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

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0:01:56 Welcome to Office Hours of Prop G.
0:02:01 This is the part of the show where we answer a question about business, big tech, entrepreneurship, and whatever else is on your mind.
0:02:06 If you’d like to submit a question for next time, you can send a voice recording to officehoursofproptamedia.com.
0:02:08 Again, that’s officehoursofproptamedia.com.
0:02:13 Or post your question on the Scott Galloway subreddit, and we just might feature it in our next episode.
0:02:14 First question.
0:02:24 Our first question comes from InitialMiserable7914 on Reddit.
0:02:25 They say,
0:02:28 Prop G, I can build products, but I can’t work a room.
0:02:33 I have a product management background, and I’ve spent the past few years building AI automation tools and micro-sass.
0:02:38 What I don’t have is the extroverted hustle gene or the network to attract the operators and capital needed to scale.
0:02:45 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?
0:02:54 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.
0:02:59 Is this a solvable inefficiency in the market, or just how it has to work?
0:03:00 So, no.
0:03:07 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.
0:03:09 And I’m not saying you’re awkward, but it sounds like you’re an introvert.
0:03:15 And that’s why the majority of successful companies are founded by not one, but several people.
0:03:24 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.
0:03:28 And my partner was a guy named Ian Chaplin.
0:03:37 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.
0:03:39 I’m even sometimes kind of likable or sort of amusing.
0:03:40 What?
0:03:42 I amuse you?
0:03:45 And it was a great line from Goodfellas.
0:03:47 But I can do that.
0:03:48 I can work a room.
0:03:49 I can get clients.
0:03:51 You know, I can do it.
0:03:52 It takes energy from me.
0:03:54 And that’s the disposition of an introvert.
0:04:01 It’s not somebody who’s not social, but someone who people sort of take energy from them instead of adding energy to them.
0:04:03 And an extrovert is someone who gets energy from people.
0:04:07 Anyways, but Ian was a very much an introvert.
0:04:11 But he was very strong with technology and operations and had all the skills I don’t have.
0:04:17 And so, typically, the most successful businesses are one where you have an alchemy of talents.
0:04:18 No one person brings it all.
0:04:25 And so, if you bring product management skills, especially in AI, my brother, you bring a lot to a team.
0:04:26 You’re actually the secret sauce.
0:04:34 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.
0:04:39 Basically, the VC will say, all right, who’s the tech guy or gal here?
0:04:40 Who’s the secret sauce?
0:04:41 And then they ask them a lot of questions.
0:04:51 So, 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.
0:04:52 And you need that person to hire.
0:04:54 You need that person for clients.
0:04:55 And I keep saying this.
0:04:56 Agency and the greatness of others.
0:04:59 Yeah, start a business, but just find a partner.
0:05:02 And I have generally found, I’ve started almost every business.
0:05:05 I’ve started with a partner or a core group of people.
0:05:08 So, again, one plus one equals three here, my brother.
0:05:09 You bring a lot to the table.
0:05:11 You just need to find your front man.
0:05:12 Thanks for the question.
0:05:15 Question number two.
0:05:16 Hi, Scott.
0:05:17 This is Matt from Boston.
0:05:25 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.
0:05:28 Now, I’m surrounded by people from very wealthy backgrounds.
0:05:34 Some of my close friends, and now my new girlfriend, come from ultra-privileged families.
0:05:38 I find myself feeling uneasy and hyper-aware about this class difference.
0:05:43 I can’t tell if it’s envy, insecurity, or something else, but it’s starting to eat away at me.
0:05:45 Why do I feel like this?
0:05:50 How do I manage this discomfort and stay grounded without letting resentment or self-pity creep in?
0:05:51 Thanks.
0:06:04 So, first off, this is a question for a licensed therapist because this feels like there’s some sort of, I don’t know, insecurity or trauma or blockage that you need to work through.
0:06:08 But that’s not going to stop me from talking about me as a means of giving you advice.
0:06:14 But I do think it sounds like you could benefit from therapy to kind of explore this issue.
0:06:17 I share the same sentiment as you.
0:06:19 I don’t like rich kids.
0:06:20 I have a bias against them.
0:06:26 And I don’t know if it’s because I’m jealous or it’s deferred anger from not having money.
0:06:38 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 with people that don’t have money, but they can’t really empathize.
0:06:44 So, 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.
0:06:46 I couldn’t afford to go somewhere else.
0:06:50 And as I’ve said several times, I ended up getting in on appeal.
