We The Builders

Intro

Seth Berman is the cofounder of Susa Ventures and Kivu Ventures. He started angel investing at Y Combinator demo days back when there used to be twenty companies and a handful of investors looking at them. He then went on to start one of the early few seed funds funding 10 unicorns across ~100 investments. Some of these include companies like Robinhood, Flexport and Chapter (Cofounded by Cobi Blumenfeld-Gantz, who has also been on the show). See link below to the original episode.

Special thanks to Cobi for the intro. We filmed this in Aspen CO on my first trip there. Since I don’t ski, the only reason I had heard of the city was Aspen Institute and their events.

Highlights

Sharing below some of the topics we covered in the episode. You can also check out the Full Episode on YouTube.

The Early Days of Seed Investing [02:03 - 04:31]

* “I was angel investing starting in 2010 and I was fortunate enough to be one of the first people that would go to Y Combinator’s demo days.”

* “When I started going, it was probably 12 founders that were presenting and 12 investors in the audience.”

* “I think we invested in five or six companies that became unicorn businesses in a fairly small portfolio.”

The Explosion of the Seed Ecosystem [05:34 - 09:00]

* “There’s now 900 plus seed funds out there in the ecosystem.”

* “Any great company that’s running a competitive process, if they’re talking to 20 funds, 19 of them are going to lose and one of them is going to win.”

* “What used to be seed is now series A and what used to be pre-seed is now seed.”

* “It’s very challenging for them to let other large seed funds in or multi-stage funds. So it becomes a winner take all round.”

The Series A Opportunity [09:00 - 10:30]

* “I felt like there’s a tsunami of seed-stage deals coming to series A.”

* “I graduated from doing seed to series A and B now.”

* “I’m more focused on companies that have some sort of product market fit.”

* “Series A funds, there’s probably 30 super high quality funds, but there’s not 900.”

Missing Out on Pinterest [10:30 - 12:40]

* “One of my biggest misses was Pinterest. I remember meeting with the founders outside at TechCrunch Disrupt.”

* “The number that I remember seeing was they are over 20 minutes time on site per day. And that was a similar number to what Facebook had.”

* “I should have known that with that much engagement, they were going to build something really special.”

The Era of the “No-Deck” Fundraise [12:50 - 13:47]

* “Any founder that has really strong experience can go out and fundraise with no product.”

* “They can literally just have an idea and pitch it and raise funding and not even a deck.”

* “A creative can come in with no technical expertise really and build a sizable business.”

* “The gates are down. And if you’re a creative person or entrepreneurial person and you have an idea... it’s easier ever to build a product.”

Vertical AI and the Super Cycle [13:34 - 14:43]

* “What we’re seeing in AI... it’s changing everybody’s workflow on a daily basis.”

* “A lot of these models whether they’re vertical specific or they’re horizontal is they’re breaking the benchmarks way faster than anybody could imagine.”

* “I see adoption of them at my much higher rates than I’ve seen other super cycles in the past.”

AI 2.0: Physical Intelligence [14:43 - 16:15]

* “We call it physical intelligence... we think AI 2.0 is really when intelligence starts affecting physical objects.”

* “There’s going to be so many different things that are going to happen over the next 5 to 10 years that bring intelligence into every person’s life on a daily basis.”

* “Bring intelligence into every person’s life... on the manufacturing floor in agriculture and in construction.”

* “We’re trying to find kind of the picks and shovels that invest in those models and in those businesses to allow this new ecosystem to be built.”

Starting a Company vs. Solving a Problem [22:28 - 23:25]

* “I think there’s two types of entrepreneurs. I think there’s an entrepreneur that wants to start a company and there’s an entrepreneur that wants to solve a problem.”

* “We tend to want to invest in entrepreneurs that are trying to solve a problem.”

* “Experience that problem before... have some domain expertise to understand why the problem exists and how to solve it.”

The AI Scientist [32:10 - 34:01]

* “Instead of having a few thousand researchers you can have billions and you can replicate them over and over and over again.”

