COACH V1: PRODUCT EDITOR tl;dr Coach v0 was the reviewer. Coach v1 is the editor. Excited to share Coach v1: a Product Editor with taste and judgment. Coach started as an opinionated reviewer for product docs. You pasted in a PRD, strategy doc, roadmap, OKR doc, or one-pager. Coach read it like a senior product leader and gave you a structured review. That first version was useful. It also brought clarity around what the next version should be. People wanted the review to persist. They wanted Coach to remember the doc, remember prior feedback, react to edits, and keep working with them. A one-time review was too static for the way real product work happens. So I rebuilt Coach around the document itself. You now write your Product Spec inside Coach. Each section gets reviewed as you work. There are four core sections - Problem, Hypothesis, Success Metrics, Rollout - and optional sections that you can add. The other change I've made is to start with a crisp mini-PRD as the default template. massive PRDs of Most product specs are now mini-PRDs. Under the hood, Coach also now exposes MCP, so agents can create, read, edit, review, and export Product Specs through the same private Coach judgment system. The product-feedback skill stays confidential. Agents get document operations, not the underlying rubric. That matters because Coach is no longer just a place to get a review. My goal is to make it the place you go to create the highest quality specs on the planet. This is the right foundation for a lot of new things I want to build. I have a lot of plans for Coach! Companies have refounding moments. Products do too. And this is one for Coach.

lol

A successful Silicon Valley entrepreneurs told me today that he had no health issues of any kind when he was in the supposedly high stress job of running a fast-growing tech company. Once he sold his company (for mid 9 figures USD) and stepped away from a full time operational role, his blood pressure and cholesterol spiked. He believes that sitting around and worrying about random things has been more stressful for him than a full-time operating role. He is now planning to get back to starting or running a technology company. My takeaway: you feel happier and less stressed doing something you enjoy than doing nothing at all.

Founders: One of the best startup hacks I've seen is hiring a smart generalist to own the numerous random yet critical projects that need an owner. From sourcing talent to creating customer decks to sending investor updates, they can be a massive accelerant to your business.

How to present In 2006, I helped @ericschmidt create a deck outlining Google’s strategy, for a presentation Eric was delivering to the company. It taught me a profound lesson on how to present. When I showed up to my first meeting with Eric, he asked me to visit with every product team at Google, chat with them to figure out what they were working on, and then summarize it on one slide (for each team). Easy enough, I thought. I would use 3-5 bullet points per slide. Piece of cake. I started mentally mapping things out and got ready to leave. “But”, Eric said, “I want no words on any slide”. My well-laid plans disintegrated in an instant. How was I supposed to convey the key messages from each team, without WORDS? Eric must have seen the panic on my face, and kindly gave me a hint. “Put the text in speaker notes”. “But what goes on the slides, Eric?” I continued panicking. That classic, gentle “Eric smile” fluttered on his face. “Why, images, of course!” “You mean, you want each slide to just be comprised of images?” “You got it. And use the title wisely. 7-8 words max. Let’s meet in a week to review progress.” As I left the meeting, little was I to know that this conversation would fundamentally change my view on how to deliver effective presentations. 17 years later, I still cling tightly to the following principles: 1. The larger the audience, the fewer the words on the slide. In Eric’s case, the audience was thousands of employees, so we had 0 words per slide. 2. The title does most of the heavy lifting, which means it cannot be passive. It must be action oriented. Eg: not “Subscriber retention” but “Subscribers continue to be retained strongly” or even better “Net revenue retention continues to be > 100%”. 3. Use memorable images that substantiate and give credence to the words of the title. This image is what will occupy most of the slide area, so you need to spend much of your time thinking about what picture will best get the point (made by the title) across. In some cases, it might be a customer image or logo. in other cases, a graph. In yet other cases, it could be something else entirely. For the Google presentation, one of the images that gave me the most trouble was a slide on Google Search Appliance and other Enterprise products. The title stated that these products were increasingly being used by larger customers. The team didn’t want to share customer logos broadly since some were confidential, so logos were not an option. I decided to go with a trend line on the % of searches from enterprise customers, but the person who was supposed to pull this data for me, flaked at the last minute and I had to scramble. I ended up scrambling to create a mosaic of a bunch of consumer product logos with some kind of icon that denoted large enterprises. Not my finest moment but it got the point across. 4. Use speaker notes. Like Eric said, speaker notes should contain most of the details. It puts a lot of burden on the speaker since they cannot just read off the slides. But this doesn’t deter good speakers, since they prepare dozens of times, and then again. So there you have it: my 4 principles for delivering compelling presentations to live audiences. (CAVEAT: If the presentation has to be emailed to an audience who will consume it asynchronously, that’s completely different and has different rules). How did the 2006 Google strategy presentation turn out, you ask? It went quite well, and later I got a nice thank you note from Eric. I didn’t realize at the time that I should have been the one thanking him for the once-in-a-lifetime learning opportunity.

Friend: “I know this guy who gets driven from Atherton to SF every day.” Me: “That’s not uncommon.” Friend: “He gets driven in a van, and the back of the van is set up with a @onepeloton and a TV, so he gets his workout in on his drive to SF. How common is that?” Me: ..

0. Startup CEOs: if you want to hire the leader for a particular function, follow this playbook.

Many founders who raised large amounts of money ($10m+) in 2020-21 but subsequently realized they don’t have PMF, are going through an excruciating psychological journey right now. On one hand, they feel beholden to employees and investors to keep building, pivoting, doing anything to live up to their perceived commitment to their stakeholders to build an enduring company. On the other hand, they have a sinking feeling that they are just rearranging deck chairs on the Titanic. Their heart just is not in it. There is a deep-felt malaise. The more money a founder has raised, the deeper this predicament. I just had the first such founder return a good chunk of invested capital back to investors, because they couldn’t take the pressure any longer. The relief they felt when they realized investors and employees were on board and 100% supportive of their decision, was palpable. (All employees received solid severance before the company shut down). Founders - ultimately it’s your call, but know that there is a graceful way out. Chasing endless pivots trying to find PMF is a bridge to nowhere. Investors - let’s have the grace and courage to tell founders this option is available to them. The founder told me that the reason they ultimately decided to return the money stemmed from a convo with me several weeks ago, when they told me about their latest pivot, and I told them I’m supportive “as long as their heart is truly in it”. That phrase stuck with them, they introspected and ultimately realized their heart was not in it.

