This week, we’re sharing an article based on our most popular podcast episode of 2024.

Everything in Business is About Fighting Entropy — Here’s How Rippling Does It

At Rippling, all the functional leaders have a running joke: “Who is MacInnis's injured bird?”

It's not a question about ornithology. They are referring to COO Matt MacInnis’ surgeon-like approach to executive attention.

While most startup executives spread themselves thin—jumping between financial forecasts, hiring plans, and product roadmap decisions—MacInnis operates with the precision of a skilled physician: identifying his most critical patient, bringing them to the operating table, and giving them his undivided attention until he's solved the underlying problem.

“Everything in a business is about fighting entropy,” MacInnis says. “Everything I do today in my job at Rippling—where we have a massive growth rate on top of a very large base of revenue—all day is to fight entropy. It’s the feeling that if I take my eyes off of a project, it'll slow down a little bit. Without the intensity that I bring to each of these projects, it will drift in terms of velocity or precision.”

As a former founder, MacInnis spent nine years building Inkling and leading the company as CEO through its acquisition. These days, he’s focused on scaling Rippling into a full-service workplace management platform, a role he stepped into early on in the company’s lifecycle. And as more people enter the picture, entropy is a force that becomes every team member’s responsibility to combat—but senior execs are most acutely responsible.

In this exclusive interview, MacInnis shares his unconventional playbook for how startup executives can become more deft at both diagnostics and treatment. His advice is two-fold: tactics for making the organization better and strategies for making you a better exec.

With advice that starts out on the milder side (like how to leverage impatience into velocity) to some hotter takes further up the Scoville scale (like his fundamental rejection of asking for advice), MacInnis pulls no punches when it comes to divulging all the practical wisdom in his repertoire. The podcast interview with MacInnis was our most downloaded episode of 2024 for a reason.

The lessons he shares will help any leader become more effective no matter where they sit in the org chart—whether you’re a founder, an exec or still climbing your way up the ladder.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-Is great operations the sneaky undertow that sinks multi-product bets? Shreyas Doshi makes the case.

-You can now watch this TedNext talk from Molly Graham, one of our favorites here on the Review, about why winners forget the corporate ladder and focus on taking risks.

This week, we’ve crowdsourced a list of meaty self-reflection prompts from some of the most thoughtful founders we know.

25 Hard Questions Every Founder Should Ask Themselves

We’re hurtling toward the last stretch of the year. Even as the ink dries on 2025 plans and product roadmaps, many founders are taking on a less official, more solitary ritual: Self-reflection.

So if you’ve found yourself in an introspective mood this time of year, we’ve cooked up some food for your thought. We spent the past month reaching out to founders from all across the startup ecosystem with this question:

Which reflection prompts do you find most useful as a way to step back and think about your business, your team or your own leadership?

This turned out to be an easy ask from this naturally self-scrutinizing crowd. Founders generously offered up the questions they keep in their back pocket to return to as they navigate every juncture of startup building.

We heard from a mix of seasoned repeat entrepreneurs, plucky young founders, and long-time builders who’ve taken the leap to start up — folks like Superhuman founder Rahul Vohra, Clay co-founder Kareem Amin, Puzzle co-founder Sasha Orloff, and former Maven co-founder Wes Kao, just to name a few.

Some founders shared questions that serve as daily reminders to speed up their decision making and recalibrate their priorities. Some shared the questions they ask themselves to zoom out and take a hard look at their product strategy. Others put forward prompts for more periodic reflection on how things are going and where the company is headed.

Here’s a sneak peek:

• Did the work I do today actually move the needle on making the company successful?
• Are we pursuing this product direction due to inertia or because it’s right?
• If I was starting this business again today from scratch, what would I build to win the market?
• What’s the conversation I’m avoiding?
• If we close 100 more deals that are just like this one, will we be happy or sad?
• Where are we on the continuum of chaos and control?

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-A new interactive essay format from our friends at Every

-Why you need multiple leverage points to negotiate enterprise pricing

-A framework for understanding what makes a winning marketplace

This week, we're bringing you our latest episode of the In Depth podcast 🎧 with Figma's Chief Product Officer, Yuhki Yamashita.

How Figma taps into taste, simplicity, and storytelling | Yuhki Yamashita (CPO at Figma, ex-Uber, Google, Microsoft)

Listen now on Apple, Spotify and YouTube.

Today, we're coming to your inbox with something a bit different. Instead of a new Review story, we thought we'd share a recent conversation from our popular podcast, In Depth. (Next week we'll be back with more written goodies—there are a few exciting pieces we're cooking up to close out the year!)

If you're not familiar with In Depth, it's hosted by First Round Partner Brett Berson, in conversation with some of the sharpest founders and operators in tech. Each episode tackles different company-building firsts that skip the talking points and go deeper into not just what to do, but how to do it.

This week, Brett sat down with Yuhki Yamashita, the Chief Product Officer at Figma. Previously, he was a product and design leader at Uber, where he orchestrated the redesign of the rider and driver apps, and he also had PM stints at Google and Microsoft.

Here's a preview of what's in store in the episode:

Why Figma worked

Yamashita explains the offbeat approach that Figma's founder Dylan Field leaned on to rally support from early evangelists. He also unpacks why "every good product narrative has a little bit of tension." In Figma's case, the thought of having people (like your company's CEO or Art Director) jumping into a designer's work-in-progress files was a bit of a controversial bet at the time.

How Yuhki came to join Figma

While Figma would go on to become a decacorn, Yamashita admits he didn't have the foresight at the time to predict this atmospheric rise. Instead, he was drawn in by the product's rallying crying that "design shouldn't be only something designers do," and his own conviction in the product that would make jobs like his better.

How Uber, Google, Microsoft and Figma approach building products differently

Across each chapter of his product career, Yamashita has pulled different pages from the playbooks top companies use to build impactful products.

-Microsoft: "At Microsoft, you could be the PM of the 'undo' feature of Excel. There was a culture of extreme attention to detail."

-Google & Uber: At both Uber and Google, PMs were given a much broader product space, and as such had to be more comfortable making bets (and rallying folks around those bets).

-Figma: The nature of Figma's product is that everything is a work in progress. It's a much more fluid way to build product, Yamashita explains.

Figma's approach to going multi-product

As Figma has begun to expand the product suite beyond the core offering (like FigJam and, more recently, Slides), Yamashita explains how this multiproduct expansion has changed how the product team works. From prioritizing what to build next, to how Figma approaches resourcing, He also unpacks why "the best products come from a bit of internal conflicts."

Why aren't there more designers-turned-founders out there?

There are a few notable designers who later became founders out there in tech (Airbnb's Brian Chesky and Linear's Kaari Saarinen are two that come to mind). But designers are largely unrepresented in Silicon Valley's C-Suite. Yamashita points to commerciality as one such explanation here.

Storytelling as the secret weapon in your product toolbox

"When you end up in a conversation with a customer that's just about features, that's not a conversation you want to be in," says Yamashita. He explains the Figma approach to product storytelling, including his "one screenshot" test for evaluating whether a product story is hitting the mark.

You can listen to the full episode on Apple, Spotify YouTube, or wherever you get your podcasts.

Thanks, as always, for listening and sharing!

-The Review Editors (and In Depth producers)

Here are the timestamps for the episode:

(00:00) Figma's early days

(06:21) Product culture across companies

(10:52) Knowing when to change things

(14:50) How business goals impact product expansion

(18:10) Advice for going multi-product

(21:40) The skills of a “0 to 1” PM

(24:46) Identifying entrepreneurial talent

(26:16) Why aren't there more designer founders?

(32:32) How Figma launches new products

(38:29) “0 to 1” versus “1 to 10” talent

(43:11) The role of storytelling at Figma

(46:32) How Figma prioritizes product

(52:21) Advice for product storytelling

(56:12) “Good” vs “extraordinary” product managers

(58:31) Why product simplicity matters

(61:02) The importance of taste in product and design

(65:06) The biggest influence on Yuhki’s product thinking

This week, a three-time founder opens up about his quest for intellectual honesty after a decade and a half in the startup arena.

The Uncomfortable Truth: A 3X Founder's Guide to Intellectual Honesty

Nobody wants to be wrong. Especially not founders, a famously stubborn (and hopeful) bunch. And for good reason — a strong will is requisite to turn “what ifs” into a reality.