* “An AI agent can have access to everything and be able to analyze it constantly.”

* “I think there’s going to be profound discoveries over the next decade from these AI scientists.”

* “They’re going to hit prime human sometime in the next two to five years. Prime human being, Albert Einstein level intellect.”

Vertical vs. Horizontal Models [35:51 - 37:21]

* “A startup raised like $50 million to build this model... they tested it against ChatGpt and ChatGpt was better.”

* “They just spent $50 million for nothing... you just don’t have the same sort of resources as these horizontal models and access to compute.”

* “These models might just be so powerful that you don’t need a lot of these vertical specific companies out there today.”

Why Founders Don’t Care About Your VC “Platform” [39:19 - 41:12]

* “If they get multiple term sheets from the tier one funds, they tend not to care so much about the platform and the services.”

* “They care more about the partner that they’re going to be working with.”

* “What we found is it’s very hard to have specialists in every single vertical.”

* “Unless you’re kind of within the sweet spot of the individuals that they hired at that fund... they tend not to be that helpful.”

Investing is Harder Than Tweeting [48:04 - 48:53]

* “I think that investing is incredibly difficult. You only have so much time during the day.”

* “It’s very hard to have the time to kind of build up an online presence.”

* “My focus has always been on do the best deals possible, support those founders, and have those founders speak highly about you.”

Identifying Talent: Broken Resumes and Persistence [01:10:48 - 01:15:00]

* “Sometimes the most talented people have broken resumes. They don’t check the boxes... the credentials aren’t there.”

* “You want somebody that is extremely persistent that is going to run through walls to make things happen.”

* “It’s a very different skill set building a product and building a team and making that team successful.”

* “A lot of founders... they don’t put the resources or the time into go to market at the early stages.”

Timing: Catching the Wave [01:32:00 - 01:35:50]

* “Sometimes as investors, we’re so far in front of the wave and the wave isn’t coming for 10 more years that, you know, we’re just never going to catch it.”

* “Catching it too late... you invested in a social network in 2012 or 2014, you’re probably too late.”

* “Understanding what potential outcomes can be is like absolutely critical to being a great investor.”

The Future of Public Markets and AI Analysts [01:38:16 - 01:43:12]

* “You could go public when you’re doing like 150 million of revenue 10 years ago... in the next two years it might be you have to be doing a billion of revenue.”

* “AI might change that... you might not need those public market analysts anymore and then a lot of these businesses could start going public much earlier.”

The Robinhood Story [01:45:00 - 01:48:00]

* “We met them... and they kind of told us their vision of fee free trading.”

* “We were the only investor that was willing to kind of open up our our books and be like the the investor of record for FINRA.”

* “My feeling on why they were so successful was it was really intuitive UI and it was just a great user experience.”

* “I kept 80% of my stock. So, I still own a lot of Robinhood stock.”

Exceptional Go-To-Market is Now Required [02:00:04 - 02:01:08]

* “Go to market has just become so much more challenging and the go to market motion... needs to be so more highly refined.”

* “If you have the resources, your go to market team should be equal to your product and engineering team.”

* “Build a world-class team around whatever channel you want to focus on and find peo…

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wethebuilders.us

Who is Ali Jehangir Siddiqui and why I was interested in having a conversation with him?

Ali is an entrepreneur, investor, diplomat and industrialist. When I first met Ali in 2017, he was the Special Assistant to Prime Minister Shahid Khaqan Abbasi of Pakistan. For my friends in the US, that would be like the President’s Chief of Staff. He also didn’t need the job. He had built one of Pakistan’s fastest growing banks in JS Bank (now over $4B in assets), built the largest carbon-neutral private steel industries in the UAE (Arabian Gulf Steel Industries), founded the first private domestic airline with AirBlue and was central to growing the Jahangir Siddiqui Group into easily the Top 10 family business empires out of Pakistan.

