2025-05-09 00:42:35
“I currently have ALL the 'Letters to a young investor' series starred in my inbox; its time to read them in full & fully dive in.” — a paying member.
Friends,
Marc Lore is cooking.
On Tuesday, Wonder announced a new $600 million raise, valuing his “super app for mealtime” business at more than $7 billion.
From The Generalist’s self-interested perspective, the timing could not be better. As part of the “Letters to a Young Founder” series, Marc and I recently discussed his methodical approach to raising capital, which we’re sharing with you today. The correspondences below offer an inside look at how one of tech’s most successful fundraisers has secured billions in venture funding.
A few bits of this edition that I especially loved:
Getting it wrong. Marc is super transparent about the times he’s gotten it wrong, discussing how he raised too much at Jet and got in over his skis. Every founder thinks they will never make this mistake…yet almost all do when given the chance.
A framework for raising capital. Marc seems to have a detailed, thoughtful framework for basically every core aspect of company building. Just as in the last edition, he has a rigorous way of thinking through raising capital.
The risk of maintaining the status quo. We get a fascinating inside look at how Marc thought through Wonder’s biggest pivot—away from food trucks and toward brick-and-mortar. I live to hear about these critical moments for founders.
How to operate in sixth gear. We get a lambent glimpse of Marc Lore’s intensity when he talks about going into “sixth gear” during company-defining moments.
I always enjoy this series, but I’m having a particularly good time learning from Marc, and finding ways of leveraging his advice to be a better builder of this humble publication :) If you missed our first letter, you can find it here:
To unlock Marc’s full letter, you’ll need to become a member of Generalist+. For just $22/month, you get exclusive interviews with elite founders and investors, tactical guides, a private database of high-potential startups, and our full library of case studies.
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Your cash burn is a key financial metric that indicates how quickly your company is going through its available capital — but how do you calculate it, and what’s a healthy cash burn? With Mercury’s easy-to-use calculator, you can find out in seconds. Not only will it help you crunch the numbers, but it will help you interpret your results and give you strategies to stay on track.
*Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.
Subject: The capital game
From: Mario Gabriele
To: Marc Lore
Date: Tuesday April 23, 2025 at 5:42 PM GMT
Hi Marc,
I’m heading back to New York in a few weeks and excited to try out Wonder for the first time! I don’t think you’d gotten the physical locations up and running last time I was in the city, so I’m looking forward to swinging by the Chelsea or Brooklyn spots and doing something of a personal food tour :)
I can’t tell you how much I love the organizational philosophy you outlined in our last letter. There’s something simultaneously surprising and logical about the Formula 1 style points system you use, for instance, and I’ve thought about it quite often since.
In addition to running a well-oiled operational machine, you have a reputation as an expert fundraiser. Looking at the numbers, I can understand why. Between 2014 and 2016, for example, you raised more than $500 million to build a direct Amazon competitor with Jet.
You’re taking an even bigger swing with Wonder, raising $1.4 billion (Update: Now more than $2 billion at a $7 billion valuation!) since its founding in 2021. You seem to have wielded the capital you’ve raised aggressively, buying out Grubhub for $650 million in 2024, for example. That’s not something most three-year-old startups are capable of pulling off, either financially or operationally.
For starters, I’m curious why you’ve chosen to follow such an aggressive capitalization plan with Wonder. From one vantage, it seems unavoidable. You’re trying to build a national-scale business in a highly operational, brick-and-mortar category. Though there are clever ways to change the traditional cost structure (which you’ve leveraged), large amounts of funding are simply necessary to execute at speed.
Still, I’m curious how you wrapped your mind around this. Did you ever consider a more conservative fundraising approach? Would it even make sense? Was there ever any concern about raising too much capital, especially as a nominal “seed”? I could imagine another founder preferring to raise a smaller initial round and de-risk the model more fully before tapping VC to the extent Wonder has. Was there an urgency around this idea and the current market dynamics that made you think you couldn’t afford to wait?
This may be a naive question, but did you have any concerns about being able to put that much capital to work effectively? Or, after 25 years of building operationally complex companies, has it simply become second nature to you?
Though Wonder seems to have grown rapidly (Update: Revenue is north of $2 billion, including Grubhub), validating your aggressive approach, there have been meaningful changes in the model that I’d love to hear how you reasoned through.
When you started, for example, Wonder utilized a fleet of vans that operated as mobile, micro kitchens. Couriers would drive to a customer’s house, then use the vehicle facilities to finish the meal, delivering it piping hot to their doorstep. It was a fascinating offering, promising a new level of quality in at-home dining, albeit with what looked like thorny operational complexities. In 2023, Wonder changed course, selling its vans and moving to more traditional brick-and-mortar locations.