But that same dogged optimism can lead founders to turn a blind eye to meaningful feedback or warning signs when things aren’t working. That’s why Bob Moore thinks a healthy dose of intellectual honesty is a must-have for founders.

Intellectual honesty isn’t about always being right. It’s about always seeking the truth, even if it contradicts your beliefs (and hopes). It's holding up a mirror to the sneakier confirmation biases we fall for to protect our egos.

Here’s how Moore defines it for founders: “Being intellectually honest means being willing to understand the difference between noise and signal in the things that aren’t working in your business.”

It’s a quality he wishes he had more of back when he was building his first startup, an analytics platform called RJMetrics. Despite launching in the wake of the 2008 downturn, RJMetrics bootstrapped its way to product-market fit. But several years later, Moore and his team overlooked signs that the market was moving in another direction and competition was quietly forging ahead — and they fell out of product-market fit.

“If I had to distill the lesson from that experience down to something that I wish I had more of back then, and something I’ve worked on a lot since, it’s this idea of intellectual honesty. It’s something that all founders need to care really deeply about,” he says.

In this exclusive interview, Moore lays out a guide for how founders can put intellectual honesty into practice, alongside examples of the confirmation biases that can be most deceptive for founders and how he combats them now as he builds his third startup, Crossbeam.

A few of the biases he bumped into:

• Chasing market trends or passions when choosing a startup idea — without being honest about your own strengths. This was the story of RJMetrics. “We went in as mercenaries. We wanted in on this startup game and big data was increasingly a thing. I knew how to write a damn good SQL query. But that was all we had,” says Moore. “I didn't have strong conviction.”
• Having a “they’re the dumb ones” mentality. One of the first warning signals that the market was moving away from RJMetrics was a rising churn rate. But at the time, Moore chalked it up to their customers making bad business decisions. “When you notice you’re becoming more dismissive of people and things that you think don't know as well as you do, because they haven't been doing this as long as you, it's time to do that intellectual honesty check and see if maybe there's something else going on,” he says.

Moore’s advice is geared toward the founder seat, but his truth-seeking tactics are worth a read for anyone in the business of building with integrity.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-A complementary read from Wes Kao on intellectual honesty in the workplace

-Molly Graham’s advice for working at a rapidly scaling startup

-Notion co-founder Simon Last on building Notion AI

This week, a growth expert behind some of the biggest marketplace success stories shares his commandments for the 0-1 stage.

How to Build a Billion-Dollar Marketplace — Do’s and Don’ts from the Growth Expert Behind Grubhub, Pinterest, and More

In the early days, Grubhub was “embarrassingly bad” on a software level, admits the company’s first marketing hire, Casey Winters.

How bad could it be? We’re talking fax machines in the 21st century. “When someone ordered food from Grubhub, we sent a fax (yes, a fax) to the restaurant with the order. On the fax was a confirmation code. Then, we sent an automated call that asked for the confirmation code. If you typed that in, we knew you were making the order,” he says.

But Grubhub got away with this hacky approach early on because, when it comes to marketplaces, the product you’re offering is your supply — not your software.

It’s a bit of a cheat code. In SaaS, teams can spend years building, prototyping, designing and layering on slick features. Marketplaces don’t need the most elegant tech in the beginning, consumers will forgive some clunky software if they’re getting connected to loads and loads of choices — whether it’s for food delivery, handmade goods, or drivers.

But stocking your fledgling marketplace with tons of high-quality suppliers is far from straightforward.

“When you’re building a marketplace, you’re tasked with generating demand and supply — so it can take longer to get the product to fully unlock. Marketplaces tend to take longer to reach product-market fit because you're effectively building for two customers at the same time,” he says.

How have companies like Uber, Etsy, Faire and Doordash navigated this cold start problem and built scalable, multi-billion dollar marketplaces? What did they do differently from the also-rans? In this exclusive interview, that’s what Winters unpacks in great detail.

He’s carved out a storied career as a marketplace growth maven. Including his 5 years at Grubhub, Winters also led the growth team at Pinterest, and served as the CPO of Eventbrite (through the trial-by-fire of the pandemic, no less). Now, he advises and angel invests in up-and-coming marketplace startups.

He demystifies the 0-1 process into a simple punch list of do’s and don’ts, with plenty of case studies to put the ideas into practice.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-Want to learn how to make decisions like a VC? First Round Partner Brett Berson is hosting a new Maven course with bestselling author and First Round’s Special Partner focused on Decision Science, Annie Duke.

-How to know it’s time to pivot your startup (and why AI makes it easier).

-A handy cheat sheet with 5 proven prompt engineering techniques.

This week on the First Round Review, we’ve got a seriously detailed guide to help you tackle one of the most dreaded organizational rituals: annual planning.

Annual Planning Sucks — A CPO, CRO, CFO, and COO Share Advice on How to Make it Better

Annual planning has always been painful, with many viewing it as tons of paperwork and processes that don't ultimately add up to impact.

But as teams across the tech landscape have embarked on the process this fall, we’ve observed that planning in this era is particularly challenging. Every new LLM rollout now risks upending your plans, whether it’s scrambling your product roadmap, changing your headcount calculus or ballooning your budget for new tooling.

That’s why we’re especially grateful that Jiaona Zhang came to us earlier this year to team up on a focused mission: Put together a detailed resource that helps execs put together pain-free, actually useful annual plans.

You might recognize Zhang from her two previous Review articles on building minimum lovable products and climbing the product career ladder. She’s built up a stacked resume, leading products teams at Airbnb, WeWork, Webflow, and now, as CPO at Linktree.

“What I’ve learned in the last decade is that while there are some important universal principles — like constraining the timeline — you need to commit to thoughtfully tailoring the process to your company,” she says. “‘I’ll just do what I did at my last startup’ or ‘Let's figure out what X company did and copy it’ sets you up for a lot of heartache. You shouldn’t copy-paste processes without a lot of introspection. Every company’s planning process needs to be optimized for what their problems are, the market they’re in, and the team they have to execute the planning.”

To help founders and startup execs do just that, Zhang brought in an annual planning brain trust of sorts, tapping her network to find sharp execs across different companies and organizational functions. In addition to Zhang, you’ll hear from:

• Cristina Cordova, COO at Linear, formerly Head of Platform & Partnerships at Notion and Business Lead at Stripe (where she joined as the 28th hire).
• Stevie Case, CRO at Vanta, formerly VP of Enterprise and Mid-Market Sales at Twilio.
• Rama Katkar, CFO at Notion, formerly VP of Finance at Instacart and SVP of Corporate Development & Strategic Finance at Credit Karma

This piece is detailed and long (even by our standards) but it’s worth diving into (or at least bookmarking for later). There are templates. Stories from stellar companies. Tactical examples. Previews of how they’re incorporating AI into their 2025 annual plans.

Here’s a sampling of what you’ll learn:

• How to put together your strategy doc, working with founders to channel their vision.
• Tips on avoiding the usual pain around headcount and forecasting.
• Why you should time-box the time you spend planning, and instead invest it into designing the right org chart.
• Crafting the right check-in cadence, with a scorecard template and pre-mortem question to set you on the right foot for 2025.

Thanks, as always, for reading and sharing.

-The Review Editors

P.S. If you prefer to listen, like many of you, we’ve been playing around with the incredible NotebookLM. Listen to this “conversation” here.

Recommended resources:

-Lenny Rachitsky walked us through his terrific annual planning process from Eventbrite and Airbnb on the Review several years ago. We recommend reading it if you missed it.

-Marketers: Check out this annual planning template from Emily Kramer.

-If you're anything like us, and can't stop playing around with NotebookLM, this podcast episode with Raiza Martin (the PM behind the product) is a delightful listen.

This week on the First Round Review, we're back with another installment in our Paths to PMF series, this time with Replit's CEO and co-founder Amjad Masad.

Replit’s Path to Product-Market Fit—The $1 Billion Side Project

The startup world loves its archetypes—the wunderkind entrepreneurs who've been dreaming up business ideas since their lemonade stand days.

But Amjad Masad’s journey to building Replit began not with dreams of entrepreneurship, but with a singular vision: to democratize the power of software development. Leading a business was more of a means to an end.

In 2008, as a CS student in Jordan charting his path to Silicon Valley, Masad was unknowingly laying the groundwork for a billion-dollar business. His "mad science experiment," Repl.it, started as a simple solution to a frustrating problem: the inability to collaborate on code in real-time in the browser. He assumed this task would prove to be difficult, since no one had done it before.

