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 Mentioned in this episode: Sign up for OpenView's weekly newsletter Alex MacCaw, CEO and Founder of Reflect LinkedIn Twitter Subscribe to Blake Bartlett on YouTube. Podcast produced by OpenView. View our blog for more context/inspiration. OpenView on Linkedin OpenView on Twitter OpenView on Instagram OpenView on Facebook