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

13 snips

Aug 2, 2022

Derrick Reimer, an experienced podcaster who co-hosted The Art of Product, shares insights into his recent sabbatical and the challenges of podcasting. The discussion pivots to practical advice, illuminating the tricky decision of when to leave your day job for a startup. Derrick also addresses the overwhelming anxiety that many second-time founders face and shares strategies for managing stress. Plus, they tackle the importance of choosing the right domain name for your business, balancing desirability with practicality.

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ANECDOTE

Derrick's Podcast Sabbatical

Derrick Reimer co-hosted The Art of Product podcast for over five years.
He decided to take a sabbatical due to feeling constrained and stagnant.

ADVICE

When to Go Full-Time

Model different financial scenarios to determine when you can go full-time.
Consider factors like risk tolerance, runway, and potential backup plans.

ADVICE

Choosing a Tech Stack

Choose popular tech stacks like Ruby on Rails, Python/Django, or Laravel for your MVP.
Prioritize monolithic architecture for faster iteration and easier maintenance.

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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:

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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