I'm joined by product leader turned founder Shreyas Doshi to discuss the founder's journey and when starting a company might be the right move for you. We challenge common startup wisdom and explore why traditional career advice often misses the mark for aspiring founders.

Key topics:

Which PMs are secretly great founder material
Red flags: when founding isn't for you
The right time to start your company
Key skills that set you up for success
Thriving in ambiguity
Debunking the "venture scale or bust" mindset
The counterintuitive way to avoid burnout
Much more

Referenced:

4 questions Shreyas wished he’d asked himself sooner: https://www.youtube.com/watch?v=atS060bNpE0&t=698s
Avoiding burnout for high achievers: https://www.youtube.com/watch?v=5Iwymgai-ZM
Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=928s
Improving your product sense: https://maven.com/shreyas-doshi/product-sense
Is my next job at a startup or big tech?: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053s
Managing your PM career in 2025 and beyond: https://maven.com/shreyas-doshi/product-management-career?utm_source=lenny
Nikhyl’s career advice highlights at Lenny’s Summit: https://www.youtube.com/watch?v=rujK7HvD6es&t=124s
Stage of Company: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053s

Where to find Shreyas:

Where to find Nikhyl:

Find The Skip:

Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community

Timestamps

(00:00) Teaser: Why average PMs can make great founders

(01:17) Introduction

(02:34) The essential first step before founding

(06:21) Successful founder traits

(10:48) Managing at scale vs managing uncertainty

(18:25) Thriving in ambiguity

(21:29) Red flags: when founding isn't for you

(23:34) The surprising link between average PMs and founding success

(25:51) Building better product sense

(29:35) The right time to start your company

(37:03) Beyond venture scale: rethinking startup success

(44:26) A guide to avoiding burnout

(49:23) The real truth about big tech working hours

(52:27) Why taking a "demotion" might be a good move

(58:45) Learn more: Shreyas' Product Sense course

(63:15) Key takeaways

(65:22) Get in touch with Nikhyl

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

Ready to start a startup? | Shreyas Doshi (Former PM leader at Stripe, Twitter, Google)

The Skip Podcast

Ready to start a startup? | Shreyas Doshi (Former PM leader at Stripe, Twitter, Google)