Alex MacCaw is the founder of Clearbit and Reflect, and his journey with each company has been wildly different. Clearbit took more of a “classic” startup approach — raising VC money, hiring hundreds of people, and working from an office in SF.

In 2020, he charted a new course by replacing himself as CEO at Clearbit, selling all his possessions and living full-time on a sailboat in the Atlantic. And now he’s building his new company Reflect in with a totally different approach — building a fully remote & asynchronous “lifestyle” company that decidedly eschews VC money and the other common hallmarks of a tech startup.

Alex shares everything he’s learned as a founder and why he believes building startups should not be one-size-fits-all.

Blake and Alex talk through:

(7:07) Pros/Cons of being asynchronous by design

(09:01) Why Alex doesn’t believe in remote work for large companies

(10:11) Remote work pitfalls

(14:24) When to replace yourself as CEO

(15:41) How to find your zone of genius

(18:32) When do startups hire a CFO or COO?

(21:16) #1 piece of advice for founders

(24:15) Things to know before you found a startup (B2B vs. B2C)

(27:29) Why build an indie software company

(28:28) When startups should (or shouldn’t) raise venture capital

(29:40) How Reflect started crowdfunding

(39:15) What AI and ChatGPT is good for

(44:09) Best time to start a company

(51:45) Not all startups need VC funding

(52:51) Advice for VCs from a founder

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Alex MacCaw, CEO and Founder of Reflect

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