Keith Rabois and Mike Shebat on Work Ethic, Startup Culture and Founder Judgment

Harry Stebbings asks Keith Rabois and Mike Shebat about the culture at Traba. Rabois is a Founders Fund general partner and OpenStore CEO; Shebat leads Traba, a marketplace connecting workers with shifts in light industry. Rabois is an investor in Traba and sits on its board.

Shebat says he and his co-founder wanted a company with global impact. Their first value, dreaming big, is linked to their second: an Olympian work ethic. They hire and promote people who buy into that mission and are prepared to work hard together.

In practice, Shebat says, Traba employees commit to at least 12-hour days Monday through Thursday, work late on Friday, and work in the office. He compares the shared practice to a sports team preparing for a game. He presents this as a deliberate culture choice, not a fit for every worker.

Rabois estimates that more than 80% of successful companies he has seen share an intense work ethic, though he says it is not universal. This is his personal observation, not a measured causal finding. He argues that sustained effort creates opportunities in technology and other fields.

Recalling PayPal, Rabois describes a period in which days off and long commutes were difficult to accommodate. He sees Shebat’s approach as a return to an older style of company building, and says he introduced him to Khosla Ventures investor Samir Kaul, now also a Traba board member.

Stebbings asks whether such intensity is sustainable. Shebat argues that work feels different when people are pursuing a shared craft, while Rabois says progress, happier customers, and improving performance can provide motivation. Both use elite athletes as analogies; neither establishes that their schedule is sustainable for everyone.

Shebat says employees still go to the gym and take care of themselves. He wants colleagues who opt into the same expectations, contending that decisions happen faster when teammates know others will be available in the evening. Rabois says he has observed unusually consistent commitment across Traba.

Stebbings presses the athletic comparison: rest is part of training, and an extra hour may not help. Shebat says people sleep, take breaks and spend holidays with family, but he wants the roughly 60 hours a week to be high leverage. He argues that growth requires stretching beyond what is comfortable.

Rabois likens other forms of preparation to an athlete studying game film while recovering physically. On side projects, Shebat prefers employees to concentrate on the company’s mission. He recalls his brother focusing on swimming after trying several sports and eventually reaching the Olympic trials.

Rabois agrees with focusing on one’s comparative advantage, but makes room for activities whose value is delayed. He reads widely to generate ideas that may only become useful years later, treating that time as an investment rather than a distraction.

Stebbings asks whether running a company alongside investing contradicts that principle. Rabois acknowledges real trade-offs: time on boards and pitches is time he cannot spend on OpenStore. Operating again helps him recall recruiting and growth details, but he says the company-building role bears the cost.

Rabois says his operating skills had weakened during the eight years between Square and becoming OpenStore CEO, and that regaining fluency took time. Watching Shebat’s management also exposed what he could do better. He presents the experience as a lesson in how quickly operating knowledge can age.

Shebat explains the culture directly to candidates and looks for genuine enthusiasm, rather than trying to convince everyone. He says many opportunities are built around a different balance and that is fine. Some people nevertheless joined believing the expectations were exaggerated, then left when they saw the actual schedule.

Stebbings asks whether extra demands come with extra pay. Shebat says Traba pays well in cash while managing its resources as a Series A startup, and emphasizes equity as the larger potential upside. That upside depends on the company’s future value and is not guaranteed.

For Shebat, a candidate overly focused on title is a warning sign because startup employees must solve problems beyond a job description. He sees a strong cash focus as a softer concern: people can have student debt, families and other obligations. He says he still expects candidates to care about equity.

Asked whether the culture can scale, Shebat says Traba initially worked in the office at least six days a week for 12 hours, then relaxed the schedule somewhat as its risks and staffing needs changed. He expects further adaptations as the company grows but wants to preserve speed and performance.

Shebat compares a company to an Olympic team rather than a family, including the possibility of removing someone who is not contributing. Rabois thinks larger organizations tend to become less consistent and recommends building advantages, such as network effects, before that happens. These are their management judgments, not rules that apply to every firm.

Rabois warns that a hiring mistake can spread if the person hires others with the same mismatch. He praises Shebat for quickly giving direct feedback and, if the issue does not improve, changing the team. Shebat also looks for positive force multipliers whom he can promote and give more responsibility and equity.

For Shebat, a leader’s small habits set standards for everyone else. A manager who arrives late may normalize lateness across meetings, so he includes the effect a person has on colleagues in reviews and promotion decisions. Rabois connects this to Andy Grove’s idea of high-leverage management.

Stebbings asks whether celebrating wins creates complacency. Shebat says he shares milestones and recognizes growth and unit economics, then reminds the team that past results do not guarantee the next quarter. Rabois compares each new year or funding interval to a sports season that begins again at zero.

Shebat says the size of the eventual outcome matters as well as reaching an IPO. Rabois offers LinkedIn as his subjective example: despite its roughly $24 billion acquisition, he estimates it achieved only 5–20% of its potential and attributes part of the gap to culture. That estimate and explanation are his opinion.

