Apr 8, 2024 · 1h 8m · news
Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this engaging episode of 20VC, Postmates co-founder Bastian Lehmann shares the inside story of his company's massive $5 billion acquisition by Uber, critiques the standard venture capital playbook, and outlines his new entrepreneurial journey and provocative predictions for the future of AI hardware.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 18.6% of the talking time here. How this is scored →
Harry as informed peer 4.0 Guest teaching 4.4 Guest disagreement 3.6 Harry pushing back 3.3
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 57:10 Lehmann fiercely rejects Harry's incumbent dominance thesis
When Harry pushes back that big tech incumbents are too strong to usurp, Lehmann forcefully rejects the premise, pointing out Google's recent AI missteps and internal organizational cracks.
Hardest push from Harry ▶ 56:29 Harry calls out Lehmann's Blackberry/Grubhub comparisons as weakHarry directly rejects Lehmann's historical examples of fallen giants, arguing Microsoft's $350M daily free cash flow and data moats make current tech incumbents fundamentally different.
Biggest teaching moment ▶ 17:34 Lehmann corrects Harry's emergency deal framing using S-4 numbersLehmann corrects Harry's suggestion that Postmates was forced into an emergency sale, citing audited S-4 SEC filings showing $100M in cash reserves and impending profitability.
Harry holds his own ▶ 56:12 Harry challenges Lehmann with Microsoft's $350M daily cash flow metricHarry demonstrates deep market domain expertise by citing specific cash flow metrics ($350M/day for Microsoft) and data moats to push back against Lehmann's startup optimistic bias.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Welcome and Childhood in Germany | 2 | 1 | 1 | 1 | Harry opens with standard biographical questions about Lehmann's childhood and views on luck versus skill. Lehmann shares an extended story about early hacking and phone phreaking, while Harry keeps the tone conversational and humorous. | |
| Family Resilience and the Ambition to Succeed | 2 | 1 | 0 | 0 | Harry asks sensitive questions about Lehmann's parents' divorce and the origins of his drive. Lehmann reflects warmly on his mother working three jobs and his early ambition to support her financially. | |
| Running Postmates in Wartime Mode | 4 | 3 | 2 | 2 | Harry quotes an insider source describing Lehmann as a non-cuddly wartime CEO. Lehmann defends the high-intensity culture and explains why raising capital during competitive inflection points was rational. | |
| Defending the On-Demand Business Model | 6 | 6 | 5 | 6 | Harry explicitly pushes back on the viability of on-demand economics, citing low margins and high labor costs. Lehmann rejects the premise, explaining that scaled regional markets were profitable and contrasting real-world logistics with SaaS. | |
| The Backstory of the Uber Acquisition | 5 | 6 | 6 | 5 | Harry asks if Postmates was forced into an emergency deal due to running out of cash. Lehmann forcefully corrects this info war narrative using S-4 facts showing nearly $100M cash and impending profitability. | |
| How a $2.65 Billion Deal Became $5 Billion | 5 | 6 | 3 | 4 | Harry notes the reported $2.65B deal figure, allowing Lehmann to explain how negotiating with no collar turned the closing value into nearly $5B due to Uber's stock rise. Lehmann also shares Bryan Singerman's reaction. | |
| Acquisition Lessons and Dara Khosrowshahi | 3 | 4 | 2 | 2 | Harry asks what makes Dara Khosrowshahi an effective CEO. Lehmann gives a detailed breakdown of Khosrowshahi's trust-based leadership, risk taking, and media turnaround. | |
| The Fate of Postmates and Brand Integration | 4 | 4 | 4 | 4 | Harry brings up a tip that Uber wrote off Postmates, prompting Lehmann to clarify brand strategy in LA and offer to buy the domain back if true. Lehmann then pivots to second-time founder advantages. | |
| Partnering with Marc Andreessen and Tip Top | 3 | 3 | 2 | 3 | Harry asks how Lehmann selected Marc Andreessen for his new venture, Tip Top. Lehmann describes how Andreessen initiated the investment and discusses testing multiple startup hypotheses. | |
| Failure, Wealth, and Operating Without Ego | 4 | 5 | 3 | 4 | Harry presses Lehmann on how being wealthy changes a founder's hunger and decision-making. Lehmann reframes failure anxieties, noting the public forgets quickly and asserting humility in building. | |
| The Anticlimactic Payout and Lost Celebration | 2 | 4 | 1 | 1 | Harry asks how acquisition payouts actually hit a founder's bank account. Lehmann explains the lengthy DOJ/Shareworks pipeline and the sad anticlimax of COVID denying them a company celebration. | |
| Why 99% of VCs are Sheep | 5 | 6 | 7 | 4 | Harry asks about Lehmann's provocative tweets on VCs. Lehmann doubles down, calling 99% of VCs sheep in an echo chamber, and shares Brian Singerman's advice on why investors cannot change outcomes. | |
