Uber

Tusk Ventures: turn regulatory consulting into equity in Uber and Airbnb

Shaan profiles Bradley Tusk, an ex-policy operator who helped Uber fight taxi cartels and city regulators, then took equity that became one of the decade's best angel returns. He repeated it with Airbnb and built a $100M services firm paired with a venture arm.

“And then he got to invest and Uber was like one of the best investments of the decade for an angel investor. And he did that also with Airbnb, another group that had policy questions. And so any startup that had a regulatory or policy challenge, which actually many do, uh, it was like, oh, we should include Tusk in our round.”

Why Gary passed on Uber twice: 'defense always loses'

Gary explains he passed on investing in Uber twice because it looked like Garrett and Travis's side hustle rather than their main focus — a lesson that he had played too conservatively until 35 and that 'defense always loses.'

“What I learned there was defense always loses. I bought my first apartment in Manhattan. I played so conservative up until 35.”

Invest only on the jockey: 'Is this person one of us?'

After missing Uber by judging the idea rather than the founders, Gary flipped to investing almost purely on the person — he'd have to hate the idea to pass on a founder he sees as 'one of us,' because great operators will their way to success even after pivoting.

“I am now completely infatuated with investing only based on the person. I have to hate, that would be the word I use, and I don't like that word. I would have to hate the person's idea to not go if I think that the jockey is a gangster, and it's worked out for me.”

Steal thisBet on the operator, not the idea — the right founder will pivot their way to a winner.

The double-the-price playbook for engineer-led businesses

Sam relays a tactic he learned from Terry: engineer-led software businesses are typically priced too low, so doubling the price often doubles revenue. Then mine the customer email domains to spot companies with many users and upsell them enterprise plans.

“she was like, look, the whole thing is that engineer-led businesses typically are priced poorly, and if you just double the price, uh, it works, right? And she was like, double the price and then find out which emails URLs are being used a bunch of times. So for example, if you have like 18 people using @uber.com, contact the HR department or whoever, the procurement, and like sell enterprise.”

Steal thisBuy an engineer-run SaaS, double the price, and mine shared email domains to upsell enterprise seats.

Mike Maples' inflections: bet on what becomes possible in 10 years

Sam relays Mike Maples' early-stage framework: you can't predict winners, so look for inflections that will make new things possible in 10 years and invest ahead of them. Uber's inflection was every phone getting GPS.

“So I try to use some frameworks and I just basically think like, you know, what interesting things, what interesting inflections are going to happen in 10 years that's going to make X, Y, and Z possible, but it's not possible right now. And I'm going to try and get into it. So like, for example, Uh, Uber, what made it possible was everyone started having really great phones that had GPS in it.”

Steal thisInvest ahead of inflections — find what a coming shift makes newly possible, then get in before it's obvious.

The sharing economy basically only works for Uber and Airbnb

Sam argues from looking at the data that the sharing economy realistically only works for ride-hailing and home rentals, and maybe nothing else. Sharing tools, cooking lessons, or garage storage repeatedly fail because the inconvenience isn't worth the money.

“I am almost positive that the sharing economy only works for like 2 or 3 things: Uber and driving, um, Airbnb home rentals, and maybe that's it.”

SF vacant office space tripled to 10M sq ft; rents cut to $20

Shaan cites a CNBC article: sub-leasable San Francisco office space jumped from 3M sq ft in 2019 to 10M in 2021, with ~$200M of real estate impairments (nearly $1B with lease write-downs across Salesforce, Dropbox, Uber, PayPal, Zendesk). Space that cost $90/sq ft is going for $20.

“So like, here's some of the numbers. Um, let me, so there's $200 million of real estate impairments in the past year since COVID It's almost a billion if you add in the lease-related write-downs from large companies like Salesforce, Dropbox, Uber, PayPal, Zendesk, just getting rid of their, their real estate. And so Dropbox itself has $400 million of impaired real estate right now.”

