Career Resilience in the Age of AI with Ilana Golan

Hey everyone, welcome back to Make It Happen Mondays where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us.

Now, today I'm talking with Ilana Golan, founder of Leap Academy and a former F-16 flight instructor in the Israeli Air Force. Pretty serious. And by the way, she did that at 18 years old. Uh she grew up as a shy kid in Israel, found her confidence in the military where she became the first woman to lead her squad, got recruited by Intel during her first semester of college, and went on to lead sales and growth teams in tech for over 20 years. She helped take a company through a $300 million acquisition, reinvented herself multiple times, and now runs Leap Academy where she teaches professionals how to future-proof their careers through what she calls a portfolio approach. Her message is something I've been preaching for a while now, which is that in a world moving this fast, your ability to build skills, relationships, and a personal brand is what's going to set you apart. We get into her origin story, the power of the hidden network, how to take a leap when everything feels uncertain, and why hard work still matters more than anything else. This one is a fantastic conversation. Let's make it happen.

Ilana Golan, welcome to Make It Happen Monday podcast. How are you today?

>> It's so fun to be here, and I'm excited. Yeah, I was we were saying right before we got on here, I am very interested in this conversation. Not only cuz your background, but because of what you're doing right now with Leap Academy and the transformation you're trying to help people go through in a very uh tumultuous and transition-oriented time uh that that we're in right now. So, we're going to get to that, but as my audience always knows, I love starting with the origin story. And there's some I mean, you got some really unique things, but I before we even get to the F1 stuff, like the fighter pilot thing and everything else, I want to just get some perspective of where you come from. Like parents, growing up, like what kind of Where did you get the drive? Cuz you obviously have it and and you're obviously quite dynamic in it. And sometimes that's a nature nurture thing. So, I'm just kind of curious how much is it nature, how much is it nurture?

>> question because I actually grew up a pretty shy kid. Um so, I was pretty shy. I think I had a little bit of confidence when I was really young. Um and I think sometimes in your childhood things somehow dim your light. And I definitely I and I I I can't point to something specific or but something dim my light. I was definitely very Um I was lacking confidence as a kid and then uh somehow I stepped into leadership towards I would say right before graduation. So, and suddenly I found myself again and I am Yeah, I mean, definitely had a little bit of a roller coaster. Um I grew up uh back in Israel. Um I guess it would be called probably you know, middle class. Although, you know, based on what middle class has right now, we definitely did not

>> whole different conversation, isn't Like we had one toy, you know, and I was like really proud of that toy. Um so, it was definitely a different level of middle class, but um yeah, I had you know, great loving parents, but somehow lost my footing at some point. So.

And so, when you grow In Israel, do you always do you Does everybody go in the military?

>> it's Men and women? Okay. And that's where Did you choose the F-1 flight flight instructor?

>> so I got in So, I was pretty lucky. Um I you have a few tests that you need to go through, but I did study math and physics. So, I was a prime candidate for Air Force. Um and I stumbled on it. Like I didn't even know it existed to be an F-16 flight instructor. Women at that time were not really allowed to be combat pilots, you know, in in some form. So, um that wasn't even in my radar. Like it wasn't even something that I aspired to. I felt really lucky that I got the best role that you can have as a 18, 19, 20-year-old. Um it is insane. I the the amount that I learned and the responsibility that I had, you know, at the age of 18, 19, 20 is something that most people will not have at the age of 45. So, you know, are you know what I'm saying? So, it's like it was incredible but also a lot of learning and a lot of hard moments, John. Like I don't want it to sound like it was all good. It was there's some really hard moments and a lot of teaching moments and I think they made me in retrospect a little more resilient to where, you know, when things are hard. So, I think in in in hindsight it was a great lesson.

Like I mean, at 18, too, I you obviously did well in school and and picked up on stuff pretty quick because you you became a leader within that structure pretty quick as well, right? I mean, you said

>> you know what? I was never a brilliant student. Like I was never the A+ you know, student. Like that was never me. I I think I'm dyslexic and nobody ever found out. I have tons of spelling mistakes. Thank God for spell checkers. Like I think that I wasn't I wasn't like one of those like really incredible um students. I think that's also was part of the lack of confidence because I was never great. But I think I knew how to compensate when it came to hands-on. I could outwork anybody. I'm a hard worker. I'm I don't slack and I think that really helped. Like I I compensated for my being average with hard work.

