Ben Lerer

The through-line

Ben Lerer's consistent position across fourteen years of talking about his own company and two decades of investing is that the business you choose to build sets a ceiling on you, and the people you back set the floor. He is candid that Thrillist's founding decision was, in a sense, the one he spent the rest of his operating career trying to escape: "it's almost like I spent 14 years trying to make up for the fact that I started a digital media company instead of something else" [5]. The counterpart to that is a stubbornly people-first investing philosophy, held since the earliest angel cheques with his father and unchanged through nine funds: "it's really People based investing" [4], and in his later formulation, a "talent-driven investor" rather than a thesis-driven one [3].

What has shifted is his tolerance for the founder fantasy. Early on he was chasing scale and revenue diversification with real appetite, cross-pollinating audiences, adding commerce, events, affiliate, licensing [2][5]. Later he speaks admiringly of the opposite discipline, the patient single-brand builder financing off its own balance sheet [5], and of a downturn that forces companies to grow up hard [3]. The optimism remains, but it is now attached to grit rather than to size.

On backing people rather than theses

The fund began as an accident of proximity. He and his father were building companies at the same time in 2005, kept meeting people they thought were smart, and pooled small amounts of money into them; two years later his father emailed him a list of everything they had backed, all of it still alive and raising follow-on rounds, and the answer to "let's do more Investments" was that neither of them had the time or infrastructure, so they raised an $8.5 million fund from friends and family, then a $25 million fund [4][7]. From the start the cheque size was small and deliberate, "150 to 250k checks," with rare follow-ons and a preference for companies "that we think we can help" and entrepreneurs "that we love" [4]. He was explicit that there were no themes: "it's mostly it's all internet," spread across downstack, SaaS, fintech and consumer applications [4]. What he and his father believed they added to technology companies specifically was "an understanding of how to build a brand" [7], and their decision process was fast and instinctive, two people who "follow our guts" and usually agree within a single conversation [7].

The mature version of that stance is a firm that knows its lane and defends it. "We are a zero to one investor," leading or co-leading pre-seed and seed, with a platform built to get companies to the first semblance of product market fit and set up for the next round [3]. He ranks his inputs openly: team first, then market and the team's right to win in it and their view of how that market evolves, and traction last. His reasoning on traction is the sharpest thing he says about early diligence: "if you back a company because of traction in the early days it is inevitable that that traction at some Point's going to sort of get a little fuzzy or hit a wall," the first sales motion runs out of steam, "and when it does you're left with the founders and you're left with that team" [3]. The firm is a generalist by design and category-agnostic, investing across enterprise and consumer despite a reputation built on consumer breakouts [3], and he has discussed how the firm thinks about building competitive moats in venture itself [9] and its posture across nine funds and roughly $1.5B in AUM [10].

He also thinks his operating years are an edge in this work, not decoration: running a company for fourteen years, raising money as an operator, making good and bad decisions at a few hundred million in revenue and 700 to 800 employees, "gives me some Edge in terms of how I assess Founders and how I help Founders and how I empathize with Founders" [3].

On what the current cycle does to companies

He resists the framing that any given vintage is better for starting a company: "it's always a good time to start a company if you are doing it for the right reasons and you're the right person" [3]. But he makes a real argument for hard money as a formative force, and the analogy is parental. "The way that somebody or some or a company grows up I think is significant in the way that it behaves as it gets older it's the same as like a child like how you're raised matters" [3]. Companies born when capital is scarce and the bar is high will be "gritty," "margin and model focused," and more durable, because founding one now is not glamorous and you have to "get the crap kicked out of you a little bit to go do it" [3].

He is unsparing about the preceding period and about his own participation in it. Everyone now says money was free and behaviour was frivolous, "and it's really easy to to sort of Monday Morning Quarterback that," but "to varying degrees of insanity everyone participated in it," himself included; he underestimated the effect of zero rates, the COVID bounceback and government money, and concedes "we knew it was sort of Boom times but but I don't think we realized what boom you know that it wasn't boom times that it was psychotic times" [3]. Nor does he treat the correction as complete or evenly distributed. In some areas the pendulum has overcorrected; in others "lessons have not been learned as I would have expected them to," and he expects people to look back on the current crop of deals the way they look back on 2021, noting that "23 was also a totally insane crazy irresponsible vintage" [3]. His specific worry is non-consensus founders: real companies solving real problems, overlooked by mid and late-stage capital because they are not the flavour of the month, in for a tough go for a while, with the only consolation that if they keep their heads down and build the right way they should eventually get rewarded [3]. AI he treats as a given, the disruption of "every nook and cranny of the universe" that everyone else will talk about relentlessly, and the place where money is sometimes "irrationally easier to come by" [3]; he has also worked through what AI means for founders and for media businesses in later conversations [11][12].