| Avoiding Skeptical Investors and Running Board Meetings | 4 | 5 | 4 | 3 | Harry asks why educating investors is a red flag. Lehmann warns that overly skeptical VCs often copy metrics to invest in competitors, and shares his strategy of using pre-meeting board dinners. | |
| Hot Take: The Rise of Inference Computers | 5 | 6 | 4 | 5 | Harry challenges Lehmann's thesis on home inference hardware versus cloud providers. Lehmann responds with arguments on latency, privacy, cost, and historical parallels to the early PC era. | |
| Hot Take: The Phone is Dead and Vision Pro | 4 | 5 | 7 | 4 | Lehmann takes strong contrarian positions, declaring the phone dead and calling Apple's Vision Pro a product in search of a market. Harry probes on replacement technologies. | |
| Why AI Startups Will Usurp Tech Incumbents | 7 | 6 | 7 | 7 | Harry directly calls Lehmann's Blackberry and Grubhub comparisons weak examples given big tech's $350M daily free cash flow. Lehmann fiercely pushes back, citing Google's AI PR missteps and Apple's internal cracks. | |
| OpenAI, Specialized Models, and the Deep Tech Frontier | 4 | 5 | 4 | 3 | Harry asks if Lehmann would buy OpenAI at a $90B valuation. Lehmann categorizes most AI market chatter as noise while highlighting specific embodied AI companies like Figure. | |
| The Imperative of Rapid AI Development | 3 | 3 | 3 | 2 | Harry concludes with a rapid-fire round covering tech accelerationism, United Airlines, and respected founder-CEOs. Lehmann emphasizes that not accelerating AI fast enough is humanity's primary risk. |
Statements from this episode (41)
Lehmann: Postmates had under $100M cash remaining before turning profitable
“We had just under a hundred million dollars left in cash, and our negative gross profit margin was, I think, single digits.”
Lehmann: Most companies fail because founders give up
“Most companies fail because the founders give up, and we refuse to give up.”
Lehmann rejects luck, attributing success to grit and hard work
“I don't really believe in luck much. But I also don't have a definite answer. I think I believe in determination and grit and hard work.”
Postmates raised approximately $900M in total venture funding
“And look, we raised quite a bit of money. I think we raised around nine hundred million.”
Lehmann: Major food delivery competitors had sound unit economics and profitability paths
“The fundamentals of, I think, the companies, and I can, I know this for us, but I have some insight in the other players. They were all pretty sound, and by that I mean there was a clear path to profitability. There was a clear understanding of unit economics,…”
Lehmann: Every scaled market was profitable for Postmates and DoorDash
“No, I think Tony and I knew from the start that, that this is a tremendous business. If you can scale it and every market that you had at scale was profitable for us, and I know that the same thing was also true for DoorDash.”
Peter Thiel and Brian Singerman were Postmates' only early backers
“When we started out, when Postmates started out, this thing sounded so crazy that the only people that wanted to give us money were Brian Singerman and Peter Thiel.”
Lehmann: Top VCs and hype cannot change startup outcomes
“A lot of times even the great VCs and a lot of hype can't really change the outcome of a company.”
Postmates and Uber held preliminary merger talks 18 months before deal
“A year and a half earlier, there were some preliminary discussions with the Uber team, so there was some familiarity.”
Postmates was market leader in California prior to Uber merger
“And with DoorDash being the, clearly the market leader in most of the U.S., but not in California and certain regions that That are very attractive. Where we were the number one.”
Lehmann: Postmates was preparing for an IPO prior to Uber acquisition
“As a matter of fact, we were planning to go public and would have probably been one of the last companies to do so before, ah, you know, the world ended.”
Lehmann: Postmates-Uber acquisition returned nearly $5B to shareholders
“We negotiated the deal so well, there was no color on the deal. By the time the deal closed, it was almost five billion dollars.”
Lehmann: Postmates prioritized deal structure over headline price in Uber merger
“And I think he came out with a number that was around 2.2 or something, and we negotiated it up a little bit, but I didn't want it to push too hard, because the two things that we negotiated for are no breakup, Absolutely no way out and no color on the deal be…”
Lehmann: Dara Khosrowshahi has made Uber his own
“And a for non-founder CEO, he really has, I think he has made this company his.”
Lehmann: Postmates acquisition has not been written off by Uber
“I see no signs of the Postmates acquisition being written off because I think the brand is very strong. It continues to be very strong in LA.”