I recently got interested in the history of patronage which got me into the history of Medici family from Renaissance Europe, one of the wealthiest families in the 15th century. When we caught up after recording the episode, I was curious about whether Ali had studied them before starting the bank given his interest in Austrian and European history — unsurprisingly he had deeply studied both the Medici and Fugger families before starting the bank. Given the unique range and adaptability Ali has shown by reinventing himself in different industries every few years (venture capital & private equity, commercial airline, steel & glass manufacturing, foreign diplomacy, climate-tech to name a few) it would be fair to categorize him as a Renaissance Man of our era at the heart of building and growing what future historians will probably refer to as the House of Jahangir Siddiqui (JS Group).

Ali and I reconnected last year after seven long years. Even though we have had limited interactions, he has had some of the most formative impact on my life trajectory and career since I have met him. I will share those exact moments in a bit but first some context is important on where I was at in life at the time.

I was working on playing my part in growing a still nascent entrepreneurship ecosystem in the country by organizing business plan competitions in 20+ universities across the country. I was doing this as the head of Pakistan’s national campus program for Hult Prize Foundation which would grant $1 million to a team of student entrepreneurs working on a specific challenge every year.

This took me to New York City to the annual final event where $1 million is awarded which overlapped with the UNGA week which brings together all world leaders. Ali was in town as part of the Prime Minister’s delegation and was helping coordinate high stakes meetings with other heads of states, billionaires and so forth in a very short three day trip. On that same trip, I was introduced to Ali through a mutual to discuss potential collaboration opportunities with the government.

Ali was gracious enough to carve out time for me, my colleague and the Hult Prize winning team that year. At the end of the meeting, he came up to me and said that he is close with the Prime Minister and his sons and that I should become friends with them. He scheduled a 45-min meeting for all of us and the rest as they say, is history.

What did that particular instance do? It showed me that if you are ambitious and you work hard, there is some sense of meritocracy in the world. That you in fact can change the trajectory of your life. It showed me that anything is possible and people are just people at the end of the day even if they have fancy titles or 20-car motorcades. I did not come from the wealthiest family or the most powerful but was able to open doors, that changed how I have looked at life ever since.

After I was back in the country, I kept nagging Ali and his chief of staff at the time and would try to meet him for all sorts of stuff. My different business ideas at the time, my job and just try to learn from him by finding an excuse to spend some time together. During one of these trips to the Prime Minister’s office, he showed me this app called RelSci where you could list your most powerful/well networked connections and map out an exact path to anyone in the world.

This taught me that anyone in the world is at most six degrees removed. Donald Trump was President at the time, just as an experiment I checked for a path to him and saw that Ali was four degrees removed. It would later turn out that he would get appointed as the Ambassador to the U.S and thus I would be one degree removed. I never asked for any introduction, well at 21 I wasn’t doing something that would warrant the request for such introductions but it taught me a critical lesson: relationships run the world and anyone including the President of the United States is at most six degrees removed from you.

In this conversation:

We talk about the pros and cons of the CEO role in companies, optimizing your career around your strengths, cold outreach, taking over a successful family business, spotting and nurturing outlier talent, consuming media and making sense of the world, the concept of rules being counterintuitive to innovation, the concept of shorting people, the art of relationships, mentorship, evaluating opportunity costs and more.

Watch on Youtube

Timestamps

00:00 - Introduction01:31 - On doing his first ever long form podcast06:24 - Operating philosophy and not taking CEO roles 13:28 - On optimizing his career around strengths 17:00 - Lessons from working with one of Asia’s largest VC firm21:30 - Social media presence and identity24:00 - Media diet, continuous learning, questioning institutional programming & making sense of the world 33:00 - The art of cold outreach, warm intros and 40:20 - Spotting, hiring and nurturing outlier talent54:25 - Ambition, problem-solving archetype56:00 - Taking over a successful family business1:04:25 - Talent retention 1:14:55 - Mentorship1:21:00 - The concept of rules is counterintuitive to innovation1:24:31 - Evolution of venture capital1:32:06 - The art of relationships 1:38:13 - Shorting people 1:41:16 - What is more important? The network or the product?1:51:01 - Building OnZero 02:01:25 - Evaluating opportunity cost and the 10 year plan 2:10:30 - Closing thoughts and rapid fire

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wethebuilders.us

I had a conversation with Jonathan about choosing what to work on, getting the government as a customer, fundraising and how too much money can hurt the culture, favorite interview questions and more.

