The Ledger, every show

“And also, why do I think that software and agency multiples will converge? Short answer is I believe the business is The agency business will look a lot better in the age of AI.”

“Parker Conrad, the CEO of Rippling, the HR software platform, tweeted on March 17th that Rippling was suing its competitor deal for running a corporate espionage scheme and stealing trade secrets from Rippling for months.”

“Rippling's general counsel sent a legal letter to three Deal executives mentioning a fake Slack channel called D Defectors that had supposed reputationally damaging information about Deal. Prior to general counsel sending this letter, the channel did not exist…”

“Stripe, they're not doing layoffs. It's not called layoffs. It's what's known as backdoor layoffs, where basically they're requiring their managers to do a rating system of they're, they have to answer a question, would you hire this direct report if you knew …”

“Our clients pay us based on output, and our engineers are paid on output as well. And the reason that is so valuable is we can hire truly the best engineers I've ever worked with, because just as an example, like our best engineer will make a million bucks in …”

“And so I think what was typically considered to be a more quality recurring revenue stream in software products is going to be less true than it's ever been.”

“I think Tenex just as a, an agency business can be a hundred million dollar a year business because I view the opportunity for AI transformation to basically be the GDP of the United States.”

“He basically said businesses that should be venture backed will always have an incentive to raise more and grow faster. He said, my hot take is that all of these amount raised and team size proclamations are extremely short sighted.”

“Yes, claims about health care solutions warrant scrutiny beyond whether or not rich investors get their money back, but Holmes wasn't convicted for defrauding patients. She's going to prison because she ripped off George Shultz, not because her bogus blood tes…”

“Individual content creators should be the highest paid people in a content org. I believe even though we are in an age of content abundance, the percentage of content that is truly exceptional is not increasing at the same rate. It is really hard to create tru…”

“I also think that 99% of creator businesses will fail, not because I'm bearish on the creator economy or creators. I'm actually hyper bullish on them, but I just think a lot of creators are going to launch businesses as a short term cash grab. They're not goin…”

“Brian now operates in an extremely hands-on way, where he is involved in every single project in the company, and the company only does as much as Brian can personally focus on.”

“I didn't have an exact reference point for is that a lot or a little, but he basically shared that on a percentage basis, Airbnb is more efficient than Apple or Google when it comes to how much cash they actually generate for how much revenue they do as a busi…”

“Shopify is a sixty billion dollar company right now. I think OpenAI is thirty billion. You would have to think that the plugins to ChatGPT, which are gaining some popularity now as they're opening it up, is going to be multiples of that.”

“Creator economy, economy funding is going to dry up this year.”

“Elon will no longer be the CEO of Twitter by the end of 20, 23, but Twitter as a platform will be thriving.”

“Tick tock is sold to a U S company.”

“I just think that it is going to take more than Call it, let's call it five years to five X revenue, given they haven't even really proven that they can scale one revenue stream, let alone what I believe will need to be multiple to get it to twenty six billion…”

“I ultimately think within entrepreneurship generative AI is going to make entrepreneurship significantly faster, meaning that the speed to be able to start and test a business is gonna go down, like, by multiples. So I think the cost of entrepreneurship came d…”

“So the whole thesis here is that I believe the next Procter & Gamble is going to be a holding company of creator first or creator led brands.”

“Ben Chestnut and Dan Curzius each owned 50% of Mailchimp. In 2008, Mark Armstrong, the other co-founder, was bought out of the business. Three hundred million dollars was given to employees as bonuses for the deal, and two hundred million dollars worth of rest…”

“We don't charge hourly. Like, we have a fundamental belief that service businesses are going to move away from hourly work, and we think it's starting with engineering.”

“AI is going to have a massive impact on the margins of agency businesses long term. As this technology, being AI, lowers the cost of intelligence, agentic workflows that support smaller agency teams will start giving these businesses the type of leverage that …”

“Like the oversupply of content on the internet, you will have an oversupply of software that is, one, more specific and niche than it's ever been, So there's going to be this whole long tail of software products that are created for the first time ever. Some, …”

“I believe agencies are going to be ground zero for new AI tools and workflows to be built, and if agency owners are ambitious, long-term minded, and commercial enough, they can use the cash flows of their businesses to incubate non-agency products.”

