A strategy execution framework that launched 24 cities in a day: Woody Hartman of Lime

The best strategy execution framework in this episode started as one person driving to San Diego to prove a point. Woody Hartman took a two month city launch process, cut it to four weeks, and eventually got Lyft to a run rate of roughly eight market launches a week.

Hartman is COO at Lime, the micromobility company operating across 250 cities and 30 countries. Before that he spent six years at Lyft, the last four as VP of Operations, while the company went from $100,000 in annual revenue to over $3 billion. He was president and head of product at TeamSnap, and held strategy roles at Disney, Fox Interactive and McKinsey. In 2019 he summited Everest.

Hired for joy, not for transportation

Hartman's career has one consistent thread, and it is not mobility. It is creating joy for people, which took him through video games and Disney theme parks.

A Lyft co-founder found him because of that. The pitch was that this was a transportation company about more than getting from A to B, that it was about the experience in between, and that someone who came from Disney with a passion for creating joy could help build it.

Hartman's first reaction was that it sounded crazy. After more conversations he concluded the founder was entirely sincere, and joined as general manager for Los Angeles, Lyft's second market, as roughly the thirty fourth employee.

His reflection on the pattern is that it repeats. He came back to mobility at Lime because the product creates joy, and he notes that he has never seen anyone in a bad mood on an electric scooter.

Why they refused to hire from the competition

Michael asks the obvious question: why hire someone from theme parks rather than someone from Zipcar or Uber.

Hartman's answer generalizes well beyond his own case. In an early stage company in an early stage industry, there is very little experienced talent to draw on. So instead of taking the shortcut of asking who has done this work before, you have to identify the analogs and decide what actually matters in terms of skill, behavior and mindset.

At that moment nobody had meaningful experience in what Lyft was building. Lyft and Sidecar were the only companies pioneering peer to peer rideshare, while Uber had built its business on licensed black car drivers, which came with a fleet and chauffeur mindset that was fundamentally different.

His conclusion became policy. If you want to build something different, you have to get different people. Lyft rarely recruited from Uber, because culture was meant to be the differentiator and you cannot differentiate on culture while hiring the same people.

Try everything, then replant what blooms

Hartman joined a week before the Los Angeles launch, so the first phase was absorbing everything the two launchers knew while also being what he calls a smart generalist: unafraid to make real world observations, read the limited data available, and try things.

His framing of the risk calculus is the part worth keeping. At that size, the risk of getting something wrong is very low and the risk of not trying enough things is very high.

So they experimented constantly across driver onboarding, customer marketing, which parts of the city to cover, and how to negotiate with the city itself. His image is letting a million flowers bloom, seeing which bloom brightest, and then replanting those.

The San Diego gambit

Six to eight weeks in, Hartman felt he could see the playbook. Meanwhile the dedicated launch team was struggling with Seattle and Chicago, taking more than two months per city and failing to recruit enough drivers.

So he took one junior team member, drove to San Diego, and announced he would launch it in four weeks without hiring anyone locally, which had been the biggest bottleneck.

It worked. The COO relocated him to San Francisco as director of launch, with instructions to repeat it.

What followed is the escalation. Two months became four to six weeks. Then one launch a month, then two, then one a week. The capstone was what they called 24 launches in 24 hours, which Hartman is honest about as partly a public relations stunt and partly real: 24 markets prepared over about a three week lead time and launched simultaneously, at a peak run rate of roughly eight markets a week.

And then the playbook changed again. They stopped doing dedicated city launches entirely, because they could do it remotely without sending anyone.

The real problem was always supply

Hartman is clear that demand was never the hard part in rideshare, and his explanation is a useful corrective to how these stories usually get told.

The value proposition sold itself. Nobody wanted to use the word taxi, and internally they refused to think of themselves as one because the ambition was larger, but the underlying use case was an established business model consumers already understood. People knew they might take one to the airport or after drinking.

The difficulty was supply, made worse by their own success, because app-based hailing unlocked far more demand than had previously existed.

The innovation was therefore entirely operational. Finding the supply, working out how to communicate with it, and persuading people who would never have considered driving a taxi to drive strangers in their own car. That was simultaneously a marketing problem, a funnel problem and an operations problem, since every driver needed vehicle and safety validation.

Adaptability, and the humility underneath it

Asked how he stayed successful across six years of constant change, Hartman gives one word: adaptability.

But the more useful part is what he says it depends on. The key to adaptability is humility, meaning a willingness to say you do not know how to succeed at this, or cannot make this decision alone, or simply that you got something wrong and have learned from it.

His diagnosis of why people fail at this is sharp. Imposter syndrome makes people less vulnerable and less authentic, and pushes them to pretend they know the answers.

His own practice was explicit inventory. After a year or two he could say honestly that he had the institutional knowledge, understood the system and knew what drivers were thinking, and equally that he had never managed a team that size or run a budget that large. Naming the second half is what let him surround himself with people who had.

He credits McKinsey for that, though not for the technical skills. As a 22 year old you know nothing, including basic things about work culture like how long to work or how to write a late night email. His phrase for the training is being comfortable uncomfortable, and his framing is that you are literally an imposter twice over, an outsider inside McKinsey and then placed as an outsider inside a client. Getting comfortable with that discomfort is what lets you learn and be useful without being a know-it-all.

Culture as the second product

Hartman's insight about management is a direct extension of his interest in creating joy.

What he learned as he became a manager, and then a manager of a thousand people, is that the culture you create delivers joy as much as the product does, and often more directly.

Which is why he has deliberately chosen environments where he could amplify a strong culture rather than fight one. Lyft drew him because of what the founders embodied, and he notes that community was the company's most common word in its first three years.

The most personal illustration is one he built himself. While at Lyft he started an LGBT ultimate frisbee league that went from a few friends throwing a disc in a park to hundreds of people and one of the largest LGBT sporting organizations in a city with many long established ones.

His explanation of why it worked is the transferable part. People detect authenticity immediately, and a league built to serve his own ambition would never have spread by word of mouth. What he was actually doing was tapping a real personal motivation, having lived in San Francisco as a gay man for a decade without finding a community built on the values he wanted, and deciding to build it around a sport that welcomes newcomers easily.

Coaching by refusing to give advice

Hartman found being treated as a coach genuinely jarring, because when people started asking his advice two or three years into Lyft, he did not see himself that way.

His resolution is one worth borrowing: if people want this from you, assume the mantle and deliver as well as you can while staying honest about your limits.

The method comes from a coaching class in business school, where the lesson was that great coaches rarely give advice and instead guide people to their own answers. Hartman's reasoning for adopting it is intellectually honest. His experience is a narrow sample, and assuming what worked for him transfers to a different context is often a false parallel.

His opening question, when someone asks how to achieve what he has achieved, is to ask whether they are sure they want to. Defining what you actually want is the first step, and he points out that his own path is closed anyway, since Lyft will never be a 34 person company again. Once someone names what they actually care about, building culture, scaling a company, developing successors, the advice becomes possible.

Knowing when leaving is the right operational decision

Hartman's account of leaving Lyft is the most unusual thing in the episode, and it starts with a criticism of the current norm.

He thinks the culture of taking responsibility for a successful transition has faded, replaced by people simply departing and leaving others to work it out. He treated it seriously, partly for a reason he admits is self interested: having invested years in the company, the legacy of that work would only survive if the handover was effective.

The transition took years to plan. He recommended someone on his own team to succeed him, and also recommended a significant reorganization.

The insight underneath is the part I keep thinking about. Sometimes you have to leave for the organization to take its next step. Hartman concluded he had become a crutch supporting an organizational model that was no longer serving the company, and that there was no good next role for him inside it. So rather than let the company hold onto him and preserve an outdated structure, he told the CEO the company needed a serious reorganization and that his stepping back was the first move in making it possible.

Working for a CEO who used to have your job

At Lime, Hartman reports to a CEO who was previously a COO, which he says is unusual and enjoyable.

His observation about the pattern is accurate. CEOs rarely come from operations. They come from finance, or from product, or they founded the company without ever holding an executive functional role.

The risk this created was overlap, since two people who think the same way and bring the same skills is not a division of labor. He credits the CEO with being self aware about it and deliberately leaning into the non-operating half: corporate development, business development, finance, fundraising, and the external facing work, plus product and engineering.

The benefit is real when he needs to push back. Having someone across the table who understands operationally why something is difficult, and can look for a way to make it easier, is a different conversation.

Why micromobility could not ask forgiveness

This is one of the sharpest strategic contrasts on the show.

Micromobility was largely built by people from rideshare, who brought the ask forgiveness playbook with them. It did not work, for a structural reason.

Rideshare was asset light. Cities had little leverage, because people were driving their own unmarked cars with no central licensing. Micromobility is asset heavy. Put millions of dollars of vehicles on the street and a city can hire a truck, collect them, and impound them. Hartman says the companies all learned this the hard way after about twelve months.

