Startups For the Rest of Us

Episode 614 | Deciding When to Quit Your Day Job, Founder Anxiety, and More Listener Questions


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In episode 614, Rob Walling chats with fan favorite Derrick Reimer. They start out by talking about Derrick’s decision to take a sabbatical from The Art of Product podcast after co-hosting it with Ben Orenstein for more than 5 years. Then, they answer a handful of listener questions, including when to quit your day job to focus on your startup full-time, coping with anxiety as a second-time founder, and choosing a domain name.

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Topics we cover: 

[2:18] Derrick’s decision to take a break from The Art of The Product podcast 

[10:22] When should you go full-time on your startup? 

[17:20] Before looking for tech firms, should I know the best frontend and backend architecture for my SaaS MVP and then only shop for firms who specialize in that?  

[24:13] I'm starting a new SaaS business, and despite a previous successful experience, I can't stop feeling extremely anxious about it. Is this something you're familiar with? How did you deal with it?

[30:34] When choosing a domain name for my startup, should you go with a meaningful and expressive name, but a less serious TLD.io or a somewhat fictional name combined with the best tld.com?  

Links from the Show:
  • Derrick Reimer @derrickreimer I Twitter 
  • SavvyCal
  • The Art of Product 
  • Bootstrapped Web 
  • Summit 
  • TinySeed 
  • Bullet Train 
  • MicroConf Connect 
  • The Entrepreneur’s Guide to Keeping Your Shit Together: How to Run Your Business Without Letting it Run You
  • The Mom Test 
  • How I Nabbed The .Com for My Bootstrapped Startup Without Spending a Million Bucks
  • Lean Domain Search 
  • The Bootstrapper’s Guide to Outside Funding 
  • If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.

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    Startups For the Rest of UsBy Rob Walling

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