LeapCon 2025: Ilana Golan on Taking Bold Risks That Lead to Unstoppable Career Growth

Well, I am so excited about the show today, and I'm sure you're gonna have an amazing time listening, but I have a favor to ask. See, I'm in a mission to help millions leap their careers, elevate their careers, land their dream rules, fast-track to leadership, jump to a demurorship, create portfolio careers, and this podcast is about giving you the map of how some of the biggest leaders of our time reach success.
So subscribe, download, so miss it. Plus, it really, really helps us continue to bring amazing guests your way.
So let's dive in. I'm alive.
Everything is cool. I have two kids.
Things are cool. But something was wrong.
I could not dream. And it drove me nuts.
So I moved from engineering to technical sales to product, but what I realized is every time I get good at something, I get stuck. So when a friend of mine, somebody I knew for probably two decades, wanted to start a company together, I was like, oh my God, yes, that's it.
We raised capital. It was one of the most exhilarating moments of my life and little did I know that it's

going to blow up in my face.

Within 24 hours I lost my job, I lost my salary, I lost my startup, I lost my investment.

You see me doing and reinventing myself again and again and again.

So there's actually like steps.

So the very first thing is. LeapCon 2025 was absolutely transformative.
We brought together over 300 incredible individuals from around the world for a weekend of growth, inspiration, and powerful connections. Some rooms change you.

Some moments redefine you.

And this was one of them.

From incredible speakers sharing game-changing insights to the magical moment when we all

stood together holding hands with massive energy in the room.

It was truly unforgettable.

This is where careers take off, where innovation meets action, and where you step into your next big leap. All right, everybody, it is happening.
Are you ready? Are you really, really ready? How ready are you? Get up and let's give the biggest, warmest, most fantastic welcome

to the phenomenal Ilana Golan.

Come on down.

Let's give her some love.

A little more.

I love you guys so freaking much.

You're amazing.

I love you. You're amazing.
You're amazing. Oh my God.
I admit this is freaking unbelievable and I don't get emotional very easily. I can't believe you all are here and that this is how it started.
What I want you to do for a second now is I want you to get up for a second. All of you get up.
I want you to put your hands on your heart. I want you to close your eyes.
I want you to put aside everything that it took to get here. The hustle and the flights and the security and the packing and the logistics with the family and all of this.
I want you to put all of it to the side. And I want you to close your eyes and think, why are you here? What is the goal? What do you want? What do you want for yourself? What are you creating? What is the dream? And there's no judgment.
Do you want to be on stages? Do you want to be in magazines? Do you want the seat at the table and to feel like you make a difference? Do you want the job of your life and to feel incredible or to have that first class or private jet or whatever it is. So let's go get it this weekend.
Yeah. So we're going to say yes to that dream.
And I want to tell you a little bit deeper in the story of why this was so impactful for me and why I'm so emotional this weekend. Mark Twain says, the most important day of your life is the day you were born and the day you discovered the why.
And if I would have seen this quote probably a decade ago, I don't think it would resonate because I didn't really understand what do you mean the why. I'm alive, everything is cool.
I have two kids. Things are cool.
But something was wrong. I could not dream.
A decade ago, I lost the ability to dream. And I'm laughing because even my dog has a dream, either the bones or chasing the cat.
But he has a dream. And I didn't because I was in survival.
I was trying to figure out where on earth the next fake check. Why am I losing relevance at a speed that I can't understand? Why do I feel like such a freaking failure? And it drove me nuts.
And the reason this was so important, and I want to kind of share a little bit of the journey of LEAP. Steve Jobs said, you can't connect the dots forward, but you can connect them back.
And I want to reflect a little bit of that journey. And I want to also remind you, success leaves clues.
Go look for yours. They're there.
So when I was a kid, I was a pretty shy kid. I stepped into my confidence towards age 16, 17, a little

more. And then I think the Air Force would change my life.
I became an F-16 flight instructor and

the first woman to ever become a commander in my squad. So that created like a pretty big boost

of confidence. In a classic hidden market way, and usually, I think maybe next event I should

tell you some stories about some fuck-ups in the Air Force. I think that's going to lighten your day because it sounds so glamorous and it was mostly scraping my knees.
But fast forward, in a classic hidden market way, I was the youngest student they ever hired in Intel. The only reason they probably hired me is that their competition will not hire me.
But that's okay, because I got my claim for fame there. But after four years of writing code, I realized this is not my zone of genius.
Am I trapped? Is this the only thing I know how to do? And it was 1999. Don't do so much math.
And it was 1999. And if you had any kind of resume with anything

around computers, you would get a job. But here I was looking for a job and looking for my first

client-facing role, and nobody wanted me. It was devastating.
It was like, did I lose my relevance?