Check out the full episode wherever you get your podcasts or right here on Substack. Sharing some of my highlights below.

How do you know you are working on a problem worth solving?

- You can feel if you’re solving a big enough problem for someone through their like reactions to things, such as people falling off chairs in conference rooms as we showed them what we could do.

What does product market fit feel like?

- Early government customers literally bought Chainalysis on expense credit cards and used emails that didn’t have real government affiliation.

How do you sell to the government?

- The core strategy in selling to the government is: how do you make people’s careers?

How much of growth fundraising is about financial vs. the story?

People get behind the story and even very very smart people look at numbers differently depending on how emotionally bought in to the story they are.

Watch on YouTube:

Timestamps

00:00 - Introduction

04:11 - Growing up as an immigrant in London and the “chip on my shoulder”

09:18 - Why market sequencing is critical

16:23 - Choosing to take up the CEO role and the domain of sales

23:20 - Early transformational experiences and the entrepreneurial bug

26:13 - How to penetrate the government

30:57 - Importance of storytelling, emotional and intellectual storytelling

38:26 - Raising funds and why too much money can hurt a culture

42:23 - Lessons in creating a culture

48:50 - How to hire executives

55:44 - Jonathan’s favorite interview questions and hiring philosophy

1:02:09 - Exciting things in the next 20 years

1:06:44 - The “two-stage rocket” of fundraising

1:11:45 - Loneliness of being a CEO

1:12:55 - Rapid fire and closing questions

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wethebuilders.us

Of all the guests I have had on the show, Bharat has probably had the most dynamic career. He has been an executive at public companies, been a venture capitalist, an investment banker and a founder.

Our story goes back to when I got David Friedberg (Cohost All-In Podcast, Cofounder Ohalo, The Production Board) for the Building Atoms Summit in Nov 2023. My internal champion was the Chief Brand Officer of The Production Board at the time, Rachel Konrad who has become a friend and mentor. She just found the story of how I just orchestrated running into Friedberg outside Starbucks really funny and gave it her all to make the event happen.

Since I have known Rachel, she has been telling me to meet Bharat and somehow knew that we would get along. After a couple of failed attempts over 2 years we finally got together over a dinner I hosted and have become friends ever since. She probably described him best as “lighthearted but not lightweight” and that will come across in our conversation.

We talk about our military upbringing and how that teaches adaptability, culture at companies and how startups are like little cults, how life is different at the abstracted management layer in corporates vs. startups, storytelling, resource allocation, time management, insiders vs. outsiders and the value of a network and more.

Watch on YouTube

Timestamps

00:00 - Introduction02:50 - Bharat’s career trajectory 07:36 - What military upbringing taught me 11:02 - Being authentic to yourself 19:47 - The co-founder dynamics and culture building28:57 - The navy vs. pirate team structure32:56 - What does follower-ship mean? 40:11 - What comes first? The mission or the people?43:20 - All startups are cults 48:15 - How Bharat allocates his time1:00:12 - Learning from Venture, Corporate and Startups01:12:24 - Resource allocation 01:22:03 - Developing a thesis and discarding an idea01:31:22 - An outsider becoming an insider01:42:52 - How should one build trust 01:47:48 - Building value over time 1:56:40 - Choosing What Not To Build2:03:00 - Why Canva & Figma Worked and the Future of Media02:15:45 - Distribution vs. Production2:25:40 - What Compounds as a Founder02:27:48 - Closing Rapid Fire

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wethebuilders.us

Twitter/X is a battleground where you defend your ideas and murder the ones you don’t stand for (as you will hear in Mike’s own words). There is little room for nuance as I too have observed and so the Twitter/X persona of people you see often wouldn’t be the right way to categorize the person.

