The Wisdom Wall

“He'll wake up one day and be like, oh, I want to sell my company, hire a banker. It never works. It's inbound. It has to be inbound.”

“There's a huge, huge market in the M and the M think of it like 10 employees to 2000 employees. They have money. They have pain. The small business products don't solve it. The enterprise companies don't solve. It's too expensive, too hard to put in.”

“our thesis was really obvious in retrospect that you could dramatically drop tack by using consumer-like marketing techniques, inbound marketing, content marketing, freemium to get to these people.”

“And whether you're selling, I think to the fortune, or you're selling to a two person startup, I think freemium's the way to go, uh, in almost any model because no one wants to talk to your sales rep anymore.”

“It's more like a flywheel, where really the customers are your best channel to market. It's not marketing is your best channel to market. It's not sales. Your customers are the loudest voice, ah, in your potential customers' ears.”

“You want to build a great company today, you've got to have a customer experience that's 10 times better than the competition. It turns out on the product side, it's harder and harder to create a moat, a competitive advantage. It's so easy, relatively today, to build new technologies and build new functionality. That's…”

“Products job, they have the heaviest lift in the go-to-market these days. Products should have a quota inside your company. Uh, product is what really convinces people to buy”

“And my lesson is, and he didn't work out for a lot of reasons, but one of the reasons is we hired for a lack of strength. Not for, we hired for Lois Tomlin in our area. We didn't hire for someone who's spiky and I think you should hire for somebody spiky.”

“Boston, the IPO is the finish line. It's so come Valley. It's the starting line.”

“If we both agree on a given topic, of course we do it. If one of us feels really strongly and is willing to lay on the tracks on a topic and the other person's like, I kind of disagree with you, but you feel strongly. We go with the lay on the track person. If we both are strong on it and the opposite ends of an…”

“The thing that fascinates me the most about them is they're all effectively selling the same exact product as their predecessor that they've disrupted. The product's basically the same thing. It's the same music. It's the same cards. It's the same razor. It's the same mattress, basically. But they've taken the friction…”

“The leverage inside of HubSpot, even today, all these years in, like, I always thought it'd be at some point where the product will be built and the leverage is in sales and marketing. The leverage is still in product.”

“If today, 80% of the touches inside your business, inside your flywheel, are human-based touches and handoffs, In the future, I think it should be more like 20%. Automation, bots should do more and more of that work for your, uh, prospects and customers.”

“Today your profile is I-shaped. I'm going to hire a BDOR, they're going to be very aggressive, they're going to be a cold caller, they're going to be an absolute shark, and they're going to optimize the numbers, and they're going to have a sales rep to a different profile. They're all kind of I-shaped. I think in the…”

“It needs to be at least one person around the table. That is, I put up, I gave this person a four, five. I'm going to make this person successful. And if it's all threes, everyone's like, ah, Somebody else will worry about them.”

“these SaaS companies They last. You look at Adobe and Salesforce, both were, I don't know, I haven't looked recently, but three, I call it three or fifty billion. Oracle, you gotta take your hat off to them. It was like, oh, they're gonna die. They're gonna slide. Rose from the dead. The last I checked, they were like,…”

“we do annual three, 60 reviews of the board members and whatnot. And they're really good. They're really effective. And I recommend everyone do that.”

“You, there are two tricks to it. You need to keep your CAC low, which is a hard thing to do, and you can't do that with, with like Major advertising budgets. Um, yeah, you need some sort of viral marketing, freemium motion, product like growth. You need to really get good at keeping cac low. And then you're going to…”

“most entrepreneurs are control freaks. We like to make a lot of decisions, control the boundaries of those decisions, and your greatest strength really as an entrepreneur is that you're a control freak. But that turns into kryptonite and a scale up. Your greatest strength turns into your greatest weakness.”

“In the cases, those three acquisitions are decent sized acquisitions. That's why the CEO, the founder and the CEO mattered. And we wanted to keep and retain that founder CEO. Like interviewing a VP. It's very similar to that. Is it a culture of fit? We think we could see this person here in 10 years. Would we like to…”