That's See, that's why I knew I was going to love this conversation cuz I very similar. Like I I was a B+ A you know, but I had to work my ass off for those grades and and I was not the smartest kid and I remember my dad My dad was probably the smartest kid I smartest person I've ever met my entire life. Like he So, you're the military You know the AWACS? You know the the US the AWACS thing? So, my dad was an engineer and he would he was the one who built the what on the team that built the AWACS, right? And so, I was always like intimidated by his intelligence I think when I was a kid. So, it was almost one of those like I diverted towards non like oh, I'm not smart, but I but I knew that I could work outwork anybody and that's what I kind of hung my hat on for the longest time was like I'm not the best basketball player. I'm not the best student. I'm not the best, but I will outwork you and there's no question about that. And I think that part I I'm curious was that something that you had in you from like like again nature nurture scenario here cuz cuz it's hard to teach. A work ethic is hard and I'm I'm sure as you see this with Leap Academy and everything else. It's like I can give you all the skills, but if you're not willing to put in the work it's not going to happen. So, was that innate in you or was that was that something that you were just always a hard worker or did you kind of have experience in seeing that hard work that you replicated?

>> It's a great question. Like I don't know where that came from. Um but it's definitely something maybe because I I realized that I'm not the great student like you said, right? Like the grades are not amazing, but I could sit and learn and and I think at some point actually my dad sat with me on spelling specifically because I was just horrific at it. And you know, he's like how can you be so bad? And he literally like sat with me. My mom already lost her patience. She was like, she's a lost cause. And he literally sat with me. And I think maybe that created that little hunger that, you know what? If I sit on it, I'm eventually going to make it. And I think that was basically the beginning. And if since then, I I'm still the hardest worker down. Like, you know, I I hate when people pretend like they just sit on the beach all day and millions come their way. Like, it's just such BS and we live in such a BS time. I'm not going to jump ahead, but I'm just saying like, I'm going to admit it. Like, I'm the hardest worker and I think that created results. So.

No, I I don't And I don't think there's anything I I think that needs to be celebrated right now. Because everybody's looking for the hack. Everybody's looking And I keep telling like, I have 12 guidelines to success that I put together a long time ago after Think and Grow Rich. And those, you know, I read that book, but it was um, you know, the first one is work hard and smart.

>> Right. You know, everybody says you got to work smart. Like, shut up. You have to work your ass off. Like, anytime somebody's ever asked me, John, what's the secret to your success? I'm like, I work my ass off. That's it. Period. I'm not that smart. I'm not that bright. I I just work out I outwork you. And I still can't at 50 years old, I can still outwork 95% of these kids coming out of school in a lot of ways. And that's I don't want to skip ahead too much either, but that that's the part that from a learning standpoint, I'm curious how you address that. Is it cuz I'm guessing you attract people who are a little bit more driven. But do you come across the ones who have all the skills in the world, but you just like they're just not willing to put in the effort? And and can you connect with them in a way that gets them to wake up?

>> It's a good question. Um I think it depends on why somebody's not taking action. So, I think there's a few like that it was time I learned there's pockets, right? Some of it is they're simply lazy. And sometimes you just can't do anything about it. Um but I think in many, many cases is because people fell off the horse of success. And if that's the reason, then if you can tie back to why this even matters and what, you know, what their pain is and what their dream is and and show them that there's a way out of the situation that they're in, um, you can get people back on that horse of success and show them the way. So, I think it really depends on what is the reason. Did they lose their footing? Did they lose hope? Did they lose I it's so easy to lose hope when something is wrong. So, we can talk about that all day long.

All right. Well, I I definitely one of the things that stood out was, you know, you raising a lot of money and then having your friends uh kick you out. That That That one hits hard for me cuz some something similar happened to me. But before we get to that one real quick, let' let's talk about, you know, so then you went into engineering and I think it was your your first semester you got hired by Intel.

>> like score to that. How was How did that If you're not good If you're not a good like student, and you Who Who the hell gets picked up first semester by Intel?

>> the military. So, that's where I learned the hidden market, right? The hidden market is real. Like it's who has you top of mind. And again, I was just really good in the military. I was the first woman to ever become a commander in my squad. So, that, you know, kind of created a little bit, you know, a little bit of a press, I guess, a little more recognition. And one of the people that were with us in the military was actually in Intel, and he was pretty high up. So, he noticed me in the corridors. He's like, "Hey, come on over. Like, I want to tell you something." I'm like, "That's okay. I'm not there yet. I'm just first semester." He's like, "No, no, no, you come." I still think that they took me because, first of all, it was '96 or '97, right? If you had anything to do with engineering, they would you know, they would take you. But, also between the military and the fact that I was studying engineering and the fact that they were probably afraid that the competition will take me, you know, I got in. You need to also have some luck on the way. Uh of course, right? And but I but I think you make your luck, right?