As I prepared for this episode, I discovered how Mike has changed his opinion on topics throughout the years after discovering new information. He is one of the most independent minded people out there and it was fun to sit down for a conversation on media, Pirate Wires, Founders Fund marketing, state of advertising, charter cities and more.

Mario Gabriele did a four part series on Founders Fund a while back and described their marketing strategy as soft power initiatives. Some of these included Peter’s book Zero To One, Hereticon and Pirate Wires to name a few. Mike Solana has been at the centre of this strategy which made him a billionaire media tycoon (iykyk). At Founders Fund, he has been able to stay ahead of rivals with a team only four full time people on the marketing team compared to teams of fifty at other funds of similar size. Now he helps us make sense of the world of tech, business and politics through Pirate Wires.

Friend of the pod Christopher Lochhead🏴‍☠️ would probably agree that Mike has been able to build new categories around ideas he stands for representing important problems of the time. Some of these are limited standalone brands, others are cultural movements. One example of this is Hereticon, where he was able to create the category of “Thoughtcrime” which went mainstream after Elon bought Twitter. There were two editions of Hereticon (2022 & 2024) and it looks like it won’t make a comeback.

Mike’s strategy is to be different. Once you have created a category and are not unique anymore, you move on. In true Zero To One fashion.

Timestamps

00:00 - Introduction03:06 - Building a media company vs building a tech startup05:41 - Building culture in a company11:36 - Substack vs having your own website17:51 - The utility of advertising 29:24 - Building a large audience vs. building a quality audience35:55 - Twitter strategy and evolution in the past 5 years47:10 - Pirate Wires master plan and inspiration from Walt Disney53:16 - Charter cities in America 1:03:03 - The podcast experiment1:15:03 - Mike’s information diet1:29:18 - Working on Zero To One with Peter Thiel and marketing at Founders Fund1:38:05 - Rapid fire and closing thoughts

Watch on YouTube:

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wethebuilders.us

I first found Mike Maples when I came across his podcast with Osman Rashid, (Cofounder of Chegg) about 6 years ago. I have since admired Mike’s philosophy on startups and investing. Mike is an early investor in category defining companies like Twitter, Okta, Chegg, Twitch, Clover Health and Applied Intuition to name a few.

I hosted a dinner on the topic of technological stagnation about 3 years ago with Mike and a few other investors and founders, this was pre-ChatGPT, before defense or dual-use investing went mainstream and before reindustrialization became a national agenda for the US.

We look back at what has changed in the last few years and if we are making progress at a better rate in the world of atoms than before. In one way, Mike has seeded the reindustrialization movement by investing in Chris Power, Cofounder of Hadrian (which was the only investment he made in 2021) and key orchestrator of the marquee Reindustrialize Conference in Detroit which is leading the way on building a platform for policymakers, startups, capital allocators and manufacturers on bringing back the most critical industries through advanced technology adoption.

In this episode, Mike talks about how startups have to build a radically different future and through great storytelling bring their customers, investors and employees to their version of the future which they are already convinced of. I also asked him about the origin stories of investing in and finding Twitter, Digg and Lyft.

We also discuss how Floodgate differentiated itself in 2015 when they were a decade into seed investing and again in 2025 two decades into seed investing. Floodgate has a concentrated investing strategy and having been around for 20 years, they are unique in the sense that they were not tempted to go raise a mega fund and maintain a fund size of around $150m and do only seed.

I really enjoyed spending a couple of hours with Mike, I hope y’all enjoy this one.

One of my favorite quotes from the episode among gems Mike dropped:

Even being different worse is better sometimes than being better at the same (thing). - Mike Maples Jr.

Special thanks to NFX for hosting us for this episode.

