Leap Academy with Ilana Golan - From Losing Everything to Startup of the Year: Ilana Golan’s 5 Shifts to Reinvent Yourself | E127

Episode Date: September 30, 2025

Ilana Golan knows what it feels like to lose everything. After climbing from the Air Force to Intel to VP in a Silicon Valley startup, she thought she had made it. But when a trusted co-founder cut her out of their new business overnight, she was left with nothing. No job, no company, no income, and a shattered ego. That collapse became the turning point, forcing Ilana to ask who she was without the titles and what kind of life she truly wanted to build. In this episode, Ilana breaks down the five shifts you need to reinvent your career and the blueprint she used to bounce back from failure, build one of the fastest-growing startups, and land opportunities with leaders like Richard Branson and GaryVee. Ilana Golan is a serial entrepreneur, keynote speaker, investor, and host of the LEAP Academy podcast. As the founder of LEAP Academy, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom.  In this episode, Ilana discusses: (00:00) Introduction (01:11) The Startup Collapse That Changed Everything (04:24) Losing Her Identity and Rebuilding From Scratch (06:22) Launching LEAP Academy and Reaching Startup of the Year (09:10) Reinvention as the Must-Have Skill of Our Era (10:09) The Power of Adaptability: IQ vs. EQ vs. AQ (11:29) The Five Shifts to Fast-Track Your Career (18:30) Commanding Authority: The Three Types of Branding  (23:17) Creating a Portfolio Career for Freedom and Wealth Ilana Golan is a serial entrepreneur, board director, global keynote speaker, and investor in over 100 companies. As the founder of Leap Academy, she teaches professionals how to fast-track opportunities, build portfolio careers, and unlock financial freedom. Ilana has been recognized as a Silicon Valley Woman of Influence, a Top 40 Woman to Watch, and a CEO World Award winner. Under her leadership, LEAP Academy was named one of Inc. 500’s Fastest Growing Companies. Connect with Ilana:  Ilana’s Website: leapacademy.com  Ilana’s LinkedIn: linkedin.com/in/ilanagolan  Ilana’s Email: [e-mail]  Resources Mentioned: LEAP Academy Free Training: leapacademy.com/training  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

Wow, this show is going to be incredible. So buckle up, and I'm sure you're going to enjoy it. But before we get started, I want to ask you for a favor. See, it's really, really important for me to help millions of people elevate their career, fast-track to leadership, land dream rules, jump to entrepreneurship, or create portfolio careers. And this podcast is all about enabling this for millions of people to see a map of what it actually takes for big leaders to reach success. So subscribe and download.

ever missed it. Plus, it really, really helps me continue to bring amazing guests. Okay? So, let's dive in. Within 24 hours, my co-founder decided to take the money, throw me out of the business, and I was left with nothing. No job, no salary, no company. And the worst part, my ego just came crashing down. I didn't realize that my identity was always attached to my title, to the company that I was with. And I didn't know who is Ilana without it. I didn't even know where I want to go. And I'm this driven person who always knew what's next. And suddenly, I don't even know if I'm looking for a job. I'm looking to start a company. Maybe I'm even looking for revenge. And that was one of the hardest moments in my life. And one thing I knew is that I have to fix this,

but I didn't know how. There's a way, because I am on a mission to reach 10 million people with this message. there's literally four steps. If you do this right, you can actually reduce time and tilt the scale of what's possible. you happy and fulfilled and proud and bring not just a paycheck, but the life that you want with that paycheck. I don't do a lot of these solo episodes and I get to speak to some of the biggest leaders of our time, which is, you know, I can't, you know, it's a pinching moment every single time. And if you haven't checked some of these episodes, do. It talks about the blueprints of how people like Richard Branson or the former president of Starbucks or the founder of Zillow, the founder of Siri, the founder of so many Craigslist. I can go.