To the extent that you’re willing to share, I’d be fascinated to hear what this period felt like from the inside, how you gained the confidence to make your decision, and if it impacted how you thought about Wonder’s fundraising journey.
Given how methodically you organize your team, I can imagine you’re similarly rigorous and strategic in how you think about timing and structuring your raises. What techniques have you found effective at driving a round to its conclusion? What have you learned after logging your “10,000 hours” of sitting across the table from venture capitalists and selling them on your vision? How have you succeeded in making your companies so capital magnetic?
Despite how effectively you seem to have raised capital from the outside, I know the truth is often much messier. Even the founders of supposedly “hot” companies often seem to have faced at least one round that required remarkable perseverance and a sheer force of will to get across the line. (In general, I subscribe to the view that every great company has at least one near-death moment, and often a handful.) Were there any raises that proved particularly challenging?
I’d love to hear how you approach this aspect of your craft, and thank you again for sharing your experience with me.
Best,
Mario
Subject: The capital game
From: Marc Lore
To: Mario Gabriele
Date: Thursday May 1, 2025 at 10:02 AM EST
Mario,
It’s good to hear from you, and I’m glad you enjoyed the last letter. It was fun to talk through it together.
You asked about raising money. It’s always been strange to me that every startup makes a business plan, but almost no one builds a “capital plan.” With every company I’ve built, I’ve mapped out from the very beginning the outcome we were aiming for, and the money we would need to reach it, step by step.
Here’s how I’ve put my capital plans together, starting at Quidsi and continuing to Wonder.
First, you have to start with a clear picture of what you’re aiming for. Ask yourself: What size market cap company does your vision support? If everything plays out as you hope it will, what scale outcome are we talking about? That depends on the market you’re attacking and just how ambitious you want to be. You have to be honest with yourself. Are we talking about a $100 million, $1 billion, $10 billion, $100 billion, or $1 trillion business? What order of magnitude are we building towards?
For example, let’s say a founder is shooting for a $1 billion outcome. That’s usually a pretty good sweet spot. You can see a path to building something of that size; it works for early-stage venture capitalists, and it’s not so crazy ambitious that it’s going to require a ton of capital. (If you’re aiming lower than that – say, $100 million – it’s hard to raise capital from traditional VCs.)
Next, you need to determine how much capital you’ll need to achieve that outcome. I use what I call “The Rule of 250” to guide my thinking about this.
Take whatever sized outcome you’re targeting – $1 billion in our example – and divide it by 250. In our case, we’re targeting $1 billion, so doing the math, we should raise $4 million to get started. If we were shooting for a $10 billion outcome, we should try to raise a lot more to get started and operate at a true startup pace, closer to $40 million. Not everyone can get that kind of capital out of the gate, and you need to have a plan that backs it up.
The next step is to operate at true rocketship cadence and raise accordingly. With my companies, my goal has been to double the amount I raise at double the valuation every 18 months. You can only do that if you’re executing, consistently banking 100% year-over-year growth, but that’s what I expect of myself and my team.
Obviously, you can tweak this to fit different businesses, market conditions, circumstances, and so on. But it’s a good framework to get started with and a helpful straw man to push against.
You can use our $1 billion example, do the math, and see how it works out:
Seed: Raise $4 million on a $8 million pre-money valuation, $12 million post-money.
Series A: Raise $8 million at a $24 million pre-money valuation, $32 million post-money.
Series B: Raise $16 million at a $64 million pre-money, $80 million post-money.
Series C: Raise $32 million at a $160 million pre-money, $192 million post-money.
Series D: Raise $64 million at a $384 million pre-money, $448 million post-money.
Keep the pace, and the next round is the $1 billion IPO.
It’s a great outcome for everyone. As a founder, you should still have about 20%, and your investors have made a great return, with IRRs of +70%. You consumed $124 million over five rounds to make it happen.
Now, what’s really useful about having a capital plan isn’t just seeing these numbers. It’s understanding what it means to build the business step by step. Instead of starting out by wondering “How do I get to a billion dollars?” you just need to ask yourself “How can I go from a $4 million seed to an $8 million Series A?” or “What can I do to get myself from a $12 million valuation to a $24 million valuation?”
Every round, you have to prove something different. You should outline that for yourself, too. (By the way, obviously, the names of the rounds don’t matter. It’s the same principle whether we call the $4 million first round a pre-seed, seed, Series A, or whatever.)
Seed is about having a vision. You need a big idea, attacking a big TAM, and you need to be a strong founder. You can raise it off the back of a good pitch deck. It’s a bit of sizzle.
When it gets to the Series A, you need to have something to show . A product, an app, data demonstrating that people are starting to use it. Investors should have the feeling of “Wow, this is exciting. I can see how this has come to life.” There’s still some sizzle here, but less.
