In today's video, I'm joined by the CEO of Carta, Henry Ward, where we discuss leadership, the struggles of middle management, and how to be more efficient with your time in the workplace. Business owners and leaders especially those in middle management will get so much value out of this video.
Timestamps:
0:00 - 0:54 Intro
0:54 - 4:19 How Carta started
4:19 - 10:05 Henry's journey as an entrepreneur
10:05 - 13:08 Being consumer-centric
13:08 - 18:56 Tips for working with an active board
18:56 - 23:05 How to deliver feedback to your team as a leader
23:05 - 26:51 Entrepreneurship and the school system
26:51 - 30:24 How to help middle managers grow
30:24 - 35:26 Business lessons from 2 CEOs
35:26 - 39:19 Final thoughts
Thanks for watching!
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You're being over optimistic and you don't want to scare us so you're trying to do something. But let me give you the preview. We're going to see you in 90 days and you're gonna be on the other side of this. So you're going to have to admit to the problem and everyone at this table besides me cuz I'm ridiculous.

but the rest of the people here are much more straight and they're going to be pissed. so why don't you just tell us that shit's up now and let us help you for the next 40 minutes instead of saying it's all good? Because to your point, this let me hold it in and maybe I'll make it work by the time I see them and 90 days when you see them in 90 days and it's double bad. AKA You didn't say 90 days ago and now you're saying it's an 11 out of 10 issue whereas 90 days ago you were saying it's all fine AKA it's a zero or a one or two out of 10. You're in deep cuz you've lost Trust of the board and that's when the seeds start to sprout of are you the right person to run this company? Attention is the number one asset vayer Nation How are you? Another exciting episode of the Gary Audio experience.

Decided that we've done a lot of motivation. We're doing a lot of innovation, but I Want to get into operation I Want to get into the depths? Uh I Was really excited when the opportunity came to have this guest on the show because I think bringing leaders who actually did it are actually doing it are are Building B You know for me, building a business that from afar I admire in its longevity. It's not a fly by night. It's not a quote unquote unicorn even though this is probably a unicorn in the way.

but it's defied. But like you know, like it's it's not. it's a unicorn. AKA Startup that's a big company, not a rhinoceros with a unicorn with painting its horn and making pretend it's a unicorn AKA A lot of the startups that are grossly overvalued and then disappear off the face of the Earth because they were overleveraged and weren't actually building an actual business and I want to tap into some of the minds of the people that are doing it because so many of you are on your journey of doing it and so that's why I asked Henry to be on the show Henry Welcome please tell everybody your full name, what you do, what the company is, and a little bit about the company and I think we should get into a meat and Potatoes episode here of the audio experience.

Thank you for being on Brother yeah thanks Gary thanks for having me yeah my name's Henry Ward I'm the uh co-founder CEO at Carta uh you know we do. We're about 10 years old. we uh do we have three lines of business? Uh, we're about 350 million in Revenue about 60% of that comes out of our cor cap table business which where we serve startups and manage their cap tables. uh the another 30% comes out of our uh fund Administration business where we manage the back office of venture funds and do their their financial accounting and reporting to to their investors their LPS and then we have a a newer uh business which is about 10% uh of the business.
Now it's a couple years old and it's our private Equity business where we're we're basically managing the cap tables and fund Administration for private Equity um companies and and funds. How did it start? You know we we saw this Capt problem. It was sort of interesting. um people in 200 you know 1314 when we launched were were physically mailing Paper Stock certificates.

like like if you see the old movies with the the yeah with the railroads brother look at this this oh you've got four in your room yeah Facebook Twitter and Tumblr Beautiful. Beautiful. all pre pre- Carta uh 20 Fall 20067 Nice, nice, really nice. You know what the valuations of those companies was back then? totally totally and they're beautiful.

They're embroidered. you know they look exactly like the stock certificates when they invested in the railroads and uh and and we were still doing that in 2013. Uh and we said hey, can we do something like what PayPal did for cash? You know, can we dematerialize these stocks for De Vegas instead of um, sending paper? uh, instead of paying, you know, mailing a check or mail in cash? Uh, could we um, send Equity through through email the way PayPal uh, sent money through email? Can we? can we do that through the cloud and that was the original idea. uh uh, could we push all this stuff in the cloud and then once you did that, once you dematerialized uh, equity and put it in the cloud.

um suddenly the option value on that exploded. You know, there's so many things we could do. We could do cap table management, We could do option management, We could do portfolio management, We could do liquidity. We could do fund Administration It just it.