going on. Like, how did they create the life that they want? What were their challenges? And I wanted to see these blueprints of some of the biggest leaders of our times, challenges, the heartaches. And so if you haven't yet, check them out, subscribe, download. It means the world. And also helps us bring more of these guests. But from time to time, I get these messages from you. And one of them touched my heart because they said, well, you talk about reinvention, you talk about leaps, can you share how? And I was like, you know what, you're right. Like, I didn't actually do that. So what I want to do in this episode is it's going to be a solo episode and it's basically going to walk you through the steps that you need in order to

reinvent and leap your career and fast track in the most incredible way, especially now at this era of change. So I'm really, really excited. If somebody that you love needs to hear this, please do share that with them. It means the world. It really helps us. But let's dive right in. So how do we leap in our career? So to give some context, maybe do you want to understand where this is coming from.

So about a decade ago, I did lose almost everything I had in my life. And to give some context, I did leap again again in my career, from Air Force to engineering and Intel, all the way to vice president in a tech startup. And at some point, a friend of mine, somebody I knew for many, many years, came to me and said, He, Lana, let's start a company together. I got so excited. We rolled up first leaves.

I was working on it day and night. And I got so excited. And we're the typical Silicon Valley story. Within a few weeks, we even raised capital. And it wasn't for one small investors. It was from three prominent Silicon Valley investors. They were valuating a little baby at almost $5 million. It was like a dream and true.

I remember looking at the term sheet, closing my, I was thinking, how did they get this lucky? So good doing the goodbye party from my previous job as a vice president. I told everybody about the startup of the company that we're forming, the money we raised. I was so excited. Little did I know that it will blow my face. Exactly the same day within 24 hours. Michael Founder decided to take the money, throw me out of the business, and I was left with nothing.

No job, no salary, no company, no investment. And the worst part, my ego just came crashing down. See, I didn't realize, and I don't know if you resonate with that, I didn't realize that my identity was always attached to my title, to the company that I was with. And I didn't know who is Ilana without it. Who is she? What does she care about?

Who am I? I didn't even know. where I want to go. And I'm this driven person who always knew what's next. And suddenly, I don't even know if I'm looking for a job. I'm looking to start a company. Maybe I'm even looking for revenge. Like at that point, I didn't know what's going on with me. And that was one of the hardest moments in my life. I couldn't sleep at night. I was grumpy at my kids and my family, my husband, my health deteriorated. I was gaining weight. I mean, I was a wreck. And one thing, I knew is that I have to fix this, but I didn't know how. Now, I can't stress it. Like, I googled

everything. Like, how do I find my, you know, what my passion? How do I find my next career direction? Like, I googled everything. I watched every YouTube on the planet. And honestly, nothing helped. And I felt like I was hopeless. Like, can anybody actually help me? And at that point, made a promise that if I ever get out of a situation, I have to tell the world how. And this is kind of what I'm doing now. So please share, you know, it with the world because I am on a mission to reach 10 million people with this message because I want every single person to know that if you're driven, there's a way, okay? And I want to craft the way. I want to show you the way. So fast forward, I did leap again. Again, I started a tech startup. It was acquired. I'm invested in over

a hundred companies. I sit on boards and public boards and private boards. I advisory. I do public speaking. At the end of the day, I'm a geek engineer. And what I realize is that I am actually doing the same steps again and again. I'm just getting better at those steps so that I can leave faster and higher. And when I was looking at those steps, there's literally four steps. Like, I get really clear on what I want to do. If I'm not clear, I do some experiments. And I align my story. I align my reputation. And guess what? Then I get opportunities. I didn't even know existed and people make even better introductions for me so that I can now negotiate more, I can earn more, I get better seat at the table and I can go on and on.