0. CEOs, CPOs and VPEs: The core product team has traditionally been a triad: Engineer, Designer, PM. Consider changing this to a quartet by adding Analyst. Product analysts can transform product development. Some ways in which they do this:

SF on Saturday morning: a large % of Waymos are ferrying solo kids (8-14 yo), presumably to sports or other activities. A friend told me that 85% of parents at their kids’ SF school use Waymo for kids pickup / drop off: earlier it was ~10% using Uber and Lyft. Shows how Waymo has grown by expanding the market, serving segments who otherwise were non-consumers of ride sharing. Though it’s expensive to build companies serving non-consumption markets, some of the best and greatest companies (SpaceX, AirBnB, etc) have and will be built creating new habits and markets.

$1m ARR co. Tried to raise bridge round at $30m cap. Little interest. Changed “bridge” to “pre Series A”, raised cap to $60m, waited a month to ensure metrics still strong, went to raise again. Oversubscribed 2x. Never underestimate the importance of narrative and confidence.

1. I have been trying to find the best "first question" to ask a startup when I meet with them. After many iterations, I think I have it. Here it is, and here's why it works.

Hearing from CPO candidates in the market: many Series B/C companies haven’t yet found PMF despite having raised tens of millions of $. The CEO believes the CPO will help them find PMF. Finding PMF for a company is a a cofounder role (with appropriate equity), not a CPO role!

DON’T BE JUMPY Got this message from a CEO about a candidate: “I don't think they'd be a good fit. We have a pretty hard rule on no jumpy folks and their background looks like a alot of 1.5 years and then gone”. Current and future job seekers: don’t be jumpy. Accomplish something meaningful at each company before considering a new role. Making an impact (and ideally showing increased scope over time at the company) takes 3-5 years, not 1-2 years. Jumpiness at multiple companies is viewed negatively by recruiters and founders alike. It shows an inability to stick around and see things through.

Thinking Machines is the fastest growing company in history. No comparison. They've hit $80M ARR in 1 day. Take that, Mercor, Cursor and other contenders!!!!

The “what’s your moat?” question for early stage companies ignores the fact that if a one year old company can build a moat, it’s NOT a real or deep moat. Real defensibility take significant time to build. Correct phrasing; “What will be your moat?”

Just spoke with a founder who's shutting down their company. Over the last few years, the company built a handful of products that people oohed and ahhed over (and professed love for, when asked for feedback), but very few people actually used daily or were willing to pay for. Founders: the difference between a "nice-to-have" and a "must-have" product is so tiny that if you don't realize or own it, you might end up spending years of your life building something that doesn't have the impact on the world you aim for. You owe it to your stakeholders (and to yourself) to be honest with yourself.

Why do some founders raise at 500m with 0 revenue while others struggle to raise with 10m revenue? Fundraising is about NARRATIVE, not just NUMBERS. Narrative includes a compelling Why Now, a tremendous Team, a differentiated Product and Strategy, and a massive Vision.

Seeing a small number of founders start to move away from pitch decks and instead use long form memos to describe their product / biz. These docs show clarity of thought and allow for better discussion.Decks aren’t going away anytime soon,but I for one am a fan of this trend.

Top venture investor: "We are cutting all valuations by 50%. And a flat round is the new 3x up." This is what most startups have to look forward to over the next few quarters. Brace yourself.

Just heard of a law firm that fired their legal AI vendor after they missed a court date for a $100m case. In several verticals like law, health, etc, accuracy of the AI tool is non negotiable - it can be a matter of life and death or have massive financial implications.

Rule of 30: startups often give up on fundraising too early. You need to meet at least thirty investors before you can conclude that your fundraising is not successful. Remember, you only need ONE investor to believe in you. If you hear the same msg from 30 investors, reassess.

Every leadership role is part clouds (strategizing, inspiring, vision) and part dirt (doing, executing, details). People who go into a leadership role expecting 100% clouds will fail in their role. CEOs: for leadership roles, screen out talkers who want clouds but no dirt.

1. Founders and CEOs don’t have a good way to think about competitors. Some ignore them, others obsess over them. Neither is optimal. IMO, the right way to evaluate competitors is through a customer lens.

CEOs: When communicating a decision to your team, pls talk to 3 things: (a) who made the decision and who was consulted (b) guiding principles (c) alternatives considered Even if you don’t use a framework like SPADE, you need team to feel confident process was high quality.

The CEO of one of the best companies I've recently met, has a unique (and I believe compelling) philosophy around hiring: make managers prove themselves as ICs first. "We don't  directly hire into management. Instead, we like to hire them as ICs, and within 6-12 months we're happy to have them be managers (ie hire & interview with the expectation) but we want to make sure they will be strong ICs, so we can trust them with management. We've held this to be true across the board to date (operations, legal, marketing, etc.)  We may need to have exceptions in the future- but we definitely care maximally about this for technical roles (PM/Eng/Design/DS) since that is the core of our company."

Early stage B2B Founders: If you have to choose between one very large first customer (say $500k+ ACV) and ten smaller first customers (say $50k ACV each), the right choice (at least for venture funded companies) in most cases is the latter. Why?

CEOs and founders: here’s an example of how to convince candidates to look past titles. Read this email I received from a Series A founder today who was in the same dilemma:

Strategy and org structure are inextricably tied together. If your org structure is not aligned with your strategy, you will fail. Trivial example: if there is no Directly Responsible Individual / team for each strategic pillar (due to matrixed org), guess what will happen.

