How Introverts Can Succeed in Business, Navigating Class Differences, and Employee Equity

Scott Galloway answers listener questions on whether introverted founders can succeed without being natural salespeople, how to deal with insecurity when you’re surrounded by wealth, and the smartest way to give early employees a real sense of ownership through equity. 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.

• 0:00Speaker 00

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• 0:31Speaker 01

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• 1:01Speaker 02

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• 1:30Scott Galloway?

  Welcome to Office Hours of Prop G. This is the part of the show where we answer a question 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 officehoursofpropgmedia.com. Again, that's officehoursofpropgmedia.com or post your question on the Scott Galloway subreddit and we just might feature it in our next episode. First question.

• 1:55Scott Galloway?

  Our first question comes from initialmiserable7914 on Reddit. They say, "Prof G, I can build products, but I can't work a room. I have a product management background and I've spent the past few years building AI automation tools and micro SaaS. What I don't have is the extroverted hustle gene or the network to attract the operators and capital needed to scale. Is there a path forward for introverted builders who can execute but can't sell themselves? Or does the startup ecosystem just filter us out by design? I keep thinking about how many viable products are dying, not because they're bad, but because the person who built them isn't wired to pitch, network, and evangelize 24 by 7. Is this a solvable inefficiency in the market or just how it has to work?"

• 2:35Scott Galloway?

  So, no, I think in almost every tech company, there's sort of a tech genius or someone on the team who is deeply introverted and awkward. And I'm not saying you're awkward, but it sounds like you're an introvert. And that's why the majority of successful companies are founded by not one, but several people. So, my first company that I started in my second year of business school was a company called Profit, which was a brand strategy firm still around. And my partner was a guy named Ian Chaplin. And Ian was a real... I mean, I think of myself as introverted in the sense that I have the skills to be social, especially if there's alcohol around. I'm even sometimes kind of likable or sort of amusing. "What? I amuse you?"

• 3:18Scott Galloway?

  Anyways, great line from Goodfellas. But I can do that. I can work a room. I can get clients. You know, I can do it. It takes energy from me, and that's the disposition of an introvert. It's not somebody who's not social, but someone who people sort of take energy from them instead of adding energy to them. And an extrovert is somebody who gets energy from people. Anyways, but Ian was a very much an introvert. But he was very strong with technology and operations and had all the skills I don't have. And so typically, the most successful businesses are one where you have an alchemy of talents. No one person brings it all. And so if you bring product management skills, especially in AI, my brother, you bring a lot to a team. You're actually the secret

• 4:01Scott Galloway?

  sauce. Whenever I'm in pitches, whenever I've been in pitches to a VC firm, or am, oftentimes I get asked to sit in on pitches. Basically, the VC will say, all right, who's the tech guy or gal here? Who's the secret sauce? And then they ask them a lot of questions. So it's in some, it sounds like you need a front man or a front woman who understands, is more comfortable pressing the flesh and trying to raise capital. And you need that person to hire. You need that person for clients. And I keep saying this, agency in the greatness of others. Yeah, start a business, but just find a partner. And I have generally found, I've started almost every business I've started with a partner or a core group of people. So again, one plus one equals three here. My brother, you bring a lot to

• 4:44Scott Galloway?

  the table. You just need to find your front man. Thanks for the question. Question number two.

• 4:51Speaker 04

  Hi Scott, this is Matt from Boston. Similar to you, I grew up in a low income, single parent household, and worked hard to make it to a top university on financial aid. Now I'm surrounded by people from very wealthy backgrounds. Some of my close friends, and now my new girlfriend, come from ultra privileged families. I find myself feeling uneasy and hyper aware about this class difference. I can't tell if it's envy, insecurity, or something else, but it's starting to eat away at me. Why do I feel like this? How do I manage this discomfort and stay grounded without letting resentment or self pity creep in? Thanks.

• 5:27Scott Galloway?

  So first off, this is a, it's a question for a licensed therapist, because if this feels like, this feels like there's some sort of, I don't know, insecurity, or trauma, or blockage that you need to work through. But that's not going to stop, stop me from talking about me as a means of giving you advice. But I do think, it sounds like you could benefit from therapy to kind of explore this issue. I share the same sentiment as you. I don't like rich kids. I have a bias against them. And I don't know if it's because I'm jealous, or it's Deferred anger from not having money and that is, I've said this before, I don't, I just don't think, I think people who have money or grew up with money can, they can sympathize

• 6:11Scott Galloway?

  with people that don't have money, but they can't really empathize. I just don't think people, and the story I tell is when I didn't get into UCLA, I'm like, I'm not going to college because I needed to live at home. I couldn't afford to go somewhere else. And as I've said several times, I ended up getting in on appeal. But I remember going over, I lived in a wealthy neighborhood. We had kind of the shittiest condo on the block. My mom's boyfriend, who happened to have another family bought it for us, but that's another story. And, but I was around a lot of kids and what was happening when I went to UCLA, I was broke. I was, there was me and one other kid out of 120 of us that everybody knew had no money. We were always laying on our fraternity bills. But you always feel like there's a ghost whispering in your ear that you're not worthy. I felt like a ghost was following me and my mom around