And I was wondering, I was like, wow, Ilana, like if you figured this out, can this work to help others or to help yourself? So one of the things that I did is, what if I want to start this Leap Academy thing to help others? When I asked people around me, you know, they were like, oh, Ilana, a coach barely makes, and by the way, you guys can Google it, a coach barely makes $40,000 a year. So if you're going to go with the sleep academy thing, man, you're going to be so broke and miserable and what, and again, they're always going to be naysayers. They just want to keep you safe, right? But I was wondering, like, hey, you know, with this mechanism that I'm doing with these four steps, I think there's a way to fast track because everything that I've seen

I was starting to leap again, again, at a pace I've never seen before. Nobody will ever tell you it's reasonable. It's like, can I apply these four steps to starting this business? So here I was applying this business with exactly the same steps, the ones that I will share with you right now. And wow, that was amazing. Like we started in 2020. By 2021, we reached the first million.

By 2023, we were startup of the year crossing every single boundary possible. And in 2024 and 2025, we're one of the fastest growing private companies in America. Like, this basically, if you do this right, and I'll explain exactly the steps, you can actually reduce time and tilt the scale of what's possible. And I was wondering if I can apply the same thing for my podcast. And here I was, you know, launching my podcast in May 2024. By October 2020, we had Richard Branson on the show. By January at 2025, we had Gary Fee on the show. We already had him twice.

By March, we already had an agent sign me up for like podcast tours and book tours. You know, we already crossed a million followers and listeners. And it's just an incredible way to touch so many lives. So I'm so glad you're listening to this because you are helping us make this a better platform and to reach more people. But the reason why I wanted to do this solo episode is because this works. And for me, it was like, so if this. works so well and it creates this unlimited possibilities, then why is nobody teaching this? The other thing that, you know, I want to talk about is that we are in an era of change.

And in this pace of change, if you don't move forward, you're actually moving backwards and losing relevant at a speed we've never seen before. There is no stuck anymore. If you feel stuck, you're actually losing relevant. So what you have to do in this era of change is actually reinvent. and leap again and again and again, and the good news and bad news, you will be invent and leave your career every year or two. Now, even if it's in the same corporate, in the same company, you'll switch functions or responsibilities or tools or whatever it is. And sometimes it will be

beyond, you know, you're going to switch industries or functions or, you know, like to other companies or maybe portfolio careers. You're going to start advisory, mentorships, by way speaking, franchises and I can go on and on because there are just so many options these days on the menu and it's just incredible to watch. The other thing to note, just before I start the five shifts and I go over them, when I was little, we had something called IQ and you would measure somebody's IQ to see if they're smart, if they'll do good in the world. About a decade, a few decades ago, you know, this was switched to EQ, emotional intelligence. And the emotional piece, and actually Richard Branson was one of the first leaders to say emotional intelligence is actually more important

than IQ. And that gave a huge green light to a lot of leaders, a lot of entrepreneurs, a lot of founders, it was incredible. And actually, if you're going to Google this, we are right now in the era of AQ, adaptability quotient. What this means is that adaptability, your ability to reinvent and leap your career has just become the most important skill for the future work. That's why it's so important for you to listen in. And again, if you love what you're hearing, do write me. I'm Ilana at leapacademy.com. It's I-L-A-N-A at leapacademy.com. And we have more training there on the platform at leapacademy.com slash training. And it's going to talk about a lot of the things that I'm sharing and a lot more of that and what is portfolio career and how do you create multiple

streams of income. So let's dive in. Okay. So what are, are these five shifts that you need in order to fast track your career. So the very first one that you need to understand is that you will have to transform yourself. Like, it all starts with you because whether you like it or not, and I know it's a cliche, and I know I would be rolling up my eyes if this was me listening, but everything that brought you here will not take you forward. You know, I was a skeptic. And I thought that I had it all. I was a VP. I knew it all. I've done a lot of things. And, you know, to some extent, my ego was blinding me. The problem is that every conversation is a mirror. If you're not a thousand percent