So, did that with that the hidden network, right? You cuz we talk a lot about like the portfolio careers of of of rounding out and and understanding, you know, it's not just about hard work. It's not just about your ability to cold call and stuff like you know, in sales, but it's about partnerships. It's about relationships. It's about So, when did it kind of start to really crystallize for you that you you did need to kind of have a portfolio, if you will, of your brand, your skills, your you know, people you knew. Was that something that you evolved into later in your life or was that

>> Yeah, much later. I think at that point I just realized the power and the magnitude of who knows you and who thinks about you when you're not in the room. And that became very prominent and and I think everywhere like everywhere I went since then it was startups. I was the person brings Israeli startup to the US and that, you know, that that was also I got in from somebody that knew somebody and etc. So, I realized the power of the hidden market and the hidden network and people that think about you. But, unfortunately, I understood the power of a brand or portfolio much much much much earlier much later. So, I needed to fall deep to learn that.

Well, the I think the like brand didn't really even become a thing. Like I I kind of had the same trajectory as you. I just kind of kept doing stuff. Like doing trying to help people out, you know, I I there was a networking group that I belonged to early in my career. It's called BNI, Business Networking International. And their whole philosophy was Givers Gain. And it was a whole mentality of give, right? Don't expect anything in return. And so, I kind of embedded that and developed relationships, and they just kind of evolved to a brand. And and I didn't even think of it that way. It was just what I was doing to try to spread as much positivity as possible, but also, you know, connect with people. So, with you with like with what you teach now to students, how do you get them cuz I think we've lost the art of networking of of really building like relationships that aren't especially in in the sales world that aren't like directly tied to a revenue thing, right? And and now that we're all behind a a Zoom session and it's all transactional, I think one of the best things a rep can do right now is go out to events and and start to shake hands and kiss babies and and and just kind of develop their first of all, their ability to relate to people and and and communicate, but also to develop relationships that might not bear fruit in the short term. So, how do you how do you get them to kind of crack that code part of their portfolio, if you will?

>> Yeah. So, it's a good question. Like, I think um right now um we are in a lack of trust era. So, first of all, we're going to need to understand that we're in the lack of trust era, and I mean, we can almost have this conversation with notebook and lamb and, you know, some, you know, some AI avatars. Like, as sad as it is, that's kind of where the truth is. So, you don't even know what's real or not real. Hey, this is real, actually, but I'm just saying you don't really know, right? So, the truth is, you know, the the that I think we're going to see a pendulum, right? It flew all the way to nobody needs to see anybody, and you can actually build a multi-million dollar business without seeing anybody, which is kind of us. But now it's time to, you know, the pendulum will have to fly back to actually it is a lot about communities. It's a lot about relationship. Um the trust factor is going to need to, you know, to be established. So, I think we're seeing a pendulum that flies right back to back to a little more relationships and and and more community based. Um but we are in an era that things are just moving at a pace that are hard to describe. So, I think people are just overwhelmed. Like I think that's the the bottom line.

I don't know. I It is mind-numbing right now how fast things are moving. I mean, you and I both been through those same like we saw the internet, we saw it, you know, in high-speed internet, we saw the iPhone and and all of them were kind of like, okay, cool. This is this hockey stick. And and I think the thing that's so uncomfortable right now is that we're watching things like create go through their life cycle and die right in front of our eyes. Like within months, you're seeing companies spin up and then all of sudden Anthropic releases a new update and that company's now irrelevant. You're like, oh my god, like And that we've never seen that like we cuz I think historically when things went out of vogue or, you know, whatever, it was like, oh, oh yeah, remember that? Like that oh, you know, cuz they gradually left us and they quote-unquote died, right? Whereas this stuff is like bang bang. And I think people are now scared, obviously, um about how fast things are moving, but they're almost Now they're stuck because they don't know what to do. Like there's a book that I I talk a lot about which is Jolt Effect which talks about from a sales standpoint, you know, it's not no decision we're losing to anymore, it's indecision. And the reason is is there's just so many things going on. There's There's so many options and things are moving so fast that people are scared to make decisions. How do you get people over that fear of of taking the leap, if you will, to own their own career, to start a new job, to get away from something they feel stuck in? How do you get them to move when it's so scary right now?