0:06:53 But I remember going over, I lived in a wealthy neighborhood.
0:06:55 We had kind of the shittiest condo on the block.
0:06:59 My mom’s boyfriend, who happened to have another family, bought it for us, but it’s another story.
0:07:04 But I was around a lot of kids and I was having them when I went to UCLA.
0:07:05 I was broke.
0:07:09 There was me and one other kid out of 120 of us that everybody knew had no money.
0:07:10 We were always laying on our fraternity bills.
0:07:17 But you always feel like there’s a ghost whispering in your ear that you’re not worthy.
0:07:21 I felt like a ghost was following me and my mom around saying, oh, you fucked up.
0:07:22 You guys don’t have money.
0:07:22 You’re not worthy.
0:07:27 And it just kind of erodes your self-esteem and you’re not as confident.
0:07:29 You’re not as inclined to take big swings or risks.
0:07:32 At least I didn’t.
0:07:36 And I remember being at a friend’s house and I was all bummed.
0:07:37 I hadn’t gone to UCLA.
0:07:43 And the dad said, well, just get on a plane and fly out to Michigan or Indiana and show up
0:07:47 and don’t take no for an answer and speak to the admissions department and, you know,
0:07:49 speak a rah-rah speech like get up.
0:07:52 And OK, I didn’t have a fucking credit card.
0:07:55 I had maybe been on a plane a half a dozen times in my life.
0:07:59 I wasn’t going to get on a plane and go to fucking Michigan, to Ann Arbor and just show up.
0:08:04 I just I find that I resent rich kids because I just don’t think there’s any goddamn way.
0:08:07 And by the way, a lot of them are just lovely and very nice.
0:08:14 I just don’t think there’s any way they have any fucking idea about how hard it is to make
0:08:19 money and make something of yourself when you don’t when you don’t come from money.
0:08:23 The university’s mission is to create income mobility, like the most important university
0:08:24 in New York is not Columbia or NYU.
0:08:30 It’s PACE because it takes people who maybe didn’t get tutors and all sorts of special time.
0:08:35 That’s my favorite now in these schools is that every rich parent is convincing or writing
0:08:39 a letter saying their kid has some acronym and that they need extra time.
0:08:41 You want to hear a scary stat.
0:08:46 Poor high school spend or high schools in poor areas spend about eight to ten thousand dollars
0:08:47 per student.
0:08:51 The average high schools, public high school spends fifteen thousand dollars per student
0:08:52 per year.
0:09:00 The average elite private school in America spends seventy five thousand dollars a year on a kid.
0:09:02 So what a shocker.
0:09:02 All right.
0:09:07 Here’s one kid that uses an education infrastructure and gets, say, you know, one hundred and eighty
0:09:12 thousand dollars in investment towards him through funneled through this, you know, I think
0:09:14 pretty strong education infrastructure in the U.S.
0:09:18 Some people would say K through 12 is not very strong here and they have more data to back
0:09:18 it up.
0:09:22 But anyways, we spent one hundred eighty thousand dollars on most kids in America.
0:09:23 Right.
0:09:31 Whereas rich people invest vis-a-vis their education network approximately nine hundred thousand
0:09:31 dollars.
0:09:33 And what a shocker.
0:09:36 They’re better prepared for college in the work world and make more.
0:09:39 Well, that’s that’s a fucking spoiler alert, isn’t it?
0:09:41 Well, thank you, Captain Obvious.
0:09:47 As a matter of fact, middle income homes, kids from middle income homes score an average of
0:09:49 one hundred and twenty points higher on the SAT.
0:09:51 That is substantial.
0:09:57 But get this, upper income homes score two hundred and fifty points higher than the middle
0:09:57 class kid.
0:10:02 So meaning that they score on average three hundred and seventy points.
0:10:05 And you don’t think that nine hundred thousand dollars in investment over 12 years doesn’t
0:10:07 make a huge difference.
0:10:11 Once if we had true kind of affirmative action trying to get everyone to the starting point
0:10:18 at the same time, if you will, then we would spot every poor kid three hundred and seventy
0:10:19 points on the SAT.
0:10:21 We would say if you could figure out a way to get to a 1230.
0:10:23 Congratulations.
0:10:25 You just got a perfect score on the SAT.
0:10:30 The strongest indicator of your forward looking success or the strongest forward looking indicator
0:10:34 of your success is no longer grit, your character, your intelligence, your kindness.
