In 2009, Steven Price and his colleagues considered buying into fifteen different kinds of businesses. The list included newspapers, television, movie theaters and summer camps. The financial crisis had made investors cautious. Price’s group decided it was a useful moment to shop. Of all the candidates, they settled on radio: an old medium with local audiences, recognizable brands and an increasingly unfashionable reputation.
The choice is a good introduction to Price. Today, the New York entrepreneur runs 25madison, where company building meets early-stage investing. His career has crossed cellular telephones, software, private equity and public service. Look past the variety of job titles and a recurring question emerges: what does a business already possess that other people have stopped noticing?
The audience was already there
Radio offered a particularly interesting answer. Price saw something valuable in the attachment listeners had to their local stations. A broadcast frequency could carry a familiar voice, a neighborhood argument, a concert invitation and an advertiser’s offer. There was an audience to build around, even if the device receiving the signal had ceased to look like the future.
His description of the medium’s digital credentials drew a parallel between disc jockeys and bloggers. Both produced a continuing stream of commentary. The internet supplied another means of delivery. The observation did not require listeners to abandon an existing habit; it asked the business to become more imaginative about what that habit could support.
His team’s education was equally practical. They visited stations, spoke with general managers and sales representatives, joined sales calls and questioned advertisers. An acquisition thesis might look elegant in a presentation. Going out with the people who had to sell the advertising gave it somewhere less comfortable to stand.
“Radio has been blogging for 50 years.”
Steven Price, 2011
Small markets, considerable ambition
Townsquare Media was founded in May 2010. Its starting point included Regent Communications, which had been bankrupt. This was a rebuilding job with a functioning audience attached. Stations, websites and live events could become different doors into the same local business, provided someone invested in the rooms behind them.
Price was explicit about geography. The largest cities were outside the center of his acquisition strategy. He preferred small and midsize markets, strong station brands and local teams that understood the plan. A university, state capital or military base could make a town attractive by supplying a stabilizing presence. The map mattered because the business depended on the community around it.
That specificity is more revealing than a general appetite for growth. Plenty of investors want more customers. Price was describing the kinds of places where he believed his company could serve them. In an industry accustomed to discussing the next competitor, he was also asking what other products an existing audience and sales force could sustain.
By 2013, Townsquare had added 71 stations through a transaction involving Cumulus. Radio Ink named Price its Radio Executive of the Year for that year. The recognition came as his company was expanding beyond broadcasting, building local web properties and events alongside the stations. The radio dial was becoming the entrance to a larger collection of businesses.
A ticker symbol joins the dial
On July 24, 2014, Townsquare’s shares began trading on the New York Stock Exchange under TSQ. The offering priced at $11 a share. Its filings describe the use of proceeds to repay debt, a reminder that a public debut is also a financing transaction. The ceremony gets the photograph; the balance sheet gets the consequences.
The business continued to develop several ways of earning money from local relationships. Townsquare Interactive, its digital marketing operation, built websites for small businesses. By October 2017, that operation had roughly 12,000 clients and more than 300 employees. Advertisers had asked for help with websites and social media. The company responded by building a service around the request.
When Price moved to executive chairman in October 2017, Bill Wilson and Dhruv Prasad became co-CEOs. Both had been with Townsquare since its founding. At the following earnings call, Price described the journey from approximately 60 stations and almost entirely broadcast revenue to 317 stations, a digital content audience exceeding 50 million monthly unique visitors and a digital marketing business with approximately 12,000 subscribers. Those are 2017 figures, a snapshot of the company he was handing over.
From about 60 stations to 317
Before the microphone, the mobile network
The radio wager had an earlier cousin. In the 1990s, Price was president and CEO of PriCellular, the rural cellular operator associated with his father, Robert. Its territory included clusters in the Midwest, Appalachia and New York. Rural service was a concrete business: licenses, coverage, subscribers and a network that had to work where customers lived.
In March 1998, PriCellular agreed to an acquisition by American Cellular valued at approximately $1.4 billion, including debt repayment. The company had about 250,000 subscribers. Price recalled skepticism about his father’s asset purchases in 1994, when others thought the opportunity had already passed. Their disagreement had produced a business covering more than 5.1 million people.
The sale also demanded a less romantic calculation. A substantial offer had to be considered in the interests of shareholders. Price said he would remain long enough to help close the transaction smoothly. Building a company and deciding when to sell it require different forms of judgment. His experience included both.