"It turns out, the prototype was easy," Masad says. "I created a text box where you could input JavaScript, click a button, and it would evaluate the code. There was also a way to save and share it, and I immediately got feedback that what I was building was useful, which is what every developer wants to hear."

But despite these early signals of product-market fit, Masad shelved it. He more or less abandoned the IDE project he started, and went on to pursue a career as a software engineer, making pitstops as the founding engineer at Codecademy and starting the JavaScript infrastructure team at Facebook.

Even without Masad's active involvement, Repl.it continued to gain traction. "Even though Replit by this point had been abandoned and parts of it were broken, developers still kept coming back to use the product because there was nothing else out there," Masad says. By 2016, it had amassed over 100,000 users, mostly students and self-taught programmers who discovered it through word of mouth (pretty impressive for a project put on ice!)

To Masad, the pathway to fulfilling his vision of equal access to software creation had crystallized. Which meant it was time to take a real crack at building a business.

Fast forward to 2024, and that experiment has evolved into Replit, a $1B company with 30 million users and over $200M in funding.

In the latest installment of our Paths to Product-Market Fit series, Masad takes us on Replit's unconventional journey from college side project to billion-dollar AI startup. His story is stuffed full of unique insights and founder lessons — here’s a sneak peek at three of them:

• Don't be afraid to go broad when others go narrow: "I decided to place a bet on becoming a general purpose platform,” Masad says (a gutsy call when most were going all-in on JavaScript). “I thought we shouldn't be in the business of betting on certain languages, rather, we should support as many languages as we can.” This became the secret lever they pulled to scale ahead of the competition.
• Invest early in emerging technologies: Just last month, Replit rolled out Replit Agent, its agentic code-writing assistant tool, that lets users create live applications from just a few lines of text. But Masad laid the groundwork for that innovation long before trying to build anything for customers. "It wasn't until GPT-2 that we started actually writing code and experimenting with it,” Masad says. “But understanding the machine learning stack was so hard and the training was still inaccessible so, while we had some experiments that were exciting, we never shipped anything."
• Focus on experimentation over immediate commercialization: "My advice for founders entering the space: Think about all the cool projects there are to do and give yourself enough time — especially if you're still in school — to pursue that,” he says. “Don't start with the intent of starting a company or commercializing. Instead, ask yourself: what is something really interesting and cool that I can do with this technology?"

Thanks, as always, for reading and sharing.

-The Review Editors

Recommended resources:

-This essay on the importance of data when making decisions in the engineering industry

-The best way to test Web APIs

-5 tips for planning your career like a product from Ami Vora

This week on The Review, Alex Kracov spells out the channel strategies, messaging drills and big bets he invested in as the first marketing hire at Lattice, and which tactics he’s putting to use once again now as CEO and co-founder of Dock.

Passing the Button-Clicker Test, and Other 0 to 1 Lessons from Lattice’s First Marketing Hire

Alex Kracov has a revealing trick to identify the real doers of company-building: what he calls the “button-clicker test.” To build things from scratch, you need to be able to take matters into your own hands, like scrapping together a website mockup in Figma or typing up some landing page copy.

That unglamorous click-clacking made up most of Kracov’s days back when he was employee #3 at HR tech powerhouse Lattice, where he was the first marketing hire. He was tasked with the simultaneously demanding work of not only shaping the marketing strategy, but executing it — from building a website to designing conference t-shirts to publishing blogs and SEO articles.

Kracov has found that too many early marketers are only skilled at the strategy component. “One of the biggest mistakes people make with early marketing hires is they have someone who can talk the talk, but when it comes to actually doing things, they have to go hire people to click the buttons,” he says.

In this exclusive interview, Kracov reflects on how he toggles between high-level decision-making and daily to-dos — and shares his order of operations in his first year as a team of one. From how he worked with the founder to nail down positioning to the experimental approach he took for setting up Lattice’s marketing channels, Kracov opens up his exact playbooks. He also brings things full circle to talk about how he’s thinking about this work now as the founder of Dock, a revenue enablement platform.

Whether you’re a founder or a marketer, Kracov has plenty of advice for the uniquely challenging slog of zero-to-one marketing (he’s tackled it in both seats, after all). Here’s a sampling:

• Stand up a proper website as soon as you can. Even if you’re still putting the finishing touches on the product, your website should be your first priority. “The best thing about a website is you can do a bit of magic trick in the market. You can feel so much bigger than you are if you nail your website and invest a little bit more into the design of the site.”
• Start wide with your channel strategy, then narrow it down once you figure out what sticks. “There are so many different directions you can take marketing,” he says. “Cast a wide net at first — then pick a few channels that really work. And bonus points if you enjoy doing them yourself.”
• Don’t obsess over numbers in the early innings. Slow-burn channels like community and SEO can take years to compound, so don’t expect flashy metrics right after you launch them. “You might see a really cool experienced leader sign up for the Slack channel,” he says. “Or maybe someone said something really nice about the blog. Those signals, while qualitative, can give you a sense of whether or not something is working. And you can be confident that all these little things, incrementally, help the go-to-market function.”

It's a rare peek behind the curtain at what the first year in the founding marketer's seat looks like as a startup finds its sea legs.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-As planning season gets underway, revisit this product prioritization thread from Shreyas Doshi.

-Thinking about investing in a B2B conference? Here's how to stand out amidst the sea of booths.

-How to sharpen your judgment and make better decisions.

This week, we asked founders to recall the moment they knew their startup was primed for takeoff — long before they had any splashy numbers to show for it.

Non-Obvious Signs of Early Startup Traction — And How to Spot Them

A viral launch. Leads pouring in. Off-the-charts usage.

These are the classic hockey-stick-shaped trends founders hope for in the opening stretch of a startup’s life.

Metrics are deservingly the gold standard for assessing your progress toward PMF and beyond — it’s why we wrote a 10,000+ word essay with detailed benchmarks from the early days of now-established B2B startups like Looker, Vanta and Plaid.

But hard numbers aren’t the only way to gauge how things are going. Especially in those first few months (or even years) when you can’t calculate the typical leading indicators yet, how do you know if you’ve got something that could really work?

For the latest article on The Review, we revisited the conversations we’ve had with founders throughout our Paths to PMF series to unearth the most surprising answers to that question. For many of these founders, the earliest sparks of traction were subtle, or didn’t seem promising at all — easy to miss in the moment. But in hindsight, they stand out as the harbinger of the success that followed.

The signals these founders identified came from a range of sources: their customers, their industry and even their own mental state. Here’s a taste of their answers:

• Customers are complaining about the product. At first blush, a ton of grievances from early customers might make you think that you’ve built the wrong thing. But for Gong’s Eilon Reshef and GOAT’s Eddy Lu, getting complaints from customers was actually an indicator that they cared enough about the product to give the founders honest feedback.
• There’s some impressive competition. The sheer existence of competitors may not mean much, but the way Vercel CEO and founder Guillermo Rauch sees it, when there are other players in the market who make you sweat, you’re onto something. “When something is really needed, you’ll find there are lots of very intelligent people at other organizations trying to build a version of it.”
• Founder morale is rising. Productboard CEO and founder Hubert Palan took an unorthodox approach to evaluating the startup’s progress: He turned inward. “I measured my own happiness as a proxy for the customer's happiness. At first, it was completely up and down. Eventually, I started feeling much better about where we were headed once the feedback became consistently more positive.”

These stories offer an encouraging reminder to builders just starting out that progress isn’t always obvious in real time. Just because the numbers aren’t there yet doesn’t mean they aren’t on the cusp of ticking up and to the right.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-Tara Seshan’s framework for communicating tradeoffs effectively (you can find more of her product wisdom in her Review article)

-The trendy growth hacks that don’t actually work

-Review favorite Will Larson’s thoughts on how to translate executives’ ambitious ideas into practical tactics

This week on The Review, a tech marketing maestro shares her reflections on founding and scaling the org at breakout startups.

Why Startup Marketers Should Be Diagnosticians — Advice from OpenAI’s and Stripe’s First Marketing Hire

Marketers may not have MDs, but according to Krithika Muthukumar, the best ones have a knack for puzzling out the needs of a business the same way doctors solve a medical case.

“The job of a marketer, especially in the early days of a startup, but on a constant basis, is that of a diagnostician,” says Muthukumar. “Depending on how you answer diagnostic questions, you’ll invest in very different hires, work streams and strategies.”