2025-05-06 20:03:18
In a world where attention is fragmented and algorithms rule the content landscape, Chris Best and Hamish McKenzie are taking a radically different approach with Substack. Rather than chasing clicks, Substack focuses on a simple yet powerful idea: creators should own their work and make money directly from their audience through paid subscriptions. With over 5 million paid subscriptions and tens of millions of active readers, Substack has turned this model into a transformative force in media.
In this episode, Chris and Hamish unpack how they’re reshaping creator economics, navigating AI’s role in creativity, and enabling a new era for writers, from serialized fiction to short-form video. Their bet? That if content adds real value—whether it educates, entertains, or helps people earn—audiences will pay for it.
In our conversation, we explore:
How Substack grew from a simple newsletter tool to a multi-format media platform with 5 million+ paid subscriptions
Why the "soul connection" between creators and audiences is becoming more valuable in an AI-dominated world
The inside story of Substack's clash with Elon Musk and how it ultimately strengthened their platform
Why the ceiling for great writing and culture might be much higher than we're currently imagining
How Substack's subscription model creates dramatically better economics for creators than ad-supported platforms
Chris's "grand unified theory" for how AI will influence content creation and consumption
Why their short-form content isn't just a "sticky trick" but a pathway to deeper engagement and discovery
The future of traditional prestige media brands
Much more
Vanta: Automate compliance and simplify security.
Brex: The banking solution for startups.
WorkOS: The modern identity platform for B2B SaaS.
(00:00) Intro
(05:27) An overview of Substack and its current scale
(06:53) The origin story of Substack
(19:20) Finding the first believers
(24:17) Successful fiction on Substack, and why there’s potential for much more
(29:09) The different mediums available on Substack
(32:27) How Substack’s feed differs from social media
(37:33) The clash with Elon Musk and Twitter/X
(47:23) How Substack’s network helps creators succeed
(52:07) TikTok creators moving to Substack after the ban
(56:20) The future of paid media consumption
(58:24) Chris's grand unified theory of AI and media
(1:07:07) Substack’s AI tools
(1:10:54) Why it’s hard to predict where AI is taking us next
(1:13:42) Advice for traditional media institutions
(1:16:48) Final meditations
LinkedIn:https://www.linkedin.com/in/cjgbest/
X: https://x.com/hamishmckenzie
LinkedIn: https://www.linkedin.com/in/hamishmckenzie/
The Anxious Generation: How the Great Rewiring of Childhood Is Causing an Epidemic of Mental Illness: https://www.amazon.com/Anxious-Generation-Rewiring-Childhood-Epidemic/dp/0593655036
The Canterbury Tales: https://www.amazon.com/Canterbury-Tales-Geoffrey-Chaucer/dp/0140424385
Jairaj Sethi on LinkedIn: https://www.linkedin.com/in/jairaj-sethi/
Andrew Chen on LinkedIn: https://www.linkedin.com/in/andrewchen/
Mike Kerns on LinkedIn: https://www.linkedin.com/in/mike-kerns-63219/
Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/
Substack: https://substack.com/
Kik: https://kik.com/
Listicle: https://en.wikipedia.org/wiki/Listicle
The dress: https://en.wikipedia.org/wiki/The_dress
Craigslist: https://www.craigslist.org/
Stratechery: https://stratechery.com/
The Weekly Dish: https://andrewsullivan.substack.com/
Sinocism (Bill Bishop’s newsletter): https://sinocism.com/
The Chatner (Daniel Lavery’s newsletter): https://www.thechatner.com/
No one will ever read your book: https://www.elysian.press/p/publishing-industry-truth
After Babel (Jonathan Haidt’s newsletter): https://www.afterbabel.com/
Story Club with George Saunders: https://georgesaunders.substack.com/
Substack Notes: https://support.substack.com/hc/en-us/sections/14408747121940-Notes
Substack: Empire of Narratives: https://thegeneralist.substack.com/p/substack
Carla Lalli Music on Substack: https://carlalallimusic.substack.com/
The Parnas Perspective: https://aaronparnas.substack.com/
Baumol effect: https://en.wikipedia.org/wiki/Baumol_effect
Live video on Substack: https://support.substack.com/hc/en-us/articles/30316077882516-Getting-started-with-Live-Video-on-Substack
The Jim Acosta Show:
The Atlantic: https://www.theatlantic.com/
The Economist: https://www.economist.com/
The New Yorker: https://www.newyorker.com/
The Ankler: https://theankler.com/
The Bulwark: https://www.thebulwark.com/
The Free Press: https://substack.com/@thefreepress
I’d love it if you’d subscribe and share the show. Your support makes all the difference as we try to bring more curious minds into the conversation.
Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].