Hire the operator who opened a market for a category leader

Shaan's repeated playbook: when a business is purely an operations problem, recruit someone who launched a city or country for Uber (or a similar leader). He's backed multiple companies whose founding teams included an 'I opened up Uber in Canada' type operator.

“Yeah, you go find the guy who opened up Uber's like Atlanta business and you're like, hey, I I need you. You are an operational person. I need you to come here and solve this problem. Which, by the way, I think I've invested in 4 companies and on the founding team of each of them was like, I opened up Uber in Canada. I ran Uber's Canada business. I went there first to open it. I became the GM.”

Steal thisWhen the bottleneck is execution, recruit the person who launched a city or country for a category-leading operator like Uber.

The law of increasing returns: build a positive flywheel

Shaan's core investing filter is whether a business has a positive flywheel where each new user makes it more valuable to everyone else, citing Amazon (selection, price, delivery), Facebook, and Uber. He contrasts this with e-commerce, where every new dollar requires equal or more work.

“It's this one theory, which is, does it have a positive flywheel? Which means the more people who use it and the longer it's around, does it become more and more valuable? There's something called the law of increasing returns. And so I want to be in a business that's like that.”

Steal thisPick businesses where each new user or merchant makes the product more valuable to everyone else, so momentum compounds instead of resetting.

Build the biggest farm in America by going city to city, Uber-style

Furqan reframes vertical farming as a direct-to-consumer land grab: a vertical farm is a machine that produces fruit and lettuce, so instead of buying farmland you put a small farm near each city and expand city by city like Uber to become the biggest farm in America.

“Well, if you can produce the fruit yourself, like you just have a machine that can produce fruit, that's the vertical farm. Well, why don't you become the biggest farm in America really quickly by kind of going city to city and kind of doing that? And you've seen Uber do that. You've seen kind of all of these other, right? You could literally invent, kind of build the biggest farm in America now, right?”

Steal thisTreat a vertical farm as a deployable machine and roll it out city by city, building a national D2C produce brand without owning farmland.

Uber for global relocation: pick up stakes and move countries instantly

Balaji predicts permanent international migration and digital nomadism will be huge, calling it an underappreciated area with a thousand pieces of tooling to build. The next step beyond Uber-to-the-coffee-shop is 'Uber around the world' to relocate internationally as fast and cheaply as possible.

“I think an underappreciated area is going to be relocation, permanent international migration. You know, this is why I did Teleport a while back. Digital nomadism is going to be huge. Uh, being like, there's a thousand pieces of the tool chain for allowing people to go more mobile. You know, Uber and Airbnb— Uber is go down, you know, to the coffee shop, but the next step is Uber around the world.”

Steal thisBuild tooling for frictionless international relocation; treat moving countries like calling an Uber.

The investing Ikigai: curiosity, network, fundamentals

Ryan Begelman says his best returns over ~60 angel/real estate deals came at the intersection of what he's genuinely curious about, where he's well networked, and where fundamentals are strong. His healthcare bets (good fundamentals, no curiosity or network) underperformed his Coinbase, Warby Parker, and Uber bets.

“the ones that generally perform well are the ones that are at the intersection of what I'm naturally curious about, where I'm well networked, and where there's good fundamentals. So it's a similar like Ikigai concept where— and so my main, my main filter for, for making investments now is is this something I'm actually sincerely fascinated by? I'm regularly reading about and I'm well networked in.”

Steal thisOnly make investments that sit at the intersection of genuine curiosity, an unfair network advantage, and strong fundamentals.

Your network gets you IN, not value-add after

Both Shaan and Ryan argue the investor 'value-add' after a deal is mostly a load of shit. Ryan reframes network as access: he got into Uber early because of his network, and missed early SpaceX because he wasn't networked there yet.

“I'm saying I got in early to say Uber because of the network. Because of my network. Yeah. And I can't get in early. Like I tried getting in early, you know, to say like, uh, SpaceX, like I wasn't well networked then. Now I became better networked around SpaceX later and I ended up investing later, but like there's certain areas where I have an unfair advantage to getting investments.”

Steal thisUse your network to get into great deals early, not to add value afterward.

