An interview horror story, big podcasting milestone, and a few things I’m thinking about

Snowy Brooklyn, brutal candidate experiences, celebrating 100k downloads, PMs crying in bathrooms, Acquired, Sequoia, GSB, and two upcoming sessions.

We got a massive amount of snow in NYC last weekend, leading to daycare closure on Monday which gave us a curveball 3-day weekend. Our golden retriever George can’t get enough time in the snow, our daughter refuses to wear gloves and beanies while wanting to play in the snow but getting immediately cold, and my wife and I are just trying to get through the day while Ubers are 3x the price, buses are late, and snow piles render our stroller useless. Oh and it’s freezing for at least the next week so nothing will melt. Why do we live here again?

George in his happiest place

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🧟‍♂️ Interview horror story

I want to share what might be the worst candidate experience story I’ve heard in years.

I recently helped a PM prepare for interviews at an extremely hot company.

Over ~3 months, they invested 40+ hours into the process: take-home, panel presentation, multiple recruiter syncs, several follow ups with future teammates and executives, you name it.

They made it to the very final round and met the Chief Product Officer. Twice.

They were explicitly told that references would only be checked if the company was moving to an offer.

The company ran a reference check with a current teammate, who strongly vouched for them. Then... the company PASSED. No offer.

The feedback? “We all loved you but the CPO didn’t like you enough.”

This is hands down one of the most despicable candidate experiences I’ve seen. What a royal waste of time.

Running backchannel references against a candidate’s current teammates without consent is reckless. Doing it after telling the candidate the opposite is worse. Now the candidate’s team knows they’re exploring while there’s no offer in hand.

I’m tempted to name the company and publicly shame them but I won’t.

It would be irresponsible (and unethical) of me to broadcast the name of the company because anyone from the company who caught wind of the post would immediately know which candidate it’s about, and I don’t want that candidate to be impacted in any negative way from this... or at least more negatively than they’ve already been impacted.

But if you’re a hiring leader reading this, know that stories like this travel fast in non-public discourse, where your reputation is tested through backchannels. And stories like this will absolutely shape who will and won’t trust you with their career.

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And on a very different note…

🎉 My podcast just hit 100k downloads

Marc Baselga and I started the Supra Insider podcast almost two years ago with the goal of bringing product leadership conversations from within the Supra community to a wider audience.

This week we passed 100k downloads and it feels like a huge milestone. We've published an episode every week since March 2024. We only missed two weeks ever. Episode 100 airs in a few weeks.

We've made hundreds of updates to the podcast since its inception: branding, project management, guest outreach, editing, titles, pre-episode guest comms, etc. It all matters.

We've talked to many podcast growth experts and keep hearing the same thing: the key to growth is content quality and consistency. If we can do that for long enough, we'll grow.

Reaching 100k downloads feels like the perfect moment to reflect and try to unpack what's enabled us to be so consistent while improving the quality:

1. we have fun and don't take things too seriously - podcast recording slots are Marc and I's favorite items on the calendar every week

2. we only invite guests if at least one of us is extremely excited about them and prioritize the guests we're most excited about

3. we pick interesting "trailheads" for every episode and go off-roading by letting our curiosity pull us

4. we keep the lift for guests minimal; no pre-recording syncs, scripting, or prep work beyond trailhead selection (<2 hrs total time commitment including everything)

5. we trust that the more present we are in the conversation, the more engaging the episode will be for the audience

6. we aim for each episode to feel like a conversation between three friends who are learning from each other - the guest is an equal owner of the conversation

7. we don't delegate anything we don't do first ourselves - we have an incredible teammate named Tehreem who helps us run the podcast

8. we aim to make episodes that guests will genuinely want to promote and believe a world-class guest experience is a growth driver

9. we believe in making the podcast 1% better every week - the score takes care of itself

10. we treat the podcast as the energy source for everything else we do

Last but certainly not least: Marc. Marc is the key to our consistency. The guy is an operational savage. I admire his discipline and his ability to create systems that hold him (and now me) accountable to necessary behaviors and tasks.

The podcast is a well-oiled machine because of Marc's executional rigor. He makes me better every day.

Super grateful to all of our incredible guests over the last two years and all the people who bring us along for their commutes, gym sessions, laundry-folding and dish-washing and dog-walking, etc. We appreciate you.

It feels like we're just getting started. Here's to the next 100k downloads 🚀

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😵‍💫 Know thy culture

“DoorDash is the kind of place where PMs are expected to go cry in the bathroom and come back swinging.”

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🎙️ Supra Insider #94 featuring Casey Winters

This week we released episode 94 of the Supra Insider podcast, featuring one of my favorite product thinkers, Casey Winters (co-founder & CEO at SuperMe, previously Eventbrite, Pinterest, Grubhub).

We went deep on how Casey’s new company, SuperMe, is helping world-class operators open-source their expertise with their AI-native professional network. You can now chat with my SuperMe - it has access to ~350k “insights” ingested from almost everything I’ve ever said online.

I’ve followed Casey for nearly a decade so this was a bit of a dream come true moment for a product nerd like me. It was awesome. Big thanks to Adam Fishman for introducing us to Casey!

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🎥 How to get noticed by PM hiring managers in 2026

3,600 people signed up for a recent session I hosted with Hilary Gridley (WHOOP, Dropbox, Nike) and Nickey Skarstad (Duolingo, Airbnb, Etsy) about how to get noticed by PM hiring managers in 2026. Nearly 600 people showed up live! Full recording available for free here.