Am I done? Do I have to code all my life? And it's amazing how fast you get trapped. Think about it for yourself as well, right? And at that point, eventually I realized what I've done wrong.
My story, and by the way, some of you are already in foundation or millionaire's club or president's club, so you understand how these dots connect. Guests, you'll see it in a second.
But at some point, I realized, wait, my story, I'm talking about all these cool algorithms that I'm running. But if I want a client-facing role, I need to emphasize different points in my story.
So this is when I started to emphasize different points. I found a job pretty quick, negotiated the worst salary in the history of Silicon Valley.
Good job, Ilana. But again, I got a chance at field engineering.
It was the first client-facing role. It was like getting in the arena.
A lot of issues. A lot of the company wanted one thing.
The client wanted one thing. You know, you're like, but when you get good, guess what happens? You get stuck again, right? So, there's like this

stuckness. So, I moved from engineering to technical sales to product, but what I realized

is every time I get good at something, I get stuck. And the reason why I get stuck is because

I get to be known as the problem solver, but not according to what I want to be known.

How many does that resonate? Like how many of you are getting stuck because you become the person that you don't want to become, right? And again, you raise your hand to opportunities, but they're not the opportunities you want. So that's what, you know, and I was just like, okay, so what is happening? Fast forward, I can tell you, and it took me a few decades to find this out, no pressure.
But what I realized is that this like whole stuckness area right there at the corner, and it's a circle that every high achiever will go through. So we work really, really hard, and then we get stuck.
And then we work really, really hard to prove ourselves, and we get stuck again. And what I realized, there's like other people up the mountain, right? They're like, they become these impactful leaders.
They come in the room. They command the room.
They have the executive presence. They become this like indispensable leader.
They have the seat at the table. They're called to all the coolest meetings.
And they have the authority. They have the reputation.
And like, why them? And when they do have all of that, guess what? What's happening to them is that they're in this kind of a hidden market and they're getting all these opportunities because all of them are in some kind of hidden market opportunities. I'm not getting them.
They co-found companies, they invest in companies, they become executives, they get on board, They get advisory. I'm like, what am I missing? Because I can outwork them.
Why am I not getting the chance? So that drove me nuts. Now, I want to take you back also.
There was a pivotal moment, and this is a pretty emotional story. I've never shared it this way.
Is that interesting for you guys? Do you want to hear with a pivotal moment? Okay. So meet little Ilana was my mom.
When I became a mom, 2007, the first kid, 2009, the second kid, my mom gave basically all her career and gave up on it for me. And the first kid, it kind of looked normal, right? Like, I'll settle on my career.
I'll put it to the side because all I'm trying to do is be a mom. Did it again for the second kid.
And at some point when she was about five months old, it started nagging me. This can't be it.
I loved them to the moon and back, but this can't be all my life. My mom wasn't feeling well, and we flew to Israel.
I had one more week for my maternity leave. So I figured I'll just hop to Israel and see what's going on.
About three days later, she collapses in the hospital. We start realizing that she has a tumor, and it's actually not just a tumor.
it's a cancer that went from her lungs all the way to her brain. It's all over the body.
And we're essentially counting the minutes. And for me, you know, I still remember holding her hand.
And it's basically just me and her, I'm an only child. And I remember holding her hand, and I was trying to figure out, like, does she have regrets? But I didn't have the, you know, I couldn't really ask this and I didn't feel like I could.
And I kind of like regret a little bit, not asking some more questions. But at that point, like I was holding her hand and it felt like not enough.
Like I knew she was really appreciating that I love her, but is this really all there is to her life? And the funeral was really small. I mean, it was just like a few family members and some of my friends that showed up.
But at that point, I made a promise that this can't be all there is to my life. And losing my mom became the biggest thing, the fuel that I needed to kick myself in the butt and just do more.
And there's this beautiful quote. I don't even know who this is, but scariest day of your life is the day you die when the person you are meets the person you could have become.
And that to me was, this is not going to happen to me. I'm going to be the best version that I can be.
Okay. So my daughter is five months old, and I'm zooming up, and because that was the fuel, so I, you know, I founded Israeli companies in the U.S.
