Brett Berson
@brettberson • 11,968 subscribers
An aspiring learn it all. I’ve been trying to make @firstround a little better every day for 18 years. Partner to @stedi, @Persona_IDV and @clay
Videos
Christopher Payne was President of DoorDash during the stretch that defined the company: hypergrowth, a pandemic, an IPO, and much that came after. He's done very few long-form interviews. This conversation is a rare exception. We explored what excellence looks like in this role. New episode of Executive Function.
Brett Berson449,664 views • 3 months ago
Supabase now has more than 7 million developers building on it. It all started with a tagline change. Paul Copplestone - e/postgres changed Supabase's tagline to "Open-source Firebase alternative." Someone posted it to Hacker News the next day. It shot to the top. He hadn't shipped a single new feature. The product was identical to the days before. His takeaway: "Product-market fit is often just product-positioning fit. Before you pivot the product, try pivoting the words. My full conversation with Paul on his path to product market fit.
Brett Berson33,946 views • 1 month ago
At hypergrowth companies like Vercel, Harvey, and Cognition, executives face a brutal challenge: keeping pace with a company that might grow 5-10x in a year. That means hiring aggressively without lowering the bar, figuring out how to mature the org without slowing down, operating at different altitudes, solving novel problems, and much more. Their role changes quarter to quarter, and the margin for error is razor thin. I'm really excited to launch our newest podcast, Executive Function, which explores a simple question: what is the difference between a good and truly great scaleup executive? We learn what these exceptional execs are doing differently, how they approach their work, how they make decisions, and how they make a difference for their companies. The first episode drops later this week. Learn more at:
Brett Berson77,226 views • 5 months ago
Katie Burke spent 11 years at HubSpot, joining when it was a small private company and ending that chapter as the Chief People Officer of a public company. She then joined @Harvey and is now their COO. We got together to talk about human stuff in the world of AI.
Brett Berson40,250 views • 3 months ago
“Welcome to Stedi. Everything is your fault now.” That's the phrase Zack Kanter greets new hires with when they join Stedi. This embodies his approach to building, which is rooted in his experience scaling and selling an extremely profitable auto parts business. Stedi is the only programmable healthcare clearing house — and it took Zack four years to launch after throwing away every single line of code eight times. This episode was a special one for me because Zack’s a close friend and someone I’ve learned a lot from over the years. We cover a lot in this conversation: - Why bootstrapping is overrated - How he’s building a business he wants to run forever - What software can learn from manufacturing and discount retail And much more: (01:24) Zack’s first business (08:54) Why the first customer is tricky (10:12) The downside of bootstrapping (11:42) Why venture capital is like “going pro” (14:20) The confusion between ownership vs. control (16:08) Building a company you don’t want to leave (20:46) Do things better than other people (24:49) Stedi’s early years (31:43) Physical vs. digital product-market fit (34:41) How Stedi scaled decision-making (40:08) Stedi’s journey to product-market fit (45:22) Finding founder-approach fit (50:42) “All software is a cascade of miracles” (52:52) The surprising lessons from discount retail (57:50) How the Toyota production system influences software (1:01:31) What it means to be a high-agency person (1:03:09) The core trait Zack looks for when hiring (1:02:57) Maintaining conviction in unconventional practice (1:14:19) When should you start to hire managers? (1:17:42) “Reality has a surprising amount of detail”
Brett Berson77,690 views • 8 months ago
Zipline has always done things the “wrong” way. They launched a drone company when drones were essentially illegal in the US. They moved the whole team to trailers on a farm in Half Moon Bay to figure out how to fly. Their launcher was deep sea fishing poles from Walmart. Their landing pads were made by a bouncy castle company. They went to Rwanda with no aviation experience, no logistics experience, no healthcare experience. Co-founder and CEO Keller Cliffton wore tennis shoes and a hoodie to meet the president of the country. The night before the launch, he was on his back in the dirt with a screwdriver in his mouth, trying to rebuild a launcher that kept destroying itself, while the president's special forces watched. The aircraft flew. Keller was just as surprised as everyone else. Nine months of all-nighters after that Rwanda launch, they got one hospital working reliably. Then 20 more in three months. Then 50. Then 400. Today Zipline serves 5,000 hospitals globally and has flown 135 million autonomous miles. To find the best hardware builders in the world, Zipline often hires teenagers. Not as interns fetching coffee — as engineers who own real work. One kid joined at 15 and got offered $180K to lead a team of mechanical engineers instead of going to Stanford. He took it. Another applicant had built a full GPS system for a 3D-printed quadcopter using onboard Nvidia GPUs. While at