2025-04-29 20:03:04
Sequoia Capital is synonymous with outstanding performance, backing companies like Apple, Google, Airbnb, and Stripe. In today’s episode, I chat with Roelof Botha, Sequoia’s Managing Partner, about what it takes to see the future first, capitalize on it intelligently once it arrives, and help founders build enduring companies.
Roelof is especially well-placed to discuss such matters. Not only has Sequoia navigated more than 50 years of market cycles, Roelof has personally spent more than 20 years helping shape the firm’s unique approach. From honing a philosophy rooted in clear thinking and long-term vision to asking the tough question of "What would you do with only 12 months of runway?" Roelof breaks down the mindset that’s helped Sequoia and its founders thrive, and what others can learn from it.
In our conversation, we explore:
The psychological biases that most frequently derail investors
Why the first-mover advantage is often a disadvantage in technology
Why excess funding often undermines innovation
The story of PayPal's near-death experience and how it sparked its most critical innovations
How Roelof’s training as an actuary shaped his long-term thinking
How Sequoia maintains investment discipline through market cycles
Why they don’t use the word “deal” at Sequoia
How the US can maintain the lead in the AI race
The thinking behind the Sequoia Capital Fund and the firm’s organizational structure
And much more
Brex: The banking solution for startups.
WorkOS: The modern identity platform for B2B SaaS.
Explo: Customer-facing analytics for any platform.
(00:00) Intro
(04:50) Roelof on the AI bubble
(07:26) Sequoia’s Monday tracker and investment tools
(09:25) AI's role in business growth
(11:55) The challenge of spotting unicorns in a climate of rapid growth
(14:48) Roelof’s critique of capital-heavy AI startups
(19:30) A glimpse at how partners work at Sequoia
(21:43) A lesson from PayPal
(24:09) Roelof’s interest in decision-making and biases
(27:19) Two key biases: loss aversion and anchoring
(30:55) Examples of anchoring with Square and Twitter
(36:30) The case for long-term thinking
(41:00) Sequoia’s culture and commitment to winning
(48:38) What Sequoia looks for in founders
(51:39) How new technology enables less technical founders to succeed
(54:06) Why AI may favor incumbents over startups
(57:12) Where the US stands in the AI race
(1:01:16) The risks of government overspending
(1:03:54) Sequoia’s journey from idea to IPO
(1:10:44) How Sequoia uses AI
(1:15:05) Final meditations
Performance numbers shared in this interview are as of March 24, 2025. Past performance is not indicative of future performance.
LinkedIn: https://www.linkedin.com/in/roelofbotha/
Decisive: How to Make Better Choices in Life and Work: https://www.amazon.com/Decisive-Make-Better-Choices-Life/dp/0307956393/
Leading: Learning from Life and My Years at Manchester United: https://www.amazon.com/Leading-Learning-Years-Manchester-United/dp/0316268100
A Tale of Two Cities: https://www.amazon.com/Tale-Two-Cities-Penguin-Classics/dp/0141439602
Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl/dp/0807014273/r
Don Valentine: https://en.wikipedia.org/wiki/Don_Valentine
Daniel Kahneman: https://www.nobelprize.org/prizes/economic-sciences/2002/kahneman/facts/
Brian Chesky on X: https://x.com/bchesky
Michael Moritz on LinkedIn: https://www.linkedin.com/in/michaelmoritz/
Amos Tversky: https://en.wikipedia.org/wiki/Amos_Tversky
Pat Grady on LinkedIn: https://www.linkedin.com/in/gradypb/
Jack Dorsey on LinkedIn: https://www.linkedin.com/in/jack-dorsey-52409b243/
Alfred Lin on LinkedIn: https://www.linkedin.com/in/linalfred/
Elliot Jaques: https://en.wikipedia.org/wiki/Elliott_Jaques
Pik Botha: https://en.wikipedia.org/wiki/Pik_Botha
Matthew Rabinowitz on LinkedIn: https://www.linkedin.com/in/mattrverse/
Eric Yuan on LinkedIn: https://www.linkedin.com/in/ericsyuan/
Bret Taylor on LinkedIn: https://www.linkedin.com/in/brettaylor/
Joseph Schumpeter: https://en.wikipedia.org/wiki/Joseph_Schumpeter
Niall Ferguson’s website: https://www.niallferguson.com/
Jess Lee on LinkedIn: https://www.linkedin.com/in/jesskah/
Alfred Adler: https://en.wikipedia.org/wiki/Alfred_Adler
Sequoia: https://www.sequoiacap.com/
Sun Microsystems: https://en.wikipedia.org/wiki/Sun_Microsystems
Tandem Computers: https://en.wikipedia.org/wiki/Tandem_Computers
Oracle: https://www.oracle.com/
Cisco: https://www.cisco.com/
Gilt: https://www.gilt.com/
Rue La La: https://www.ruelala.com/
Roelof’s post on X about SPVs: https://x.com/roelofbotha/status/1895236567079530966
Paypal: https://www.paypal.com/
Airbnb: https://www.airbnb.com/
Otto von Bismarck’s quote: https://www.goodreads.com/quotes/294225-only-a-fool-learns-from-his-own-mistakes-the-wise
