Grinding is overrated: the richest people never retire

I'm 35 now. What advice would you give to your 35 year old self? Figure out a way in life to pause. Find your pause. Find your thing that allows you to step away. Find a new way of looking at whatever the situation is, business, personal, etcetera. If you pick your habits that are personal to you, I think you you design A life of N of one your life. I think you'll find more success in life. The more that we let habits come in from somebody else, the less happy we are.

What is your favorite city to travel to? Is it Aspen or the Hamptons? I love both. I love surf lodge in Montauk. I love the snow lodge in Aspen. I actually like going to Tokyo, Japan.

Who is the crazy successful but also low key serial entrepreneur who sold his startup for $850 million to Oracle and has invested in over 100 startups himself? Today we talked to Jonah Goodhart and side note, he's also the co-owner of one of the hottest spots in the Hamptons, the Surf Lodge. We're your Co hosts. I'm Cherie, I'm Jean, and we're the Tiger Sisters. In this season of Tiger Sisters, we interview the most amazing set of founders, CEO's and business leaders.

First, we talked to Jonah in an interview and then right after that Cherie and I talk about all of our takeaways from the interview in kind of like a Business School case study method way. We'll get to the interview. Right after this break. Hey, guys, quick. Break to let you know that we now have merch on Sisters matcha.com. We have sweatshirts and T-shirts that we designed ourselves. Go check it out and please rate US five stars on Spotify and Apple. Podcasts. These ratings are so.

Important for the distribution and. Survival of Tiger Sisters podcast. Thank you for your support. Jonah, why don't you start with

introducing yourself? So I'm Jonah Goodheart, I am the Co founder of a company called Mobian. We're building an AI powered contextual classification engine. So said really simply, we want to build a new way to look at the content on the Internet by leveraging AI. OK Jonah, I'm 35 now.

What advice would you give to your 35 year old self? The advice I would give to my 35 year old self is figure out a way in life to pause. The idea, I think of pausing is incredibly impactful. And by pause, that can mean taking a break. That can mean stopping what you're doing In the religious world, maybe it was on a certain day. We don't do things. And if you sort of step back from that, it's essentially taking a pause. It's stopping.

It's not being a part of it. In some ways, it's the only way to get out of some of these cycles that we're in as a society is just to say I'm going to pause and be a participant in that for some period of time. And So what I would say is find your pause, find your thing that allows you to step away and find a new way of looking at whatever the situation is, business,

personal, etcetera. Yeah. Oh, I fully subscribe to that because I think my generation, like millennials, a lot of people are discovering sabbaticals for the first time, especially a lot of people who are like, in their 30s and haven't taken time off for like, you know, life milestones such as like taking like a month off for, you know, your wedding and honeymoon or taking maternity

and maternity leave. Like people are now like baking in sabbaticals into their like, overarching career plans. Totally. And I think it's also just on a daily basis, figuring out what do you do during the day that gets you to step out of it, right. So there's these things where we feel like we have to take some action or we have to respond or we have to post something on social media or go back and forth.

I think the only way out of that dynamic is to pause is to disconnect is to say I'm not going to be a part of whatever that thing is. And so I think figuring out what is it in your world that lets you pause on a daily basis? Not be on e-mail, not be on text, not be on social media, not whatever The thing is that is pulling you in One Direction or another. Stop doing it for some period of

time as a daily habit. I'm a big believer in daily habits and that if you pick your habits that are personal to you, I think you you design A life of north of one your life. And if you pick your habits that matter to you over time, I think you'll find more success in life. And I think that the more that we let habits come in from somebody else, the the least, the less happy we are. I. Love that.

OK, Jonah, what was your first job and how how did that influence your career or like how you approach work today? Yeah, my first job was working at Dairy Queen, painting a fence and picking up trash, so. Huck Finn. I thought it was great. I I loved it. I loved the idea that I was independent, that I could make some money even though it wasn't much money, but the idea that I can do something and feel some sense of, of pride, of, of being

able to be independent. I think that the idea of working hard was instilled in me at A at a young age. And I think there's something really, really great about it. I think that we have this idea so-called retiring and you know, all of these different concepts that we sort of created a society and it's great if you want to retire, whatever that means to you, Wonderful. More more power to you.

