Alex MacCaw (@maccaw) talks living on a boat, quitting his own 7-figure company, starting over with a lifestyle business, whether free will exists, crowdfunding from your own customers, and gaining a foothold in a crowded market with Courtland (@csallen) and Channing (@ChanningAllen).

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

Alex MacCaw is the founder of Reflect, a note taking app which he’s grown to $20k MRR with a team of 4. Previously, he was the co-founder of Clearbit, a VC-backed company that scaled to $50m in revenue. After stepping down as CEO of Clearbit, he decided to focus on doing the stuff he enjoys. So he’s sailing around the world building an app that gets him excited every day.👉 My side project, Whitstable Craft Co.What we covered in this episode:Why Alex dropped out of schoolCoding without a CS degreeBeing unemployableStarting ClearbitStepping down as CEO of ClearbitBoostrapping ReflectWhy another note taking app?Building what you enjoyGrowing to 20k MRRGetting the first users for your productSailing around the worldRecommendationsBook: Isaac Asimov's Guide to Earth and SpacePodcast: In Our TimeIndie Hacker: Adam WathanFollow AlexTwitterMy linksTwitterIndie Bites TwitterIndie Bites YouTubeJoin the membershipPersonal Website2 Hour Podcast CoursePodPanda (hire me to edit your podcast)This Indie Life PodcastSponsor - AhrefsThank you to Ahrefs for sponsoring Indie Bites. Ahrefs is the most complete and valuable SEO tool on the market. Bootstrapped companies such as VEED and Transistor have used Ahrefs extensively to understand how to craft their SEO strategies, which have been such a pivotal part of their growth.If you want to get more traffic from Google on your side-project, I’d recommend first trying out Ahrefs Webmaster Tools for free. You’ll see what keywords your pages are ranking for, understand how Google sees your content and discover what changes you need to improve your search ranking. You should also check out their YouTube channel to understand both the basics of SEO and some more advanced techniques.To try out Ahrefs Webmaster Tools, head to ahrefs.com/webmaster-tools