Story
HubSpot acquired The Hustle off a single cold email
Kieran explains the deal originated internally at HubSpot, then a teammate named James Gilbert sent The Hustle a cold email to make first contact. That cold outreach is how the entire acquisition got connected.
“So we went and talked to some media companies and I think it was James, no it wasn't, it was someone internally and said, hey, have you thought about The Hustle? And I told James, who's on my team, hey, you go check out The Hustle, talk to The Hustle. And that's how we first got connected.”
Story
HubSpot bought The Hustle for the talent, not the monetization
Kieran admits the real reason for the acquisition wasn't contextualizing HubSpot ads on Hustle content to drive software sales. It was acquiring the team that knows how to build large, trusted audiences in channels HubSpot wasn't good at.
“We were kind of not being honest with ourselves about why we wanted to. We just wanted the talent who could build audience on those properties, and not the monetization of that into software is really secondary to us. It's like, how do you build big audience in these channels? And so the first time we pitched it, I think I just came at an angle that I thought people would like, but wasn't really the honest reason we wanted to do it.”
Story
HubSpot bought The Hustle for the talent, not the monetization
Kieran admits the real reason for the acquisition wasn't contextualizing HubSpot ads on Hustle content to drive software sales. It was acquiring the team that knows how to build large, trusted audiences in channels HubSpot wasn't good at.
“We were kind of not being honest with ourselves about why we wanted to. We just wanted the talent who could build audience on those properties, and not the monetization of that into software is really secondary to us. It's like, how do you build big audience in these channels? And so the first time we pitched it, I think I just came at an angle that I thought people would like, but wasn't really the honest reason we wanted to do it.”
Fact
In an acqui-hire, the founder being a jerk kills the deal
Kieran says when buying primarily for talent, the biggest risk factors are whether the founder can adapt to a company structure and whether they're a jerk to others. HubSpot debated extensively on Slack how people felt about Sam.
“The other thing is that person like a jerk? Are they being a jerk to other people? Like that's just a thing that's going to, so the founder is a big part of it. And we thought a lot about how people felt about Sam. And we talked a lot on Slack about how we felt about Sam.”
Steal thisIf you want to be acqui-hired, your reputation for being easy to work with matters as much as your metrics.
Number
HubSpot stock went from $14 IPO to over $400
Sam notes HubSpot IPO'd around $14, and by the time of this episode the stock was over $400, roughly a 30x gain for early employees like Kieran who had been there eight years.
$420
HubSpot stock price at time of episode · USD/share
“And now it's $420 or something like that today. I don't— over $400.”
Fact
Buy vs build is really about opportunity cost and speed
Kieran explains a big company buys rather than builds not because it can't build, but because of opportunity cost. Replicating The Hustle's talent, brand, and community would force HubSpot to put its other plans on ice; buying gets from A to C faster from a higher starting base.
“so I don't know if it's that, uh, we couldn't build it, but there's an opportunity cost, right? Like you would have to, we would have to go and find the talent that you found. We would have to go and create the brand around the podcast, the trans community, the hustle community. Like there's just an opportunity cost that we would have to say, okay, all of this other stuff we have planned, we put on ice cuz we're now going to pivot and start to focus on these things.”
Steal thisTo get acquired, position your company as the fastest way to skip the buyer's years of building.
Take
YouTube wins podcasting because search gives long-tail equity
Kieran Flanagan argues YouTube can beat Apple and Spotify at podcasts because its search-driven distribution gives shows long-tail equity. On other platforms a podcast disappears after you listen; on YouTube the search index keeps surfacing it.
“Because it actually has a better distribution engine than Apple, Spotify, any of these other platforms for podcasts, which is search. Because the death of most podcasts is there is zero long-tail equity. You listen to a show and then it disappears.”
Tactic
Recommend podcasts by guest, not just by show
Kieran notes every podcast discovery engine recommends shows because you listened to a similar show, but they all miss recommending shows because you enjoyed a particular guest. That guest-based discovery is a gap YouTube can fill.
“And all podcast discovery engines are predicated on, "Here are other podcasts you like because you listen to this podcast." They all miss out on, "Here are other podcasts you like 'cause you enjoyed this guest." Yes. Right? And I think YouTube can do those things much, much better.”
Idea
STEPN: a play-to-earn Strava that pays you to move
Kieran describes STEPN, a Web3 fitness app that fuses a run-tracker like Strava with a play-to-earn game: you buy sneaker NFTs in-app, then earn crypto for exercising within them.
“There's an app called STEPN. Mm-hmm. And STEPN is so dope, right? It is a, basically it combines like fitness with a play-to-earn game. So what they've done is they've built the actual app like a MapMyRun or Strava where you can log in and you can actually do your exercise and it tracks you. But the thing you can actually do is you can go and buy an NFT within their app. So you can buy these different NFTs, a different kind of sneakers.”
Steal thisDisrupt an entrenched utility app by bolting on a play-to-earn incentive layer that pays users to do what they already do.
Number
STEPN pays $30 per 10 minutes of in-range activity
In STEPN, each sneaker NFT (walk, jog, run) has a pace range; staying in range earns the user $30 via the Solana blockchain for every 10 minutes of activity.
$30
Earnings per 10 minutes of in-range exercise in STEPN · USD/10min
“When you are either walking, running, or jogging. And when you stay within those range, for each 10 minutes of activity, you earn $30 through the Solana blockchain.”
Idea
Learn-to-earn: pay users with tokens to learn your product
Kieran describes learn-to-earn, where exchanges deposit free coins for completing tutorials, and aggregators like Rabbit Hole get brands to pay to run product tutorials that reward users with free coins.
“Learn to earn. So let me bring the listeners through learn-to-earn. Exchanges use learn-to-earn to get you to actually use the exchange and start to trade coins. And if you do those things and complete exercises, they will actually deposit free coins into your account. What a great incentive to get someone to actually start to use your product.”
Steal thisReward new users with tokens or credits for completing onboarding tutorials that teach the core product actions.
Idea
Learn-to-earn: pay users with tokens to learn your product
Kieran describes learn-to-earn, where exchanges deposit free coins for completing tutorials, and aggregators like Rabbit Hole get brands to pay to run product tutorials that reward users with free coins.
“Learn to earn. So let me bring the listeners through learn-to-earn. Exchanges use learn-to-earn to get you to actually use the exchange and start to trade coins. And if you do those things and complete exercises, they will actually deposit free coins into your account. What a great incentive to get someone to actually start to use your product.”
Steal thisReward new users with tokens or credits for completing onboarding tutorials that teach the core product actions.