But I think there's something that we've sort of missed. And I think the thing that we've missed is what my oldest brother calls the happiness quotient. And the idea of the happiness quotient is that you see people who are 100 years old and they don't seem like they're the healthiest person. And they eat bad food and they're not exercising. They're not doing the things they're supposed to do.

And yet they live to 100. And you see other people that are in incredible shape, and unfortunately, they die early. And the difference perhaps is not just whether they follow a healthy regimen. The difference perhaps my oldest brother would argue, and I agree, is something that we don't totally understand. And that has to do with happiness and the the idea that if we're happy, if we're living the life that we want to live, that maybe that contributes to

longevity. I see people like Warren Buffett in the business world or Charlie, it was 93. I think Charlie Munger died at 99 1/2 years old. Growing up eating, you know, fast food and, and soda every day and not working out yet lived a lot longer than Warren Buffett, still living than a lot of other people. I think the difference is they figured out happiness. They figured out what was happy for them, what they enjoy doing,

what what drove them. And I think there's got to be some, some of the calculation has got to be that it can't simply be that you have to eat perfectly and live this perfect healthy lifestyle because we see lots of examples of people that that do that and they're unhappy. And so I think it's trying to figure out how do you, how do you get the happiness for you? The happiness quotient. I like that. I'm going to start start quoting you. Quoting your brother.

OK, How about what failure in your life are you most grateful

for and why? Well, I have had plenty of failures. One of the failures in my life, in the in the business world was that we built a company, my middle brother and I in college and we were doing phenomenally well. We thought we were the top of the world, that we had figured everything out. And we even got an offer to sell our company to Lycos at the time and we turned them down and we thought this company is never going to never going to stop growing, crushing it.

It's going to be incredible. And within a year that the business had almost completely gone out of business and of course, the offer to sell the company was no longer there. Now, as it turns out, had we done that deal, we would not have ended up on the path that we got on, which is we partnered with somebody else. We ended up helping create another company, which led to a third company that we were involved in. And have we not done that?

We wouldn't have gone down the paths we're on today. And so I think you don't know, I think Steve Jobs actually said, you don't know how these things are going to connect in the future. And so you, you can't sort of judge it too much in the in the moment, but at least if you have a belief that things happen for a reason and I and someone who believes that things happen for a reason.

And so you don't know what that reason is going to be today, But keep a positive attitude as best you can and and keep driving for happiness. Yeah, I'm the same. The older I get, the more I subscribe to that. But were you like, devastated at the time? Yeah, I mean, we were definitely seriously disappointed because it felt like it's, it's worse to feel like you had something that you lost, right, if you didn't have it at all, if you didn't

get to that point. Prior to that we were a couple of kids on financial aid at, you know, college. So we didn't have anything. So there was nothing we were concerned about. But at that time we were, we were given an opportunity for life changing financial reward and etcetera. And we turned it down. And so you feel like, oh man, we really made a mistake. We really messed that up. And, and you start sort of

questioning everything. And I think that you, you don't know how that road is going to, is going to lead. And so if I could go back and talk to my younger self, I would say don't sweat it. Yeah. It all happens for a reason. I love that.

What's a hot take or like a contrarian belief that you have in your industry? Well, one of the things I've been in the digital advertising and advertising measurement industry for a while and digital advertising now for 26 years or so. And one of the things I think that I've learned is that advertising is just about people. And I think if you mentioned advertising to people, they go ads. Everyone loves to hate ads, right? They think, oh, it's an ads thing, it's whatever.

Yet advertising, if you think about it, is storytelling. That's what advertising is. It's literally just paid distribution for storytelling and storytelling is the most foundational concept of, of humanity. That's how we communicate. It's how we've communicated over centuries. And so for me, I think there's a misunderstanding at some level of what ads are when done well, right. And, and in any industry, in any category, when not done well, nothing is good in that in that

case. But when done well, ads can be inspirational. They can be certainly informative, certainly fun, and it is truly a story. And stories can be heartfelt and meaningful and drive us and help us be happy. You're really good at storytelling. That was really good. OK, just two more. What is something that you feel like is really valuable that you've gotten out of conference or like what what were you looking forward to most from conference? Like, I don't know those.

