Emil Michael on Negotiations, Uber and Building Through a Downturn

Former Uber chief business officer Emil Michael tells Harry Stebbings how his Harvard classmates and the early internet drew him into technology. After law school he worked with Hadi Partovi at Tellme Networks and advised other early companies. He later moved into investing and advising.

Michael credits mentor Bill Campbell with helping shape his leadership and opening doors. Campbell’s willingness to coach leaders at competing companies impressed him; Michael now tries to help entrepreneurs in a similar way.

At Tellme, Michael says the company raised around $150 million before the internet downturn, cut its workforce from about 300 to 100 and shifted from a consumer model to enterprise voice services. He recalls years of rebuilding customer by customer and reaching roughly $100 million in revenue before the Microsoft sale. These are his retrospective figures.

Although he began several levels below the founders, Michael says he felt responsible for the company and its people. He describes that sense of ownership as a source of resilience during the difficult years.

Michael recalls a roughly $300 million offer for Tellme and persuading Hadi Partovi to arrange a meeting with Steve Ballmer. After a weekend of negotiation, he says Microsoft offered $760 million plus cash, close to $800 million. He credits CEO Mike McCue for building the company and team; the transaction details are Michael’s account.

The sale let him pay off student loans and gave him confidence that financial success was possible. He says his later Uber proceeds gave him further security, allowing him to take investment risks while retaining a preference for determined founders.

As an operator, Michael puts the founder first, then the product and market; as an investor, he still starts with the founder but places more weight on the size of the market. He notes that companies often pivot, so the eventual product and market may differ from the initial plan.

His negotiation framework starts with preparation: understand the counterpart’s business, incentives, personal situation and alternatives. He tries to learn more than he reveals, using publicly available information and relationships to understand what matters across the table.

When the other side becomes emotional, Michael tries to absorb the reaction rather than mirror it. A break or a calmer exchange can reset the discussion. He views composure as a negotiating advantage, while recognizing that his approach may not work for everyone.

If a counterpart does not recognize another party’s leverage, he may use trusted contacts to communicate it outside the room. He describes this as a whole-of-deal approach: relationships and follow-through matter alongside the formal meeting.

He watches for signals of eagerness and perceived leverage, including who arranged a meeting and how people behave. These are cues to investigate rather than proof of anyone’s motives. He says emotional reactions can make it harder to negotiate well.

Michael calls the Uber China deal with Didi his hardest negotiation. He says rivalry, regulatory pressure and substantial spending made a resolution important, even though he recalls Travis Kalanick being reluctant to sell. His account of the negotiations is one participant’s perspective.

He describes building rapport with Didi’s Jean Liu through candid conversations about their competition, then working through complex cross-border terms. Michael believes the relationship and trust between them helped bring the deal together; the interview does not independently establish the other side’s motivations.

He says he brought the completed agreement to Kalanick after negotiations, citing the scale of Chinese competition and regulatory risk. The financial figures and judgments in his account reflect his former role at Uber and are not independently verified here.

Michael recalls Uber’s Saudi Public Investment Fund financing as a roughly $3.5 billion investment completed after about 60 days of meetings. He credits colleague Fraser Robinson along with himself. He says the funding strengthened Uber’s negotiating position with Didi in the summer of 2016.

Asked about a regretted deal, he names Uber’s acquisition of Otto. He says he opposed the complexity and differing incentives at the time, and that a later dispute with Google made the cost substantial. This is his retrospective assessment of a deal made while he was an Uber executive.

In the 2022 downturn, Michael says investors had moved from fear of missing out to being comfortable passing on deals. He predicts a sequence of structured rounds, down rounds and distressed sales over subsequent quarters. That is his forecast at the time, not an account of verified subsequent outcomes.

For founders, he advises monitoring net cash burn, accepting slower growth when needed to extend runway and setting attainable targets. His examples of reduced growth and spending are illustrative, and his prediction that investors would reward companies that met plans is a view of the then-current market.

He distinguishes structured financing from a down round and from a recapitalization. Terms can change the economic outcome even when the headline valuation looks unchanged. He cautions that such decisions can affect employee motivation and existing investors differently.

Michael says he has not seen pay-to-play financings work well in the examples he knows, while acknowledging there may be counterexamples. He describes those financings as a form of recapitalization, not the same thing as every down round.

