David Tisch

My conversation with Zach Reitano (@ZReitano), co-founder and CEO of Ro In four years he took Ro from a $250M run rate to over $3B, with about a third fewer people Zach rarely does long conversations like this, so it was fun to talk about the details of what that took and everything happening in healthcare Plus, his answer to the closing question is amazing We discuss: - the state of the US healthcare system - refounding Ro - strong attract, strong repel culture - the notion of jobs over lives - the power of celebrities in marketing - the importance of tailwinds (AI, GLP-1s) - trying to recreate his dad in software Enjoy! TIMESTAMPS 0:34 How Much Should We Spend on Health 4:59 The Patient Is Not the Customer 10:24 Inside Ro's Business 18:28 The Future of GLP-1s 25:46 Jobs Over Lives 30:02 The Turnaround 47:43 Where Healthcare Goes Next 1:00:27 Recreating His Dad in Software 1:06:33 Marketing Into Stigma 1:19:06 Zach's Hottest Take 1:20:58 The Kindest Thing

How does a corporate card startup become a $60B AI product factory? In our first on-camera interview a decade in the making, Ramp co-CEO Eric Glyman (@eglyman) answers just that question. Today, @tryramp is best known for its corporate cards, or maybe its marketing stunts with the likes of Kevin from ‘The Office,’ Tony Hawk and a 70-minute Broadway musical about paying bills. But Eric says his $60B startup, NYC's most valuable, feels less like a fintech and more like a productivity company driven by one simple question: If a business spends $100 to make $200, how can Ramp improve that ratio? Nearly 100,000 companies use Ramp today for everything from expenses to managing AI spend. But Eric says that when he zooms out to the millions who still aren't customers, Ramp feels painfully early still. On The Upstarts Podcast, Eric shares why he’d rather run Ramp like Amazon than Google; why Ramp hires for proof of work, not credentials, from a 14-year-old intern to a 28-year-old CTO; and how being the first customer for Anthropic’s Claude Code and Cognition’s Devin led Ramp to build its own AI tools. Plus: The real story of Paribus, his first startup with co-founder Karim Atiyeh (@karimatiyeh); what they learned at Capital One; and a warning for Instinct and Muse. This season is presented by @Atlassian and @chargebee 🫡 CHAPTERS 00:00 Introduction 01:51 What Ramp Actually Does 03:27 From Gym Charges To 1% Of U.S. Corporate Payments 05:13 Glass, Inspect And Building AI Tools For Itself 07:45 An AI Sales Assistant Before ChatGPT 09:45 How Ramp Decides What Products To Ship 11:14 First Customer For Claude Code And Cognition’s Devin 13:09 Why Ramp Wanted To Build Like Amazon, Not Google 15:42 Hiring For Proof Of Work: The 14-Year-Old Intern 18:43 A .300 Batting Average And ‘Growth Without Fear’ 21:17 What Ramp’s Founders Learned At Capital One 24:00 The $1,000 Flight Refund Behind Paribus 26:34 Bots, A Cease-And-Desist, And A Lesson For Instinct And Muse 32:00 Marketing 101: Bill Pay The Musical And Kevin In A Glass Cube 36:01 Business Books And Helping People Do Their Life’s Work 39:03 How A 28-Year-Old CTO Catalyzed A Co-CEO Change 43:55 ‘Still So Early’: How Ramp’s Founders Stay Hungry 55:26 John Wooden And Why Ramp Competes Against Itself Thanks for watching!

David and the BoxGroup team are great. Don't sleep on them.

I will remember the VCs that put us in tranched rounds. “If I view it as not the founder that tranched us but the other VC, it is good to know. I also have a long memory. You have decided that I will pay another price. You have created the structure of this deal such that I am not sitting on the cap table with you. I am pushed to a different product than you get to invest in. When we have early-stage investments and are going out to market to help them raise capital, if I get to be a voice in the ear of a founder, I have opinions too.” @davidtisch Love to hear your thoughts @BennettSiegel @steph_palazzolo @danprimack @mashadrokova

Excellent conversation.

One of the single most important things that I look for in anyone is the ability to admit that they were wrong. Reflect on it and improve. I admit that I was wrong in previous discussions with @davidtisch at @BoxGroup. I did not think that you could produce outsized returns from hugely diversified portfolios (150+ companies) with still quite large fund sizes ($200M+). I was wrong. With Cursor, Baseten, Clay, and many more incredible companies in his portfolio, he has proved his thesis without shadow of doubt. This was an incredible discussion analyzing Box's returns over the years. (Link in comments) -- 1. I Don't Want to Compete With the Best VCs, That Is a Trap Owning 10% to 20% of a true outlier in the seed round means beating the rest of the market head-to-head and convincing the founder to pick you. That takes too many steps to believe, so do not compete directly against the best VCs in the world. I would love to hear how you think about your position as a "lead" seed investor and if that has changed with the expansion of rounds @dafrankel @Bandrew @chadbyers? 2. What Concentrated Funds Know but Do Not Admit To Concentrated managers claim they win 90% of the deals they want, but David puts the real figure at around 20%. A fund backing 30 high-conviction companies at 10% ownership likely offers that deal to 120 to 150 companies to land its 30. He calls this adverse selection that people do not admit to. 3. Why the Lean Startup Was a Total Fake The Lean Startup is a brainwash that ran for 10 years through professors, books, tweets and blog posts. It sent people the wrong message. Do you think this is fair and is capital a moat today unlike in prior cycles @rabois @alanchanguk 4. The Marketing Message That Pro Rata Is Not a Right Is BS Early-stage VCs saying they do not need pro rata is marketing garbage. The right to invest in subsequent rounds is earned, whether or not it is in the documents, and having it written down helps the founder more than the firm. A firm that refuses a founder's request to step back is getting into a fight it will likely lose. How do you think about this @apartovi @honam 5. We Do Not Allow Negativity in the Investment Decision-Making Process Partners who have not spent time with the founders are not allowed to be negative about a deal. With 70% to 90% of early-stage companies failing, explaining why one will not work is "incredibly obvious and incredibly irrelevant." The job is to say yes to the right things without fear of the ones that fail. What is the single best advice to optimise investment decision making discussions @shaunmmaguire @AnnieDuke? 6. Why We Have Less Dilution Now Than Ever Before In companies that scale quickly, Series B, C and D rounds are now raised at 3% to 8% dilution instead of 12% to 20%. Across multiple rounds, early-stage investments get diluted less, this is a real economic factor for early investors. Love to hear your thoughts on this @jasonlk... 7. Why Funding Consumer Brands at Seed No Longer Makes Sense for Venture BoxGroup has stopped funding brands because the data that proves a brand works, such as whether people buy it and whether CAC to LTV ratios make sense, does not exist at seed. Brand investing at Series A is an interesting product for a subset of investors, but not one that fits traditional venture firms today. How has your thinking on this changed over the years @eurie_kim @kirstenagreen @fcourt?