The number one thing I get out of conference is just the interactions of the people. Imran is such a force of nature and he brings together really not just people who have done something interesting in their lives. And all the people at those events have done something interesting, but they're people who are intellectually curious, who want to learn, who want to talk, who are not just coming in and leaving as people do at some events.

People are coming here for the purpose of interacting with the other people who are here. It's small event. It's invite only. I'm honored that I've been able to attend Imran's conferences since he since he started. And there's something special that that he has curated here. And it's, it's a group of people who want to learn, who are humble and who are willing to put themselves out there and,

and learn something. And some of the people you walk around and you go out, this person leads up 10s of billions of dollar public company, $50 billion public company, $100 billion public company. And yet they're walking around with everybody else and not just there, but having conversations, engaging, wanting to learn from you and, and vice versa. And so I think he curates just an incredible environment where

people want to meet each other. And in the end of the day, I think business is about people, right? The thing that we misunderstand about AI, the hottest topic and certainly something that I believe as probably most of us do watching this, that it will revolutionize the entire world. It absolutely will. But in the end of the day, I in the end of the day, AI is here to serve people. We don't go away in this whole AI equation.

We may change some of the things we do, but in the end of the day, it's still we're still going to be there. We're still going to eat food, we're still going to interact with each other. We're still going to have dreams and visions and goals. And AI is going to be there to help support us as human beings. And so I think that the interesting thing is humans plus AI and how that that future works, but it is AI in service of of people.

What is your favorite city to travel to when you're taking a break and is it Aspen or the Hamptons? My favorite city. I actually, I don't know if I would say Aspen or the Hamptons, although I love both. I love Surf Lodge and Montauk. I love the Snow Lodge and Aspen, but I actually like going to Tokyo, Japan. And the reason I like Tokyo is because it is so completely

different from my world. It is one beautiful and imaginative and creative, but it is an environment in a society that cares about things in a really unique and special way. You won't see trash all over the place as an example. You will see people that take honor in what they're doing in their day-to-day lives and you see just a incredible environment. A lot of people, a lot of business still. People transact. Lots of things are still happening.

It's a successful, very successful society and culture, but it's very different from other places. And so I think going to Tokyo and going to Japan in general is an opportunity to pause and really think differently. Certainly I'm American, I was born here, and so being able to be somewhere that is totally different and looked at things that totally different way is is incredible and fun and inspirational. So I would say Tokyo for a city and Japan are the country. Oh, fantastic.

I'm we're going in November. Yeah. OK, well, that's it. Great job.

Oh my God. What an interesting conversation with Jonah. That was really special, super thoughtful, and I'm so excited to get into the takeaways. But before we do that, Please remember to like, comment, and subscribe. We would so appreciate it if you could rate US five stars if you're listening to us on Spotify or Apple Podcasts, and we'll get right the takeaways after this break. Hey everyone, quick break to

share something special. Sisters Matcha We've launched limited batches of ceremonial grade single estate single cultivar matcha straight from the family farm Sheree worked on in Japan. It's pure, authentic, and crafted with intention. Head to Sisters matcha.com to grab yours before it sells out. Make matcha your daily ritual for lasting energy and. Focus.

And we're back. Let's start with Cherie. What was your first take away? So something that I think the viewers and listeners will not see because it was off camera is that before this interview that we had with him, we literally sat down with Jonah for like an hour and. You know, like longer than an. Hour I lost track of time, but like, we sat down, we talked about our life stories.

He's so interesting and so incredibly humble and like, he doesn't even mention it because like in this interview, he just doesn't say anything. He's literally sold one of his previous startups to Oracle for $850 million. Wait, I literally forgot that. Isn't that insane?

I forgot. That yes, and of course he doesn't mention it because like all these, I think very super successful people are just like incredibly humble and don't like they don't hype themselves up. So Gene and I need to hype them up. He's also worked with his brother. He had, he told us that he has like more than one brother, but he's like worked with like both of them in different capacities, which is so interesting because like I think it's special working with a family member.

He's talked about that and also he is part co-owner of the Surf Lodge in Montauk and then also a similar one but a ski version in Aspen. He's just like, so humble, so interesting, so smart and thoughtful, but like. Yeah, he's kind of a renaissance man, He really is. And he also like, I don't know if this like comes across as much in the like, interview setting, but in our conversation with him, like I have to describe him as mesmerizing.

