The Skip Podcast

Latest Episodes:

Graduating Into Uncertainty? How to Actually Land Your First Tech Job Jul 09, 2025

Show notes

In this episode, I’m joined by my co-host Carly Malatskey to share the early-career playbook most people wish they had at 21. Whether you're fresh out of college, navigating your first job, or advising someone who is — this episode is for you.

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Key topics

• Why your first job should feel like a sprint, not a stroll

• How to tell if your job is setting you up — or holding you back

• The truth about internships (they matter more than your degree)

• How to stand out when applying — and why “spray and pray” fails

• Why it’s okay (even smart) to view your first job as a stepping stone

• Red flags and green flags once you’re hired

• How to network in a way that doesn’t feel transactional

• The mindset shift that separates top performers early in career

• Why working in-person still gives you an edge

• How to take real risks when you have the least to lose

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Where to find Nikhyl:

Twitter/X

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Where to find Carly:

She Leads Podcast

Twitter/X

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Join The Skip:

Skip Coach

Skip Community

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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 nikhyl@skip.community

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Timestamps

(00:00) Why most grads feel lost — and what to do about it

(01:44) How to navigate the 2025 job market

(03:29) Why hustle still wins (yes, even now)

(08:24) What to really look for in your first job

(15:03) Why seeking feedback is a career unlock

(17:30) Choose your boss — not the logo

(20:02) Why taking risks early pays off later

(28:35) How to tell a compelling career story

(32:15) Job hunting that actually works

(37:38) Making the leap from college to career

(42:18) Why you should work while studying

(46:13) How to maintain a network

(55:10) Green flags and red flags once you’re hired

(58:55) Your first job is a launchpad — not a life sentence

(63:12) Final advice we wish we heard at 21

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

The Mentor's Superpower: Pattern Recognition That Unlocks Careers May 19, 2025

Show notes

In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. Through 6 listener questions, we break down how mentors spot patterns others miss, and how you can use that insight to unlock your next move. Whether you're leading a team, switching paths, or just feeling off, this episode is packed with tactical advice for unlocking your career.

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Key topics

6 common patterns holding leaders back

How mentors can spot them, and what advice to give

Breaking through organizational barriers

Why smart people still get stuck

Navigating change vs. waiting it out

Thriving in early-stage chaos

Why strong reviews don’t always lead to promotion

Taking leadership roles before you feel ready

Finding—and becoming—a great mentor

How to ask better questions and get better advice

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Where to find Carly:

She Leads Podcast

Twitter/X

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Where to find Nikhyl:

Twitter/X

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Find The Skip:

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Timestamps

(00:00) How to spot patterns

(01:08) How to find and then become a mentor

(10:57) Scaling mentorship

(15:09) How to heat seek around patterns

(21:47) Question 1: How can I break through organizational barriers?

(22:29) Pattern 1: Are you actually stuck?

(30:05) Question 2: How can busy leaders stay technically up to date?

(30:28) Pattern 2: If you know what you should do, why aren’t you doing it?

(42:48) Question 3: How to navigate change?

(40:56) Pattern 3: Do you need to work on this problem, or just wait it out?

(52:23) Question 4: How normal is chaos in early stage companies?

(52:54) Pattern 4: Broken might be normal, and you were hired to solve problems

(61:07) Question 5: My performance reviews are excellent, but why am I not being promoted?

(61:41) Pattern 5: Are you growing faster than the company?

(67:35) Question 6: Should I take a leadership role that I don’t feel ready for?

(68:29) Pattern 6: Are you too humble or negative?

(73:23) Key takeaways and summary

(77:57) How to 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

Super Shadows | When Strengths Limit Growth Mar 26, 2025

Show notes

In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. We tackle a listener’s career dilemma: feeling stuck and unsure how to adapt to shifting expectations. Using a structured approach, we break down when to make a change, how to advocate for yourself, and how to evolve without losing what makes you successful. Whether you’re navigating subtle shifts or considering a big move, this episode helps you own your superpower—and the shadow that comes with it.

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Key topics

The unseen influence of Super Shadows
Why past success won’t fuel future growth
Breaking free from career stagnation
The power of self-advocacy
How top leaders seek feedback
Identifying what actually needs to change
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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Timestamps

(00:00) How your superpower can stall career growth

(01:11) Show format

(02:45) Listener question: Navigating a quiet career crisis

(06:40) How to break free from feeling stuck at work

(11:35) The case for self-advocacy in your career

(16:36) Why past success won’t fuel future growth

(19:48) Super Shadows: What they are and why they matter

(30:46) When it’s time to confront your shadow

(37:53) The risks of ignoring your shadow

(40:56) How great leaders seek feedback

(47:07) Pinpointing what actually needs to change

(55:57) A strategy for sustainable career growth

(57:04) Why change has to happen on the job

(58:19) A real-world example from Nikhyl’s offsite

(61:28) Key takeaways and final thoughts

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

Should you Stay or Go? A 5-factor framework for career-defining decisions Feb 27, 2025

Show notes

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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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

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

The Insider's Guide to Tech Compensation, Negotiation, and Career Growth Jan 30, 2025

Show notes

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:

Tech compensation: Beyond the offer letter

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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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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

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

The Widening Tech Career Divide: Big vs Small Tech Jan 10, 2025

Show notes

In this episode, I’m joined by Carly Malatskey, an engineer-turned-investor and podcast host of She Leads. We dive into one of the most important career questions in tech today: Should you work in big tech or small tech, or found your own company? With the rise of AI and new economic conditions, these choices have never been more different. We break down how industry dynamics have changed, the tradeoffs associated with each path, and some exercises for determining the best fit for you.

Key topics:

How AI is reshaping the tech job market
The (under-appreciated) differences between big tech and small tech
How PM and engineering roles have changed
How to assess your potential as a founder
What your worries reveal about your ideal work environment

Referenced:

Carly’s podcast: https://www.sheleadspod.com/
Ready to start a startup?: https://www.skip.show/ready-to-start-a-startup-shreyas-doshi-former-pm-leader-at-stripe-twitter-google/

Where to find Carly:

Where to find Nikhyl:

Where to 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) Teaser: Big tech vs small tech: Should you do both?

(00:35) Intro

(03:15) Why this discussion matters

(05:06) The biggest change in tech during 2024

(08:20) Why everyone should consider being a founder

(10:14) How to assess your potential as a founder

(14:44) How PM & engineering changed in 2024

(23:06) The all-important differences between big and small tech

(28:55) Assessing your fit for big vs small tech

(36:18) The challenges and benefits of working at both scales

(42:31) Do the best PMs work in big tech?

(52:17) Who this advice doesn't apply to

(54:56) Key takeaways

(56:33) 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) Nov 18, 2024

Show notes

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:

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

Live from Lenny's Summit | Career advice highlights Nov 01, 2024

Show notes

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

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Referenced:

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Where to find Nikhyl:

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Find The Skip:

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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

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

Mastering your 30 second resume Sep 20, 2024

Show notes

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:

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

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

Founder Mode, done right | Shreyas Doshi (ex-Stripe, Twitter, Google, Yahoo) Sep 10, 2024

Show notes

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: