Fall in Love With the Problem: Uri Levine on Product-Market Fit, Fundraising, and Firing Fast

The host summarizes Uri Levine’s career as ten co-founded companies, four still operating, twenty board seats, advice to fifty-plus startups, and two unicorns including Waze, sold for over a billion dollars. Levine confirms the outline and points to the through-line he has taken from all of it: fall in love with the problem. The lesson predates the book—he had worn the T-shirt for more than ten years before writing a book with that title two years ago. The host notes that the T-shirt and book title have become the clearest expression of Levine’s core startup advice.

Levine explains that the idea evolved over time rather than arriving in a single aha moment. Entrepreneurship is about value creation, and the simplest way to create value is to solve a problem. When founders fall in love with the problem, the problem becomes the North Star of the journey, reducing deviation from the course and making success more likely. It also makes the story more compelling: in 2007, saying “I’m building an AI crowdsource-based navigation system” was less interesting than saying “I’m going to help you avoid traffic jams.”

He advises founders to start with a big problem worth solving, then ask who has that problem. If you are the only person on the planet with the problem, he jokes, he can recommend a therapist rather than a startup. If many people have it, the next step is to speak with those people and understand their perception before building the solution. Starting with a solution risks building something nobody cares about; starting with a validated problem creates value if the solution works.

Levine says he receives many founder emails that begin with what the company is doing, and he does not care about that first. What matters is why the founder is doing it, what problem is being solved, and what value is created for the user. Stories that begin with “our company is” or “our AI system is” focus on the solution. Stories that begin with “the problem we are solving is” or “the value we create for you is” focus on the problem and the user, which are far better starting points.

When founders ask how many users to speak with, Levine says a hundred—not because a hundred is magic, but because it forces them out of their comfort zone and beyond close friends and family. In practice, speaking with twenty strangers can validate whether the problem is real. If people say “I know someone who has this problem,” it is not a real problem; if they say “no, the problem is…” and give their own description, that is a signal worth following. He notes the iPhone as a counterexample: sometimes a successful product creates a new behavior rather than solving an existing problem, but problem-solving remains the simplest path to value creation.

The host asks how important personal passion is when a problem is large but not exciting to the founder. Levine answers with emphasis: fall in love, because the journey is hard, complex, and long. Without passion, there is not enough internal drive to carry a founder through the hardship. The founder must personally fall in love with the problem, then engage everyone else to fall in love with the same problem and follow that leadership.

Levine offers Oversee as an example of a pivot. The company monitored airfare after a booking, because prices keep moving and travelers can rebook the same flight at a lower price after paying cancellation fees. It started as a B2C company, but users cared without taking the required action. The company shifted to corporates, where automatic rebooking could save about 10% of the travel budget and flow directly to the bottom line, making the B2B model successful.

When asked where startup ideas come from, Levine says his usually begin with personal frustration, such as hating traffic jams or hating to leave money on the table. The problem should start with something that genuinely bothers the founder and then be validated with many people. For B2B ideas, founders should speak with many businesses that appear to have the problem and understand their perception before proceeding. The pattern is consistent: start with a problem, validate it, and only then build.

Levine describes the startup journey as multi-dimensional, with at least three dimensions. The first is a roller coaster of ups and downs at a much higher frequency than in established businesses. He quotes Ben Horowitz, who, when asked whether he slept well as a startup CEO, said he slept like a baby—waking up every two hours and crying. The second dimension is failure: startups try things that do not work and keep trying until something does.

If the journey is a journey of failures, Levine draws two conclusions. First, if you are afraid to fail, you have already failed because you will not try; he cites Einstein’s line that failure comes from trying new things and Michael Jordan’s line about failing over and over. Second, you want to fail fast so you still have time for another attempt, another product version, another go-to-market approach, or another business model. More attempts increase the likelihood of success, like taking many half-court basketball shots rather than one.

The third dimension is length: the journey is longer than founders think, and the longest part is usually figuring out product-market fit. A corporate knows its value proposition, product, pricing, audience, sales motion, and execution plan; a startup has none of those and must discover them. If a startup does not figure out product-market fit, it dies. Levine defines product-market fit as creating value for customers, measured by retention: if users come back, value exists; if they do not, it does not. He notes that products like Google and Waze look essentially the same today as when users first encountered them, and cites Waze at four years, Microsoft at five, Netflix at ten, and ChatGPT at six years before most people heard of it.

Waze started in Israel, became successful there, and went global at the end of 2009 with the expectation that its crowdsourced model would work everywhere. It was not good enough in the U.S., Western Europe, Latin America, or Asia, and was good enough in only about four places: the Czech Republic, Slovakia, Latvia, and Ecuador. Drivers wanted Waze to succeed, but they churned when it was not good enough; Levine’s team spoke with them, built another version, and repeated that loop for more than a year until early 2011. Expansion then proceeded market by market—Los Angeles first in the U.S., Italy first in Europe, Colombia first in Latin America—though Japan never worked because its house numbering is chronological and crowdsourced partial data cannot reach “good enough” without every number.

Levine describes the early “all over the place” phase, when founders think about the problem, solution, ten-year vision, business model, and next year all at once. They must still execute one thing: figuring out product-market fit. Operational work such as building an organization still matters, but if product-market fit is not found, the company dies; if it is found, the company lives to fight another day. The next fights are growth and business model.

He argues that if a company creates value, it will eventually figure out a business model, at least with the people who receive that value. Figuring out the business model is itself a long roller coaster of failures. Waze initially planned to sell map data and traffic information, but ended up in advertising because selling to governments meant long sales cycles and did not fit a mobile-internet company. Growth is similarly constrained: word-of-mouth requires high frequency of use, because a tax-return product used once a year gives users only one annual opportunity to tell someone.

Each phase requires a different focus. In the product-market fit phase, a company does not need sales, business development, or even marketing because there is no product to sell; it needs product people and developers to iterate until the product is good enough. Once product-market fit is achieved and the product stops changing, the company shifts toward business model or scale, and marketing or go-to-market becomes the most important function. Levine says shifting gears is hard—some companies cannot find the clutch and get stuck in the previous phase.

Levine’s summary is that trying to do multiple things at once leads to failure, and “focus is not about what we are doing, it’s about what we are not doing.” If a product has high frequency of use, growth can come through word-of-mouth, so the company can prioritize growth and figure out the business model later. If frequency is low, the company is sentenced to acquire users for its lifetime, so it should figure out the business model first. The host notes Airbnb as a counterexample with low frequency but strong word-of-mouth; Levine adds that “coolness” can also drive telling others.

Waze raised about $50 million over its entire journey: a first round of $12 million, then $30 million, then a smaller final round. Levine says Israeli startups tend to be leaner than American startups, so they can raise less money, though often at lower valuations. Fundraising is a journey by itself and happens multiple times, unlike some startup challenges. If building a startup is a roller coaster, fundraising is a roller coaster in the dark—like Space Mountain—because founders do not know how to play the game at first.

Levine asked a leading Israeli VC how long it takes to decide whether to like an entrepreneur; the partner first offered the “right answer,” then the real one: “It’s before they sit down.” First impressions form in seconds, as on a date, and the rest of the meeting mostly confirms or complicates that initial reaction. Early-stage investors consistently told Levine they invest because they like the CEO and like the story. That leads to two conclusions: the CEO should go to the meeting alone so the spotlight is on them, and the CEO must tell a story that creates emotional engagement. Investors also need to believe the product is usable and that the founder can build it, so starting with the problem helps because investors are users too.

Levine warns that fundraising conversion is radically different from sales. In a mature company, about one-third of qualified listeners may buy, but with investors the rate is about 1%, so founders should expect a hundred nos for every yes. A venture capital partner may see 100 to 200 companies a year and invest in one or two. He calls the rejection process “the dance of 100 nos”: investors open the big book of excuses, and arguing after a no is useless, like arguing after a date has said no.

Most founders miss the most important slide, which is the first slide, the “Company XYZ intro” that stays on screen the longest while the founder has not yet said anything. That is where the strongest point belongs—market size, problem description, traction, or team. The second most important slide is the last one, the “thank you” slide, which is displayed while people chat and ask questions; it should repeat the strongest point instead of wasting the opportunity. Levine also recommends a public-speaking version with “one more story” as the last slide, and he illustrates why details matter with a microwave story: a CEO retold Levine’s microwave story verbatim to an investor because details make a story feel authentic.

Levine deliberately titled the chapter “firing and hiring” because firing is the hard decision and hiring is the easy one. He interviewed founders whose startups failed and asked what went wrong; about half said the team was not right, citing people who were not good enough or communication and ego-management issues. The scariest part was the next answer: nearly all of them knew within the first month that the team was not right. If they knew and did nothing, Levine argues, the problem was not the team—it was the CEO’s failure to make a hard decision.