It was an incredible opportunity. I, you know, from buying the printer and the router to five sites, $15 million in yearly revenue, like we were just like taking off, And, you know, so I was in this uphill trajectory.
But five years after that, I look at myself, I fly every single week, or every two weeks. My amazing husband, who is right here, is the most supportive husband on the planet, because he literally had the kids all on his own for the first five years.
I was not around. And at some point I'm catching myself and I'm like, is this really what I was meant to do? Like, like not being present at all.
And Sean here, by the way, he was part of this. Hey, Sean, you boy.
So, and I was like, is this really, is this what I was meant to do? Like to just fly all the time and not be with the family? Did I, you know, the pendulum flew a little too much. So how do I even it out? So when a friend of mine, somebody I knew for probably two decades, wanted to start a company together, I was like, oh my God, yes, that's it.
This is what I was meant to do. But I worked every second on this startup that we had.
I was so excited. We raised capital.
It was one of the most exhilarating moments of my life. And I thought, oh, my God, how did I get this lucky? So when I left that VP role, it was like a big party.
I wanted to tell everybody about the money that we raised. It was really cool.
And little did I know that it's going to blow up in my face. It was like amazing.
It was like within 24 hours, I lost my job. I lost my salary.
I lost my startup. I lost the investment.
And again, I can tell you like that the ego comes crushing down in a way that it's like, what the fuck? And I think for me, it all came about like with my promise that I'm not going to be that person that does nothing. And here I am.
What I didn't realize is that my identity was attached to my title. It was attached to the company that I was with.
I never built my own identity. It never occurred to me.
So suddenly when I didn't have those, I felt like a complete nobody. And that was a hard realization.
And to make it even worse, I didn't know where I was going. But I'm not the type of person that is all confused.
Like, come on, I got my things together. Like, why do I know where I'm going? Not knowing what I want to do was one of the hardest times in my life.
Does anybody resonate with that, with not knowing what you want to do? Okay. Thank you for being honest.
I started spiraling down. I couldn't sleep at night.
I couldn't wake up in the video. eventually I did leap again and again you know I talked a little bit about it you saw it in the video I started a company I sold the company I stood on boards I've been on stages I've been an advisor and again I realized that I was leaping again and again I was just getting a little better at it so I can leap faster and higher and at that point my geek engineering brain was just like, oh my God, like there's actually a way, like there's actually steps that I'm doing again and again.
By the way, a lot of you that have been following me, I'm doing it again and again in my podcast. I'm doing it again and again to grow a leap.
Like you see me doing and reinventing myself again and again and again. So there's actually like steps.
And for me, it was like, why is nobody teaching this? And that's part of why I'm so excited about this weekend, because this is what I want to do, or at least give you at least some of the map. And again, it doesn't matter what you want.
So when you put that hand on your heart, whether you want massive impact or legacy or thought leadership

or the stages or the awards or the medias, like it really doesn't matter. All we need to do is

start getting relentless about it. But again, it starts with a dream.
And if you're like me,

when you couldn't dream, you can't achieve it. So my commitment to you this weekend,

I want all of you to start dreaming big. Is that a good deal? Is everybody in? Okay.
So let me go really quick over the steps. So the very first thing is to have an unstoppable story and confidence.
Ties into my Intel days, why I couldn't find a job, right? So the unstoppable story is really is really really critical a lot of the people that I see this is where they're missing out their story is just not clear or it's told without confidence we'll talk about it strategically open any door skyrocket your personal brand if you actually do all of these you can leap and you can charge your worth and you do it again and again and again so you can again and again and again. You can create these portfolio careers.
It's amazing. We'll talk about it.
But to change the world, you're going to have to start with changing your world and the people around you, your family, the network. And I can't tell you how important that is because when I was slumping, I couldn't change the world.
I was in survival mode. So make sure that you put your own oxygen mask on.
Without your own oxygen mask on, you cannot help anybody else. Okay, so that's the first thing.
But the truth is that even once you decide on something and you know it, it's freaking hard. And I think this is probably the piece that I didn't understand well enough.
So there's a