My friend @rob (cofounder of @Ro) is the best person to go to when you need a need a hard-to-find domain name. Snagged.com is awesome. Getting the .com is a big milestone for most startups!

I love working with people younger than me. At Google, I was the same age as my colleagues. At Facebook, I was ~10 years older. At Square, ~15 years older. And I just learnt that one of my colleagues at DoorDash was in second grade when I was a PM at Google. Young people constantly teach me to not succumb to the “I tried it before and it didn’t work” disease. By approaching every problem with fresh perspectives and first principles thinking, I’ve seen many problems solved in new and innovative ways. Their energy is —- energizing. It’s inevitable that the longer you work, the more likely it is that your colleagues are younger than you. Embrace it.

Startups: instead of rushing to add someone to your board, consider making them an advisor for 6-12 months. Do you enjoy working with them and trust their advice? Do your execs feel they are helpful? Do they add value to board meetings? Then and only then, add them to your BoD.

Startups: if you hear an eng hire spending too much time talking about how to scale things, likely not a good fit. Early startups are about speed of iteration, not scale. Every great co had a "monolith[ic piece of code]" that had to be refactored later. It's a point of pride.

This LinkedIn/resume inflation, while funny, is why hiring in startups is so difficult. And it’s so important to “hire slow and fire fast” versus the inverse.

Canadian friend: "JP Morgan did more diligence on me for a $2k limit credit card as a Canadian immigrant than they did for a $175M acquisition." forbes.com/sites/alexandrale…

Startup CEOs: if you haven’t yet done so, please make a list of the top 10 strategic partners / acquirers in your space and use your investors / advisors to get intros to a C-level person at each. Build and nurture the relationship over the years before you need to activate it.

CREDENTIALS DON’T MATTER Over the last few months, I’ve seen several A+ execs and operators flounder and fail at AI startups, while young “inexperienced” builders have crushed execution and performed superbly. It’s the biggest discontinuity in talent evaluation I’ve seen in my 25+ years in technology. All of one’s prior experiences, credentials, and traditional markers of success have become nearly irrelevant when the fundamental rules of the game have changed so dramatically. The shift to AI represents such a paradigm break that institutional knowledge often becomes institutional baggage. The executive who masterfully navigated enterprise sales cycles finds themselves lost when the product builds itself. The operator who optimized for predictable growth metrics struggles when the core capability improves exponentially overnight. Meanwhile, the 22-year-old who’s been fine-tuning models in their dorm room intuitively understands token economics, reasoning patterns, and capability scaling in ways that no MBA program ever taught. These “inexperienced” builders don’t carry the weight of how things “should” work. They don’t waste time trying to force AI capabilities into traditional product frameworks or business models. And so, they win. If you’re an executive wanting to find a role at an AI company, be humble. Put in the work. Use the tools and create a personal AI stack. Train yourself to think differently - probabilistically, not deterministically. Be open to an IC role if needed. It’s not magic, but it will take real work. If you’re an AI company founder, ensure your hiring process is not blinded by credentials. What matters is raw building ability (in EVERY role, not just Eng/Product/Design), comfort with uncertainty, and the ability to iterate and experiment exceptionally fast. It’s a new era.

Perpetual dissatisfaction I've now closely worked with/for several founders of $25B+ companies, and one characteristic I've observed in all of them: PERPETUAL DISSATISFACTION WITH THE STATE OF THE COMPANY. They are not satisfied, even as the company hits its goals, scales and grows, and even as most employees / investors feel happy with where the company is at. This dissatisfaction manifests itself most strongly in reviews and 1:1s. In business and product reviews, they push teams to think bigger, take more risks, move faster. In 1:1s, they urge their people to show more urgency, hire better, be more customer-centric. However well a team or person is performing, they ALWAYS have a list of 5-6 things that team or person could be doing better. Why is this the case? I've realized it's the case because they have such a huge and continuously expanding vision that they always see a big gap between the present and their vision for the future. This dissatisfaction / urgency / push transfers to the broader team, who pushes harder and stays hungry. I've also seen that as soon as a founder starts drinking their own kool aid and believes that the company has "made it", it's a leading indicator of the beginning of the end. Why? Because a founder's complacency immediately leads to the team becoming even more relaxed, and that torpedos the company. Note: I'm not advocating being an ass. Far from it. Expressing dissatisfaction is absolutely possible to do respectfully and without being a jerk. I've started using this as a tell for truly great founders. Never satisfied, never happy with the state of the company, never self-congratulatory. Obviously you can only see this after a few months of working with them. Leaders: examine your own behavior. If you are projecting a satisfied and complacent demeanor to your team, it's probably magnified 10x in their behavior. "My boss thinks everything is hunky dory". Add an edge to your interactions with your team. Be dissatisfied.

Cash flow >>>> Revenue.

hiring and culture at Julian Robertson’s Tiger.

India-based founders don’t know who to turn to as an alternate to SVB. Likely true for founders in other countries too. From what I hear, SVB was the only bank who’d bank a Delaware C Corp with founders who didn’t have a SSN. Unique, tech forward bank. Shame what’s happening.

As a startup employee, your hope should be that if your company fails, it does so quickly, within 6-12 months, versus slowly and painfully over multiple years. The opportunity cost and psychic pain from slowly dying companies is real.

Entrepreneurs and operators: the best memos and decks are written in the form of a conclusion followed by a series of assertions supporting the conclusion.

Investors and CEOs: The bar for technology companies to go public on US exchanges today is $500M of annualized high margin (75%+ GM) revenue. Klaviyo LTM revenue: $585M (80%+ GM) Instacart LTM ads revenue: $740M (80%+ GM) ARM LTM revenue: $2.68B (96% GM!) If you have a company doing $100M in annual revenue, growing 30% YoY, it's 6+ years away from hitting that $500M threshold. And if it's "only" growing 20% YoY at $100M, it's 9 years from hitting this milestone. Companies will need to stay patient for a VERY long period of time before tapping the public markets. Buckle down, execute, and figure out how to raise capital to get to the promised land, OR exit through M&A. Now, the bar might come down over time, as bankers + investors try to get lower scale companies out (or companies might be forced to test the markets since private markets are closed), but these micro / sub-scale IPOs will be painful for everyone - employees, founders and investors alike. Be realistic with yourself (and your LPs) about how many companies will really make it. Most will give up during this two decade march.

