Leap Academy with Ilana Golan - The Dark Truth About Venture Capital: Confessions of a Unicorn Founder | Ra'anan Cohen | E155

Episode Date: April 23, 2026

Ra’anan Cohen walked into the tech world with no fancy degree and no startup pedigree; just a phone call from a friend and the promise of free food and a gym membership. From day one, he felt like an outsider, constantly battling imposter syndrome. Yet, he stuck with it, learned the ropes of the startup world, and ultimately founded a billion-dollar company. In this episode, Ra’anan joins Ilana to share his wild 15-year ride: a public company on NASDAQ, a unicorn valued at $1 billion, and a board that tried to fire him at his peak. He reveals everything the startup world doesn't want you to know about the real cost of chasing unicorns. Ra’anan Cohen is a serial entrepreneur, author, and the co-founder of Bringg, a SaaS delivery management platform that achieved unicorn status with a $1 billion valuation. He was also the founder and CEO of MobileMax, which went public on NASDAQ. In this episode, Ilana and Ra’anan will discuss: (00:00) Introduction  (04:30) The Biggest False Beliefs On Entrepreneurship (06:38) The Impact of Imposter Syndrome on Ra'anan's Career (09:16) Quitting a Stable Job to Start a Company (12:09) Raising Capital with No Credentials (15:34) The $10M Mistake That Cost Him Everything (18:55) How a Pizza Night Sparked a Billion-Dollar Idea (24:35) Raising Capital the Second Time: The Stealth Mode Strategy (28:47) Different Types of Modern Investors (32:52) Why Startups Are Marathons, Not Rollercoasters (43:43) When to Make Life-Changing Decisions (and When Not To) (45:39) Redefining Success: The Multi-Bucket Life Philosophy (53:36) Q&A: Handling Rejection Without Losing Your Spark Ra’anan Cohen is a serial entrepreneur, author, and the co-founder of Bringg, a SaaS delivery management platform that achieved unicorn status with a $1 billion valuation. He was the founder and CEO of MobileMax, where he led the company to multimillion-dollar international sales and an IPO. Ra'anan is also the author of Confessions of a Unicorn Founder, a national bestseller in Israel, which is currently being adapted into a TV series. Connect with Ra’anan: Ra’anan’s Website: https://www.raanancohen.com  Ra’anan’s LinkedIn: linkedin.com/in/raananc  Resources Mentioned: Ra’anan’s Book, Confessions of a Unicorn Founder: Obsession, Greed, and the Brutal Truth Behind Chasing the Startup Dream: https://www.raanancohen.com⁠  Leap Academy: Ready to make the LEAP in your career? There is a NEW WAY for professionals to fast-track their careers and leap to bigger opportunities.  Check out our free training today at https://bit.ly/leap--free-training

After receiving an investment offer at the $1 billion, I came back to a board meeting. And suddenly, one of the directors stood up, took out a piece of paper and said, I'm calling a vote of summoning the CEO to a pre-dismissal hearing. A startup is more like a marathon. Because 90 to 95% of the time, I'm in crisis mode, depression mode. This is the reality. And this is what we sign up for. Just like when we go running, we sweat,

Same is in this journey. Ranan Cohen, serial entrepreneurs, started and was CEO of two starters. One had an IPO. One was a unicorn. Now, in this fascinating book, Confession of a Unicorn Fowder, he literally pulls back the curtain on their darker side of entrepreneurship. Entrepreneurs and managers, usually there are people who are used to success. And suddenly, when you go on this journey, you start to receive nose, you start to get ghosted

from investors. and this is a shock. And what I like to say, you know, if you're going on this journey, it's okay, this is the game. How do you cope with rejections and challenges and hard moments? Never take strategic actions

when you're suffering. Move on, finish this pain part, and then make the decision. Now you're living a great life, but if you know where that next 15 years have been, would you still jump to entrepreneurship? It comes with a lot of pain. The problem is startups.

Welcome to the Leap Academy with Ilana Golan Show. I'm so glad you're here. In the Leap Academy podcast, I get to speak to the biggest leaders of our time about their career, how they got where they are today, the challenges, the failures, and countless lessons.

So lean in. This episode is going to be amazing. I'm in a mission to help millions reinvent their career and leap into their full potential, land their dream roles, fast track to leadership, jump to entrepreneurship or build portfolio careers. This is what we do in our Leap Academy programs for individuals and teams.

And with this podcast, we can give this career blueprint for free to tens of millions. So please help my mission by sharing this with every single person you know because this show has the power to change countless of lives. Deal? Okay, so let's dive in. Okay, so here is a story for you. I always make a point to check if a podcast guest has a book. And if they do, I listen to a few chapters as part of the prep, right?

So a few weeks ago, I'm going hiking on the weekend and I start listening to this book from my next guest. The name of the book, Confession of a Unicorn Founder. Now, listen to this. I had so many things I needed to do and listen to that day, but I just couldn't stop listening to this. And it all resonated so, so much. by far one of the best books I read in a long, long, long time.

And it just takes you on this emotional journey that you will not forget. Ranan Cohen, serial entrepreneurs, started and was CEO of two starters. One had an IPO. One was a unicorn. Now, in this fascinating book, Confession of a Unicorn Fowder, he literally pulls back the curtain on their darker side of entrepreneurship, on startups, and the venture world. Listen, I am warning you, you will not want to put.

the book down. And you will have to listen all the way to the entire episode. So get ready to see the world of entrepreneurship in a completely different way. Also remember, at the end of the conversation, I choose a question you wrote on our YouTube channel. So today, inspired by this conversation, we'll answer a question about dealing with rejections in the hard moments. So let's go. Ranan, so good to see you on the Leaf Academy show. Great to be here. Oh, this is going to be so fun. Plus, we share a birthday. What are the odds? So cool. January 25th, do you remember? Yeah. January 25th? Let's go. So happy birthday to you. Sort of.