little bit of a pendulum, and I'm curious about you in the room. So when I was this VP feeling like a big shot, the pendulum was like my ego was my ceiling.
I didn't really understand that at that time, but I didn't think I need anybody's help because like I'm going to crush it. Being there was actually the lid that prevented me from doing big things.
So that's probably why I needed to slam down in order for the pendulum to go all the way to the other side. But then when it was all the way to the other side, I was freaking out.
I felt like a failure. I felt like I lost every relevance.
And the interesting thing is to get the pendulum right back in the middle, where you're actually coachable and you're actually listening. Because again, from ego, I wasn't listening.
I was hearing, but I wasn't listening. I was hearing to argue.
I was listening to say that it's BS. I wasn't really listening to lean in.
And when the pendulum flew all the way to my fear and my doubt and my darkest moments, I couldn't really believe anybody or anything can save me from it. So I needed the pendulum to be somewhere in the middle.
But if you're in one of those areas, first of all, just know that I was there and it's solvable. But one of the things that people don't share enough is how hard it is.
And Tom Bilyeu, which by the way, was another amazing speaker on my podcast, an amazing guest, says he sold his Quest Nutrition for a billion dollars. And he says, don't ask what's the least you can do, ask what's the most you can bear.
And I can't tell you how many, I think and they are something, I had a few conversation in my home yesterday. And I said, she's like, how many times do you ask yourself, can you do this? And I'm saying every goddamn day.
Seriously, my husband is a witness. Every goddamn day, I say this is the hardest fucking thing ever on the planet.
but I still go. So there is no shortcut.
There is no easy pill that does not exist. But that's why you want the map.
You want the guide by your side. You want the network to lean on and you still just continue.
Okay. And that was really important.
Hey, I'm pausing here for a second. I hope you're enjoying this amazing conversation.
Don't forget to subscribe and download. Now, if you're looking to leap your own career, figure out what's next for you, fast track your own growth and create portfolio career, check out my free 30 minute training at leapacademy.com slash training.
That's leapacademy.com slash training. Now back to the show.
This is a quote from Theodore Roosevelt. And he basically said, it's not the critic who counts, not the man who points out how the strong person stumbles or where the doer of the deeds could have done better.
The credit belongs to the person who's actually in the arena, whose face is marred with dust and sweat and blood. And at best, they'll know at the end the triumph of high achievement.
And at worst, if they fail, at least they fail while daring greatly. And when I listened to Brene Brown talk about this quote, I realized two things, and I wanted to think about it for yourself.

One, when I held my mom's hand, I promised that I want to be in the arena. I knew I wanted something

bigger in my life. So that was already decided.
So once you decide that, I want you to know only

one thing that is absolutely guaranteed you will get your ass kicked. Period.
Is that a good deal? Okay, good. The second thing you need to understand is that there's always going to be naysayers, haters, critics.
Always. Does that hurt? Absolutely.
But if they're not in the arena with you, I don't give a damn. Or at least I will try not to.
I will listen. I will listen to all the feedback.
I always want to get better. There's always things that we can learn.
But I can already guarantee that the people that are in the arena are not the people that will criticize you. Because they know what it takes.
They will be the people that will hold your hand or hold on and double check that you're okay. Okay, so just realize the people in there that are criticizing you are probably not where you wanna go.
So don't give it a weight, okay? That was probably the hardest thing for me. Again, when you get into the arena, it is

really, really hard. But I want you to think of names and people inspire you.
Are they on the

sidelines? Or are they in the arena? Probably in the arena. So we're going to go in there with them.