Some of the main topics we covered:

• Why the old playbook (generic resumes, cold outreach, etc) is breaking down as AI lowers the effort to meet the old quality bar

• What hiring managers actually respond to today: relevance, judgment, effort, and proof that you can do the job.

• How cold outreach still works, but only when it feels human, specific, and framed as an offer rather than an ask (bonus points if you can make them smile / laugh)

• Why building in public (writing, prototyping, experimenting) increases your surface area for luck and serendipity

• How referrals still matter, but only when they’re truly warm and easy to forward

• Why doing “too much” is rarely the problem - most candidates don’t do enough

Also - Hilary has been on fire with her Substack so be sure to check it out. She quickly took the session transcript and created 7 custom GPTs for job searching and shared them here:

I turned my hiring manager insights into tools

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🎙️ 10 Years of Acquired (with Michael Lewis)

I recently listened to the nearly 3 hour episode of the Acquired podcast (with Moneyball author Michael Lewis interviewing the co-hosts) and found it insanely relevant to the way Marc and I think about our podcast. For anyone thinking about building a media presence, this episode distills 10 years of learnings into 3 hours. It’s gold.

🎥 Don Valentine, Sequoia Capital: “Target Big Markets”

^ that episode led me to Acquired’s episode about Sequoia Capital, which led me to this incredible 1-hr Don Valentine (Sequoia founder) talk at Stanford in 2010 for anyone looking for a healthy dose of OG SV wisdom:

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🙋‍♂️ The stable marriage problem

This post breaks down why people who aren’t afraid to ask for what they want will get better results than the people who wait for opportunities to come to them 👇

The stable marriage problem

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⏭️ Coming up…

⚡️ How to interview product managers for AI fluency

Next week I’m hosting a free session with my friends Tal Raviv and Aman Khan: How to interview product managers for AI fluency. This will be the first time I share a new framework for interview design that I’ve been developing. Sign up here to join live and if you can’t make it to the session, you’ll get the recording afterwards.

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⚡️ What senior product people should know about fractional work

I also have an upcoming solo session sharing the most common advice I give people looking to get into fractional work: What senior product people should know about fractional work. It’ll be relevant to folks interested in the creator journey, audience building on the side, etc. Sign up here to join live and if you can’t make it to the session, you’ll get the recording afterwards.

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🫶 Want to support my work?

My goal is to always create way more value for the community through the free content I share than I capture through my paid offerings/services. If any of the below might be useful to you or someone you know, give it a look:

• 🎥 Self-paced course: Product Sense & Analytical Thinking Bootcamp for Meta-Style PM Interviews. I’ve now run four cohorts of the fully async version of the course and students are loving it because it fits their work schedules and interview timelines. Featured by Lenny Rachitsky 🔥. The $1,500 course price includes my Copilot below 👇

• 🤖 AI Practice Copilot for Meta-Style PM Interviews. My Copilot has helped dozens of PMs land roles at Meta, Google, OpenAI, Stripe, DoorDash, Uber, Datadog, Monday.com, and more. I’ve only ever had one refund request, with most people feeling like the value is well worth the $500 price (see testimonials on the site).

• 🧠 Product Sense Interview Template. Free Google sheet template for practicing product sense questions. Make a copy and get as many reps as you’d like with my frameworks. Updated regularly and fully compatible with my AI Copilot.

• 📊 Analytical Thinking Interview Template. Free Google sheet template for practicing analytical thinking questions. Make a copy and get as many reps as you’d like with my frameworks. Updated regularly and fully compatible with my AI Copilot.

• 🕵️‍♂️ Insider Loops. Company-specific PM interview guides for Stripe, DoorDash, Uber, and Figma (more coming soon). Rigorously researched and continuously updated by me and my friend Marc Baselga who you might recognize as my podcast co-host. We invest many hours into creating the guides and keeping them up to date based on real candidate debriefs. I would have gladly paid $300 for guides like this to get the “real talk” about what my top companies are looking for in the interview process.

• 🤝 Ben’s premium coach-matching service. White glove service in which I match PM candidates with calibrated interviewers from their target companies. Fully confidential and quick to start.

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Thanks for reading and see you next time!

2026 PM hiring predictions and the future of higher education

How PM hiring will change in the new year, the future of higher education, and the questions I’m asking myself as I celebrate my daughter's 3rd birthday this week

Hope everyone’s having a fantastic January so far. I’ve completed the first two weeks of my personal training package ( = 4 sessions) AND I’ve played pickup soccer two weeks in a row. The fitness journey is on track.

I learned that I need to be getting 1-1.5g of protein per lb of body weight. I started sharing my meals with ChatGPT and just this week realized how hard it is to get enough protein. Also realized I’ve been dramatically under-hydrating, which explains some of my historical issues with calf cramps during soccer. No cramps this past Tuesday night 💪

Upcoming free sessions

I’m getting into the swing of the new year and hosting a few live events in the coming weeks (RSVP for free below and get the recording even if you can’t join live):

⚡️ Thursday 1/22: How to get noticed by PM hiring managers in 2026

• The old playbook isn’t working anymore. Nobody is looking at cold applications. I recently met a product leader who hired a PM after receiving a thoughtful cold DM with a 1-pager strategy.

• In this session I’ll be joined by two fantastic product leaders and experienced hiring managers Nickey Skarstad (Director of Product @ Duolingo (previously @ Airbnb, Etsy) and Hilary Gridley (Product Leader (Whoop, Dropbox, Nike). Almost 2k people have already signed up.