“You have Eric Bond and Elizabeth Yin from Hustle Fund who are bullish on seed strapping. Eric said founders raise a little at the beginning, they get started, and then bootstrap the rest of the way to get big results. That was followed by Elizabeth saying seed…”

“Second, I also think the skills that make human white collar workers valuable will narrow to a few key traits that are uniquely human. The first is trust building through demonstrated empathy and service. The second is taste by having a deep intuition of what …”

“If I remember, by the end of that year, we were spending like, 500 K a month on ads, right?”

“The business grew from a hundred million dollars in ARR in twenty-twenty-two to eight hundred million in twenty-twenty-four and hit profitability with its most recent valuation hitting twelve billion dollars after raising around Anchored by General Catalyst.”

“Peter Levels, a well-known internet entrepreneur on Twitter, launched an AI-coded flying game that has gotten to 67,000 dollars in monthly revenue in just three weeks.”

“Levels went from idea to MVP in 30 minutes simply by prompting Cursor, which is an AI coding assistant that got to a hundred million dollars in annual revenue in less than a year and just raised at a ten billion dollar valuation.”

“I was consistently spending two to three times our monthly revenue and losing money, and not venture capital out of my personal bank account.”

“There is a reason why basically no successful consumer social network has been created in the last five years, and the biggest social networks, Meta, Snapchat, etc., just continue to accrue value and power.”

“There's an entrepreneur I know, and I don't know if he wants people to know this, so I'm not going to say who it is, who built a popular direct to consumer company, sold this company, and he has found a way, he has manually built his stack. So he created a Goo…”

“As technology continues to improve, I would not at all be surprised to see a future generation of this product that not only is mass market, but is delivering society a better new version of phones, computers, TVs, and gaming consoles in a single experience.”

“We have four and a half million subscribers, but if you were to ask me what has been the number one growth driver for Morning Brew, I wouldn't say it's our paid marketing that we did on Facebook. I wouldn't say that it's cross promotions with other newsletters…”

“What I can tell you anecdotally is that I have talked to a lot of founders who regret not selling sooner, and I have never talked to a founder that regrets selling too soon.”

“To cause the board to make this move, a move that Microsoft, OpenAI's biggest investor, found out about one minute before the press release and ended up losing fifty billion dollars in market cap from as their stock continued to trade.”

“I remember when I would tell people that Morning Brew post-acquisition, we scaled from 50 employees in October of twenty-twenty to 300 employees in a year and a half. People were like, oh my god, that is the most amazing thing, and then when I give them the pu…”

“We've had more mental health startups created than ever before, more venture funding for the space than ever before, yet mental health in the United States has never been this bad.”

“In Germany, there are 96 approved COVID tests. So if you want to, in Germany, get tests for COVID, there are 96 different products you can buy. Therefore, the average cost of a COVID test in Germany is like one to two dollars. In the US, there are only three a…”

“Another example is Comcast, who basically has lobbied for years to have citywide Wi-Fi blocked in Philadelphia. So there can't just be general public free citywide Wi-Fi, because of course that would hurt Comcast business.”

“Special ed teachers have the highest burnout rate of any job in America, and they have such a high burnout rate because there is so much government mandated paperwork that has to be filled out for every single student that you have.”

“And so I think asynchronous education or prerecorded courses are not going away and they'll actually continue to be the most common way that people learn online.”

“They ended up having Andrew Huberman promote Momentous Protein on the podcast as an ad read, and for those of you that don't know Andrew Huberman, he has one of the largest podcasts in the world where he focuses on talking about Science and health and things w…”

“What they're doing is only possible because the cost of launches of things into space has come down by 99% since 1970. This business was not possible two years ago or 20 years ago, and it's only become possible because Elon Musk and SpaceX have brought down t…”

“And then Gary Tan, who's now the CEO of Y Combinator, he said of the top 100 YC funded companies, only four Were solo founders, and those founders were able to create their own MVP on their own.”

“Alex McCaw, who is the former CEO of Clearbit, he's a serial entrepreneur, he's one of Matt's clients, he wrote that the idea of not splitting equity Fifty-fifty is key, and he went on to say two of his previous companies were destroyed by a fifty-fifty split.”