Adam Rothenberg

The through-line

Everything he says circles one gap: the distance between doing the work well and making the work pay. He has been interviewing performers since 2008, and by his own account that side of it has never given him trouble. What took years to solve was the business around it. "I've never been at a sticking point with my interviews. I've been at a sticking point with how do I earn an income from doing this" [2]. The arc he describes runs from a decade of quietly wondering whether he could leave a corporate job, to a leap taken in November 2019 on the strength of savings and a promised advertising windfall, to the pandemic erasing that windfall, to a slow rebuild through courses, part-time remote work and paid business communities. He is candid that the destination has not been reached: he still takes outside income because the business alone does not yet cover a living [2].

On the long runway to the leap

He did not grow up planning to work for himself. The idea arrived sideways, at work, listening to colleagues describe side hustles and then watching some of them leave to run those hustles full time. "It always just fascinated me. I was like, 'Wow, I would love to be able to do that somehow'" [2]. That admiration sat unresolved for five to ten years before he acted, a period he characterises as constant private turning over of the same question: how could I do this [2]. What finally moved him was a combination of external signal and internal permission. His podcast had been picked up by a network, there was talk of advertising revenue, and he decided, ten years into doing interviews, that "it's either now or never" [2]. He credits Pink's song Courage, and its line "Do I have the courage to change?", as something he returned to repeatedly while deciding [2]. In November 2019 he "left my cushioned corporate job for this unknown world of entrepreneurship" [2].

The timing was brutal. The advertising he had counted on was largely for Broadway shows and theatre, one of the first sectors shut down by the pandemic, and it vanished within months of his departure [2]. He does not present this as bad luck to be shrugged off. Looking back, "there is a part of me that wish I stayed a little bit longer before taking the leap" [2].

On building the cushion before you jump

The reason the collapse did not end the venture is that he had prepared for a milder version of it. Watching Suze Orman's show and talking to other entrepreneurs, he took away one consistent instruction: while you are still drawing a salary, "saving part of your paycheck" instead of spending it [2]. He started doing that well before he knew his departure date, and that reserve became the thing he lived on when the revenue did not materialise, alongside part-time remote work he picked up afterwards [2]. Asked whether people leaving the military should start a business while still serving, he is unequivocal: "I would say 100% if you can start it while you're in the military to do that," because starting from inside a paycheck was, for him, "the safest way for me to do it" [2].

On the difference between the craft and the business

He separates the two cleanly, and the separation explains where he has spent his effort. Sixteen years of interviewing produced no creative crisis; the crisis was monetisation [2]. His first attempt at a solution came through an entrepreneur group started during the pandemic by an artist he had interviewed, someone forced to pivot because there were no shows or concerts to perform in. From that group he learned the first steps of building a course, and he built one intending to teach podcasting, at the exact moment everyone stuck at home was starting a podcast. It did not sell [2]. He treats this without embarrassment as part of the cost of learning, and his broader view is that you cannot enter business expecting returns to arrive on their own: "you can't be afraid to not learn something," and though learning takes time, each thing learned makes the world bigger [2].

On finding a community rather than going it alone

Asked what matters most when you are stuck, his answer is not a tactic but a room. "The most important thing is to find a community" [2]. His own route was through the Clubhouse app, where he wandered into a podcasting room, spoke from the stage, got guidance that fitted where he actually was in his journey, attended a three-day event and joined the group behind it. He stayed roughly a year, then moved on to the My Sexy Business community run by Kim White, where he remains [2]. The method he recommends is the one he used: "use social media or apps to your advantage to see who's out there, see who you align with," and separately, ask friends who are already entrepreneurs which coach or community they use [2]. He is direct about the counterfactual, saying he does not believe he would be as far along without the group, partly because before he was on this path he would not even have known who to ask [2]. He also values the group as a place to ask without embarrassment, and jokes that he and a fellow member compete over who can ask the most questions [2].

On what counts as an entrepreneur

He calls himself one, without hesitation, and he defines the term by autonomy rather than income. An entrepreneur owns a business, but is also someone who "can set their own schedule" and has the freedom to work as they need to [2]. That definition is what lets him hold two facts together: he still needs outside work because "I'm not making enough from my business to sustain a living," and he nonetheless considers himself an entrepreneur because he now controls how and when that extra income gets earned [2].

On how the interviewing started, and what it has become

The entertainment ambition predates everything. He wanted to work in the industry as a child without knowing what that meant, assumed he might be an actor or a singer despite not being able to sing, then tried standup comedy, enjoyed it, and stopped when it went nowhere, a decision he turns into a running joke about sitting down [2]. He then took a full year to think about what he actually wanted. Reading interviews on other websites, he realised he had his own questions he wanted to ask, and a colleague at lunch suggested he start a blog and ask them. Being in New York, theatre was the largest door open to him [2]. From the beginning he believed in the platform: "I always felt like this would be the thing that would take me somewhere" [2]. The volume has compounded over the years, from a tally described as over 1,500 interviews [1] to 2,200 and more than two million visitors to the platform, with the behind-the-scenes side of that work collected in his book Behind the Curtain: The Mistakes, Lessons Learned, and Triumphs of Interviewing Celebrities, released in January 2025 [2]. He shares the mechanics of the work openly and regularly, something collaborators single out as a privilege to sit in on [1].

Takeaways

• Start the business while the paycheck is still arriving; he says "100%" that anyone leaving military service should launch before they leave, because that was the safest route for him [2].
• Save deliberately from salary before departure: the cushion he built on Suze Orman's advice is what carried him when pandemic shutdowns wiped out the theatre advertising he had banked on [2].
• Treat the creative work and the revenue model as separate problems; sixteen years of interviews produced no sticking point, while earning a living from them produced years of them [2].
• When stuck, buy your way into a room rather than crowdsourcing answers: "the most important thing is to find a community," found via apps and referrals from entrepreneur friends [2].
• Expect false starts. His pandemic-era podcasting course did not sell, and he frames that as the price of learning rather than a verdict [2].
• His working definition of an entrepreneur is autonomy over schedule and income sources, which is why he claims the label while still taking part-time remote work [2].
• The decision to leap came after five to ten years of thinking about it, triggered by a moment where it felt like "now or never" [2].