Scott’s Greatest Legacy and Why Your 20s Are Overrated

Scott Galloway reflects on his legacy, shares what to expect from life after college, and offers advice on raising money and building relationships. Want to be featured in a future episode? Send a voice recording to [email protected], or drop your question in the r/ScottGalloway subreddit. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Scott Galloway?

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• 0:48Speaker 01

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• 1:19Speaker 02

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• 1:54Scott Galloway?

  Welcome to Office Hours with Prop G. This is the part of the show where we answer your questions about business, big tech, entrepreneurship, and whatever else is on your mind. If you'd like to submit a question for next time, you can send a voice recording to officehourswithpropgmedia.com. Again, that's officehourswithpropgmedia.com or post your question on the Scott Galloway subreddit and we just might feature it in our next episode. Question number one. Our first question comes from Scuba Hood Doug Fisher on Threads. Interesting name. They say, "Hey, Prop G, is Resist and Unsubscribe the most influential thing you've done? If not, what do you feel is or what do you hope will be your biggest impact on the planet?" That's a generous question. Uh, no, it isn't. I wouldn't say

• 2:36Scott Galloway?

  it's not even in the top three. The impact of Resist and Unsubscribe, since January 30th, over 21 million views across social media, about, we'll probably cross about 2 million site visits, unique visitors to the site today. To Resist and Unsubscribe, so you know, the state of Maine, I don't know how many people Maine has, but a state with 2 million people have showed up to Resist and Unsubscribe. The thing I'm most proud of on the visits is that we haven't spent a single cent to drive that traffic. Uh, I've been all over AI trying to figure out what I would need to spend if I, from a standing start, I was trying to get 2 million people to show up to an ecommerce site. And it's somewhere between 2 and 7 million, depending on the efficiency. Anyways, we've had thousands

• 3:18Scott Galloway?

  of new subscribers, so no mercy, no malice, thousands of screenshots shared by you, our listeners via Instagram, email, and our subreddit. Since March 1, we're seeing about, I don't know, somewhere between 10 and 15,000 site visits per day. I need to get that back up. It was at 60 to 80. I like the idea of a stadium showing up to the site every day. So what I'm trying to do is we did a live event last night in Minneapolis with Governor Walz. It was called Resist and Unsubscribe. Sold out 1,000 people to Pantages Theatre in 48 hours. That city is so unified right now. If you want to have a great vacation or you want to do an event, I would suggest going to Minneapolis right now. That city's just on fire. People are feeling so, there's such a sense of community there right now. We raised $138,000 in the Immigrant Law Center of Minneapolis through ticket sales.

• 4:04Scott Galloway?

  And matching. But yeah, anyways, it was wonderful. And trying to communicate to people that I like the idea. The most creative thing about the idea is that it's the easiest way to have a big impact with a minimal amount of consumer disruption. And that is if right now you go to resist and unsubscribe.com and unsubscribe from OpenAI and you post it to your social media screenshot of your unsubscription confirmation from OpenAI. Then effectively, if you get three or four other people, inspire three or four other people to unsubscribe, that's about $240 each, times four, 960, let's call a thousand bucks. It's trading at 40 times revenue. You can take $40,000 out of the market cap of OpenAI and say, guys, when you give,

• 4:46Scott Galloway?

  when you're the largest donor to the Trump campaign, when you're enabling ICE, there is a downside. There is a downside. And we have a calculator where you can calculate your impact based on who you're unsubscribing from and the, the impact or the footprint of your social media following. And we're trying to figure out just a way to make it easy or seamless for people to do this and create two objectives. Send a signal to consumers that their economic spending is a, is a more powerful weapon than, than they imagined. And to create the other side of the incentive coin, if you will, for CEOs. Anyways, enough of that. The biggest impact I've had on a cultural level, hands down, it's five years ago, six

• 5:28Scott Galloway?

  years ago, I read a story about a young man, a sophomore at Oklahoma State named Alex Kearns, who got errant emails from Robin Hood, or as I like to refer, mendacious Fox, saying that he owed $60,000 because he was trading options without his family's knowledge. Very distraught, emailed dozens of times to the night, couldn't get a response back and decided to take his own life. And I saw a picture of the kid. And when you're a dad, occasionally you see a picture of a kid, a fallen service serviceman or a kid who takes his own life. And you can't help it, but you see your own son. And it really, it just quite frankly, it just rattled the shit out of me. So I reached out to the Kearns family to express my sympathies and actually had a

• 6:12Scott Galloway?

  conversation with Alex's uncle.