It took off we entire ecosystem once. Once you got things out of paper, how quickly did you know? This is a great question for the audience. How quickly did you know we got something here? You know we were in beta. I Think we kind of launched a free version of this product? maybe in July of 2013? I'm starting to interrupt I remember it vividly I was so pumped it existed.

That's awesome. The Con: The concept that I was able to just forward it to somebody, be like, take care of this and like the thing I needed to be done when I was making an investment was done. It was massive for me. someone like me that cares about time over everything like it was hu I Remember those early days like I was like I Remember thinking like this just changed my life? Totally totally.

Well, thank you for being an early user. it was. It was. Um.

You know it was a tough start. Like a lot of these companies where you're doing something completely new. You know nobody had bought C Capt software before 2014. Uh, it just didn't exist.

You know there there's companies where you're building something that already exists. Like like Mongodb is like my favorite example, right? People had databases. Mongodb was like I'm I'm building a better database and you didn't have to convince people to buy a database, You just had to convince people to buy a better database. Uh.
and and cap tables was different. Nobody ever in the history of the world had ever bought a cap table uh, software product before. and so you had to convince people to buy something that they never bought before. Uh, and they never thought they needed and so it was hard to get going.

You know it's hard to convince people to do something they've never done. Um, and we launched kind of an early beta in July 2013 that barely worked. uh uh. and then we started charging in in January of 2014.

That's when we're like okay and we earned our first $120 on January 7th from uh, a friend and Company startup in Austin Texas uh uh. And it was amazing. It was incredible. The first time you you build something as an entrepreneur that somebody pays you for is a magical moments I'll never it really you know what? That's a great call out.

I I I genuinely remember like the first Gillette deal with fer media AJ was still in college I vividly remember kind of the first things I Sold at my dad's liquor store when I was 15 Kenwood 1992 1990 Chardonnay like literally I can sit here and tell you Kenwood 1990 Chardonay from Sonoma Valley is like ingrained in my heart. This goes a little bit to why I want this episode Henry I view you from afar and we're getting to know each other a little bit here as a like an actual entrepreneur and what I mean by that is it's in when you like love the game, not the thing that has become which is like it's so cool like quote unquote everyone is you know, like I love playing sports but I'm not a professional athlete when you love the game like you can like I Don't think a lot of people can actually talk about the first thing they sold the modern entrepreneur right? Like yeah, they can remember when they raised the capital, they can remember this that the other thing but like the actual first client especially if they're five seven years in in this new era. But I can remember the first Wi is sold for my dad, the first client Bner Media had like all of it like vividly, totally totally it's it's amazing I I Remember we made $800 in January of 2014 and it was the most amazing $800 you know we made this year. We'll put a $100 million of bookings on the board right? But and and the thing is is even at you know uh, 2,000 employees? uh you know 350 million in Revenue going to 450 Uh I spent.

you know half my day I Talked to four customers yesterday that were unhappy and that's what you do. That's no different than when you're a seed founder like you're just if you love The Game You love talking to customers. Look right now. back to your point.

three Hold Am I right about this 3:45 pm today. Client issue: I have 2,000 employees. How many employees you got about 2 Also yeah, there you go right. It's amazing.
Keep going Yeah, no and and and you know so so you know at January we made 800 bucks we're like okay well at least somebody will pay us for this so that that was amazing so that was I guess Milestone One somebody paid us for something we built uh which was which was a super huge high and then I would say that the second one um uh was August of that year and we we we moved our you know know back then you still called you know to to order something you know uh and so we had a phone system and it was was one of these things you called in and you pressed you know one to talk to sales, two to talk to you know support and we changed our phone system and broke something so that when you clicked one and it went to sales it hung up on you. uh you know the classic startup story like we had no idea what we're doing and uh so it just hung up on on you if you tried to talk to a salesperson and we sold more in August than we did any month prior and we didn't even know until halfway through the month. Somebody C went in through support and was like hey guys I'm trying to give you money to buy your software and I can't get to anybody you know what is going on over there and I was like oh we have something people are beating down the doors uh uh to get this product and I would say the third one was we finally had so many sales orders we couldn't onboard them fast enough and this was in uh January of 2014 a year later sorry December of 2014 and we're going to Christmas uh and I told the sales team uh, all five or six of them at the time I said you have to stop selling, you're not allowed to sell uh I'm going to put you on a draw for for three months and all of you are going to be onboarding managers and we're going to close the doors because our customers are Furious because they bought but we can't deliver. Yeah, because we're selling too much and that was that was the moment Do you? Yeah, Do you think that that is an incredible common mistake of successful like.

