HubSpot

Dharmesh has zero direct reports after 15 years and 4,000+ employees

In a co-founder heart-to-heart, Dharmesh and Brian Halligan agreed Brian would be CEO and Dharmesh would have no management responsibilities. Believing in amplifying strengths over fixing weaknesses, he's never had a single direct report despite HubSpot growing past 4,000 people.

“I'm a big believer in take your strengths, whatever they are, and put like all your energy into kind of amplifying those strengths and getting really, really good at that thing. And don't worry about your weaknesses all that much. So I don't want to worry about my weakness managing people. And so we have over 4,000 people at HubSpot. I have zero direct reports.”

Natural-language layer for B2B software: bigger than mobile

Dharmesh's second big idea: a translation layer that lets users just say what they want ("remove the background", "how many signed up in 90 days") instead of learning clicks and menus. He calls it a megatrend bigger than mobile, with B2B reporting tools the obvious first target.

“If you're in HubSpot, you should, I want, it's like, you know, "How many new people signed up for our Service Hub product in the last 90 days?" You should just be able to type that question in, 'cause that's your intent, not like, "Oh, go to HubSpot's reporting tool, build this dashboard, pull out here the 3 columns you want, whatever, and get to the thing you want."”

Steal thisWrap an existing complex B2B tool in a natural-language layer so users state intent instead of learning the UI.

Website Grader: build a diagnostic tool that makes people realize they need you

Dharmesh built Website Grader as an internal tool to score prospects' sites, then put it online where tens of thousands used it. The lesson: a free diagnostic for your industry isn't a lite version of your product — it's the thing that makes buyers realize they have a problem.

“the power of building a diagnostic tool for your industry is immense, right? This is the thing that— so Website Grader was not the solution. So it's not like a freemium thing. It's like, oh, we're giving you a lightweight version of HubSpot. It was the thing that made you realize you needed HubSpot, and that was super valuable.”

Steal thisBuild a free diagnostic/grader for your industry that scores the prospect's current state and surfaces the problem your product solves.

HubSpot raised $105M in private money before IPO

Dharmesh confirms HubSpot ran the classic venture-backed playbook, raising $105 million in private capital before going public — intentionally, because the founders wanted to swing for the fences.

“$105 million in private money before we went public. Yeah. HubSpot's a classic venture-backed playbook company.”

Be rich, not king: HubSpot's founders chose to swing for the fences

Dharmesh and Brian agreed from day one they didn't want a single or double — at every fork they'd take the path with the higher chance of a spectacular outcome, accepting they might crash and burn. They weren't worried about dilution or control; they wanted to be rich, not king.

“we didn't want a single or double hit, right? We wanted to swing for the fences. And either we do this and we're good at every point that we have a decision to make, a fork in the road, we are going to take the one that gives us a higher chance of being the spectacular outcome, even if that means we're possibly going to go down in crashing, burning flames, right?”

Sam's portfolio: 90% index funds, concentrated HubSpot + Airbnb bets

Sam breaks down his actual holdings: bulk of liquid net worth in publicly traded HubSpot and Airbnb, the rest in the S&P 500, plus planned startup and real estate allocations. A rare candid look at how an exited founder actually invests.

“So right now the bulk of my liquid net worth is in publicly traded companies. Um, I own a bunch of HubSpot right now. I own a bunch of Airbnb. Besides that, I don't own anything else above $50,000. Uh, it's all in, um, so you're super concentrated in those two companies basically. Yeah, but then I have more money in the S&P 500.”

Every big platform with an app store breeds winners

Shaan's broader thesis: any platform that reaches critical mass and opens an app store will spawn winners. Beyond Apple and Google, he points to HubSpot, Salesforce, and Slack as under-discussed platforms where frictionless, revenue-generating products can be built.

“Like, once these platforms reach a critical mass, somebody's going to build something that's frictionless on top of it, that is able to generate revenue. So I think there's, there's money to be made in the unconventional app platforms that you don't really think about first.”

Steal thisBuild on an under-served platform app store (HubSpot, Salesforce, Slack) before it's crowded.

