Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
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Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Yeah. Well, one thing that's stuck through many chapters has been the inbound conference, a conference that over a 100,000 people go to. You can give me the stats, like people like Barack Obama speak at it. It's sort of a pilgrimage for people who work in marketing. Like, uh, how did this happen? Why did you do it?
A So in the early days of HubSpot, the way we described ourselves to the venture capitalists like yourself was, At the time, Salesforce just said SFA. Salesforce.com is the sales. That's what's about is the marketing. And the good thing about that is it's stuck on VC's heads. It's like, oh, that sounds like a good thing. Like, we would go to Dreamforce every year. And by the way, we'd sit at Dreamforce and we'd sit there being like, God, I hope they don't announce a marketing product this year. Literally, the two of us would sit there like, fuck, please don't announce a marketing product. Anyway, we would go and we said, that seems like a decent idea, but it's more user conference. Let's create like a community thing that people will come, even if they're not HubSpot customers. So we said, let's create this inbound thing. And we just gave it a go. We, and we had a room of 400 people in the Marriott and Kendall Square. We invited Seth Godin and David Meerman Scott and Brian Solis. These folks are still floating around where, who are early sort of acolytes. They may or may not call it inbound, but basically the same ideas were coming out of their mouths. And we sold out in like five minutes and it was really good. And so then we sort of got on the treadmill and just kind of kept doing it every year. I really enjoy it. Like we had my, I'll tell you, we had some amazing speakers like…
AI assessment note: “Let's create like a community thing that people will come, even if they're not”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q of my favorite HubSpot people. So JD Sherman, um, your COO for a while, at certain points managed, you know, large parts, entire organization at HubSpot, um, and was there for a long time. In terms of all the founders that listened to the podcast, many at some point think about hiring a COO. How did you guys decide to do this? What advice would you have for, for people?
A We hired. So after we closed our Sequoia round, we bought performable and we stopped like tracking expenses. We just started spending like drunken soldiers and we just got distracted. It was a really good round. We had Sequoia, Google and Salesforce in the round and We just kind of took our eye off the ball. We had never missed a quarter, and we missed that quarter on the revenue side, and missed the expense side by a country mile. We had a couple long-time board members, Larry and David Larry from Journal of Catalyst, and they were like, you know what? You could use some help. I was like, what do you mean today? We think you should hire a COO, and I pushed back. I was like, nah, I got this, I got this. Like, not really. And so, They're like, go see if you can find one. And so I interviewed a bunch of people and I met JD and JD was a long time IBM person, which is like, oof. And, and then he was at Akamai for a long time. He was a CFO at Akamai.
AI assessment note: “We think you should hire a COO, and I pushed back.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q You've been looking at how businesses engage with customers for, for 20 years, and you've been really, really right about some of the macro shifts. Like how, what do you think is going to happen about how we engage or how, how customers buy?
A I think one of the obvious things is how much better these things are getting and how quickly they're getting better. And everything you've got on your website and every social post you've ever put out there, it's consumed and understands it. And so I think if Google, someone goes to Google, they ask a question, it gives you a list of blue links, click that blue link, that, that prospect lands on your website. Um, but you think of chat GPT, yeah, they keep asking questions about you. They don't necessarily have to go to your website. Um, and so I think that'll be a big shift and having lots of high quality content is going to be important, but I think one of the things that's not going to work is using AI to just create tons of content. I think Sam Altman and all the people building the, the other models are going to look at similar signals to Google. They're going to say how many links are into the site with the power of the links, other signals of credibility. You've got to create really, really, really high quality content. If you want to get found in there. The other thing I think people need to do is give folks a reason to come to your site. And I've been a big advocate of. Ungate everything, you know, you used to have all this white papers, all this crap behind, um, Gates and I'm like, get put it in your blog, whatever. I actually think maybe Gates come back a little bit …
AI assessment note: “think of chat GPT, yeah, they keep asking questions about you. They don't necessarily have to go to your website.”