She’s found that the most effective marketer is someone who doesn’t just recite from the pages of a playbook based on a startup’s size or stage. Instead, they can come in and root out the biggest drop-offs and opportunities — and devise unique strategies to act on them.

Muthukumar’s impressive career is proof of her own talent for doing just that. Following product marketing stints at Google and Dropbox, she joined Stripe as the first marketer when the startup had only 60 people. At first, the job was to shore up the high-velocity product team, which was shipping things left and right. She stayed on for nine years as the startup grew to over 7,000 people, helping build out a 100-person marketing org.

She later joined Retool, which had strong product-market fit but needed to spark some more fire at the top of the funnel.

Now she’s heading up marketing at OpenAI — a company that needs no reinforcements on the awareness side, but faces a challenge in educating the public about the technology.

On The Review, Muthukumar unpacks how she’s tackled marketing in all three chapters. She offers up her own game plan for an early marketer’s first month on the job and shares advice for founders looking to bring one on board. She also pulls out lessons on scaling a marketing team from her nine-year tenure at Stripe. Here’s a preview of her wisdom:

• Get prescriptive about how customers should use your product. At OpenAI, the marketing challenge is to help people find a use case epiphany with ChatGPT. “I’m convinced that every company that wants to be effective at marketing their product has to have a really crisp point of view.”
• Borrow creative ideas you admire — as long as they aren’t from competitors. “At Stripe, we borrowed ideas from people who were doing things well, but very much from outside of our domain. We would steal copiously from domains as far ranging as healthcare to people who were launching new programming languages to the security field.”
• Think of internal reviews as brand stewardship. As startups scale, they run the risk of creeping toward bureaucracy with more internal reviews that slow down the work. But Stripe had a different philosophy around the use of a red pen. The marketing org actually relied on reviews to make sure every single project cleared Stripe's high bar for quality. “I don't think we scaled taste at Stripe. Instead, we invested in processes and systems that ensured that everything that went out the door had taste.”

Muthukumar’s insights aren’t just for marketers and founders looking to brush up on the discipline — there’s something in here for anyone curious for a peek into the making of brands like Stripe and OpenAI.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-A follow-up read on scaling marketing orgs

-The importance of naming and framing internal teams

-Shreyas Doshi’s breakdown of the nebulous term “executive presence”

This week, we’re back with another installment in our Paths to PMF series, this time on how Gong CPO and co-founder Eilon Reshef found conviction ahead of a market curve.

Gong’s Path to Product-Market Fit — Why This $7B Company Still Works With Design Partners

A decade ago, product veteran and entrepreneur Eilon Reshef had just sold his first startup to Answers and was itching for something new. He soon met future co-founder Amit Bendov, who pitched him an idea for a tool that records customer calls to give sales teams keep better insights into their deals pipelines. Reshef loved it — and proposed they infuse the product with AI to make it even more helpful.

But this early idea for Gong — which is now a $7B leader in revenue intelligence — was met with heavy skepticism. For context, this was back in 2015, when a bet on AI for business was more of a gamble than the table-stakes play it is now. Investors weren’t sold on it, convinced that CRMs were good enough and worried that a recording tool would ruffle up privacy concerns.

Reshef and Bendov ignored the critics and launched the beta for Gong with a batch of 12 design partners, who didn’t pay at first. These design partners helped the co-founder duo confirm that they were onto something: After only a few months, 11 out of 12 immediately converted into paying customers.

In the latest installment of our Paths to PMF series, Reshef walks us through how he crafted the early prototype and scaled Gong’s suite of products — working with design partners at every step. Here’s a snippet of his tactics:

• Keep the beta lean. Reshef wanted to focus on gauging the value of the tool with design partners, so he resisted investors’ suggestions to add more sophisticated features to the beta.
• Don’t ditch your design partners after you find product-market fit. In Reshef’s view, design partners are valuable sources of feedback for startups at every stage. To this day, Gong’s 20 or so PMs each work with up to a dozen design partners, helping them refine new products and features.
• Build a roadmap that blends founder vision with customer input. “I think the strategic roadmap is maybe 80% ‘vision.’ And then the tactical roadmap is probably 80% customer-led,” says Reshef.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-Notion is hosting its first-ever in-person conference

-A guide from Review favorite Julie Zhuo on managing your manager

-How to be more concise

This week on First Round Review, we’re pulling back the curtain on one of the most opaque parts of the fundraising process.

Here’s What You Can Really Expect When Pitching Your Seed-Stage Startup at a VC Partner Meeting

One of the most admirable traits of founders is the insane amount of courage it takes to leap into the unknown and start something entirely from scratch. Yet when it comes to standing before a room of investors, pitching the idea that you’ve poured your life into can make even the most confident founders sweat.

This anxiety is particularly acute during VC partner meetings, often the final hurdle in a fundraising process. In-depth advice on how to navigate this moment is surprisingly hard to find online. At worst, founders are left to their own devices, flying somewhat by the seat of their pants. But even at best, the playbook for how to handle these meetings is passed down through whispered conversations and one-on-one mentoring sessions. Key details like whose faces you can expect to see around the table, which order to present your slides in, which questions you’ll need to be ready to answer — it all feels like insider baseball.

As a former startup founder herself, First Round Partner Liz Wessel is all too familiar with how daunting these meetings can feel. “I remember having no idea what to expect, and googling as much as I could the night before, trying to understand how best to prepare as a founder,” Wessel says. “I wanted to know what a meeting would entail for a founder like me, whose startup had existed for less than a year.”

Over the course of 8 years, Wessel and her co-founder ended up raising $40 million for their startup, WayUp, which she ran as CEO. After leading the company to an exit in 2021, she joined Y Combinator as a Visiting Partner, where she worked with hundreds of companies, helping many of them prepare for fundraising pitches — including partner meetings for their seed rounds.

Since joining the First Round partnership, she's now on the other side of the table.

“Now, as I bring companies into our partner meetings, I often get calls from founders the night before asking: What should I expect? How can I best prepare? After answering these questions several times over, it dawned on me that it might be valuable to document my answers and share them more widely.”

In an exclusive guest post on the Review, Wessel pulls back the curtain on the VC partner meeting by laying down exactly what founders can expect before, during and after the call. From a detailed breakdown of how PMs differ from 1:1 investor pitches to tips and techniques from founders who pitched their seed rounds just this last year, the advice Wessel lays out is no different than the guidance she tells her own founders.

Here is a taste of how tactical Wessel gets:

• Leverage your point partner. “When I was pitching as a first-time founder, I didn’t realize how 'on your team' the point partner often is. After all, by bringing you in, they’re signaling to the whole partnership that they think you and your company are worth the time and effort of a meeting.”
• Get ready to be interrupted. “It’s not just the clip of questions, but the interruptions that I’ve seen throw founders off the most. So don’t let that happen to you.” One of her favorite techniques to try here is to build surprise interruptions into your practice sessions, by enlisting the trusted help of a spouse or friend.
• Look at the forest and the trees. “The best pitches are ones that can altitude shift, and the best founders can paint a picture of what they’ll be doing in 10 years and then zoom all the way down into the weeds of today and how they’ll get there.”

Wessel's insights provide a rare, candid look into one of the most crucial parts of a founder’s fundraising journey. Whether it’s your first time pitching an institutional firm or you're a repeat founder looking for an edge going into your next meeting, we hope you pick up something new from this guide.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-Remembering the life of Susan Wojcicki

-Annie Duke’s lightning lesson on how great leaders make hard decisions.

-Nikhyl Singhal on the four phases of company growth

-10 time management techniques that actually work

This week on First Round Review, we delve into org design with a three-part framework optimizing for "taste" over symmetry.

Make an Org Chart You Want to Ship — Advice from Linear on How Heirloom Tomatoes Should Inspire Team Design

Tomato season is in full swing, and while you're probably thinking about caprese salads and gazpacho, we're thinking about... org charts. Stay with us here.

“If we think of the org chart as a tomato, weirdly irregular yet delicious heirloom tomatoes are the better product, not perfectly symmetrical — but ultimately bland — spheres," says Nan Yu, Head of Product at Linear.

Yu has developed a strong affinity for these farmers’ market favorites throughout his career. After leading technical and product teams at Everlane and Mode, and advising numerous early to mid-stage startups, he noticed a pattern in team structures, especially in product.