Like, why else do we have did we like end up talking to him for like an hour and a half? Like learning his entire life story, like telling us telling him our life story? Like he's just. He makes you feel special, like he's one of those people. Like, you know how they always say that there's like people who, like when you talk to them, all they focus on is you? Yeah, That's like he that might. Be his superpower. I think so, yeah. Which is why I think in this interview he made lots of eye

contact with. The audience, he's mesmerizing. He's mesmerizing. So I just wanted to put that in there because I definitely know that did not was not mentioned in the interview, so. Yeah, we like, didn't talk about his accomplishments at all. We're so rude. We're like, just tell us your advice. Yeah, give us advice now. Yeah, I really liked that.

Jonah, when we asked him about his first job, he brought up working in Dairy Queen. The biggest take away for me is that, like, no matter what you're doing, no matter what your job is, whether you're a kid or you're an adult, like do it with pride. Every job is hard, and you can always find pride in what you're doing.

And I think those people who are who are able to do that just like go away further, you know, like people can tell that you're like proud of what you're doing and proud of the craft. Yeah, like recognizing the value of work. Absolutely. Nobody works anymore.

Nobody works. Anyone, if you're feeling like honestly with yourself that you're like not proud of what you're doing or you're not proud of your output, your deliverables with work, then like maybe you're not working in the optimal role or job that is like right for you at this right time. Jonah was saying that some of the things he did was dairy at Dairy Queen were like painting the fence, picking up the garbage.

Like I don't think he was like, this is going to be my role forever and this is my like dream role in life. But he was like, this is where I am now and I have pride in what I'm doing in my contributions. And he he said also, I think he said that it taught him basically just the value of hard work. Like, it's not like a like a new concept, but I think having that early on in your life and learning to kind of like also enjoy what you do is important.

Because he also then related it to the idea of the happiness quotient and the idea that, like so many people think of work as just something to like muddle through from 9:00 to 5:00 from the ages of, you know, 18 to 67 or whatever it is. And then you finally get to retire. He is very much of the mindset where he was like, no, I think the happiness question is if you enjoy what you do, you never want to retire. You want to keep doing it.

And he used the example of Warren Buffett and Charlie Munger where they were and still are investing well into their 90s. And they're, you know, legends at. The Craft. And like, that's kind of his, like his role models. If you love what you do, you'll never work a day in your life, is what they say. Not to be trite. Not to be trite, but like when I see professors at Stanford, especially the ones that are like pretty old, like objectively like in their 70s, they have many decades of

wisdom. Like I think of Glenn Kramon and Joel Peterson, Irv Grossbeck who are in their 70s, and also Irv Grossbeck I think is 89 like and still teaching at Stanford GSB. Legendary legend that's like, actually legendary. Well also I had a coffee chat with him, he was kind enough to like. He wasn't even my professor. I didn't have a class with him but he did a last lecture series with us. That really touched you? Yeah. I was like writing notes the

entire time. And then I asked him for coffee. We sat down, I told him my life story, and then I was just like, So what? What's next for you? Like in in teaching in your journey. And he's like, he's like, well, I'm going to be teaching at Stanford until like I start ruling. I love that yes. And I think to me that. Even then, why let drool stop you? Seriously and gross. Grossback needs to to widen his horizon. That's. True. I think to me that is a model of

happiness. I think it keeps the brain going. If you can keep working into your 70s and 80s, late 80s, that that is a goal of mine actually. I don't know if I love what I'm doing. I don't want to stop working. It's exciting to me. Yeah, because it's not really, I guess it's work, but you're kind of, you're building, you're creating, you're generating. Well, now they're empowering too, and like bringing up the next generation. They feel like they have a hand.

And like, yeah. Curating, massaging the minds you know of young people. I've always thought that after I retire, whenever that is, I would become a professor. I've had this like sort of dream ever since I went to Dartmouth that I would then move to Dartmouth, buy a house on Occam Pond which is the main pond where. People go ice skating right Where people. Go ice skating and then be a professor at Dartmouth. You would want to live in Hanover. I don't know. You would fly in.

