June 25, 2024

New Podcast Episode: Fake It Until You Make It - How to Raise Capital with Chris Costello, Founder and Former CEO of Blooom

Happy Tuesday, friends! Today we release part 2 of my conversation with my old friend, Chris Costello, former CEO and founder of Blooom and TRPG, now founder of Curtis Capital Advisors. Today’s conversation focuses entirely on the lessons Chris learned raising capital from some of the best VCs in the business, and the tactics and hacks he wishes he knew when he started. Chris shares the lessons that in retrospect he wishes someone shared with him, but that are a complete mystery to anyone launching their first startup and raising equity capital. This is an incredibly helpful and tactical conversation that will help any entrepreneur raising any kind of capital. I think it’s a must listen for investors too for two reasons. First, hear what it’s like on the other side of the table. Second, the advice shared in this episode applies to raising ANY kind of capital, not just venture capital. I use many of these concepts to raise VC, debt facilities, and more. We’ll cover:

  • Raising money is sales. Get used to it. If that feels dirty or funny to you, you’re going to have to get over it.

  • Getting your mindset right for raising capital.

  • Why belief and mission are critical.

  • How to ask the right questions when talking to investors.

  • Developing a relevance filter for advice.

  • Getting referrals from and to VCs.

  • How to think about how much capital you need to raise.

  • How to get investors to an answer quickly, and how badly the slow maybe sucks.

  • Managing investors during diligence and closing.


We cover so much in this conversation, and I think you’ll enjoy and learn a lot from both the wide range of topics and the tactical advice shared. Listen here and learn!