⚡️ Tuesday 1/27: How to interview product managers for AI fluency

• Interviews are evolving in front of our eyes and many of the PM hiring managers I meet are scrambling to craft an evaluation rubric around AI competencies.

• I’ll be joined by two of my friends who are at the cutting edge of AI fluency, Tal Raviv (Riverside, AppsFlyer, Patreon), and Aman Khan (Arize AI | ex-Spotify, Apple, Cruise). We’ll dive deep into a framework for designing interviews to evaluate AI fluency in PM candidates (first time I’ll show this framework in public so I’m really excited).

⚡️ Thursday 2/5: What senior product people should know about fractional work

• More people than ever are reaching out to me and asking for my thoughts about fractional work: how to land customers, how to structure and price engagements, etc. There’s a lot of advice I’ve been repeating so my goal with this session is to package up the advice and link people to this recording.

• I did a try run of this talk in the Supra community and got tons of helpful feedback. This will get into solopreneurship, portfolio careers, etc. I pushed it out a week to prepare because there’s a lot I want to say.

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Interviewing at Uber, Figma, Stripe, or DoorDash?

If you’re a PM preparing for interviews at Uber, Figma, Stripe, and DoorDash, I think you’re going to love Insider Loops. This started as a passion project and it’s now a growing business I’m building with Marc. You can read about it in my LI post, Marc’s LI post or check out our site directly below 👇

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2026 PM hiring predictions

Over the last two years, I’ve been watching interview loops, hiring criteria, and candidate strategies change in major ways driven by AI, flattening orgs, rise of super ICs, etc. PM hiring is changing in front of our eyes.

I can’t stop infusing unnecessary ancient Egypt themes in Nano Banana sry

Here are my predictions for where PM hiring is headed in 2026.

1. Judgement and taste emerge as the top qualities evaluated in PM interviews. As AI handles more of the heavy lifting for producing artifacts and building products, PM interviews increasingly focus on what candidates choose to build and the depth of insight in how they critique existing products.

2. Experience evaluating AI system performance becomes a must-have for AI PM roles. Proven experience building golden evaluation sets and operationalizing AI eval loops becomes table stakes for PMs leading AI products, whether they train their own models or consume foundation model APIs.

3. PM hiring weighs domain experience higher than ever. As teams internalize the importance of AI evaluation, hiring managers favor candidates with deep domain intuition who can spot failure modes and make faster, better product decisions.

4. PM JDs are for senior PMs only.
   Companies will fill junior PM positions through internal transfers rather than open PM job postings. PMs with less than 3-5 years of experience will be under-qualified on paper for every JD.

5. The generalist PM hiring loop dies.
   Companies abandon “approve for hire first, match later” processes and only interview PMs for clearly defined roles with explicit mandates. Wrote a bit more about that here.

6. Cold applications die for real.
   As each JD gets hundreds/thousands of applications, hiring teams completely ignore inbound cold applications and shift to hiring fully through referrals, creative inbound that shows proof of work, and spearfishing outbound. On Jan 22nd I’m hosting a panel, How to get noticed by PM hiring managers in 2026, which will go deeper.

7. AI-native startups hire PMs after insisting they don’t need them.
   Companies that claim they do not need PMs will turn around their stance on this once they realize someone has to do the product management function. I wrote more about this here.

8. Big Tech PMs struggle to break into hot AI companies.
   PMs whose compensation is inflated by stock performance struggle to land attractive roles at hot AI companies because they’re overpriced and under-skilled (unless their experience in big tech is directly working on aI products).

9. Senior IC PM compensation hits all time highs.
   As the zeitgeist reinforces the story around PM leverage increasing (i.e. each PM doing the work of 3-5 PMs historically), hiring teams will raise the bar and compete aggressively for a smaller set of top talent, pushing the compensation ranges higher.

10. PM hiring evaluates AI fluency but it won’t be pretty.
    Interview loops increasingly differentiate between two buckets of experience: 1) building AI products and 2) using AI to build products. The second bucket will be easier to evaluate because it’s much easier to get that experience. Companies will struggle to evaluate the first bucket because many of them won’t have enough experience themselves, leading to lots of messy interviews.

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Happy birthday Gaia 🥳

This week was my daughter Gaia’s third birthday 🎂

She's at the age where real interests are emerging (the performing arts are definitely holding a special place) and we're starting to encourage sparks of passion and interest. K-12 is right around the corner and before we know it, university will be looming.

Will college still make sense for my three year old?

This week we published an podcast on my podcast with Stephen Cognetta (co-founder of Exponent) where we dove deep into the future of higher education and it's relationship with the job market.

This episode was a full-circle moment for me. Back in 2020, when I was preparing for my Facebook PM interviews, I spent an embarrassing number of hours watching Exponent's mock interviews on YouTube. I genuinely don’t think I'd land my FB offer without Stephen and Exponent.

Stephen sits at a really interesting intersection. He runs the leading interview prep platform for tech professionals, teaches at Northeastern, sells to universities, and does executive coaching.

He highlighted that these days many first year students come in with immediate goals around figuring out their plans to land a job when they graduate. But universities are not particularly good at job placement and they're getting even worse. So what are they good for?

For me, college was an incredible container for self-discovery and fun (time to explore, exposure to new ways of thinking, being surrounded by people who stretched how I saw the world, etc). I wouldn’t trade my time at the University of Florida for anything.

But I keep wondering about a different kind of student:

• Someone who isn’t especially interested in the “college experience”

• Someone who mostly wants a job

• Someone who’s pragmatic, motivated, and outcome-oriented

^ For that person, I’m less convinced the traditional university path delivers the value it promises.