>> Yeah. So, first of all, I think you said first of all, many really important things, but I want to emphasize one specific one. Um in an era where action taking is actually basically a commodity. It's actually really easy to to do the action taking because AI will have its own action takers and it's like between the different LLMs and between the agents and between all the automation, the code that you can write. Like the action taking is actually really easy. The decision-making is where it becomes harder. So we are actually becoming the bottleneck. So we going to need to build even a bigger muscle to make decisions really really quick. Um so what you said about decisions versus indecisions is like really really important. So our biggest hold up in life right now, uh it's always been indecision, but right now it's actually hurting us to an extent that is hard to describe. So um and I actually have a really cool little way that I look at decision-making. I'm happy to share if that makes sense, Don. Um so I call it the 555 rule um and it actually changed my life. So So I was in that bottom of my barrel trying to figure out what's next, uh figuring out like what what do I want for my career, etc. And um and I think there's this feeling that you going to need to make this decision for the rest of your life and that's a really daunting decision. And in the venture capital world, um there's uh you you you never need to it takes time until there's I'll explain the venture capital world first somebody that doesn't know, maybe the listeners, but so in the venture capital world, the basically a venture capitalist needs to decide eventually if if this is worth investing money in a startup or not, right? But until they actually get there, it's actually fascinating. So if you think about it, there's going to be thousands of people applying to the venture capital. Now in general, they going to be some kind of an admin that just kind of looks at the application and just says, is this worth an hour? That's all they need to decide. They don't need to decide is this worth investment because that's impossible to do, but is this worth an hour? And in those hours, they're going to have a phone call and they just need to decide is this worth 5 hours of the partners meeting them in the you know, so and in those 5 hours they'll decide is this worth 5 weeks if I you know, to do some due diligence and those small steps actually make decision-making a lot easier. So, in the 555 rule what I've done is basically it's 5 hours, 5 days, 5 weeks. So, what I like to say to our clients is, you know, like again, there's a lot of things around how to find your zone of genius and your must-haves and your you know, like what you want to do. Ikigai But eventually you just have a list of I don't know, three to five options that are like maybe a job, maybe this title, maybe a consulting, maybe advisory, whatever, right? Like you have five options and I you know, just choose one for a second and say is this worth 5 hours of my time? But just dedicate it because a problem is when you have too many options that our scattered brain can't fathom all of them together and can't compile all of them together. So, we just take one. Is this worth 5 hours of your time? And in those 5 hours, all you're going to do is research as much as possible about that option and go go at it, right? Like the person that is there, where you know, what is their career trajectory if you do this, what are the options, what do the people talk about, what do the people write about? Like just research as much as possible. And again, at the end of the 5 hours, you don't need to make this big decision. All you need to make is is this worth 5 days of my life? And then you just go at it and you almost try it on a little bit, right? You test it you test your pitch. Does my pitch make any sense? Does it feel good? Can I try it with maybe just a couple of friends? I'm not going to go to the top CEOs right now and you know, become a red flag, but can I test it with my spouse? Can I test it with my kids? Does it resonate? Does this feel good? Can I, you know, maybe, you know, like research something, maybe post one thing and just try it out. So, it's really more of a minor, you know, mini trying out. And again, all you need to decide is this worth 5 weeks of your time, right? Now, you're literally going to try to brand yourself and create a little bit of the foundation. And I think when people look at it and the beautiful thing, you know, look at it in those stages, it's a lot easier to make decisions, but you can also decide, you know what? This sucks. Like I don't want to do this. Like so, I'm going to go back to the drawing board and go back to one of these options, but the good news is that you wasted now 5 days instead of years climbing the wrong career ladder. Right? So, thank God, right?

I mean, because one of the things that I say is that the the worst part is actually not a bad career. The bad career is screams at you, get off, get off, get off. It's actually the good career that isn't yours. So, to me, it's like this is just a such an easy way to start making decisions overall. So, we gave an example of career, but this is true for market fit, this is true for any kind of other decisions you need to make.

How does that fit into the bigger picture, right? So, and and I guess I'm curious what your your perspective is on goal setting these days with how fast things are moving and how, you know, people talk about 5-year plans, 10-year plans. I'm like, I can't see 5 days, you know, in front of me right now. So, you know, but on the flip side, you know, I think people do need to have some type of a vision for their life. For their for where they want to be, why, you know, and that their why in some ways, right? But how do you coach that within that framework, right? And and does it kind of start by taking a step back and and having that real conversation with yourself of like, what do you what does, you know, life look like for you at the end of the day. And now let's put those five into context of that. Is that the exercise that you go I'm just kind of curious how you look at things and how fast things are moving right now and and goal setting.