boarding school. Keller's question for candidates: what have you built? Keller summarized everything in one line: "We specialize in turning the impossible into the merely late." He shares Zipline’s wild origin story in full in our conversation on In Depth. Timestamps: 02:11 Why Zipline doesn't hire for experience 06:04 Are founders born or made? 07:37 Why Zipline hires 17-year-olds over PhDs 17:03 The employees Zipline doesn't want 18:53 The ultimate startup hire is a "heat-seeking missile" 20:36 Why blind references are a non-negotiable 23:07 Can candidates admit when they screwed up? 30:10 Zipline's secret leadership playbook 35:16 Why you should always fire quickly 36:26 The early vision for Zipline 39:48 How Zipline almost died - twice 44:55 From toy robots to drone delivery: Zipline's pivot 51:35 How Rwanda's health minister changed everything 57:10 Why Zipline's launch was a "complete disaster" 1:04:05 Scaling from 1 hospital to 5000 1:05:17 The 10x hardware cost rule every founder should know
Brett Berson42,859 views • 4 months ago
After starting a bootstrapped business to help restaurants drive dine-in customers, March 2020 would bring all of that progress to a halt. And Owner founder Adam Guild would need to act fast to save the company. This is the incredibly detailed story of a pandemic pivot.
Brett Berson113,191 views • 1 year ago
This is Episode 2 of Executive Function with Ryan Lucas, VP of Design at Rippling and former Head of Design at Retool. For Ryan, everything begins with being very clear about what the job of design and a design function really is. In his words, “Useful, usable and desirable are the three things we need to deliver. And I think people often forget about the last bit, but it’s incredibly important to the practice of professional design, whether it’s physical products or software products. Henry Dreyfuss said the designer’s job is not done if the product doesn’t sell, and I’ve always believed that.” We go on to discuss: - Design leaders who "shield" their teams from organizational chaos are doing them a disservice, not a favor. - To truly scale quality, you probably need a benevolent dictator, one opinionated person who sets the bar. - Parker Conrad goes directly to the individual designer when he sees a problem, skipping Ryan entirely, and Ryan thinks that's great. - At Rippling, individual designers sometimes own a Series C company's worth of product by themselves. - Great creative work cannot come from fear because fight-or-flight shuts down the prefrontal cortex, which is where all creative thinking lives. - In the absence of a date, there is no commitment, and that rigor around commitments is what makes Rippling's speed possible. - One-on-ones should be jam sessions on hard problems, not status updates or career development chats. - He'd rather a young designer have opinions he completely disagrees with than no opinions at all. - The hardest skill in the job is knowing which balls are rubber and which are glass, and you only learn by letting some drop. - The most successful use of a design crit is when designers tell you upfront what feedback they actually need, otherwise everyone wastes time on things that have already been decided. - The perfectionism that makes someone a great designer is the same trait that will prevent them from becoming a great design leader. - The best designers steer the business, they see a problem, come out of their lane, and move the tiller without being asked. Timestamps: 03:29 The Useful, usable, desirable — and used — design framework 04:49 How design relates to engineering, product, and marketing 08:15 Measuring success as a design leader 12:40 The gap between director and VP-level design leadership 14:23 Why great design leaders jump up and down in altitude 19:26 The four pillars every design manager must master 21:34 Over-indexing on quality and the perfectionist trap 27:53 How to build judgment through pattern matching 34:31 Why Figma is not the source of truth 38:39 The "Do/Try/Consider" framework 44:05 Should one-on-ones exist? 46:45 How to scale judgment 50:49 What to look for when hiring your first design leader 54:54 Advice for young designers who want to lead 58:24 Demanding yet supportive: A balanced management style 01:02:43 What Rippling's operating system teaches about execution
Brett Berson31,880 views • 5 months ago
Confluent just sold for $11 billion. Jay Kreps built it by learning a distinction that sits at the center of every hard company decision. There are two questions you can ask about anything hard: what can we do? And what do we have to do? The first is answered by your team. The second is imposed by the world. When Confluent needed a cloud product, most of the company thought it was a terrible idea. The on-prem business was working. The economics were better. Investors thought they were making a mistake. As Jay put it: if there were two standalone companies, we'd invest in this one and definitely not that one. Jay's answer: we have to do this. There's no question that a huge portion of the market is going to be in the cloud. So we have to serve that part of the market. The fact that it's very hard is not relevant. Once you know you have to do something, you find a way to do it. We cover this insight amongst dozens of others in my most recent "In Depth" conversation. Timestamps: 01:18 Making the leap from engineer to CEO 03:33 The 80% rule: what a CEO actually needs to know 04:54 Scaling different business disciplines 09:31 How Confluent’s story began in LinkedIn 12:13 The growing need for scalable data tech 13:37 What the early Kafka product looked like 16:38 Kafka’s underwhelming open-source launch 18:38 The blog post that accelerated Kafka’s adoption 20:16 Why so many marketing messages fail 28:08 The decision to build Confluent 34:24 Planning to fundraise before building the product 39:19 Confluent’s early years: Tough product decisions 47:07 The underrated growth lever question for companies 55:46 Why founder optimism is an overrated trait 1:00:29 What should founders give up as they scale? 1:02:47 Why people become trapped in a failure mindset 1:08:33 The Chipotle problem: Losing excellence at scale