• 6:17Scott Galloway?

  And started doing a deep dive around young men and it just led to a lot of recognition or just data I just did absolutely stunned me. Going to a morgue and there's five people who died by suicide, four men, one in three men under the age of 25 is living at home. Only one in three, um, only one in three men under the age of 30 is in a relationship. Forty-two percent of men, 18 to 24 have never asked a woman out in person. One in five men under the age of 30 is still living at home. One in seven men are called NEETS and that is they aren't even trying. They're not in education. They're not, they're not um, in employment. They're not in training. They're literally doing uh, nothing. Levels of obesity, depression, anxiety. Men aged 20 to 30 are spending less time outdoors

• 7:02Scott Galloway?

  than prison inmates. They're just becoming, we're just producing, I think through a combination of economics, social movements, um, we're kind of destroying the cultural and economic standing of middle-class men. And also they're up against this indomitable folk called big tech, which every day is trying to figure out millions of ways to get them to spend one less second with the most important thing in life, their relationships and more time on a screen. And so I started talking about struggling young men and I like waiting in dangerous waters. I like going into topics that I know I get pushed back on. Um, because if you're not, if you're not getting critical feedback, you're not saying anything and I like, I like going, again, waiting in dangerous waters. I think it's important and I'm blessed

• 7:46Scott Galloway?

  with economic security and people love me unconditionally. So you, you have the luxury of speaking your mind. So I think culturally or the things I'm, I'm most proud of is raising awareness around the struggles of young men and establishing a lot of kind of what I'll call parasocial relationships with single mothers who are looking for, I don't know, not even guidance, but empathy or to feel seen about the struggles that their sons are facing. And then on a professional level, the thing I'm most proud of is that I'd like to think I've created a lot of economic security for wonderful young people and their family. Uh, I have started and sold several companies and I typically don't own more than 30 or 40% of the company when I sell it. And uh, I think it's, it's not.

• 8:32Scott Galloway?

  It's not having money that's great, which it is. That's great, but what's really wonderful is making it. And what's amazing is making it with other people. And so I'm really proud. I've gone through, I start small companies. I've never, I don't have the skills to build a big company, but I've built small companies and took them to exit. And I think somewhere between 27 and 37 people become millionaires on a, on a single day because of when we sold those companies. I'm really proud of that. That's the thing I'm most proud of is creating economic security. For myself, I put myself, I'm number one. I fixed my own oxygen mask before anyone else. I don't want to sound too virtuous, but it's worked out for a lot of people and I'm proud of that. And then I think at the end of my life, the thing I'm going to be most proud of is I think I'm raising loving patriotic men.

• 9:17Scott Galloway?

  But yeah, God, a lot of boasting right now. Yeah, anyways, generous question. Thanks very much. Question number two comes from Instagram. Kaitlyn Castro asks, how do I get over the fear of life after college? I don't know. Get over it. How do you get over it? I don't know. Stay focused one day at a time. Get a job, find roommates, get excited about making money. It is an insecure kind of weird time. I got a job in investment banking right out of college. It was awful. The people were awful. The work was awful. I hated the people, they hated me. And I thought, oh, this is life after college. Doesn't this suck? Keep in mind, I just want to prepare you. Your first job's going to suck because you're the low person on the totem pole. So you're doing all the shit work.

• 10:03Scott Galloway?

  It's not drinking beer and going to, you know, brewing games. In Pasadena, the Rose Bowl, which was awesome, which was awesome. So it's a bit of like a splash of cold water, but it's nice to start making some money. It's nice to have your own place, both of which I was doing. So it was a nice time. Was it a nice time? It wasn't, I was miserable. Also, I couldn't get arrested. I was dating like crazy in college. And then. When you're 22 and I moved to New York to join Morgan Stanley, you can't get fucking arrested as a young man. You can't get into clubs, no one, no doorman says, hey, you 22 year old dude, come on in.