>> you're you're spot-on questions. Um when I look at the future, um it's impossible to figure out what exactly is going to happen. I just came back from the World Economic Forum in Washington, D.C. and there was like the IMF and the World Bank and there were some fascinating meetings, but one of the things that came back again and again is that first of all CEOs will just have to admit that they absolutely no clue. They just don't have a clue. But they have to build organization that can cope with the adaptability and and the pace of change. So So it's impossible to really read the map for 10 years. That's impossible. What you can do is figure out what's the feeling that you want to have in 10, 15, whatever years. And I think when you align a feeling, it's not necessarily what what what gets you excited. What is that thing? If nothing is you know, if everything is possible and there's no shame and you can be as shallow and as selfish as possible, what what do you see as you know, in those you know, in your sight like do you see the stages? Do you see the first class? Do you see the second home on the beach? Do you see you know, you flying the entire family to some villa in Italy? Like whatever. I'm just making this up, but I'm saying Yeah. Like align with the bigger, you know, like what do you want to feel because then the vehicle will present itself based on the must haves and your zone of genius and the experiments, etc. But there's no way for you to predict exactly where the company will be or what, you know, how many people you're going to lead or like that to me is just impossible at this pace of change to to really create.

I agree and that's why I think like the vision, right? Like what what is what is happiness, what does success look like? Forget about the money, forget about the job for a second. Just like what is what does happiness look like for you, you know, a few years out here? Um and then based on that, let's back into Okay, now what kind of job, what kind of money do you need to make to be able to do that? And then we can start making some decisions. So is that what you had to go through um when So you, you know, Intel, you know, then couple other startup, and then then you went to a startup with a friend. I'm very curious about this one. And um if this is and probably a hard conversation cuz it's a hard conversation for me to have about what happened to me. Um you said you rock bottom. Like so you went you got what is it? 800 800k from a great Silicon Valley investor and Silicon Valley

>> investors. So I'll share this story, John, because I think it's important. I I think that at that point, and also like to give it some context, right? At that point, I'm vice president. I feel great, you know, I've sort of arrived, right? Like I I, you know, and and I think that's important because I think also my ego was a little bit more than it should have been, but that we can talk about that, right? But um but again, a friend of mine came to me and said, "Hey Lana, um let's start a company together." And that was so exciting. Um and we did the Silicon Valley thing. You go raise capital. Like I sit right here at Steve Jobs' garage. It's right right across my fence. So Yeah, so we're totally inspired and um they were evaluating our little baby at almost $5 million. It was $800,000. It was hitting the bank. Um and I remember looking at the term sheet. I'm like, "Oh my god, how did I get this lucky?" So, during the goodbye party my from my previous job as a VP, I wanted to make sure people don't follow me or don't get scared that I'm leaving. So I wanted to give them the context, like I'm going to chase my dream. And we raised capital. It's going to be amazing. And I, you know, Macy told everybody about the company and the money we raised. And within 24 hours, John, it was like it was actually incredible. Within 24 hours, my co-founder decided to take the money, threw me out of the business, and I was left with nothing. It was so shocking. Like suddenly I find myself within 24 hours from like one of the most incredible moments of my life to suddenly no job, no startup, no, you know, salary, no investment, like nothing. And I think the hardest thing, John, and I think I wonder if some of the listeners can resonate or relate to that. Um for the first time in my life, I realized my identity was always attached to my title, to the company, to right? Like that's how we grow up at some point, right? Like we this it was my measurement of success. So, without the title, I felt like a complete nobody. And and to make it even worse, like I didn't even know where I wanted to go next. Like I wasn't sure if I want to go back to the same type of job. I mean, there was a reason why I left it, right? Like so, am I really going back to the same thing? Or do I want to start another business? Or am I looking for revenge, John? Like that was on the menu. I was just like I was I know the feeling. I was so pissed how that all happened. But I think what people don't usually talk about is a downward spiral that happens. And and if I'm being really honest and and vulnerable, um that was by far the hardest time in my life. Point blank. Like I I didn't just lose a startup or a job, I lost myself. And you you can't sleep at night. I was just like tossing and turning, feeling like a failure. How did I How did I let this happen? And I should have been further along my career. Am I starting from scratch now? I was I was literally I couldn't sleep at night. And then, you know, and then you can't wake up in the morning. And then you're bitter. And then you I was snapping at my family. And I love them. Like I felt so bad about taking it out on them. And then, you know, my health deteriorated. I mean, I was a mess, John. So.