0:10:36 It’s how rich your parents are.
0:10:39 This, in my opinion, is the biggest problem.
0:10:40 But back to you.
0:10:43 Your your resentment, I think, is understandable.
0:10:47 I have figured out that, OK, enough already are.
0:10:50 I try to be more generous and graceful and realize, like, good for them.
0:10:51 They were born with money.
0:10:54 Wasn’t their fault to the benefit or the drawback.
0:10:56 Doesn’t mean they’re not really good people.
0:10:58 But I do find I resent them.
0:11:02 I think it’s because I’m a little bit jealous and insecure about my upbringing.
0:11:07 But if you’re really having trouble and it’s kind of getting to you and sort of getting
0:11:12 in the way or really eroding your confidence, I would suggest there’s something deeper going
0:11:15 on and suggest that you reach out to a licensed therapist.
0:11:20 There’s now a bunch of great online platforms and talk through this issue with a licensed professional
0:11:25 to try and it feels like there might be something deeper here and that it’s just manifesting
0:11:26 in this specific way.
0:11:29 Anyways, very much appreciate the question.
0:11:33 And again, I would suggest that you talk this out with a licensed professional.
0:11:36 We’ll be right back after a quick break.
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0:15:07 Welcome back onto our final question.
0:15:14 Hey, Prof G. My name is Ira, calling in from Power River, British Columbia, Canada.
0:15:17 A huge fan of the pod and longtime listener.
0:15:19 Please say hi to Ed for me.
0:15:24 So I’m the co-founder of a marketing agency that was launched five years ago.
0:15:28 We’re focused on consulting for landscaping businesses across Canada and the U.S.
0:15:34 I’ve been thinking a lot lately about your advice on the importance, particularly in the early
0:15:39 growth stages of company, of hiring and retaining great people and then getting out of their way.
0:15:45 We recently had a key milestone for our business of a profitable one million in annual recurring
0:15:46 revenue.
0:15:51 And in order to continue to scale, I know this is going to be critical to get right.
0:15:55 You often say that if you want people to act like owners, you should make them owners.
0:16:00 Do you have any advice on structuring ownership incentives for early employees?
0:16:05 Right now, we offer small bonuses tied to revenue thresholds.
0:16:08 But I just don’t think it really creates that true feeling of ownership.
0:16:11 Thanks and keep up all the incredible work.
0:16:15 Thanks for the question and congratulations on your success.
0:16:20 A company focused on consulting for landscaping businesses across Canada and the U.S.
0:16:21 That’s just so cool.
0:16:22 There’s so many cool ways to make money.
0:16:26 Yeah, look, there’s compensation and there’s ownership.
0:16:32 And compensation is people are going to engage in a certain number of activities in order to
0:16:33 increase their compensation.
0:16:38 But when you give them ownership, they start, you know, they’ll take out the trash from the
0:16:44 snack room or they’ll refer, you know, they’ll think, oh, this would be a great business
0:16:47 opportunity for another division, another part of the company.
0:16:52 Whereas compensation usually outline what their metrics are and they will study to that test.
0:16:56 But when you make them owners, they’re thinking about every aspect of the business and trying
0:16:56 to contribute.
0:17:00 And I find, you know, give someone some equity, make them an owner.
0:17:03 They become like you and they start thinking about the business even when they’re not working.
0:17:06 And those are the most important people.
0:17:11 I think in a small business, you want to find the critical people and give them chunks of
0:17:11 the company.
0:17:14 And that’s what I’ve always done.
0:17:16 And the mechanics are pretty straightforward.
0:17:18 I would do an S-Core for a few reasons.
0:17:21 One, I don’t know if you’ve looked at 1202, but look at 1202.
0:17:28 If you start a company, sell it five years later or more, the equity that you’ve held
0:17:31 for longer than five years, if the company has an enterprise value of less than 50 million,
0:17:34 which your company does, the first 10 million are tax-free.
0:17:36 Actually, they’ve just increased it to 15 million.
0:17:41 And also, let’s be honest, it’s total income inequality or total tax loophole for the rich
0:17:43 because VCs get it as well.
0:17:48 But anyways, the best means of giving people ownership is usually through options on their
0:17:50 equity because then it’s not a taxable event.
0:17:54 If you give people equity, outright equity, it becomes a taxable event and they have to
0:17:54 write a check.
0:18:01 When they exercise their options, they will have to write a small check because you do basically
0:18:07 evaluation of 409A that says, all right, the company is worth $2 million.