If the goal is employment, the reality is that students need to develop real skills the market values and get good at telling that story in interviews / getting someone to bet on them. They don't need courses, degrees, and certificates. They need experience.

I'd love to see universities redesign themselves as experiential learning environments where students can get reps developing the skills employers value. But I think we have a long path ahead.

Will college be right for my daughter? I suppose it'll depend on her goals, options, priorities, etc. I'll encourage her to explore whichever environments seem to be the best fit. I'm sure we'll cross that bridge when we get there.

For now, I'm going to enjoy having a three year old whose biggest concern is not having enough Disney princess dresses. Happy birthday, Gaia ❤️

Feel free to check out the full conversation with Stephen:

• Spotify: https://bit.ly/4qrrwXi

• Apple: https://bit.ly/3NxzLlT

• YouTube: https://lnkd.in/eVR5ck84

• Substack: https://bit.ly/4qrrCy8

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Interested in getting matched with a PM interviewer at your target company?

I’ve been connecting PM candidates with calibrated interviewers at their target companies for coaching. It’s working well so I’m looking to grow the program.

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till next time ✌️

Ben

P.S. Part 3 of the PM career framework series on The Skip podcast dropped and it was excellent. If you’re thinking about making a change in 2026, I recommend the full 3-part series.

I'm hosting 3 sessions for product leaders in January

How product managers can get noticed by companies in 2026, how hiring managers can evaluate AI fluency in PM candidates, and what senior product people should know about fractional work.

As I was writing my 2025 reflection post I realized that almost everything I accomplished last year had a seed or spark in January. So I’m starting 2026 hosting three free sessions that cover current areas of interest to get the momentum going:

1. Jan 22: How to get noticed by PM hiring managers in 2026

2. Jan 27: How to interview product managers for AI fluency

3. Jan 29: What senior product people should know about fractional work

Here’s a bit more information about each and why I’m excited 👇

At the bottom of the post I’ll also share some recent content favorites.

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BTW… want to stop typing so much? My favorite voice-to-text dictation app is Willow. It’s faster and better formatted than any of the other Mac apps I’ve tried. You can sign up with my referral code BEREZ64 (auto-applied here).

To support my work, check out the links on my site at www.benerez.com.

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How to get noticed by PM hiring managers in 2026

Thursday, Jan 22, 2026 2pm Eastern

RSVP here - recording sent after even if you can’t join live

Hilary Gridley and Nickey Skarstad are two incredible product leaders who have been deeply involved in hiring at WHOOP and Duolingo over the last few years. They’re both extremely hands-on with AI, which has influenced how they think about hiring PMs moving forward. They also talk to a lot of other hiring managers at top companies, giving them a unique POV into the hiring side of the market.

The session aims to help the audience:

• Understand why old PM job search playbooks no longer work. Resumes, generic DMs, and surface-level signals fail in today’s market so see what hiring managers respond to instead.

• See what “real signal” looks like to hiring managers in 2026. How product leaders interpret proof of work, including building in public, shipping, and demonstrating strong judgment.

• Learn what actually cuts through the noise to get noticed. Examples of referral asks, cold outreach, and proactive work that earned attention, and why most attempts get ignored.

Why this topic matters

The PM hiring market in 2026 will be more competitive than ever. Candidates are sending more applications than ever and hearing nothing back, while hiring managers are flooded with resumes but still struggling to find the right signal. This session breaks down how the hiring bar has quietly shifted and what actually helps PMs stand out today, long before the onsite interview.

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How to interview product managers for AI fluency

Tuesday, Jan 27, 2026 1pm Eastern

RSVP here - recording sent after even if you can’t join live

I hosted a session a couple months ago with my friends Tal Raviv and Aman Khan (Unpacking Meta’s new “Product Sense with AI” interview) and we had a blast doing it. We’re all getting our hands dirty with AI and developing our intuition around how the craft of PM is evolving given these new capabilities, and we believe PM interviews are due for a major refresh to account for the changing expectations.

The session aims to help the audience:

• Define your evaluation rubric. Differentiate between building products with AI and building AI products (and why each requires different evaluation).

• Structure your PM interview loop. Map the most critical AI fluency dimensions in the rubric to behavioral, case, and take-home interviews.

• Reduce false positives in interviews. Identify common failure modes in PM interviews and redesign or remove evaluations that don’t produce useful signals.

Why this topic matters

Every company will want to hire AI-native PMs in 2026. But most PM hiring managers have never been through interviews that gauge their experience building products with AI or building AI products, thus don’t have a clear mental model for evaluating these areas. Instead of running the old interview playbook, this session will help you design PM interviews for the AI era.

The three of us jamming about the future of PM interviews in Brooklyn last summer

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What senior product people should know about fractional work

Thursday, Jan 29, 2026 2pm Eastern

RSVP here - recording sent after even if you can’t join live

My last full time role was as the head of product at Continuum, a Series A startup building a marketplace for fractional executives. While we weren’t able to crack the demand side of the marketplace in a venture-backed scale, we had insane PMF on the supply (talent) side of the marketplace.

This gave me essentially unlimited access to world-class senior talent doing fractional work either instead of, or in addition to, their full time job. I spoke 1:1 with dozens of fractional leaders about what’s working and not working, which felt like hard-earned secret knowledge.

I’ve kept those conversations in mind as a solopreneur over the last two years, while allowing my own experiences to shape my views about fractional work. I’ve been finding myself repeating a lot of the same advice to people reaching out to me so figured it’s time to share more widely.