Brett Berson19,608 views • 4 months ago
We first began our partnership with Zack Kanter and Stedi back in 2017. Today, they announced their $50 million Series C. But most of those years were spent quietly and quite obsessively building the underlying infrastructure. Once the company built its way into healthcare, things started to inflect quickly. (They were recently named one of Ramp’s fastest-growing vendors across all categories, not just healthcare). But as with most “overnight success” stories, it was nearly a decade in the making. The ambition to replace legacy clearinghouses with a modern API-first, software-native platform is a big one, and the breadth of the product surface is stunning. But it’s Zack’s desire to keep grinding towards bigger outcomes that’s truly outlier. He’s built Stedi with unusual levels of patience and persistence. (For example, they threw away the entire codebase 8 times, and took 4+ years to launch anything publicly.) These choices stem from a determination to avoid what he calls the accumulation of not doing things the right way. His philosophy is rather unique and is best captured in this quote: “As a company, we’ve decided we’re gonna eat glass. That is what sets us apart. We’ll go to the ends of the earth to do things the right way, even when it’s not economical and it doesn’t make sense.” He gets at more of this idea in the clip below from our recent interview, where he talks about why he’s building Stedi to be a company he wants to run forever. He’s an incredibly tough founder to bet against, and I feel fortunate to both be an early supporter of his First Round and to call him a close friend.
Brett Berson19,594 views • 4 months ago
This was one of my favorite interviews of 2025... Founders often underestimate how much freedom they actually have. Anil Varanasi and Meter is a reminder of what happens when you use all of it. They ignored the usual advice and built the company their way. It’s no surprise their story doesn’t resemble anyone else’s. Here are just a few examples: 1. They spent four and a half years pre–revenue, just two people. It was essentially Anil and Sunil, alone, for four and a half years before they had a sales ready product and their first customers. They even scrapped an entire year of operating system work once they realized a different technical approach (inspired by an open source project) was better. 2. They literally moved to Shenzhen to learn how the physical world is made. They were blocked by slow hardware iteration in San Francisco, so they just relocated to Shenzhen for over a year. 3. Full vertical integration as a day one decision, not an afterthought. Meter decided from the start to own the entire stack: hardware, software, installation, and ongoing service. This is in a market where most entrants pick one slice (just switches, just access points, etc.) and get trapped as point solutions that end up acquired. 4. Business model treated as part of the product, not a pricing afterthought. They moved networking from “buy hardware” to: Meter provides the hardware, the software, the installation and ongoing support. The customer pays recurring, per square foot, and effectively “don’t pay us if the network doesn’t work.” Anil thinks about business model innovation on the same level as product and technology innovation. 5. Choosing a massive, incumbent dominated market on purpose. Networking is controlled by a few giants like Cisco. They were pulled toward that exact dynamic: a huge, durable market where the initial ramp is brutal, but if you get through it, there are very few new players alongside you. 6. Deliberately avoided the channel in a channel dominated industry. Roughly 90 percent of networking is sold through the channel.Meter refused to use the channel until they were convinced the product was dramatically better in every way, because incumbents could weaponize the channel with discounts to block them. Only after they had hundreds of happy customers and strong tools did they fully embrace channel sales. 7. The team has an extreme time horizon, paired with extreme urgency. Anil thinks in decades: “I care about where Meter ends up in 25 years, not five.” At the same time, he is obsessively focused on what happens in the next few hours and where every report spends time. That “barbell” between multi decade vision and hour by hour intensity is very explicit for him. 8. An allergy to “meta work” and most conventional management. No OKRs or goals at all. They have a strong skepticism of spending time on docs, processes, and coordination that feel like work but do not move the product forward.
