Steven Krein’s first business required a typewriter and a willingness to entertain small children. At nine, he became a magician clown, performing at birthday parties in the neighborhood. He typed his own business cards. There is something reassuring about an entrepreneur whose earliest customers wanted a decent party rather than a return on invested capital. The proposition was simple enough for everyone to understand.
Years later, he would help take an internet company public. Still later, he would spend much of his working life helping other founders. The childhood act makes a useful opening to that story: an audience, an invitation, a reason to turn up. Krein’s businesses grew more complicated. His interest in bringing people together survived the change of costume.
The crystal ball on the dinner plate
During his third year of law school, Krein wanted to move to New York and get involved in the internet. His father wanted him to finish his degree and become a lawyer. A professor, Richard Herman, proposed dinner with his parents. When Krein sat down, a crystal ball was waiting on his plate. Herman asked him to describe the future he saw.
Krein recalls that question as a turning point. The prop gave him a way to explain an ambition that had been difficult to convey: to be in New York, close to the people thinking about the internet, with a chance to build something. He kept the crystal ball. In a later conversation, he held it up while telling the story. For a former magician, the symbolism was almost indecently convenient.
His early career already crossed the boundary between established professions and new technology. He worked for Apple Computer, with responsibility for its push into New Jersey, Pennsylvania and Delaware. In 1992, he co-founded an online service for Delaware attorneys. He subsequently worked on Law Journal EXTRA!, the legal publishing service that would become part of the Law.com story.
He earned a bachelor’s degree at the University of Maryland and a law degree at Widener. Those credentials usually suggest a fairly legible route through adult life. Krein took them into a business where the route was still being drawn. Lawyers needed information; publishers had information; computers offered another way to connect them. Before the promotions business, there was this quieter problem of getting useful material to the people who needed it.
A public company, with a public reckoning
Webstakes was founded in 1996. Krein became its co-founder and chief executive, building an internet promotions business that subsequently carried the name Promotions.com. It went public on Nasdaq in 1999. The company reached a market capitalization of about $500 million before its acquisition by iVillage in 2002. That figure describes the company’s stock-market value, rather than Krein’s personal wealth or the eventual purchase price.
The work involved online advertising, direct marketing and technology. Familiar advertisers could reach people through a new medium, with promotions providing the invitation to participate. The enterprise belonged to the first commercial chapter of the web, when established brands were deciding what an online customer relationship might look like. Krein was building both a business and an argument for how the medium could earn its keep.
There were uncomfortable quarters, too. In September 2000, Promotions.com warned that third-quarter revenue would fall short of expectations. It projected revenue between $6.4 million and $6.9 million, alongside a net loss between $5.8 million and $6.5 million. Krein acknowledged a difficult quarter for internet marketing companies while maintaining confidence in the business’s longer-term prospects.
Read together, the flotation and the warning give the early career its proper texture. A market value can make a founder look prophetic; a quarterly loss asks much less flattering questions. Customers, expenses and investor expectations continue to exist after the celebratory photographs. Krein’s subsequent emphasis on supporting founders has more substance when set beside that experience of running a company whose disappointments were also public.
The partner who stayed
Unity Stoakes was chief marketing officer at Promotions.com. Gregg Alwine was its chief technology officer. When the team launched OrganizedWisdom, the people involved had already spent years building companies together. Krein had also stayed briefly as a senior executive at iVillage after the sale. A change of company did not require a wholesale change of companions.
That continuity matters. A business partnership acquires a history of decisions, arguments and repaired mistakes. The partners know what the other person is like when the plan stops working. Krein and Stoakes brought that accumulated experience to StartUp Health, which they co-founded in 2011. Their joint letters later described the entrepreneur’s journey as long, with repeated ups and downs, sometimes within the same day. The partnership itself was part of how they kept moving.
In those letters, the two founders put relationships and community near the center of their working philosophy. The significant word is “organized.” A collection of acquaintances becomes useful when people can find one another, understand a shared purpose and contribute something concrete. Their long partnership offered a small working example of the larger network they wanted to build.
Who brings the batteries?
Krein credits entrepreneurial coaching with changing his view of building his first and second companies. He also joined YPO, the peer network for business leaders. The support system extended beyond hiring the right team. It included people outside the business who could offer perspective, guidance and introductions. At StartUp Health, long-term coaching and a peer community became part of the proposition offered to entrepreneurs.
This gives his career an unusual second act. The experience gained inside companies became material for helping people running their own. The founder who had needed guidance started designing ways for other founders to find it. A membership, a conversation and an introduction are modest-looking things. They can matter greatly to someone trying to make a consequential decision with incomplete information.
