RBFN Podcast
Learn from the best alternative capital investors in the world. Revenue-based financing investor and thought leader, Keith Harrington, conducts in-depth interviews with other investors who are disrupting the capital markets by offering alternative capital solutions to the traditional VC equity fundraising path. Successful entrepreneurs are demanding more innovation from investors, and Keith’s goal is to bring these investors together to share what they’ve learned, why it’s important to them, and how they apply it to what they do. The Revenue-Based Financing Network Podcast aims to quickly expand this growing industry to support more entrepreneurs and build awareness around the revenue-based financing ecosystem. Learn more and join our community at www.rbfn.org.
RBFN Podcast
#26 - Entrepreneurship is Not Always Unicorns and Rainbows - Part 1 with Chris Costello, Founder and Former CEO of Blooom
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
Chris: LinkedIn | Morgan Stanley | Chris’s Finovate Best of Show