Watch on YouTube:

Timestamps:0:00 - Introduction02:32 - Technological stagnation and are we on track to build the Jetson’s future? 10:46 - Startups avoid the comparison game and why the best founders are great storytellers19:00 - The insight is the magic and the breakthrough mechanism 26:44 - Is founding companies art or science? 30:21 - Funding talent in pursuit of interests39:49 - Story of investing in Qasar Younis of Applied Intuition 45:00 - How Floodgate is different and reinventing itself now51:00 - Founder archetypes that fit the Floodgate thesis58:46 - “Disagreeableness” as a skill in founders 1:08:56 - Decisions that compounded 1:19:11 - Learning from legendary founders and early investment stories1:33:00 - Being your own personal monopoly 1:37:03 - Non Consensus Investing 1:47:11 - Why write Pattern Breakers?1:51:19 - Advantage of smaller funds 1:59:45 - Favorite books, TV shows, movies

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wethebuilders.us

If you’ve spent any time in tech over the past few years, you’ve probably read Not Boring or at least seen a screenshot of it on X/Twitter. Packy built it from a Substack assignment during David Perell’s Write of Passage course into one of the most-read newsletters in technology, now at over 250,000 subscribers.

Encouragement goes a long way. David in that course told him his first assignment was the best piece of writing he had seen in the class which gave Packy the confidence to keep going. He talks about his fear of being made fun of (by your friends) if you publish on the internet or nobody caring and ever reading. I can relate, it is one of the reasons I recorded for 6-7 months before hitting publish in July last year. The funny thing is, 250,000 subscribers later that feeling never completely goes away. We touch on that too.

Every Not Boring essay is a full-stack teardown, part history lesson, part strategy memo, part “why this would matter in 10 years.” Today, Packy sits at the intersection of media and venture, David Perell described this new era of creators and personalized business models as building a personal monopoly. This applies to podcasting, newsletters or blogs and any other form of new media at the intersection of tech and business where the differentiation lies in the creator - they are like Hollywood talent and the brand they represent is secondary and in some cases irrelevant. They are the brand. We live in the era of what my friend Christopher Lochhead🏴‍☠️ would call creator capitalism.

For Packy, great writing is deal flow. He has invested in companies like Ramp (now valued at over $32B) and Astro Mechanica (bringing back supersonic air travel) and many more through his fund. What he now spends most of his time on is doing well researched deep dives which are a function of the relationships he builds along the way.

If you are chronically online on X/Twitter, you would have seen his latest masterpiece, a deep dive on a16z and if you’re not chronically online, here is the link:

We have a wide ranging conversation including about his prior life in coworking industry and takeaways from being in that business, we talk about starting on Substack vs other platforms, business models in new media, his thesis for vertical integrators and more. Hope you enjoy!

Timestamps

00:00 - Intro

01:11 - Why publish on Substack and the origins of Not Boring

01:42 - Write of Passage with David Perell

04:51 - The content pyramid and compounding experiences

15:46 - Insights from working in co-working industry

28:07 - The Ramp case study and the concept of uncertainty window

36:56 - Ramp vs Brex

41:32 - Vertical integrators thesis

51:45 - Media, venture, and the future of tech media

00:00:55 - Twitter vs Substack for creators

1:10:19 - Advice to We The Builders

1:12:59 - Growing the team, getting better, and hiring

1:21:57 - Playing the long game, measuring success over decades

1:33:32 - Wrapping up — favorite shows and books

1:40:53 - Signing off

Watch on YouTube:

- Suffiyan Malik

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wethebuilders.us

New Year’s Eve special: I recorded this one at the Founders Fund office on Nov 6, 2024, right after election day. It was originally scheduled to be over zoom but I read Delian’s blog post called “Thirty Observations at Thirty” where one of the things he talked about was prioritizing in-person whenever possible so I decided to make the trip to Miami.

