After Stephen Sokoler sold Altrum Honors in 2014, he did something wonderfully inconvenient for a founder with a completed exit: he admitted he did not know what came next. He began meeting people, telling them his story and asking for their thoughts. Then he asked whom else he should meet. The next business started taking shape in conversations, before it had a product to sell.
There is a particular freedom in that interval. A sale supplies an ending that looks satisfying from outside. Inside, it leaves a rather practical vacancy: what will occupy Monday morning? Sokoler had already spent years running companies. He understood the mechanics of building. Deciding what deserved to be built required a different sort of work.
Journey, which he founded in 2015 and still leads as CEO, became his answer. But the space between the two companies is worth lingering over. It gives his career a more interesting shape than the usual sequence of company names. Here was someone who had learned to sell, manage and expand, deliberately making room for other people to influence the next move.
A snow shovel, a telephone, a mother
Long before there was a company to sell, there was snow in Queens. Growing up, Sokoler handed out flyers for a snow-removal business and recruited other children to shovel. His mother answered the telephone. He shoveled too. It was a small operation with a surprisingly recognizable organization chart: sales, dispatch and people outside doing the actual work.
He also sold sodas at summer camp. At NYU, parties organized with friends became a business, and he went on to produce hip-hop concerts. These were different enterprises, but each involved assembling people around something they wanted. A clear driveway, a cold drink, a room worth going to: the customer proposition could be explained without a slide deck.
The childhood business is amusing partly because the family telephone was doing the work now assigned to software. Someone needed to receive the request, know who was available and make sure the job happened. Technology has improved considerably. The snow remains stubbornly manual.
Sokoler attended NYU's Stern School of Business from 1997 to 2001, studying finance and international business and graduating cum laude. His education included a semester in Madrid. Formal business training sat alongside the less tidy education of persuading people to buy something, come somewhere or join in.
When the souvenir outlives the party
By 2008, Sokoler was president of Icon Recognition, making the commemorative objects bankers call deal toys. A financial transaction could become a miniature trophy. When the financial crisis arrived, the market for those celebrations became much harder. He was calling around for business as dealmaking faltered. It was an early lesson in depending on customers whose circumstances could change abruptly.
Later came Altrum Honors, where he was co-founder and CEO. The company helped organizations recognize achievement and celebrate employees. Its growth combined acquisitions with the ordinary work of winning business. Sokoler sold it in September 2014, bringing that chapter to a close.
Recognition is a curious business because the object carries more than its material value. The thing on the desk announces that something happened and somebody noticed. Even a small keepsake can become an argument about belonging: you were here; you were part of this; your work counted.
That makes the continuity in Sokoler's career easier to see. Different products can address the same human appetite for acknowledgment. His later work would put people together in different ways, but he had already spent years serving organizations that wanted their employees to feel part of something.
Taking the next idea out to lunch
During the interval after the sale, one of the people he met was entrepreneur Matthew Brimer. Their friendship began around the time Sokoler was working out his next direction. More than a decade later, the two could still trace their connection to those exploratory meetings. A lunch can look like an unremarkable entry on a calendar until enough time has passed.
The two questions Sokoler used are useful precisely because they leave room for an unexpected answer. Asking for thoughts invites a response wider than a verdict on a finished pitch. Asking for another person to meet lets a conversation travel beyond the room. The process gives an idea opportunities to change before its founder has invested too much pride in defending it.
In his own account of those years, Sokoler describes reading widely, including Viktor Frankl, Dale Carnegie, Stephen Covey and Eckhart Tolle. He kept a personal list of things he wanted to remember and do. In 2011, he also went to Sydney to open an office for his earlier company. Living somewhere new gave him another perspective on a life largely spent in New York.
The company was allowed to change
Journey's early development included live group experiences and a consumer app. What interested Sokoler was participation: people turning up together, with a teacher and the possibility of interaction. For a technology business, that is a specific design choice. The person on the other side of the screen matters to the experience.
The branding followed that interest in people. Sokoler credited his marketing colleague Jen with bringing the brand to life. He remembered a photo shoot with teachers, photographers, lighting and makeup, when the company's identity became visible in the room. A business that had existed in plans and conversations suddenly had faces.
It is an appealingly ordinary breakthrough. Company histories tend to reserve their turning points for a funding announcement or a sales figure. His recollection made space for the moment collaborators saw themselves in the work. Nobody needed to ring an exchange bell. The people making the thing could recognize what they were making.
By October 2020, Journey had closed its consumer business to concentrate on selling to organizations. That decision deserves its own place in the story. An app can be real, carefully made and worth launching, while the business around it still needs to change. A founder must sometimes stop serving one market in order to serve another properly.
In later discussions of the shift, Sokoler described several product iterations, the difficulty of consumer acquisition costs and the value of early customers such as Warby Parker. Enterprise sales brought its own questions: who buys, what gives that buyer confidence and how does the offering earn a place inside an organization?
“Not every business should be a venture-backed business.”
Stephen Sokoler, in conversation with Fund/Build/Scale
That is a useful sentence from someone who has built both an earlier company and a venture-backed one. Funding has consequences for the kind of business a founder is expected to create. The ambition needs to fit the financing, and the financing needs to fit the work. A large cheque cannot settle that question on a founder's behalf.
Still willing to be the student
In 2023, Sokoler joined the QuantumShift program run by KPMG and the University of Michigan's Ross School of Business. It brought founders, owners and CEOs together for several days of learning and collaboration. For someone who had already sold a business, returning to a room of peers was another instance of keeping the conversation open.
His reading habits have an equally practical streak. He has recommended Matt Mochary's The Great CEO Within, named StrictlyVC and Morning Brew among his newsletters, and mentioned How I Built This as a podcast he enjoys. Business building, in that selection, remains something to study rather than a subject exhausted by one successful sale.
His public work now includes writing, interviewing and speaking. In a September 2026 interview, he discussed a follow-up book he expected to release at the start of the following year. He described gathering lessons from people leaders. It was a prospective publication date, but the method sounded familiar: listen to people doing the work, then make something from what they know.
There are less corporate details, too. He is a Mets fan. He has supported Partnership with Native Americans. His volunteer experience includes education and human-rights organizations. Those particulars give the biography some texture beyond a founder title, without requiring every interest to become a lesson in leadership.
A different address, the same friendships
In September 2025, Sokoler announced that he had moved to South Florida after 46 years in New York City. He spoke warmly about the city and the friendships it had given him. He wanted more time with his wife and son, and said he intended to keep his New York relationships strong. His current professional profile lists Boca Raton.
A change of address is a modest sort of plot twist. There is no acquisition price attached to it, no market share to calculate. It still rearranges the hours in a day and the people one sees in them. Sokoler described the move in those everyday terms, as a change in pace and family life.
The founder who once went around asking whom he should meet next is now making room for the people he already knows. That is a satisfying place to leave this chapter of his story: another decision about how to spend a Monday, and who should be there when the workday ends.