Calacanis's Uber stake peaked at 4,000-5,000x

Calacanis says his Uber angel investment was worth as much as 4,000x to 5,000x at peak depending on exit timing, and he still holds roughly half his position.

“the Uber investment, uh, wound up being— I mean, at its peak, maybe 4,000x, 5,000x, depending on when, you know, you choose to sell it. And I still own, I think, around half my position, so I'm still long Uber.”

The Uber engineer who lived on $3 of food a week

Shaan tells of Jeff, an Uber engineer making great money who lived on $3/week of food by eating free office meals, walking everywhere to avoid expenses, and treating himself to a $3 Costco chicken bake on Sundays, singularly obsessed with becoming a billionaire.

“So Jeff, uh, used to spend $3 a week on food, and I was like, how's that possible? And he was like, well, you know, I work at Uber, it provides— they provide, you know, like a lunch and kind of dinner service, and they have snacks, so that's breakfast.”

The Penny Hoarder: a personal-finance blog that became a $50M affiliate machine

Sam recounts how founder Kyle started The Penny Hoarder as a broke college kid blogging about odd jobs, noticed Uber paid $2,000 per driver referral, and built it into a $50M/year content-plus-performance-marketing business by optimizing articles to drive affiliate signups.

“He started it as a finance blog where basically he was like a poor 20-year-old and he was doing like TaskRabbit and Uber driving and all types of odd jobs in order to make ends meet while he was in college because he came from a low-income household. He would blog about it. Eventually, this is his origin story. I don't know if it's true. He was like, "Oh, wow. Uber will pay me $2,000 for every person I refer to them. I'm going to write a little bit more about this and put more affiliate links." That's what he did.”

Better AND cheaper means zero product-market-fit risk

Shaan refines the framework: Uber won because it was better and cheaper than a cab, which removes product-market-fit risk. Being better-but-pricier (Boom supersonic jets) or cheaper-but-not-better still leaves demand risk.

“Whereas the trick with like something like an Uber, for example, Uber was way more convenient and it was cheaper than a cab. And so that's better and cheaper. Better and cheaper is when you have zero product-market fit risk. Um, but if you're better but more expensive, or you're cheaper but not better, then you still have the product- benefit risk and you shouldn't miss out on that.”

Steal thisOnly assume demand is guaranteed when your offer is simultaneously better and cheaper than the incumbent.

Sacca's Lowercase fund returned 225x: $100K became $22M

Shaan notes a great VC fund returns ~5x and Sequoia's top funds maybe 9-10x, but Chris Sacca's Lowercase Capital (Uber, Instagram, Twitter, Docker) returned over 225x, meaning $100K in became $22 million out.

“So this one returned over 225x. So, like, you know, you put in $100K, you got $22 million out.”

Pay early network contributors in tokens, not dollars

Askren pitches Rokfin's model: pay creators (or, hypothetically, the first Uber drivers) in tokens they can cash for dollars same-day or hold. Since the first members create far more network value than the millionth, early holders could end up with tokens worth millions.

“If the first Uber drivers were paid in tokens, not in dollars, right? That day they can cash out their tokens if they want for dollars. But if they say, hey, this Uber thing, I think this Uber thing is going to be something, I'm going to, I'm going to save 20% of all my tokens. Because in any digital network, the first people in the network provides way more value than the millionth person in the network.”

Steal thisTo bootstrap a network, reward early contributors with equity-like tokens that grow with the platform's value.

The Uber referral arbitrage: 30-cent rides, $10 credits

Abhishek explains his core scheme: Uber paid referral bonuses scaled to local currency, but rides in India cost only ~30-50 cents, so each cheap ride generated a $10 US referral credit he could resell.

“Uh, it's a basic arbitrage. Like arbitrage in India? Yeah, arbitrage. In, in US they used to give like $10, $20 referral value. In India they used to give ₹100, ₹200, ₹300 in rupees. And in India one ride cost, it starts from ₹50 also, ₹50 or ₹25. If you convert it to dollars, it will be like 30 cents, 40 cents, 50 cents max. So we are taking rides using that 50 cents, and in turn, Uber is giving us $10 in US.”