Obviously a lot of people end up figuring it out like I actually think the story you just told. if you even have the talent and the product Market fit to get to that problem, you 7.5 out of 10 times know what to do in that moment to get to the next place. Sometimes technolog is not there. You might remember frster because you're a tech dude.

You know, like frster being down all the time really eliminated it from having the opportunity of becoming Myspace or Facebook right? I mean Twitter got lucky a little bit because there was no unique competitor. there was pounce if you remember um that PO for a while. but but I mean Twitter was a real problem in 2006 s eight just wasn't up y Then there's the other thing. like underd delivering on what you so big issue for me in a client service business because I'm completely human based.
you have a smart business I have a stupid business if I wasn't building something bigger on top of it and so you know I think I Think For us, it's very hard when you're scaling people. as you can imagine with technology uh or product it's a lot quote unquote easier when you get your supply chain or your Tech team down. but do you find that to be a common problem and then more importantly for the people that are in it right now, that problem like you've over promised and underd delivered. do you recommend? They take your track which is a drastic T tack or do you feel like they should do things that have worked for me in the past which was more of a okay it I'm just going to hold my breath and fly the Pl keep flying the plane but fix it while I'm flying the plane and make sure that doesn't get out of whack both.

What's your thoughts on that? Yeah well so we did this. uh uh, you know we didn't really have marketing back then so our our version of marketing was me uh and I and and my assistant and or chap of staff I think and I asked my cha staff I said hey, go talk to 50 customers and interview them and ask them how they heard about Carta uh why they decided to buy Carta and what that sales cycle was like and all of them kind of heard. a little bit different. somebody came in from a friend, an investor Google search whatever it was.

But the one thing that was 100% consistent 50 of 50 uh customers? uh asked somebody else who was a Carta user if they had what they had heard of Carta uh to decide whether to buy and so we knew that the most important thing we could get right is that when that phone call happened the the the person who did have experience with carda would say a good thing. that was like the number one thing. nothing else mattered. Uh and so so I said it doesn't matter as we have to make sure that the reference checks go well and if people aren't happy it it kills everything.

And I'm willing to take you know a three-month uh uh, closing the doors on sales uh to make sure that's always true and it was a tough decision right? You know to tell the board. hey I'm not gonna sell for three months. That's a tough tough conversation to have segue back to like me wanting it to be a meat and potatoes table. Talk to me about the pros and cons, not just from your perspective because you have yours and obvious there's been a lot of success.

Congratulations! So I have a funny feeling people are feeling pretty decent on the board. uh at least at this point. But tell the kids or the Ogs I I'll tell you who's a big listener to this Henry that I think we can inspire a 47 yearold, very successful corporate player who she or he feels they're ready. they're ready.

And because they've been successful for 25 years in that environment, are going to actually have like a real board and real investors, right? Talk me through your perspective. Effective, but more but more importantly I was going to say equally. but I'll actually say more important because and Through The Eyes of many of the founders you've been around over the last 15 years, the watch outs and the ways to best use a board. Let's do that.
Yeah! so I have two tips on this that have worked well for me. So one is, you know the boards are always hungry for information. They want to know what's going on, you know? Etc Uh and one of my favorite lines from the Ben Horowitz book is you know, apply pressure. either feel pressure, apply pressure.

and I think you know he's really talking about executive teams when the exec teams are like hounding the CEO and the CEO's like oh my God I don't know what to do. you know everyone's on me I feel so much pressure. he's like turn the tables, apply pressure or feel it I Think that's true with the board and so I used to tell the board you know? Hey I want to put you to work Uh and we had a what's called an adopted business unit program where I'd have the the board each board member would like pick a business unit so I'd have Matt you know work on cap tables and I have Mike work with the liquidity team team and they'd meet with the team once or twice a month and it was great because one, they helped me, they helped scale me in terms of the strategy and and sort of influencing the organization I could run a flatter organization that way and two when when the board meetings came up, they all had firsthand data. It wasn't just me try to explain everything like everybody kind of had data.