From Washington State. Yes, exactly. Long commute. Yeah, that's pretty long commute. Yeah. I think it'd be fun to be a professor. I I also would want a role where I would have influence over young minds and also. Power. No, it's more like. Guiding. Yeah, like I think guiding people, helping people learn, and also like, I think it's really interesting, like what

Imran said in our conversation with him, like having a. Pulse like that's true and. Checking in with young people and that's true what's going on all the time. Like how exciting if I'm when I'm 80 and I can have friends of different generations who are in their 20s and 30s and they'll be like on like the hippest whatever. Like they're not even born yet when I'm 80. Like those people are not even born yet. Can you even imagine? They're -60.

Or maybe they're born. Actually, they're born right now. Okay, you know, it would be really like a kind of like cool goal or North Star is for if you're like my goal is to be the coolest 89 year old everyone knows and then also for me to like still be friends with people of all generations at any age. I think that's hard. My speculation is that I think that's hard to do. But if you can achieve it, like, you will live a very rich life, very rich life.

I can't. I mean, if you're 89 and like, you don't have grandchildren and you're not like, friends with, you know, people of that age, like, how do you even meet young people? Like you guys are in different spheres, like you don't really come across one another ever socially. Well, I mean, I figure, you know, a lot of my friends will be young because I'll be dating like a 25 year old AI, you know? Well then, will your friends just be a is? The AI will listen.

In the future the AI will have both AI and human friends, so it'll be a mix. OK. And they'll be embodied AIS. I didn't. Know what you were going to say you were going to be dating a 25 year old, AI. I thought you were just going to stop at saying you're dating a 25 year old, which I was like sure, go give more power to you Mama.

One take away that I really liked from Jonah that seems simple but is hard to execute, he said. Figure out a way to pause, and I feel like there's so many different ways you can interpret it, right? Because a pause can be any length. That's what you. That's what he said when you asked him what his advice was to his younger self. Yeah. I was like, what's your advice for your 35 year old self? Yeah, he said figure out a way to pause. And like, initially I had

thought he met. Like the way I interpreted it at first was I thought he meant like take a sabbatical. Yeah. Because I think like at 35, usually you've been sort of like grinding in your job and like rising through the ranks and like building up your career for like 20 or so years already. Wait, not 20, like 15 ish, something like that. But then he also meant it in a sort of like daily way. Yeah, I took it as a more daily

way. That was my interpretation of it. One of the examples that he said was he meant it in like a weekly way. He was like, oh, like, for example, you have the Sabbath. That was like the original intention of it is every Sunday, God was like, put down your smartphone. He's like, put down your slaves. Put down your, put down your hieroglyphics. And just enjoy the people around you. Yeah, like something like that,

like gather. And so I guess I actually like that it's kind of vague because there's so many different ways to. Apply it, yeah. But all of them are true. That kind of makes me think about my schedule. Now I you and I are working like every single day. Should we have a day of pause? Yeah, as God intended us to have. Like if we wanted to instate it. Yeah, a little bit. More and be more intentional. Yeah, about it. Yeah, yeah, yeah, yeah. We kind of do that on Sundays.

Like when we had our like groove, we had like our cardio dance class, we had our farmers market that was really nice. And of course we like built in work, but I like, I like that routine that we had. Yeah, and it doesn't have to be Sundays, although I guess it's good because then it would coincide with like most other people. Right when like stores are off so closed sometimes or restaurants are closed early, you know, like people are trying to rest as well. Yeah, yeah.

But I do think like you're very good at building it, at baking in moment of pause, like on a daily basis. Yeah, cuz you make the matcha. Oh yeah, yeah, yeah. She makes the matcha. I know you're gonna, like, give me a backhanded compliment. You're like, you're so good at resting. You're just so good at resting. You're. So good at not doing it you're. So brave in taking the time that you need every day.

To like not do anything. When I am just like working so hard, like on the side and you could see that I'm like killing myself. But you're still brave to honor your truth. Thank you. Rest yes, thank you. I mean, honestly, I think I should be doing it more because like, I don't know, it's just a lot. We're grinding a lot.