The first person in the one that I know that was born on the same day I was. So yeah, it's a first for me. So I do want to start a little bit from actually the end. Why write such a book? And what are like some of the biggest. false beliefs maybe that you wanted to break was this kind of a book? After my, almost 15 years of a CEO and founder of startups, after the second one, is a pretty sudden exit without any spoilers. I didn't have any retention or any time that usually happens after a founder's exit. So I took it as a project and went to Bali for one month to brainstorm what I'm going to do, with the other half of my life.

And at the top of the list was, I want to write the story. I want to write my experience. I remember myself coming into this world of startups, entrepreneurship. I had a totally different perception. We are living today in the startup world. And I think in general,

in the culture of fake it till you make it, which is great, manifestation and everything, I believe in it. But the other side, the flip coin of this, is that coming into the world, you can get a real shock by starting to feel how it really is, and I felt a strong passion to write about it. Initially, I planned to write it for myself, friends, for colleagues, and just give it away. It wasn't planned to be a commercial book. It contains sensitive stuff

about the tech ecosystem and then some venture capitalist and others. Obviously, I changed names, but it was also a story how it rolled out into a publisher, the leading publisher in Israel, and it was released just over a year ago. And surprisingly, for me, it became like a national bestseller, and now it's going international. And now I'm also working with a production film and doing a TV series,

so it opened a new life for me. And I get feedback on daily basis from entrepreneurs, founders, or people who are curious about this world, and it's super exciting for me. Oh, this is so fun. So I'm not the only groupie here that loved the book.

But let's take you back in time then, tell them a little bit of the stories. So first of all, you do talk about having imposter syndrome where you got into tech. Take us back in time a little bit to those early days. I didn't come out of any flashy tech military unit,

8200 or others. I was a combat soldier and officer. And after that, I worked for the prime minister office. And then I found myself studying accounting. four years of boredom, soul-crushing grind. And as I was about to turn 30 years old and start my internship at KPMG,

just like all the big things in my life by chance, I received a phone call from a friend who asked me, hey, bro, you want to work in a startup? And I said, what are you talking about? So he said, yeah, listen, you traveled around the world. We're looking for someone who knows other cultures and you've been an officer. and we need a project manager.

Someone to communicate between the local engineers and the international customers, you get free food and a gym membership. And I said, I'm in. So I called my parents and said, hey, mom, there's not going to be a CPA in the family. I started a junior role at a startup. It was back early 2000 in the mobile space.

The mobile industry was exploding back then and there were dozens, even hundreds of startups. and this was one of the hottest startups in the Israeli tech system. I was very fortunate to fall on this startup by chance that has an amazing founding team, founders, and they were not only very highly talented, but they were also great humans. From day one, I had an imposter syndrome. I remember coming into the startup. I was introduced to my team manager.

She was 24, super talented. And I said to myself, okay, in this lifetime, I probably missed it. I played around with other stuff and I'm coming in too late to the game. But they were super kind and I learned everything on the job. In retrospect,

all the seeds that flourished later on were planted being in this amazing startup. So the imposter syndrome followed me from day one. I felt that any minute someone would knock on my door and say, hey, man, you're cool, but you don't really fit in. And this together with some idea that I have about roaming phone calls.

It was some kind of vague ideas. The two forces came together, and at the age of 34, I resigned my role and told my CEO, hey, I'm going to build my own startup. And take me there for a second, Rana, because at this point, you're not the typical kids selling lemonade. So why a startup of your own?

That is a really scary thing. Was it scary for you, where you're just mainly excited. Where was that? Now with a reflection, I must admit that people ask me, how did you have the courage? Back then I was already married.

Our twin girls were like two years old and the mortgage, you know, the entire deal. And people ask me, where did you have the courage to live a great job with a nice salary? And to be frank, I didn't have the courage. I had a brother of courage. Sometimes you can bring the brother in.

And this brother was, I have nothing to lose. I mean, I was sure that it's just a matter of time, very short time, until my bluff is called. And so I have nothing to lose. So when you have nothing to lose, you can already go for it. So until today, I play with the thought. What would have happened if I would have felt secure and thriving in my job? I'm not sure I would have made the jump. By the way, today when I mentor entrepreneurs and I lecture and I tell them about this,

that sometimes there is like a misconception. that the founder, you know, when he's on the start line, he's like Superman, I'm going to conquer the world, I know what I'm doing, I have it all figured out, let's go and do it. I tell them, no, you know, this is not how it works. We go to the start line and there are many black holes, butterflies in our stomachs, so many questions, and we jump into the water in spite of all these, and you never get them all figured out and everything in line.

And let me ask you for a second on, before we continue with this story, now in retrospect, and again, now you're living a great life. But if you know where that next 15 years have been, would you still jump to entrepreneurship? Because I think sometimes we also jump because we're ignorant.

I can say that for me, my ego running some pretty good organizations, like I felt like, oh, I got this. This is going to be a piece of cake. And it wasn't. So would you in retrospect jump or no? I wish I would because there's something beautiful in my eyes, in naiveness or the ignorance of at least the first time founder.

You don't really grasp the journey you're taking on yourself. You're not really aware of all the pain and suffering. It's really helpful, almost mandatory in order to make this step. Because like for my kids, someone asked me, Did you wish your kids will be founders, entrepreneurs? I said, frankly, no. The only thing I wish for them is to be happy. But if I would have recommended of going into a direction,

it comes with a lot of pain, and it's great that I didn't know about it. So take us the first time that you're trying to raise capital. You always talk about selling the dreams. And it's true. Like in entrepreneurship, you constantly need to sell the dreams to everyone and including yourself. That's what motivates you.