This weekend, it's not about just to change your weekend. I don't give a damn about your weekend,

but I appreciate that you're all here. We're here to put a line in the sand and to transform

Thank you. It's not about just to change your weekend.
I don't give a damn about your weekend, but I appreciate that you're all here. We're here to put a line in the sand and to transform the second part of your life.
That's why I'm here. Are we a good deal of that? Is that a good deal? Okay.
And in order to transform the life, we are moving from the sidelines, from the fear, from the doubt. The sidelines is where everything is.
The haters, the naysayers, the doubt. Like everything that you can think of.
The teacher that hurts you. The failures that you had.
Like everything is in the sidelines. But you're going to move from the sidelines into the arena because this is where the possibilities are.
So we are getting into the arena this weekend. Is everybody a good deal with that? Is everybody a good yes? Say yes.
Okay, great. So in order to get in the arena, there's a really clear map.
Okay, there's steps. And again, we're going to go over these steps really, really quick.
Again, unstoppable story and confidence, strategically opening doors, skyrocket your personal brand. That is it.
So if I go over these really, really quick, the very first thing you need to remember, your story is not about who you are now. It's about who you want to become next, right? We learned that.
And in order to do that, you're going to have to build that confidence. But here's the catch.
You can't fake confidence when you have no clue where you're going. Trust me, I try.
So the very first piece is that bottom of the pyramid is that clarity. We have to get that clarity of where are we going.
And after that, we have to practice it again and again and again, because guess what? We're not used to talking about our story. And after that, then we can fake it.
We can smile and we can stand tall. We can have our shoulders back.
We can fake the core. We can't fake any of the other pieces.
So we have to get that clarity. We have to get that competence.
Now, there's a few reasons why it's probably harder for some of you. First of all, you have no clue what you want to do next.
That was me. So it took about, I remember, I think I told some of you the story.
I met the CEO that could probably have opened any door for me. He was a venture capitalist.
He was a CEO of a big company. And it took him exactly five minutes to tell me, Ilana, you have no clue where you want to go, right? Not only that he's not going to open the doors now, I just became a red flag.
So I realized that great tip that I got from people, go network, talk to your network, see what they think, was actually hurting me, okay? So I had to understand where I want to go. Then I wasn't emphasizing the right relevant points, like I did in Intel, right? Impostive syndrome is another one, lack of confidence.
Oh, but I don't want to brag. I get you.
We'll fix it. So the big thing is there is a map, okay? And I want to make sure that we understand that.
Strategically open any door. I'm not going to go over this too much, but whether it's cold outreach, warm outreach, get introduced.
I can see a lot of you that don't understand the big people pile that exists. So you're just thinking somebody will give you 20 minutes of their time.
No, they won't unless there's a reason for it. Okay, so we'll learn how to do that.
But the reason this is so important is because every single amazing opportunity you're ever going to find is only in the hidden market. And if you're not playing in that hidden market, you're missing out on all the possibilities that this beautiful life has to offer.
So we're going to have to figure this out. Okay.
This is exactly how I landed my executive roles, the public speaking, the businesses, whatever. And I think last year, who was in San Diego where I shared how I chased Richard Branson for a year and a half? Okay.
Good. Solved.
Okay. But seriously, like there's a people pile.
You need to learn how to play the game. Okay.
Another thing. Let's talk about reputation.
We are in an era of change. I know you heard me probably say it again, again, again.
The pace of change is something we've never seen before. But I always also say in 2007, we all became a media company.
You can like it, you can hate it, it doesn't matter. If nobody hears from you, the assumption is that you don't have anything to say.
On the other hand, it's the best time ever to control the narrative, to decide what you want to reinvent send to and tell the world. So it's an incredible tool if you use it right.
And this is what enables you to be in that hidden market, to be that impactful leader, to open portfolio career, to create your wealth. That's what creates that.
But it needs to be done right. So in branding, there's only one goal.
It's to lead faster and higher. Is that a good deal? Okay.
But here's the thing. There's three types of branding.
One is the basics. If you don't have your crap together on LinkedIn, or you don't have something decent, at least, you're not going to get a chance.
You're not going to get access. You're not going to get a chance at a door, right? But on the other hand, there's visibility.
I want to be top of mind, right? And there's authority. I want to be paid my worth.
So there's levels. You decide which level you want to be in, and probably you're going to need to mature to the next level.
But all I'm saying, there's three types of levels, and we're going to work on all of them. There's also three types of leadership building.
Again, the basic one is just, I just don't want to be the person that sits like this and nobody listens to me, okay? The second one is the visibility. It's the people that come in the room, and suddenly they command the room, and everybody's quiet.
And it's amazing. Like, you say something, they say the same thing, and everybody's like, oh my God, that was such a great idea.
I'm like, ah, I just did that. That is this, okay? And the next level is the authority where you're a thought leader and you're brought into the biggest rooms and the biggest decisions.
Again, you decide what the level that you wanna build. But it's incredible to see the possibilities that come with that.
Again, once you master these, this is where we see people jump one level up, two levels up, three levels up, executive level roles, advising boards, et cetera. So it's incredible to watch what's possible when you master these.
So I just want to give you some context. And again, when you do this again and again, you can leap again and again, charge your worth.
It really is incredible. And I think, again, a lot of you have a front seat to how I've been reinventing myself with this podcast, getting some of the biggest names on the planet on the podcast.
By the way, if you're not signing up for that, who's listening to the podcast, by the way? I'm just curious. Oh, my God.