The session aims to help the audience:

• Design fractional work around your life. Learn how to start with your time, energy, and income needs, then design fractional work that fits them.

• Position yourself narrowly without boxing yourself in. Learn why specificity drives referrals and how to pick one clear positioning that still leaves room to evolve.

• Build a sustainable fractional portfolio. Learn how to combine advisory, part-time, and interim work to avoid income volatility and burnout.

Why this topic matters

Full-time work no longer offers the stability it once did. Layoffs and reorganizations have made even strong roles feel fragile. Fractional work offers a new way to build security through multiple clients and income streams. This lesson shares practical frameworks for designing fractional work intentionally, so it creates resilience and control instead of stress.

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Content Recommendations

Supra Insider

I co-host the Supra Insider podcast and want to share a couple of our top episodes from 2025:

• #80: Becoming an IC again is how products leaders will stay relevant in the AI era | Gokul Rajaram (Investor and Company Helper; ex-Google, ex-Facebook)

• #89: The hidden role of rituals in Duolingo’s product culture | Nickey Skarstad (Director of Product @ Duolingo, ex-Airbnb, Etsy)

The Skip series on PM career frameworks for AI

I love Nikhyl Singhal‘s breakdown of how product leaders should be thinking about their career in the age of AI. I listened to both Part 1 and part 2 over the holiday break and am excited for part 3 coming soon.

Live in NYC

We took Gaia to see Mozart’s Magic Flute at the Met Opera over the break, which was my first time at the opera. I learned that it’s a Singspiel, a popular opera form that included both singing and spoken dialogue. So good.

Carole and I took advantage of her mom visiting us and also snuck out to the Broadway run of Oedipus, starring Mark Strong and Lesley Manville. We all knew where it was going but the acting was superb so we were invested. It was superb.

TV

I’m a big fan of Better Call Saul so when I saw Vince Gilligan teaming up with Rhea Seehorn for a sci fi Apple TV, I couldn’t wait. Pluribus delivered. It’s slow but so good.

I’m almost done with the last season of Stranger Things and am really enjoying it.

Film

Carole and I saw Marty Supreme in the theater over the holidays and it was fantastic. Same director as Uncut Gems so if you want to feel tight for 2 hours, this is for you.

We also watched Frozen 2 with Gaia over the break which is surprisingly dark. We liked it.

Books

Currently reading book 5 of the Malazan series, Midnight Tides. When I want to switch it up a bit, I’m also reading Ikigai.

I recently got Marc Baselga into both Project Hail Mary (which he loved) and Hyperion if you’re looking for sci fi recs.

Music in the background while working

Found a YouTube channel I love with live daytime sets for deep house, which is extremely enjoyable to have in the background while working.

My 2025 lookback and 2026 lookahead

Reflecting on my 2025 highlights across personal and career, and looking ahead to 2026.

Hey everyone, hope you’re enjoying the holiday break! I started this Substack six years ago, which makes it as old as a first grader. Can you tell I’m seeing the world through the lens of a dad almost everywhere I look now?

I started this newsletter to replace an annual-ish life update I used to send to friends, family and people who helped me along the way. This was never meant to be my main platform for sharing thoughts about product, work, etc. I saw it more as a public journal of sorts.

As I look back at my activity here in 2025 (or lack thereof), it’s clear I completely neglected this part of my life. I only published one post all year. I did spend a lot of time on Substack this year, but for a different publication: Supra Insider (the podcast I co-host with my good friend Marc Baselga).

Instead, my writing took place mainly in DMs, group chats, on LinkedIn and in emails to my Maven list.

I would like to get back into writing here in 2026. Let’s see how it goes.

Wishing you all a happy new year 🥳

Ben

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Want to get my next post in your inbox?

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Writing this post gave me an excuse to look back at what I did this year and man… it’s a lot!

This post is written for future Ben to look back and appreciate this moment. When you’re going fast, things blur and I don’t want my life to be blurry.

It’s not a comprehensive reflection on everything that happened in 2025 or a detailed roadmap for what’s coming up in 2026. But I’ll touch on both, and I’ll do so bucket by bucket:

1. Family & Personal Life

2. Maven Course

3. AI Copilot

4. Supra Insider Podcast

5. Insider Loops

6. Content

7. Coaching, Advising and Consulting

8. Side Projects / Community

9. Income

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1. Family & Personal Life

2025 Lookback

My proudest achievement is that I spent 2-3 hours a day with my daughter Gaia and my wife Carole while achieving all of my professional goals. Most weekends were entirely offline with family. This is my core, and I’ve gotten better at defending it.

I also carved out dedicated time for non-work stuff that matters to me:

• Carole, Gaia and I spent a week in Belize, a week in Costa Rica, and a full month in France.

• I took my dog George for three separate full-day Friday hiking trips in Hariman State Park outside of NYC. Excellent thinking time while getting him exercise.

• I played pickup 7x7 soccer twenty times.

• I hosted my sister and her kids in NYC. I hosted my mom too.

• I traveled to Florida twice to visit my mom and grandma.

• I flew out to SF for the first time since we left ~4 years ago and made it to Tahoe for my friend Laser’s bachelor party. I crashed for a couple nights with my friend Connor.

• I got closer with more dads in my neighborhood as the line between socializing and family time continues to get murky (which is hard to appreciate without kids).

• I read a few pages of a physical book almost every night before bed. Lots of epic fantasy (I’m now on book 4 of the Malazan series after taking a detour to the latest Stormlight Archive book).

• I started using a monthly blood collection service to track my health on a tighter basis and am more informed (while I’m not optimal everywhere, as of this month nothing is in the red).