• 10:39Scott Galloway?

  Different story for 22 year old women, different story. And also for a 32 year old guy who is the type of douchebag who'll spend $1,100 on a bottle of vodka or something. So I just, and all the women, this is going to light people's hair on fire, didn't want to date 22 year old dudes. They wanted to date 32 year old dudes that could take them to the same bar to the Hampton. So you literally, no game, no dating, working 12 fucking hours a day for assholes. And I miss my mom, I miss being alone, or I didn't like being alone in New York. It was just, it wasn't a great time. What I can tell you is it's where you start workshopping, you make some interesting friends, you start figuring out what you want to do with your life. It's really nice to start making some money. It's nice to start zeroing in on what you want to do with your life.

• 11:23Scott Galloway?

  So I think it's a nice, it's an interesting time of your life. And also coming out of college right now, distinct to what everyone says about all the catastrophizing about AI, so they're going to raise more fucking money pretending they're more important than they are. You know, it's, there's, 22 year olds right now, actually, I think have a lot of agency. They have a lot of opportunities to do things, different things professionally. There just didn't seem like there were a lot of options when I was going to, either when, at UCLA, either went to work for Arthur Andersen, or got a job in finance or in brand management. That was a big one. Clorox, people go manage, you know, the Swiffer, you know, or also the CIA recruited at UCLA. I thought that was really interesting. I tried to interview, but I didn't speak another language, so they weren't interested in speaking to me.

• 12:06Scott Galloway?

  Anyway, I think now entrepreneurship is a huge option. 150,000 people applied for small business applications in 2000. Now it's about half a million. Young people are much more bold, take much more risks. And also they have access to capital. You can raise money in 1997, 87, when I graduated from college. And now if you have an idea and you're a junior about to drop out from Harvard or Carnegie Mellon, there's probably like six different meetups and angel, angels of Pittsburgh where they potentially will invest, you could raise a half a million or a million bucks. So one of the things I, I'm not that sympathetic to is young people bitching about how hard it is. You actually have a decent amount of agency right now. I think it's a probably a pretty interesting time.

• 12:49Scott Galloway?

  And yeah, AI is kind of, I don't know, stilted or put hiring, you're hiring into stasis, but they're still hiring people. So, um, look at the bright side. Look at the bright side. And also before you start work, when you graduate, just to ease into the work world, get a backpack and go to Europe for eight weeks, which is what I did with my buddies, Lee Lotus and David Kingsdale. And that was just, uh, just such an incredible, that's something I'll remember the rest of my life. I budgeted myself $55 a day and lived like a king. Didn't even stay in hostel, stayed at two-star hotels where they would turn the air conditioning off between 1:00 AM and 4:00 AM and just had the best time. Oh my God, that was such a wonderful trip. And, uh, anyway, so a lot to look forward to. It's time to be an adult.

• 13:34Scott Galloway?

  If you're scared about going into the work world or leaving college, it means you might have a decent amount of anxiety and you may want to see someone about it. Or, or you just had such an amazing time in college, uh, you're worried about leaving, worried it won't be as good. And, uh, spoiler alert, it's not as good, but it's not as probably bad as you might think. And if it is bad, that's a learning because you realize this isn't the life I want and you pivot, as I did, to something else and find, find another way to make a living and something where you can think you can be. Let me put it this way, I have an incredible life. I would think hard about switching places with you. If I could take my kids with me and my friends, nah, I could probably leave a few of my friends behind.

• 14:15Scott Galloway?

  But if I could take the majority of my relationships back with me and give up all my money, I probably, I'd think about it. So a lot of people want to be you. Thanks for the question. We'll be right back after a quick break. Support for the show comes from Nutraful, the number one dermatologist recommended hair growth supplement brand used by over one and a half million people. With age comes knowledge, patience, and for some, hair loss. Didn't say it was all good things. And for those who want to do something about it, there's Nutraful. Nutraful has formulas built for men at different life stages. They have Nutraful Men for Guys Age 18 to 49, plus the new Nutraful Men 50 and Older.