In a small startup, hard decisions always rise to the top, and if the CEO avoids them, top performers leave because they do not want to work in a place unable to make hard decisions. Everyone knows when someone should not be there, whether because of underperformance or because they are toxic, and the CEO’s inaction damages the team. Levine’s tactical recommendation is to mark a calendar entry thirty days after every hire and ask: “Knowing what I know today, would I hire this person?” If yes, tell them they are exceeding expectations and give them more equity to buy loyalty; if no, fire them immediately because they are on a trajectory of failure and damage.

When a hard decision is clear but the CEO wants confirmation, Levine suggests asking top performers, “Assuming XYZ person is going to leave, how sore are you going to feel?” The answer is often “not a big deal,” which is the confirmation needed. The host connects this to Netflix’s “keeper test,” where managers ask whether they would fight to keep someone who announced they were leaving. Levine also describes a company with a good year that gave bonuses to nearly everyone except four people, and he asked whether those four were still employed—if they were that far below the bar, they should not be there.

Levine extends the same “knowing what I know today” question to life, including his adult children’s careers: if they do not like a job, identify what can change, revisit in 90 days, and quit if the situation remains. He also offers a simple reference-check question: “Would you hire him or her?” If the answer is yes, follow up with “Why didn’t you?” One reference offered a one-word email—“Take the guy”—and when asked for two words, said, “Take the guy fast.”

Levine tells a Steve Wozniak story: when Levine took a selfie using the iPhone volume button, Wozniak said, “Finally someone using it the way that I meant it to be.” The lesson is that there is no single right way to use a product; different people use products differently. With Waze, about 70% of an audience watches the screen, while 20% to 30% listens to audio prompts, and neither group necessarily knows or cares how the other behaves. But if a product builder does not know that users behave differently, they are building the wrong product.

The way to learn is to watch new users and, when they do something unexpected, ask them why; that “why” is what makes the next product version successful. Levine groups users by their willingness to adopt new behavior: about 2% are innovators who try new things because they are new, early adopters try when they see value, and the early majority is about one third of the population. Winning the early majority wins the market, but that group fears change, prefers the status quo, and worries about feeling stupid or embarrassed. The answer is simplicity—Leonardo da Vinci’s “simplicity is the ultimate sophistication”—and product teams should remove features that people are not using because they add complexity.

Levine describes a “funnel of use”: people download or visit, register, try the product for the first time, get value, and return. Most teams speak with users at the bottom of the funnel, the successful ones, but improvement requires speaking with those who failed—people who did not register, did not use, or did not come back. Those users know the “why” that a great product needs to address. Product owners are often innovators or early adopters, so they cannot intuitively understand the early majority without watching those users directly.

In the fail corner, Levine says he reserves the right to his biggest failure yet because he keeps trying new things and will eventually fail. He insists that failure is not something to fear: when people fail and get up, they get up stronger. His advice to parents is to teach children to fail, because children who are not afraid to fail will leave their comfort zone and discover what makes them happy. He cites the Japanese saying: fall seven times and get up eight.

Asked for books he recommends, Levine names Mark Randolph’s That Will Never Work and Atomic Habits. He notes that Randolph endorsed his book, and Levine reached out because he had heard “that will never work” more times than Randolph had. He also says his favorite recently discovered product is a chess app that got him playing chess against the computer again after many years. His life motto is simple: don’t be afraid to fail.

Levine says he will probably never be done starting companies; he has ten startups across multiple areas. One is Pontera, which helps people retire richer, and he points out that if you ask a hundred people with 401(k) plans what their plan is invested in, about 95% will say they do not know—they are often in whatever default applied when they joined. He also has a medical startup trying to create an “AI of medical knowledge” to improve doctors’ clinical decisions. Beyond those, he names mobility, medical services—U.S. medical services are five to ten times more expensive than Germany’s without being better—and education as areas still full of inefficiency; anything people still do the same way their parents did is probably worth revisiting.

Levine points listeners to the book on Amazon and Barnes & Noble and says LinkedIn is the network where he is most engaged. His email is in the book, and he answers all of his emails. He says he wants people to read the book rather than merely buy it, because his purpose in life is creating value and he believes the book is the best return on investment readers can make—not because of its price, but because of the time they will spend with it.