• I rarely have a hard time falling asleep and get 7+ hours of sleep most nights.

There’s more but I’ll leave it at that for now. The personal highlights come first because they’re the foundation for everything else. Without a healthy personal life, none of the rest matters. I love my girls and George 😍

Going into 2026…

I’m going to continue prioritizing family above all else and continuing to be extremely active as a dad and carrying my weight at home. We will continue to travel, especially when we need a break from the cold and/or heat in NYC. A month in Europe in the summer will ideally continue to be a thing we do.

One area where I fell short in 2025 is my personal fitness. I just bought a 24-pack of 1:1 sessions with a personal trainer here in Brooklyn and I’ll go Mondays and Wednesdays at 10am for the first three months of the year, with a plan to transition to 4-person group sessions afterwards. My main goals are to gain functional strength, trim the waist line, and feel better / more energized.

I’d love to play pickup soccer at least once every month, but ideally closer to 2-3 times. Taking 10 days this year to hike outside the city with George feels like a good goal too.

I’ll keep reading paper books every night before bed, probably getting through 3-4 more Malazan books because they’re thick (but so good).

Two of my best friends (Laser and Sam) are getting married next year, so I’m excited for those two weddings. Laser is the one who got me tangled up in the Malazan series. And yes, his real name is Laser.

It’s not clear yet whether I’ll be able to make it to Israel to visit my dad and family this year but I’ll do my best to make that happen.

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2. Maven Course

2025 Lookback

I ran eight live cohorts of my Maven course this year, serving almost 200 students.

After running the tenth and final live cohort in October, I decided to overhaul the course to better fit the schedule of busy PMs getting ready for interviews. I received emails all summer from people who wanted to take the course while I was in France but the next cohort didn’t line up with their interview schedule and availability.

So I decided to take my own availability out of the equation and re-launched the course in a fully self-paced format.

My first self-paced cohort ran in December and it worked great for students and for me. I’m getting less students than I used to but students can now access the full course content on their own schedule which feels like a big win. Once they complete the syllabus, they get access to my AI Copilot for practice. In addition to benefitting students, this also allows me to re-allocate the time I used to spend teaching live cohorts into other priorities I’m excited about (more on that below).

My Maven mailing list grew to over 13,000 emails this year, fueled by eight live Lightning Lessons, which are free workshops that funnel signups into my course waitlist. The sessions had 2,800 live attendees which is a full small-scale sports arena. You can see all my lightning lessons from this year here.

My biggest lightning lesson of the year, How top companies evaluate PM candidates in 2025, has 7.8k signups. I believe it’s a top 5 LL all-time on Maven. People loved what the panelists - Nickey Skarstad , Chantal Cox and Stephanie J Neill had to say.

Another big win I’m celebrating is the inclusion of my course in Lenny’s List, a hand-selected lists of Maven courses curated by Lenny Rachitsky. This has helped me with both discoverability and credibility.

Thanks to both Lenny and Maven for helping me grow my course this year 🙏

Going into 2026…

I’m planning to continue offering the self-paced version of the course and running frequent cohorts. Since there are no longer any live sessions, this is easy. I want to ensure PMs can always get the course on a tight interview timeline.

I’m planning on doing more Lightning Lessons in 2026 than I did in 2025, because it’s been such an effective way for me to share content with my audience that is valuable, and also help me grow my list. Maven has crafted a genuinely effective win-win platform with these Lightning Lessons and I’m excited to keep investing. The other cool thing about the Lightning Lessons is that I can also take the recordings and publish them on my YouTube channel (more on that below).

I’ve contemplated launching an entirely new course on Maven, but I’m holding off on that for now. It’s exciting but likely a distraction. It doesn’t feel like a primary goal, but maybe something that will come up organically this year if the timing is right, and I get really excited about a new topic.

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3. AI Copilot

2025 Lookback

My AI Copilot was my least expected win of the year. I’m happy I leaned into it and found ways to make it better while also getting a feel for how to market it.

A few months ago I published an episode with Marc on our podcast sharing the whole story around my AI Copilot and we covered all the bases so I won’t repeat them here but if you’re interested, just check out the episode:

With zero paid advertising, I sold over 200 units with only one refund request. I get regular emails from people telling me it’s the best $500 they’ve spent given the comp packages they’re targeting are often $500k/year or more.

I wanted to showcase more of these testimonials so I vibe-coded a website for the Copilot that has allowed me to tell the story in a way I’m proud of. The website has real demos, videos, FAQs, and more.

Building the website also gave me an excuse to spend a lot of time in Cursor and staying on top of the latest capabilities with AI prototyping tools powered by LLMs. I use Stripe, Zapier, and Apps Script to automate delivery. It felt really good to get my hands dirty and take control of the full stack.

Going into 2026…

I’m keeping a very close tab on how interviews are evolving (especially the interviews that I cover in my course and with the copilot). I’ll need to keep the Copilot relevant otherwise it’ll become obsolete. I imagine it’ll be good for another 3-6 months before another major update will be needed.

As for the website goes, I think it’s in good shape. I plan to publish more content in 2026 to market the copilot and show it in action because I continue to get feedback that people want to try it before they buy it but that’s fundamentally hard because once you have it, you have it (it’s a one-time purchase).

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4. Supra Insider Podcast

2025 Lookback

My co-host Marc Baselga and I published over fifty episodes of the Supra Insider podcast this year. We published every single week. The show drove 64k downloads and 120k Substack views across 85k people. Our YouTube hit 1k subscribers (up 5x from last year) with 116k views and over 3k hours of watch time.