So talk to us a little bit about that, just starting with your company, Mobile Macs. So as a startup founder, I mean, the first thing is raising capital. And also, I was very fortunate. Again, this relates to the thing we just talked about, that I had no clue that I have zero chance of raising money. I mean, back then, the ecosystem wasn't that sophisticated. They were like VCs and the founders, but there wasn't all the ecosystem support and

coming without tech education, without a fancy military unit, without any medal to show raising money from VCs, your chances are almost zero. I didn't know that back then. VCs, venture capitalists, they like to invest in serial entrepreneurs, IPO, unicorns, or in someone

that the entire industry is chasing and all the rest need to find a way to squeeze out some pennies. But I had a lucky break. My lucky break was that two VPs from the startup that I worked in, the CFO and the CMO, David and Israel,

which I didn't work directly with, but they knew me being a small startup of a few dozens of employees. And they approached me and said, hey, Ronan, we heard you're building a startup. We want to be your first checks. We want to invest each $30,000, $40,000. You know, we like you. You're a hard worker. And we want to put in the first money. Now, back then, I didn't realize what a life-changing event that was.

because in addition to the working capital that I could start using, I used this while pitching to other angel investors. Again, this is in retrospect. And when I talked with them after the book was released, they told me, yeah, you didn't have the CV. You didn't have the experience. You didn't have anything. But these guys, they were NASDAQ veterans.

They already been through a successful IPO. And the fact they put in money. And together with the fact that they worked with you for three years, so they know you pretty well, This gave us the comfort to put the money, and I raised a million dollars, and suddenly I have a company, MobileMax. Terrible name, right? But that's what I had available back then with Mobile. Mobile Max, software platform for telecom carriers. You know, in startups, just like in surfing, sometimes it's not just about how good of a surfer you are. It's about what day did you catch and what day did you go into the water?

and we're like mid-2000 and all the stars aligned. The mobile industry was booming and the multiple devices, a jungle of devices, Nokia, BlackBerry, Samsung, LG and what turned out that our platform that had the capability

of enabling, developing once and deploying it on multiple devices, back then the devices were not compatible. So it was a nightmare for development of applications. So this, capability that we had was gold for the telecom carriers and it was gold for the developers. And we started signing up telecom carriers all around the world, AT&T, Verizon, Telefonica, Vodafone. It was just one after the other. All the stars aligned and it was exploding. And you go public, which is

incredible. Yeah. So less than three years after founding the company, underwriters came knocking on my door saying, hey, we've been following mobile Macs. You're perfect for an IPO. And we went public. And suddenly, you know, zooming out a bit, the run and the guy who sneaked into the tech industry, just trying to hold on to my job and building a startup because I had nothing else to do. And suddenly I'm a CEO of a public company.

I'm on the press. I'm talking to analysts. I'm on stages. This is wild. I was in like my early 30s. So the things like that that happens when you manage to conquer one dream after the other, this is amazing.

It builds what I believe is the most important muscle in our body, which is the muscle to believe that you can do anything. Now, this has also a dog died, this muscle. This muscle says, okay, I'm unstoppable. No one can stop me. I know better than everyone, at least for me at my early 30s. I became a little cocky, I had the sports car, and you know, you feel like a rock star.

It's crazy. So luckily, I don't think it had effect on my personal life and personal interactions, but on the business, just after we went public a few months later, they were one of the institutional investors called me and said, Hi, Ranan, we have our investments manager on the line. We want to buy from you shares at $10 million. This is only a part of your shares. Now, this is 2007.

Back then, $10 million were a lot of money. Even today, $10 million is a lot of money. especially for a young guy with a kids and mortgage and family. And I found myself telling them, hey, I appreciate the offer, but the company is just at $100 million now. We're still growing. We're going to be billions. Selling now would be losing money.

I gave this speech and they said, okay, are you done? We're familiar with the CEO's speech, whatever. It's very emotional, but we all know how it ends. Say I do. And the money is wired to your bank. That's the beauty of a public company, no negotiations. You just get the money and celebrate. Now, back then, today I want to believe that I'm not that triggered and that I would

respond differently. But back then, what I heard is that, you know, you're just playing us. You don't have the balls not to sell. You're going to sell. And when I heard someone thinking like that, I was just more lock. and I'm telling them, listen, you're wasting your time. We're not going to talk about it before it hits a billion. And that's how the call ended.

And they tried to insist, they called our accountants, EY and our lawyers, and to convince me, and I was, the more calls, I was more locked in. And this passed, and a few months later, the Black Swan of the mobile world, iPhone, was launched and started to gain traction. And then came his brother, Android. and suddenly an entire industry that was multiple devices, jungle, basically our entire value proposition, it took a few years, but it became worthless.

So that was the implication of my smart decision not to sell. We need to pause for a super brief break, and while we do, take a moment and share this episode with every single person who may be inspired by this because this information can truly change your life and theirs. Now, I want to check in with you. Yes, you. Are you driven, but maybe feeling stuck in your career or a fraction of who you know you could be?

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and you didn't take the money. And even though to some extent it looks like you did, an IPO and you're probably a millionaire because that's how we look at people. Now you're trying to figure out how on earth am I doing the everyday work because I don't even have a job, right? Like I need to just maintain myself. Take me through that and you talk about it in such a beautiful way in the book, but take us a little bit that time between the two startups. What was it like for you and for your family, honestly? So I'm already like 40 years old. We have four kids still mortgage, the entire package.