Yeah. Yeah. That was There was a bottom bottom moment for sure.

Can I ask you, did it shake your confidence in your ability to judge people? And And I say that because something similar happened to me. And it was it And I usually consider myself a pretty good judge of character. You know what I mean? Like But I'm blinded by friendships and and those type of things. And when happened that similar thing happened to me, yeah, it hurt in the business standpoint. Okay, you know, and it taught me a lot about, "Hey, I can do this cuz I can rebuild from nothing." Going from 6 million to zero. And having somebody take the company away, you know, a portion of my company away from me. But it what what hurt the most was Well, I think what for me it was the biggest thing I had to come to grips with was my ability to trust people. And because of cuz I had such faith in my judgment of people that it got shattered. And I had to then come to grips with that about me and how I and how I evaluated people, my judgment. But also just my level of trust in others. And it And that took a while That was probably the hardest thing for me to get back um from from that low point. So, did it Was it Was it more introspect Was it for you like, "Hey, you know, did it shake your confidence not only in your ability to start a business and do the you know, raise money and and that fun stuff, but your confidence in in I don't know if it was in trust as much as I think I was even lower in in the bottom. Like I think at that point like I don't even think I thought about trusting people. I think I lost trust in myself. And I think that's even harder because I didn't know if anything or anyone can help me out of my mess. And I think that that that just completely shatters every hope you have.

Yeah. So, how did you get out of it? How did you get out of that that that place, right? Because a lot of times Yeah, well, but I mean, was it was cuz I know from me it would for me there was a kind of a all right, John like stop feeling bad for yourself. You know what I mean? Like there was definitely a oh my God, I can't believe this happens. Woe is me for a bit and then it was just like all right, dude, you can only wallow in this for so long. You got to get after it again and and go. And it was a little bit of a kind of a light bulb moment for me Yeah. in a couple of ways. Was there there was there a moment where you said to yourself Yeah. Yeah. Yeah. There there's always these moments that define you, I think. For me it was actually like I think there was like a little cancer scare that you know, I was like and and I did lose my mom to cancer and I you know, I think that was kind of like all coming together and I was like During this during this time too?

>> know before but it was but it was one of those moments that I I kept wondering like what were her regrets and it like it was kind of like in my head and and suddenly like I'm getting this cancer scare and it's right when all my life is collapsing like and it's like it's incredible and I'm hospitalized three times. Like John, I'm a iron like I ran Iron Man. Like like I should not be collapsing on some health issues, you know? Like, this doesn't make sense. Uh but again, I you know, my lungs were okay. My life wasn't, right? Like, I was collapsing. So, but I think there was a cancer square and and at that point, like, when we were waiting for results, I said, "If this is it, I missed life." And that was such a hard thing for me and I was like, I'm still getting emotional from it. And it was just like, "I will never feel regret." Like, I I I feel it and I'm never going to feel it. I'm just going to freaking go. And that's it. Like, that was like the the end of it. Yeah.

So, but but you would have so much That question's a tough one, right? Because you say, like, if this is it, then I've I've failed at it. But you've been so successful, right? Like, you have won your first million. You've done everything, right, John? It's like I was going to say, like, you know, there's some people who haven't accomplished anything and and fall into that and and it's a self But then there's people that have objectively done extremely well in life.

>> We're so good about forgetting everything good that we've achieved and just seeing the horror of where we are. And I think sometimes that's what driven people do, right? By definition, I think I should have been further along, right? There's there's always this beautiful saying, um, you know, you always you know, overestimate what you can do in a year, but you will underestimate what you can do in a decade. And I think it's so true because we always as driven people, we always live with a little bit of like, "Ah, I should have I should have I should have." But that's what makes us driven. And then on the other hand, what what the problem with that is so many times we just don't take the seeds that actually build us, you know, the second part of our life, which is the decade. And you know, I think that was the moment where I was like, I need to freaking figure this out no matter what it takes. And eventually I did start a company, I sold a company, I'm investing in companies and mentor advisor. And that's what started the whole notion of where was this notion of portfolio career? Like why did nobody tell me did it exist? Anyways, so

Yeah. No, well, and that kind of brings us to leap, right? And and Yeah. Did was that was that low point for you? I mean, I mean, did you have When did you have the vision for leap academy? Like to take what you're learning and and try to help other people do this. Was it through that that recovery, if you will?