Adapting to Endure: https://www.sequoiacap.com/wp-content/uploads/sites/6/2022/06/Adapting-to-Endure_Sequoia-Capital-2022.pdf
The Sequoia Capital Fund: https://www.sequoiacap.com/article/the-sequoia-fund-patient-capital-for-building-enduring-companies/
Block: https://block.xyz/
Arab Spring: https://en.wikipedia.org/wiki/Arab_Spring
Time Span of Discretion by Alfred Lin: https://outlierspath.com/2023/06/25/time-span-of-discretion/
Natera: https://www.natera.com/
Sierra: https://sierra.ai/
Niall’s post on X about debt payments exceeding defense spending: https://x.com/nfergus/status/1893669468338815225
Sequoia Arc: https://www.sequoiacap.com/arc/
Iron Man: https://en.wikipedia.org/wiki/Iron_Man_(2008_film)
Groundhog Day on Prime Video: https://www.amazon.com/Groundhog-Day-Bill-Murray/dp/B000SP1SH6
What is Kodawari?: https://exploringkodawari.blog/what-is-kodawari/
Jiro Dreams of Sushi on Prime Video: https://www.amazon.com/Jiro-Dreams-Sushi-David-Gelb/dp/B008ODZEQ0
What is Logotherapy?: https://viktorfranklamerica.com/what-is-logotherapy/
I’d love it if you’d subscribe and share the show. Your support makes all the difference as we try to bring more curious minds into the conversation.
Production and marketing by penname.co. For inquiries about sponsoring the podcast, email [email protected].
2025-04-24 21:17:29
“Some of the best analytical work out there - we learn something new from every post!” - Peter, a paying subscriber
Friends,
If you want to, you can divide the world into two tribes.
There are the People of Certainty and the People of Doubt. I belong to the latter camp. There is no opinion I hold unequivocally. Everything look…
2025-04-17 21:15:54
“I think your Substack contains simply the best writings about venture out there. You provide a kind of storytelling and thoroughness that no one else does. Thanks :)” — David, a premium subscriber
Friends,
Successful serial entrepreneurs are a special breed. Though these founders might not have the unifying pleasure of working on one singular company across multiple decades, they get to test themselves in different environments and learn what works, not just once but repeatedly. Was how they structured the team at their first company smart or sloppy? Did they grow 300% year over year because they architected a high-output organization or because they happened across a hot space?
Building an enduring company requires both luck and skill; the serial entrepreneur has the opportunity to distinguish between the two with unusual precision.
In this edition of the "Letters to a Young Founder" series, I’m thrilled to share wisdom from Marc Lore, one of this generation’s best serial entrepreneurs. Over the past 25 years, Marc has created, grown, and successfully sold multiple businesses – including Quidsi (Diapers.com) to Amazon for $545 million and Jet.com to Walmart for an astonishing $3.3 billion. Marc led Walmart’s e-commerce push over the following 4.5 years, driving America’s biggest retailer into the digital age.
Today, Marc is applying his organizational genius to Wonder, a “new kind of food hall” that’s raised nearly $2 billion to reimagine how we experience restaurant-quality meals. It’s an ambitious undertaking that requires orchestrating countless moving pieces—from real estate and inventory management to culinary excellence and logistics—in an industry known for razor-thin margins and operational complexity. From the outside, at least, Wonder has the potential to become a generational player and the culmination of Marc’s remarkable career.
Throughout our correspondence, Marc reveals the frameworks and systems that have enabled his repeated success. His VCP (Vision, Capital, People) methodology is at the core – a systematic approach to translating audacious visions into concrete metrics, organizational structures, and accountability systems.
What’s particularly striking is Marc’s mathematical precision. Where many founders rely on intuition, Marc has developed quantitative systems for weighting priorities, assigning ownership, and measuring impact throughout his organizations.
For founders grappling with how to scale effectively while focusing on what truly matters, Marc’s insights offer invaluable guidance from someone who has repeatedly mastered this challenging transition.
Why Marc spends 90% of his time on VCP. Marc reveals how his Vision, Capital, People framework has guided his entrepreneurial journey across multiple billion-dollar exits, and why he believes founders who neglect these foundations are destined to fail.
The “ownership points” system Wonder uses to clarify everyone's impact. Marc's quantitative approach to measuring each role's impact creates transparency about value creation throughout the organization.
