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:

• Twitter/X
• LinkedIn
• YouTube

Where to find Nikhyl:

• Twitter/X
• LinkedIn

Find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
• TikTok

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