When I shut down my first startup and returned the money to investors, some of them never spoke to us again. @davidtisch was the opposite. He was a human heat shield with many of those investors, and he backed me personally and professionally right after. When we started Ro, @BoxGroup was our first call. Tisch and the BG family will always have a special place in my heart. They march to their own drum. They build differently. And after years of being misunderstood, game is finally recognizing game. About time :)

After finishing the interview it is really refreshing how much @davidtisch gets it. Proud to work with @BoxGroup

So special to do this and I was wrong! 😆 David you were right and I was wrong!!!

Today @dolapo and I are introducing Scuba, the shared context engine for teams and their agents. Never lose a great idea. Capture anything, share what matters, and keep your people and agents aligned as you move faster together. Everyone is moving faster on their own with AI. But so few teams feel they’re moving smarter together. The models aren't intelligence bound anymore. They're context constrained. Scuba is the shared memory your team has been missing. Put it to work in Slack, Claude, ChatGPT, Cursor, and any tool that supports MCP. We run our whole company on it, with under two hours of meetings a week. We’re emerging out of stealth with $34M. We’re grateful to @accel for leading our pre-seed and co-leading our seed with @ivp, alongside @BoxGroup, @conviction, @homebrew, and @ScribbleVC. Our angels include the founders of Slack (@stewart @iamcal), Instagram (@mikeyk), Stripe (@patrickc), LinkedIn (@reidhoffman & Jeff Weiner), Salesforce (@parkerharris), Datadog (@oliveur), Vanta (@christinacaci), Harvey (@winstonweinberg), Dropbox (@drewhouston), Abridge (@ShivdevRao), Duolingo (@severinhacker), Granola (@cjpedregal), Warp (@zachlloydtweets), Zynga (@markpinc), Groupon (@andrewmason), Coda (@shishirmehrotra), Opendoor (@ericwu01), and Flatiron Health (@zachweinberg). scuba.app

I’m stepping back from venture capital for the best possible reason – to get back to operating. Starting today, I’m CEO of General Medicine, leading the company alongside my friends and cofounders Ashwin Muralidharan and Elliot Cohen. Ashwin explains it below, and I’ll just add that these are my two favorite people to work with, and we have lots to do. More soon.

"I was born for this" — Megan Fox 🦊

Almost every founder has to survive some version of what Gabe describes here Although Rogo has raised over $300M, 40 investors passed on their Series A (except @rabois) Gabe on why every pass at that stage is a pass on the founder: "I met with Sequoia, Kleiner, Benchmark, everybody, and 40 people passed. And it wasn't just, you got the email with the deck and it's not exciting. It was, 'Oh, this is interesting. Let me meet Gabe. Oh, I kinda like Gabe. Let me spend an hour with him. Oh, Gabe, come to IC. Oh, Gabe, let's go to dinner. Oh, Gabe, come in for the weekend.' You know what? We're gonna pass. And it's so personal, because at that stage it has nothing to do with anything but you. Keith Rabois came a month after everyone else had rejected us, and Keith was like, 'Gabe, this isn't a contrarian bet. It's basically just Harvey for finance. Why would I do it?' And I said, 'Keith, if it's not contrarian, why did every single one of your friends just say it was a bad idea and not believe in me?'"

Wrapped Tefillin with legendary early-stage tech investor @davidtisch, founder of @BoxGroup, for the very first time in his life! David is one of the greatest early-stage investors in tech, with early bets on companies like Cursor, Ramp, Plaid, Warby Parker, and more. One of his biggest wins: BoxGroup invested $750,000 in Cursor’s seed round, a reported 1,300+X return following Cursor’s $60B acquisition by SpaceX. With Rosh Hashanah starting tomorrow, I couldn’t think of a more meaningful time for David to put on Tefillin for the first time and connect to the true source of our blessings. Mazel tov, David!

Today we're announcing our Series D: $115M raised, led by @Wellington_mgmt, at a $7.1B valuation. Our mission is to grow every company to its full potential. To do that, we need to do 3 things ⬇️

Some of the earliest money in Cursor (the largest vc-backed acquisition ever) turned a $750,000 investment into a ~$1 billion return. @davidtisch and his midas touch at Box Group strike again! Great profile here of one of the best early stage investors who wins while going against the grain @agarfinks fortune.com/2026/08/26/david…

Congrats to @mntruell @amanrsanger and the entire @cursor_ai team… We @BoxGroup have been investors since the very beginning and never sold a share… what an honor to be part of such a magical journey “Lots ahead”