On liquidity, exits and waking up old portfolios

His governing line is "companies get bought, not sold," on the reasoning that it is very hard to decide it is time to "ship off your slightly broken company" and find someone who will pay you anything at all for it, let alone a good multiple [6]. Creating liquidity is nonetheless the job, "regardless of whether or not we have people screaming at us about it" [6]. When a serious outside approach does arrive, he thinks founders should treat it with something close to reverence: run a process, see what else is out there, but remember his partner Eric Hippeau's rule that "your first offer is probably your best offer," and that "there are not all that many moments for companies that are not extraordinary companies to create liquidity." His instruction when one appears is blunt: "don't be dismissive and greedy" [6].

He describes an unexpected new demand on seed investors. Lerer Hippeau is going back into companies from eight, ten and twelve years ago, often as small owners without active board seats, because the later-stage investors are not stepping up: they sit at funds that have raised enormous newer vehicles, are focused on the next trillion-dollar company, and have had turnover such that the people who made the original investments are gone, leaving "some sort of pretty dysfunctional boards with real companies, but a bunch of people asleep at the wheel" [6]. His response is to shake the thing awake. These are good companies with motivated founders, unfair data advantages and lots of customers, but built for a different time, and the work is to reimagine what the company needs to be, "sometimes it is burning the boat, sometimes it's building some new product, sometimes it's changing some talent" [6]. Passivity is the failure mode: "if you just sit around passively and look at your old companies and say, 'Well, I hope these I I they figure out AI.' Uh we're going to be very disappointed" [6].

On content and commerce

He spent years insisting on a distinction most observers refused to make. When Thrillist had more commerce revenue than media revenue after acquiring JackThreads, he pushed back hard on being labelled an e-commerce company, and took responsibility for the confusion: "any investors who thought of us as an e-commerce company, I clearly didn't do a good enough job convincing them why we're not," noting that media and commerce companies carry different multiples [2]. The distinction he drew was about mentality. A commerce company makes money only on the transaction, so "if someone doesn't transact, it's a valueless user"; a media company cares about time and relationship and treats the transaction as meaningless. His reframe: "for us, we say this reader and this buyer are the exact same person. Why can't we treat them that way?" [2]. Subscriptions were always commerce revenue for content companies, and since people no longer pay for content, "you make that revenue up by selling instead of a magazine subscription a physical product" [2]. He drew the line against Fab and Jetsetter, which he called next-generation commerce businesses through and through: "I've never seen them make money except when someone transacts" [2].

His justification for advertising through commerce was that the traditional model taxes the reader. "The problem with advertising traditionally is that it is it's being subjected to advertising is the cost that the user pays for the good content," so "why don't we make money off something that isn't disruptive and super annoying and shitty?" Learning about a cool new brand and getting access to merchandise at good prices beats "having a banner ad smacked in your face" [2]. He conceded it is still advertising, "just a different kind of advertising. It's a better kind of advertising," and defended it on lifetime value, monetising the whole funnel rather than only the transaction [2]. The trust condition was quality on both sides: "there's so many people creating content, there's so many people selling [things] and the ones that are successful are the ones that are creating really good content and selling really good [things]" [2]. And it required owning the stack the way a media company owns original reporting: no drop ship, no outsourced customer service, own technology platform, own warehouse in Brooklyn, own photography [2].

The structural argument he made even earlier is that digital collapses the distance between consuming and buying. On TV, radio, print or outdoor "the distance between consuming content in those environments and actually making a purchase is pretty vast," and digitally "you can consume content and you can buy almost seamlessly," which makes him "a huge believer in Brands finding ways to use content to sell products or retailers using content to engage" [1]. His retrospective verdict is mixed and honest: on the JackThreads bet, "we were right and we were wrong and I think in most of life you're probably right and wrong in in in most decisions you make" [3]. It worked in the sense that a six or seven person business doing a million dollars of revenue was built to real scale, and it worked so well that the business outgrew the marriage: JackThreads "now has its own mission and its own soul and its own kpis and needs its own capital" [1].

On splitting the company, silos and shared infrastructure

The decision to separate media from commerce came out of a process that was about capital and restructuring rather than a sale. What became clear was that distinct investor pools were natural partners for each business, that even investors willing to fund both "turned out to be biased in one way or the other," and that since the businesses had already been operating independently the cleanest answer was to take money from different partners [1]. Asked what came next, he was unusually content not to know: after a fundraise "you're sort of in the trenches for a while in Deal mode," and he was "frankly a little bit happy for a minute to not think about it" [1].