A career with several operating systems
Price’s early professional training came through Brown University and Columbia Law School, followed by work at Davis Polk & Wardwell and Goldman Sachs. He later founded LiveWire Ventures in 1998. The move from legal and financial work into running software and services added another kind of responsibility: somebody had to turn the plan into a working organization.
From 2001 to 2004, he served as deputy assistant secretary of defense for spectrum, space and communications. He received the Secretary of Defense Medal for Outstanding Public Service. His career also included roles at Spectrum Equity and Centerbridge Partners; at Centerbridge he led investment efforts in telecommunications, technology and media.
In an essay published in 2020, Price returned to a lesson from the Pentagon in 2001: leaders do not immediately have every answer. He stressed research, quick planning and the flexibility to act differently as circumstances change. It is a more useful admission than the usual executive memoir promise of clairvoyance. Experience, in this account, improves the questions before it supplies the answers.
The founder becomes a co-founder again
25madison was launched in 2018. Price’s fellow founders included Michael Lynton, Matt Fremont-Smith and Kirk Posmantur. The venture studio brought together people who had already run businesses and proposed to work alongside a new generation of founders. The premise was straightforward: an early company could use more than money.
The firm’s co-founder guidance makes that premise tangible. Candidates can arrive with an idea or explore one with the studio. Arrangements vary, but its typical offer includes salary, access to studio services, initial capital, assistance raising further money and founder equity. It describes an initial period of roughly six months for developing the plan and funding strategy.
There is a quietly appealing redistribution of glamour here. The lone founder, usually pictured carrying the entire company in a laptop bag, acquires colleagues. Recruiting, design, research and product development become shared work. Price’s current role includes helping entrepreneurs avoid mistakes he has encountered himself, while working with the board and founders on the firm’s direction.
What help looks like before launch
Harbor, an early 25madison incubation, offers a useful example. The team investigated everyday disaster preparedness, attended an expo in Texas, tested a brand called Safeable and studied product features and pricing. It then recruited Dan Kessler to lead the company. Research preceded a finished company; choosing its leader was part of the building process.
Studio team members filled marketing and product leadership roles during the first year. The work included branding, the app, the website and the route to market. Harbor later partnered with ADT, and Citizen acquired it in the first quarter of 2022 for an undisclosed amount. This was an incubation with a sequence of practical tasks, rather than merely a company receiving an investment.
The same problem of reaching customers shaped 25madison’s wider partnerships. An April 2021 announcement reported $60 million raised to date, with Apollo and Endeavor among its backers. Price emphasized how difficult it can be for startups to find beta customers and distribution partners. Established companies could supply places to test a product and routes to sell it.
Connections that have a job to do
That thinking has crossed borders. In June 2022, 25madison and AnD Ventures announced a partnership to help Israeli startups enter the United States. Their work connected product development and market entry with experience on both sides of the journey. An introduction is useful; translating it into customers, hiring and distribution is the longer assignment.
Price also appears in the overlap between investing, media and sports. He is a co-owner and alternate governor of the Atlanta Hawks. In 2022, 25madison Ventures co-led an investment round in TMRW Sports, the company associated with Tiger Woods, Rory McIlroy and Mike McCarley. Price spoke about the opportunity to change how fans engage with sports. The investment extended his company’s work into a field where audiences and technology meet.
For a more modest glimpse of his public life, consider his LinkedIn account of judging a SuitUp student pitch competition. He praised the students’ thinking and recommended co-hosting such an event. It is a small episode, but it brings the venture-studio vocabulary back to its starting point: people trying an idea, explaining it and learning what someone else makes of it.
The next overlooked workflow
Today, 25madison’s stated focus includes applying AI to established industries. Its venture fund invests from pre-seed through Series A; its incubation work includes business software, supply chains and industrials. A separate operation, Propel, makes control investments in lower-middle-market businesses and aims to modernize their operations with AI.
Those ambitions introduce a different setting for Price’s recurring interests. A manufacturer responding to bids or a business coordinating suppliers has existing work to do. Software has to earn its place in that work. The firm presents proprietary technology, customer acquisition and operating support as parts of the same effort. Whether each investment delivers will depend on execution inside the individual company.
Price describes himself as a lifelong learner and acknowledges that some of his businesses have been less successful. That admission gives his advice a particular texture. He has sold companies, run them, invested in them and remained involved after passing daily management to others. The route is untidy enough to be useful. At 25madison, the next question is still close to the one that sent his team out on radio sales calls: what happens when you look carefully at the business already in front of you?