Breaking Into Venture During A Downturn & Navigating Your First Year

Cowboy Ventures
Cowboy Ventures
Published in
2 min readApr 10, 2023


By Matt Lu & Robby

In 2020, our team shared resources on how to break into venture capital. That post generated a lot of interest and we received feedback that it helped folks understand how to recruit into and be successful as an entry-level venture capital investor. Our newest team member, Matt Lu, actually used these resources to land his first role in VC at Bullpen Capital — he would go on to join Cowboy in the years that followed.

We’ve seen firsthand the power of the venture industry and we’re big believers that everyone should have access to knowledge on how to break into the industry and be successful on the job. Having diverse perspectives around investing tables will only help accelerate the pace of innovation.

That said, the venture climate has changed a lot since 2020. Public market valuations for tech companies have declined significantly, sending ripples through the private markets and lowering the expected returns for venture investors. As valuation multiples compress and deal activity slows down, some firms are even reducing their fund sizes and headcount out of precaution. This has the potential to make getting a job in venture harder than it’s been in the past decade.

In order to help today’s VC candidates navigate this increasingly challenging environment, we’ve pulled together an updated version of our resources on how to break into and thrive in venture capital. We hope our collective learnings in this edition will help you find success in your search and first year(s) on the job!

Deck: Breaking Into Venture

  • Questions to ask before you start your search
  • Navigating your search

Deck: Navigating Your First Year in VC

  • Become invaluable to your firm for deal sourcing
  • Be known for high quality diligence
  • Learn as much as you can
  • Be a team player

Please share these resources with anyone you think may benefit from them! If you have any feedback, please don’t hesitate to reach out to the team at or!



Cowboy Ventures
Cowboy Ventures

A seed-stage focused technology fund backing exceptional founders.