I'm sure every YC class has college dropouts, but this is the first class where I've met multiple teams comprised entirely of freshman CS dropouts from top schools. They all believe that AI has created a unique opportunity to build generational companies and that if they wait 2-3 years till they graduate, this opportunity will disappear.

ENTERPRISE SAAS STICKINESS - WHAT STICKINESS? This news from @Klarna should have every enterprise SaaS company shaking in their boots. If an internal team using AI can replicate 20+ years of work and customization from @salesforce and @Workday, to the extent the company doesn't feel the need to pay for these tools any more, everything we know about stickiness and durability of enterprise software needs to be rethought in the light of AI. In fact, their comments indicate that they were use AI to able to rethink the products from first principles and make them simpler and easier to use: "with the help of AI, the company is able to standardize and create a more lightweight tech stack to operate more effectively with higher quality". [LINK IN COMMENTS] I wouldn't be surprised if the mandate of the head of IT at large enterprises gradually expands to not just negotiating supporting enterprise software licenses but replacing them with custom-built products from the ground up, especially for the largest software products that cost 7-8 digits per year.

CEOs: The best functional leaders (legal, finance, marketing, etc) are businesspeople first, functional specialists second. Evaluate candidates through the lens of how they can use their expertise to problem solve for the biz versus through the lens of mastery of the function.

ENTERPRISE AI: BUILD AGENTS, NOT TOOLS In the past 2 weeks, I've met several AI agent tooling startups that have each realized that the biggest problem in large enterprises is NOT the tooling to build, test and deploy agents, but that these enterprises don't have the talent density / people / knowhow to build real life agents for complex workflows. So these startups are pivoting to: (a) building and running agents themselves and (b) offering their original service as part of running the agent. tldr Enterprise AI defensibility and value creation might lie in the full-stack approach to building, running and evaluating agents. Almost consulting-ish. Trying to be a pure tech platform might be a losing proposition in these early days. Some other hungry startup will own the agent and they won't use your technology stack.

Founder: “We want to do some quick customer discovery by showing customers mocks and asking them what they think.” NO. Customer discovery should be used to uncover customer problems / jobs to be done. Showing customers mocks is useless. What they say != what they will do.

We are seeing the first wave of white collar workers being laid off as a result of AI. Specifically, as law firms adopt AI tools for document processing, they are starting to lay off paralegals. Moving very fast. No white collar profession is safe.

PREDICTION One or both of @canva and @figma will enter the AI builder market in the next few months, likely with a product very similar to @boltdotnew or @lovable but tightly integrated into their existing products. There is no way these two very smart companies will tolerate being disintermediated by this next generation of AI-native companies, which are essentially verticalized builder (design + engineering) platforms. It also supports their stated strategy to democratize building. I say this with ZERO knowledge of the roadmap or internal discussions of these two companies.

It's very painful on iOS to not be able to "unread" text messages. Once I read a text message, I need to reply right away, or I risk forgetting about it. So now I just don't read a text msg until I know I have bandwidth to reply. Goes against the entire point of text messages.

Just heard from a friend who’s been at a FAANG for the past few years: “we are in a much better financial standpoint than before joining them”. This statement underscores a basic truth. While startups might be great from a culture and impact perspective, working for a handful of years at one of the Magnificent 7 is the absolute best, near-riskless way in tech to get to a level of financial security that allows you to feel comfortable taking significantly more risks in your career. If you have significant upcoming financial liabilities, consider the FAANG : Mag7 path, if just for a few years. It might not be the most exciting and fulfilling option (though many friends say the work is great) but it’s definitely the most pragmatic. Don’t blindly drink the kool aid; instead do what’s right for your personal situation.

I’m always awed by the times kept by entrepreneurs in India and SEA. I routinely do calls with them at 1-3am their time, and invariably find them energetic and fresh. I have to assume they work 16 hours a day (7-8 hrs during their workday and 7-8 hrs at night). Incredible. 🙇‍♂️🙌

Most startups are focused on defense today: cutting costs / extending runway. However, surviving the crisis doesn't mean you'll thrive once it's over. The companies that win will also focus on offense: product development, operational efficiency, M&A, building new capabilities.

Founders: please don’t give a VP title to anyone before you get to 100 people. I’ve lost count of how many founders I counsel on how to “deal with” VPs that they hired too early. medium.com/@gokulrajaram/the…

Convos with mid stage founders in the past week. Founder 1: exited 2 engineers in 1 day. Founder 2: mandated back to office last week. Founder 3: actively starting to track/measure productivity. All mentioned @elonmusk as inspiration. Things won’t be the same again.

1M ARR growing to 3M ARR in 12 months is no longer top decile for startups. It's 1M to 5M in 12 months. Everything is being reset at a higher level, including growth rates.

Important to note that SVB’s loan book (their assets) are quite good. They hold a ton of securities. They just didn’t have enough cash to meet withdrawal demands, and when that happens you are not a bank anymore. Fear and panic killed a healthy key ecosystem player.

Spoke with a friend at a ~$X00B pension fund who just made a direct investment in a pre-launch company. Spoke with a friend at a “seed” fund who put together a $100m SPV into a pre-IPO portco. tldr No rules in venture any more. No swim lanes. No stage is safe or protected.