Asked why he and Kalanick left Uber, Michael attributes the outcome to Benchmark and investor fear. He acknowledges mistakes by the leadership team but disputes the fairness of what followed. This is a contested, one-sided account by a participant with personal and financial interests; the other parties’ perspectives are not presented.

Michael recounts a disagreement with Benchmark’s Bill Gurley about fundraising and valuation in 2014, which he sees as evidence of excessive pessimism. His characterization of Gurley’s motives and recollection of the figures are his own; they are not independently established in the interview.

Stebbings asks whether Kalanick had lost team support. Michael acknowledges some loss of support but says Kalanick had agreed to a leave of absence before subsequent pressure to resign. His allegations about how that pressure occurred are disputed assertions from his perspective, not findings of fact.

Michael also disputes the stated basis for his own departure and says he would have advised a different response had he been involved in Kalanick’s meeting. The interview does not include the board’s account or resolve the competing claims.

Assessing successor Dara Khosrowshahi, Michael credits him with cultural cleanup and taking Uber public but criticizes talent retention, debt and financial performance as of 2022. The valuation comparisons and causes he asserts are his interpretation, not a neutral assessment or verified like-for-like analysis.

Michael argues that Uber lost an opportunity in food delivery and criticizes acquisitions including Careem and Postmates. He predicts write-downs and asserts different management would have performed better. These are contested forecasts and counterfactual claims from a former executive; the interview provides no independent valuation of the alternatives.

He sketches a hypothetical much larger combined rides, delivery and grocery business under different decisions. The tens-of-billions figures are his imagined valuations, not achieved results or evidence that the proposed outcomes were attainable.

After time with Coatue, Michael says he prefers operating to full-time venture investing. He appreciates the firm but finds it difficult to negotiate against founders with whom he empathizes. He continues to advise and invest, so his opinions about the industry carry relationships and interests.

He sees potential misalignment when early investors want to protect large paper gains while a company needs to take risks for its next stage. He suggests providing liquidity or considering limits on board tenure, while recognizing the incentive difference as structural rather than necessarily personal misconduct.

Michael praises investor David Wighton’s polite, contrarian questions as a useful board contribution: ask what would happen under a different scenario without simply frightening the founder. He says such questions can expose options before a financing, sale or pivot.

On the influx of capital into venture, he argues that more funding can let founders experiment and enter new markets. He also worries that crossover investors facing public-market losses may become less consistent in private markets. His assessment is tied to the late-2022 environment.

He praises several firms and criticizes Benchmark’s model, arguing that multistage investing may matter more if technology acquisitions become less frequent. This is his prediction and opinion; his public dispute with Benchmark is relevant to the criticism, and Stebbings challenges whether specialization can instead be a strength.

At 50, Michael says becoming a father changed his view of time and made his former 70-hour workweeks harder to imagine alongside family life. He associates very rapid startup growth with the capacity to devote unusual time and energy, while Stebbings argues older founders can bring steadier judgment. Neither claim is a rule for all parents or founders.

Michael hopes to mentor other entrepreneurs as Bill Campbell mentored him. He also describes public service under Defense Secretary Robert Gates and advocates technology companies supporting defense work. This is his political and professional view, not a settled conclusion.

He names The Art of War as a book that influenced his negotiating, especially the idea of leaving an opponent a path to exit. He applies that principle to business and, as a personal opinion, to geopolitical conflict.

Discussing Elon Musk and Twitter before the outcome was known to him, Michael assigns probabilities to several possible resolutions. The interview was published in October 2022 and his numbers were contemporaneous guesses, not facts or evidence of the eventual transaction.

His investment advice is to meet founders personally rather than rely entirely on someone else’s judgment. He also wishes Uber had moved earlier from an informal startup culture to clearer governance and management processes as its workforce expanded.

He says his SPAC experience taught him that financial engineering differs from the dealmaking he enjoys. His prediction that many SPACs would unwind over the following 18 months was a late-2022 forecast, not a measured outcome in the interview.

Looking toward 2027, Michael says he wants to lead an important venture again, whether by founding, buying or operating a business. He expects to continue angel investing and advising, but does not plan to return to venture as a full-time partner. The host thanks him and closes the interview.