Our Spotify follower count grew 3.5x to 750 followers. Spotify delivered 10k plays and 2k consumption hours. Our total Spotify audience was 2.2k people. We have over 3k Substack subscribers.

Based on our most recent Spotify Wrapped, we’re the top podcast for 71 people. Those are our true fans.

Zooming out, the real value of the podcast isn’t in the numbers. It’s the conversations and the ritual.

The podcast helps me stay close to what’s shifting in how products get built and how work gets done in the age of AI. Everything I do requires me to be extremely plugged in and the podcast is an excellent forcing function for it.

The podcast has also allowed me to maintain a consistent habit where I talk with other people about topics that are interesting to me and publish something. Shipping on a regular cadence has been amazing for regulating my mood.

Going into 2026…

We’re going to keep publishing at least one episode per week, experimenting as we go with ways to make the podcast more fun for us and improving the guest experience. As long as we’re learning, having fun, and talking to interesting people, this podcast has staying power.

We’ll likely experiment with monetization this year, exploring partners/sponsors who want to reach out premium audience. I truly think we have one of the best podcasts for product leaders in the world. The key to growth will be consistency and quality above all else. The score will take care of itself.

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5. Insider Loops

2025 Lookback

I launched Insider Loops with Marc (same one I co-host my podcast with) in September to help PMs prepare for interviews with Uber, Figma, Stripe. We added DoorDash in October and are working on the next guide now at a very hot company almost every PM wants to join.

We have many happy customers and proved the core thesis with very limited distribution. We’ve validated that PMs will pay for company-specific interview prep if they trust the source of the insights and know they can’t find this content anywhere else. We’ve developed a strong sense for how to create and market our guides, but still haven’t cracked large-scale distribution.

Marc and I have a full-blown collaboration in a shared repo that we each contribute to in Cursor (for the vibe-coded site as well as guide creation, updates, changelogs, etc). This project is another accelerant for Marc and I to stay very on top of AI tools (just this week Marc told me how Claude Skills are helping with some aspect of our guide changelogs). Insider Loops also gave me a reason to play with Gamma and we love it for this use case.

Marc and I dedicated a full podcast episode to talking about the full story behind Insider Loops if you’re interested in learning more:

Going into 2026…

We’re receiving real-time feedback from our customers about their interview experience and incorporating these insights into the guides on a biweekly basis. When someone buys one of our guides, they’re getting lifetime updates to that guide for a one-time payment.

The process for updating the guides is getting better every week and we’re well-positioned to become the best destination for updated PM interview guidance at top companies. Today that’s Stripe, DoorDash, Uber and Figma. But we’re planning to create many new guides for popular companies hiring PMs in the new year.

In addition to improving current guides and adding new guides, the third piece we will be looking to crack in 2026 is scaling relevant traffic to our site. This will be an ongoing area of experimentation for us.

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6. Content

2025 Lookback

My content footprint expanded quite a bit this year, even outside of the podcast and my Maven course and lightning lessons.

The highlight was definitely publishing not one but two guest posts on Lenny’s Newsletter in April and July, respectively:

• The definitive guide to mastering product sense interviews

• The definitive guide to mastering analytical thinking interviews

Those two posts now dominate SEO for “Product Sense interview” and “Analytical Thinking interview.” Given that these are the two most common interviews PMs encounter, I’m very happy about this result. The Lenny posts drive consistent traffic to my interview templates (PS | AT) and course page. Writing a Lenny post is a big lift because of his insanely high bar and it’s worth every minute.

My LinkedIn follower count grew this year from 8k to 21k. My posts drove 2.5 million impressions and 32k engagements, reaching 570k members.

I also decided to start a YouTube channel early this year and have been working with an incredible video editor in the Ukraine who I found on Upwork. My channel went from literally 0 subcribers to over 900, driving over 100k views with 3.3k hours watched.

I also made two appearances on podcasts I’ve been a big fan of as a listener for years:

• Adam Fishman’s Startup Dad

• Peter Yang’s Behind the Craft podcast

Going into 2026…

Content is everything in this phase of my career. Staying top of mind for my network is key to manufacturing serendipity and increasing my surface area of luck.

In addition to podcast-related content, I will continue writing regularly on LinkedIn, ideally writing more here on Substack, and doing a lot more on YouTube. I want to keep sharing my ideas and growing my platform for amplifying strong thinkers I admire. If I get invited on a podcast I like, I’ll say yes.

I’m going to create way more value for people than I capture in any of the products and services I sell. High quality, premium content, and a lot of it. That’s the goal.

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7. Coaching, Advising and Consulting

2025 Lookback

I coached <100 PMs one-on-one this year with dozens of those as paid sessions (many were my students). Many landed new roles and credited our time together with their success.

There have been times when I wasn’t available for coaching so I built a very small network of top-tier interview coaches for Meta, Google, Stripe and DoorDash. I’ve learned that many PMs trust me over platforms for coach-matching, even if the folks I refer them to are more expensive. Folks looking to get matched with a coach through me can submit this Google Form.

While building my solopreneur/creator revenue this year, I also kept some fractional product work going:

• I did six months of part-time PM work with a Series A fintech startup called Lettuce which was fun and kept me fresh shipping product. The company is building for solopreneurs and most of the team is fractional so it’s just a great fit. And Ran Harpaz, the founder/CEO is an awesome human being who I’ve enjoyed helping.

• I completed a two-month paid customer research project for a stealth AI company early in the year, which I always enjoy.

• I’ve also had a paid advisory engagement going for the past six months with a talented early career head of product.