Delian dropped out of MIT, became a Thiel Fellow, a program with ~300 fellows who have started companies valued at over $750B. I saw a chart according to which Thiel Fellowship has a 5.9% unicorn hit rate, which probably makes it the best program for entrepreneurs ever. We will cover this story with friend of the pod Danielle Strachman who built the program in Q1 2026 but for now, sharing a tweet below to sum it up:

He interned at Square $XYZ when it was around ~100 employees, got to see Jack Dorsey at work and got to meet operators like Kieth Rabois who he would go on to work with at Khosla Ventures. This would turn out to be an apprenticeship that put him on the path to be one of the best seed investors in the industry.

His record as a seed investor:

Ramp is now valued at $32B, Hadrian and Sword are also unicorns and Varda is going to be probably be the biggest among them. (Disclaimer: I am a proud tiny shareholder in the company)

The narrative around why college doesn’t work at least in my echo chamber is well understood but I wanted to ask Delian what college was actually useful for so we had a conversation around that.

We also talk about that, the experience at Square, what led to the apprenticeship with Kieth Rabois, learning cult building and the very Silicon Valley like pay-it-forward culture of mentoring from the college fraternity and up-skilling for Varda Space among other things.

Delian on the incredible access and opportunity of working with Kieth as his chief of staff of sorts:

“Maybe you have to get a diet coke or coffee but you get to be in an Affirm board meeting with Max Levchin”

Happy New Year and hope you enjoy!

Timestamps

00:00 - Intro00:30 - Writing and Flow State05:12 - Dropping Out 12:13 - What MIT was good for20:16 - Early days at Square25:16 - Parents reaction to joining Thiel Fellowship29:44 - Transferrable skills from frat days34:02 - Lessons from Keith Rabois45:15 - Building Varda52:58 - How Mafias are built57:53 - Culture at Varda

Watch on YouTube

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wethebuilders.us

I got to sit down with Glenn Fogel, CEO of Booking Holdings, the largest travel company in the world. $BK NG market cap was $160B as of Dec 3, when I am publishing this. For context, it’s market cap is ~2x that of Marriott and AirBnB, which are 2 and 3. Here is a chart of the rest on the list:

I knew travel was big but I did not know it was roughly 10% of Global GDP. According to World Travel & Tourism Council, in 2025 travel is expected to contribute an all-time high of $11.7 Trillion to the global economy, a 7.3% growth since 2024. The global travel industry has seen a better growth rate than the $AMZN stock over the last year. (6.5% growth over the last year and this is not investment advice)

We have all made restaurant reservations through Opentable, booked a flight through Kayak, a place to stay with Booking.com or found great deals at Priceline, these brands along with Agoda and Rentalcars make up what is now known as Booking Holdings, previously known as Priceline Group.

Glenn has been at the company for 25 years, started out leading corp dev and has now been CEO for almost 9 years. When he joined the company in 2000, it was in the middle of the dot com crash and the company was at it’s lowest with a market cap of $0.25B at the end of the year. He has been there for the dot com crash, the global financial crisis of 2008/09 and COVID. Since Glenn took over as CEO in 2017, both the market cap ($72B - $160B) and revenue ($12.6B - $23.8B) have roughly doubled. Founding history: Booking was known as Priceline Group until 2018. Priceline was founded back in 1997 by Jay Walker with a “name your own price” model for hotels, flights, car rentals etc and went public on NASDAQ in 1999. Many might not know this, but Priceline was spun out of Walker Digital which was sort of a venture studio/IP research lab that Jay founded in 1994 and ran out of Stamford Connecticut. Glenn led the charge on acquiring Booking (a Netherlands based company) way back in 2005 for $133m. Accommodation bookings now account for more than 85% of total Booking Holdings revenue which back in the day was a smaller subsidiary of then Priceline Group. He credits his prior career in investment banking to preparing him for the M&A role at Booking, where he saw a lot of deals not be successful for the acquirer.

Interestingly, Expedia was also started around the same time, in 1996 (their market cap is around $27B). One thing Booking has done really well is growing all brands independently with different CEOs post acquisition. It is interesting how they have managed to successfully operate under a more decentralized management structure.

Glenn is incredibly candid and a joy to talk to, we tee it off by talking about history. Hope you enjoy!

