#26 - Entrepreneurship is Not Always Unicorns and Rainbows - Part 1 with Chris Costello, Founder and Former CEO of Blooom

RBFN Podcast

Chris Costello is the founder and former CEO of Blooom, an innovative digital robo advisor. Chris is a rare entrepreneur who built both a bricks-and-mortar company and a technology business. In this first episode of our two-episode chat, Chris first talks about starting his entrepreneurial journey in 2004 by co-founding The Retirement Planning Group, an independent wealth management firm. Over the next decade, the firm flourished under his leadership managing over $1 billion in assets. In 2013, Chris co-founded Blooom to help people better manage their 401k investments. He discusses the challenges of fundraising as an entrepreneur, navigating multiple failed acquisition deals, winning Best of Show at Finovate, and Blooom's eventual sale to Morgan Stanley in 2022. Chris shares some invaluable advice about raising venture capital through his experience pitching over hundreds of times.

Key Takeaways

[4:41] Starting the Retirement Planning Group.

[7:42] Learning sales and phone skills in the boiler room.

[8:10] Chris’s conversation rate back in the day.

[9:16] Teaming up with Kevin Conard.

[10:08] Building a niche in retirement planning.

[14:20] Starting Blooom and the biggest challenges.

[18:05] Meeting up in Randy’s basement to discuss the initial ideas of Blooom.

[22:31] What made Blooom so special

[25:52] Funding Blooom’s initial development.

[26:40] Winning Best of Show at Finovate.
[29:04] Chris is in the “100 Club”.

[30:30] Landing QED.

[32:04] The decision to go down a new path.

[33:54] Getting referrals from uninterested VC’s.

[35:35] Fundraising strategies for startups.

[36:18] Fundraising under the gun.

[40:53] CEO transition.

[43:34] Taking back the CEO role in 2019.

[44:11] Lessons learned from being abruptly left at the altar by an acquirer.

[57:47] Selling to Morgan Stanley in 2022.

[1:00:29] Advice for raising capital.

[1:07:02] Three things a good investor should help with.

Resources:
RBF Network
Keith’s Twitter

Keith’s Linkedin

Novel Capital

Chris: LinkedIn | Morgan Stanley | Chris’s Finovate Best of Show