So when they're like Henry what's going on with the liquidity business I'd be like Mike what's going on with the liquidity business you know, um and so so it it really brought them brought them in. The the second thing I would say is um the gold to you know the the number one rule on on boards is don't surprise them like that's just it. Like as long as you never surprise the board you'll you'll be okay. Uh and so that takes a lot.

That is the classic mistake that very entrepreneurial de someone like me who would be like I'll figure it like never had a board before like I and I I I really don't have board life the where because I knew that this would be a huge mistake of mine and ironically I'm on boards and I help the Gary in that situation I see the C's doing the mistake I would make and I make it safe for her or him be like hey I know what you're doing. It's okay because I don't want to be a hypocrite I do this all the time. You're being over optimistic and you don't want to scare us so you're trying to do something. But let me give you the preview.

we're GNA see you in 90 days and you're gonna. you're gonna be on the other side of this. So you're gonna have to admit to the problem and everyone at this table besides me because I'm ridiculous. but the rest of the people here are much more straight and they're going to be pissed.
so why don't you just tell us that shit's up now and let us help you for the next 40 minutes instead of saying it's all good because to your point and this was I'm glad you went there because I really want to give you the I'm on the podcast all the time I can put out content to these people all the time I want them to hear different voices this. let me hold it in and maybe I'll make it work by the time I See them in 90 days when you see them in 90 days and it's double bad. AKA You didn't say 90 days ago and now you're saying it's an 11 out of 10 issue whereas 90 days ago You were saying it's all fine AKA it's a zero or a one or two out of 10. You're in deep because you've lost Trust of the board and that's when the seeds start to sprout of are you the right person to run this company and if you have a board that has say in you being AKA you didn't structure in a way where you could actually get ousted.

you better be real careful AKA Forget about overpromise under deliver, under under under promise to your board and overd Deliver Yes, uh uh, 100% and totally with you Gary I'll even raise you one which is like even if it's like you know you're you're preing Brad news Whenever anything you know it's like I think it's going to be a little controversial or you know people will have different opinions on or anything I do I do what I call the rounds which is like I text I call all the board members one-on-one and I say hey you know I want to give you a heads up at the board meeting I'm G to bring up you know such and such and I wanted to get your you know I want to preview this with you before you know it's a group setting so you can tell me what you think you know blah blah blah and and it makes them feel special. It makes them feel connected. You know they can tell you things that they may not want to say in front of Seven other board members you know Etc and it's incredible amount of work. Like you know to call seven people eight people and have the same conversation you know to to to do that.

but it's that work that instills the trust so that by the time the actual board meetings happen, everybody already knows what's going on. It's it's been so it's been quote unquote, sold before you even had meeting Totally. and and I like when my board members zone out in board meetings and like they're bored and they're like we've seen this like I I Actually people like my exec teams always like come out of these board meetings go I don't they I Henry were they interested? do they? you know, do they care and I'm like that that I'm like oh my God I'm I'm managing the board so well when they're like enough, we get it already. Like like that means I've overdone it I've overc communicated everything.

There's no surprises like yeah, when the board is literally bored. Uh, like I've done my job well. By the way, get your board bored is like a a book on managing the board. It's definitely a real blog post hen.
um, what's the biggest mistake you made in 134, 15, 16 as a leader that you're better at I talk a lot about me being better at Cander. I Used to struggle with delivering bad news because I have a disease that's called I Love my employees and I mean it I Love people. you get you're getting to know me a little bit here. I'm just them who I am like I really like people and I screw up and I've gotten way better and especially last three years.

I wrote a book that touched on it aggressively I Talk about it. My content. More Cander was my kryptonite if I asked you 2013 145 Henry versus 20223 going into 2024 Henry what's been the biggest Gap you've closed as a leader? Yeah well. I have two thoughts.

one on the on the cander side I've always had a problem with the kind of the Cander cander radical Cander thing. I I Remember remember talking to Kim about it and you know I I love Kim I think he's fantastic but I always said you know the problem I have with the book is it's a it's a one-size fits all like Radical Cander kind of works with no matter who you're talking to. you know whether you're talking to a shy you know 23y old first job employee or like your 25-year veteran CFO that you've worked with for six years right? Like it's it's the same And and everything I know about people is, uh, know your audience like how you talk to them? Yeah, yeah, it matters to your point. Kim's awesome like by the way I call it kind cander at vainer media because I think radical people feel like oh, let me give you the purest form of it which I actually think seeps into people's real struggle with cander.