Yeah, I also think like not to like talk too much about this topic, but there also is a difference between like active rest and then like distracted rest 'cause I think I do a lot of like distracted rest because my way of like winding down and like disconnecting I guess is like watching TV or like it has been recently. And so, but you're not really like resting, you're still consuming, even if it's something as like mindless, like beautifully mindless as like

Love Island, for example. Famously Jeans favorite TV show. It's not my favorite TV show. I just think it's one that a lot more people should give a chance to. And you know, you don't need to be snoppy about it.

What do you think about disconnecting that? Like if you were to trade in because you only have a limited amount of time to rest, what if you were to trade in your connected rest to disconnected with disconnected rest, like just to get off Wi-Fi and you've been doing that, you've been taking walks and stuff. But like, I wonder if you could do more of that to like actually feel more rested. It's hard because sometimes when I'm doing my like TV watching,

I'm still multitasking. I like I'm still doing the rest at the same time. That's not right. Resting. Yeah, I don't know. No, it's it, There's not judgment. It's just, I think an observation like that's not resting and maybe that's. Also, it's like relaxing, but it's not really pausing. Not yet. You know she's trying to. She's trying to put different labels on it. Your brain is still working one

way or another. Like I think you should do water coloring or your jewelry making like that is like, to me disconnected, more disconnected. If you're looking for a way to pause more rather than relax, because sure, maybe they are. They are different sometimes. I say good things sometimes. I'm saying because I don't know if I agree with her, but we don't need to get much more into it. What do you guys think? What's the harm in trying?

Yeah, OK. Well, let us know what you guys think between like resting, pausing. Do you have like a routine around it? Yeah. I don't know if it's partially

because he's been so incredibly successful, but he's, he's very much of the mindset of, you know, things happen for a reason. Like he, he said that like a few

different ways. And I think like one of the things that he reflected on or one of like his experiences was that he said when he was really young, he and I think his brother had started a company and they basically they had made like what at the time was a massive blunder of turning down like an acquisition offer for what he says was a life changing amount of money that like wasn't even ever imaginable to them at

the time. And after they turned it down, like, the opportunity basically, like, went away. Like, the company kind of crumbled. And I think he spent, like, a lot of time. He didn't say this explicitly, but I think it's like, only natural to have a lot of regret after that and be like, oh, my God, I made the wrong decision. Like, how could I have done that? But it ends up being that, like, that is what eventually led him to start that next company that

then he sold for $850 million. And then like let him do on like all the things that he's achieved ever since then. Yeah. So I don't know. It's like one of those things where it's like, is it attribution like backwards looking attribution bias? Is it? Is that a bias? Just like if you're like telling the story, being backwards, looking like you can attribute one thing to another when like maybe they weren't actually related, but he he thinks that they're related. Yeah, right.

Life is all related. Well, he quoted Steve Jobs. He was just like, it's this famous Steve Jobs quote where Steve Jobs in his like 2004 commencement speech or something was just like, you could Only Connect the dots looking backwards. You have no idea. How these things lead to one another. But like, your life is all related, yeah.

Yeah. So I think sometimes it's important to remember that when things seem not great because, like, I don't know, there's always going to be a time, I think in everyone's life when you're like, holy crap, I made a huge mistake or I think I've made a huge mistake. And when you hold on to, you know, decisions that you've made with, like, a lot of regret when you could just potentially spend that energy on something that's more forward-looking.

Yeah. That's definitely something that, like, I personally try to have been trying to work on

like, the last few years. And one of the things he said is like, he's like, I remember he said something about like, oh, it's almost better to have never had something or like known that something was offered to you, then to, to lose it, to feel like you've lost it. I think that's very much like human nature, because human nature is to be loss minimizing as opposed to like gain maximizing or something.

Like people are always more likely to want to protect downside and not lose what they have versus like put it all out there to try to gain something more. Yeah. I think it's challenging day-to-day to like, have that mindset. But it's like. Obviously, like he's so successful that is just like, oh, this is what the mindset that he's had and how it's helped guide him through life and he could connect to the dot. I was just like, I kind of love that. I want to I want to be reminded

of it every single day. Thank you guys so much for

tuning in to this episode of the Tiger Sisters. Please remember to like, comment and subscribe. And if you're listening to this podcast episode on Spotify or Apple podcast, we would so appreciate it if you gave us a five star review. It only takes a few seconds and it means the world to us. Thanks guys. See you next time. Bye.