Timestamps:

00:00 - Introduction00:15 - Getting into world history08:19 - Peter Thiel on Rise and Fall of empires11:34 - The India-Pakistan partition19:45 - Glenn Interviews Suffiyan28:05 - Groundbreaking programs from the past32:27 - The start if Glenn’s career at booking35:57 - How Glenn thinks about acquisitions41:48 - Acquiring Expedia? What went right for Booking51:59 - Current issues in travel that are billion dollar business opportunities57:27 - Leadership and training talent1:05:58 - Passing down the torch 1:10:53 - The best use of the CEO’s time1:18:52 - Importance of storytelling 1:26:47 - Important of decision making and compounding1:32:26 - Changing how airports operate and speed of travel1:36:40 - Advice to younger audiences and the state of schooling1:42:24 - Leaders Glenn admires1:45:44 - Rapid fire ending

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Around 11,000 Americans are retiring every single day, ~60m people in the US are retired. Medicare is one of the biggest problems among this community, there are 100s of providers and choosing the wrong one could either mean losing thousands of dollars or your life (I think Cobi quoted a report citing ~20% fatality on choosing the wrong provider). If your parents are not in that age group yet, you probably haven’t started thinking about this but it is one of the biggest and most underserved markets in the US.

The opportunity is not to just help senior citizens with Medicare, the opportunity is to redefine what retirement means for people over the age of 65. My maternal grandfather retired at the age of 82 and was one of the healthiest and fittest people up until then. Your health cannot be wholly defined by your diet and exercise routine, purpose in life plays an equal if not one might argue a bigger role. In my day job I work with Tim Draper, his dad Bill Draper who I met a couple of years ago was going to office twice a week at 95 years of age. Charlie Munger did the Berkshire Annual Shareholder meeting with Warren Buffett at 99.

If you can figure out a way to give purpose to people over 65 and activate them that is ~23% of the US population by 2050. What impact could that have on the GDP? I will leave that for you to imagine. You probably have an uncle, grandparents or parents where you can see the difference between the ones who hang up their boots and the ones who never retire. There is something about the keeping your brain active which is more meaningful in many ways then even your diet or gym routine. In our last episode we had Colin Greenspon on the show who started Narya Capital with Vice President JD Vance. Narya is an early investor in Chapter, cofounded by Cobi Blumenfeld-Gantz and Vivek Ramaswamy. JD Vance and Peter Thiel were on the board of the company and maybe that is why the company is widely misunderstood or MAGA labelled, hear from the CEO Cobi on the masterplan of Chapter to redefine what retirement means in the long term. My conversation with Cobi is his first ever long form podcast and it is one of the best ones I have recorded so far. He was incredibly candid and insightful as we got to dive into his time at Palantir where he spent 5 years, why he chose to go after the ~60m seniors (aged above 65) in the US to make Medicare easier for them, utility of AI in its current state, recruiting and some common myths in business.

Hope you enjoy!

In case you missed my conversation with Colin, you can catch up below. It was a pure masterclass on thesis driven investing and was Colin’s first ever long form podcast.

Timestamps

00:00 – Intro02:38 – Why Chapter is Misunderstood?5:48 - What Chapter is doing?8:14– Why founder market fit is a joke09:13 - What does Palantir actually do?12:31 - Building Conviction 16:50 - What are tech enabled service businesses21:08 - Recruiting without bias 27:12 - AI in Chapter and Building a lean team32:33 - Allocating time as a CEO37:53 - Building Culture and interviewing50:29 - Choices that compound 57:55 - Casting at Palantir & Alternate career choices1:03:41 - China vs US1:13:12 - Has innovation stagnated?1:15:52 - Chapter’s business model innovation1:23:41 - Zero To One-isms1:31:05 - Helpful mentors in life1:36:37 - What does a business plan mean for early stage companies?1:39:54 - Other problems to solve1:46:27 - Rapid fire and signing off

Watch on YouTube

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wethebuilders.us