which is they don't don't They don't deliberate with enough empathy, compassion, sympathy, and context totally I I would even go. So here's the I I do this all the time in my management training right? You go like go Okay so manager's working with the their employee and the employee not doing great. uh in the manager's View and the manager says okay, you know So I'm going to deliver the feedback and they basically say you know employee, you know I don't think you're doing great and you know I always ask you know the the the most important thing to figure out is it doesn't matter yet what you think, what what matters is what the employee thinks right. If the employee agrees with you and is like I don't think I'm doing great either that's a very different conversation that if the employee like I don't know what you're talking about I'm crushing it.

And so the the first thing to say after you say hey, I don't think you're doing great is what do you think right? And if they're like uh I don't think I'm doing great either You're like amazing. So let's talk about how how I can help right? that becomes a collaborative discussion uh of of fixing it if the employees like uh uh I'm crushing it I don't know what you're talking about that's a very different conversation right? and then the second you know if you go down the decision tree the second thing managers always do is um I say okay what do you say if they say manager, you're you're wrong I'm crushing it I don't know what you're talking about the manager will always what they do is they they double down they're like no no here. here's all the reasons why you're not doing good right and I'm always like that's the losing battle never do that right and my my advice is always to say to the to the to the employee I said oh amazing I'm so glad you think you're doing well. Why why do you think I don't think you're doing well and and right? So so you lead with curiosity.
Um, because that's the thing to figure out right? It's not. It's not the the question to solve is not if the employee is doing well or not. the question to solve is why. Why are you seeing the same thing differently? That's the question to solve.

You know it's I love you for that. Because we do something here where I train my leaders to say hey Henry in my subjective opinion from my purview which is all I can really rely on and the data that I've gathered from others I believe you're not crushing it instead of like this is definitive fact, right? And that really triggers people Because we know this: A lot of managers are wrong. Lot times are right, Lot of times are wrong. By the way, I Watched managers for years give feedback to people only because they wanted to keep them down because they knew that person was better than them.

Totally 100% idiosyncratic manager bias I think is one of the worst uh, diseases in an organiz I Couldn't agree more brother. Yeah, let real quick just to almost like we interrupt for this commercial break I Really do love your product and so one more time. who who's listening here should really discover Carta and why and what does it do and where should they go? Oh thanks for letting me do that I Really, you know what's funny people? I've done this podcast a long time I never do this. but I wanted to do this for two reasons: I wanted a steak and potatoes meeting which we're doing and honestly I really think I'm about to help a lot of people who listen to the show.

So I'm being a little selfish and I'm thrilled that it's good for you. Yeah, thank you. So uh, you know we serve uh, uh, uh, two types of customers. So one is if if you're an entrepreneur running a company, uh, whether it's you know a two-person startup, whether it's uh, uh, an LLC you know, um, small business in the midwest like we have products for you.

Basically we want to help you manage your your shareholders, um your stakeholders, your employees. So so we'll we'll help you on on understand the capital structure of your business, that that's what we do for for entrepreneurs. Uh and then on the other side, if you're a a venture fund manager or a private Equity Fund manager will help you manage your your fund and like Gary you're you're a customer of ours. you know for your Venture fund.
Um and we help people like you you know I have this kind of view of the world which is you know America as a country we're like great at producing. um accountants you know and lawyers and doctors like we're really good at that. um but we're really bad at producing entrepreneurs like we just don't We we don't produce them, what happens to them G to show you something Henry that is a this is my report card. look at my class rank.

it looks like mine. Yeah about that. you and I have started a company from scratch with 2,000 employees. knock on wood are doing extremely well.

The I mean it was literally the 11th worst student in my class. You're absolutely right. we now look I Actually would argue a different point I Actually think America is great at creating entrepreneurs which is why it creates entrepreneurs in the macro in the micro AKA School system. And like a lot of social norms, we have the inspiration for entrepreneurship here.

We put it on a pedestal. There's plenty of I was born in a place where we demonized it. It was called the USSR I was born in the Soviet Union you know and so I think that. But to your point, we definitely don't teach it.