That split sits in tension with a critique he had made years earlier, and he knew it. His model of what to build was Condé Nast rebuilt from scratch: beautifully targeted high-quality content in specific interest areas, spectacular brands, valuable advertising environments, consumers with a tight connection to them [2]. The problems were paper, and worse, that "these brands are uh being built and operated in ivory towers," with GQ and Wired across the hall from each other, competing, not talking, not sharing users or data or selling integrated packages: "This is it's it's madness" [2]. He named the same risk in his own house, that JackThreads and Thrillist and whatever came next would become silos, and answered it with shared infrastructure rather than mere goodwill: only editors were Thrillist employees, only merchandisers and buyers were JackThreads employees, and ad sales, technology, marketing, fulfilment and the customer service centre served everything and could expand to serve more [2]. He wanted brands "to have the brands play real not just play nice together" [2].

On the ceiling of a digital media business

His most developed self-criticism is about scale ambition applied to the wrong asset class. He knew the consumer need firsthand, a young guy in New York whose publications were not built for him, with Daily Candy serving women and nothing for "my demographic of young idiot" [3][5]; it started as a hobby, a nights and weekends project, and he did not think of himself as a media person at all [5][7]. Growth came from a repeatable playbook he compares to a SaaS go-to-market: hire a specific profile of market-leading editor who builds a network of stringers, run national partnerships and content swaps, layer local partnerships with influential voices, magazines and organisations, executed from a central core, taking subscribers from roughly 30,000 in year one to 150,000 in year two to 500,000 in year three [3]. It also had a hard limit: "market 20 wasn't that interesting anymore," New York represented many millions of revenue and Charlotte far less while costing almost as much to run, which is exactly what pushed the company into commerce, events and licensing [3].

The deeper limit was the model itself. He had been investing for five or six years while operating, watching tech leverage in less people-heavy businesses, and asking himself "am I an idiot am I building in the right space" [3]. He wanted a venture outcome, and his conclusion is that the founding choice largely foreclosed it: "a great digital media business is not going to be worth a billion dollars," and getting there requires an aggressive M&A strategy, a diversified revenue base, massive scale and hundreds of millions raised [5]. However hard he tried to make it feel like a software company or a marketplace with real economies of scale, "if it looks like a duck and it walks like a duck like it's still a duck," and at the end of the day it was a media company employing a lot of journalists [5]. He accepts the fair charge that they tried too many things at once, and holds up the alternatives with genuine respect: The Information as highly disciplined, highly patient building off its own balance sheet, and Axios inside his own portfolio as a business that learned from the mistakes of over-financed digital media [5]. He also notes the pattern is universal rather than a media curse, pointing at Netflix now selling advertising as the subscription business slows and predicting theme parks eventually: "we know what this looks like guys" [3].

The commerce ambition itself he still believes in. There is "a massive hole in men's fashion," with women's fashion getting far more attention and the dominant brands being Gap, J.Crew and Urban Outfitters, and the opportunity is to build a men's brand with "the heart of a magazine and the IQ of a tech company," using the internet and data to end up somewhere old school, "creating really beautiful products that people love to wear and feel really proud to own" [1]. On the media side he refused to name a single model, admiring BuzzFeed, Vox and Business Insider for scale and GQ and Esquire for gravitas and longevity, and wanting things from both [1].

On knowing your audience and knowing your limits

He was disciplined about not extending Thrillist into an audience he did not understand. Asked repeatedly about a version for women, his answer was that "we actually at the end of the day don't have the confidence to think that we know how to talk to women," and that the right route would be M&A, finding a brand that understood women the way they understood guys [2]. The low-hanging fruit was adjacency instead: a large trusted audience of guys, 30 to 40 percent of subscribers already using both properties, and expansion into categories the data already showed appetite for. Electronics was the clearest, "we have lots of data to support that because we do infrequently cover those things and we see the appetite for it, but we don't yet have a brand that's deeply credible in that category," which meant investing in Thrillist or building or buying something separate [2]. He preferred to segment by interest rather than age, even though the JackThreads reader skewed younger and better dressed [2].