Mobile Macs was an eight-year adventure. Lots of fun, lots of experience, nice, cool t-shirts, but not a cent in my bank out of this journey. So this obviously has implications because going into the startup game, we know the statistics. We know the statistics are against us as founders,

and most of them don't make it, and it's okay. For me, there was another level to this. I managed to step on the podium. When you do an IPO, you're on the podium. There's the prize. The investors can sell. You can take the money.

And instead of doing that, I placed all the money back on the roulette table and gambled like my family's financials future. So there's a lot of conscience. So this was a period, a very, very complicated period for me, sleepless nights with Ravit, my wife. So I kind of like toned it down. I said, you know, no, don't worry. I'm going to build another one.

Don't worry about it. I had no idea what I was going to do. I just tried to come up with ideas, crazy things like dating apps for 70-year-olds, diet over gambling, any idea I could think of. And the problem is with startups, I talk about when I meet people outside the industry, if you're an entrepreneur in, like, say, normal industries, if you are in real estate and you build buildings. So you did one, you have the playbook, and now you're going to do another one. obviously there's uncertainties and their surprises,

but there is a playbook and eventually this project you've been to put in a few years and something is going to turn out. There is a route to the medal. In the startup world, you're aiming for a moving target and there's so many moving parameters, the technology, the industry, the customers. So the chances, the fact you did it, okay, you get a lot of experience, but winning the lottery again is a totally different game.

And that's how I felt. I felt like, okay, I blew up my lucky chance. And now I'm just trying stuff that doesn't work. And it took a while. It took like almost a year of trying and obviously economic implications on the family, issues with the partner. You don't see the light at the end of the tunnel. And back then, it seemed like almost hopeless.

Until, again, by chance, one night, so every Friday night, like we have a pizza night. One night, the pizza was late again. with four young kids and a wife, a late pizza can be drama, even big drama. And this was a night of big drama. I said, okay, I must look into this.

Now, we were talking like just over 10 years ago, 2013. So we had Amazon Prime taking off. We had Uber. There were like advanced services, but not as it's popular today. E-commerce was like 5% of retail. Today it's over 20%. It was getting,

out of traction and what hit me is I said, okay, when I order a pizza, why can't I have the same experience when I order an Uber or Amazon? Why can't I see it and communicate with it and everything could be smoothly? And then looking into it, the answer floated pretty fast that when ordering pizza or a package or a technician, all these companies, they're not tech companies. And unlike Amazon or Uber or the new guys, they don't have the capabilities to develop these advanced. advanced delivery and logistics functions, and this planted the idea that if I could develop a software platform that would enable these old school, the Fortune 1000, the old guys, the same capabilities that Amazon and Uber developed for themselves, this would be great.

There was one main problem. I'm not a techie guy. I don't know how to develop it, and I don't know if you can develop it and how to approach it. but I love sports and I love marathons. And in one of the marathons, I met Leor, Leone. He was back then the CTO of Get Taxi, Get Taxi, Israel's Uber. So it's like the number one candidate to talk with him about this.

We were just like Facebook friends and I DM'd him and said, hey, let's have coffee. And from the first minute, this idea sparked and we understood that what these companies developed internally, this would be a mandatory requirement for anyone who they did. delivers. And we got together and founded Bring. So Bring is a SaaS software service company that enables companies that have deliveries, these advanced logistics capabilities of optimization and customer facing, et cetera. And the company from day one exploded. I mean, we signed up customers all around the world, huge brands like Walmart, McDonald's, the pizza hat all around the world, 50 countries.

But before that, before it explodes, you talk a little bit about also raising capital. And even though it's like a second time, et cetera, it was still hard. So can you take us there for a second? Because I think there's also a myth that if, like you said, if you've done it once, it's going to be so easy on the second time. But it's not necessarily.

You're going to have your own ups and downs, even though it's a second time. Yeah, raising money in general, you know, it's not, it's tough. So this time I came to it in a strategic manner and I remember my previous times and I said, okay, this time I want to come like a rock star. So what does that mean?

So I defined a checklist of what would be rock star status for a startup like mine, meaning we have design partners, we have customers, we have Web 360, all the parameters that if I would face an investment, investor, it would stand out. I mean, VCs see like 1,500 startups a year, they invest in five. This will be one of the top five. Together with Leo, we defined what we need in order to accomplish this rock star window. And we worked back from that. For nine months, we were in stealth mode. We didn't approach any investor. And with VCs and investors, you know, today I'm also an investor,

we always like to say as investors, you know, you can come even early on when you're not ready, because we always want the foot in the door. We want the option. We want to know what's going on. This is like a small trap because they said you only have one chance to make a first impression. And there's like the next door's neighbor's son syndrome.

So if you come in too early, they label you and today everything is in the CRM and you're labeled, you can turn it around, but it's pretty tough. So it's better. And this is how it works for us. For nine months, we were still small, didn't talk to investors.

Once we felt we were strong and raised, We came out and again in one month we received like investment proposals from the top VC, Sokoya Blumberg and others. So it was a totally different strategy. We were also as the founding team, two founders, one experienced after IPO, the other one like national tech leader. So the team was also set in place. By the way, initially I was very concerned about, you know, the way Mobile Max ended after eight years. it crashed to zero. So I was concerned and what I found and learned, and today it looks pretty straightforward to me, that this journey was perceived as a very strong unique capability.

So the fact that the technology changed, you know, iPhone and Android came in, the entire industry shifted, these things happen. And I'm mentioning this because today I talk to a lot of entrepreneurs that want to go to a second time and they are very concerned about the outcome of their first journey. This was a very, very surprisingly good lesson to understand coming after a first round. If you did the journey, you built a team, you scaled it, you raised the money, this is super valuable.

