$170M Founder Yoshi Yokokawa (Alpaca) on 2008 Crash, Diversification Myths, Day Trading and Burnout

Yoshi Yokokawa, co-founder and CEO of Alpaca, joins Personable with Harvey Bracken-Smith. Alpaca is a leading brokerage infrastructure and self-clearing fintech powering over 7 million brokerage accounts across 40 countries and backed by more than 170 million dollars in funding.

Before building Alpaca, Yoshi began his career at Lehman Brothers, experiencing the rise and fall of one of the most famous investment banks during the 2008 financial crisis. He went on to become a day trader, founded machine learning startups, and ultimately created Alpaca, a company redefining how global investing is built through APIs.

In this episode, Yoshi shares how he learned from both the boom and the collapse of global markets. He discusses why every generation forgets financial history, why real diversification fails in downturns, and how to stay grounded while raising hundreds of millions of dollars. Yoshi reflects on founder-market fit, emotional resilience, and what it means to build something that gives others financial freedom, the goal he has chased since childhood.

In this episode, Yoshi Yokokawa discusses:
◽️ What it was like working at Lehman Brothers during the 2008 crash
◽️ Why diversification is often a myth in real crises
◽️ Lessons from day trading and "street fighting" in the FX markets
◽️ How machine learning led to the creation of Alpaca
◽️ The realities of raising 170 million dollars in venture capital

⏱ Timestamps
00:00 Intro
05:00 Lehman Brothers culture in Japan
07:30 Early signs of the 2008 crisis
10:00 Bubbles, hedging limits and market behavior
12:30 Retail investors and emotional decision making
15:00 Why hedging depends on local context
17:30 Leaving banking and moving into day trading
22:30 Probability, discipline and trading mindset
25:00 First software attempts and meeting technical friends
30:00 What an API is and why it matters
32:30 Licenses, compliance and protecting customer assets
35:00 Raising 170 million and dealing with dilution
37:30 Convincing VCs and founder market fit
42:30 Japan vs Silicon Valley
45:00 Expanding financial access around the world
47:30 Hiring philosophy and values
50:00 Personal investing style and risk approach
53:00 Burnout, limits and staying balanced
56:00 Legacy, family and long term thinking
58:00 Final reflections
1:08:00 Outro

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📌 Resources
Yoshi Yokokawa:
◽️ LinkedIn: https://www.linkedin.com/in/yoshiyokokawa/

Harvey Bracken-Smith:
◽️ LinkedIn: https://linkedin.com/in/harveybracken-smith
◽️ Instagram: https://instagram.com/harveybsmith
◽️ X (Twitter): https://x.com/harveybsmith_
◽️ Newsletter: https://personable.substack.com/
◽️ Website: https://www.personable.media/

Personable Podcast:
◽️ Instagram: https://instagram.com/personable.podcast
◽️ LinkedIn: https://linkedin.com/company/personablepodcast
◽️ TikTok: https://tiktok.com/@personableclips
◽️ Spotify: https://open.spotify.com/show/7JOTYDER6m2FDrlhop4api
◽️ Apple Podcasts: https://podcasts.apple.com/us/podcast/personable/id1671640111

Additional:
◽️ The Draft (Sign up): https://thedraft.io
◽️ Fundraising: https://justgiving.com/crowdfunding/LouLouRacefoiundation?utm_term=PvByaxmdn

Personable is a podcast dedicated to helping listeners become the best they can be by learning from the world’s best in their respective fields. This mission is inspired by my mother, Louise, who encouraged me to become the best version of myself before she passed away from cancer in 2023. 

This content is for informational and entertainment purposes only and is not financial advice. Always consult a qualified financial advisor before making investment decisions. Investing involves risks, and pas