Steal thisHunt for systems that price incentives in one currency or geography while costs sit in a much cheaper one, then arbitrage the gap.

He hired managers to run squads of kids taking Uber rides

To manufacture an endless supply of new-rider referrals, Abhishek paid people to manage kids who would create burner accounts (India only needed a phone number, no credit card) and take cheap rides to trigger referral bonuses.

“I have a few people who work for me, kind of, and they manage those kids. Like, they sign up many accounts from there because in India Uber doesn't require credit cards. In US they require. So India, you just need to have a number to create an account. So few people, they create account so that other people, other kids, they take ride and you get referral bonus.”

The Maldives trick: set country to where Uber doesn't operate

When US referral values dropped to $5, Abhishek discovered that setting an account's country to a place Uber didn't operate defaulted the referral value back to $10. After Sri Lanka got Uber service, he switched buyers to the Maldives.

“Yeah, so somewhere where Uber is not running. So initially we tried Sri Lanka, but after that they are like— Uber is operating in Sri Lanka also. Then in Sri Lanka, refer value is set to Sri Lankan value, like some 100 rupees or something, Sri Lankan value. Then we found Maldives, and then any other country you can set where Uber is not there, Uber is not operating, then it was setting default value to $10, but $10 is good value for everyone to buy, so they were buying.”

Uber-credit hustle peaked at $20K/month

Abhishek's referral-credit reselling business hit $20,000 a month in revenue at its peak, while his apartment in India cost about $350/month.

“$350 US dollars. And you at your peak were doing $20K a month.”

Don't wait until you're rich — think of yourself as an investor on day one

Shaan's biggest angel-investing lesson: the excuse 'I don't have capital' is false. If you're resourceful and persuasive enough, you can access other people's capital, so start treating yourself as an investor immediately rather than waiting to be wealthy.

“the number one advice I would give to you is don't wait until you're rich to do it. Because at that point, you know, the financial returns, it will just be a part of a broader portfolio. It's not going to be that exciting. But if you really want to do this, start thinking of yourself as an investor from day one and find ways to access the capital.”

Steal thisDecide you're an investor before you have money, then go source capital from people who want deal flow.

The investor who passed on Uber's seed round

Greg recounts a very smart NYC friend whom Garrett Camp pitched on Uber's seed round. The friend dismissed it — in Manhattan you just raise your hand and a car comes — missing that Uber was a 10x better product elsewhere.

“Garrett pitched him on the seed round of Uber, and this is in Manhattan. He was just like, "Garrett, I don't know what you're thinking about, man. People aren't going to press a button and a car is going to come. It's just, you raise your hand. Look at me." He raises his hand, a car comes.”

Local marketplaces win on supply-demand density, not features

Sam explains that the hard part of local on-demand businesses (Nana, Uber, dating apps) is bootstrapping both supply and demand city by city. The winners aren't the ones with the best product but the ones who get enough of both sides into one geography at once.

“And, um, the dating apps that win aren't ones that make you a better dater. They're ones that figure out how to get a bunch of guys and girls in one city on the app at the same time.”

Steal thisFor any local marketplace, solve liquidity one city at a time before worrying about features.

Make a mortgage refi a 10-minute online flow

Shaan pitches an idea born from his own painful refinance: a product that shows your current rate vs. a cheaper market rate and lets you refinance in 10 minutes online. He says he'd invest in whoever builds it.

“But it should be as simple as, hey, here's your current rate, here's the rate you can get on the market that's cheaper. If you'd like to refi, 10 minutes and you're done. That's how it should be.”

Steal thisCompress a painful, paperwork-heavy financial process like a mortgage refi into a rate-comparison plus 10-minute online checkout.

The Penny Hoarder: $0 to $60M bootstrapped on affiliate blogging

Sam tells how Kyle Taylor blogged about side hustles he tried when broke (driving Uber, surveys, coupons), earning affiliate fees like $2,000 per Uber driver referral, and scaled The Penny Hoarder from zero to $60 million in sales, fully bootstrapped, in about six years.