A huge % of SaaS companies that were founded ~5-8 years ago and got to $10-50M ARR, are now building and upselling a new AI product to their current customers. This AI product likely cannibalizes their existing ("legacy") product, which in turn will slowly trend to zero. The existing product revenue cannot be underwritten by an investor due to its negative trajectory, while the new AI product is too small in scale to justify the prior round valuation. All this implies that the "AI transition" needs to happen very delicately and thoughtfully. If done wrong, the company might run out of money or need to take a painful and dilutive valuation haircut, if indeed there is even a round to be raised. SaaS company founders - if you fall in this category and are NOT doing the above (new AI product, cannibalizing your existing product), your long term survival might be at stake.

AI founder talking about why it's so hard to hire in SF today: "in SF, the AI labs have tremendously skewed engineers' perspectives. Every engineer either wants a package that is absolutely massive relative to their skills and experience, OR they want to be a founder."

ByteDance revenues 2018: $7.4B 2019: $17B (129% YoY) FB revenues 2013: $7.9B 2014: $12.5B (58% YoY) 2015: $17.9B (43% YoY) Not that it's a secret, but ByteDance is on an incredible trajectory. This is truly elite company.

1. Barrels and ammunition I didn’t overlap with @KeithRabois at @Square, but when I joined, his precepts were (and still are) all over the company. One of the most powerful metaphors - not least because of the vivid imagery - was that of barrels and ammunition.

CEOs: if you ignore seemingly minor issues, it sends a signal to employees that you are OK with the problematic behaviors manifested in the issue. This leads to the behavior becoming normalized, and the issues becoming amplified. A CEO friend told me how, when his company moved offices, they "lost" a few laptops. It seemed minor at the time, so he didn't really look into it. The next thing he knew, laptops started getting "lost" left and right. He had to start a full blown investigation, leading to many employees losing their jobs. tl;dr You promote what you permit.

EARNINGS CALLS AND INVESTOR PRESENTATIONS Startup CEOs: one of the highest ROI investments you can make to move forward your understanding of the market you play in, is to read the quarterly investor presentations and listen to the earnings call of the public companies in your space. It'll take 1 hour per quarter per public company, and will give an unparalleled view of the landscape and evolution, differentiators, GTM strategies and challenges, and future product roadmap. I have never done one of these where I've not had at least one "aha" or "omg" moments that has transformed the way I think about the space. Investor Relations websites have become much more easily navigable, and feature decks that are really well-done, clear and crisp, essentially pitch decks geared to public investors. Example from DataDog: investors.datadoghq.com/ In fact, I'd suggest you and your leaders listen to earnings calls together, since you'll benefit from the collaboration and cross-pollination of ideas that emerge. It's also great fun and brings people together, especially if you're all sitting in a room together while doing so! At companies I've worked at, we used to schedule it on our calendars well in advance, so it was locked in.

I'm excited to launch @MarathonMP with my friend @MBGilroy. Marathon will invest in and support founders who are obsessed with the problem they're solving, who understand the customers they're building for better than anyone else, and for whom their company is their life's work. We are high-conviction investors and committed to partnering and investing through the entire lifecycle of a company. Our name comes from our belief that building enduring companies requires patience, perseverence, resilience, relentlessness and a long-term point of view, reflected in the company's culture, strategy and actions.

I increasingly think of @a16z as a marketing and content firm that monetizes through venture capital. Their content marketing is as good as - or better than - that of any best-of-breed SaaS / Internet company. Curious about their CPA :)

I met a strong company today that's raising $10M from a Tier 1 investor. I asked the CEO why they aren't raising more. Best answer ever:"Our burn has historically been very low; at this point we don’t believe raising that much would make a difference in scaling the business." 💯

CEOs: if your marketing team says your company has a strong brand, ask to see how this strength manifests itself. A strong brand should lead to: lower cost of customer acquisition (CAC), higher customer retention or both, relative to competitors.

COMPOUND OR DIE Five years ago, doing a compound startup was the domain of repeat entrepreneurs who could raise tons of capital, and was otherwise discouraged by investors and advisors. Today, with plummeting software development costs and a 10x increase in competition, every AI startup needs to become a compound startup, and fast. Building an interlocking (compound!) system of AI agents that work together to strengthen each other and offer multiple related value propositions, is one of the few remaining ways to build a moat. Founders: while it’s critical to build a focused first product that solves a very specific problem for your customer, it’s just as important to rapidly expand to address adjacent needs, almost as soon as you have PMF with your first product. Achieving the elusive but critical balance between focus and expansion will determine if your startup wins its space or ultimately becomes an also-ran.

CEOs: It’s important to have a cordial relationship with the CEOs of your competitors and to meet with them on a regular basis. Why? Three reasons, which ultimately all boil down to humanizing your competitors and not having them feel like a black box.

Startups: Resist the urge to pursue channel partners early. No channel partner will engage with you unless you’ve (at least) hit PMF and they see/hear of shared customers using and loving your product. Instead, spend the energy on direct channels, customers and brand.

I had to raise a financing round for my startup in mid 2009, a few months after the collapse of Lehman and right in the midst of the global financial crisis. A few lessons:

Hiring an over-senior leader Just met the founder of a series A company who is having challenges with their VP Sales. The Vp Sales is a super senior leader with great experiences. Unfortunately, the company only has 2 AEs and 2 SDRs., so the leader is a fish out of water. The single biggest mistake I see founders make on the people front is hiring a leader who is 1-2 stages too senior. Typically this happens with functions that the founders are not intimately familiar with, so they rely on brand name experience / seniority to give them comfort that this person will take care of everything. So non-technical founders make this mistake when hiring a VP of Engineering or Product, while technical founders make this mistake when hiring a Vp of Sales or Marketing. Hiring a VP level person to lead a team of 5-10 people is like using a bazooka to kill a mosquito. Massive impedance mismatch. As the founder recounted to me, “Post the sales kickoff, we have a bunch of action items, but my VP Sales is unable to execute on them without delegating to someone else.” I believe in the maxim that you hire leaders for the next 18 months, not the next 5 years. So, founders should start by hiring front line managers, then think of promoting then to manage managers in a few quarters as the team grows. Investors - when a founder asks you “can you provide me good references for a VP of X role?”, you owe it to them to challenge the premise of the question, that they need a VP at all in the first place. Founders - hiring a VP or C-level person too early is almost certainly going to be very painful and lead to a lot of frustration (on both sides) and value destruction.