So we went out and started funding, and from there it's exploded. And again, the stars aligned beautifully because Amazon was killing it. And initially we had very nice decks and presentations explaining why fast delivery and efficient delivery is super important. And all our customers said, hey, we don't need to see these decks.

We know this better than you do. Amazon is killing us. Show us what you can do for us and let's stock business. So this was a dream come true. And we scaled the company, signed up customers and raised like $200 million. Every three months, we had an inbound round doubling or tripling the valuation. It was like crazy, crazy. And this time I learned, not every time I learned from my mistakes.

But this time I learned, and from a certain point, every investment round, I sold some shares. My co-founder Lior also sold some shares. Also, our employees, I insisted that employees will still some options. And the more funding we got, the more shares we sold. But somehow the investors didn't like that. Yes. Yes. So investors in this context, you can define them in two types.

ones who believe that it's great that founders and employees will stay with the backs against the wall, no dollar in the bank, they will be hungry. If they will cash some money, it will reduce their motivation. There are some that believe like that. There are others that believe on the other side that if you along the journey, and again, assuming this is a successful journey, it's not the company is collapsing and you're running away, the journey is successful. The journey is successful and you managed to get some money along the way, this is good for everyone because this will increase your dreams. This is the capitalistic lifestyle that we're living today, this hedonic treadmill that we're running on for good or for bad. I'm running on this

treadmill. There's always something that I crave for and I almost swear to the universe, just get me this. I just want this, this promotion, this money, this whatever. And I swear I will never ask for anything again. And then we get it. The carrot moves again. Of course. Yeah. If you dream of closing your mortgage, then you'll dream of your house and you get the house. You want houses for the kids.

And then you want planes. It never ends. So the modern investors understand that. And they also, they even encourage founders and employees to cash along the way. In my journey, I had the other types, the old schools, and they didn't like it. And they told me they didn't like it. They didn't like me selling shares. But the eight years car was still.

stinging my back. You're like, I'm not doing this mistake again. Yes, I used to tell them, listen, I understand you're not comfortable with this, but I have a family. I have a wife. My priorities are different. And eventually this led to the first page of my book where I came back from after closing our biggest deal ever,

like a $40 million deal. After receiving an investment offer at the $1 billion, I came back to a board meeting. I landed to a board meeting. I had champagne set up. And I was sure, you know, there's nothing like a big win to clean the air in the locker room. I was sure, okay, this will clean everything, all the nonsense that we fought about. And I'm going to get medals.

And I was walking into this board meeting and sharing the news of our big deal and our big investment. And suddenly, in the middle of my presentation, one of the directors, stood up, took out a piece of paper, and said, I'm calling to vote of summoning the CEO to a pre-dismissal hearing. And that's how the book starts. So apparently they really didn't like all the share selling. In retrospect, I don't think it was about selling the shares. It was more, I think, about ego.

So investors, VCs, many of them don't really like when a young founder, they tell him, do this and he does otherwise. And then he does it again and again and again. So it's not really about the cash out. I think it was more about ego. And then World War III, half of the book is about that between the VCs. And then 2021, when the company hit the unicorn, the billion dollar valuation, I sold my shares, retired and wrote the book.

And surprisingly since then, almost on a weekly basis, I get messages from readers telling me, hey, you wrote our story. We had similar stuff. Usually these stories end with an NDA and the founder on his knees and needing to go back to the industry so he doesn't come out. So I get a lot of these. So now I'm in my third startup, the book, the TV series, the lecturing. It's a new life for me.

I've been in some of the startup ecosystem and some of these meetings and meetups and everybody is feeling like a superstar and there's this whole fake it till you make it. And then on the other hand, we toss and turn in the middle of the night and nobody wants to admit it, right? How does that play that consistent? This is where I need to fake it, but on the other hand, I can barely breathe

and everything is collapsing under me or in both of the companies, like when it actually happened. So this was one of the main, I think, triggers that pushed me to write the story because, you know, today in the startup world, and I think in general, we're living in this fake it till you make it culture, because, you know, you need to manifest success,

to create success. It's a great attitude, but again, this comes with a cost. So I remember myself during this year, after Mobile Max, before Bring, I used to go to investors, meetups, and startup events. And I remember, you know,

just before stepping in the door, I used to take a deep breath and meditate to put in a million-dollar smile. Because I was the guy everyone was pointing at saying, hey, he just did millions after an IPO, and now he's doing another round for fun. And, you know, you walk in the events, and for those who are not familiar,

you know, there are like baristas and bartenders. And the worlds that are flying in the air are like fabulous, killing it, exciting. And everyone seems so successful. And there's also in the media and in the social media, there's this very strong winners bias, right? Every day we see

this one did an IPO, this one sold in another round. We don't see the other 99 or 999. So I like to use the analogy of sports and running marathons or ultra-maritons.

So when you're running for a marathon, training for a marathon, there's a famous phenomenon called the wall. After three hours, it's like your body has no glick again and you feel like you can't go on.

Some of us, it happened before the three hours. I'm just saying. It can happen much earlier, yes. And everyone that trains for it knows about it. And I remember myself in my first marathon, in Miami Marathon, I hit the wall. It was crazy. It's like you feel you can't move on. And I remember after one second, I said, hey, here it is, the famous wall.

And I kind of even smiled to myself, hey, okay, I'm facing it. this is what I signed up for. And then I recall that everyone tells you, okay, you just need to carry on. Even if you slow down a bit, just continue and it will pass. And you continue, you go on, and life goes back to normal.