Answered raw tape
D 4 · C 5 · P 5 · Cm 4 4.55
Q Okay. So Brian, you're, you actually started, I think, as a sales leader for PTC, like famous enterprise sales organization in Asia. How did you go from that to the founder of HubSpot?
A I actually started as PTC's first BDR and its headquarters in Boston and moved into sales and channels. And then They, they were, the company was going incredibly well, and they moved me over to Asia to start it. So I moved to Japan, and I lived in Hong Kong for a while, and, um, yeah, I worked there for 10 years. It's a really good run. Um, but I just think of my, I have three chapters in my story. Chapter one was PTC, enterprise sales, eat your young, really a hard-charging culture, sales-driven culture, um, terrific company in its own ways, um, unusual culture, tough place to work. I left there, and I had a second chapter that couldn't be more different. Started the sales organization for a company no one's heard of anymore called Groove Networks. And Groove's famous for its founder, a guy named Ray Ozzie, who's the father of Lotus Notes. And it did okay. Like, we got the twenty million in revenue, and Microsoft bought it, and it's like a little part of SharePoint now. But it really didn't tip. And what was interesting about that company and learnings for me Ray was a product person, and the company was very much a product company, and he referred to himself as a social anthropologist, which I thought was really interesting. He sort of watched where technology was going, and he thought about how human behavior would change, and then he tried to create something kind of in th…
AI assessment note: “I just think of my, I have three chapters in my story.”
Answered raw tape
D 4 · C 5 · P 5 · Cm 4 4.55
Q Okay. We had dinner at some point where you talked about the investment in culture at HubSpot and how you and Dharmesh thought about it. It shows up in the results. You're, you guys are repeat winners on Glassdoor in terms of both like CEO to work for and best place to work. How?
A Okay. The early days of HubSpot, um, we didn't want to talk about culture, HR, any of that stuff, the first three years, like Culture was a poor letter word. No one should bring it up. You can't measure it. It's soft. And then I joined a CEO group about three years in, and I largely joined that CEO group because one of the members, uh, was a guy named Colin Engel, who is the CEO of iRobot that makes those Roomba vacuum cleaners. I would describe my relationship with Colin in two words. The first is man. The second is crush. A major man crush on him. I showed up for the first meeting. There's nine CEOs around the table and, uh, sat right next to Colin. Uh, and I didn't know this, but they picked a topic and they would just go very deep into one topic all day. And it's like CEO, uh, couch down. And the topic of the day was culture. I was like, is that what this, this is such a waste of time. Can't believe I've spent all day talking about culture. And so I didn't say anything all morning, and I didn't, sitting next to Colin at lunch, asking him a question about product and innovation. And Colin said, uh, you don't like this culture topic, do you? I said, no, I think it's a waste of time. He said, culture is how you scale your company. Culture is how people make decisions when you're not in the room. Ok. Took note, just paid in the afternoon. And then that next day, I saw Dharmesh …
AI assessment note: “Culture is how you scale your company. Culture is how people make decisions”
Partly raw tape
D 2 · C 4 · P 5 · Cm 4 3.65
Q We have some friends in common, Elias and David, who were acquired into HubSpot by their own startup at the time for Performable. I don't know if you guys did any other acquisitions that were important. This one felt important. What, what did you learn about acquisitions from this?
A That one was important, and I could kind of give you the background on that. When Darmesh and I started it, we were really about the top of the funnel. How do we help people turn total strangers into visitors to their website and then turn them into leads? But we hadn't really thought of, like, a database, segmenting the database, drip campaigns by email. Um, honestly, we weren't that passionate about it at the time. We didn't have deep domain expertise about it. And so little known fact at the time, we actually closed around with Sequoia and some of the proceeds we're going to use. We're going to acquire a company in what we call most of the middle of the funnel, the database size, segmentation, drip marketing, all that stuff. Uh, we made a bid for par dot. Couldn't get to a number. I went out to Marketo CEO and proposed Marspot to merge the company's merger of equals. I offered them the CEO gig. They weren't interested in the time.
AI assessment note: “I could kind of give you the background on that”