• 15:01Scott Galloway?

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• 15:39Scott Galloway?

  Support for the show comes from Vanta. As AI adoption grows, so does your company's security risks and requirements. New frameworks, audits, and vendors keep piling on, but your team isn't getting any bigger. Most compliance tools promise automation, but you're really stuck doing all the work by hand, chasing screenshots, validating controls, and playing catch-up when audit season comes around again. Vanta works differently. Their Agentic Trust platform is built to scale with you, not slow you down. With over 1,400 automated tests across 400-plus integrations, Vanta collects evidence and monitors your controls year-round, cutting your audit prep by 82%. Plus, you can access the Vanta agent everywhere you work, whether your team is in Vanta every day or living in tools including Claude or Cursor. Want proof?

• 16:24Scott Galloway?

  Over 16,000 fast-growing companies like Ramp, Rider, and Harvey save time and resources while scaling fast with Vanta. Learn more at vanta.com/provg and get $1,000 off. That's spelled V-A-N-T-A dot com slash PROP G for $1,000 off.

• 16:46Scott Galloway?

  Support for the show comes from Vanta. As AI adoption grows, so does your company's security risks and requirements. New frameworks, audits, and vendors keep piling on, but your team isn't getting any bigger. Most compliance tools promise automation, but you're really stuck doing all the work by hand, chasing screenshots, validating controls, and playing catch-up when audit season comes around again. Vanta works differently. The regentic trust platform is built to scale with you, not slow you down. With over 1,400 automated tests across 400-plus integrations, Vanta collects evidence and monitors your controls year-round, cutting your audit prep by 82%. Plus, you can access the Vanta agent everywhere you work, whether your team is in Vanta every day or living in tools including Claude or Cursor. Want proof?

• 17:31Scott Galloway?

  Over 16,000 fast-growing companies like Ramp, Ryder, and Harvey save time and resources while scaling fast with Vanta. Learn more at vanta.com/profg and get $1,000 off. That's spelled V-A-N-T-A dot com slash prof G for $1,000 off.

• 17:55Scott Galloway?

  Welcome back. Question number three.

• 17:57Speaker 03

  Hello, Professor Galloway. This is Stephanie from Sacramento. My question is regarding asking rich people for money. I'm on the board of a local community theater nonprofit, and the board has been tasked this year with helping to boost our fundraising. We've tried lots of types of fundraising events and have tried bringing on local businesses as sponsors, but it usually ends up being a lot of work for not very much payout. And many of our local small businesses are just trying to stay alive right now and can't dedicate funds towards sponsoring. We found one possibly effective solution is to bring on donors, patrons, who are willing to write one or two checks per year. We've had two people related to members of our organization donate fairly sizable amounts once, but I'm at a loss as to how to approach other affluent potential patrons.

• 18:41Speaker 03

  Most of the foundations that I've researched have really specific criteria for what organizations they donate to and really lengthy and complicated applications. And the same goes for most of the grants that we apply for. So how do we find high-net-worth individuals who might be interested in supporting local community theater? But more importantly, how do we approach them to make the ask? This whole asking for money thing is pretty uncomfortable for me, but I'm willing to do what I need to to support this amazing organization. And honestly, I just want to use my time as efficiently as possible. Thank you.

• 19:15Scott Galloway?

  Thanks for the question. I'm not sure I'm an expert here. I've been... I've asked for a lot of money, but I asked for money for my businesses. I've probably done...

• 19:26Scott Galloway?