there, they see right through you. If you're not vulnerable, but also honest, if you, like, there's this combination. But if you're in bad mood or you have bad mindset, you're going to get more objections. Like, it's just not going to work. And you're never going to take as much action as you should be. And the problem is that you need to start becoming the person that you want to become. And it's a really tricky piece because that means that you need to know where you're going. I will probably save it to another solo episode. Are I going to talk about how do you decide? Because that is a really, really tricky one. And I'll touch it maybe just a little bit. But also email me, like message me. If this is something you want me to talk about, I'll share more

about it. Okay. The second shift that I wanted to realize is that you're going to have to transform, just yourself. Number two is your executive presence and your story. What I mean by this is your story has to be told according to where you're going, not where you are today. And the tricky part here is that we tend to talk about what we've achieved and what we've done, not who we are becoming. And again, this is with complete integrity. You don't invent things. But the idea is to emphasize the things that are relevant according to where you're going, okay? Because here's where it's really, really important, especially if you're mid to late stage career, people will not pay you for your time, okay? Gone of the days, when you're young,

people might pay you for your time. Just right a little bit after that, people will pay you for your expertise. Mid to late stage career, people will pay you for the value of the outcomes that you deliver. That means that your message around the value of the outcomes need to be insanely relevant and said with so much confidence because you're judged differently right now. So my question to you,

are you playing the right game? Every single conversation talks about the why you, why this, why now. And now there's two reasons why many, many times we see that the story doesn't resonate. Number one, people have no clue where they want to go or what they want to be known for. So their message is completely irrelevant.

And it's emphasizing all the wrong things. Like I remember, I was in Intel, you know, emphasizing all these cool algorithms that I was engineering. But that would not open the right doors if I want to be client-centric. So guess what? I got zero opportunities until I changed the message. Right. So number one is they don't know where they're going.

And in fact, probably the worst tip that you can get is, oh, talk to your network about what you want to do. No, because when you go to your network and your message is not clear and your direction is not clear, you're actually becoming a red flag. So stop. And I've done that. I went to the CEO that could have opened any door. It took him about five minutes.

Tell me, Ilana, you have no clue where you're going. All right, do you? And it was about a decade ago when I realized that not only I'm not, you know, helping myself, I'm actually becoming a red flag. I need to stop. I need to figure out where I want to go. What is my message before I go to talk to anybody? If you're feeling stuck.

underpaid or unappreciated, or you're simply ready to take your career in life to the next level. I have the perfect solution for you. We have a program that helps you fast track and leap your reputation and career. Become the best version of yourself. Get the dream role you deserve, move up to leadership, jump to entrepreneurship, or even build a portfolio career. This program helps hundreds a year, and it will help you gain the income, influence, and impact that will transform the second part of your life. Watch our free training today at leapacademy.com slash free hyphen training. The link is in the show notes. Now back to the show. The second piece and the second reason why people are not telling the right story is that because

they're so scared to brag, there's so much imposter syndrome that they just can't tell their own story. But here's the beautiful thing. When you, you are really in peace with your own story. It's not about bragging. It's about inspiring. It's about becoming the role model that you're meant to be. It's about opening possibilities and allowing others in. So that's the second shift. Number three, really, really important. Hidden market.

Again, the secret strategy is that the old ways that we've been looking for jobs or starting businesses do not work right now. Everything, especially mid to late stage career, everything is happening in the hidden market. Basically, who will bring opportunities to our way? Are you top of mind for the right things? Are you top of mind at all? But are you top of mind for the right things according to what you want to be known for?

If I was known for being the expert in cloud and data centers, this was not serving me if I want to be known as the founder of Leap Academy, helping leaders reinvent their career. So you need to choose what you're known for. 2007, we all became a media company. Whether you like it or not, you are a media company. So the beautiful thing is, again, if nobody hears from you, the assumption is that you don't have anything to say. That's a bad place to be. But again, this is the best way to control the narrative to make sure people bring the right opportunities your way according to what you want. So it's a goldmine of opportunities. But if you think about it, every type of opportunity like clients, partnership, executive level roles, founding teams, mentorship and startup accelerators, advisory, board seats, special leadership retreats, special forms. of these things are happening only at the hidden market. Nobody's like searching on a job board who can

keynote my next event, right? Like, people need to think about you. And again, that's exactly how I landed my first clients, my speaking opportunities, my executive level of worlds, public boards, you know, grew businesses, invested in companies, et cetera. And this is why I hang out with, you know, Richard Branson and his private island and so many cool things that happened in my life. But again, it's all in the hidden market. So are you playing that game to be? in the hidden market and to receive these opportunities that you want to receive. So that's really, really important. That's the third shift.

