Andy Dunn

“Well, at one point the team was 23, and the age of AI it's now 12, and we've seen what you guys are talking about, which is just a massive collapse of product design, engineering, and even go to market, where people can do so much more, and so, you know, we di…”

“I did 15 pitches in Chicago, because I wanted to raise our Series A from a Chicago venture fund. I got 15 no's. I did one pitch on the West Coast with Kirsten Green from Forerunner, and we got a term sheet within 48 hours.”

“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.”

“Because the only way to get off these phones is through our phones. The people that were influential in hooking us on social media are very well positioned to say, guys, let's get out.”

“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 …”

“I'm a, I'm an investor, angel investor in a brand called Carraway. It's pots and pans and kitchenware. And what he did that I thought that was so smart is he actually built an army of something like 3000 Instagram partners. It was just value exchange for free …”

“And if I could go back and do bonobos again, I wish I understood how much better it is to dilute your brand by giving the equity to someone like that than running Instagram ads.”

“I spent 13 years building something that I think in retrospect is an impossible business model, which is DTC apparel. Like, I don't actually think it works. Like, the math doesn't work on it, because it's too expensive to acquire, acquire customers, right?”

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

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

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

“We ended up with a handful of investors that invested, like I mentioned, Kirsten Green from Foreigner Ventures and a handful of other amazing people that stepped up and some of my friends from business school, like the Warby Parker founders the founders of Har…”

“Andy, and I had also hit it off. He became an early investor, founder of Bonobos, sold it to Walmart for three hundred million plus.”

“When you're bumping up against people who care about something more than you do, that's just a good sign that you haven't really found your swim lane yet. You should be swimming in a swim lane where you feel like you can go the fastest and you want to go the f…”

“No, I w I wouldn't have done it. If I could go back, I think there's so many Problems with raising money.”

“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.”

“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”

“Just go talk to one person that isn't your boyfriend or mom or coworker. Someone whose sole job is to find a way to get you healthy. And that is the best investment that you can make.”

“And I have to say, it is such a profoundly humbling, meaningful, good, And challenging, sometimes maddening experience to realize that all these years you were, you know, woe is me, being a CEO is so hard, and it actually turns out that being an employee in a …”

“Was Mark Laurie, who I think is the best entrepreneur on the East Coast.”

“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.”

“I think that hypomanic state is almost indistinguishable from an entrepreneur who is quote unquote on, right?”

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

“It's easy to explain away The mood swings you might experience as a person with bipolar disorder, if you're also an entrepreneur, as being due to the fact that you're an entrepreneur, when there's something else that you need to be dealing with as well, that i…”

“What I did, Guy, was I told a small cohort of people who just had to know I told our general counsel. I told our head of HR. I told our CFO. I told my assistant.”

“I'll still be seeing a doctor twice a week, And twice a week is a lot, right? Seeing a doctor twice a week is a lot, but I do it because I don't want more than 72 hours or so to pass without him having a read on how I'm doing.”

“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.”

“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.”

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

“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.”

“What I realized is once you get into a business partnership with a friend, the friendship gets totally sublimated to the business partnership.”

“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.”

“I got depressed. So it turns out I have a propensity clinically for depression. And so I got to the place where I kind of had to fake it at work that I was doing okay, drag myself out of bed and come to the office and kind of put on a show.”

“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.”

“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.”

“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”

“The second angel round that we raised. We raised it too high of a price, and actually, Joel was pretty upset about this. I, actually, I think I wrote the email to Joel that Was a condescending email in some regard around supporting the company, and it was the …”

“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.”

“I can't go back in time and do this company on 20 to thirty million. Which is what I think it would take, knowing what I now know”

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

“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 …”

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

“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.”

“Once you get into a business partnership with a friend, the friendship gets totally sublimated to the business partnership. So a lot of the stuff that you used to talk about or do, you don't have time to do because you've got to work on this little growing bab…”

“It turns out I have a propensity clinically for depression, and so I got to the place where I kind of had to fake it at work that I was doing ok, but drag myself out of bed and come to the office and kind of put on a show.”

“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.”

“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”

“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.”

“You create a clothing store that has no clothing. And that was the insight, which is the customer doesn't need it right away, and that flew in the face of everything everyone in retail told me from the traditional industry. Instant gratification. And it turns …”

“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…”

“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.”

“I can't go back in time and do this company on 20 to thirty million. Which is what I think it would take, knowing what I now know”

“Once you've got venture investors who've been in For seven years and angel investors who've been in for 10, it just would be wrong to not make other people money.”