I asked everyone from a billionaire tech founder to a former Navy SEAL commander what it means to be successful, and money was only an afterthought

Sarah Jacobs/Business Insider; Hollis Johnson/Business Insider; Samantha Lee/Business InsiderSuccess isn’t just about money. From left: Jocko Willink, Sallie Krawcheck, and Sam Yagan.

When success is discussed in terms of careers, it’s often referring to wealth and influence. But after many interviews with people at the top of a wide variety of industries, we realised that those metrics don’t mean much on their own.

We’ve compiled our favourite answers to the question at the heart of Business Insider’s podcast “This Is Success”: “How do you personally define success?”

You can listen to the full “Master Class” episode here »

We start by examining the nature of attaining success with a reply from LinkedIn cofounder and billionaire Reid Hoffman, and then explore how people from former Navy SEAL commander Jocko Willink to media mogul Tina Brown measure success in their lives.

Read some of our favourite answers below:


LinkedIn cofounder and tech investor Reid Hoffman says success takes a mixture of luck and skill.

Steve Jennings/Getty ImagesLinkedIn founder and chairman Reid Hoffman at TechCrunch Disrupt SF 2016.

Reid Hoffman: Some people who are successful like to say, ‘It’s all skill! It was my capabilities!’ And it’s, like, “No, no.”

I was lucky to have been born in the Stanford Hospital, to have gone to Stanford, to know about the network, to participate in it, to make some great friends and connections that kind of helped me along with it. All of that stuff is hugely serendipitous.

On the other hand, you also try to think and act strategic as you could, you try to learn constantly, you work hundred-hour weeks, are constantly kind of trading lessons and information with each other in order to make it happen.

So the short answer is, it’s both – massively luck and massively hard work. Sometimes it’s more luck than hard work, and sometimes it’s more hard work than luck. But every success requires both.

Listen to the full episode »


Ellevest founder and CEO Sallie Krawcheck defines success through the impact her work has on others.

Hollis Johnson/Business InsiderKrawcheck is the CEO and cofounder of Ellevest, a digital financial adviser for women.

Sallie Krawcheck: It’s impact. I thought about this a lot. After I left Bank of America I spent better part of a year trying to decide what was important to me. Success is impact. I could have gone back to a big company. I could have had a much bigger office. I could’ve been more comfortable on a day-to-day basis.

The great thing about what’s going on in business today is you can have an impact, maybe even a greater impact at a small company, whereas historically it had to be at a big company. If you have a great idea, you can get it out there for free. For free. You head to Twitter, head over to Facebook. It doesn’t necessarily have to go viral. By being out there with that idea consistently, and if it’s a good one, people will listen to it, gravitate towards it, and there are many more press outlets as well so that you can find places that are interested in something that may not have been as interesting for a broad audience.

Combine that with being at a startup, you can move so much more quickly, so much more quickly than a big company, all of a sudden I can make the argument you can have a greater impact on people’s behaviour from a startup than you can from one of the big guys.

Listen to the full episode »


‘Million Dollar Listing’ star and real-estate mogul Ryan Serhant stays on track to success by setting goals.

Hollis Johnson/Business InsiderRyan Serhant stars in Bravo’s reality TV show ‘Million Dollar Listing’ and is the head of his own real-estate company, The Serhant Team.

Ryan Serhant: Now, I define success by hitting goals that I set for myself, and it’s not about money. It’s not about lifestyle, it’s not about building a bigger team, or anything. It’s that I set goals for myself, and I write them down every year, and if I hit those goals, I have been successful that year. If I don’t hit those goals, then I have failed that year. That way, success isn’t this big lofty thing that’s up there in the clouds, and it’s not just like, I want to be a billionaire. Like, that’s stupid, right. There’s no plan of action that’s set there.

There’s nothing that drives me crazier than someone who comes to me, says, ‘Yo, I’m an entrepreneur, this is what I do, this is what I sell, I sell this, I do this, I’m building this company’. I’m like, OK, what did you do last week? They’re like, ‘Well, I was in the Hamptons last week, played golf on Sunday, but like Monday through Friday … ‘ No, no, no. If you want to build your own business, you do it seven days a week. I did not take a single day off for three years. And it’s easy for me to say now, but really, really hard to do, and it’s really hard for a lot of people to do, as well. So, you have to figure out what you really, really want, and stick to it.

The other thing I would say is, you don’t have to do it by yourself when you start. That’s probably a mistake that I made. I think I would have grown faster, but I started by myself because I didn’t have that stick to intuitiveness to real estate. I didn’t really know that that’s what I wanted to do, it was kind of weird. I didn’t see myself as being a real estate broker. I didn’t even like real-estate brokers.

And so, I was doing other things at the same time. If I had maybe worked on someone else’s team, if I had maybe worked for another company, if I had maybe learned by watching successful people do what they do instead of just trying by myself to do it, it would have been better.

Listen to the full episode »


Retired SEAL Jocko Willink says success should mean something different to everyone.

Sarah Jacobs/Business InsiderJocko Willink is an author, podcast host, and retired Navy SEAL commander.

Jocko Willink: I don’t think any person can define success because I think it all depends on what you want individually. How do you feel in the morning when you wake up? Do you feel like you’re on the right path? Or do you feel like you’re off the path? Do you feel like you’re on the slippery slope? And you know what you should do every day. Do you do them? If you’re doing them, then you’re being successful. And if you’re doing them daily and you continue down that path, you’ll end up with that success, whatever that definition of success is that you envision.