Lehmann: Uber and Postmates planned shared backend tech with distinct front-end brands
“When we discussed the merger, we sort of had this idea that you leave these brands, you start uniting the tech underneath, and then at some point it's the same product, but it sort of has a, basically a different name. And that's literally like the one differe…”
Bastian Lehmann: Investing provides far less joy than actively building companies
“And so I try to do the investing thing and, you know, I do some investments, but it does not derive me the same amount of amount of joy than, Then actively building something.”
Andreessen Horowitz passed on Postmates four or five times
“I pitched him four times or five times the entire firm with Postmates. They were smart enough to say no”
Marc Andreessen committed to funding Bastian Lehmann over a single phone call
“He pinged me actually, because a friend told him that I was working on something and he called me and I said, I don't even know if that idea is good. And he said he said, okay, like, you, Are you, do you want to do it again? And I said, yes. It's like, well, t…”
Lehmann: Founders shouldn't fear failure because public attention moves on instantly
“The most important thing to realize is that it doesn't matter. We tend to take everything way too seriously. Like we, oh, if I fail, the world will think nobody cares. It takes a minute for everybody to get over it. Right? Something else will happen. Elon will…”
Lehmann: Postmates operated standalone for 8-9 months post-Uber acquisition signing
“After we signed the paper, because we had to run the company as a standalone company for, I believe eight, eight, nine months. So we had to hit our quarterly goals. We did not want it to have a scenario where we lose market share because now we're thinking tha…”
Bastian Lehmann: 99% of VCs are sheep who lack independent thinking
“I would probably today say that 99% are sheep.”
Lehmann: Founders Fund believes board seats offer all downside, no upside
“So at Founders Fund, they obviously believe in this very deeply. We just saw this obviously with Keys leaving there and being somewhere else, they, the belief is that there is very little you can do to actually move the needle, other than writing the check. An…”
Lehmann: Founders should walk away from VCs requiring deep convincing
“I do believe that there's unlimited amount of capital out there, and I believe that it is easier and it's better worth your time by focusing on the people that initially believe in that than trying to ride two or three rounds with the same VC firm and spend tw…”
Lehmann: Host board dinners before meetings to resolve tensions early
“What I found to be a very good strategy is to actually have the board meeting and non-board meeting and do a dinner the night before with a presentation sent out a week, but at least a few days ahead of time. At the board dinner, you discuss Any sort of tensio…”
Lehmann: High LLM compute costs prevent killer apps beyond chatbots
“I believe that one of the overlooked areas of the current state of AI and the large language models that we're using is that they're still very expensive. And as a result of that, they're dramatically more expensive than a Google search. And as a result of tha…”
Lehmann: Screenless dedicated AI inference computers will be in every home
“I think when it comes to AI and personal AI, we may be at a moment in time where there is an opportunity for a new computer, a new type of computer that we may see in every home. A computer that runs your own personal AI on a chip that does not have to be as p…”
Lehmann: Local home inference is the only cost-effective way for personal AI
“Inference is very powerful the closer it is to the source of data. I mean, given that you, if you think about a personal assistant, the personal assistant needs a lot of information about you and inputs, That's why you would see that at home. It also is the on…”
Lehmann: Apple is caught in the inventor's dilemma over AI
“I believe that AI happened too fast and Apple is caught in sort of the inventor's dilemma here.”
Lehmann: Smartphones have reached the peak of their societal importance
“So when I call it dead I don't call it dead in the sense of we won't use it anymore, but I think it has reached the peak of its importance in people's lives.”
Lehmann: Apple Vision Pro is a product in search of a market
“On the Vision, as it is, how it is today? I, short. I think it's a product in search of a market.”
Lehmann: AI startups created today will grow larger than tech incumbents
“There will be companies born today that will be larger in the field of AI. Then the companies that are the largest companies that we have today, and they will start as toys and they will start as something that is probably overlooked and something that is not …”
Stebbings: Microsoft generates $350 million per day in free cash flow
“We've never had incumbents who throw off three hundred and fifty million a day in free cash flow like Microsoft does”
Lehmann: Google went from most respected company to laughingstock over AI
“This is Google that you're talking about, and they shed the bed so hard. They literally just went from like the most respected company in the world to laughing stock in a matter of month.”
Lehmann: Apple Vision Pro will have record high returns and fail
“This will be the first product for Apple where they have more returns than they have on any other metric You. You can plot the graph, and it's since Steve Jobs came back, this is probably the first thing that is a turd.”
Bastian Lehmann: OpenAI may struggle to build successful products beyond ChatGPT
“It's a fantastic research company is how I would describe OpenAI. I think it remains to be seen if they can launch extremely successful products other than a chat based a chat GPT.”
Bastian Lehmann: Failing to develop AI rapidly poses humanity's greatest existential risk
“The risk is not that there will be an evil AI that will kill us. I think the risk will be that by not becoming more intelligent and using these intelligent tools will become extinct.”