He was equally disciplined about not letting his own taste stand in for the audience. "I try to not read Thrillist and be like, 'This article is good, so this article is good.' We let the data do the talking. We let the audience do the talking to figure out what's working," and he explicitly hoped Thrillist had not aged along with him [2]. Editorial independence was structural, with his co-founder as editor-in-chief running a traditional editorial infrastructure and pushing back on advertising [2]. Early on, the whole strategy rested on trust as the metric: with $1.8 million raised from Pilot in 2005-2006 and an agreement with Bob Pittman not to spend any of it on marketing, the two tests were whether great content grew the audience organically and, "almost more importantly," whether people actually acted on it, went to the restaurant, went to the store, bought things [2].

On New York, and the origins of the fund

He is direct about how unfashionable the New York tech scene once was: "five years ago it wasn't cool to have a tech startup in new york," and when he told friends he was leaving his job to build Thrillist "they all looked at me like i was a fool," whereas now "founders are like rock stars" [7]. He never argued New York beat Silicon Valley for the best technologists, only that it was getting stronger and more viable, with plenty of good tech brands being started there [7]. His fund is a direct product of that thinness. The deal flow came from being a founder in a town without many founders, and the firm grew as the city grew: "we grew with New York New York grew and we continued to grow," to a 20-plus person team all based in New York [3]. He describes that early ecosystem as underdeveloped, collaborative, fun and full of underdog energy, and the payoff as writing first cheques into companies that either got big or generated a great deal of attention and talent [3].

On "everyone's a fraud"

The line he inherited from his father is his answer to imposter syndrome and, effectively, his theory of career-building: "remember everyone's a fraud" [5]. His father built without a blueprint, without an amazing mentor or teacher, and simply figured it out; the practical residue is work hard, treat people well, and hopefully end up with some luck in the right place at the right time [5]. Lerer applies it to himself as permission rather than as cynicism: "I've you know in many ways sort of modeled my career after him which is going and doing things that I don't really have the right to do but that like nobody has the right to do like everyone's just figuring it out," and "anyone who thinks they have all the answers is insane and and probably wrong" [5]. It also colours how he narrates his own beginnings, where the honest reason they raised only $1.8 million was that "we didn't know how to raise any money" and had a small vision, a daily candy for dudes, with commerce nowhere in the picture [2].

He rejects the Oedipal reading of family entrepreneurship outright. Surpassing his father is "really not a driving force," because a genuine family partnership means "neither of us are like covering our own assets" and his father would simply hand him the win; the Succession dynamic is "the most foreign possible kind of family Dynamic I could ever imagine" [5]. He is similarly generous about his sister, who he thought of as an academic and an animal lover rather than a business person, and who he says built the best media business of the three of them in far less time [5]. His personal board is small and long-serving: Bob Pittman, his first investor, a steady source of advice over decades; his partner Eric Hippeau, who has seen more cycles; and a group of founders he backed early who have since become mature operators and close friends, a relationship where "the tables turn a little bit and you end up sort of getting more than than you give" [5].

The skills he says he is actively working on are not commercial. First, listening: he describes himself as an "extrovert type A" who talks too much and is trying to do more listening and less talking. Second, presence, which he calls harder because of Zoom and phones, and which he traces to a trip to Japan where the intentionality of everything from a meal to a public restroom struck him as a culture built around "really appreciating every moment," in contrast to the "go go go U.S culture" he admits he has been guilty of, including the belief that if you are not growing you are dying [5].

Takeaways

• Rank team and market above traction at seed, because early traction predictably stalls: "when it does you're left with the founders and you're left with that team" [3].
• Treat a scarce-capital environment as formative rather than merely painful; how a company is raised shapes how it behaves, and hard cycles produce gritty, margin-focused, more durable companies [3].
• Do not plan on selling a struggling company. "Companies get bought, not sold," so when a serious approach arrives, run a process but "don't be dismissive and greedy" [6].
• Seed investors should actively re-engage decade-old portfolio companies where later-stage boards have gone quiet, and push founders to reimagine the business rather than hope it drifts into relevance [6].
• Content and commerce work because digital collapses the gap between consuming and buying, but only if you own the whole experience: no drop ship, no outsourced customer service, own platform, warehouse and photography [1][2].
• The category you found in sets your ceiling. A great digital media business will not be worth a billion dollars without aggressive M&A, diversified revenue and hundreds of millions raised: "if it looks like a duck and it walks like a duck like it's still a duck" [5].
• Refuse to extend into an audience you do not understand; when Thrillist was pushed toward women, the answer was that they lacked the confidence to think they knew how to talk to them, and that the route would be acquisition [2].
• Build brands to share infrastructure rather than sit in ivory towers, keeping only the truly brand-specific roles inside each brand [2].
• Combat imposter syndrome with the working assumption that "everyone's a fraud" and nobody has the right to do what they are doing [5].