CEOs of early stage startups: the most dangerous employees are the “good” ones. The “bad” ones are easy to weed out while the “great” ones clearly stand out. It’s the good employees who you feel complacent about and don’t really move towards making a change. While good employees are an important part of teams at larger companies, I’m not sure that good employees are a fit for early stage startups. Every employee needs to be great or gone. This is a controversial topic. But the downturn has reduced the number of open roles at most startups, and so it’s important to have the very best person you can in every role. Don’t settle for good.

HOW TO BUILD A HIGH PERFORMANCE CULTURE Every CEO and leader wants to build a high performance culture. To do this, you need to be intentional about 3 things: managing out low performers, bear hugging high performers, and tying compensation to performance. 1. Manage out low performers: You must keep raising the bar by managing out the bottom 10% low performers. KPI: non regrettable annual attrition. For teams > 50, the minimum non regretted annual attrition should be 5%. If you see your company's non regretted attrition in the 1-2% range, that's not aggressive enough. 2. Bear hug high performers: You must ensure that the highest 10% performers are motivated, excited and see themselves progressing at the company. This means proactively giving them strong new opportunities, ensuring their comp over the next 1-2 years is strong, and constantly meeting 1:1 with them to listen to their concerns and express your appreciation for what they do as well as your belief that they are a pillar for the company. KPI: % attrition of top rated performers. I don't like an overall regrettable attrition metric, because what you really care about is your top performers. 3. Tie compensation to performance: Unfortunately the 4 year RSU/option grant is the enemy of this, because incoming employees get a large grant over 4 years, unrelated to their performance at the company. Many companies are rectifying this by making the initial grant 2 years long, and giving a new performance based grant at the end of Y1 (this grant vests in Year 3). And at the end of Year 2, give another performance based grant that vests in Year 4. So this way, the employee always has 2 years of stock comp ahead of them, and the comp is much closely tied to performance. KPI: % of employees on 1-2 year stock grant cycles, tied to performance. PS: Be careful of managers trying to game the system by classifying regretted attrition as non-regretted attrition in order to hit the 5% threshold (I've seen it happen). PPS: The move from a 4 year grant (one of technology's most hallowed institutions) to shorter grant cycles is wrenching but can be really powerful. And it MUST start from the C-suite. PPS: As you can see, the most important people to really focus your time on are the bottom 10% by performance (coach them or manage them out) and the top 10% by performance (bear hug). The middle 80%) can be "business as usual".

Series A founder: Our revenue is 3x what we were a year ago, with 0.5x the burn. I cut everything that was not essential, and took a first principles approach to every expense and figuring out the most efficient growth channels. The powerful combination of revenue growth and Opex reduction has got us here. We have half the cash we've ever raised, still on our balance sheet. Founders: it's absolutely possible to grow strongly while shrinking burn. Reject the sunk cost fallacy and take a zero based budgeting approach - justify all expenses starting from zero, versus starting with the previous budget and adjusting it as needed.

Text from a YC founder in the current batch: “half our batch is doing something with chatGPT”. Is the world ready for 150+ AI startups unveiled on demo day.?

Entrepreneurs: please remember that it’s the slope (growth rate) and quality (margin, retention) of revenue that drives valuation multiples, as much as - or more than - the quantity or scale of revenue.

Every Internet / software company I've spoken with, is aiming for profitability much faster / earlier than they would have 1-2 years ago. In many cases, this means getting to cash flow (CF) neutral with $25-50M raised, versus $250-500M earlier. Implications of this focus on profitable growth: (a) Top line growth is naturally slower than earlier (in some cases negative for a year or so) as companies "fire" bad customers and cut inefficient marketing spend. (b) It will take longer to exit (especially through an IPO) since companies will grow slower (see (a) above). We are back to the "12-15 years from seed to exit" situation. (c) Once companies hit CF breakeven, they will figure out how to grow while following the Rule of 40. (d) Companies might only raise 3-4 rounds (Seed, A, B, maybe C) before they reach the CF breakeven milestone. (Only) investors who participate before CF breakeven will have meaningful ownership. Post CF breakeven, founders will become extremely picky. Some might forego fundraising altogether and prefer to grow organically by investing their CFs (it's addicting to generate cash vs consume it!); some might ask for outrageous valuations (secure in the knowledge that they don't need the money). Essentially, the power dynamic will shift from investors (pre CF neutral) to founders (post CF neutral). Overall, this will lead to a net positive mindset shift in technology, with more companies and entrepreneurs aiming for profitability and sustainable growth sooner, vs chasing VC-fueled growth. There will still be a small cohort of outlier companies (very fast growers, infrastructure and other high CAPEX-companies) who raise $500M-1B before they go public, but they will be the exception.

HBR Case Study from 2025: You’re the founder/CEO of a $75M+ revenue company. You not only have PMF, you are the leading player in your category, a category that you created. You raised a humongous round in 2021 so while you’re not profitable, you have 5+ years of runway. Life is peachy, right? Not so fast. You have 3 problems: (a) Your growth has slowed down as buying cycles have lengthened. You were growing 50-70% YoY, now it’s 10-20% YoY. This dramatic, unprecedented slowdown has made you question your TAM, your category, everything. (b) Your new investors from 2021 - remember them? - are pushing you to grow faster. They want to see their investment grow 3x in 3 years. You don’t want to tell them that it’s instead probably shrunk by 70% in the last two years. (c) Your execs and employees are growing nervous. They’re questioning what the real value of the company is. You don’t have good answers for them. What do you do? Do you pour fuel on uncertain growth, increase your burn, shorten your runway? Or do you cut back, become profitable, grow more predictably? How do you mollify your stakeholders? It’s April 2023. You stand at the floor-to-ceiling windows of your penthouse (bought with the proceeds of your secondary sale in 2022), pondering these fundamental questions as you look out at the glittering (SF / NYC / Miami / London / Bengaluru) skuline. Your board meeting is this coming week. What is your strategy? What will you communicate to them?