Many companies were following "the Spotify squads" model, an agile design approach from 2012 that groups people into small teams (usually around 5-8 engineers per PM) focused on narrow product slices. But this design doesn’t always work out.

“What founders slowly discovered over time is if you break up your teams into little bits, and ask them each to cover a narrow scope that’s mutually exclusive from the other teams, it’s probably not going to work,” Yu says. “They ran headfirst into Conway’s Law.”

While Conway's Law, connecting organizational communication and system design, may be familiar to founders, Yu contends that startups fail to take action on its crucial insight: You will ship your org chart.

“If you believe that you're going to ship your org chart, then you should make an org chart that you want to ship. The differentiation that every startup has in their product should then be reflected in their teams,” Yu says.

Pulling from his presentation at this year’s Figma’s Config conference, Yu breaks down the three essential components of the “heirloom org chart,” — weaving in examples from Linear’s actual team design to illustrate it in action. Here’s a sneak peek:

• Shape: “When you read management books about org design, they always show you these perfectly balanced charts. Symmetrical tree diagrams and curated grids that fill up to the margins. But creating a pretty-looking chart is not a KPI,” Yu says.
• Size: “If you’re a startup, chances are there are a few things that make your product truly different. These are the areas to over-provision. Leave enough slack on those teams. Not just to build the first version. But to deal with inevitable user feedback, maintenance, bug reports, polish,” he says.
• Scope: “Just because you can point to a component of your product, doesn’t mean you should have a dedicated team for it. Some things are pure table stakes, the kind of stuff you want to do as little as possible,” he says. “The default number of people working on it should round to zero.”

Founders and product leaders are bound to gain a fresh perspective on focus with this seasonally appropriate framework. But there’s one last caveat to keep in mind. “All startups and products look different from each other. So their org charts should look different from each other too,” Yu says.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-Can’t get enough org design? Check out our podcast episode with Square’s Saumil Mehta for a behind-the-scenes look at Square’s latest re-org

-On asking for help (even when you don’t really want to)

-A guide on how to create an effective pricing page

-Molly Graham’s post on normalizing “work grief”

This week on The First Round Review, we’ve rounded up the advice we’ve collected from product leaders on the topic of expanding your product suite.

The Guide to Going Multi-Product: 11 Tactics for Tackling Your Next Bet

Startup leaders know all too well that there isn’t really a steady state in company building. You don’t have much time to stop and admire the view once you’ve hit a big milestone — you immediately start climbing toward the next growth rung.

After finding strong traction with your initial solution, the subsequent goalpost on the path to widening your TAM and compounding revenue is launching a new product. (In our view this is a critical but often overlooked step in truly unlocking what we call "extreme product-market fit.")

But it’s daunting to introduce an entirely new product to your roadmap. Three strategic questions typically pop up when pondering a jump into multi-product:

• When is the right time?
• What should we build next?
• How can we execute this new product organizationally?

Across our digital pages and radio waves, founders and operators have weighed in on these thorny questions in bits and pieces, so we’ve compiled their learnings into one in-depth guide on going multi-product. It’s full of actionable takeaways on what they got right (and wrong) when launching new bets. Here’s a preview of their advice:

• Wait until it feels like you’re pedaling at half speed, says Max Rhodes, CEO and Co-Founder of Faire.
• Data isn’t always a crystal ball, says Tara Seshan, early product lead at Stripe.
• Divvy up resourcing for new bets according to risk, says Noah Desai Weiss, former Slack CPO.

Thanks, as always, for reading and sharing!

-The Review editors

Recommended resources:

-Ben Lang, former Head of Community (and early hire) at Notion, on how to find and join a breakout startup

-Marketing psychology lessons from Rory Sutherland

-How managers can be more explicit about their expectations

This week on The First Round Review, a veteran analytics leader unpacks what she’s learned from a decade of helming the data team at DoorDash — and shares her playbook for startups first standing up the function.

Starting an Analytics Org From Scratch — Lessons From a Decade at DoorDash

Early-stage startup builders likely aren’t spending much time poring over customer data. There probably isn’t much of it anyway — and you’re too busy building an MVP or practicing your fundraising pitch. At this phase, analytics can seem like the far-off domain of huge companies with legions of users.

But as the momentum of product-market fit picks up and more and more users leave measurable fingerprints across your product, you might begin to wonder how to start tracking everything. Is it time to build out an analytics team?

As both a seasoned analytics leader and a startup advisor, Jessica Lachs is a good person to ask. She joined DoorDash as its first General Manager back in 2014, helping the delivery service hit the ground in a couple US cities, and went on to found the analytics team and make the first few hires. Ten years, millions of users and an IPO later, Lachs has climbed the ranks to VP of Analytics, leading a global org of over 300 people — so she’s seen firsthand how the company’s data and resourcing needs have evolved at every stage of its life.

In today’s article, Lachs lays out a comprehensive guide for early-stage startups that are just starting to think about how to tackle analytics. Alongside plenty of examples of how she did things at DoorDash, she breaks down:

• A birds-eye-view of an analytics org
• The three C’s of data: creation, curation and consumption
• Which metrics to track early on — and when to start experimenting
• Hard and soft skills to vet analytics candidates for
• The profiles of Lachs’ first hires
• A checklist to gauge your startup’s readiness for an analytics org

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-Jessica Lachs on how she landed her role at DoorDash with no formal data science training

-First Round's own Meka Asonye will speak on a virtual panel about what makes a winning pitch — sign up here

-A long-time Stripe product lead talks craft and quality on Lenny's Podcast

This week, we’re sharing the latest installment in our Paths to Product Market Fit series, this time with the GTM powertool Clay.

Clay’s Path to Product-Market Fit — A 7-Year “Overnight Success”

Sometimes, getting the right messaging for your startup is more challenging than getting to the right product itself.

Consider this fresh (just shipped today) example from Clay:

We built Clay to help businesses grow. We make tools that help growth marketers and rev-ops teams dramatically improve their customer research – and use that to scale their outreach. Customers can use Clay to query over 75+ data enrichment tools in one credit-based marketplace and aggregate the results, which often triples coverage and accuracy. Then, they can use our AI research agent to replace any manual research task. Finally, once they have a strong data foundation, customers can use our AI message writing feature to help them automatically craft relevant, personalized messages to each prospect.

Today, the company shared it has raised a $46M Series B round to help more GTM teams do just that, as they’ve passed 100K users and nabbed 2500+ customers (including Anthropic, Intercom, Notion, Vanta, and Verkada). But the journey to getting to these impressive milestones and this crisp framing of who they’re for and what they do was a longer one.

Founded in 2017, the Clay team spent six years quietly plugging away before experiencing an explosion of customer and revenue growth in the last 18 months. (To underscore just how meteoric the rise has been, the startup was still close to $0 in revenue as recently as spring 2022.) But if you fast forward over the years of wandering — like many founding startup tales often do — on the surface it seems like a classic "overnight success" story.

The years-long roadblock wasn’t because Clay didn’t have a market to target — it was that they had too many potential ICPs to pursue. Committing to one customer and resisting the urge to horizontally build was a multi-year learning journey. (This example below of how their positioning has evolved is one of our favorite before and afters.)

Co-founder Kareem Amin is one of the most thoughtful builders we know, so we were thrilled to get the chance to dig more deeply into his takeaways from Clay’s path to product-market fit.

“When you're an early startup team, one of your strengths is that you're malleable,” Amin says. ”A prospect can say, 'Oh, could you guys do this?', or 'Are you guys this?' And then you can become that, quite easily. What I’ve learned is that you have to know when to be malleable.”

In the latest installment of our Paths to PMF series, Amin drills into the debate between building a horizontal vs. vertical product. Along the way, he recounts all his lessons learned, from to the “spiral” many early-stage founders face when staring down committing to an initial ICP and the micro-habits he nurtures to remain hyper-focused as a second-time founder.

Founders, product leaders and marketers alike will have plenty to learn from Clay’s meandering journey to find its perfect customer, and from methodical and introspective approach Amin brings to company-building. (If you prefer to listen, check out the audio version of our interview here.)

Thanks, as always, for reading and sharing.

-The Review Editors

Recommended resources:

-Common early-stage fundraising mistakes, and how to avoid them (featuring some advice from First Round’s own Meka Asonye)

-Five simple questions to ask before launching a brand announcement

-Maven founder Gagan Biyani on the three critical decisions that led to massive breakthroughs in growth

This week on First Round Review, we hold three conventional engineering management “anti-patterns” up to the light for a closer look.

