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 [email protected]

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

Welcome to a special episode featuring key moments from my presentation at the very first Lenny and Friends Summit in San Francisco. In this talk, I've distilled the most valuable career insights I've gained from coaching product managers and creating PM content over the past 12 months. In this highlight reel of career advice, I discuss:

• Rethinking retirement
• The career-defining question every leader should ask
• Power years versus foundational years
• Leveraging career stories
• Finding peak roles
• Understanding the shadow of your superpower
• The relationship between personal brand and reputation
• Breaking down burnout
• Building your support network through Skip Community

–

Referenced:

• Mastering your 30s career resume
• 4 secrets of career boosting companies
• Avoiding burnout for high achievers
• Battling job search anxiety
• Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive)
• Crafting a compelling career story
• JZ: https://www.linkedin.com/in/jiaona/
• Shadows of your superpowers (Part 1)
• Shadows of your superpowers (Part 2)
• Shedding perceptions: Moving from lone wolf to team player
• Six superpowers of product managers
• Stage of company: A career unlock
• The art of building your personal brand

–

Where to find Nikhyl:

• Twitter
• 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 [email protected]

–

Timestamps:

(00:00) How to help the Skip community

(01:37) Lenny’s Summit

(04:10) Breaking your career into levels

(07:33) Crafting a compelling career story

(10:26) All elite PMs find “peak roles”

(12:15) “The reputation you build today is the brand you’ll have tomorrow”

(13:17) Avoiding burnout

(16:13) Knowing the shadow of your superpower

(18:13) Don’t build a career alone

(18:53) Summary of advice

(20:19) Special announcement

A great career story can accelerate growth, yet most struggle to craft one. Even top performers fall short, telling stories that are overly detailed, abstract, jargon-filled, or poorly structured – all of which can lose a listener's interest.

The first 30 seconds are crucial; you need to hook your audience quickly. Think of the beginning of your story as a movie trailer: highlight the most engaging aspects rather than chronologically detailing every event.

This episode focuses on crafting a captivating 30-second introduction to your career story that engages listeners and enhances your professional profile. We've taken a unique approach by inviting Skip community members to submit their career stories for a live workshop. You'll hear real examples of me coaching engineering and product leaders, demonstrating the transformation from initial attempts to polished and punchy narratives.

We also discuss:

• Common storytelling mistakes that everybody makes
• Techniques for weaving a theme into your story
• Effective strategies that will hook listeners
• Adapting your story for various audiences and situations
• Balancing between brevity and showcasing your unique value

Referenced:

• Crafting a compelling career story
• Founder Mode, done right with Shreyas Doshi

Where to find Nikhyl:

• Twitter
• 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 [email protected]

Timestamps

(00:00) Episode teaser: Mastering your 30s resume

(01:15) Common mistakes everybody makes

(09:42) Why you need a 30s and 2m career story

(12:21) Showing the trailer, not the movie

(16:44) Example 1

(17:28) Thinking about story sequencing

(19:04) Example 2

(19:44) Avoiding detail

(21:21) Example 3 (before)

(21:54) Avoid abstract stories

(23:52) Example 3 (after)

(24:41) The art of thematic narratives

(28:29) Example 4 (before)

(29:18) Crafting a theme

(29:51) Example 4 (after)

(31:24) Avoiding jargon

(34:51) Tailoring communication tempo

(36:19) Example 5 (before and after)

(39:04) Example of a strong 30s resume

(41:13) Preparing multiple versions

(45:20) Nikhyl’s strong but generic resume

(47:50) Nikhyl’s deeper version

(50:57) How to submit your career story

(52:50) Get in touch with Nikhyl

In this episode, I’m joined by product and leadership expert Shreyas Doshi to dissect Founder Mode, why it’s appealing, and how to activate it. We dive deep into Paul Graham's recent essay which struck a chord in the tech community and resonated strongly with many founders and leaders.

We also discuss:

• Why founder mode is a mindset, not a title
• Whether founder mode is good or bad
• Balancing detail and delegation
• The importance of product sense and good judgment
• Mastering founder mode as a product leader
• Operational insights from Meta and Stripe

Referenced:

• Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=928s
• Paul Graham’s "Founder Mode": https://paulgraham.com/foundermode.html
• Shreyas’ Tweet on founder mode’: https://x.com/shreyas/status/1830767630917214318
• Six superpowers of product managers: https://www.youtube.com/watch?v=OnsSwHP3d-c
• Shreyas’ previous appearance on the podcast: https://www.youtube.com/watch?v=y_TnXtnY3QM&t=23s
• The 3 types of product leaders: https://x.com/shreyas/status/1375491623308550144

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 [email protected]

Timestamps

(00:00) Teaser: Unpacking founder mode

(02:47) What Shreyas has been up to

(04:04) Shreyas’ take on founder mode

(08:59) Why judgment and product sense is critical

(13:04) Balancing detail and delegation

(20:57) The key question for founders about ownership

(23:01) Not every company needs a CPO or Head of Product

(28:07) When product people should prioritize detail

(31:32) What everyone gets wrong about Steve Jobs

(34:22) Shreyas’ observation about John and Patrick Collison

(38:17) Nikhyl’s observation about Mark Zuckerberg

(40:05) Founder vs manager mode

(43:40) Should leaders avoid manager mode?

