Jake Kent and the art of taking your time

Jake Kent has a restaurant problem. Asked to choose a favorite in New York, he could narrow it down only to two: Primola and Campagnola. Old-school Italian, both. He called himself an old soul. For someone whose working life has included hospitality, WeWork and a consumer startup, it is a pleasingly consistent answer. A good room matters. So does the feeling of being looked after. The menu, apparently, can remain a subject for negotiation.

The same attention to experience runs through a much less leisurely decision. Before Dandi Fertility launched in May 2024, Kent and his collaborators spent two years developing it. He has said there were people urging them to hurry. They kept listening and revising. In the compressed language of a launch announcement, those two years can disappear into a sentence. In a working life, they occupy rather more space.

Kent’s story becomes interesting in that space. He is a founder with experience selling to large organizations, but also a podcast host asking how people might live with fewer borrowed expectations. He understands the usefulness of a polished presentation. His personal projects leave room for an unfinished one. Follow those threads and a career that crosses several industries begins to look less scattered.

The useful habits of a hotel person

He began in hospitality. That starting point matters because he still uses it to explain his work. Hotels make experience unusually concrete: a guest encounters the result of dozens of decisions, usually without seeing the people who made them. The detail that feels incidental in a meeting can become the detail a customer remembers. There is a certain education in having your intentions inspected by someone who has just arrived with luggage.

Kent carried that interest into WeWork, which he joined in 2015. His public professional biography describes a role in developing WeLive, the company’s residential concept, followed by work on the enterprise business. The change took him from an individual’s experience of a place toward the requirements of large corporate customers. Spaces still mattered; so did the work of explaining their value to another organization.

It is tempting to treat this as a tidy apprenticeship for founding a company. Careers are rarely considerate enough to arrange themselves that way. What can be said is more useful: Kent had worked with physical environments, customer expectations and business development before Dandi. The later company brought those interests into another setting. He had already spent time considering how an experience gets designed and how an organization persuades people to try it.

A year spent asking questions

When Kent describes Dandi’s development, he gives the first stretch to listening. Roughly a year went into learning from the people the company hoped to serve. Surveys, interviews, polls and focus groups gave the team different ways to hear what mattered. His account places the customer conversation before the finished solution. That order sounds obvious until an appealing idea, a deadline and a bank balance are all in the same room.

There is a particular difficulty in waiting when you believe you have found something worth making. An object gives a team evidence of activity. A conversation may instead produce a better question, or require yesterday’s certainty to be quietly retired. Neither is much use for a celebratory photograph. Both can be useful to the person who eventually has to use the result.

Kent describes a four-part method: “listen, build, test, refine.” The words are ordinary. Their order carries the argument. Each stage allows the next to be questioned, and refinement leaves the door open for another pass. A founder’s confidence can get a project started; the method asks that confidence to tolerate company. Other people get a say in whether the original idea survives.

The work also required choosing where to put limited attention. Building across physical products and services meant competing demands on the team’s time. Kent has identified prioritization and bandwidth as a challenge. Anyone who has tried to answer three urgent questions before lunch will recognize the outline. At a young company, however, the questions can determine what the company becomes.

The money has to last

Dandi announced $1.3 million in pre-seed funding in May 2024. Tiferes Ventures led the round, joined by Ruttenberg Gordon Investments, Winklevoss Capital and the WeWork Alumni Fund. The announcement supplied a visible milestone after the less visible development work. Capital gave the team resources to proceed. It also introduced the familiar obligation to choose what those resources would pay for.

Kent’s advice to other founders was to budget as though the next funding round might never arrive. It is a sentence with little interest in the glamour of fundraising. The imagined future round does no work in today’s budget. Whatever a founder hopes will happen, the available money still has to cover the decisions already being made.

“Spend every dollar under the assumption you might not raise another.”

Jake Kent · on startup budgeting, 2024

That caution sits comfortably beside a slow development process. Taking time is a choice with a cost, even when it is the right choice. A company that wants to keep learning has to preserve the ability to do so. There is something quietly practical in putting customer attention and financial restraint in the same story. The first determines what deserves building; the second helps determine how long the team can keep at it.

Kent also paid attention to how a young brand reaches people. In July 2024, he described grassroots ambassadors as responsible for 40 percent of Dandi’s sales since launch, with commissions on the sales they generated. That was an early, dated account of one distribution channel. It offers a glimpse of the commercial work behind a brand whose development had begun with conversations: reaching customers required relationships as well as a website.

A second microphone

Alongside his company work, Kent created Searching for More. The podcast arrived in August 2023 with a teaser, an introduction and episodes that moved into personal reflection. Its central concern is recognizable well beyond startup life: the difference between the person you are and the person you have learned to present. A job title can be useful shorthand. It can also become an unusually small container for a life.

The show asks listeners to examine expectations they may have accepted without choosing them. Its early episode titles include The Intro, My Truth and How to Search for More. The language is personal rather than corporate. A founder accustomed to explaining what a company does is turning the microphone toward the question of who a person gets to be.

There is an interesting tension here. A business needs a proposition that can be understood quickly. Personal inquiry tends to make the description longer. It adds qualifications, changes of mind and questions for which the next episode may have no settled answer. Kent’s public work accommodates both forms. The company biography gives the outline; the podcast makes room to wander beyond it.

He later announced a Substack called A Work in Progress, presenting it as a place for more candid conversation about the harder parts of ordinary life. The title allows incompleteness to remain visible. A polished professional profile usually edits that quality out. Choosing it as the name of a writing project suggests an appetite for a conversation with fewer finished poses.

An old soul at the table

His comments about collaborators add another small piece to the portrait. In a testimonial for the creative team Really Kind Creative, Kent praises generosity and the support available within a working relationship. His testimonial for Patent Authority similarly values clear communication, meticulous work and a sense of partnership. Even in the formal language of a recommendation, his attention returns to how people work together.

These are modest details, but useful ones. A professional biography can make a person look like a sequence of promotions followed by an announcement. Here are preferences instead: listening before deciding, colleagues who communicate clearly, a restaurant with an old-school character. They offer texture without requiring the career to become a fable about inevitable success.

By October 2024, Dandi had earned a place in TIME’s Best Inventions selection. That recognition belongs in the company’s record. Kent’s own story also contains the preceding stretches that an award cannot compress very well: hotel work, residential experiments, enterprise conversations, development, and the decision to make a podcast while building something else. There are several kinds of work on that list, with different measures of completion.

One attraction of Kent’s path is that he keeps returning to experience from different directions. In business, he asks what the customer encounters. On the podcast, he asks what happens when a person examines the expectations around them. At an Italian restaurant, presumably, the question can be allowed to rest for a while. Even a dedicated listener is entitled to order dinner.

Primola or Campagnola remains unresolved. The larger pattern is easier to see. Kent has spent his career moving between the places people occupy, the things companies build and the stories people tell about themselves. His most revealing decision may still be the one that preceded the launch: allowing enough time for someone else’s answer to change the work.