>> Um so that recovery, so that was all 2014. So in that recovery, um I actually um I made a promise that if I ever figured this out, I'll tell the world how, but I didn't really remember that promise, right? Like eventually and eventually like I realized that I'm leaping again and again, like I started a company, sold a company, I'm doing all these things, I'm being on stages, I'm investor in 100 companies. I'm like And I I remember it was like in 2019, um and I don't know the moment that, you know, I decided to experiment with it, but I actually start, you know, I do actually some people started coming up to me and asking me about their career. Now, I wasn't known for a career anything. I was known for a cloud, data center, engineering, like you know, like I wasn't known for any of this. And but suddenly people and this is great for our listeners, like people are intrigued by you by something. They're already coming to you for something. Listen to what it is, because sometimes we tend to just push it to the side because we're thinking, oh, this is just me doing some favor here and there. Oh, this is just me sitting for coffee. This is just No, this is actually a hint. And at some point, I decided, well, what if one of the keynotes I try instead of talking about investment or breaking barriers in entrepreneurship or all of this, I will actually try to talk about owning your plan for growth. And that was the seed for Leap Academy, if you will. Um and it was actually a hike, and I will never forget it, in Kyrgyzstan of all places, with my family. Um and I take them once a year to what I call a slap in the face, and I take them to a place that is clearly going to put them right back to this Silicon Valley is not the norm. So, we're walking, it's 2019, we're walking with my son. Um it's like like horrific path. I totally underestimated how hard this is going to be. Um like the mother of the year is not coming. The prize not not for this hike, for sure. But I'm and I find myself talking to my son, and I'm explaining to him why I'm, you know, passionate about this topic and why this is so interesting. And I'm suddenly realizing that I'm literally pitching him on why creating something like Leap is so important. And at the end of the hike, I was like, you know what, this is what I need to do. It was amazing. It was that hike that actually made me decide that, you know, I'm going for it. And and I think there's a little bit of accountability, right? Once you verbalize something, you just got to do it. And now I verbalized it to my son. Like I can't be the wimp that doesn't take action, right?

That's it. Nope, you got automatic accountability. I love it.

So, so let's talk now about that the portfolio and and how because right now we're in I I personally believe that, you know, I when I saw what Claude co-work, you know, I had the whole wake up. Three weeks ago, went from Open AI to to Claude co-work and I Uh, you know, the whole matrix, I know kung fu, right? Like I woke up, I was like, "Oh my god, I can do everything." And that was that was both insanely exciting for me cuz I was like, "Look at all I can do." But then I then terrifying because I I really even after a while, uh, you know, after Cloud got to know me and all the things, as I was going to bed that night when the unlock hit, I I came back and I said, "Hey, um, just out of curiosity, like realistically, you know, mid-market for me, like mid-market sales, you know, SaaS, how long do they have until they're irrelevant?" And it was like two to three years. And that's exactly what I thought. And I was like, "Oh, shit." And and so what I've been trying to do, and that's why I love what you're working on here, is is to do try to help sales reps future-proof their careers in the sense that I think it's almost, um, irresponsible. Now, as much as I, you know, I love capitalism in theory, but in practice it's brutal. Um, and and look, it's almost irresponsible at this point for a company leader not to look at AI to replace people because it's just that much better in certain things than than salaries and job security.

>> if they don't look at AI, of course. They're going to be 10x more productive, for sure. So, inevitably, the layoffs are going to come and all of it. So so people even good I mean, you look at Oracle, right? Like 30,000 people just hacked off with an email, right? Been there for 30 years, some people. Um, so how does somebody own their their career in such a tumultuous thing? And how are you positioning people to have that portfolio so they're not just a one-trick pony? Right? Because like if I look at an SDR, like if you're just an SDR right now, you're going to get smoked. But if you learn full-cycle sales and you learn how to develop relationships and partnerships, you might have a chance. So, how are you helping Yeah, that's a good sales professional, anybody, build their portfolio so they can be a lot more dynamic depending on where things are going.

