June 11, 2024
New Podcast Episode: Entrepreneurship is Not Always Unicorns and Rainbows - Part 1 with Chris Costello, Founder and Former CEO of Blooom
Happy Tuesday, friends! Today I’m really excited to introduce you to an old friend of mine (I’ve known him for 30+ years!), who also happens to be an incredible entrepreneur. This is the first of a two-part conversation with him. Chris Costello co-founded two successful companies. One of them is a bricks-and-mortar, traditional wealth management company called The Retirement Planning Group. The other is a fintech called Blooom, which attracted VC from world-class investors like QED and Commerce Ventures. He’s done a lot in his career, achieved incredible success, endured unbelievable difficulty, and has come out the other side ready to share the lessons he learned along the way. I think his experience is totally unique, in that he is one of the few people I know who can legitimately share wisdom from multiple entrepreneurial paths. He’s done the bootstrapped thing, and he’s done the high-growth VC route. In today’s episode, we cover:
Bootstrapping versus VC-backed - the entrepreneur’s experience.
What he learned fundraising from world-class VCs and how investors should engage with founders.
How he navigated Blooom to an acquisition through multiple term sheets that fell apart in a very difficult market.
What it’s like to be a VC-backed CEO.
What happens when investors don’t act in good faith.
Tune in and give it a listen here!