Leap Academy with Ilana Golan
LeapCon 2025: Ilana Golan on Taking Bold Risks That Lead to Unstoppable Career Growth
Tue, 01 Apr 2025
After her first startup collapsed, Ilana Golan lost her job, salary, and investment. Feeling like a failure, she spiraled into doubt and uncertainty. But instead of giving up, she made a promise not to be the person who does nothing. That decision led her to reinvent herself and found Leap Academy, a community helping others make bold career shifts. In this 2025 LeapCon, Ilana shares her emotional journey from feeling stuck in her career to becoming an impactful leader. She provides actionable insights for navigating hidden markets, building a personal brand, and growing continuously in your career. Ilana Golan is an entrepreneur, board director, and investor in over 100 companies. As the founder of Leap Academy, she helps professionals navigate career transitions, leadership, and personal branding. In this episode, Ilana will discuss: (00:00) Introduction (02:27) The Power of Dreaming Big (05:06) Breaking Free From Career Stagnation (09:21) Turning Tragedy into Fuel (11:49) The Collapse of Her First Startup (16:06) How to Reinvent Yourself Again and Again (18:12) The Cycle of Ego, Fear, and Growth (21:35) Handling Critics and Naysayers (22:49) Building True Confidence in Business (25:34) How to Open Doors in Hidden Markets (26:36) The Three Levels of Personal Branding (30:11) Learning From Others to Accelerate Growth (31:41) Inspiring Success Stories From Leap Academy Ilana Golan is an entrepreneur, board director, and investor in over 100 companies. As the founder of Leap Academy, she helps professionals navigate career transitions, leadership, and personal branding. She has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Ilana is also a sought-after keynote speaker and has been featured on Yahoo Finance, Fox, NBC, and more. Connect with Ilana: Ilana’s Website: ilanagolan.com Ilana’s LinkedIn: linkedin.com/in/ilanagolan Resources Mentioned: Leap Academy Website: leapacademy.com Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training
Chapter 1: What is Ilana Golan's journey from failure to success?
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 the 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. 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 wanna 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?
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Chapter 2: How did the collapse of Ilana's first startup impact her career?
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 kind of 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 all 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.
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Chapter 3: What are the steps to reinvent yourself according to Ilana Golan?
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 where 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?
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Chapter 4: How does Ilana Golan handle critics and build confidence?
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 other people up the mountain, right? They become these impactful leaders. They come in the room. They command the room. They have the executive presence.
They become this 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 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.
Chapter 5: What strategies does Ilana Golan suggest for opening doors in hidden markets?
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 Lil Ilana was my mom.
Chapter 6: How does personal branding play a role in career growth?
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 love 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 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
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Chapter 7: What success stories from Leap Academy can inspire your career?
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, because that was the fuel. So I founded Israeli companies in the U.S. It was an incredible opportunity, 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, 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, right?
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't tell you like the ego comes crushing down in a way that it's like, oh, And I think for me, it all came about with my promise that I'm not gonna 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 morning. I was snappy at everybody around me. My health deteriorated. I was like, why can't I figure this out? I think I'm a smart human being. Why can't I figure this out? I Googled everything.
I found either very motivational, who you can do it, or people that live and inspire me. I'm like, this can't be it. So at that point, I did make a promise that if I ever figured this out, I have to tell the world how. And I think this is part of why this weekend is so emotional, because just seeing all of you in the room is just incredible. So first of all, thank you for being here.
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