• 6:55Scott Galloway?

  saying, oh, you fucked up. You guys don't have money. You're not worthy. And it just kind of erodes your self-esteem and you're not as confident. You're not as inclined to take big swings or risks. At least I, I didn't. And I remember being at a friend's house and I was all bummed. I hadn't gotten to UCLA and the, and the, and the dad said, well, just get on a plane and fly out to Michigan or Indiana and show up and don't take no for an answer and speak to the admissions department and, you know, this big rah rah speech, like get up and, okay, I didn't have a fucking credit card. I had maybe been on a plane a half a dozen times in my life. I wasn't going to get on a plane and go to fucking Michigan, to Ann Arbor and just show up. I just, I find that I resent rich kids because I just don't

• 7:38Scott Galloway?

  think there's any goddamn way. And then, by the way, a lot of them are just lovely and very nice. I just don't think there's any way they have any fucking idea about how hard it is to make money and make something of yourself when you don't. When you don't come from money. If a university's mission is to create income mobility, like the most important university in New York is not Columbia or NYU, it's pace, because it takes people who maybe didn't get tutors and all sorts of special time. That's my favorite now in these schools is that every rich parent is convincing or writing a letter saying their kid has some acronym and that they need extra time. You want to hear a scary stat? Poor high schools spend, or high schools in poor areas spend about eight to $10,000

• 8:21Scott Galloway?

  per student. The average high schools, public high schools spends $15,000 per student per year. The average elite private school in America spends $75,000 a year on a kid. So what a shocker, all right? Here's one kid that uses an education infrastructure and gets, say, you know, $180,000 in investment towards him through funnel through this, you know, I think, pretty strong education infrastructure in the US. Some people would say K through 12 is not very strong here and that more, they have data to back it up. But anyways, we spent $180,000 on most kids in America, right?

• 8:59Scott Galloway?

  Whereas rich people invest, vis a vis their education network, approximately $900,000. And what a shocker. They're better prepared for college in the work world and make more. Well, that's, that's a fucking spoiler alert, isn't it? Well, thank you, Captain Obvious. As a matter of fact, middle income homes, kids from middle income homes score an average of 120 points higher on the SAT. That is substantial. But get this, upper income homes score 250 points higher than the middle class kid. So meaning that they score an average 370 points. And you don't think that $900,000 investment over 12 years doesn't make a huge difference?

• 9:43Scott Galloway?

  If we had true kind of affirmative action, trying to get everyone to the starting point at the same time, if you will, then we would spot every poor kid 370 points on the SAT. We would say, if you could figure out a way to get to a 1230, congratulations, you just got a perfect score on the SAT. The strongest indicator of your forward looking success, or the strongest forward looking indicator of your success is no longer grit and your character, your intelligence, your kindness, it's how rich your parents are. This, in my opinion, is the biggest problem. But back to you. Your resentment, I think, is understandable. I have figured out that, OK, enough already. I tried to be more generous and graceful and realized, like, good for them, they were born with money.

• 10:27Scott Galloway?

  Wasn't their fault to the benefit or the drawback. Doesn't mean they're not really good people. But I do find I resent them. I think it's because I'm a little bit jealous and insecure about my upbringing. But if you're really having trouble and it's kind of getting to you and sort of getting in the way or really eroding your confidence, I would suggest there's something deeper going on and suggest that you reach out to a licensed therapist. There's now a bunch of great online platforms. And talk through this issue with a licensed professional to try and... It feels like there might be something deeper here and that it's just manifesting in this specific way. Anyways, very much appreciate the question. And again, I would suggest that you talk this out with a licensed professional. We'll be right back after a quick break.

• 11:19Scott Galloway?

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• 12:04Scott Galloway?

  You can download the Bilt app and join the membership for where you live at joinbilt.com/propg. That's J-O-I-N-B-I-L-T.com/propg. Use our link so they know we sent you.

• 12:19Scott 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?

• 13:04Scott Galloway?

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• 13:25Scott 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?

• 14:10Scott 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 profg for $1,000 off.

• 14:34Scott Galloway?

  Welcome back onto our final question.

• 14:38Speaker 06

  Hey Prof G, my name is Ira, calling in from Power River, British Columbia, Canada. Huge fan of the pod and longtime listener. Please say hi to Ed for me. So I'm the co-founder of a marketing agency that was launched five years ago. We're focused on consulting for landscaping businesses across Canada and the US. I've been thinking a lot lately about your advice on the importance, particularly in the early growth stages of company, of hiring and retaining great people, and then getting out of their way. We recently hit a key milestone for our business of a profitable 1 million in annual recurring revenue. And in order to continue to scale, I know this is going to be critical to get right.

• 15:20Speaker 06

  You often say that if you want people to act like owners, you should make them owners. Do you have any advice on structuring ownership incentives for early employees? Right now, we offer small bonuses tied to revenue thresholds, but I just don't think it really creates that true feeling of ownership. Thanks and keep up all the incredible work.

• 15:41Scott Galloway?

