The Ledger, every show

“Providing a customer with a highly engaged, instantly available, expert, consistent, fast, charismatic, funny, friendly, personal agent. Available for literally every single customer at every minute of the day around the clock is so much more personal than mak…”

“And I guarantee the reason they're doing that is because women love Waymo because they feel safer.”

“Like, I can't remember how much we wrote down, but we actually have already given away something like fifty million dollars in air or We've reduced the prices for a lot of customers just to give them way simpler pricing”

“When our people saw that we were screwing customers effectively in every direction, it starts to erode the idea that we care about our customers. And then they make other customer unfriendly decisions.”

“You know, obviously, as soon as AI came around, I jumped hard on AI and announced that we were going to spend nearly a hundred million dollars of our own cash on that.”

“When a founder runs away from their business, it is the ultimate betrayal of You know, their heart and the dream that they have now. It's okay to wrap things up and quit when you kind of run away. Like I kind of had to, cause I was sick and burned out and kind…”

“They'll definitely be smaller. They'll be flatter because of that.”

“The abundance of AI is going to make automated things worth zero, just like The value of cheap content on YouTube. Why do people subscribe to some channels and pay more? Why do people pay to rent movies? Because some things have more quality, more beauty, more…”

“I think it's deeply evil to decide what can or cannot be spoken about.”

“Governments become insanely and dangerously powerful when their citizens cannot say what they believe is true or not.”

“In the fullness of time, increasingly powerful and abstract AI will do away with You know, all of the work we need to do today to deliver software experiences.”

“The average resolution rate of our bot is now approaching 50%.”

“The rate at which AI is going to change the whole world is a little overhyped. You know, the raw technologies will be built long before they have real impact on the world.”

“These AI agents will be way cheaper than humans while they're also better.”

“At Intercom, for example, we've been using our, this AI agent fin for nearly two years, and we've not let anyone go, but we've stopped growing the size of our support team.”

“Certain use cases where the distribution of the types of questions is really tight, rather than this big, long, normal distribution of so many different types of questions, will be able to create these tight custom experiences. If you're a Klarina, for example…”

“There is no such thing. Yeah, there's no such thing. Even Apple don't have it.”

“I think it was really, like, acute and fun branding for it. A thing that anyone who's built the company has deployed since the start of companies that, you know, there's nothing new about it.”

“We nearly went public in 2022 and I'm so grateful that we did not... Yeah, twenty-twenty-two. I think it was June, 15. We had a stock ticker that I hated, but nothing cool was available. We had written our S-one, and the markets collapsed.”

“There was literally one person who left.”

“I've never met a founder that's really well-balanced. You can't possibly imagine someone who is grounded and centered, part of a loving community, I'm deeply at one with the universe who then says, I think I'll start a technology company. Most people that star…”

“SF is just a really, really, really, really fucking great place to get work done. And it can be incredibly boring. Everywhere shuts at 10 or 11. People go to bed on time. Again, really great place to be productive. Great place to balance your nervous system in…”

“Telling someone else how to run their very unique business is incompatible with the idea that their goal is to build, you know, a billion dollar enterprise by virtue of the fact that it's different from everything else. Those two ideas are incompatible.”

“Please don't take the egregious sacrifices to everything you value in your life by building an incrementally superior product in a big category. You will go All sorts of nowhere.”

“Their manifesto or principle or values around all of business, or around the core of business, and this is me, I'm not quoting them, this is just my observation, and they're right in this, is that people start businesses to serve their interests and desires. T…”

“Having built a super successful business, build a dollar company, hundreds of dollars in revenue, helped me feel good. But whatever little lacking thing is there on the inside is still present. And really what it's taken for me to chip away at that, as it were…”

“We built a hundred million dollar business with SMB.”

“I'm pretty sure that all other things being equal, if I was able to go back in time and start Intercom again, by this stage, it probably would be 10 exercise only because I now know that I can think bigger, and that simply doing so gives you just so many more …”

“He's no less than my hero these days. Steve Jobs used to be my hero. I would call Elon Musk my hero now. He's so authentically him and so deeply connected to his purpose and not afraid to show up in the world that makes sense to him and is aligned with his val…”

“All the tools that people use to talk to customers were anything but personal, anything but human. They were the opposite. They were transactional, fake, spammy, shitty, bloated.”

“All, all successful CEOs I know of are both skewed or specialized in one area, but also extreme generalists.”

“Basically all our rounds went from first meeting to sign term sheet in a number of days, if not like half day.”

“Fin, which is our AI agent, which is, you know, the future of the business, the thing that will disrupt the old business. It's, you know, growing north of 300%. It took off really fast, like all these other AI companies you hear of the first year. It grew from…”

“We were only six weeks into the launch of GPT. 3.5 when we actually had a beta version of fin.”

“We ran an anonymous employee survey, like, I think, It was 15 or 16 months after I started aggressively working through the org and rebuilding the org and rebuilding the culture. And we had a 98 to 99% approval of management, leadership, and new strategy.”

“When you have this ego identity of yourself about How fucking amazing you are. Then any moment that challenges that is super scary. Anyone who questions it is offensive.”

“Because we're now hiring people who want to be part of something bigger. They're more mature and grown up, more stable and consistent. They're part of, you know, they have a certain expertise and a certain lane they want to work in. And maybe they're not the c…”

“You know, we built, we were the first to come out with an AI agent that would do customer support for you, like actual conversations with customers and closing tickets.”

“In technology, it's all about timing, and it's all about, you know waving successive growth cycles and riding the trends in that moment in time, and then you must reinvent yourself and kill yourself.”

“It's in the hundreds of millions.”

“When I left chiefly because I was sick, also because revenue started to slow, always, also because I was attacked in the press, and I was, like, spiritually crushed, physically crushed psychologically crushed.”

“The San Francisco Freedom Club is designed to hold only epic parties four times a year for people to love freedom and all these other values. We got 3.7 thousand people on the wait lists. We invited 600 people. 500 showed up.”

“When I started Intercom and was raising a seed around in 20 11, every single venture capitalist I met, and you remember that kind of era, told me that you can't build a hundred million dollar revenue business in SMB. Like, it cannot be done.”

“If you invent a new title like this, which might make sense for the world you're building, a lot of people, you want experienced people, that's what they said, who do this job. They're not going to find this role. It's not going to describe what they do. And I…”

“In the 12 months after I went back pull requests, which are the kind of atomic component of shipped code, were up 41% over the 12 months prior.”

“We ran a An anonymous employee survey three months ago. We had 16 questions, and the questions were, you know I agree with the leadership of this company, and they will make us successful. I agree with our new policies. I agree with our new values. I agree wit…”

“We're now seeing it in our numbers, we've got like six or seven quarters of accelerating Aurora growth Our logos were decreasing for two years. Now we've like turned that around and like total number of logos are now increasing for six months.”

“What do we mean by chip on your shoulder? It means you think there's something lacking in you. It's a lack of self-love. It's a sense that you're not good enough. And that you need to possess or achieve something to be lovable or popular or safe or whatever it…”