11 May 2022 |

S2 E2: Henry Yoshida, CEO at Rocket Dollar | Fintech Founder | Retirement



  1. Two Types of Parents: 1:40
  2. Learning to Play by The Rules: 3:29
  3. How to Succeed: 5:41
  4. The A-ha Moment: 9:44
  5. Finding Belonging: 13:38
  6. Shaping Who You Are: 18:54
  7. Smart People Have Imposter Syndrome: 22:52
  8. Expanding Investment Potential: 33:21

Why Henry Yoshida is Re-Writing The Rules With Fintech

“So I had grown up my entire life wanting to be a lawyer, thinking that the best way to know the rules is to study it and then be the person that actually writes those rules.” Henry Yoshida, CEO Rocket Dollar

Growing up, Henry believed successful people won because they knew the rules. Now he’s rewriting those same rules, making sure more people win when it comes to retirement investment.

Retirement is a hot topic and how we invest and prepare for it is crucial. Through his company, Rocket Dollar, Henry has created a platform that lets people invest tax-advantaged retirement dollars into private alternative investments, like venture capital and crypto.

Henry knows what it’s like growing up outside the dominant culture, what it felt like working in traditional firms like Merrill Lynch, and why sometimes you need to be the change you want to see.

Bright Beginnings

As the son of Japanese immigrants, Henry felt a sense of being an outsider growing up. But that was not the only lesson he learned. His hard working parents strived to ensure Henry played the sports he wanted to play, never missed a school trip, and took care of all their staff and families at the restaurant they ran.

From an early page, Henry recognized the power of money had on bringing freedom and stability to people’s lives and how playing by the rules was only part of the solution.

“As a citizen in the United States, you do these things. You save in your 401k. You can help you, you spend below your means. You don’t get too much indebtedness and so forth.”

The A-ha Moment

Knowing his family would struggle in retirement without the right investment opportunities, Henry realized it was time to make the world of smart investment investment in alternatives way more open. Helping those  who felt on the outside of finance find belonging and more importantly, security.

After a successful career at Merrill Lynch, and taking everything he’d learned and experienced, Rocket Dollar was born.

And Henry remembers the exact moment he knew he was exactly where he was meant to be. A conversation with a potential customer opened his eyes to the fact he was helping people make decisions in their 20s, that would impact their lives for the better in decades to come.

“I thought that’s a heck of a lot better than the normal expected path of a typical Merrill Lynch financial advisor, which would have been to help wealthy people become wealthy or. And so forth. And that’s when I knew that I’m going to keep doing this path.”

The Future Looks Bright For Rocket Dollar

Expansion is the number one priority for Rocket Dollar as the company continues to grow apace. More choice, more features, and more capabilities.

Even more than that, the company is committed to being as useful to its potential clients as possible, and you can expect to say an increasing volume of inspiring, helpful content from the Rocket Dollar team over the months to come.

Follow Henry:

LinkedIn: linkedin.com/in/henryyoshida

Twitter: twitter.com/henryyoshida

You can keep up-to-date with everything Humans of Fintech at https://workweek.com/brand/wtfintech/

And if you’ve enjoyed Humans of Fintech why not try: Chicks of FinTwit, Tech Unlocked, Breaking Banks or Fintech Insider