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
Popular Podcasts
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Special Summer Offer: Exclusively on Apple Podcasts, try our Dateline Premium subscription completely free for one month! With Dateline Premium, you get every episode ad-free plus exclusive bonus content.
The Breakfast Club
The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!
Crime Junkie
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.