Unexpected Anti-Patterns for Engineering Leaders  — Lessons From Stripe, Uber & Carta

When Will Larson was CTO at Calm, he had to make the tough call to cancel a major product migration from the monolith to a multi-product suite. It ended up being a huge success for the company, so when he first got to Carta, also in the CTO’s seat, he had the instinct to try the exact same thing.

“I thought, if it worked at Calm, why wouldn’t it work here?” Larson says.

What he discovered later was that he was missing crucial historical context and different perspectives, things he only found out after getting obsessively close to the details on his team.

While conventional management wisdom told him, as a leader, to step away from the code, it was the dozens of conversations and days spent mining for context that clued him into all the reasons his strategy at Calm never would have worked at Carta.

“One of the biggest lessons in management over the last decade is that micromanagement is bad,” he says. “But I think this is an anti-pattern. Avoiding micromanagement creates disengaged and context-free leadership, and leadership can be so much more than that.”

Larson has always been drawn to the puzzle that is engineering strategy. His winding career has landed him in leadership roles at Stripe, Uber and Digg — and he’s scaled engineering teams from tens to hundreds of people. He’s meticulously documented the lessons he’s learned, penning widely-circulated essays on the topic on his blog, authoring three different books and even sharing some of his frameworks right here on the Review.

He returns today to drop more knowledge, this time focusing on conventional leadership practices that lead folks astray. “We have to have the openness to think through whether a different approach might make sense in a very specific case,” he says. “That’s a fundamental part of engineering.”

In this exclusive interview, Larson walks through three unexpected anti-patterns engineering leaders can use to elevate their team strategy. He lays out the case for why micromanaging can be a good thing, why execs shouldn’t bother spending too much time on metrics, and why managers shouldn’t shield their direct reports from reality.

While he speaks directly to an audience of engineering leaders, his advice goes far beyond that, and executives in any function are sure to find his advice useful.

Here’s a quick snippet of what’s inside:

• Don’t shy away from micromanagement: “New engineering managers are often advised to ‘step away from the code.’ But an extremely high-functioning exec understands the domain they are operating in at some level of detail,” he says. “As you get too far out of the details, you just become a bureaucrat. Too many well-meaning engineering managers end up as bureaucrats.”
• Measure imperfectly: “Often when people start measuring, there's always a concern that their measurement is flawed. And that's true for all functions,” he says. “But I’m a believer in measuring something imperfect, but useful, versus holding out for the perfect metric while measuring nothing in the interim.”
• Don’t be an umbrella: “In the past, I used to think I was energizing my team by sparing them the details. But now it feels like lying to them,” he says. On a tactical level, Larson adjusted this habit by buffering less information. “That means even if it’s disappointing for folks, I’d rather them process news bit by bit, rather than deal with a huge ocean of mess all in one moment.”

Thanks, as always, for reading and sharing!

-The Review Editors

P.S. If you’re hungry for more of Larson’s best leadership practices for eng teams, go deeper by listening to our podcast episode with him here.

Recommended resources:

-Will Larson’s latest blog post on making engineering strategies more readable.

-CTO and career coach Yue Zhao on what we get wrong about influence.

-This deep dive examines the growing specialization of product management.

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This week on First Round Review, we hold three conventional engineering management “anti-patterns” up to the light for a closer look.

Unexpected Anti-Patterns for Engineering Leaders  — Lessons From Stripe, Uber & Carta

When Will Larson was CTO at Calm, he had to make the tough call to cancel a major product migration from the monolith to a multi-product suite. It ended up being a huge success for the company, so when he first got to Carta, also in the CTO’s seat, he had the instinct to try the exact same thing.

“I thought, if it worked at Calm, why wouldn’t it work here?” Larson says.

What he discovered later was that he was missing crucial historical context and different perspectives, things he only found out after getting obsessively close to the details on his team.

While conventional management wisdom told him, as a leader, to step away from the code, it was the dozens of conversations and days spent mining for context that clued him into all the reasons his strategy at Calm never would have worked at Carta.

“One of the biggest lessons in management over the last decade is that micromanagement is bad,” he says. “But I think this is an anti-pattern. Avoiding micromanagement creates disengaged and context-free leadership, and leadership can be so much more than that.”

Larson has always been drawn to the puzzle that is engineering strategy. His winding career has landed him in leadership roles at Stripe, Uber and Digg — and he’s scaled engineering teams from tens to hundreds of people. He’s meticulously documented the lessons he’s learned, penning widely-circulated essays on the topic on his blog, authoring three different books and even sharing some of his frameworks right here on the Review.

He returns today to drop more knowledge, this time focusing on conventional leadership practices that lead folks astray. “We have to have the openness to think through whether a different approach might make sense in a very specific case,” he says. “That’s a fundamental part of engineering.”

In this exclusive interview, Larson walks through three unexpected anti-patterns engineering leaders can use to elevate their team strategy. He lays out the case for why micromanaging can be a good thing, why execs shouldn’t bother spending too much time on metrics, and why managers shouldn’t shield their direct reports from reality.

While he speaks directly to an audience of engineering leaders, his advice goes far beyond that, and executives in any function are sure to find his advice useful.

Here’s a quick snippet of what’s inside:

• Don’t shy away from micromanagement: “New engineering managers are often advised to ‘step away from the code.’ But an extremely high-functioning exec understands the domain they are operating in at some level of detail,” he says. “As you get too far out of the details, you just become a bureaucrat. Too many well-meaning engineering managers end up as bureaucrats.”
• Measure imperfectly: “Often when people start measuring, there's always a concern that their measurement is flawed. And that's true for all functions,” he says. “But I’m a believer in measuring something imperfect, but useful, versus holding out for the perfect metric while measuring nothing in the interim.”
• Don’t be an umbrella: “In the past, I used to think I was energizing my team by sparing them the details. But now it feels like lying to them,” he says. On a tactical level, Larson adjusted this habit by buffering less information. “That means even if it’s disappointing for folks, I’d rather them process news bit by bit, rather than deal with a huge ocean of mess all in one moment.”

Thanks, as always, for reading and sharing!

-The Review Editors

P.S. If you’re hungry for more of Larson’s best leadership practices for eng teams, go deeper by listening to our podcast episode with him here.

Recommended resources:

-Will Larson’s latest blog post on making engineering strategies more readable.

-CTO and career coach Yue Zhao on what we get wrong about influence.

-This deep dive examines the growing specialization of product management.

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This week, we're marking the last day you can apply to PMF Method by sharing an extra dose of encouragement, with 20 lessons from 20 different founders on tackling the winding journey to product-market fit.

20 Lessons From 20 Different Paths to Product-Market Fit — Advice for Founders, From Founders

For more than a year and a half now, we’ve been privileged to showcase dozens of remarkable founders in our Paths to Product-Market Fit series, a wide-ranging public study into how all sorts of different companies have tackled the journey to product-market fit.

Importantly, our goal has been to skip over the glamorous, up-and-to-the-right talking points to find out what really happened behind the scenes.

That’s why we’ve told the real stories of false starts and pivots, like how Plaid started out as a consumer budgeting app, how Lattice was focused on OKRs before shifting to performance management, and how Shippo’s founders were originally building an e-commerce site. We shared vivid and detailed anecdotes, like how Vanta cycled through different company ideas, how furiously coding on a train ride convinced Ironclad to change its category, and how Webflow almost sputtered out after a splashy launch on Hacker News.

But ever hoping to be equal parts inspiring and practical, we’ve also dug into the tactical nuts and bolts — from how Gong excelled at leveraging design partners and how Material Security pressure tested different ideas, to how Retool refined its ICP and Airtable took two slow years to launch its beta.

We thought it was well worth revisiting some of the biggest lessons that have stuck with us — so we plucked out our favorite bits of advice from each story in the series so far.

The advice that follows touches on all sorts of different mile markers along the PMF journey, from coming up with the idea and validating it, to talking to customers, building the initial product, and figuring out your market and messaging.

Our goal is that you can find a dose of inspiration, the antidote to a particularly thorny 0-1 problem you’re facing, or a fresh perspective to reframe your thinking.

Thanks, from all of us at First Round, for reading and sharing.