His verdict on the outcome is the interesting part. Giving cities leverage forced micromobility to reach a position rideshare took far longer to get to, which is that this is a partnership rather than a fight, because transportation and cities are both trying to serve the same communities.

The concrete expression is equity zones. Cities require that a share of vehicles, in Lime's example around 25%, be deployed in lower income areas that may not be independently profitable, as a condition of serving the profitable ones. Hartman's assessment is that this made the industry mature faster and delivered on its mission sooner than it would have on its own.

The energy argument

Hartman's case for micromobility rests on a simple physical observation.

Energy is expensive and valuable wherever it comes from. Moving a 200 pound person in a multi-ton vehicle spends almost all of that energy moving the vehicle. Shifting those trips to a 60 pound vehicle is transformative regardless of the power source.

He extends it into an argument about ownership. Most people own one large vehicle with a 300 mile range and seating for five to eight, weighing thousands of pounds, used overwhelmingly for solo commutes of five to twenty miles, sized for the twice yearly trip to collect lumber or drive a carful of children.

That is what transportation as a service should fix. If you are only buying one car you buy the most versatile one. If you rent what each trip needs, you get the truck when you need a truck and a scooter when you need a scooter.

Growth through focus

Lime entered the downturn well positioned, having raised over $500 million in 2021 and held most of it.

The strategic choice that mattered was the year's theme: growth through focus. While competitors kept expanding into small long tail cities worldwide, Lime doubled down on the largest and most valuable markets.

His verdict is that it was right. Those markets proved far more profitable than an aggregation of thousands of smaller ones, and more sustainable across every dimension of the business.

The result was a year expected to be EBITDA positive, which he notes would be a first for micromobility and, in fact, a first for any mobility company, since neither Uber nor Lyft had delivered a full EBITDA positive year at that point. He is careful to correct the record when Michael upgrades this to free cash flow positive: that is further out, because capital expenditure is significant.

The following year's theme, Path to Sustainability, is a deliberate double meaning covering both environmental and financial sustainability.

The two bets that opened the gap

With competitors cutting staff and exiting markets, Hartman attributes the divergence to two decisions.

Bringing hardware in house. Most competitors use commodity vehicles from the same handful of manufacturers. Lime develops its own, and the effect is measurable. When they swap older vehicles for their newer generation, utilization and market share rise almost immediately, because people standing in front of several options pick the one that looks better, safer, more durable and faster.

Treating cities as the most important customer. This follows from the leverage point. Cities gatekeep the right to operate, so Lime invested in those relationships and now wins nearly all the top tier tenders it enters. Hartman credits this as the largest single factor in their global scale, which includes being one of the largest operators in Europe and the largest in the US and in Australia and New Zealand.

Scale then compounds through purchasing power, operational efficiency and standardized global playbooks.

The congestion argument, and a useful piece of history

On the criticism that scooters clutter sidewalks, Hartman makes two moves.

First, the proportion. It is easy to focus on the new thing, but if 95% of a city's surface is allocated to cars, complaining that scooters crowd the remaining 5% suggests the allocation is the problem. He points to cities converting parking and traffic lanes into protected bike lanes, which reduces congestion and, more importantly, improves safety. His point about why people ride on sidewalks is direct: they are afraid of cars, and reasonably so.

Second, and more persuasively, the timeline. Micromobility is roughly five or six years old. Look at photographs of the automobile industry five or six years in, in the 1920s or 1930s, and you find no lanes, no parking spaces, cars and horses moving in every direction and parking across building entrances. The order we now take for granted took decades of traffic law, training and painted infrastructure.

His expectation is that within five years most cities will have designated parking corrals on every block, and that today's tipped over scooter will look like a solved problem.

Fifteen days to build a different company in New York

Hartman's answer to the standing question is a genuinely remarkable operational story.

Two and a half years in, Lyft had launched every major US city except New York, which was essential and also where the taxi lobby was strongest. Nobody is a credible US mobility company without New York.

After months of work with the city they had a plan, hundreds of drivers recruited, and a press conference on the Tuesday announcing a Friday launch.

In the car back to the hotel, a co-founder took a call informing him that the mayor would have him jailed if the launch proceeded.

The founder's first instinct, which Hartman describes as admirably scrappy, was that going to jail would make excellent press for a company fighting on behalf of the community. They talked him out of it.

What replaced it was a request to Hartman: build an entirely different, fully licensed business in New York within a week or two. New systems, a new regulatory environment, and every recruited driver taken through the city's licensing process.