What @rabois calls barrels, Slootman calls drivers. Critical to hire as many of this archetype as possible.

I am still numb and trying to process Susan's passing. It is an unimaginable tragedy because it just seems wrong for such a truly GOOD person to be taken away so early. Google would not be Google without Susan. She ran or deeply influenced every single product in the first 10-15 years of the company. I had the privilege of having her as my direct manager throughout my time at Google, and she shaped my career, as she did for so many others. As a manager, she modeled how to empower her people and support them in public, while coaching in private. She served her people, versus the other way around, by making life easier for us and clearing hurdles so we could get our job done. She massively and foundationally influenced my management philosophy. In a company full of engineers, she was a clear-thinking pragmatist, forcing us down from our ivory towers when we got too wrapped up in technical arcana or didn’t embrace reality. Her ability to speak the truth to power was legendary. One of my favorite Susan stories is from 2005, when we were discussing with Larry and Sergey the possibility of partnering with a consumer couponing service (coupons are a form of advertising). Midway through the discussion, one of L / S dismissed the whole premise with the statement: “nobody uses coupons - it’s dying”. There was dead silence in the room. L/S then threw down the gauntlet and challenged us to “raise your hand if you use coupons”. We looked awkwardly around, not sure if it would be a sin to admit that we were coupon clippers. And then: Susan calmly raised her hand and said “I use coupons.”. Seeing Susan (SUSAN!) do so imbued the rest of us with courage, and we followed her lead, till more than half the room “admitted” we used coupons, and the discussion was saved from being derailed. Every company needs a truth teller like Susan, to save them from themselves. But beyond her career, her accomplishments and her success, what I admired most about her was her personal characteristics: her humility, her approachability and deep care for people at a personal level (she saw how excited I was about ads and so moved me full time to it, despite her needing to take on my other projects temporarily), her dedication to her kids and her family, and her modeling of work-family balance (seeing her kids at the office playing and drawing while she worked and did meetings, was incredibly empowering; tens of thousands of Google employees indirectly owe her for her leadership setting up the Google daycare center). Susan, we will miss you terribly. Your legacy will live on through your kids, your family and through all of us who you coached and trained and showed that it was possible to be a good leader while also being a good person.

Met a pre-revenue AI startup doing a secondary as part of their seed round. Had to double check my calendar to see if it's 2021 again.

Enterprise-focused seed founder, upon finally receiving a reply after 8 weeks of non-stop following up with the decision maker: “I’ve learned that I just need to email every week until they either reply or tell me to f*** off” Yes. This is what it takes.

C-level execs: when you first join a company, don't be surprised or discouraged if you are initially micromanaged by the CEO, especially if that function didn't exist earlier. As a CPO told me: "You need to earn the length of your leash."

Brilliant tactic from Frank Slootman to raise standards: Ask people what they think of their own work.

The article in question? medium.com/@gokulrajaram/the…

Someone sent me this quote from @jack. The lessons I learnt from him are numerous, but a powerful one was that great design and great products are more about subtraction than about addition.

SELL BEFORE BUILDING I've now seen multiple episodes where PMs have used vibecoded / no-code prototypes to get 2-5 customers to sign LOIs or even contracts, and then use this "proof of real demand" to build a MVP. In some cases, customers have been so eager that they've started using the prototypes instead of waiting for the MVP. CEOs: for most B2B apps, gone are the days where you build, launch and hope someone buys. Turn this on your head and pre-sell prototypes, get real demand and use that as a barometer to build.

BOARD MEMBERS A founder with multiple VC partners on their board told me that their favorite board member is the one who doesn’t panic and start asking “omg what’s going to happen to the company” every time the company faced a challenge or crisis, but instead goes into problem solving mode and asks “how can I help you”. Ironically, this is the board member with the smallest fund size of the three. An example, this board member offered to backstop the company if a fundraise fell through, while the larger fund partners stayed silent. Board members: CEOs want you to (a) stay calm and not panic: after all, you have a portfolio; the founder just has this one company, (b) show you care about the CEO and the company, not just about your investment, and (c) problem solve alongside the CEO, bringing your capabilities and resources to bear at company-defining moments instead of shying away from the moment and hanging the CEO out to dry.

Sign of the times: a stealth startup did a podcast to try to recruit software engineers. The ration of investors to engineers reaching out to them (as a result of the podcast) was 10:1.

New user onboarding and activation is one of the most critical things for teams to test. Unfortunately it’s also one of the hardest, since people don’t go though the NUX flow more than once as a matter of course. So most teams stay blissfully unaware of what new users experience.