-The Review Editors

P.S. — We’ve also included several videos of the interviews throughout, in case you prefer to hear your company building advice straight from the founder’s mouth (and plenty of the series’ popular timeline graphics, in case you prefer the continuum format).

P.P.S. — If you’re looking to dive even further into what it takes to find product-market fit, check out our new framework, The 4 Levels of Product-Market Fit. You can also apply to join PMF Method by today, May 7 at 11:59 PDT to get help uncovering what customers really need, building the right V1 product, and closing your first commercial contracts.

Recommended resources:

-Review favorites Tara Seshan and Brie Wolfson have started a new podcast, Red Queen, where they tell the stories of the invention and reinvention of the world's most innovative companies.

-Our very own Annie Duke stopped by another Review favorite podcast to chat all things decision-making with the one and only Lenny.

-What Every’s Dan Shipper learned from spending 24 with Github’s Copilot Workspaces product.

This week, we're marking the last day you can apply to PMF Method by sharing an extra dose of encouragement, with 20 lessons from 20 different founders on tackling the winding journey to product-market fit.

20 Lessons From 20 Different Paths to Product-Market Fit — Advice for Founders, From Founders

For more than a year and a half now, we’ve been privileged to showcase dozens of remarkable founders in our Paths to Product-Market Fit series, a wide-ranging public study into how all sorts of different companies have tackled the journey to product-market fit.

Importantly, our goal has been to skip over the glamorous, up-and-to-the-right talking points to find out what really happened behind the scenes.

That’s why we’ve told the real stories of false starts and pivots, like how Plaid started out as a consumer budgeting app, how Lattice was focused on OKRs before shifting to performance management, and how Shippo’s founders were originally building an e-commerce site. We shared vivid and detailed anecdotes, like how Vanta cycled through different company ideas, how furiously coding on a train ride convinced Ironclad to change its category, and how Webflow almost sputtered out after a splashy launch on Hacker News.

But ever hoping to be equal parts inspiring and practical, we’ve also dug into the tactical nuts and bolts — from how Gong excelled at leveraging design partners and how Material Security pressure tested different ideas, to how Retool refined its ICP and Airtable took two slow years to launch its beta.

We thought it was well worth revisiting some of the biggest lessons that have stuck with us — so we plucked out our favorite bits of advice from each story in the series so far.

The advice that follows touches on all sorts of different mile markers along the PMF journey, from coming up with the idea and validating it, to talking to customers, building the initial product, and figuring out your market and messaging.

Our goal is that you can find a dose of inspiration, the antidote to a particularly thorny 0-1 problem you’re facing, or a fresh perspective to reframe your thinking.

Thanks, from all of us at First Round, for reading and sharing.

-The Review Editors

P.S. — We’ve also included several videos of the interviews throughout, in case you prefer to hear your company building advice straight from the founder’s mouth (and plenty of the series’ popular timeline graphics, in case you prefer the continuum format).

P.P.S. — If you’re looking to dive even further into what it takes to find product-market fit, check out our new framework, The 4 Levels of Product-Market Fit. You can also apply to join PMF Method by today, May 7 at 11:59 PDT to get help uncovering what customers really need, building the right V1 product, and closing your first commercial contracts.

Recommended resources:

-Review favorites Tara Seshan and Brie Wolfson have started a new podcast, Red Queen, where they tell the stories of the invention and reinvention of the world's most innovative companies.

-Our very own Annie Duke stopped by another Review favorite podcast to chat all things decision-making with the one and only Lenny.

-What Every’s Dan Shipper learned from spending 24 with Github’s Copilot Workspaces product.

This week on First Round Review, we sit down with Asana’s Head of People for an inside look at how she built a company culture amidst rapid scale.

Build Your Culture Like a Product — Lessons from Asana’s Head of People

When it comes to company culture, there are two sides to the coin. There are the implicit bits that can’t be framework-ified — they spring forth directly from the traits of the founding team, as well as the folks brought into the fold early on. Eventually, these might be codified into a set of company values or rituals, but in the beginning, they likely exist first as an engine quietly humming beneath the surface.

Then there are the explicit pieces of company culture that are put into place with intentionality and rigor. And that’s where folks like Anna Binder come in.

Binder joined Asana as Head of People back in 2016. The company had around 100 people at the time and had recently raised its Series C — and she was the first HR hire to climb aboard. But just because there wasn’t an official People team on Asana’s org chart, that doesn’t mean that culture was non-existent. Binder’s job wasn’t to spin something up from scratch. Instead, it was to evaluate the culture that already existed, figure out what was working and what could use some tinkering, and put a more robust strategy into place as the company eyed a big leap in growth.

“You have to build your culture like the product,” says Binder.

In our sit down with Binder, she unpacks her guide for doing exactly that. First, she rewinds the clock back eight years to when she first joined Asana, and the specific steps she took early on to develop a comprehensive plan for creating the cultural roadmap. Next, she shares some of her tactical advice for disseminating your values across the org and up and down the ladder, with specific examples of how Asana has tackled this. And finally, she takes us inside the C-Suite, and the rituals the Asana deploys to foster a trusting, high-impact exec team.

Thanks, as always, for reading and sharing!

-The Review editors

Recommended resources:

-First Round Partner Todd Jackson is the guest on Lenny Rachitsky’s podcast this week, unpacking the ins and outs of the PMF Method framework.

-Shreyas Doshi on how the best leaders micro-manage.

-Patrick Collison on beauty and craftsmanship when building products.

-There's no one way to approach PR — 10 perspectives for startups to have

This week on the First Round Review, we’ve pulled together a guide for anyone sitting in the founder’s seat for the first time (or has their eye on taking the entrepreneurial leap).

Navigating New Waters: 10 Tips for First-Time Founder Success

Growing up, we’re constantly trying new things — from taking up a new sport, learning a language, trying out an art class, there’s no shortage of discovery and exploration. But as we enter adulthood, we are much less likely to embrace these opportunities to be a beginner. Sure, folks tout the importance of “The Beginner’s Mindset” — but how often are we truly putting this idea into practice?

Let’s face it, setting your pride aside and jumping into something brand new is just plain uncomfortable. That’s what makes founders such a unique and exceptional group of folks.

When you decide to take the plunge and pursue building an idea from the ground up, you open yourself up to learning all sorts of things for the very first time. But there’s an extra dose (okay, a few extra doses) of pressure compared to taking beginner tennis lessons. There may be investor money on the line. As you get a bit further down the process, there are employees who are counting on you to get it right. Your own professional reputation may feel like it hangs in the balance.

From figuring out how to validate your idea in the first place, trying your hat at sales without being a natural salesman, figuring out the marketing copy for your first pass at a proper website, or even becoming a first-time manager, the amount of “firsts” can truly make your head spin.

To help, we combed the Review archives for some of our favorite bits of advice for first-time founders, from folks who’ve already tread that path. What follows is tactical guidance from a seasoned group of folks, including Dropbox’s Drew Houston, Thumbtack’s Marco Zappacosta, Vanta’s Christina Cacioppo, and NerdWallet’s Tim Chen. Each shares the lessons they learned the hard way on everything from keeping your ego in check to hiring the early team and tackling competition.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-This read on delegation, aka "hand off your monkeys"

-How to become a more technical PM

-Molly Graham on growing your career in every role

How to Know if Your Idea’s the Right One — A Founder’s Guide for Successful Early-Stage Customer Discovery

How do you go from a pie-in-the-sky idea to a fully-fledged product? Some founders start building right away, spinning up a (slightly shoddy) MVP for folks to react to, then iterating from there. Others take a deep-diving approach to research, setting up dozens (or even hundreds) of calls with folks to validate the idea before writing a line of code.

As a user research expert, you might expect Jeanette Mellinger to be in favor of the latter approach — but you’d be wrong.

Sure, she’s a big proponent of user research interviews as a form of validating your idea. But this slapdash mentality of trying to speak to as many folks as possible is where she finds that many well-meaning founders go astray.

In addition to her role as BetterUp’s Head of UXR, Mellinger also works closely with early-stage startup founders as First Round’s User Research Expert in Residence. To these folks, she preaches the mentality that less is more. You can glean more qualitative data points and patterns from five deep conversations than from 50 unfocused ones.

“We get nervous when we hear, ‘Oh gosh, I only spoke with five people.’ But that’s my user research magic number. If you bring that focus into it, you can get something that’s much deeper than you’d ever expect,” she says.