He flew his whole team to New York regardless of what they were working on, and after fifteen days of continuous work they launched a completely different business model, which Lyft still operates in New York alone.

Everest, and why the summit is the dangerous part

Hartman left Lyft, took a year, and climbed Everest, and his reason is more interesting than the achievement.

Six years at Lyft had become central to his identity, and he genuinely worried about an identity crisis on leaving. So he made a list of things that might give the next chapter meaning, and this is the one that worked.

His framing is that it is rarely the easy and comfortable things that give life meaning. Lyft was neither easy nor comfortable and meant a great deal. Everest was the same, including feeling endangered, exhausted and confronted with mortality, and produced a stronger sense of self.

Asked what you do at the summit, his answer is: you go down.

His correction of the popular understanding is worth quoting in substance. The summit is not the reason people climb. It is where you are most exhausted, most dehydrated, coldest and most exposed. You are not breathing deeply and having a transcendent experience, you are in survival mode, working out that you need one bar, half a litre of water and a photograph before descending.

His description of the sport is one operators will recognize: mountaineering suits neurotic people who are extremely disciplined, because success requires micromanaging those details at every step.

And the fact that reframes it entirely: 80 to 90% of mountaineering accidents, including deaths, happen on the way down. The hardest part begins when you reach the goal.

The 5 things I took away from this conversation

1. In a new industry, hire for the analog rather than the resume. Nobody had rideshare experience, so Lyft hired for mindset and used culture as the differentiator, deliberately not recruiting from the competitor. That is a defensible strategy in any category that does not exist yet, and it produced Hartman.

2. Early on, under-trying is the bigger risk. The formulation that the cost of being wrong is low and the cost of not trying enough is high is the clearest justification for rapid experimentation I have heard. It also has an expiry date, which is exactly why the playbook kept changing.

3. Sometimes leaving is the operational decision. Hartman concluded he had become a crutch holding an obsolete org structure in place, and that stepping back was the precondition for the reorganization the company needed. Very few executives are able to see themselves as the obstacle, let alone act on it.

4. Asset-heavy businesses cannot ask forgiveness. The contrast between rideshare and scooters is a clean lesson about leverage. When your assets sit on public property, the regulator can simply take them, which forces partnership. Worth checking which side of that line your business is on before importing anyone's playbook.

5. The hardest part starts at the summit. Both literally and as a management observation. Most failures happen after the goal is reached and attention relaxes, which applies to launches, acquisitions and product releases as much as to mountains.

FAQ

What does a good strategy execution framework look like for market launches? At Lyft it was continuous refinement of a repeatable playbook. A two month process became four to six weeks by removing the biggest bottleneck, local hiring, and then compressed to weekly launches and eventually 24 simultaneous ones. The final step was recognizing the playbook no longer required anyone on the ground at all.

How do you scale a startup business when nobody has done it before? Hire for mindset and analogous skills rather than direct experience, since the experience does not exist. Then experiment heavily while the cost of being wrong is low, keep what works, and rebuild the playbook whenever the constraint changes rather than defending the version that got you here.

Why can't micromobility use the rideshare regulatory playbook? Because the assets are visible and seizable. Rideshare was asset light, using unmarked private cars, so cities had little practical leverage. Scooters and bikes sit on public streets and can be impounded, which gives cities real power and pushes operators toward partnership, including obligations like serving lower income areas.

What are the COO role responsibilities when the CEO is a former COO? They require deliberate separation. At Lime the CEO leaned into corporate development, business development, finance, fundraising and the external facing work, plus product and engineering, leaving operations clearly with the COO. Hartman notes the upside is a CEO who genuinely understands why an operational request is expensive.

How should an executive plan their own succession? Over years rather than weeks, including identifying and developing a successor internally. Hartman also argues for the harder question: whether your continued presence is holding an outdated structure in place. In his case, stepping back was what allowed the company to reorganize.

Also mentioned

• Lime, its city partnerships, equity zones and in-house vehicle development
• Lyft, where Hartman built the city launch playbook and later the New York licensed model
• TeamSnap, the amateur sports platform where he was president and head of product
• McKinsey, which he credits for teaching him to be comfortable uncomfortable
• Bird and Spin, competitors cutting staff and exiting markets during the same period
• Protected bike lane programs in cities including Paris and Seattle
• Hartman's 2019 Everest summit, and the fact that most mountaineering deaths occur on the descent

Listen to the full episode

Woody Hartman on Between Two COO's

Between Two COO's is hosted by Michael Koenig. Subscribe on Apple Podcasts, Spotify, or wherever you listen.