You're either born with it and you fight the system. You're the one that really bothers me. Which I think is what you're touching on. You're born with it and the system and your parents take you out of it.

Which is the devastating one. Some of the greatest entrepreneurs were talked out of it to be lawyers. you know and do that crushes me. Um, so I I I Love where you're going with that.

So go ahead. Well well to your point. Yeah, you know, entrepreneurs in in America we're You know we're celebrated. But but we're the aberration, right? We're the weird ones.

To your point, your report card shows it right. You're you're the exception, not not the rule. Uh and uh that that's why I say like it's it's a weird thing and and it just goes from like the way the way we we teach school right School is taught. You go Kindergarten first grade, second Gr.

you know, 11th grade. you know, freshman in college and then you become a a junior associate and then a senior associate. and it just there's a ladder. and Entrepreneurship there's no ladder.

It even goes to like the way we do school like tests right? It's so weird. Tests you start at 100% uh, it's bounded and then everything you get wrong. you get, you get dinged and you go down as opposed to you start at zero and then everything you get right, you go up. Uh, and it's unbounded because that's what entrepreneurship is.

You start at zero and you go up and it's unbounded. Um, but but that's everything we're taught in school is the opposite. What? Um, what have you Noti Here's a good one. A lot of people for that.
You have 2,000 employees I have 2,000 employees. What does a middle manager call it a director wanting to be a VP Everybody's got different terminology, but like what does a middle manager in your company do to take it to the next level and H and you could be very specific of how it works at CA And how do you feel that maps to advice that I think we have a ton of middle managers? Great. You know, six figure salary doing their thing but really do want to grow. And from a CEO's point of view from a real entrepreneur and been around the kind of tech companies that are really.

there's a lot of companies that fit the profile of what you do and and and a lot of them are coming and are being built now and just And even a lot of them had to be at this point of the size of your and my company and that was 30 40 years ago. But middle manager? What are some of the things you're seeing that help somebody Propel to a a VP or SVP or EVP or take those next two steps double their salary, more responsibility, more challenges. Enjoy their day-to-day more. What? What are some of the cliche things you think about when you're trying to help a middle manager grow? Yeah, I You know I was um like when I was 18 I I enlisted in the Marines uh and I I went through kind of Officer candidate school and college and all that and some somebody said to me um he goes you know the the the difference between M military life and civilian life is in the military you're judged by the the worst thing you did and in the civilian life you're judged by the best thing you did and in in most companies middle managers are judged by the the worst thing they did right.

Your job is to not not mess up right and and to like, do the right thing and and be be popular and liked and you know all that kind of stuff and not piss off your boss and you know not have any dings. um and and that leads to a very defensive you know middle management core. Uh and and really a calcification of an organization. Uh I hope at Carta Uh, we're a company where we measure middle managers on the best thing, best things they've done.

and so if if that's true, uh, that really means like we forgive mistakes. we don't care about that kind of stuff. What we really want to see is a middle Manager Bend The Arc of Carta right? Like a middle manager. Just like they may may do six things that don't work out.

But boy, that seventh thing that they did WOW right? Like that gets on my radar like I'm like who who was that person that was in that meeting? What did they just do? Bring that person back to my office I Want to hear more about it? 100% Um and and and but that's really hard. It's really hard to build and and it's hard for them not to fear the ramifications of shining. Most middle managers are scared to shine because they know when they leave it becomes political and their boss BP whatever are like what the was that that's right and they think and they think that person can get them out before you and I can get them up. That's right it.
it's threatening right? because their boss is like one if my middle man. If if my manager you know that works for me, uh, makes a mistake, that's a reflection on me. So I'm going to punish that and then if they actually do something amazing right? uh what does that make me look like like uh they they're better than I am and so so that's why middle Management is such a like an I would almost describe it. It's like the oppressed know uh, middle class of of organizations and and creating a dynamic uh middle Management Corp I think is one of the biggest challenges of running a a growing organization I Couldn't agree more.

um um what have we not touched on in the last seven or eight minutes? Uh, you know on the on the scale and operational side you're you're sort of talking about the um what I would have done differently you know and how things are different from like the the first five years years versus the the second five years of this company and I would say you know the the the the job changes quite a bit for for the CEOs that are out there that are thinking about early stage uh versus versus late stage and you know there's this kind of inflection point where I used to be able to keep the whole uh company in my head like I I used to know the whole business in my head like I knew everything that was happening. Uh and there there becomes this inflection point where I feel like I don't know anything that's happening and it's like you know I also describe it as you know when I talk to early stage Founders Uh, nothing happens unless you make it happen right? That's that's what it means to be an early stage founder. It's like you. you are the Catalyst You you create the energy of the organization and then you get to you know the scale urac G and like things just start happening and you're like why are these things happening right Like like I don't want things to happen and they happen.