Okay.

That is amazing.

Thank you.

And I highly recommend it.

Like, it's listening to the podcast, by the way? I'm just curious. Oh my God.
Okay. That's amazing.
Thank you. And I highly recommend it.
Like it's an incredible blueprint of some of the biggest leaders of our time and how they build themselves. So if you're not listening, pick some names that you like and listen to them.
Like I really think it's just going to open your mind to how the biggest leaders achieve their careers. And by the way, how hard it is for everybody.
So for me, I'm learning from every single one of them, but it also gives me the fuel to continue when it's hard. So I highly recommend it.
But also, this is what I did again and again to speak in front of Richard Branson or whatever, right? Like, I do this all the time. I'm not teaching this based on theory.
I'm, you, you can watch me walk the walk. But again, many are trying too hard and they're not using the map or they're not using a guide.
And I can't tell you how a map and a guide changed my life. So lean on the map, lean on the guides, and hack everything we do.
Hack it. I'm not saying steal it, but hack the heck out of it.
Okay, do it for your own. Translate it to whatever it is that you want to sell.
When you're creating these portfolio careers, when you're creating your thought leadership, hack it. That's what it's for.
Every big innovator is standing on the shoulders of somebody else and reaches higher. I remember being annoyed when I saw, you know, like one of my coaches kept sending marketing emails.
And I'm like, why do I need to see all of this? This is all what you're... And then I'm just like, wait, this is incredible.
Like I can actually learn more copy and more emails and more marketing than I learned in my lifetime just by reading their freaking emails. So hack everything instead of saying like, I mean, compile all.
Like think, why are we doing this? Why are we doing everything? How can I apply it to my own leap? Look at every single step. I can't stress how important it is to look at someone else.
Hack the system. That's what it takes to leap, okay? And again, I just, we're going to have an award ceremony in the evening, and we're going to have an amazing dance party.
So first of all, I want to make sure, is everybody excited for this evening? Yes, it's going to be epic. But I want to say, like, what I love about this community is that this is where you can also get inspired by other people leaping again and again.
And these are just some of the people in our millionaires club or our president's club, like Doron, who is sitting here, who is amazing. Like, he was already an executive, but, you know, he then leaped to another company and he rang the bell in NASDAQ.
And now he's doing this M&A thing and he's incredible. And I can't wait to do some incredible things with you, Doron.
And Itzik is right there. I don't know, some of you heard his story, but he moved from being a director that was laid off from his work, the best thing that happened to him, because now he's the CEO of an AI company.
Like, incredible, Itzik. Yes, exactly.
Iran, I don't know if I saw him here. Everybody, I think you met him yesterday in my house.

Was... Yes, exactly.
Iran, I don't know if I saw him here. Everybody, I think you met him yesterday in my house.
Was Doron's accountability partner, by the way. He raised $22 million to invest in startups that are doing impact.
Lior, who I think some of you met him in San Diego. He literally started, you know, a ruiz IT agency and sold it

with the help of Doron for eight figures.

Dganit, I don't know who met her,

but she became a CEO of a public company.

Mavish, who seven extra salary.

Mark, I think you're here, right?

But landed, yes.

So he leaps again, again,

like just incredible to watch you, Mark. I just want to say

welcome to the arena. Are you all in? Okay.

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