The fourth shift is to transform your brand. What I mean about by this is, again, like we said, you already have a brand. Some of you come to me and say, but Ilana, I don't care if I have a brand. That's BS. You have a brand. The brand is what people think about you when you're not in the room. So you already have a brand. The question is, is it telling the story according to what you want to be?

or according to who you've been. And yeah, you even top of mind. So when those opportunities open up, will people think of you? And if they do, great, but this is the best, incredible way to control the narrative because the problem is most of us driven people,

we just wait for opportunities to fall in our lap or we wait for, you know, somebody to just, you know, like give us the sprays that we want. But that's not how it goes. Now, there are three types of brand, branding, that I want you to think of. The first type is kind of the, very, very basic. I need the LinkedIn and the resume to not be a red flag, or I need the website.

If somebody looks at that, you know, in five seconds for it to not be a red flag, et cetera. So the very, very basic branding is really, really important. The idea is if somebody is looking at you or your story or Google's your name for five seconds, just to make sure it doesn't scream, oh my God, don't make this introduction, right? So the basic branding is really important. But if you want to move to the two next levels, the other two levels of branding, after the basic one, there's visibility. Visibility is basically being a little more visible on a panel, maybe a small keynote, maybe some kind of an advisory, maybe on a podcast. So a little bit of visibility. The authority level is the third level.

And this is where you start opening up to opportunities. You didn't even dream were available. And this is where suddenly people from all over the world start bringing you opportunities and want to pay you premium to deliver the outcome of the value that you deliver, right? And that's where it becomes like really beautiful. This is where authority is where you get the media. It's where you get to keynote in big places. Maybe you get even paid to speak. It's where you get invitation to really, really exclusive things.

It's where people bring clients your way and you're paid premium to. help those clients. So this is where authority plays, right? There is an incredible correlation between wealth and how you play with that authority. Now, followers does not mean necessarily that you're going to make it, but you want to make sure that it's followers or the people that follow you are the right type of people that will actually bring the right opportunities your way or pay you premium to deliver the value. Because again, if I'm a company CEO, I mean, I want to bring an incredible speaker that will move the needle passively on my team, on the company, et cetera. Now, if my company is doing about a billion dollars in revenue, that means that my sales team

is really, really important. Like, every minute is critical, right? But if I can make the, if I can bring this keynote speaker that will make my sales team just a little bit better, just a little more productive, that's a million dollars. Even if they just improve them by 1%, that's a million dollars for me, right? So is it worth paying premium for this one hour? Is it worth $20,000, $50,000? Of course it is. But here's the catch. At that point, it's not enough that the person will tell me that they're good. It's not enough that somebody recommended them. Their brand needs to tell that story. I need to be able to look at them, to look at other videos, to look at other media mentions and say, oh my God, I feel like they can really help me. That's the reason why I will

bring them in front, right? So again, this is really, really incredible, but the catch is that your brand are going to have to tell that story in order to make it. But there's 20 different ways to build that brand. So everybody, when they think of branding, and we'll talk about it in a second, when they think of branding, always think about just like, oh, but I don't know if I want to post on Instagram or I want I don't, you know, there's like posting on LinkedIn or Instagram or Facebook, it's just one way of building a brand. There's 20 different ways to build your brand. And the more you're relentless about it, the better it is.