What it means to have “fat” in the organization and how Marc keeps Wonder lean. The systematic process Marc uses to identify where Wonder is over-investing relative to business impact and how he gradually rebalances resources.
Why Marc hired a Chief People Officer before almost anyone else. Against conventional startup wisdom, Marc made this critical hire during Wonder's earliest stages. He explains why most founders get this timing wrong.
How Marc builds a company that SOARs. Marc’s organizational structure is designed to maximize Speed, Ownership, Accountability, Results (SOAR). Optimizing for those traits creates a high performance and efficient machine.
…and much more. To unlock the full correspondence and everything else The Generalist’s premium newsletter has to offer, join today:
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Founders like Danny Meyer, the legendary restaurateur behind Shake Shack. Or Becca Millstein, co-founder of the viral brand, Fishwife. Or leaders like Siqi Chen, the CEO and CFO of Runway. Plus, a lineup of VCs and thought leaders sharing their hard-won answers to questions you just can’t Google.
Mercury believes that banking* should do more than hold your money. It should help you make your ambitions possible. That’s why they’re sharing a promo code for readers of The Generalist to get 50% off the full ticket price for their inaugural conference, Spheres, while tickets last.
RSVP with promo code HEMISPHERE to save $250.
*Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.
Subject: The architecture of an org
From: Mario Gabriele
To: Marc Lore
Date: Thursday March 27, 2025 at 12:38 PM GMT
Marc,
I am so excited to be starting this conversation with you, and I'm grateful for your willingness to share your wisdom with me and The Generalist’s readers.
Before turning to your far more formidable accomplishments, I hope you’ll allow me a brief opening gambit. My hope is that it helps frame why I think you’re such an interesting entrepreneur. And, that it leads us into this first correspondence.
When I was first trying to get into the world of startups, I had no concrete skills. I’d studied political science as an undergraduate, worked at a boutique law firm, started trying to write a novel, and then experimented with becoming a chef, attending culinary school and cooking at a modern French restaurant in New York. I’d followed that up by going to grad school to study International Development without a real plan for what I might do afterward.
While I was there, a germinating curiosity in technology turned into an obsession. But as that trajectory suggested, I had no obvious marketable abilities. I couldn’t code, had no design skills, and didn’t really understand what people meant when they said they worked in “product.” I asked a business school professor who had taken a shine to me how, with those limitations, someone like me might break in. (As you can sense from that question, I was still thinking in a very tracked, credentialed, un-startup way in those days.)
“You should be an athlete,” my professor told me.
Sensing my confusion, he explained what he meant. He wasn’t suggesting I don a pair of sprinting spikes and hot tail it to my local track, but be a business athlete. These kinds of people weren’t good at one specific thing but were sufficiently sharp and flexible to be useful across a few different functions. They might start by helping on a marketing task before hopping over to operations or pulling together a spreadsheet for an upcoming board meeting. They were, in effect, competent generalists rather than functional experts.
As you know much better than I do, in the early stage of a startup's life, almost everyone has to be an athlete to some degree. The best engineer might have to help out on customer support during a surge, and the CEO should be prepared to moonlight as an office manager, accountant, janitor, recruiter, and a dozen other roles. (As a company grows, the CEO has to maintain that level of mental dexterity, even as others on the team specialize, adding skills to keep a company growing.)
You have always struck me as one of the current generation’s great business athletes. I say that not because of your sporting connections, though they are considerable. For those who might not know, you ran track and field in college, are the incoming owner of the NBA’s Minnesota Timberwolves and WNBA’s Minnesota Lynx, and founded a venture firm with baseball’s Alex Rodriguez.
Rather, it’s because you seem to approach your work as a business builder with the same craft and dedication we expect from elite athletes. And while I piddled around in the rec leagues throwing up cinder blocks, you’ve been competing at an NBA level for over two decades, scaling massive, operationally complex companies from Quidsi (owner of Diapers.com) to Jet.com to Wonder. Along the way, you’ve landed massive exits, selling Quidsi to Amazon for $545 million and Jet to Walmart for $3.3 billion.
With Wonder, you’re taking another big swing, raising nearly $2 billion in venture and debt capital to build a “new kind of food hall.” (As my history suggests, it’s a concept I’ve always been fascinated by – I briefly helped a friend run a ghost kitchen serving burritos.)
More specifically, Wonder operates physical brick-and-mortar locations and a digital service. From a location on the Upper West Side or Wonder’s app, customers can order from multiple restaurants simultaneously – getting a starter from Marcus Samuelsson’s Streetbird, a pizza from Di Fara, and a cookie from Hungry Gnome.
It’s an audacious mission, requiring you to wrangle real estate, perishable products, beloved brands, temperamental customer preferences, and logistical complexities – in a category known for low margins with established competitors.