Let me ask question. This is a good one because for the hundred people in the next year and the thousands over the years that list, listen to this. For the 2,000 plus employees like you and I I'm G to ask you a question, how many, not just your direct report the SE Suite how many family members do you have in the 2000 that are your eyes and ears, they might be a director, they might be an Ops they might be an HR I just want I'm curious what your answer is when I say family members, you know exactly what I'm saying. The homies, the one that eyes and ears, the the double agents like the ones that are really helping you mitigate or get clarity on all this to your point: I Think we're opening an office I didn't know about that I'm like beside myself about from a meeting this morning.
Dead serious. A physical office. Um, how many of those do you have of 2000 right now? Go? Yeah, uh. probably two dozen.

Yeah, um I should have more. Uh and but not a bad number. not a bad. I Would I would say two dozen 24? I would say I would say I have 40 and I would like another 12 as well.

And but I got I have a company that started with a bunch of kids that have worked here their whole life. We're only 14 years old. similar to you and a little bit older. and I think you know.

Actually, so you're what? 10 years old now? Yep, how many people have worked there for eight years or more? Uh, less than less than 15? Got it? We got a little bit luckier and I make sense Equity You you had different things that probably triggered that. We got really lucky with our 11 plus of that 14e run. There's enough that allows me to have more of them Anyway, not to lose the final minutes here. Everyone who's listening make as many family members as you can if you plan on growing big, big.

but remember to be a family member that requires you putting in the work for them to take you in as family to be able to have what we're both talking about which is very needed at Scale. Yes to totally and so knowing like I just have you know someone that uh you know is in is in London and I'm going to London uh next week you know to kind of Vis the office and you know I have my person there and I called called her and I'm like hey tell me what's really going on over there you know I I get the reports I I get it through the chain of command but like tell me on the ground like what's what's really happening and it it's like super uh super powerful and having those people uh is super important. There's also this kind of you know you know this because you're the the founder uh CEO as well as I am. There's this big difference I I Talk to Executives about this all the time.

You know what's the difference between working for a Founder CEO versus a professional CEO night day yeah hold on I Be inappropriate. like just there's nothing is a bigger change in the history of a organization that's destined to be big than the day the founder CEO she or he leaves. Nothing is a bigger day. That's how different it is in the history of the company public IPL Nothing totally.

it's a completely different culture Dynamic you know and and just the the the the the way that you work like we've had terrible success bringing Executives in that have never worked for a Founder CEO before. uh and then they work for me and they they just think I'm a maniac understandably like compared to every you know CEO that they worked for. they're like God Henry is just is impossible. Like how do I work with this guy and then you you work with you know Executives that have worked with founder CEOs and they're like okay Henry's just a he's just a normal founder CEO like that's how that's how these people roll.
Um, it's such a different different framework paring shocks my friend. What what things of business or or Carta or startup or pop you want to talk about Travis Kelsey and Taylor Swift You know, like every other freaking human on earth. by the way, there's no more cliche. New York Jets thing my real passion, my true love then the at the height of this Taylor Swift Kelce thing the Jets are playing on Sunday Night National Football the most watch game not even Monday night anymore Sunday night Taylor's gonna be in the building 10 million people that have never watched a football game are GNA watch because of all this hype and the Jets are at the low low point.

Maybe they're franchise with the hype of Aaron Rogers and the Achilles and we're not playing well. this is the most Jets game ever. Totally. Anyway, two minutes on anything you know.

Actually let me say it this way. you were thinking about this podcast. What did we not touch on that you either wanted to touch on or thought we might touch on. You know what? I'm excited about? uh talking with you Gary is I I Do a lot of podcasts you know in in my industry you know we do.