(48:17) Chase impact, not optics

(57:00) The 3 types of product leaders

(60:46) Aligning your environment, opinion, and superpower

(63:10) Shreyas’ non-consensus view on building product

(67:52) Mastering founder mode as a PM

(72:58) Getting in touch with Shreyas

(74:49) How to find Nikhyl

Not all successful companies can supercharge your career. And not all companies that struggle are bad for your career. How can you tell if your company, or one that you are consider, will supercharge your career? In this episode, we'll explore four key characteristics of career-accelerating companies: speed, market position, quality of talent, and development culture. Whether you're job hunting or evaluating your current role, these insights will help you identify environments that truly foster career growth.

–

We also discuss:

• Strong signals of a supercharged company
• Why shipping velocity is crucial
• Learning opportunities at immature companies
• Looking for companies with strong talent
• What makes an excellent development culture

–

Referenced:

• Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=913s
• Greatest hits on career advice with Peter Yang: https://www.youtube.com/watch?v=-BcCHEXAVVk
• Is my next job at a startup or big tech?: https://www.youtube.com/watch?v=MiELOo4_XGg&t=9s
• Should I join or leave an ex-hypergrowth company: https://www.youtube.com/watch?v=5-rr1cYYfEU
• Six superpowers of product managers: https://www.youtube.com/watch?v=OnsSwHP3d-c
• Stage of Company: A career unlock: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053s

–

Where to find Nikhyl:

• LinkedIn
• Twitter/X
• Threads

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, Twitter or email me at: [email protected]

–

Timestamps

(00:00) Episode Teaser: How to 10x your career

(01:10) Introducing the framework

(03:41) The caller’s question

(05:00) 1: Speed and execution

(08:43) 2: Market position

(11:47) 3: Quality of talent

(15:27) 4: Development culture

(20:22) How to get in touch

In this short and sharp "peacast" episode of The Skip, I share insights from a conversation with a pregnant Product Executive facing a career dilemma. She was convinced she needed to leave her current company, but while searching for a job, she got pregnant. And now she's been offered a new role at her company due to a reorganization. We discuss her options: accept the role, take a less senior role post-maternity leave, or seek opportunities elsewhere.

–

We also discuss:

• Maximizing career potential without sacrificing family
• Reframing career decisions in the context of long-term growth
• How to have it all, just not at once
• The value of wartime leadership experience
• Overcoming job search anxiety

–

Referenced:

• Avoiding burnout for high achievers

–

Where to find Nikhyl:

• LinkedIn
• Twitter/X
• Threads

–

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, Twitter or email me at: [email protected]

–

Timestamps

(00:07) Applying my career framework to the caller’s case

(02:13) Caller context

(02:52) Why one option is a “no-brainer”

(03:58) The value of wartime leadership experience

(07:43) Why you won’t regret choosing family > career

(09:53) The wisdom in “playing it safe”

(11:11) Key takeaways

(11:44) How to get in touch

Many product managers focus on brand names or job titles, overlooking a crucial factor: company growth stage.

This episode reveals how a company's phase - from startup to market leader - shapes your work and career path. We explore the four key growth stages, how product management evolves, and how to align your strengths with the right stage.

Featuring insights from seasoned product leaders, learn to identify your ideal company stage and navigate transitions. This episode is your guide to making strategic career moves in product management by leveraging the often-overlooked power of company growth stages.

We also discuss:

• The 4 stages of company growth: drunken walk, product market fit, hypergrowth, and established market leader
• How PM roles evolve across stages
• Matching your skills to each stage
• Intentionally choosing your company stage
• The value of diverse stage experience for successful PMs
• Strategies to gain multi-stage experience

Referenced:

• Stage of company, not name of company: https://theskip.substack.com/p/stage-of-company-not-name-of-company
• Shadows of your superpowers (Part 1): https://www.youtube.com/watch?v=XZbjvymjabA&t=912s
• Shadows of your superpowers (Part 2): https://www.youtube.com/watch?v=lcdb5enbDLE

Where to find Nikhyl:

• LinkedIn
• Twitter/X
• Threads

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.

Timestamps

(00:00) Intentionally choosing your company stage (episode teaser)

(01:25) The importance of company stage

(02:47) 3 common questions from PMs

(05:383) The link between PM and company stages

(07:48) The 4 company stages

(13:45) What’s unique about early-stage PMs

(15:24) How PM evolves when there’s customer traction

(18:00) Product management at a hypergrowth company

(21:50) One example of what changes between the first three stages

(24:49) PM at an established leader

(30:04) How to know which stage is right for you

(37:03) Spotting when it’s time for something new

(38:36) Choose your stage of company wisely

(41:38) Why top product people have multi-stage experience

(43:28) How to get in touch

Personal branding is a crucial yet often misunderstood aspect of career development. Many professionals mistake personal brand for self-promotion or social media showmanship.

