as “less risky”. What are the merits and drawbacks you’ve discovered throughout your career operating at this level?
4. Contrary is focus on early high conviction investing. How does conviction vary from an early stage to a growth stage?

Future of VC

1. VC mythical “value add”. Your newsletter piece at the beginning of this year “The Productisation of Venture Capital”. You said “very few investors could give an answer to the question “what is your unique differentiated offering to founders?” Why is it becoming harder and harder to differentiate brand?
2. Why are we seeing this shift in VC from large monolithic brands to the individual are a more personal level?
3. What does your perfect day look like?

Previous Guest Question

1. If you only had one question to interview a candidate what would it be?

Transcript

Not yet available.

Connections

• The Productization of Venture Capital: the Investing 101 essay the “value add” question quotes.
• Contrary Capital, Index Ventures, Coatue, TCV: the firms in the episode description.