On parenting, Rabois says demanding work and raising children can coexist, citing colleagues from his legal career. He believes parents may need greater discipline in allocating time. The example reflects his experience; the feasibility of such hours depends on individual circumstances.

Shebat urges people in their twenties to explore enough to find what they want to pursue, then invest deliberately in learning and growth. He says travel is possible but questions time spent on activities that do not contribute to development. Rabois likewise sees high opportunity costs in the early years of a technology career.

Both point to challenging early experiences as a way to develop capability. Rabois cites founders and former interns he has worked with; Shebat recommends putting oneself in situations that reveal unexpected capacity. These are examples from their networks, not proof of a single career path.

Stebbings asks whether great entrepreneurs tend to begin entrepreneurial projects young. Shebat values resourcefulness: questioning an apparently fixed constraint and finding another way to a goal. Rabois points to Paul Graham’s phrase “relentlessly resourceful” and believes the relevant traits often appear early.

Stebbings is skeptical of first-time founders because inexperience can consume time and runway. Rabois disagrees, saying many of his strongest investments were first-time founders whose ambition and lack of ingrained rules were advantages. He recommends pairing that energy with experienced investors or board members who can expose blind spots.

Rabois says his own mistake at OpenStore was not shaping culture deliberately enough in the first year. He compares culture to concrete: malleable when liquid, but expensive and disruptive to break after it sets.

Shebat says his early mistake was treating every detail as equally important. As the company scales, he tries to identify the decisions that can move the business most, delegate other work and still check the results. Rabois urged him to focus like a small special-operations team rather than optimize every activity equally.

When Stebbings asks what investors do when founders disappoint, Rabois compares early-stage venture investing to baseball. His illustrative estimate is that a world-class seed or Series A investor might be right 40% of the time; it is a rule of thumb, not an audited fund statistic. He says he usually offers feedback rather than instructions.

Shebat says he weighs advice by the adviser’s relevant experience but must also account for his own company, its customers and employees. He respects Rabois’s experience with operational businesses while retaining responsibility for applying advice to Traba’s particular circumstances.

Rabois agrees that a founder must translate general frameworks into a specific company. He says Fair founder Max Rhodes often asks for a framework for thinking about a problem rather than an answer. He contrasts Apple’s secrecy with more transparent organizations to argue against assuming that one management practice fits all.

Shebat offers a marketplace example. Investors often expect acquiring workers to be the bottleneck, but he says Traba attracts workers through community effects and is constrained more by business demand. He describes this as a company-specific dynamic that investors and new employees need to understand.

Stebbings advises founders not to spend too much effort educating investors who do not understand the business. Rabois says Founders Fund found Traba’s unusual demand constraint compelling. He also discourages practicing a pitch with investors who ask different questions from the people a founder ultimately wants to persuade.

Asked about location, Rabois states his preference for in-person startups and says Founders Fund had generally avoided remote companies. Shebat says Traba deliberately began in Miami, its first market, so employees could visit warehouses and understand customers. Both are advocating their preferred approach, not establishing that remote startups cannot succeed.

Shebat says a clear statement of expectations can attract people with similar commitments even in places where many workers prefer other arrangements. He regards ambiguity about those expectations as a hiring risk.

Stebbings raises GitLab and other remote-company counterexamples. Rabois says he sourced GitLab as a seed investment and sees open-source companies with distributed contributors as a special case. He speculates that some other companies adopted remote work after gaining momentum; Stebbings notes that at least one had made a conscious transition later.

Rabois explains why he admires Airbnb’s network effects: more hosts improve selection locally, while travelers carry their experience between markets. He discloses that he invested in Airbnb early. He contrasts this cross-market benefit with the predominantly local effects of many marketplaces.

In a rapid-fire round, Shebat says he would be interested in leading The New York Times for a day and advises founders to monitor competitors without obsessing. In the 2023 interview, Rabois predicts structurally persistent inflation and says interest rates are unlikely to fall much; this is a forecast, not an established outcome.

Rabois says he remains optimistic about technology but expects genuinely exceptional startup investments to be rare. Shebat’s best advice from building Traba is to be unapologetic about what the company stands for, because clarity shapes downstream decisions.

Rabois says Founders Fund should cultivate younger investing talent. He finds it hard to identify outstanding investors without seeing them actually source and close investments, then watch the companies develop. Unlike an operating executive, he says, an investor’s definitive returns can take six to ten years.

Asked how much money an investor must lose to learn, Rabois questions whether very large losses are necessary. He claims that early signs within a year often reveal whether an investment is promising, citing Traba, Fair and Ramp. Those early judgments are his impressions and are distinct from realized long-term investment returns.

Looking ten years ahead, Shebat describes an aspiration for Traba to become a public company working toward a trillion-dollar valuation, improve millions of lives and make supply chains more productive. These are his goals and predictions for the company he leads, not achieved results. The guests close by thanking Stebbings for the conversation.