The Ledger, every show

“And I was arrested for felony and misdemeanor assault of my now wife and mother-in-law who were Trying to keep me from running into the street naked out of my apartment on ninth street.”

“90% of the alpha for Chicago-based venture firms is created on the coasts, right? And 90% of the capital that the leading Chicago companies raise is from the coasts.”

“Look, I think there's room for the next great American rooted social network right now. And I believe three things about it. Number one, it's going to be AI native. Number two, it's going to be focused on actual friends and your IRL local life. You're in real …”

“All the money is going into profitable wholesale led brands now, not into DTC brands.”

“And our second most profitable were our retail stores, and those two businesses' profits were funding losses from the e-commerce business, which is a wonderful paradox to the way that we conceived of the company.”

“The future of e-commerce was gonna look a little bit like the history of Netflix. That a platform that was streaming other people's content and distributing other people's content would vertically integrate and start to develop their own proprietary content.”

“Our most profitable business became Nordstrom. And our second most profitable were our retail stores, and those two businesses' profits were funding losses from the e-commerce business, which is a wonderful paradox to the way that we conceived of the company.”

“Three percent of the general population has some form of mood disorder, most commonly bipolar disorder. We think that index is seven to one in entrepreneurs. So we'd be talking about one in five”

“We've never had a hundred billion dollar enterprise value tech company built here in Chicago.”

“When we were nine years into building Bonobos, the cliff notes on my story were we had over a hundred million of revenue. We had 600 plus employees and I ended up in the psych ward of Bellevue because I had untreated and unmedicated bipolar type one.”

“If you think about why, why did something like Warby Parker work or Harry's work? It's because they price disrupted Luxottica and Gillette respectively.”

“The truth is that 80% plus of retail is still spent in brick and mortar stores.”

“And that was this genius insight that actually the way to do this is to make pants with a curved waistband, which would bring in the pant around to your waist in a way where the overall shape looks, looks great. And that hadn't really been done in a meaningful…”

“Because we were fifty-fifty partners. You know, I had the title of CEO, but Brian had a ton of business acumen, and so it really was a partnership of equals, and it becomes difficult to figure out who makes the call.”

“We had enough cash in the bank, I thought, to make payroll, but then we had, I guess, promised a supplier through a letter of credit, and we were about Eight days away from not making payroll, which is not an inspiring moment for your employees.”

“For 72 hours, there's a really big reaction and an availability bias of the most vocal people. And then business returns to normal. The vast majority of people don't think about this stuff that much every day.”

“And that was this genius insight that actually the way to do this is to make pants with a curved waistband, which would bring in the pant around to your waist in a way where the overall shape looks Looks great. And that hadn't really been done in a meaningful …”

“They said no at first. And, you know, said, hey, like, you need to work for the shares that you've got. And then, you know, ultimately I just wore them down, and I got some alternative perspectives from people in the venture capital backed company space, and s…”

“That's live in Chicago, Austin, San Francisco. We're going live in New York and LA. We got other smaller markets percolating like Columbus and Milwaukee and Atlanta.”

“We've got about 800 of those community builders on our app right now”

“There's a million alcohols to compete with, but in the shot culture, there's like five.”

“Like Ipponobos, we didn't do a layoff until our 12th year.”

“And we started Bonobos, right? And right before the great recession. And so, oh, eight, oh, nine, 20, 10. We had to raise our first eight million from a hundred plus investors.”

“Five years ago, there was like a hundred million of venture capital that went into mental health tech. Last year, I heard that was five and a half billion.”

“We sold the company for three hundred million dollars”

“One day, we had a pants party at our house, and I think we sold 16,000 dollars worth of pants that day, and that was when I kind of looked at him.”

“He said, at three, we'll take a 100,000, but if you dropped it down to two, we'll take the whole round.”

“Well then I went to see the other professor from school who is an amazing business person named Andy Ratcliffe, one of the co-founders of Benchmark, and he also offered to invest, and he was willing to do it at the three million dollar price”

“So we properly launched BonobosPants.com in October of oh seven, and we did 10 grand that month, then in November we did 20, December we did 30, came back from the holiday break in January, and we did no sales for the first five days, and I thought, oh my god,…”

“And then I had another 90 conversations like that over the course of the next couple months, and pieced together another round, and, you know, we ended up raising our first eight million from, you know, over, over a 120 investors.”

“And if you look at our chinos business, we've got 36 waist and inseam combinations, four different fit silhouettes, and we might be running 15 to 20 colors. So if you do the math, that's four to 5000 variants.”

“When I graduated business school, I had 3000 dollars in the bank and 160,000 dollars of debt. And I started a company with that balance sheet.”

“One day, we had a pants party at our house, and I think we sold 16,000 dollars worth of pants that day.”

“I went to see the other professor from school who is an amazing business person named Andy Ratcliffe, one of the co-founders of Benchmark. And he also offered to invest, and he was willing to do it at the three million dollar price”

“So we properly launched BonobosPants.com in October of oh seven, and we did 10 grand that month, then in November we did 20, December we did 30, came back from the holiday break in January, and we did no sales for the first five days, and I thought, oh my god,…”

“We had, I guess, promised a supplier through a letter of credit, and we were about Eight days away from not making payroll”

“We ended up raising our first eight million from, you know, over, over a 120 investors.”

“When I graduated business school, I had 3000 dollars in the bank and 160,000 dollars of debt, and I started a company with that balance sheet.”

“The acquisition conversation with Walmart wouldn't come till about half a year later, so we were more in the warm-up phase.”

“I have this offer from a venture capital firm, which was a firm up in Seattle called Maveron, and I said, but I don't think I'm going to take it, because I'm going to sell pants on the internet.”

“Seven guys bought three pairs of pants, six guys bought two pairs of pants, only one guy didn't buy anything, and it was at that moment that I decided, we need to build this company in New York.”

“We did two million in that first year, and of, kind of, full operations in a way, and then four in a nine, and then we were heading towards seven or so”

“There's no Grade disclosure to employers. So they remove the competitive dynamic of how you do in your classes.”

“Seven guys bought three pairs of pants, six guys bought two pairs of pants, only one guy didn't buy anything, and it was at that moment that I decided, we need to build this company in New York.”

“We did two million in that first year, and of, kind of, full operations in a way, and then four in a nine, and then we were heading towards seven or so”