Rob Solomon and the trouble with getting bigger

Rob Solomon has a useful question for a job candidate: “Who hates to work with you?” It has considerably more bite than asking where someone sees themselves in five years. The answer might tell you whether a person understands the effect they have on a room. Solomon has an answer of his own: people who want rigidity and structure tend to find him difficult.

That admission helps explain an otherwise restless-looking career. Yahoo shopping, travel search, Groupon, GoFundMe, a consumer brands startup, and now electric aviation: the nouns keep changing. The work keeps returning to a familiar problem. How do you take something people already want to do and build an organization capable of helping many more of them do it?

By 2026, Solomon was CEO of H55, the Swiss electric propulsion and aviation battery company. He had also joined Grindr’s board that June. The executive associated with shopping pages and online donations was working on commercializing equipment for aircraft. An internet career had acquired a rather literal departure gate.

The history student at the keyboard

Solomon was born in New York and grew up in South Florida, the youngest of four boys. Swimming and water polo helped take him to Berkeley. He studied history, competed on two NCAA championship water polo teams and earned All-American honors. His joke that water polo was his real major is a college athlete’s familiar act of revisionism.

The computer industry was hardly a childhood certainty. As a student, he wrote essays by hand and paid someone in the Berkeley Hills to type them. His early employment included testing video games and answering customer calls at Electronic Arts. It is an agreeable beginning for an executive biography: before managing the future, he had to hear what was wrong with the game.

There is a practical education in those calls. A product has to survive contact with the person using it. A complaint arrives without much respect for the organizational chart. That makes this starting point particularly apt for someone whose later jobs would require moving between product decisions and the people expected to carry them out.

His path included educational games and Golfweb before Yahoo. At Yahoo, he eventually oversaw commerce businesses that spanned shopping, travel, auctions and other services. He was learning to manage several ways of making a transaction happen inside a company better known for gathering an enormous audience.

A search box is only the beginning

Travel gave Solomon an early chief executive role. He became president and CEO of SideStep in 2006. The service helped people compare travel options; in December 2007, it merged with Kayak. The deal joined two travel-search businesses and brought together their information, products and experience.

The merger’s stated promise was straightforward: a traveler should be able to compare more choices with less work. Kayak said it would retain both brands and improve access to rates and availability. Behind the search box sat an industry full of suppliers, changing prices and competing distribution arrangements. Making the front end look simple required considerable coordination behind it.

Solomon subsequently worked in venture capital, including TCV and Accel, and served as Groupon’s president and chief operating officer. His responsibilities there included sales, marketing, business development, operations and international markets. Small merchants needed customers; Groupon offered a way to find them online. Delivering that proposition across markets required an expanding human organization.

Published accounts put the team’s growth during his involvement at roughly 100 employees to several thousand. The precise endpoints vary, but the management problem is plain enough. Hiring at that pace changes how information travels, who makes decisions and whether a new employee knows what the company actually expects. A bigger company can develop a remarkable talent for arranging meetings about its own size.

When a donation becomes a habit

In 2015, Solomon took over as GoFundMe’s CEO from co-founder Brad Damphousse. He arrived after the platform had passed $1 billion in cumulative fundraising. The next billion came about nine months later. By October 2016, the community had passed $3 billion. Those were donations raised through the platform, rather than revenue earned by the company.

He understood giving as a behavior the internet could make easier to repeat and share. Someone asks for help. A friend contributes and passes the request along. Other people encounter the story and do the same. A familiar act between neighbors can travel beyond the neighborhood without requiring the organizer to build a fundraising system from scratch.

Solomon’s writing about the second billion included Hailey Fort, a child who built small portable houses for people without homes, and Toni Morgan, whose supporters helped fund her Harvard tuition. These examples gave his platform argument a human scale. The software mattered because it helped a particular person accomplish something another person could understand.

He also pushed the idea into the places where people first learned that help was needed. A 2017 partnership with The San Diego Union-Tribune connected fundraising with newspaper stories. A reader encountering someone’s circumstances could start a campaign directly from the article. The distance between reading and acting had become a product-design question.

For charities, the proposition extended to software they could use for their own fundraising. GoFundMe Charity, introduced in 2019, reflected that ambition. An organization with a mission and supporters could use the platform’s tools rather than assemble every piece itself. Solomon was pursuing both individual participation and the infrastructure institutions needed to support it.

Trust had to travel with the request. In a 2017 interview, he described campaigns receiving their earliest donations from friends, relatives and local communities, alongside monitoring by a dedicated internal team. The emotional appeal and the operating machinery were inseparable. A service inviting people to send money needed more than a touching story.

The invitation that surprised him

Solomon later recalled attending a gathering of business leaders, performers, athletes and journalists about nine months after joining GoFundMe. He wondered what he was doing among them. Then the host introduced him in terms that made him realize the company’s significance was becoming visible beyond its own employees.

It is an unusually revealing executive anecdote. The internal work had begun to acquire an external meaning. People were recognizing GoFundMe as somewhere to turn, and its name was becoming part of ordinary speech. For a manager accustomed to building internet businesses, that recognition carried a different kind of satisfaction.

In January 2020, he announced that Tim Cadogan would take over as CEO in March, while he continued as chairman. His explanation concerned the company’s next stage: a growing institutional fundraising business called for experience spanning consumer technology and business customers. Handing over the job was itself an operating decision.

His involvement in giving continued through GoFundMe.org. Its fiscal 2023 report listed him as a director and recorded more than $156 million raised since the nonprofit’s establishment in 2017. Its work included disaster recovery, family assistance and education. The nonprofit’s 2025 public tax filing continued to list him as a board member.

A Kite meets the weather

Solomon co-founded Kite in 2022 with Juxtapose and Blackstone. Its April 2023 announcement described a $200 million equity commitment and a plan to buy, invest in and operate consumer brands. Shared technology and operations would help those businesses sell across online stores, social channels and physical retail.

The proposition put him back among merchants, products and distribution. A small brand might attract devoted customers while struggling with manufacturing, shipping or acquiring its next buyer. Kite proposed to put those capabilities within reach through a common platform. Its team included GoFundMe colleague Ujjwal Singh and designer Nastasha Tan, whose previous work included IDEO and Uber.

Kite closed in early 2024 after drawing roughly $25 million of its $200 million commitment. The episode puts a limit on an otherwise tempting career narrative. Experience and committed capital do not guarantee that an operating plan will find its market. An executive biography becomes more useful when the unsuccessful venture stays in it.

The next platform has a propeller

H55 brings Solomon to an industry with different measures of progress. The company grew from the technological legacy of Solar Impulse and develops electric propulsion and energy storage systems for aviation. His role includes leading its expansion in the United States and commercializing its technology.

In April 2026, H55 delivered conforming battery modules to BRM Aero for integration into the Bristell B23 Energic. A separate agreement paired H55’s energy storage technology with Safran’s ENGINeUS electric motor for the aircraft. These were steps toward a commercial product, with integration and certification still central to the work.

The company also supplies battery technology for RTX’s hybrid-electric flight demonstrator. That program combines a thermal engine, electric motor and battery system, targeting improved fuel efficiency for regional aircraft. Here, useful connections take physical form. Equipment has to work with other equipment, and evidence has to satisfy requirements beyond a customer’s enthusiasm.

“Just say no.”

Rob Solomon, on focus

Solomon’s advice to founders at AI Fund includes a short instruction: “Just say no.” His concern is the crowded product roadmap and the company trying to solve too many problems at once. After a career spent helping organizations get bigger, it is a fitting preoccupation. There will always be another opportunity to add. The harder managerial task is choosing what deserves the next person, the next dollar and the next working day.