  Six or 800 meetings where I've asked people for money, but it's usually asking them to sponsor my latest crazy startup. And it's hard. And the reason why the most overcompensated people relative to their talent and their IQ are the salespeople. Why? Because 98% of people aren't willing to ask people for money. That's what sales is. You're calling them saying, hey, will you give me $100 a month? And I'll give you a site license or a seat for this software that will, that will figure out what snacks you need and order them for you. And asking for money, the highest paid people or the second highest paid person typically at a university, the highest paid is the chancellor and the second highest paid are usually at some professor in the medical school. But the second highest paid person is usually the director of development,

• 20:10Scott Galloway?

  the money woman or the money man. I get asked for money a lot. Public school or public education is kind of my philanthropy, if you will. Let me virtue signal. I think I've given money to about a dozen public universities. Public university changed my life. So it's sort of just a payback. But typically, the ask is, I'm in town, you know, hi, I'm the head of development for the University of Wisconsin-Madison, and I'm in town. And the place you start, quite frankly, is previous donors. And they say, we want to update you. So you'd start with the previous name. We want to update you on your program where you gave money. And you generally find out, I'll give you an example, UW-Madison, there's a penitentiary program where professors teach at a local penitentiary and give the

• 20:54Scott Galloway?

  inmates who are scheduled for release in the next several years, opportunity to earn credit such that they can hopefully have some motivation to get their AA or their bachelors once they're, once they're after release. And I just love this program. And the guy is really smart. The runts it there. He'll reach out to me and say, I'm in New York, or he'll come to an event. And I like him. And they'll tell me about the program and I get inspired and I write a chat. So the first place you want to go is your existing donors and talk to them about your plans for community theater. You might want to start cultivating.

• 21:26Scott Galloway?

  It's a relationship. It's very hard to just call people and ask people for money. Uh, you may want to have some sort of upper tier where people get access to uh, tickets or meet and greet with the actors and the producers and start calling or identifying a pool of people who are passionate about community theater.

• 21:44Scott Galloway?

  Finding out who are the donors, the biggest donors, and there's these lists now everywhere in your area and then asking to have coffee with them and talk to them about community theater.

• 21:55Scott Galloway?

  Uh, the wealthy parents of interns, but you're basically, your job is to be very social, go out a lot, meet people, ask for a coffee to talk to them about community theater, get them excited about it. I'm not sure, you know, talk to someone who's successful. And then do you do the ask on the first? I don't. I think you invite them. You have an interesting product to sell that people can get kind of emotionally engaged in. And then figure out badging, like the, uh, you know, if you're in Milwaukee, the Milwaukee Arts Circle where for a certain amount of money, they get invited to a dinner every year or they get listed, uh, recognition, you know, we are, we are going to be naming

• 22:36Scott Galloway?

  components of the theater, whether it's the, you know, the, the, a stage or, you know, one of the, one of the, you know, one of the rooms of the hall or the conference room, where there's some naming opportunities we'd like to talk to you about. People love recognition by the local community, but this is a fairly mature industry. And there are classes you can take at Wharton and Columbia and Berkeley online on nonprofit fundraising. So, uh, don't listen to my word, Sal. There's a lot of, a lot of, uh, this is a big industry, raising money for nonprofits. Um, probably the best fundraiser I've ever met is a guy named Scott Harrison at Cherry

• 23:18Scott Galloway?

  Water. I don't have a lot of interest in potable water in Sub-Saharan Africa.

• 23:24Scott Galloway?

  Is that wrong? But I'm inspired by Scott. He does a great job of keeping in touch with me, sending me interesting articles. And then, I mean, he's, he wants to take me and my boys to Africa to show them building a well. That'll be the most expensive trip I've ever taken because I'm sure I'll be very moved by it and end up writing a sizable check. But it's just a lot of hand-to-hand combat, maintaining relationships, coming to people with opportunities, creating badging, recognition. I mean, there's just, there's a whole art and science to this. So anyways, ignore the above and sign up for a course and get some great information online on how to raise money for nonprofits in the arts. Thanks for the question and your good work.

• 24:10Scott Galloway?

  That's all for this episode. If you'd like to submit a question, please email a voice recording to [email protected]. Again, that's [email protected]. Or if you prefer to ask on Reddit, just post your question on the Scott Galloway subreddit and we just might feature it in an upcoming episode.

• 24:28Scott Galloway?

  This episode was produced by Jennifer Sanchez and Laura Janer. Kami Rika is our social producer, Brad Williams is our editor, and Drew Burrows is our technical director. Thank you for listening to the Prop G Pod from Prop G Media.

• 24:46Speaker 04

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