HubSpot: $1B revenue, ~30x revenue multiple vs real estate

Arguing software beats real estate on multiples, Shaan notes HubSpot does $1 billion a year in top-line revenue and is valued around $30 billion — a 30x revenue multiple — versus real estate trading near a 5-6% cap rate.

“HubSpot is doing $1 billion a year of top-line revenue. That's not profit. And, you know, even on the revenue, I think HubSpot's valued at what? It's like a $30 billion company or something like that. So it's a 30x of revenue in that case. So software has better multiples than real estate.”

Media companies buying media: the new acquisition playbook

Shaan frames a pattern: non-media companies acquiring media/community brands to own an audience. Examples include Robinhood buying Snacks, Stripe buying IndieHackers, HubSpot buying The Hustle, and Spotify buying The Ringer.

“Robinhood bought, uh, Snacks, which was like a kind of a media company. So Robinhood, this exchange, not a media company, buys a media company. Stripe bought IndieHackers, right? Stripe, not a media company, bought IndieHackers, this community of kind of makers. HubSpot buying The Hustle. And there's a few other ones that are actually somewhat prominent. Spotify buying, let's say, The Ringer or things like that.”

Steal thisIf you run a software company, consider buying an audience instead of building one from scratch.

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.”

Anatomy of a cold email that lands an acquisition

Sam reads the actual cold email from HubSpot's James Gilbert: a personalized opener acknowledging Sam's Lyme diagnosis, a clear ask about acquiring content businesses, and shared interests like self-storage and home ownership to build rapport.

“hey, Sam, I've been a longtime follower of you. Sorry to hear about your recent diagnosis of Lyme. I know it's pretty hectic, but hope you're okay. And I like that. So he goes, so we're looking to partner or even acquire content businesses where we think it'd be a right fit. And then basically he says, uh, is this something you would be interested in talking about? And he said, by the way, I'm also interested in self-storage and I think home ownership is not an investment, but a consumption point.”

Steal thisOpen a cold email with a genuinely personal note, then dangle a shared interest before making your ask.

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.”

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.”

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.

Once a buyer has sunk time and salaries in, they're committed

Sam's friend Jack told him that once HubSpot's executives, CMO, and legal teams had spent significant time and money on the deal, they were psychologically and financially committed. No one wants to look dumb after pitching the board, which gives the seller more leverage than they feel.

“And he goes like, dude, like they've spent all this time on this. They want this. If they're saying they want it, they want it. It's going to take a lot to mess it up at this point. And I was like, oh my God, you are so right.”

Steal thisRemember a buyer's sunk cost is your leverage; once they've pitched their board, they badly want to close.

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.

“And now it's $420 or something like that today. I don't— over $400.”

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.

Sam wanted WeWork or LinkedIn to buy The Hustle, then HubSpot cold-emailed

Sam recounts rejecting private-equity and legacy-media suitors because they felt like a culture mismatch, and how he'd long fantasized about a tech company (WeWork, LinkedIn, Salesforce) buying The Hustle. HubSpot reached out unsolicited last fall and the plan clicked.

“And so in my head, I always thought, you know who should buy us? WeWork. I thought WeWork should buy us, like when they— before we found out that they weren't that great. And then I thought, um, LinkedIn should buy us. And then I started thinking, oh, what about like a Salesforce or like companies like this? And then last fall, HubSpot reached out to me and I was like, oh my God, this is finally happening.”

The Hustle's playbook: build a big free list, profit on ads, reinvest in high-margin products

Sam describes The Hustle's day-one vision as a flywheel: grow a large email list of business-minded readers, monetize early with advertising, then use those profits to launch higher-margin direct products like Trends and eventually invest in members' companies.

“We said that we wanted to build up this really large email list and we're going to do it for like these, this entrepreneurial business-minded person. We're going to make profits early on, which we did with advertising. We had about an 8-figure advertising business. And then as we grow, we're going to use those profits to launch more stuff that we could sell directly to them.”

Steal thisBuild a free audience first, monetize with ads, then plow profits into high-margin products you sell directly to that same audience.