Unity Stoakes and the compound interest of curiosity

In December 2025, Unity Stoakes spent an afternoon with Esther Dyson overlooking the port of Oakland. Ships moved through the harbor. The two talked about limits, leadership, abundance, and what people ought to preserve as technology accelerates. He had known her for roughly thirty years. The conversation had the unusual advantage of being a reunion as well as an interview.

Long before Dyson became an investor in his companies, she was someone a young communications professional wanted to meet. Decades later, he was still asking her questions. The setting had changed; the willingness to listen had survived. For a career spent around new technologies, that is a pleasingly durable piece of equipment.

Stoakes is now CEO, president, and co-founder of StartUp Health. The title suggests someone occupied with the destination. His history keeps returning to the introductions along the way: an email, a shared lunch, an adviser who became a friend. To follow his career is to watch the distance between strangers shrink, sometimes over years.

Iowa, with a generous helping of Dylan

His explanation for the name Unity begins with Bob Dylan. His mother went into labor at a Dylan concert, he has written, and he lived on Sunshine Farm in Iowa. As origin stories go, it requires very little assistance from a branding consultant. The farm was in Oxford; Iowa City also figures in his memories of growing up.

He has defended Iowa City as a place rich in culture and creativity. In a 2007 blog post, he connected that atmosphere to the university and the local writing scene, mentioning that his mother worked at the Iowa Summer Writing Festival. His account puts writers, odd characters, and local pride into the picture of his upbringing.

That distinction matters to the story. The Iowa he describes contains a working cultural life, with people making things and other people paying attention. Later, when he writes about design, culture, and technology together, the combination seems less like an executive adding a fashionable interest to a biography. These interests already had a home.

Learning to explain the internet

Boston University came next. He studied communications and political science, attending from 1992 to 1996. He received writing and student awards in his graduating year, including the Gerry Powers Award and a Most Distinguished Student Award. Language was part of his training before investment became part of his work.

In 1996 he moved to New York. His early career included Middleberg Interactive, followed by work helping build Webstakes.com and Promotions.com. The latter went public on Nasdaq in 1999. It was an apprenticeship in the commercial internet while the commercial internet was still inventing its manners.

There is something useful about beginning in communications at such a moment. A product needs an explanation; a young company needs people willing to hear it. Stoakes’s subsequent work as a publisher, interviewer, and founder keeps those tasks close together. The writing sits alongside the company building, rather than arriving as a retirement activity.

His partnership with Steven Krein runs through this period and the companies that followed. They later co-founded OrganizedWisdom, then StartUp Health in 2011. The sequence gives their work a continuity that a list of startup names can obscure. People, as well as products, carry experience from one venture into the next.

A boardroom begins with lunch

At OrganizedWisdom, Stoakes and Krein wanted advisers with experience beyond their own. They drew up an ambitious list. Dyson was an early supporter and helped introduce them to Gerald Levin, the former Time Warner chief. The meeting began over lunch, with the founders, Dyson, Levin, and his business partner Bill West.

What Stoakes remembered about Levin was the quality of his attention. He asked about family and about interests outside business. A founder looking for a mentor had encountered someone who wanted to understand the individual before reducing him to a company. Levin eventually joined the board.

The anecdote has a practical scale: a handful of people around a table. It also makes the later emphasis on community easier to understand. An introduction can change who gets to ask a question, whose experience becomes available, and how an unfamiliar problem is approached. The lunch belongs in the business story.

The browser with too many tabs

For a less formal portrait, open his September 2006 list of internet services. He described working at his computer while listening to a podcast, connecting with family through Skypecasting, and running at least ten web programs in Firefox. Even by the standards of the period, his browser sounds well attended.

His favorites included Basecamp, Flickr, Wikipedia, and tools for managing blogs. Netflix still meant DVDs arriving each month. He liked the freedom of carrying an internet phone number between places and the convenience of online groceries. The list records technology entering ordinary life, one practical improvement at a time.