“anytime someone saw an article that he wrote about driving for Uber, he would make $2,000 per Uber driver. And so he was like, oh, this is cool. I should— I'm going to blog about all the ways in which I can save money or make extra money.”

Full-time Uber drivers earn ~$36,525/yr, near $3/hr after costs

Stu cites that average US Uber pay is $8.55-$11.77/hr, roughly $36,525 a year for a full-time driver, and once expenses and idle time are accounted for it nets closer to minimum wage, a figure they round to about $3/hr.

“In America, the average full-time for a driver, full year, $36,525 a year. $3 an hour, right? That's minimum wage.”

Turn Uber rides into a targeted in-car music promotion network

Stu pitches using millions of daily rides as audio inventory: partner with Uber and music labels to play new artists' songs to a micro-targeted captive audience during that critical first viral week, paying the driver to run the station. Non-invasive because it's just music, not ads.

“a music label wants to get their new artist, someone that they've invested in, in front of the right consumer, especially in that first week where they want songs to hit that kind of viral effect. Right. And so if you were able to build a music platform to partner with labels and Uber to actually serve direct music towards a very targeted audience, and you could make money by playing that song, right, I think it'd be a great business.”

Steal thisTreat idle in-car rides as targeted audio inventory: pay drivers to stream label-promoted new music to riders.

Shaan got an Airbnb offer rescinded for lying about his criminal record

Shaan got early job offers at Uber and Airbnb (first ~100 employees); one offer was rescinded after he lied on his resume about having a criminal record, and he was told not to come to work on Monday after already moving out for the job.

“I had job interviews at Airbnb and Uber early-ish, first 100 people. And, uh, one of them I got employed, one of them I got the offer, but then they rescinded it because I lied about my resume. And the other one I didn't get past the What did you lie about? I had a criminal record and I told them I didn't. Okay, so I moved all the way out here. I moved all the way out here and they're like, oh, all right, uh, don't come to work on Monday.”

Cheaper Uber rides tripled the SF taxi market, not shrank it

Chicola uses Uber as a parallel to AI transcription: even though the price of a ride dropped, the personal-transport market in SF got much bigger because every millennial heading to the bar now takes a $7 Uber Pool, an option that didn't exist before.

“The other example I would say is, look, how big was the taxi market in SF? You know, circa 10 years ago, right? It's a lot bigger now. The market for personal transport is so much bigger, even though the price has gotten lower. How can that be? Well, now every millennial who's thinking of going to the bar is probably going to use an Uber Pool and pay like $7, whereas before, there was no option.”

Uber 3x'd the size of the SF taxi market in a single year

Shaan recalls the bear case that Uber was overvalued because even owning 100% of the taxi market wouldn't justify it — but in cities like San Francisco, Uber tripled the total size of the taxi market in the same year.

“Well, even if it took 100% of the taxi market, it wouldn't live up to this. What turned out was, in cities like San Francisco, that same year— I remember this when I read this argument— that same year, they 3x'd the total size of the San Francisco taxi market themselves.”

Belsky told Garrett Camp the black-car app was a distraction

StumbleUpon founder Garrett Camp showed Belsky sketches of an app for summoning a black car in his New York apartment. Belsky told him it was a textbook distraction; fortunately Camp ignored the advice and it became Uber.

“Literally showed me these sketches of this product where it's about summoning a black car as opposed to having to dial for it. And, um, and I'm like, dude, you should be focused on your business. You just bought it back, right?”

Why Uber chose an expensive, elite brand even while aiming for mass access

Belsky recalls the early Uber Cab debate over whether the brand should feel accessible to everyone or aspirational. Garrett Camp won the argument: make it feel like a superpower, everyone's private driver, hence the black, luxury identity.

