The Ledger, every show

“So at some point, you're going to start seeing front page headlines in the Wall Street Journal saying, this healthcare company or insurance company rejected one million claims, which it shouldn't have because the AI agent went rogue, or this credit card compan…”

“Today with AI, we are seeing companies. It's not impossible to see a company that gets to a hundred million ARR in two years with less than 50 people, right?”

“Today, in this bucket that I mentioned is a company that gets to a hundred million ARR in two years with less than 50 people. That founder persona is generally not a 1520 years experienced veteran in the enterprise. It's generally a much, much younger persona …”

“These days that this persona of the company you're talking about that get to a hundred million ARR real quick, it's not necessarily the same stickiness of revenue and time will tell.”

“There used to be like, Battery and Neeraj had mentioned whatever the three triples, two doubles kind of a thing triple, triple, double, double, double, or whatever that, whatever the norm used to be that playbook's out of the window, right? Like right now with…”

“At some point, I bet you, 12 months, 18 months, two years from now, the customer will come and say, Shashank, this is very dumb. I'm unhappy. Why? Because you've already done the whole resolution plan. Why do I have to come in and manually hit approve? Just do…”

“A company like Pantomath, infra company, playing in the AI wave, Has to be built in the Bay Area.”

“Now, in the AI wave, I feel if you're heads down and you're focused, you don't know what's going to come hit you from the left or right. You are one anthropic press release away from not having a business ahead of you.”

“Because the traditional model of, like, enterprise reps doesn't get you to a hundred million ARR in two years. You have to do something drastically different for that, right? In fact, a lot of these hot AI startups aren't doing the traditional model. Be it for…”

“So yes, there's, so instead of like, 80% of the playbook being replicable, now in the AI world, only 20% of the playbook is replicable. So I don't know if being a repeat founder has that much of an advantage in this narrow time frame where it's AI.”

“I will never back a founder who can't do a sales demo themselves. If you have to rely on your AE and SE to do a demo, I wouldn't, as a VC, I wouldn't fund you.”

“We feel that data is going to start running with that same amount of rigor because that one incident puts you In bad light on the front page of a publication and it's not a good look for the company.”

“Data is a very crowded category. I don't know if that's the category. If someone's thinking of starting a seed, raising a seed round or pre-seed round to start a company, I don't know if that's the category I'd look at today, mainly because right now over the …”

“The human identities, like in terms of the headcount of most companies will become half that. I don't know. I don't think it will be that drastic”

“Right now automation is moving faster for white collar work and office work and knowledge work than it is for blue collar work in terms of robotics.”

“So, overall, like, listen, investors and capital follows where Entrepreneurs or companies are doing well. So if you build a meaningful company and you're doing well, you can build that anywhere in the world. And as long as you're building it well, like investo…”

“So basically the traditional like swim lanes have all been abandoned. And everyone is just all over the place and you never know who's going to enter in your category.”

“Datadog was a much, much smaller company when AppDynamics was out there killing it. And Datadog today has, what, a 50, 60, seventy billion market cap. I don't even know. I haven't tracked it. That could have been AppDynamics.”

“If you don't take this offer, don't assume the next offer is six months out. Yeah. Assume for the next five years, seven years, you're basically signing up for the next five, seven years of this journey saying, if I don't sell right now, assuming it's a very g…”

“Once Workday approved it, like, I think three months after Workday approved it, they made an offer to acquire us. So we got acquired mainly because of the connectors that we built with Workday and how good they were.”

“Because I believe, and this is one of the thesis we have, is customers won't just want to know what happened, they're like, fix it, and then tell me what happened, right? So the ability to fix it is going to be the key and most critical piece of this whole equ…”

“And very rarely is it a Tableau Power BI issue. It's something upstream somewhere that has failed, but no one knows what.”

“When we raised our series B for this company, revenue wise, we were almost the same, almost identically the same number as when we raised our series B for my last company. Yeah. At my last company, at that stage, we were 75, 80 employees. Let's call it 85, may…”

“Non-human identities will explode that I feel confident about.”

“When you're starting off from scratch and you're an AI native company, it's easier to set up things in a way that you don't need to bring on humans to do that. Whereas if you're a much larger company that has tens of thousands of employees, cutting down 10, 15…”

“Data doesn't break or go bad while sitting at rest. It breaks in motion, right?”

“Anthropic and open AI and everyone wants to get into the services business. It's just areas that you didn't think they'd get into.”

“There are people that are developers, there are people that are AI native developers, and they're not one and the same, right? There is a transition happening, but they're still not one and the same.”

“If I started Wendly five years sooner, it wouldn't work out. If I started Wendly five years later in the AI wave, it wouldn't work out, right?”

“AI agents and giving them rich data to feed off of that's high quality is going to be, is starting to be more of a mainstream problem, but will be a mainstream problem two years from now.”

“The difference between having hundred versus hundred and fifty million is virtually zero. The difference between having 1,000,005 million for a software developer that joins you in your journey is life-changing for them, right?”

“Don't chase the title when your personality is not suited to the title”

“The difference between a visionary and a con man is execution. Right? If you commit to something and you show up and deliver it and it works really well, great, like you'll come across as a visionary, but if it doesn't, Then you're a con man, right?”

“Like, 30% of our customers use Snowflake and Databricks both.”

“Like, at Wendley, I think the first 17, 18, 19 people that joined us all became, like, multi-millionaires when the exit happened”

“When my wife and I were both working, we used to, ah, as our salaries and income went up, we didn't increase the cost of living to a point where, so we were living off of one person's paycheck and the others was all savings.”