You know we're talking Venture you know and so on. and you know one of the um the things I I spend a lot of time talking about. we we call it crate ownership right? I have this kind of view of the world that you know um, labor used to be surf Dum where you were sort of you were you know you were legally free but economically indentured I think we're in the era of payroll today where you people sell time for money. um uh and I I think the the future of of Labor is is really going to be an ownership era you know and I think you know the Futures here.

it's just not evenly distributed and we see it in in Tech and you're starting to see it in other Industries you know and and um entertainment and sports. You know the PLL Professional Lacrosse League gives Equity to to players starting to see it in other you know the NBA starting to think about it you're seeing in other Industries and so one of the things that you know excited is you have a broader audience outside of of tech is you know can we start catalyzing more companies thinking about ownership and employee ownership? uh as a way of of compensation? So that the next uh era of of Labor will be an ownership? uh, ownership one? I Think that's right brother. especially if you nerd out on the blockchain and what that technology will enable and really understand. Not the not the speculation of the Nft market or the hype of the cryptocurrencies.

like if you really understand what the blockchain will do for the thesis you have, it is the underlying technology enabler of that guaranteed truth? 100% Yeah! I Enjoy this my friend! Great job Gary Thanks! So much So much fun! Thank you one more time. Where should everybody go to check out your company? Which I think a lot of people should be using Uh card.com Cta.com Thank you and everybody you know this I Don't go for the hard push and you can say see he wasn't looking for the push I was looking for him to push I think a lot of you need this because you know in the same way I'm pushing you to make 30 minute meetings 15 We didn't get to this one hour meetings being 30 minute meetings not we don't need 21 people in this meeting. We need 13. Everyone's like oh I'm stretched I'm like what about managing your time and so same here.
This to me is a Savor of Time Versus the way you're doing it and doing it better. So anyway congrats I I'm I've been very impressed for a long time from Far Henry and I'm I'm thrilled we stumbled on each other I'm thrilled you took the invite to be on the show and I Love this time together! Yeah, super thank you Gary Thanks so much.

13 thoughts on “How to operate and scale a business”
  1. Avataaar/Circle Created with python_avatars Marc Kuhn says:

    Great insights here you guys! Appreciate the video

  2. Avataaar/Circle Created with python_avatars Rhino Squad Virtual Assistants says:

    Thank you so much for bringing Henry on, this was a great conversation. I picked up a lot of great tips.

  3. Avataaar/Circle Created with python_avatars CutieBerry says:

    This man is very smart and intelligent😊 I really admire him, and watching him makes me learn and appreciate him as a new vlogger. He said we always have break time of 2hours, so why don’t you use it to make a content😅 so here’s I am making content often , thank you for the advice and more please❤❤❤❤❤❤❤

  4. Avataaar/Circle Created with python_avatars Motivation Doctor says:

    Gary for President 🌶️

  5. Avataaar/Circle Created with python_avatars Jamila Miller says:

    I love this topic. It’s very honest and it helps beginner’s understand communication and accountability at high levels.

  6. Avataaar/Circle Created with python_avatars Happy Glass says:

    The best time for General Motors employees was when they had a share program. They literally bought in to the company. Culture was great (they had baseball teams) and occasional surprise pizza lunches. Production was excellent people were proactive because they were literally owners. Then new mgmnt came is and crushed the people’s spirit, treated them like machines and offshored their jobs to people who could not buy the cars they were building. And now Toyota is number 1 seller.

  7. Avataaar/Circle Created with python_avatars Mini Mac says:

    one of the few scenarios where I feel two entrepreneurs were on the same page at the same time and provided value in a way that was timeless. The dynamic and segways between conversation were amazing!

  8. Avataaar/Circle Created with python_avatars Huljund Romeu says:

    I can't wait to come from work to watch your videos

  9. Avataaar/Circle Created with python_avatars Adriaan Pretorius says:

    Crazy vee💔

  10. Avataaar/Circle Created with python_avatars Angela Moulton says:

    solid content

  11. Avataaar/Circle Created with python_avatars OHANA BEACH SUITES CDO says:

    Great material here! Love it Gary!

  12. Avataaar/Circle Created with python_avatars MAI Samik says:

    Btw of course everyone will be pissed when they find out it was all liquidity issue all years long. Why do you think I have been bitching so much so long to get my own money. Will be interesting how everything will unfold.

  13. Avataaar/Circle Created with python_avatars MAI Samik says:

    What if I said its bad 18 months ago and you just decided not to listen aka answer with you gonna figure it out? sounds like reality check coming to you.

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