And you go in and you head to the finish line. So in the startup life, in the startup journey, no one tells you about these walls. And these walls are multiple walls. So, you know, there's a misconception. People talk about startups,

even myself as a roller coaster, right? but when you think about it, roller coasters, 50% of the time go up, 50% of the time go down, right? This is physics. A startup is more like a marathon. Because 90 to 95% of the time, I'm in crisis mode, depression mode, I'm sure that it's going nowhere,

and maybe there's 5% of smiles and high. And the problem is that if we are not aware of this, I mean, deeply aware of this, this could lead to very problematic, decisions such as I was sure doing this time that one of the two, either that I don't fit this founder character because it looks like everyone is having a great time and everyone is so relaxed and successful and I'm not sleeping at night. So maybe it's not for me. Or that I may be thinking that I'm not on the right path because it shouldn't be like that. This is something

I talk about a lot in universities. This is the reality and this is what we sign up for. Just like when we go running, we sweat and we start sweating. And we know this is how it is with running. Same is in this journey. And the problem is that if in a marathon, you have a training plan, right? For a few months, you train and you increase your mileage. And it's very difficult. But if you stick to the training plan, to the gameplay,

there are high chances that you will reach the finish line and get the medal. The problem with the startup journey is that you never know if there is a finish line on the path you're going. There is no playbook. And when the things are really tough, when you're in misery,

in a marathon, I fantasize about the medal and the finish line and I said, okay, I just need to push through and I'll get it. In startups, you think, I like the sentence,

you know, not all pain is gain. You think, maybe I'm going nowhere. I'm just suffering. But that's so depressing. How do you continue, Rhinan? It's depressing, but this is the game. And, and you know, it's all about, I believe in general life, it's about framing. If I'm facing a hill now and I'm going to run a hill, I know that my quads are going to burn. So when they burn, I said, okay, this is it. And when you're going on this founder's journey and you deeply understand that, your muscles will burn. And I remember at Brink, Brink was my second round.

became more mature. And when we had some, like, tough days, I used to grab Lior and we were going to the office. And I used to smile and say, hey, man, this is so fun. It's like monopoly. Now we are facing this wall that seems unsolvable. And people gave us money to solve it. This is, he used to say, you know,

you need to come down with your meditations. But I think we need to adopt this kind of mindset in order to not only survive, you know, we want to strive because it's a long journey and we need to find our own tactics to go along the way. I use also sports a lot, but I think understanding and realizing that this is the misery I'm going through, it's not a problem I should have avoided. This is the reality that I need to face

and there will be good days and bad days and this is what I signed up for. And everyone is suffering, everyone around, me has the same pain and it's okay. I think this is such an important message, and it's funny because when I need to summarize the entire Leap Academy podcast in one word, it's probably grit and tenacity,

because that's what all the leaders, if you actually listen to everybody like you and some of the biggest leaders, like Tom Bill, you said, don't ask me what's the least I can do, ask what's the maximum you can bear, right? And it's like, it's really more about what can you take on. But you do talk a lot about your crazy runs.

And this is not just marathon. These are like ultra running is like a very different beast than marathons. And I did one Iron Man and never going to happen again. Tell me a little bit, what are some of the things that running taught you or how do you see the similarities? And why on earth to run ultra marathons? Like you did it. Tell me. I used this mantra that there is a quote in the first page of the book, a quote from John Rockefeller, the first billionaire in the world.

He was asked once casually in a conference, how much is enough? His answer was just a little bit more. So this just a little bit more, this is a mantra that I love very much. And it has different meanings, depending on the context. But in running, for example, I'm a late bloomer in everything. My first marathon was at the age of 38. I gave myself a birthday present. It was a disaster.

I barely finished. I barely walked after that. But I signed up for another one immediately after. And a year later, a friend called me and said, hey, there is like this thing called the triathlon. Do you want to do? There is an ironman where you swim and then you bike and you do a marathon in the end.

So I went into that. And then you're in this network of people and someone says, hey, there is an ultramarathon. You know, it's, I was sure that after, you know, a marathon, the world ends after the marathon, right? 26.2, that's it. Suddenly there is a 50-mile race. And I signed up for that. And then, again, people around you talk about, and by the way, this has, I think also it's a great example about the people you surround yourself for good or for bad.

And when you surround yourself with like lunatics and the Saturday night, someone asks you, you know, who's up for a, 40-mile run tomorrow, and it sounds normal. So you started doing that. And 100 miles is like the holy gray of ultramaritons. They're even longer ones than that. I did a few of these. And what I found amazing is that doing these runs, you know, especially in parallel to being a startup, founder, CEO,

it's like meditations. You detach the agony of the body. Takes you to a very, very deep place. It's magic. I rolled into this direction, especially after I sold my sports car. I got rid of it, and I didn't have a car, and I started running to the office. And I found this new cheat system instead of driving running to the office and back. And this became my lifestyle.

So I got free mileage on expense of commute. And this became a part of me. And I remember that in our lives, every morning I used to wake up, this monkey mind and a million things and a million worries. and I put my running shoes on and I used to go out and as the miles go suddenly the water that was very, very

wavy comes down and things are clearer and the problems don't disappear but everything looks less dramatic and it's like it gives me a special pill to carry on for another day so this was like my mental detox and I highly encourage

adopting something. I remember I run along the beach and I used to look at fishermen, you know, sitting there for hours with it. And I didn't get it. Today I get it. It doesn't matter what, but if you have a hobby, you're passionate about that distracts your mind from your daily grind,

this is magic. It's just one step after the other, just a little bit more. And you find yourself doing these long, long runs. Yeah, I have a feeling that some of us will not find themselves doing these very, very long runs. but I think there's also a quote that I love from you that you say something along the line of never make race decisions on an uphill. And I think that was also just such a good one for me because sometimes we're in ruts and everything looks bad. And if we're going to make decisions from that wall or from that uphill or from that really hard moment, that's clearly going to be

a bad decision. Yes, that's totally another side of this mantra of just a little bit more. So I have like a rule with myself that every time I'm facing like a very tough decision with the startup or in life or in the relationship or anything. And I want to quit. I have this rule where I say, you know what? Okay. But let's continue just a little bit more. And in the ultra world, there is this mantra of never make race decisions on an uphill, which practically means never take strategic actions when you're suffering. move on, finish this pain part, and then make the decision.

