0:00
/
0:00
Transcript

What I learnt this week

From a simple API to powering the next generation of investing apps. Yoshi’s lessons on raising capital, building a remote-first culture, and choosing hard mode.
1
1

What I Learned This Week: Building Alpaca with Yoshi

This week I sat down with Yoshi, co-founder and CEO of Alpaca, one of the most inspiring founders I know. We spoke founder-to-founder about his journey: starting from an idea, raising capital, managing investors, scaling globally, building culture, and the realities of running a fully remote fintech.

We recorded it in my home after lunch, and it turned into a candid conversation on what it really takes to build the B2B version of Robinhood.

Thanks for reading! Subscribe for free to receive new posts and support my work.

What We Covered

  • How Alpaca started as a simple developer API

  • The evolution into full brokerage infrastructure

  • Raising capital in different market cycles

  • Managing a board as an extension of your team

  • Why they went all-in on remote and never looked back

  • How to actually use investors beyond capital

  • The “hard mode” approach to tough decisions

  • Why culture is an output, not an input

  • Adapting between founder and CEO


Key Insights

1. Start with the first real problem you can solve.

“Stock brokers just didn’t have an API, so we built one.”

Alpaca didn’t start by trying to be a global brokerage. It started by giving developers a simple API to buy and sell stocks. That initial wedge grew into full-stack infrastructure.

2. Fundraising is a different game at every stage.
From YC seed days to Series C, Yoshi’s approach shifted:

  • Seed: underestimated the value of the right investors over the highest valuation.

  • Series A: raised right after the pandemic, driven by early demand.

  • Series B: peak fintech boom, structured 2-week processes.

  • Series C: relationship-driven, more flexible, slower pace.

“What I learned is the priority changes. Early on, it’s guidance and building. Later, it’s revenue growth and market access.”

3. Your board is part of your team, if you treat them that way.

“I expect each board member to contribute, bringing clients, talent, new business. They’re key team members.”

He spends time understanding each board member’s style and intentions, even when their feedback is extreme, to find the “neutral” insight.

4. Remote works if you go all-in.
Alpaca went 100% remote during the pandemic and never returned. The turning point: seeing how hybrid made remote employees second-class.

“The middle is not acceptable. It creates first-class and second-class employees.”

5. Ask investors for more than money.
Yoshi constantly uses investors for data, warm intros, and market benchmarks.

“I don’t want to pay for consultants. Investors should help us for free.”

6. Decision-making hack: choose the harder path.
When stuck between two or three options, they pick the toughest one.

“If we’re stuck between two or three options, we pick the most difficult one. The outcome tends to be better.”

“It’s funnier to choose hard mode. And the outcome tends to be better.”

7. Culture = values + execution.

“Values are the input, culture is the output. Execution is firing when values aren’t lived, and promoting when they are.”

8. Founder vs. CEO is situational.
He shifts between “wartime founder” and “peacetime CEO” depending on the cycle.

“What’s most difficult is the middle, deciding whether to push hard or stay polished.”


Highlight for me

The “choose the harder path” philosophy hit me. It explains why Alpaca ended up tackling full-stack infrastructure instead of staying a lightweight API provider.

And the way Yoshi manages his board is exceptional.


Listen to the full conversation for more on how Yoshi built Alpaca, scaled globally, and kept true to his values while raising over $150M.

Thanks for reading! Subscribe for free to receive new posts and support my work.

Discussion about this video

User's avatar