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July 5, 2022

E7: How to Sell Your Company to Goldman Sachs w/ Henry Yoshida

E7: How to Sell Your Company to Goldman Sachs w/ Henry Yoshida

Henry is CEO and Co-founder of Rocket Dollar, a web platform that lets people invest tax-advantaged retirement dollars into private alternative investments. 

He is a Certified Financial Planner™ professional, licensed Realtor®, and has 20 years of experience in finance. 

In the past, Henry was the founder of venture-capital-backed Robo-advisor Honest Dollar (acquired by Goldman Sachs), was the founder of MY Group LLC ($2.6B AUM retirement plan advisory firm), and spent 10 years at Merrill Lynch. 

He graduated from The University of Texas at Austin, has an MBA from Cornell University, and lives in Austin with his wife and two daughters.

We talked about Henry's journey of being a multi-founder, and what is it like for his company to be acquired by Goldman Sachs and now become Goldman Sachs Marcus. Advice for founders on whether to raise or explore exit strategies and many more interesting prospects!

Episode timestamp:

0:33 Introduction
1:55 How Henry got into the world of entrepreneurship
11:31 A founder's journey: from employee to CEO
13:22 Working in traditional finance vs. working in fin-tech
15:01 When's the best time to start a startup in someone's career
16:24 Multi-Founder Mindset: lessons from building 3 startups
18:41 When should founders think about acquisition vs. continuously raising
22:25 A founder's decision: bootstrapping, raising growth rounds, weighing the decisions on acquisition/merger, IPO.
24:58 Who should founders talk to to get advice on a potential acquisition
26:20 Henry's personal experience on his recent exit
29:30 Approaching the board about a potential acquisition
31:38 What to do when a potential acquirer is interested
33:21 Founder-investor: angel investing while being a founder
37:36 Why not raise more capital? Potential problems with over-raising