And like in life, you continue doing this uphill and you finish the hill and suddenly it's not that bad. You can carry on. And it goes along, by the way, with another ultra-marathon meme which says, beware of the chair. Right. So, you know, if you're pain, you're tired, you're burned out. It's okay to take it slower. It's okay. but don't stop.

Because if you stop, you know, you never know what cramps can jump on you and things happen. So it's okay, you know, you can't run a marathon in one sprint. It's okay to slow down, but don't stop. I've done my races. I don't know if I could ever go back to it. But it is incredible. Like my team knows that if I don't go and at least hike or run every single day, I get annoying. I am not myself.

But when you kind of look at yourself and you're kind of in a third phase, if you will, or whatever that is, how did your definition of success change, Renan? Today for me success, I look at it as I have several buckets. It's not only one bucket that I need them to be as full as possible. So there is family, there's financials, there's health, there is meaning. There are a few buckets. and I need all of them to be at an optimum level. Because, you know, let's say if just health is bad, then all the rest are meaningless.

And same with other. If your relationship is bad, then that. So I need all of them to be as high as possible. And it's different than in investments, right? So today, if I invest in five startups and only one of them makes it big time, this is a great success. But for me today, I need all these handful of buckets. in an optimum level.

And today, building a startup is like doing ultramarathons. Today I do marathons. I don't do ultramaritons anymore because ultramaritons like startups. You need to be all in. In a startup, a founder is all in. And people talk about work-life balance. You can close the laptop and you can take vacations. And that's what I used to do.

But I used to play with my kids at the beach. But my head was somewhere else. as a founder of a super intense venture. This is a price that we pay. And if you're a founder, you're all in, just like if you're doing ultramaritons, then you can't surf and ski and yoga

because you're either running or you're recovering. That's the two stages. So today, I think, by the way, there were bets on me that after bring, I would build another one. I wouldn't last three months, six months.

I told them no more. You're having a great time. I can see it. Yes. And I was very fortunate to find at the late stage a new passion, which was writing and the impact and the world that it opened for me. And I think that entrepreneurs, and by the way, when I say entrepreneurs or founders, it doesn't mean you're a startup founder or a business founder. You can be in a founder or entrepreneur state of mind or state of living as a school teacher, as a public employee. In every one of my companies, I had multiple entrepreneurs.

And in my definition, living as an entrepreneur means three things. One is that you're living with passion, right? You're not just coming along. You're with passion. Two, you take 100% accountability. I'm responsible. It's about me. I'm going to make it happen.

And three, you're proactive. In my definition, if you have these three ingredients, you're an entrepreneur. The framework can be start. can be business, can be civil servant, can be in different ways. So in this life of being an entrepreneur and being a passion, it comes again with the fact that you're all in. And I love that because it's true you can't really turn full entrepreneurship off at any given moment.

Like I think it's very, very hard. And I do believe a lot of people, even if there are executives or in a company and corporate, they will start creating more portfolio careers. we kind of talked about. So they will have many side hustles and things that they're doing either for passion or for income or for reputation or for fun or they will have multiple ventures. And I think we're seeing a world where everything is shifting. So everybody will need to have that passion, ownership, proactiveness, all the things that you

talked about. But what is when you look at an entrepreneur and you, I know you mentor a lot of entrepreneurs now, what was probably some of the biggest things that you want them to hear now or maybe some of the people listening to this and they're debating, like, should I jump to something new? How do I decide what's next? Like, what are some of the things that you wish somebody told you? I like to carry the torch that anyone can. And I'm an example to it. I didn't come with the background or the fancy Ivy League. And again, if you would have told me the age of 30 or even 34 before I started my first company that I would be a CEO or a founder, I didn't have it in my books. I wasn't

the kid who sold lemonade at the corner or had any of these, you won't point out. I truly believe that you can build yourself and educate yourself and inspire yourself to a journey that will lead you this way. And today, the possibilities even grew. So I was very fortunate to find myself in a startup where I was inspired by amazing founders. It was truly luck. Today, we can do that not only on the physical level, we can do it also on the digital level. So the feeds that I have on social media, workshops that I go to,

online courses, I can surround podcasts, books, whatever. I can surround myself with a soul-nourishing content that could take me and anyone that is curious, you need to do the work, right? You need to put the time

and they need to put the energy. But if you will do that, you can turn yourself into an entrepreneur, a founder. And I remember myself looking at CEOs and stages or reading books. And I used to tell myself, you know, I can see he has it. This guy has it. I will never be able to do what he does. And later on, when I was on these stages and behind the curtains and then talk to the CEO,

you can see they're all normal people. You can build yourself toward this. You need to put in the work, but today there's endless possibilities to do that. Another thing that I like to wave at is that I'm a very late bloomer in everything, in marathons, in writing books, in starting. My first grown-up job was at 30, right? My first startup was at 34. So you can start at any time.

You can make a change at any time. And again, I was lucky that I made this jump where I felt that I was pushed to it. it. Today it's very tough because these questions, I get these questions on a day basis, you know, I'm not sure. Should I leave my job? Should I try? In many cases, I think we're over-dramaticizing the price of the decision or the cost of the decision. Because, for example, when I worked for this startup and I said, okay, I'm going to found my own. What was the worst that could happen? Let's say it would crash. I wouldn't be able to raise funding. I would need to look for a new job. Okay. It may take me six months a year. It's painful.

but it wouldn't kill me. And on the other hand, the upside is very big. And another thing we need to remember, you would never feel ready. You would never feel ready. These kind of changes and journeys, we need to understand

that we fill the gaps as we go along and we never feel ready. And I think that the last point that I like to emphasize, and especially, you know, entrepreneurs and managers, usually there are people who are used to success.

