The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
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Halligan: Morgan Stanley and Fidelity aligned to lower HubSpot's IPO price
“I don't think there was collusion going on, but definitely Morgan Stanley and Fidelity were on the same side of the table trying to get us to sell at a lower price.”
Brian Halligan asserts MBA programs do not effectively breed great entrepreneurs
“I don't think MBA programs are breeding grounds for founders. It's a relatively, like, if you're doing the decision tree on your career and you decide to do an MBA, It's a pretty risk averse move. It's not a risk seeking type of a move. And so I don't think MB…”
Halligan: Companies engineer IPO pops to retain long-term institutional investors
“Part of it also is you want to pop. You want Fidelity and T. Rowe and these long lonely folks to come in and right out of the gate, feel good about their investment. You want them to hold for decades and decades and decades.”
Halligan: Ultra-wealthy CEO compensation must be pegged to net worth
“But you kind of have to peg the comp to the net worth. Same thing with Elon Musk. Like if you paid Elon Musk, like Mary Barra makes twenty nine million dollars a year. You think Elon cares about twenty nine million dollars a year? So you have to kind of comp i…”
Halligan: Current Venture Capital Valuations Are 'A Little Bubbly'
“I think the valuation is very high right now across venture. So we'll see how this thing plays out. I think it's a little bubbly right now”
Brian Halligan names Nvidia's Jensen Huang as CEO of the Year
“I think the CEO of the Year is Jensen. And I like them, but the other thing I like about Jensen is sort of rethinking the role of the CEO. He's rethinking the CEO playbook. I think he's a pretty good inspiration for CEOs out there today.”
Brian Halligan estimates scale-ups experience 50% employee turnover within 18 months
“Most scale-ups Aren't that good at hiring? And I think there's a fair amount of luck involved and have, they don't have a great hit rate. I think 50% within the first year and a half is close to. What most companies are in scale up mode.”
Brian Halligan advises scale-ups to hire leaders three years ahead, not ten
“What you want is somebody who's three years up the ice cliff from you, who's struggled through that same path. What you don't want is someone who's 10 years Beyond it. Or even worse, somebody who's never really climbed that ice cliff.”
Brian Halligan recommends hiring spiky candidates with flaws over safe consensus picks
“I think you're better off with the Mary, and you want kind of spike, a spiky team with some people who have great strengths and great weaknesses, and you want to spike in different directions. I don't, I think you want to avoid that lowest common denominator t…”
Brian Halligan argues managers on performance recovery plans rarely regain team trust
“What I found, and it's a little depressing is. You put somebody on a recovery plan, more often than not, they don't recover, and we end up parting ways to that person. Once they've lost their team, they almost never can get that team back.”
Brian Halligan asserts startup culture and structure inevitably break at 100 employees
“I think it always breaks at a hundred people. At a hundred people, you go from knowing everyone in the organization, knowing a bit about their background, you interviewed everyone to, gosh, you just don't know some of the people. It goes from very flat, like t…”
Brian Halligan claims Sequoia partners work harder than any other venture capitalists
“They work much harder than any other VCs have come across, and they're absolutely paranoid that they're going to lose it.”
Brian Halligan argues small venture capital funds generate alpha, not large funds
“If you look at it though, the small VCs are the ones where the alpha is not the big ones.”
Brian Halligan argues AUM-driven management fees created an oversupply of venture capital
“I do, I think this tendency to grow the AOM because you get management fees on the AOM and limb off those management fees, and there's such a long timeline on, on where the returns are coming in. I think that's just incredibly tempting to general partners and …”
Building a $25B company isn't enough to compete with Sequoia
“Like if I were to go in and try to compete with Andreessen and Sequoia with all those folks, I don't even, that's not, I don't think that's a good enough angle.”
Halligan: HubSpot rejected Morgan Stanley's $24 IPO pricing advice
“We wanted to go out at 25. Morgan Stanley said we should go out at 24. And the reason we should go out at 24 is Fidelity has told us That they're in at 24, they're out at 25. Ok, and you really want Fidelity, because Fidelity has trillions of dollars, and they…”
Halligan: Figma CEO Dylan Field decided IPO pricing, not bankers
“The founders make the decision on what the price is. So Dylan decided at the end of the day.”
Brian Halligan: Direct listings are risky unless you're Google or Facebook
“I think the direct listing is like, you're a little bit scared. You're not going to get those long loneliness. You're not going to properly market it to them. And it's seven percent to the bankers in the grand scheme of things. It's not that much. I think it's…”
Halligan: NYSE and NASDAQ are identical except for ringing NYSE's bell
“You can do NASDAQ or New York Stock Exchange virtually exactly the same, except with the New York Stock Exchange, you get the ring the bell. That's why we picked New York Stock Exchange.”
Halligan: RSUs dampen risk-seeking behavior in tech CEOs compared to ISOs
“It just creates sort of a risk averse behavior in the CEO. Like it's basically cash comp goes up and down a little bit, let's say, but an ISO you're swinging for the fences. Like you've got a strong incentive to swing. And so it's really had a dampening effect…”
Every major Sand Hill Road VC rejected HubSpot's 2009 Series C
“It was in the throes of the recession back in and we went up and down Sand Hill road, like Darmesh and I get off the plane from Boston, landed in Sand Hill road. We're like, we got this. We're going to go up and down. It's like 20 meetings. And we go all 20 me…”
Brian Halligan: Sequoia's strategy of holding post-IPO stock will succeed long-term
“And I think Skoy is really smart. I suspect HubSpot was one of the reasons why they said, Let's hold these companies after they go public. It's back in some cases, but I think it's going to work over the long haul.”