Because you can have a website. You can have a blog. You can do public speaking. You can have a webinar. You can be in charge of a community. That's an incredible way to build a brand. You can have a book. You can be on podcast.

you can do content management, you can have awards, you can have an email list, you can have press releases, you can be on TV, it can be at radio. And I can go on and on, and on our website, we're going to have some resources for you. But seriously, there's endless ways to build your brand. And by the way, check out leapacademy.com slash training. We're going to, you know, walk you through a lot of this, you know, in training and a lot more details, very visual with slides and stuff. But seriously, there's so many ways to build your brand. The question is, are you controlling the narrative right now? And your brand is what will make people pay you premium.

That's what moves the needle on people's wealth. It's not going to be another 10K that you're going to negotiate in the next job. Again, that's awesome. That's 100K in a decade. But that's not what's going to change your life. What's going to change your life, and this gets us through the fifth shift, is when you learn how to create a portfolio career and how to fast track. Now, portfolio career is essentially multiple streams of income, of ventures, et cetera.

Again, sometimes it's for income, sometimes it's for status, sometimes it's for fun, sometimes, but every single person will have multiple streams of ventures. In fact, the co-founder of LinkedIn himself said on LinkedIn, it's like a career is no longer a single ladder to climb. It's becoming a portfolio of project, experiments, and creative bets. So if you're going to actually look at the top billioners in the world, they all have at least five income streams. At least. In fact, if you look at millioners, 50% have four income streams or more. So again, why is nobody teaching this? Right. So Leap Academy right now is the only formal education to portfolio career. And for me, it's a no-brainer because people want more than just this one thing. to work in one place for 40 years. And that's it. People want more. They want fun. They want to travel. They want freedom. They want legacy. They want thought leadership. They want generational wealth. I can go on and on. And the truth is one career is not going to give you all of that. But that's where you need to start understanding that you need to leap again and again and again. Every single time you're going to stand on the shoulders of what you achieve and name higher. And every single leap, you're going to learn to negotiate just. a little more and build your brand now according to the latest leap so that again you can start

accumulating wealth because that's that's wealth and possibilities that's freedom and when I talk about freedom that's freedom of choice and this is why we see people even in w-2 and they're you know in jobs and now starting to do mentorship and startup accelerators and advisory and take some equity and do some public speaking and teach and whatever and now they're starting to create these incredible portfolios, in fact, we see an average return on investment of $2,000 when people are starting to learn how to leap again again. $200,000. Think about it. In a decade, that's $2 million, and that's assuming that they're not leaping, you know, even bigger and bigger things. For some people, it's a lot more. The biggest cost in our life is always, always the money we're not making. So the only

question you should always ask yourself is what's the fastest way I can grow. Okay. So I'll just recap the five shifts in order to fast check your career in the biggest, biggest way possible is first of all, you're going to have to shift yourself according to where you're going, not where you've been. You have to align your story and executive presence according to where you're going, not where you've been. You have to start playing in the hidden market so that the right opportunities will come your way and number four are you going to build a brand so that that authority will create an opportunity for you to be paid premium for the value that you bring and now you can start leaping again and again because leaping becomes an art that you can do again and again and kind

of checklist of all the biggest thing that you want to accomplish in your life and now you know exactly how to achieve each one I mean that is so powerful and again it's also a cue right that is adaptability quotient. That is the most important skill for the future of work. So congratulations on, you know, at least understanding that you want to leap again, again, again. I can't wait to see where that takes you. I wanted to write us atilana at leapacademy.com. Again, I-L-A-N-A at leapacademy.com or check out our training.

It's leapacademy.com slash training. Let us know where you're heading. Let us know what's next for you. And if this was helpful, do share it with others that should reinvent, leave their career so that we're going to make the world a better place one leap at a time. Have a beautiful day. I hope you enjoyed this as much as I did. If you did, please share it with friends.

Now also, if you're feeling stuck or simply want more from your own career. Watch this 30-minute free training at leapacademy.com slash training. That's leapacademy.com slash training. See you in the next episode of the Leap Academy with the Ilan and Golan Show.