The Skip podcast
Nikhyl Singhal
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Top 10 The Skip podcast Episodes
Goodpods has curated a list of the 10 best The Skip podcast episodes, ranked by the number of listens and likes each episode have garnered from our listeners. If you are listening to The Skip podcast for the first time, there's no better place to start than with one of these standout episodes. If you are a fan of the show, vote for your favorite The Skip podcast episode by adding your comments to the episode page.
Ready to start a startup? | Shreyas Doshi (Former PM leader at Stripe, Twitter, Google)
The Skip podcast
11/18/24 • 66 min
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 [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
02/27/25 • 50 min
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We tackle a listener’s question about whether to stay in their current job or take a new one. Using a 5-factor framework, we break down how to evaluate career decisions based on compensation, skills, lifestyle, long-term success, and work environment. Whether you’re considering a career move now or just want a structured way to assess future opportunities, this episode offers a practical guide to making confident job decisions.
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Key topics:
- The Stay vs. Go framework for career decisions
- How to assess if your job is career additive
- Balancing comp, skills, and lifestyle in job choices
- The probability of success matters in career moves
- How long you should stay before making a switch
- And much more
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Where to find Carly:
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Where to find Nikhyl:
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Find The Skip:
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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) The 5-factor framework
(01:20) Mailbag question: “Should I stay or go?”
(03:38) Is your job career additive?
(09:52) Why tenure matters less for some people
(15:51) Framework overview
(17:21) How to think about compensation
(21:28) Fishing for outlier comp offers
(23:54) Don’t just optimize for comp
(25:46) What skills are you picking up
(30:09) How esoteric are your skills
(32:37) Weighing up lifestyle
(36:56) What’s the probability you will succeed?
(42:03) Think about the environment you thrive in
(44:54) Final advice
The Skip podcast trailer
The Skip podcast
01/09/23 • 4 min
The Skip Podcast helps tech professionals get ahead in their career. It’s hosted by Nikhyl Singhal, a successful founder, head of product, and executive. He has helped scale four of the most successful tech products ever: Facebook, Credit Karma, Google Photos, and Google Hangouts. And he coaches more than 100 executives, managers, and rising stars in navigating important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life.
So subscribe to this podcast to hear from him and other executives as they teach unique career lessons.
09/10/24 • 75 min
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:
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 [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
Navigating careers while expecting
The Skip podcast
08/21/24 • 12 min
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.
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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
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Referenced:
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Where to find Nikhyl:
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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, 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
4 secrets of career-boosting companies
The Skip podcast
08/29/24 • 20 min
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.
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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
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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:
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, 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
Mastering your 30 second resume
The Skip podcast
09/20/24 • 53 min
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:
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 [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
Shedding perceptions: Moving from lone wolf to team player
The Skip podcast
02/11/24 • 33 min
In my fourth live coaching session, this caller felt like they had earned an unfair reputation as someone who struggles with collaboration in the workplace. The caller wanted guidance on transforming past perceptions into a new reality.
The caller reveals both their superpower and its shadow. They are an opinionated product manager, blessed with exceptional taste and intuition. However, these traits also lead them to resist compromise. We confront the caller’s shadow, and explore frameworks and strategies essential for effective collaboration.
Privacy is paramount for these calls, so we have anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.
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In today's episode, we discuss:
- How to shed poor perceptions in the workplace
- Navigating organizational power dynamics
- The up/down/across model of collaboration
- When and how to compromise
- Why 0 to 1 doesn’t exist in big tech
- How to use the founder mindset in a large org
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Timestamps:
(00:00) Introduction
(01:56) Caller context
(05:02) Caller’s reputation as a “rebel leader”
(07:11) How can I change people’s perception of me?
(08:37) Nikhyl’s response
(12:05) What the caller wants to avoid
(13:09) Nikhyl outlines two choices
(15:12) Should I optimize for short or long-term career wins?
[00:15:41] Nikhyl’s advice on risk and reward
(17:38) Should I leave big tech and become a founder?
(19:25) Nikhyl’s notes on compromise
(20:57) Should I play organizational Game of Thrones?
(21:45) Nikhyl’s recommendation
(25:39) Key takeaways from today’s episode
(33:03) Key links for this podcast
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Where to find Nikhyl:
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Where to find The Skip Podcast:
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Don't forget to subscribe to The Skip to hear Nikhyl teach unique and timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.
Stage of company: a career unlock
The Skip podcast
07/30/24 • 44 min
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:
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.
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
01/30/25 • 55 min
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We dive into a listener's question about multiple tech job offers, and compare three compensation packages. We break down tactics for negotiating comp while exploring how to pick a role that aligns with your superpower. Whether you're actively job hunting or looking to understand tech compensation better, this episode offers practical insights for making informed career decisions.
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Key topics:
- Why chasing comp early hurts career growth
- Comparing job offers
- Breaking down key components of total comp
- Ensuring you can exercise your shares
- When and how to discuss salary expectations
- Much more
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Referenced:
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Where to find Carly:
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Where to find Nikhyl:
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Find The Skip:
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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) Tactic for negotiating comp
(01:54) Unpacking the mailbag format
(03:09) Three job offers: which one should I take?
(06:02) Understanding bonus structures
(09:32) Why equity still matters today
(17:38) Breaking the equity exit trap
(25:29) Equity versus your market rate
(30:37) Don't chase comp early on
(34:12) Aligning the role to your superpower
(37:47) Negotiating comp: Start with what matters most
(47:30) When to discuss salary
(51:49) Problems with averaged comp
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FAQ
How many episodes does The Skip podcast have?
The Skip podcast currently has 37 episodes available.
What topics does The Skip podcast cover?
The podcast is about Career, Cmo, Entrepreneur, Entrepreneurship, Business Strategy, Podcasts, Tim Ferriss, Ceo, Business, Cfo and Careers.
What is the most popular episode on The Skip podcast?
The episode title 'Founder Mode, done right | Shreyas Doshi (ex-Stripe, Twitter, Google, Yahoo)' is the most popular.
What is the average episode length on The Skip podcast?
The average episode length on The Skip podcast is 42 minutes.
How often are episodes of The Skip podcast released?
Episodes of The Skip podcast are typically released every 20 days.
When was the first episode of The Skip podcast?
The first episode of The Skip podcast was released on Jan 9, 2023.
Show more FAQ
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