This episode debunks these myths and reveals the true power of strategic personal branding. Featuring insights from two tech executives, Annie Pearl of Microsoft and Iska Saric of Meta, we pull back the curtain on how industry leaders craft and wield their personal brands to open doors, land dream roles, and shape their legacies.

The episode provides actionable strategies to build an authentic and compelling brand that catapults your career forward.

We also discuss:

• The critical distinction between reputation and brand
• Why you don’t need to become an influencer
• The power of ‘peak roles’ in accelerating your career
• Tailoring your brand story to specific audiences
• Strategies for expanding your professional network
• Navigating gender dynamics in personal branding
• The 30-minute per week method to brand-building

Referenced:

• Annie Pearl, CVP at Microsoft: https://www.linkedin.com/in/anniepearl/
• Iska Saric, VP of Communications at Meta: https://www.linkedin.com/in/iska-saric-97210212/
• Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=1078s

Where to find Nikhyl:

• LinkedIn
• Twitter/X
• Threads

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.

Timestamps

(00:00) Episode format

(02:14) Why brand matters

(04:47) Building a brand ≠ becoming an influence

(08:14) Reputation versus brand

(10:28) How to establish a reputation

(13:55) Leveraging professional connections

(18:08) The role that will transform your career

(24:12) Crafting and communicating your brand

(30:09) The "30-minute per week" method

(30:49) Navigating

(35:36) Key takeaways from this episode

(35:56) How to get in touch

Navigating job transitions in today's competitive tech landscape is difficult. Many people get stuck between roles, and an extended job search can dent your confidence. You might doubt your past achievements, question your current skills, and worry about what's next.

In today’s episode, we tackle job hunting in today’s tough market. I share insights from a real coaching session with a design leader who's struggling after being out of work for a few months.

The episode is packed with concrete tools, useful tips, and proven strategies to help you navigate a job transition.

–

We also discuss:

• The mindset needed when in between jobs
• Rebuilding your confidence from the ground up
• The role of grit and hustle in an extended job search
• How to run an effective job search
• Making the most of your time between jobs
• Transforming your mental, physical, and social game

–

Referenced:

• Avoiding burnout for high achievers
• Steve Jobs 2005 Commencement speech

–

Where to find Nikhyl:

• LinkedIn
• Twitter/X
• Threads

–

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.

–

Timestamps

(00:00) Episode teaser

(01:45) Navigating a job transition

(04:34) The caller’s crisis of confidence

(10:22) Nikhyl’s advice

(16:24) Several strategies for effective job searches

(17:53) Pro Tip 1: Set realistic expectations

(21:41) Pro Tip 2: Work on yourself

(28:04) Pro Tip 3: Treat your craft like an athlete

(30:40) Pro Tip 4: Don’t cut your search short

(34:50) Pro Tip 5: Run the process with grit and hustle

(41:33) Pro Tip 6: Take advantage of the US calendar

(43:55) Pro Tip 7: Don’t try to find the ‘perfect role’

(47:55) Pro Tip 8: Bet on yourself

(48:59) Key takeaways from this episode

(51:02) How to get in touch

Around 10-20% of my coaching calls tackle burnout. Despite being a deeply personal experience, burnout frequently affects high achievers, who often don't have the time to develop effective coping strategies.

In today's episode, we dissect several paraphrased conversations, drawing from years of career coaching experience, offering insights and practical advice to help you manage burnout, set healthy boundaries, and cultivate a resilient mindset.

–

In today's episode, we discuss:

• Why burnout is a deeply personal experience
• Insights on burnout from real-world examples
• Why burnout is a side effect of success
• Adopting a long-term career view
• The importance of finding a hobby
• Avoiding low-energy work

–

Referenced:

• Balancing Work and Life: Insights from Nikhyl and the Skip CPO group

–

Where to find Nikhyl:

• Twitter/X
• LinkedIn

–

Find The Skip:

• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
• TikTok
• This episode on YouTube

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/X.

–

Timestamps

(00:00) Why you resent your company

(01:35) People experience burnout differently

(04:52) Today’s episode format

(05:36) The mindset needed to enforce boundaries

(07:25) Observation 1: High performing companies will always push their best people

(11:45) Observation 2: Family planning will require you to rework the timing of your career plan

(17:23) Observation 3: Ambitious, overworked people will eventually resent their job

(23:21) Pro tip 1: Changing your mindset toward burnout

(24:58) Pro tip 2: Finding a hobby forces joy on your calendar

(29:00) Pro tip 3: Recognizing what drives low energy at work

(31:04) Key takeaways from this episode

(32:39) How to get in touch