Success. We're using to get applause in our childhood, at school. We're always the ones who succeed. And suddenly when you go on this journey, you start to receive nose. You start to get ghosted from investors. And this is a shock.

And what I like to say, you know, if you're going on this journey, it will be tough. It will be tough. You know, you will doubt yourself and it will be tough. But it's okay. This is the game.

Everyone goes through it. Just come into this game understanding that this is how it goes. You'll get through it. This is incredible. Let me do one more thing that usually I don't do was guests. But if you have a few minutes, I would love to. So every week we get questions on our YouTube channel. And usually I just answer it.

But I think because you talked about it right now, like I have to get you to answer it. So Trish asked about how do you cope with rejections and challenges and hard moments. and I will add also, how do you also create a little bit of a layer of a thicker skin? So let's answer it together for Trish. I think that's going to be really, really fun. So I'll get you to start Rana.

How do you deal with those rejection, with those hard moments? Because you started, I have to get you to finish this. I turn to my religion. My religion is sports, right? So I like to look at it. You know, when a basketball player goes on cold and he misses a shot, you don't see him catch his head and say, wow, I need to retire. I miss the shot, right?

I think this is a healthy way to look at this stuff because we're doing hard things and we're going on court and we are sometimes trying to make these shots from half court. And when I'm shooting from half court and I miss one after the other, after the other, when we look at basketball, we say it makes sense, it's okay, just keep on shooting. and eventually you'll get the one in. And that's how I look at life and look at these situations. When it's part of the game, I just need to continue and increase my options for luck

and they have this kind of mindset. Because again, the grit part, it's not only about surviving. We want to survive and still have the spark. It's not like surviving like someone who is about to drown in the ocean. We want to survive, but with a smile and with the spark, and understand, I'm going to keep shooting until it will come in, and then I'm going to get the trophy.

Oh, my God. I love your answer, Ranaan. And I will give my answer after we drop. I don't want to take your time. But thank you for making this so fun and inspiring and amazing as I knew it would be. And for everybody, just go get the book. And where can they find you, Ranaan? On social media anywhere.

And ranaancoen.com, the book is on Amazon, audible. and I'm very accessible. I'll be happy to hear from everyone. Go get it. Confession of a Unicorn founder. Trust me, you will not regret it. And I can't wait to actually hear your comments on the show because you will love it.

So thank you so much, Anna. And you are the best. And I can't wait to go running with you sometime in like maybe jogging, doing something. Absolutely. Had a great time. Thanks, Ilana. Okay, I hope you enjoyed this episode as much as I did. This conversation is so, so good. Seriously, that book is wow. But Trish, you asked an incredible question about rejections and challenges. And I wanted to give you a little bit of the way I see this. So again, the hard things about rejections is that you forget all the great things that you've accomplished and you start believing the rejection, the hardship, the things.

that are hard. And what I want to do is give you very practical tools that I use in order to continuously remind myself that I can do this. I can do big things. So that's what we're going to talk about. So first of all, thank you for the great questions. If you have more questions, put it in the comments on our YouTube channel and we're going to look for them and we're going to pick a question and we're going to answer them every week. So the very first thing is to remind yourself that success leaves clues. And all you need to do is remind yourself of those clues. Right. So number one is just write down all the little things that made you successful in life. And it's interesting how, again, when we're down, it's hard to even remember, but I want you to

take a look deep, even as a kid, as a teenager, in college, whatever, like all the little things that made you successful, maybe as a parent, maybe as a kid. Is like, what made you? You know, you successful. And think about all the skills, all the things that you accomplished, all the places where you got awards, all the places where people said, thank you, thank you. So think of all these moments and write them down. The second thing that I want you to then do, and again, take five minutes for each one of these. So turn off notifications. And again, write down everything, all the places where you've been successful, number one. Number two is write down what are you grateful for right now. And what's beautiful is, is like when we're really down, sometimes we can't even

feel that we're grateful for anything. But if we actually force ourselves to look, I mean, I can breathe, I can see, the trees are beautiful, the sky are blue, whatever, right? Like, there's still things that you can be grateful for right now. So try to find the little moments that make you feel grateful and write them down. Again, just take five minutes. Don't take it long. really kind of force yourself to think about the little things that make you grateful, that roof over your head, whatever it is, have food on the table, et cetera. So the little things, but really remind yourself that there's reason to be grateful for whatever you have right now.

Number three, what I wanted to write down is who you'll be in the future. And the way I want you to write it is I am basically a really badass, whatever, like business person and I'm creating. these big things and I'm going to be successful because one, two, three, all of these things. And I want you to write this down. And I want you to remember who you are, the badass person that you are. You've been successful at all these things. You're grateful for all this. And that's what's going to make you successful. And with that state of mind, again, if you do all these three things, it's only going to take you about 15, 20 minutes and you're already going to

feel like the badass person that you're. meant to be. So I hope you're going to win big time, Trish. Let us know how it worked in the comments. All of you, if you heard this and this has helped you or if it didn't help you, let us know in the comments and we're here to support you and can't wait to see you win. Again, share this episode with everybody you know. Click the like, subscribe, download all the buttons because it really, really helps us continue to bring amazing guests and to continue to make this show even better. So lots of love to all of you and let's go crush the day. Bye, everybody. Remember this episode. It's not just for you and me. You never know whose life you're meant to

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