On the Review, we unpack her ultra-approachable three-step guide to bring more structure to early customer discovery and idea validation. Along the way, she shares plenty of low-lift tactics to ensure your approach is rigorous, but not onerous.

• Step 1: Make a Plan. “It’s so tempting to want to ask about 10 things at once, but that’s only going to yield shallow, inch-deep responses. This is your opportunity to go deep. What are the one or two things you must learn now?”
• Step 2: Learn without letting bias creep in. “Let’s say you start to hear something that sounds really good. That’s your alarm right there. The moment you hear, ‘Oh yeah, this product is great,’ that’s a sign to ask the counter. What is something you can push on here?”
• Step 3: Find the right patterns. “So often teams will want to jump right into solutioning and action mode. But the more you ground yourself in the data, the more conviction you’ll have in your idea.”

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

-We’re looking for a go-to-market manager in SF or NYC to help founders get their first million in revenue, faster.

-Want to know how your go-to-market motion stacks up to the best? The 2023 Product-Led Sales Benchmark Report is out now!

-Shreyas Doshi is hosting a product leadership masterclass seminar on March 23rd.

-This video with books every entrepreneur should read.

-How to escalate a problem the right way.

Trending this week — Review Reads:

GOAT’s Path to Product-Market Fit — How a Fake Sneaker Sparked a $4B Idea

GOAT co-founder and CEO Eddy Lu sits down with First Round Partner Todd Jackson to tell the story of how a decade of middling entrepreneurial ideas finally culminated in the $4B idea for a sneaker marketplace.

First Round ReviewFirst Round Staff

From Flagship Back to Fledgling: Lessons on Going Multi-Product From an Early Stripe PM

In this exclusive interview, Tara Seshan shares nine lessons from her playbooks for going multi-product, drawing on examples from both Stripe and Watershed.

First Round ReviewFirst Round Staff

‘Get in the Van’ and Other Tips for Getting Meaningful Customer Feedback

Michael Sippey has been building tech products for over 20 years. His most valuable ideas, though? They came from speaking with customers. Here’s how.

First Round ReviewFirst Round Staff

The Tactical Guide to Making Better Decisions When Starting and Scaling Companies

The First Round team has been lucky to work with retired poker player and decision-making expert Annie Duke in a special capacity these past few years. Here, we open-source some of the advice she gives to help founders face down uncertainty and make better decisions.

First Round ReviewFirst Round Staff

GOAT’s Path to Product-Market Fit — How a Fake Sneaker Sparked a $4B Idea

We’ve covered lots of different founder paths here on the Review. But none may be as curious and meandering as Eddy Lu’s.

Today, he’s the co-founder and CEO of GOAT, a global platform for sneakers and luxury apparel that boasts over 350 brands, a million sellers, and 50 million members across 170 countries — valued at over $4B.

But page the calendar back, and you’ll find a decade’s worth of entrepreneurial endeavors with very little in common. After teaming up with his co-founder, Daishin Sugano, the two tried their hand at owning a cream puffs franchise, hopping aboard the early iPhone app train, and even had a YC stint trying to build a community platform for social dining.

Then, a twist of fate (coming in the form of a pair of fraudulent sneakers) sent the pair down an entirely new rabbit hole.

In the latest installment of our Paths to Product-Market Fit series, Lu shares the inside story of all the unexpected twists and turns in GOAT’s founding story — and it certainly wasn’t smooth sailing once the founders landed on their winning idea. Black Friday deals gone awry, website crashes and unpopular features are just a few of the obstacles that would come to pass.

Along the way, Lu shares his biggest pieces of PMF advice for others to lean on — and how to stay gritty and hungry amidst mounting pressure.

Thanks, as always, for reading and sharing!

-The Review Editors

Recommended resources:

High signal-to-noise interview questions.

Stripe’s former COO Claire Hughes Johnson is on the Tim Ferris Show.

Molly Graham on evaluating job fit.

Trending this week — Review Reads

From Flagship Back to Fledgling: Lessons on Going Multi-Product From an Early Stripe PM

In this exclusive interview, Tara Seshan shares nine lessons from her playbooks for going multi-product, drawing on examples from both Stripe and Watershed.

First Round ReviewFirst Round Staff

Add More Rigor to Your Reference Calls With These 25 Questions

When approached with craft and care, reference calls can be a massively influential piece of the hiring decision.

First Round ReviewFirst Round Staff

A Founder’s Guide to Assessing Strengths and Weaknesses

Psychologist and co-founder of Coa, Dr. Emily Anhalt, unpacks the five traits of high-impact founders — and how the very traits that make a founder successful can also hold them back.

First Round ReviewFirst Round Staff

Grit or Quit? Tactical Advice for Founders Facing Tough Decisions

Quitting is an underrated startup skill, says decision science expert, bestselling author, and former poker pro Annie Duke. She unpacks the psychology behind why it’s so hard to walk away, sharing tactical advice for all the forks in the road.

First Round ReviewFirst Round Staff

This week, we're diving into the how, what, when, and why of going from single product focus to multi-product strategy, a common stumbling block for startups.

🎧 Prefer to listen? Check out the audio version of today's interview here. 

From Flagship Back to Fledgling: Lessons on Going Multi-Product from an Early Stripe PM

Who is your target user?

For Tara Seshan, this is the lead-off question for her teams when she’s running product reviews, and it always makes her think of Enterprise — the car rental company.

“I’m not sure if it’s apocryphal or a real story, but I still like to tell it. Enterprise was competing with the likes of Hertz and Avis. Those guys had the airport real estate. They also had Audis and BMWs. Enterprise Rent-A-Car really had nothing. And so there was absolutely no way to compete building ‘the best service’ or ‘best product.’ What they did instead was focus on a different user — people who get into car accidents,” she says. So instead of focusing on providing fancy vehicles, Enterprise offered a unique crash pickup service.

Over time, they were able to expand. But it started by making a very, very opinionated bet on who their target user was and it allowed them to compete on dimensions that other services and tools just didn’t find relevant. It is the most important question to ask, full stop. If you cannot clearly outline to me who your target user is and, therefore, why the features follow are uniquely suited to that user, it’s dead in the water. It's got to be specific.”

In Seshan’s view, folks tend to overestimate the impact of launching specific features and building the best product, instead of focusing on building the right product for their target user. Sounds simple in theory, but tough to consistently pull off in practice, particularly as a scaling startup takes bold swings at building out its product lineup.

But she’s got an excellent track record here. Before her most recent role as Head of Product at Watershed, Seshan spent a nearly seven-year stretch at Stripe. She joined the company at the sub-200-person mark back in 2015. She was the PM on Radar, Stripe's first monetized product outside of core payments, and she helped scale Billing and Treasury from 0 to 1 as a product lead and GM.

Today on The Review, Seshan shares 9 specific lessons on going multi-product and building for your target users, drawing on examples from both Stripe and Watershed. She dives into:

• Advice on how to get the timing right and different ways to approach the problem of what to build
• The 12 questions she runs her teams through at every product review
• How to structure lean, self-sufficient teams that can navigate the uncertainties of new product development
• Tips for hiring great product thinkers and “diamonds in the rough,” including traits to look for and specific interview questions.
• What she learned from Patrick Collison and Shreyas Doshi at Stripe.

Thanks, as always, for reading and sharing!

-The Review Editors

Trending this week — Review Reads:

Add More Rigor to Your Reference Calls With These 25 Questions

When approached with craft and care, reference calls can be a massively influential piece of the hiring decision.

First Round ReviewFirst Round Staff

Vercel’s Path to Product-Market Fit — From Open-Source Project to Billion-Dollar Business

Guillermo Rauch, raised in Buenos Aires and fascinated by computers since age 7, taught himself to code and moved to San Francisco at 18. His company, Vercel — the frontend cloud service behind open-source development framework Next.js — was recently valued at $2.5 billion.

First Round ReviewFirst Round Staff

How to take bigger, bolder product bets

Seasoned product leader and Slack’s CPO Noah Desai Weiss shares the three-step framework he leans on to make quality product decisions with just the right amount of risk.

First Round ReviewFirst Round Staff

Build Products That Solve Real Problems With This Lightweight JTBD Framework

Drawing on her experiences building products at Lumosity, Oculus, and Facebook’s New Product Experimentation group, Sunita Mohanty shares a lightweight “jobs-to-be-done” framework for early-stage product teams, along with templates and go-to-market tactics.

First Round ReviewFirst Round Staff