With that in mind, I was hoping to use this first correspondence to unpack how, precisely, you architect an organization to take on a challenge of this magnitude. Where do you begin? How do you stage what to focus on and when? How do you ensure that each function within a company is firing at the same time?
In researching your work, I came across a framework you like to refer to: VCP or Vision, Capital, People. When starting a new company, how do you think about turning a vision—which can often feel vague and amorphous—into a methodology that impacts how a business runs? At Wonder today, how do you translate your vision into day-to-day operations?
I suppose I am asking something like: how do you avoid “shipping your org chart?” For those unfamiliar with that phrase, it’s the idea that your product will follow the shape of your organization. If you’re shipping a frivolous mobile game, the consequences might be relatively low – perhaps there’s an inconsistent visual language across the app because your design and product teams barely talk. But when we’re talking about shipping food in all its logistical, emotional, and culinary complexity, the challenges seem undoubtedly greater. (I do not think I’m overestimating the intricacies of turning out consistent truffled mashed potatoes, but correct me if I am wrong.)
With much gratitude,
Mario
Subject: The architecture of an org
From: Marc Lore
To: Mario Gabriele
Date: Monday April 14, 2025 at 9:52 AM PST
Mario,
Thanks for kicking off this conversation. I can’t believe it, but it’s been 25 years of raising money and building companies. You learn lessons with each one, but it always comes back to Vision Capital People. Without exaggeration, I spend 90% of my time as a founder thinking about some aspect of VCP.
Why? Because you need to get the foundation right. Everything else follows from there.
You asked about Vision and how I translate that down to the business. Let’s start there and walk through how the right vision leads to picking the right strategies, which we measure with success metrics.
First, the vision. Explain what you’re going to build in detail, painting a picture of the future. This isn’t something you write once and then put away. You have to constantly come back to it and analyze it. Come back to the words you wrote down and interrogate them.
Maybe you wrote you wanted to build “the best Italian restaurant.” Ok, well, what do you mean by “best?” Is that actually what you mean? Do you want to be truly the best, number one in the world? Or do you just want to be better than your competitor? You have to flesh it out in detail and paint a picture of what the future looks like.
Once you have a vision, you must consider the strategies that get you there. When I say strategies, I don’t mean initiatives over a one-year period but 3-5 pillars that you’re building over the next 10 or 20 years. Strategies are the how: how you and your company will make your vision a reality. These will change more often than the vision, adapting alongside the business.
How do you know if you’re delivering on your vision or that your strategies are working? You need to pull each one down into success metrics.
2025-04-15 20:03:08
Friends,
What if you could record the smell of your grandmother’s kitchen or detect diseases with a breath? Josh Wolfe, co-founder of Lux Capital, is funding the breakthroughs that are turning these concepts into reality.
In this episode of The Generalist, Josh discusses how Lux Capital is backing companies like eGenesis, which is transplanting gene-edited pig organs into humans; Osmo, pioneering digital olfaction technology; and Variant Bio, which is studying genetic outliers in indigenous populations whose DNA could lead to life-saving medical advancements.
Science fiction doesn’t just predict the future, it creates it. Josh’s investment approach is deeply influenced by speculative fiction, which has inspired many of the groundbreaking companies in his portfolio. This visionary thinking has driven Lux to fund startups working on technologies once considered impossible.
Josh also shares how stories shape his worldview, how he stays on top of macro trends, where America is trailing China in the AI race, and how we can catch up.
In our conversation, we explore:
The revolutionary development of genetically modified pig organs being transplanted into humans and what this means for the future of organ transplantation.
The recent achievement of "teleporting smell" across space and why computers that can replicate scents will open up entirely new industries.
Why Lux is investing in the search for real-life "X-Men" — genetic outliers in isolated populations whose DNA could lead to life-saving medical advancements.
How Josh evaluates macro trends to make smarter micro investment decisions and why ignoring the big picture is a mistake.
The three tech sectors that Josh believes will define the geopolitical balance in the decades ahead.
How Josh stays current on macroeconomic trends.
Much more
Brex: The banking solution for startups.
WorkOS: The modern identity platform for B2B SaaS.
Generalist+: Essential intelligence for modern investors and technologists.