Halligan: Selling software to corporate CIOs is soul-crushing work
“I had spent my entire life Doing the soul crushing exercises of selling to CIOs, and it's just a soul crushing work.”
Halligan: Silicon Valley has a wrongheaded bias against building for SMBs
“There's a big echo chamber in Silicon Valley and big negative bias towards SMB, but you can make it work in SMB. HubSpot and Shopify have shown it. Block has shown it.”
Halligan: Prosumer and Enterprise AI Succeeded, but SMB AI Lags
“The stuff I see, Jason, is there's a ton of prosumer stuff that's working. Lovable's working. Reflet's working. Gamma's working. Like, so many prosumer things seem to be working. And then enterprise is working. You're right. I haven't seen much in between.”
Brian Halligan says acquiring significant wealth does not increase personal happiness
“Money doesn't buy you happiness. I can say I have a bunch of it now. I never had it, and I'm no happier or less happy than I was.”
Brian Halligan admits he was unsuited to lead HubSpot past 7,000 employees
“I don't think I'm necessarily well suited for the next phase from 7000 to 70,000 or whatever it is from twenty billion market cap to two hundred billion market cap.”
Brian Halligan says blending internal promotions and external hires creates winning teams
“And that mix really works, and I think that has worked for HubSpot. We've got a mix of people who kind of grew up through our system, and we hire people from the upside. That's proven to work pretty well, I think. I think that's a good formula.”
Brian Halligan notes Nvidia's Jensen Huang publicly criticizes his 50 direct reports
“One of the things he does is he criticizes in public. Okay, so he's got his team, he's got 40 direct reports, which is pretty weird, or 50 direct reports, and if somebody says somebody disagrees with or does something that he didn't like, he will in front of e…”
Brian Halligan says Elon Musk's primary operational focus is aligning employee vectors
“He talked about how organizations have all their people that are different vectors. And in most organizations, you have some strong vectors, really strong employees, and some less strong employees. And in most organizations, your vectors are pointed all over t…”
Brian Halligan says executives fail by prioritizing their team over the enterprise
“The most frequent The reason I let someone go, and the most common failure condition is I kind of think of this equation of are people solving for themselves, for their team, or for the enterprise? In the failure condition for people scaling up in their career…”
Brian Halligan claims most startup employees hired past 20 people are mercenaries
“I think most of your employees are mercenaries post to 20 employees, largely mercenaries. And I think it's fine.”
Sequoia's Pat Grady caught errors in HubSpot's unit economics during due diligence
“By the way, during the time he dug through all that, he figured out we were calculating unit economics wrong, and he got our head straight, our pricing model. He fixed a bunch of stuff during that.”
Brian Halligan argues secondary liquidity aligns founder incentives with venture capital investors
“It's gonna give you a little Cushion. And personal cushion, which is useful. And it's, it aligns your incentives with your venture capital investors.”
Brian Halligan reveals HubSpot never received a single acquisition offer while scaling
“We had very, very, very little interest. We had no, we've never had like an offer. We had very, very little interest in acquiring.”
Brian Halligan claims MBA degrees are only worth pursuing at top-tier programs
“You only get the pedigree in the network from top tier MBA programs, so I think it's worth it if you go to a top tier MBA program.”
Brian Halligan predicts tech acquisitions under $10B will bypass heavy regulatory scrutiny
“I think you're doing an acquisition under ten billion, unless it's super strategic. I don't think it gets a long look from the regulators. I think those flow through and they happen pretty quickly.”
Brian Halligan: 'Long-Only' Institutional Funds Actively Trade Public Positions
“People would say long only. They're not long only. They do sell. They come in and out of HubSpot. I see them coming in and out.”
Halligan: Zendesk never secured long-only investors due to shaky IPO timing
“Zendesk at the time went out. And it was just, it was timing, and it was just a shaky week that they went out, and they just didn't get, they didn't get the big long onlys, and they had a good story, and they didn't get them, and they never really got them. Th…”
Halligan regrets early HubSpot secondary stock sale to Sequoia Capital
“When we did our round, it was Sequoia. Sequoia came to us and said, we'd like to buy some of your shares in retrospect. It's a horrible financial decision for me, but it was good at the time. And I saw, I forgot a couple million dollars worth of HubSpot shares…”
Brian Halligan: Activist investor horror stories are rare and public markets are rational
“Public investors, like there's so much written about what happened with Zendesk or Autodesk, or these really bad things that happen. It's pretty rare. And I have found that public investors be pretty rational.”
Halligan: Going public will be a top three day in founder's life
“You're exhausted, but the day you go public is going to be one of the top two or three days of your life. It is an amazing day.”
Halligan: Shopify is the only SaaS stock outperforming Oracle and SAP
“If you go from that date and you look at you look at Oracle and you look at SAP, they're both growing, like, 230%. The only SaaS company since August 22 It's growing faster. Shopify. They're growing 300%. So they're outpacing HubSpot, Salesforce, Adobe Box, At…”
Brian Halligan decided to step down as HubSpot CEO after snowmobile accident
“And one of the things I thought about on the bottom of that cliff was, I don't want to be the CEO of HubSpot anymore.”
Brian Halligan says the primary value of his wealth is buying convenience
“Money buys you something, money buys you convenience. It's really the only thing it buys and That's valuable. It's, it enables you to do things, to do less things you don't like to do.”
Brian Halligan says he was most effective scaling HubSpot to 2,000 employees
“I don't think I was at my best from two of us to 20 or 2000 to where we are today, but I think I was kind of at my best between 22,000.”