“Should it be an expensive feeling brand where it looks like it's aspirational but something you couldn't afford, or should it be an accessible brand where it feels like this is something that everyone should be doing, right? And it was actually a really healthy argument because you intuitively think it should be accessible to everyone. I mean, if you want to make a big company, um, but Garrett's view is that it should be something that feels like a superpower, like everyone's private driver. It should feel expensive even though it was intended to be accessible.”

Steal thisMake a mass-market product feel like an exclusive superpower; aspirational branding can coexist with broad access.

A $200M deal vaporized by one Facebook algorithm change

Sam tells of a friend whose media company was about to sell for $200M last January; Facebook changed its algorithm and the company was out of business by March. He uses it as the cautionary tale for any business built on one platform, like Firefly on Uber/Lyft.

“I know a guy who had a company that was about to sell for $200 million. Last January, Facebook changed their algorithm, and it went out of business in March.”

Travis Kalanick allocated ~$500M to ghost kitchens

Sam notes that Uber founder Travis Kalanick allocated roughly $500 million toward building ghost/cloud kitchens through his new venture.

“Travis Kalanick raised a— well, I don't know if he raised it. He probably used his own money, but he allocated something like $500 million to creating ghost kitchens or services for ghost kitchens.”

Buying Uber rides for 20 cents on the dollar via AdWords

Sheel and Flexport CEO Ryan Petersen bonded over a growth hack: they advertised their Uber referral codes on Google AdWords, pocketing the $10 referral credit and effectively buying Uber rides for 20 cents on the dollar.

“So you were just advertising. We were just advertising our referral code on Google. And so we were buying Uber for 20 cents on the dollar.”

Chris Sacca: 'I've never felt richer than when I had $0 net worth'

Shaan recounts how Chris Sacca levered his way up to a paper $12 million, swung down to negative $4 million in a week, and clawed back — saying he never felt richer than when he climbed out of debt back to zero. He's now a billionaire with Uber, Instagram, and Kickstarter in his portfolio.

“And he has this great line, which you remind me of, which was, I've never felt richer than when I had $0 of net worth. Like when he got out of the debt and got back to zero, he's like, I've never felt richer.”

Behance sold for ~$150M, mostly bootstrapped

Scott Belsky built Behance through 5 years of bootstrapping (funded by selling notebooks and speaking at conferences), raised only $6-7M right before exit, and sold to Adobe for about $150 million.

“He sold that company for about $150 million, and when he sold it, it was mostly bootstrapped. He eventually, uh, raised a little bit of money, like $6 or $7 million, but they raised that money like right before they sold. So, they had built most of the business without funding. And he funded the company by selling notebooks and speaking at conferences.”

Travis Kalanick was ranked #2 in the world at Wii Tennis while running Uber

Chris Sacca tells how, while CEO of Uber, Travis Kalanick hustled Sacca's dad at Wii Tennis — playing left-handed, then switching hands ('I'm not actually right-handed') — and was ranked #2 globally. Sam uses it to show competition is Kalanick's fuel.

“And later in that story, Chris actually says that he did the same thing with Angry Birds. He was ranked really high with that. But this is just how he's always been.”

Behance was funded by selling paper Action Books

Before Behance was a software platform, Belsky bootstrapped it by making physical 'Action Books' — paper organizers for creatives. Giving one to Garrett Camp is literally how the Uber pitch came his way.

“so we were bootstrapping our business, Behance, early days with paper products of all things. We were making paper products for creatives to be organized. They were like actual paper. And they're called Action Books. They're actually still out there.”

Why Uber chose to feel expensive even though it was for everyone

Belsky recalls debating Garrett Camp on Uber's brand: accessible-for-everyone vs. aspirational-but-expensive. Camp insisted it should feel like a superpower — 'everyone's private driver' — which drove the black, luxury identity. Belsky agrees it was the right call.

“But Garrett's view is that it should be something that feels like a superpower, like everyone's private driver. It should feel expensive even though it was intended to be accessible. And so that was part of the, you know, part of the thought behind the black kind of logo and the brand identity that like sort of suggested that feeling. The luxury, elite feel. Exactly. So I remember that debate, and I think that was also the right choice.”