CHARGE 5-25X MORE FOR YOUR CONSUMER SUBSCRIPTION PRODUCT Consumer CEOs: Charging $20 monthly / $200 annually for your product means that you need 1M subscribers to get to $200M ARR. Given the high churn with consumer SaaS products (4% per month not uncommon) you will need to constantly keep filling the top of funnel just to tread water. Yes, ChatGPT and Claude have built large businesses with this low priced model, but they are the exception, not the rule. They've also each raised $5b+. Consider instead, a plan where you charge ~$1000 per year, or even ~$5000 per year. Raising your prices by 5-25x does two things. First it, dramatically lowers the number of subscribers you need to get to real scale ($X00M ARR). As a side benefit, each subscriber is much more valuable, so you can invest in customer succes and retention. Second, it massively raises the bar on the value your product need to deliver. Let's talk about the second thing. How do you raise the bar on value? You do it in four ways: (i) REFRAMING the role that your product plays in your customer's life (and finding a niche customer segment that cares about this) (ii) DELIVERING said value to this niche customer base, and (iii) COMPARING it to an amount the customer already pays for a comparable service. Let's take an example. Calendaring systems like Calendly are either free for users or charge $10-15 per seat per month. However, what if such a system could reframe their product as an AI executive assistant, and subsequently build out this functionality? They can then compare the new price of $250 per month to the cheapest outsourced EA service (Eg: Athena) which charges $3000 per month. Obviously, the product needs to deliver value equivalent to an EA, but with AI, this is much more viable today than it was a few years ago. One may argue that only a small % of people will pay $250 per month for an EA. But that's OK. Due to our higher per-customer revenue, our new system can afford to spend a much higher CAC to target and find 100,000 people (solopreneurs, SMB owners, coaches, etc) who will pay $3000 per year for this service. And also invest in a team to keep them happy and satisfied and not churn. 100,000 * $3000 = $300M per year! The economics become similar to a SMB-style business vs a consumer business. So, to summarize: 1. Reframe the role of your service in your customer's life, ideally comparing it to an existing in-real-life service 2. Articulate a niche customer segment who cares deeply about this IRL service 3. Build this new, more expansive product that delivers this service 4. Price it much higher than earlier, comparing the value to what your target customer would pay for this service in an alternative world 5. Profit Building a profit pool from a higher priced product will earn you the right to then build a new lower-priced product and go broader. This is the playbook that Tesla followed. tldr with rare exceptions, I think most consumer products should start with a high priced version, dominate a niche customer base, and then over time, go broader with lower priced version. Most of them are doing the opposite, making survival hard.

Enterprise pricing: Have MULTIPLE leverage points to use when negotiating. Founders: the conventional wisdom around pricing your product is to keep it simple. Unfortunately this works against you when you’re dealing with enterprise procurement teams. These team are the most sophisticated negotiators you will ever meet. They are single mindedly focused on extracting value for their company. If your pricing is too straightforward or simple, they will hone in on this and beat you down. And it will get worse with every renegotiation. As someone who, in his first PM job, ended up pricing his hardware product below Gross Margin after an enterprise negotiation, take it from me : you cannot go into an enterprise pricing negotiation with a singular point of leverage. You need complexity in the form of multiple leverage points. This is the only way to not give away your entire margin or profit pool. As an example, take a payment processing company selling to an enterprise. Their rack rate might be 2.5%, and they approach the enterprise with a seemingly great tiered deal, which the lowest tier being 1.8% above $100m in volume. (Their cost is 1.6%). Neat and clean, right? Not quite. A sophisticated enterprise negotiator will have a complete understanding of the processor’s cost basis, as well as what % of the processor’s business will be represented by the enterprise. Their counter will likely for their entire volume to be at or below cost. And they won’t budge, since their legacy payment processor offers them (a worse) product at 1.5%, so they have a good BATNA (best alternative to no agreement). The issue here is that the processor has left itself vulnerable by having a single leverage point - the payment processing rate. They tried to add a volume tier, but it’s not separate enough from the rate to use it effectively as a bargaining chip, not against enterprise negotiators. So what should the payment processor do? They must introduce a completely separate axis of negotiation. Essentially a new product or service. Here’s two examples: 1. “Sure thing, we will give you 1.6% for your entire volume. But this will necessitate significant support resources from us. you need to pay us $20k per month for enterprise support. “ Enterprises are perfectly happy to pay a predictable amount for support. This might work well for the first time negotiation. 2. Decompose the payment product into a bare bones payment product, and separate out premium features such as chargeback protection. “Ok, we will match your legacy processor on rate. But if you want chargeback protection, it’s $0.05 per transaction.” This might work as a backup to #1 above, or in the renegotiation after year 2. 3. Inevitably, at some point, you will need to be prepared to respond to price reduction ask on product 1 by getting the enterprise to take product 2. Obviously this decision is not a pure procurement decision, so you’ll need to get the product or business decision makers bought in well in advance. Having your enterprise customers using a suite of products, gives you massive pricing flexibility. That’s the ultimate nirvana / goal to get to. It’s important for new pricing modalities to ideally be a different pricing regime than the primary one. The second one (#2 above) priced flat fee per transaction vs a % of GPV, so the enterprise procurement team cannot try to bundle the two in their negotiation. TLDR Enterprise pricing is complex and you need to recognize and appreciate this. Ensure that you go into an enterprise pricing negotiation, armed with multiple axes of leverage. Be comfortable with complexity. Simple is not better in this situation.

My kids upon hearing that @DoorDash and @Caviar are joining forces: “Finally, we don’t need to feel guilty while using DoorDash because our dad works at Caviar”. 😂

I've now served on ~10 private and public boards over the past 12 yrs. 2 observations:(a)Founders are much more assertive today; a decade ago, investors dominated board meetings.(b)Meetings are much more engaging and focus on key strategic issues,vs on financials and fundraising.

Top 2 characteristics of successful execs at any company: (a) get s*it done (b) great people judgment. That’s it. That’s what CEOs want in their execs. Across every function.

Kathy Xu, one of China’s top venture investors (eg: she led JD’s Series A in 2007) counts Kanye West’s mom as one of her top formative influences while studying at Nanjing University.

CHIEF PRODUCT OFFICER HIRING Over the past few years, I've seen several top private tech companies part with their Head of Product / CPO in less than a year. The symptoms are many, but the root cause is the inability for the product-centric CEO to treat the CPO as someone more than a roadmap executor, while the CPO desired to be more strategic. Post CPO exit, in some cases, the CEO has taken on the CPO responsibilities and eliminated the role; in other cases, the Head of Eng consolidated design and product under them to form a unified EPD team. Note that the importance of the PM role is not in question at any of these companies; it's the (need for the) role of the CPO / Head of Product. Underscores that the CPO role is one of the hardest ones to successfully hire for. CEOs: Your unique role as CEO is not to assess if these candidates can successfully build products, but rather to determine if they can successfully build products with YOU. CPO candidates: Probe deeply for why the CEO wants a CPO. Is it to delegate tactical work? Or is to truly be a thought partner?