Brett Berson27,497 views • 7 months ago
Today Lattice is synonymous with performance reviews and people management. But not many know that in the very early days, Jack Altman and @ekosz1 had a different product entirely — an OKR tool trying to solve the painful quarterly planning process. As we were developing First Round's PMF Method, we learned so much from Lattice’s pivot — grateful Jack took the time to share his lessons for other builders. 🙏 Here are a few takeaways that have stuck with me: Market pull can be confusing in the early days. Much of PMF advice contains some variation of a “you’ll know it when you see it” type of definition. But for Jack, there’s a key nuance here. “If you haven’t seen early market pull yourself before, you can get easily confused about what it looks like. People are telling you this looks cool, they're saying that they're excited about what's coming, so you think, ‘Okay, maybe we are onto something,’ and that can bleed on that path for quite a long time.” In retrospect, Jack points to 2 signs the OKR tool idea wasn’t working: 1) It was hard to get people to actually pull out their credit cards. “A lot of CEOs and people leaders said, ‘We'd really like this. Can we try it? Can we test it for a quarter? Can we do a monthly thing? Can you give me a login so I can poke around?’ But when we tried to get them to pay, it was very challenging.” 2) Even when people got into the product and did a full OKR planning cycle in Lattice, the next quarter didn't come easily. “They were like, ‘Ugh, we’ve got to do this.’ And then by the third quarter they were like, ‘This is not happening naturally.’ For the employees, the retention was just not there. So both sides were not strong enough.” After Lattice’s pivot (where they kept their HR buyer but changed the product), the difference in traction immediately felt clear. “We had people paying us annual upfront contracts without ever seeing a product, just on our design mocks — which couldn't be more different than the experience we’d been having with OKRs. There were leads coming organically from all over the place. I think we booked twice as much revenue in the first month on that product than we had booked in the previous year on the last one.” If you’re stuck, it takes big swings, not small changes. “A lot of people hang out in nascent PMF and make small changes for years, and that's just a literal waste of everybody's time and resources. Moving up levels of product-market fit or getting unstuck requires more than just incremental steps or giving it more time. More often than not, if you're working on something that is not getting great traction, you’re probably not a 10% adjustment away — you’re probably a 200% adjustment away.” The only people who have the answers are the buyers. “You should really be spending all of your time talking to customers. And that sounds so obvious. But people will find so many reasons to not do that. You’ll hear ‘I really should be recruiting,’ or ‘Some VC wanted to have coffee with me, maybe I'll learn from them about this market.’ And it's all a waste of time. The buyers are where the truth is. When you get to the point where you’ve talked to so many customers that you're sick of hearing the same thing over and over again, that's when you know, you've talked to enough. One of the things that always really helped me is I would remind people that it really doesn't help me if you're nice to me in this meeting. I'm trying to build a company that doesn't fail. And I can only do that if I get genuine responses from you.”
Brett Berson48,044 views • 2 years ago
After doing a lot of customer interviews asking the standard “What's your biggest pain point?” question and not getting anything interesting, Jake Stauch started asking: “If you could hire somebody today to just sit next to you and do work for you, what would you have them do?” That led him to take on ticketing and automating the repetitive work of enterprise IT, an area he was well-suited to tackle with Serval after years of 0-1 product building at Verkada. Since we first got to know Jake back when he was at Verkada and then had the chance to be his Day 1 partners with Serval, this was a unique conversation where we were really able to compare and contrast the two companies, and drill into the lessons he carried over with him.
Brett Berson13,579 views • 9 months ago
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