Alex MacCaw (Clearbit & Reflect): Everything I’ve Learned as Startup Founder

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(14:21) When to replace yourself as CEO(15:52) How to find your zone of genius(18:31) When do startups hire a CFO or COO?(21:14) #1 piece of advice for founders(24:14) Things to know before you found a startup (B2B vs. B2C)(27:27) Why not raise venture capital(28:28) When startups should (or shouldn’t) raise venture capital(29:40) How Reflect started crowdfunding(39:14) What AI and ChatGPT is good for(44:13) Best time to start a company(46:20) Not all startups need VC funding(47:16) Advice for VCs from a founder