There is a comic footnote for anyone tempted to give a past opinion permanent residence. Facebook’s wider opening made him wonder whether he would stick around. LinkedIn was a service he said he used relatively little. Even an enthusiastic early user gets to be surprised by what happens next.

The list also shows the pleasure he took in passing useful things along. It is easy to imagine a founder’s reading reduced to competitive intelligence. Here the subjects include family calls, photographs, shopping, and films. The appeal is recognizably domestic: a tool earns its place by making some part of a day easier.

A network needs something to do

StartUp Health gave the long partnership a new organizational form in 2011. Stoakes’s present role combines operating responsibility with the work of a co-founder. He also publishes StartUp Health Magazine and co-hosts StartUp Health NOW. The company, the publication, and the conversations provide several ways for people to meet his ideas.

In his November 2024 essay on networks, he argued that a shared purpose gives connections their force. He described the value of people exchanging insights and making useful introductions at the right moment. Having many names within reach is only a beginning. The question is what those people can work on together.

It is an argument with a recognizable history behind it. The early effort to reach an influential editor, the relationship with Krein, and the recruitment of advisers all involved repeated contact around work. A network assembled for appearances would have rather less to do on a Tuesday morning.

His current activity still includes that conversational work. In September 2026, he hosted Menlo Ventures partner Greg Yap for a discussion of investing and what founders need to compete. The format puts an experienced investor in reach of other builders. It is another instance of using a conversation to make someone else’s experience available.

Fifty books, with nine extra

For his fiftieth birthday, Stoakes began a list of books that had changed his life. He kept it private at first. In January 2025, around his fifty-first birthday, he finally shared it. The resulting selection contained fifty-nine entries. Anyone who has tried to clear a bookshelf will recognize how fifty can become a negotiating position.

The company on those shelves is eclectic: Joseph Campbell, Harpo Marx, Bob Dylan, Shel Silverstein, and books about making products and writing clearly. It is a reading life with room for comedy, narrative, and practical instruction. The list resists the tidy impression that every book a founder opens must contain a business model.

Writing has been a recurring habit. He says he has blogged intermittently since 2004. In October 2006, he devoted a short post to writing advice associated with Stephen King, boiling the lesson down to cutting unnecessary words. That interest in brevity has a charming companion in his taste for expansive lists.

Today his personal journal, Dream Impossible!, gives him a place to explore culture, design, leadership, and emerging technology. Its description also mentions UNITAS X, his private practice working with selected founders, investors, and institutions at moments of change. The combination keeps him moving between ideas on a page and decisions inside organizations.

Permission to look up

For someone attracted to ambitious projects, Stoakes offers remarkably ordinary advice about moments of upheaval. In a November 2024 essay, he recommended a long walk, more questions, better listening, and a temporary change of routine. He urged builders to reconsider assumptions when the world changes around them.

His examples included the arrival of the web, the dot-com bust, the iPhone, and the period following ChatGPT’s release. He treats such moments as occasions to reassess the work. That is a useful qualification to his optimism: enthusiasm still has to leave enough space for a changed mind.

His life in Berkeley includes interests that sit comfortably beside that advice: photography, street art, architecture, bocce, trees, and walking. He has described a family life with his wife, Katya, and their children, as well as tending a rose garden. The person in the business biography also has things to look at when he leaves the screen.

One small line from his personal introduction supplies a standard for all this activity: “I strive for the sum of my contributions to produce more positive energy than I consume.” It is an aspiration rather than a balance sheet. A company can count meetings and investments; generosity asks a less convenient question.

“Take a long walk. Ask questions. Listen more.”Unity Stoakes, November 2024

The Oakland conversation brings that question back to a human scale. After thirty years, an early professional contact was still someone he wanted to hear from. New ventures, new tools, new titles; an old relationship with another afternoon available. For Stoakes, curiosity has had time to become a way of working.