(00:00) Intro
(04:38) A brief overview of Josh’s work at Lux Capital
(05:57) The science fiction to science fact pipeline
(09:11) Xenotransplantation
(12:10) Proven transplantations with modified pig kidneys, and what’s next
(15:38) Ethical questions around xenotransplantation
(17:48) Lux Capital’s investment in eGenesis
(19:34) The theory of persistent cellular memory
(23:35) Why eGenesis began with kidneys
(24:30) Digitizing smell
(32:24) Commercializing digital olfaction technology
(38:26) The potential applications for a “Shazam for smell”
(43:16) Variant Bio’s work studying genetic outliers
(52:00) Variant Bio's two primary clinical focuses
(53:46) How Josh stays current on macroeconomic trends
(59:44) Josh’s thoughts on the critical areas the U.S. should invest in
(1:14:00) How to win the talent war
(1:18:53) Final meditations
LinkedIn: https://www.linkedin.com/in/josh-wolfe-7883/
20,000 Leagues Under the Sea: https://www.amazon.com/000-Leagues-Under-Wordsworth-Classics/dp/1853260312
War of the Worlds: https://www.amazon.com/War-Worlds-H-G-Wells/dp/8175992824/
In Search of Lost Time: https://www.amazon.com/Search-Lost-Time-Library-Classics/dp/0812969642
Perfume: The Story of a Murderer: https://www.amazon.com/Perfume-Story-Murderer-Patrick-Suskind/dp/0375725849/
Poor Charlie's Almanack: The Wit and Wisdom of Charles T. Munger: https://www.amazon.com/Poor-Charlies-Almanack-Charles-Expanded/dp/1578645018
George Church on LinkedIn: https://www.linkedin.com/in/george-church-2b86301/
David Deutsch on X: https://x.com/daviddeutschoxf
Karl Popper: https://en.wikipedia.org/wiki/Karl_Popper
Feng Zhang on X: https://x.com/zhangf
John Maraganore on LinkedIn: https://www.linkedin.com/in/john-maraganore/
Vicki Sato: https://en.wikipedia.org/wiki/Vicki_Sato
Robert Nelson on X: https://x.com/rtnarch
David Shenkein on LinkedIn: https://www.linkedin.com/in/david-schenkein-md-45342476/
Alex Wiltschko on X: https://x.com/awiltschko
Richard Axel: https://www.nobelprize.org/prizes/medicine/2004/axel/facts/
Andrew Farnam on LinkedIn: https://www.linkedin.com/in/andrew-farnum-4b180a1/
Chris Hohn: https://ciff.org/team/chris-hohn/
Charles Darwin: https://en.wikipedia.org/wiki/Charles_Darwin
Isaac Asimov: https://en.wikipedia.org/wiki/Isaac_Asimov
Neil Gaiman: https://en.wikipedia.org/wiki/Neil_Gaiman
Terry Pratchett: https://en.wikipedia.org/wiki/Terry_Pratchett
Neal Stephenson’s website: https://www.nealstephenson.com/
eGenesis: https://egenesisbio.com/
Xenotransplantation: https://egenesisbio.com/xenotransplant/
Surgeons Transplant Engineered Pig Kidney Into Fourth Patient: https://www.nytimes.com/2025/02/07/health/fourth-pig-kidney-transplant.html
Can an Organ Transplant Change Someone’s Personality? https://www.psychologytoday.com/us/blog/the-leading-edge/202402/do-organ-transplants-cause-personality-change-in-recipients#
Personality changes following heart transplantation: The role of cellular memory: https://www.sciencedirect.com/science/article/abs/pii/S0306987719307145
Kallyope: https://kallyope.com/
Letter from the founder: https://www.osmo.ai/blog/letter-from-the-founder
Plum 1.0: https://osmostudios.ai/products/plum1o
IFF: https://www.iff.com/
Firmenich: https://www.dsm-firmenich.com/en/
Variant Bio: https://www.variantbio.com/
Gates Foundation: https://www.gatesfoundation.org/
23andme: https://www.23andme.com/
Genentech: https://www.gene.com/
PCSK9 gene: https://medlineplus.gov/genetics/gene/pcsk9/
Leonardo da Vinci DNA Project: https://www.jcvi.org/research/leonardo-da-vinci-dna-project
CBGB: https://www.cbgb.com/
Coney Island High concert history: https://www.concertarchives.org/venues/coney-island-high--5
Community Notes: https://help.x.com/en/using-x/community-notes
Chinese Missile Destroys Satellite in 500-Mile Orbit: https://www.npr.org/2007/01/19/6923805/chinese-missile-destroys-satellite-in-500-mile-orbit
Logic Pro: https://www.apple.com/logic-pro/
GarageBand: https://www.apple.com/mac/garageband/
NVIDIA: https://www.nvidia.com/
Trump pulls $400m from Columbia University, saying it failed to protect Jewish students: https://www.bbc.com/news/articles/c4gp979w055o
Cuban Missile Crisis: https://en.wikipedia.org/wiki/Cuban_Missile_Crisis
Josh’s post on X about Islamic extremists in Africa: https://x.com/wolfejosh/status/1241912312493215744
Africom: https://www.africom.mil/
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