  Thanks for the question and congratulations on your success. A company focused on consulting for landscaping businesses across Canada and the US. That's just so cool. There's so many cool ways to make money. Yeah, look, there's compensation and there's ownership. And compensation is people are going to engage in a certain number of activities in order to increase their compensation. But when you give them ownership, they start, you know, they'll take out the trash from the snack room, or they'll refer, you know, they'll think, oh, this would be a great business opportunity for another division, another part of the company. Whereas compensation usually outline what their metrics are, and they will study to that test. But when you make them owners, they're thinking about every aspect of the business and trying to contribute.

• 16:25Scott Galloway?

  And I find, you know, you give someone some equity, make them an owner, they become like you, and they start thinking about the business even when they're not working. And those are the most important people. I think in a small business, you want to find the critical people and give them chunks of the company. And that's what I've always done. And the mechanics are pretty straightforward. I would do an S-core for a few reasons. One, I don't know if you've looked at 1202, but look at 1202. If you start a company, sell it five years later or more, the equity that you've held for longer than five years, if the company has an enterprise value of less than 50 million, which your company does, the first 10 million are tax-free. Actually, they've just increased it to 15 million. And also, let's be honest, it's

• 17:06Scott Galloway?

  total income inequality, but or total tax loophole for the rich, because VCs get it as well. But anyways, the best means of giving people ownership is usually through options on their equity, because then it's not a taxable event. If you give people equity, outright equity, it becomes a taxable event and they have to write a check. When they exercise their options, they will have to write a small check, because you do basically a valuation of 409A that says, all right, the company is worth $2 million, you're giving them options on 2% of the company, that's $40,000. And they're going to have to write a check for that, but they don't have to actually, not until they exercise their options. Now, there's some other stuff, you want to exercise your options ideally a year or

• 17:50Scott Galloway?

  more before liquidity event, because if you own it for longer than a year, you get long-term capital gains. But, you know, individuals can figure that out with their own tax counsel. But essentially, awarding options is the most tax-efficient way to give people ownership. And I think that you've identified those first two or three key employees, and that doesn't mean they're first. I was cycled through about 10 or 15 people to get to two or three key ones. And that's not pretty, but I think in a small business, it's fucking Vietnam, it's hand-to-hand combat. If someone's not adding a lot of value, you got to shed them and bring in someone else. But when you do find someone that's really outstanding, one, you want to make them an owner, and two, you want to outline your vision for the company around why that ownership will translate to real economic value. So at Prof.

• 18:31Scott Galloway?

  G, I think we're going to continue to add voices, we're growing 20 or 30% a year, and by 2027, my guess is one of these traditional media companies or a new media company is going to panic and decide they want to be in the fastest-growing ad-supported medium, which is podcasting, and will come in and likely acquire us. Now, none of us are going to get to go anywhere, because we'll probably have to sign up for four or five-year employment contracts. But I go through, when we do an all-hands, I outline the vision for this company, I have a track record of getting to exits, and then try to say, okay, if this happens, this will be really good for people. And this is why. So the ownership question is important. It can also be phantom ownership through RSUs, or, you know, there's all sorts of ways to give people different

• 19:14Scott Galloway?

  types of ownership. But traditionally, it's just an S-core, S-core, C-core. I'm trying to get my S's and my C's mixed up. I think it's S-core. And then, is that right? Eh, fuck. Anyway. And then you give them options. So it's not a tax law event when you award it to them. And they believe that it's a, you know, it's, it's real ownership. Also, if you take an investment, I don't think it's a bad idea to try and do a secondary. What's a secondary? Say you want to raise $2 million bucks. And there's, your round is oversubscribed, which is a good problem. Take and say, raise three and take a million and buy people's shares. It's a chance for you to take some money off the table. And also, I do it proportionate. If I sell 10% of my stock to take some money off the table

• 19:59Scott Galloway?

  in a financing round, I'll let everyone else sell 10% of their holdings. Now, there's something very powerful about when those options turn into money to really get people's greed glands going. And some options structured with a lawyer, you can even do most of it on AI right now, that gets people real ownership. And then, just as importantly, outline the vision for the company such that they feel they have a piece of something run by someone who understands how to add value and is also looking for an exit, not looking to give it to their kids and there'll never be an exit. Anyways, congrats on your success. A million dollars in recurring revenue. Just call it AI landscaping or something and go raise billions of dollars to buy chips. Anyways, best of luck to you.

• 20:44Scott Galloway?

  That's all for this episode. If you'd like to submit a question, please email a voice recording to [email protected]. 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. This episode was produced by Jennifer Sanchez. Our assistant producer is Laura Janer. Drew Burrows is our technical director. Thank you for listening to the Prop G Pod from Prop G Media.

• 21:18Speaker 07

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• 22:19Speaker 09

  This podcast is supported by Anthropic, the public benefit corporation behind Claude. Everyone's got a hard question about AI. Anthropic was built to surface those questions and share what it finds along the way, because there's hope in hard questions. Ask yours at claude.ai/spotify and keep thinking. That's claude.ai/spotify.