It’s what I do every day. It’s working hard. I have five-year goals and 10-year goals. But I’ll tell you this: They are also very, very flexible goals, because two years ago I didn’t have a podcast. Three years ago I didn’t have a book. We’ve only just merged with Origin, the jiu-jitsu company, and started making our own supplements. That’s all within the last six months, and it’s been going crazy. So all the irons I have in the fire, and I’ve got a lot of them in there, I don’t know which one I’m going to pull out and ignite and what it’s going to do when it ignites. So, just like being in combat, my mind is open. I’m not sticking; I’m not hanging on to one plan. I’m not hanging on to a five-year plan.

I’ll tell you broadly what I want to do. What I broadly want to do? Hey, I want a bunch of money. I want to be able to do whatever I want. I mean, that’s kind of normal, right? I want to be able to take care of my family. That’s great. I want to be able to take care of my friends. That’s awesome. Those are clear, real simple, obvious goals that I think many people have. Now, you can say that, “Well, my goal is to be happy.” Well, that’s cool. I want to be happy too. The things that make me happy are the things that I do every day, are being on the path every day. That brings me happiness.

Listen to the full episode »


Business coach Marie Forleo says success isn’t about vanity metrics.

Hollis Johnson/Business InsiderMarie Forleo is a business coach, web TV host, and motivational speaker.

Marie Forleo: I love echoing Maya Angelou’s sentiment on this: It’s liking who you are, liking what you do, and liking how you do it. And I feel like I can check all those boxes. I really do like myself, and there are always things that I need to work on. There are always weaknesses. There are always areas that I’m like, “OK. Great. I’m excited to get stronger there.” But I like who I am as a person. I love how we do business. There’s nothing that I would be ashamed of people knowing. I love our team. I love everything we do. So there’s so much joy and fun in that.

Setting goals is exciting, and growth goals are exciting, just so we have a place to go, but we were talking about this on the team the other day, we just don’t like vanity metrics. I don’t give a s—. Do you know what I mean? If someone has a gajillion followers, like, “Oh, they’re doing better than you.” I don’t know how you’re measuring that, but are you happy? Are you healthy?

Do I put my head on the pillow at night and feel like I really did great work today and I’m exhausted in all the right ways because I just squeezed every drop of my gifts out in a way that was fun, that touched other people, and that I feel like, “Dammit, I really did it today.” And I feel like that most of the time.

Listen to the full episode »


Media mogul Tina Brown says success is about creating something with staying power.

Sarah Jacobs/Business InsiderTina Brown has worked as an editor for numerous magazines, including Vanity Fair, The New Yorker, and The Daily Beast.

Tina Brown: We laid down good bones. What can I say? We really did. I think a magazine’s DNA, once you put that imprint in, it can be reproduced with succeeding generations. That’s the goal, that you leave behind a staff and a structure and people who can continue it. Otherwise, you haven’t really been successful if it disappears after you go, right? A lot of the people I have, most of them actually, for a long time, have stayed. In fact, the people that I had at Vanity Fair who only just departed. At The New Yorker, they’re all still there.

I think the way I define success is that we build something that has such an identity, such a powerful pedigree of talent that it’s going to survive long after you go. The pedigree of hiring is something I think about a lot, which is that if you hire great people, they hire great people. It goes on as a kind of reproducing DNA of talent. If you can keep that up, it’s going to have a very long life. It’s really when that gets shot out from under for various reasons, if it’s a takeover or a some kind of financial debacle, whatever, that those bones get trampled. If they don’t, then you’re going to be OK.

Listen to the full episode »


OkCupid founder Sam Yagan measures his success by how much his work matters to his customers.

Hollis Johnson/Business InsiderSam Yagan is the serial entrepreneur behind OkCupid and SparkNotes.

Sam Yagan: If I had to summarize it in a word I would say “mattering.” I want to matter. And that has a lot of lenses. But when I die – whether it’s individuals or whether it’s consumers – I want people to say, people’s lives are better because I was on this earth. And so it could be people who work for ShopRunner. I want to build this great culture where people develop and people get to be themselves and get to be happy and I want to help these retailers succeed and grow.

I was at a dinner last night, and somebody said she met her husband on OkCupid and gave me a hug and took a selfie. And I was like, “Oh, my gosh.” She was so happy, right? I always talk about permanence in the companies I’ve built. The fact that SparkNotes still exists today, 19 years after we built it, I have so much pride in that. OkCupid is still something that millions of people use every day. I have so much pride in that. And my kids are just now getting old enough to start using SparkNotes, then ultimately, probably OkCupid or whatever. And the fact that I’ve had that impact and I can actually see that happen, I think that’s success. It’s like, did you matter to, first of all, most importantly, the people near you: your friends, your family? But then your employees and your coworkers and then people at large.

Because I was fortunate to have some amount of success early in in life, I realised it wasn’t about chasing personal accomplishment. I think early in life you’re just in an environment where, it’s your personal accomplishment that is success. And I think maybe once I got to a certain amount of success I was like, “OK, well, I don’t have to go get more success.” Am I going to spend the next 50 years of my life just running bigger businesses and making more money? That didn’t seem fulfilling. And so then I said, “Well, what do I really value about what I’m building?” And it’s the impact that I’m having on other people. And so I’ve used the word “matter,” as that all-encompassing term.

Listen to the full episode »

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