I liked the fractional work and it generated meaningful income but I had a realization halfway through the year that fractional product work doesn’t accelerate my solopreneur flywheel as much as the podcast, course, and copilot. In a way, Insider Loops came out of my need to replace the fractional PM income.

Going into 2026…

I’m not looking for consulting projects or part-time PM work but I’d love to have another 1-2 advisory engagements going with early career heads of product at growing companies. Basically, extremely sharp people with a strong work ethic and no PM background who find themselves running the product function at their company.

Looks like my experience as the first PM at three startups paired with my experience as a coach come together to make me a pretty effective advisor to this kind of client.

I’ll keep my 1:1 interview coaching in the new year but I will likely increase my prices again since control over my time is becoming more important to me. I will keep vetting coaches to refer folks to if I’m short on bandwidth and also for more affordable rates. If you want 1:1 coaching with me, you can grab time here.

8. Side Projects / Community

2025 Lookback

I got to a working MVP for a new product called Airframe with my friend Connor Jacobsen. I ran customer research with about fifteen PMs and learned a lot about how people are using Projects in Claude and ChatGPT. We ultimately decided not to move forward with it because the problems we wanted to solve were getting shipped faster than we expected by OpenAI and Anthropic, which is amazing. I don’t believe in building solutions if someone else is solving the problems I care about better and faster than I could.

On the community side, I’ve been investing time into two main forums.

Supra: I’ve been a member of Marc’s Supra community for over two years as the community has grown to over 400 members now. In the fall, I founded a self-facilitated Supra cohort for Maven instructors including Tal Raviv, Aman Khan, Colin Matthews, and Hilary Gridley. I organize and facilitate our 90-minute sessions every 5-6 weeks. We learn a ton from each other and some exciting collaborations have already come out of it. Excited to keep it going in the new year.

PM Creators Country Club: I become friends with Peter Yang this year after going on his podcast and we decided to bring together some of our favorite people in our DMs into a WhatsApp group that we jokingly named the PM creators country club. This group includes Peter, Tal, Aman, Colin and Hilary above and also Adam Fishman, Nickey Skarstad, Chantal Cox, Elena Verna, Marc Baselga, Sachin Rekhi. Conversations in that group have replaced a good amount of social media time for me and I love it.

Going into 2026…

Side projects are unpredictable so we’ll see what piques my interest! But the community stuff will definitely continue.

9. Income

2025 Lookback

I’m transparent in a lot of ways but numbers are still a little uncomfortable for me to share publicly. That said, 2025 was the best income year in my career.

What I’m most proud of is that I got there with a real diversification of income streams, with the biggest contributors being:

• 35% from Maven

• 25% from AI Copilot

• 25% from fractional product work

Going into 2026…

Given that most of my revenue this year came from unexpected places, I’m not going to share public goals for revenue. I’m focused on maximizing number of hours spent doing work that plays to my superpowers and that I find engaging and meaningful. I want a lot of time in flow. As long as I continue creating a ton of value for people and capturing a fraction of that in the form of monetization, 2026 could be an even bigger year for me. Let’s see how it goes.

I went on a podcast for dads

On portfolio careers, parenting, and accidentally building a dad community in Brooklyn

It's been a while since I've written here (November... oops). A lot has happened, but honestly, most of it has been the slow, steady evolution of learning how to be a parent while building a career that doesn't look like anything I expected a few years ago.

I recently had the chance to sit down with Adam Fishman on his Startup Dad podcast, and it was the first time I've really talked publicly about how becoming a dad has changed... well, everything. Most of my content these days is about product management and interview prep, so it felt both vulnerable and important to dig into the backdrop that actually drives how I show up in my work: fatherhood.

YouTube:

Spotify:

A few things that surprised me as I was talking through it:

The portfolio thing is working better than I thought. When I first went fractional/solopreneur, Carole & I worried about financial stability. Turns out, having multiple income streams (fractional PM work, my Maven course and AI copilot for interview practice, the podcast I co-host) actually feels safer than when I had one employer who could decide my fate. No single client represents more than 30-50% of my income these days.

Solo parenting days are sometimes easier. This one caught me off guard. When Carole travels for work and I'm flying solo with Gaia, there's zero communication overhead. If something doesn't get done, I know exactly where the ball was dropped. The control freak in me finds it oddly relaxing compared to the constant "did you pack the snacks?" coordination of tag-teaming.

I've accidentally built a dad community. Walking around Brooklyn with Gaia has connected me with other dads in ways I never expected. I’m part of a group called "Dadmilk" (😂) with about 15-20 neighborhood dads, and it's become one of my most valued social circles.

The structure thing is real. Before kids, routines felt limiting. Now they're the only way I get anything meaningful done. Our bedtime routine has been the same since Gaia was 3 months old, and it still works like magic. Carole deserves all the credit for figuring this out—I was just following her lead in those early days.

Gaia's almost 2.5 now and turning into this little person with opinions and jokes who gets her gentle, playful energy from Carole and has trained George to be her personal floor-cleanup service.

The conversation with Adam made me realize how much Carole and I have been figuring out as we go, and how rare it is for me to actually pause and reflect on what's working and what isn't. If you're curious to listen/watch the full convo, it's on Spotify, Apple, and YouTube.

My happy place is with Gaia… hers is with a cookie

Carole really is the best mom 😍

What's been going on with all of you? I know I've been terrible at staying in touch, but I'd love to hear what you've been up to.

Ben

P.S. - Still haven't finished a single parenting book. Somehow we're all still alive.