0:18:09 You’re giving them options on 2% of the company.
0:18:11 That’s $40,000.
0:18:16 And they’re going to have to write a check for that, but they don’t have to actually, not
0:18:18 until they exercise their options.
0:18:19 Now, there’s some other stuff.
0:18:22 You want to exercise your options ideally a year or more before a liquidity event because
0:18:25 if you own it for longer than a year, you get long-term capital gains.
0:18:28 But individuals can figure that out with their own tax counsel.
0:18:35 But essentially, awarding options is the most tax-efficient way to give people ownership.
0:18:40 And I think that you’ve identified those first two or three key employees, and that doesn’t
0:18:40 mean they’re first.
0:18:44 I was cycled through about 10 or 15 people to get to two or three key ones.
0:18:45 And that’s not pretty.
0:18:48 But I think in a small business, it’s fucking Vietnam.
0:18:49 It’s hand-to-hand combat.
0:18:52 If someone’s not adding a lot of value, you got to shut them and bring in someone else.
0:18:56 But when you do find someone that’s really outstanding, one, you want to make them an
0:18:56 owner.
0:19:00 And two, you want to outline your vision for the company around why that ownership will
0:19:02 translate to real economic value.
0:19:06 So with Prof G, I think we’re going to continue to add voices.
0:19:07 We’re growing 20 or 30% a year.
0:19:12 And by 2027, my guess is one of these traditional media companies or a new media company is going
0:19:15 to panic and decide they want to be in the fastest-growing out-supported medium, which is
0:19:19 podcasting, and will come in and likely acquire us.
0:19:22 Now, none of us are going to get to go anywhere because we’ll probably have to sign up for four
0:19:23 or five-year employment contracts.
0:19:29 But I go through, when we do an all-hands, I outline the vision for this company.
0:19:31 I have a track record of getting to exits.
0:19:36 And then try to say, okay, if this happens, this will be really good for people.
0:19:37 And this is why.
0:19:40 So the ownership question is important.
0:19:45 It can also be phantom ownership through RSUs or, you know, there’s all sorts of ways to
0:19:46 give people different types of ownership.
0:19:48 But traditionally, it’s just an S-core.
0:19:50 It’s S-core or C-core?
0:19:53 I’m getting my S’s and my C’s mixed up.
0:19:54 I think it’s S-core.
0:19:55 And then, is that right?
0:19:56 Eh, fuck.
0:20:01 Anyway, and then you give them options so it’s not a taxable event when you award it to them.
0:20:06 And they believe that it’s a, you know, it’s real ownership.
0:20:11 Also, if you take an investment, I don’t think it’s a bad idea to try and do a secondary.
0:20:12 What’s a secondary?
0:20:17 Say you want to raise two million bucks and your round is oversubscribed, which is a good
0:20:17 problem.
0:20:21 Take and say, raise three and take a million and buy people’s shares.
0:20:24 It’s a chance for you to take some money off the table.
0:20:27 And also, I do it proportionate.
0:20:32 If I sell 10% of my stock to take some money off the table in a financing round, I’ll let
0:20:35 everyone else sell 10% of their holdings.
0:20:39 Now, there’s something very powerful about when those options turn into money to really
0:20:41 give, get people’s greed glands going.
0:20:45 And some options structured with a lawyer.
0:20:50 You can even do most of it on AI right now that gets people real ownership.
0:20:54 And then just as importantly, outline the vision for the company such that they feel they have
0:20:59 a piece of something run by someone who understands how to add value and is also looking for an
0:21:01 exit, not looking to give it to their kids and they’ll never be an exit.
0:21:04 Anyways, congrats on your success.
0:21:08 A million dollars in recurring revenue, just call it AI landscaping or something and go
0:21:11 raise billions of dollars to buy chips.
0:21:14 Anyways, best of luck to you.
0:21:17 That’s all for this episode.
0:21:20 If you’d like to submit a question, please email a voice recording to officehours at
0:21:21 prof2media.com.
0:21:23 That’s officehours at prof2media.com.
0:21:27 Or if you prefer to ask on Reddit, just post your question on the Scott Galloway subreddit
0:21:30 and we just might feature it in an upcoming episode.
0:21:36 This episode was produced by Jennifer Sanchez.
0:21:38 Our assistant producer is Laura Janair.
0:21:39 Drew Burrows is our technical director.
0:21:42 Thank you for listening to the Prop Sheet Pod from Prop Sheet Media.