In a 2019 interview about selecting startups, Krein described a scorecard of eight entrepreneurial mindsets. Long-term commitment was one consideration. Another was whether a person gave energy to the people around them and avoided unproductive arguments. His shorthand for that quality was “batteries included.” It is a charmingly domestic phrase to bring into a conversation about investment.
The phrase also asks something practical of a prospective colleague. An impressive résumé gives little indication of how a meeting will feel after two hours. Krein’s filter considers the effect a founder has on others, alongside their willingness to persist. A person can bring an excellent idea and leave everyone else exhausted. In a community built around repeated collaboration, that cost compounds.
“Do they give energy to others?”Steven Krein, on evaluating entrepreneurs, 2019
A lesson from the volleyball court
Watching his youngest daughter compete in a volleyball tournament, Krein noticed how her team responded to mistakes. A missed ball or a hit into the net brought encouragement. Across the court, he observed a different pattern of responses from another team. He paid attention to the players’ expressions as well as their words. The match became, for him, a demonstration of the behavior he wanted in a working community.
His account is revealing because the unit of observation is so small. One error, followed by one response. The encouragement was immediate, rather than reserved for a meeting about team culture. He connected it to the ground rules he tried to reinforce at work: support for other people, support for ideas and language that helped people continue. The referee was presumably occupied with more pressing matters.
In another conversation, Krein explained how reading Nassim Nicholas Taleb’s Antifragile changed the way he thought about resilience. Enduring disorder was one ambition; becoming stronger through it was another. He linked that idea to the values he shared with Stoakes and their team. He also described looking at the depth and duration of an entrepreneur’s relationships when judging their capacity to collaborate.
Both observations ask how someone behaves over time. A founder can prepare a polished introduction. A long relationship carries more evidence. It has survived inconvenience, change and the occasional need to admit a mistake. Krein’s attention to those histories fits a career in which the same business partner has appeared across successive ventures.
The room still matters
Technology occupies plenty of space in Krein’s conversations, but he also pays attention to the limits of a screen. In a 2024 discussion, he questioned the value of traveling to hear material that could already be watched or read online. Connecting with the people in the room seemed more useful to him. That is a fairly pointed observation from someone whose work includes events and interviews.
He discussed another change in the same conversation: the rise of fractional roles, in which a company can draw on someone’s expertise without employing them full time. Collaboration tools made those arrangements easier. The underlying question remained familiar: which person can contribute the capability a company needs? The answer might live elsewhere, or work with several businesses, or need only a portion of the week.
The network around StartUp Health has included investors and partners such as Steve Case, Mark Cuban, Esther Dyson and Brad Feld. Those names help explain the range of people its founders brought into the conversation. The model’s day-to-day usefulness, however, depends on what happens after an introduction: whether someone listens, whether the advice fits and whether the relationship continues when the initial excitement wears off.
Experience gets another turn
In July 2026, Krein returned to the question of age and ambition with his podcast partner, entrepreneurial coach Dan Sullivan. He recalled joining coaching sessions in his twenties and hearing older entrepreneurs describe risks they were reluctant to take. Now in his mid-fifties, he was hearing similar reservations among his own peers. Artificial intelligence had given him a reason to reconsider the supposed advantage of youth.
His argument was that decades of judgment, taste and pattern recognition could become more useful when paired with new tools. He also warned that those tools could multiply dysfunction. The observation gives his enthusiasm a condition: experience helps when someone is willing to rethink the work. Having been present for an earlier technological shift does not confer an exemption from learning the next one.
The current StartUp Health team page lists Krein as strategic advisor and co-founder, with Stoakes as CEO, president and co-founder. Earlier in 2026, Krein had hosted an investor conversation with 7wire Ventures partner Alyssa Jaffee. Her discussion included the fit between founders and investors and the possibility that venture funding might be the wrong choice for a particular business. These are questions about the terms on which people work together, a subject that runs through his career.
Krein has described himself as a “convener of community.” In 2024, the University of Maryland recognized him with its EnTERPreneur Award. His connection to Maryland included service on the Dingman Center for Entrepreneurship board, while one of his daughters was attending the university. The circle had widened, then returned to a place where his own ambitions had taken shape.
The typed business cards, the dinner-table crystal ball, the public company and the enduring partnership belong to the same story. Each involved persuading other people to see a possibility and participate. Krein has spent years finding ways to keep that participation going. There is considerably more paperwork than there was at the birthday parties. The invitation remains recognizable.