>> a good question. So, first of all, the stats are staggering, but they're real. So, I like I said, I just came back from Washington, D.C. 92 million jobs will be displaced in 2 years. That's a figure. Okay? That That's a figure. I can send you Do you know what I mean? It's insane. And the only argument is if it's going to be 300 million after that in the next 5 years or it's going to be 600 million. That's the only only figure that they are not sure about. The 92 million is already sure. So, we are looking at a really hard time. The career ladder is burning. There's nothing that we can do. So, the only question is how does every single human become a massively adaptable, but also economy of one? And if you can become your own economy and start building these portfolio, now you can actually create, no matter what happens to the career ladder, you can stand on your own feet. Now, it doesn't mean that everybody needs to be an entrepreneur. Don't get me wrong. Like I think entrepreneurship is really hard. If you can have a job, amazing. But Yeah, on the weekend, at night, whatever.

Like do your own thing. Don't have your entire identity attached to that title or attached to that company. There's so many more things that you can do. And if you know sales, that's the most important thing in the like honestly, everybody will need good sales people. Like honestly, like every single one. Maybe you're going to So, get creative. Take percentage of deals. Get, you know, the affiliates. Like there's so many things that you can do. If you can do sales well, you're you're going to be unstoppable, but you're going to need to change the way you do sales all the time. And I think that's the hardest thing. Right? We're used to a very specific rhythm, but realize that sales is actually psychology of communication. If you know how to move people's minds, if you know how to influence, if you know how to negotiate, man, you are needed. Yeah. So that's it. Absolutely.

So, so with that, so how do you? What's the typical profile of someone that comes to the academy? Is it? Is it somebody with a sales background? Or like what percentage of them are are non-sales? Cuz I'm curious, sales is one of the the most, I think, misunderstood profession because there's a perception of what sales is, and then there's the reality of what sales is. And And I think that, you know, for the people that understand that sales is about problem-solving and, you know, those type of things, it's actually it's it's a lot easier to understand when think it's about slick sales stuff and whatever, they they run away from it. So for somebody who's looking at their career right now as like, "Hey, I don't have the gift of gab. I don't have sales." What do you? How you teaching them to build their portfolio here? What are the I guess what are the pieces of the portfolio here?

>> Yeah, yeah. So first of all, our audience is usually mid-to-late stage career. I don't really work with people that just came out of college, although they will need us as well, but it's just a decision-wise, like we just don't work as much with them. So our typical audience is 30 to to 65, if you will. Like there's We obviously have the 28 and we have the 72. But in general, like our sweet spot is kind of mid-to-late stage career. They already have a lot that they've done. Sometimes they forget how much they've done, which is me. And, you know, if you can go back to understanding what are those transferable skills and see what portfolio is even on the menu for you, that's where you're going to create something incredible. I think where it becomes really interesting is first of all to apply the 555 rule to test different things and what are the what can I do? The way that I like to look at it is there's a cycle in leaping, right? When you kind of look at yourself as reinventing yourself, the steps are pretty simple. I'm not saying they're easy to implement, but the steps are pretty simple, right? It's like, what do I want to do next? How do I align my story according to where I'm going, not where I've been, right? How do I open the right kind of doors because there's a big difference between the people that can open doors in a strategic way, and then how do I build a brand that not only I need to beg for every opportunity and open the doors, but things will start coming my way, right? So, the steps are really simple, and then you just immediately leap again and again and again. So, if you think about it as I just need to apply these four steps again and again and again, and now the question is what do I even want? What's on you know, and and sometimes it's about taking some advisory roles, sometimes it's, you know, helping, you know, people with some consulting and fractional work and coaching, and like there's so much on the menu these days, the only question then is what do you want? Now, the last thing that I'll say that I think has been really impactful for our people is sometimes, you know, you're afraid of looking too generalist to generalist, right? Like you're doing too many things, and one of the things that people miss is the concept of what I call an umbrella brand. And there's a way for you to look at all the different things that you're doing and stitch them into one big story. And it might not be as specific as I'm the CEO of Leap Academy, right? But for example, when I was debating and kind of playing around with do I want to like do I want to start Leap or I don't want to start Leap, and I was investing and I was working with companies, and I was doing these things, and I was like, so how can I stitch it all together? And eventually I just called myself a growth strategist, and it's not ideal, but it was like, you know what? That doesn't create a red flag on the startup the startup world. It doesn't create a huge red flag in the individual world. And it actually gave me enough of a confidence to step into that. And I think when you can actually make yourself feel better with some kind of an umbrella brand, even if it's temporary, as you build more um confidence and more evidence that you can make this happen, that creates like this massive um you know, like you you build that confidence and and then you can start narrowing down if if you need, so.

Okay. So, you talk a lot about brands. Um I've been talking about brand for a while. I built my brand not consciously, but just doing, you know, what I think is good work, sharing good people, you know, that type of thing, and authenticity, all the fun stuff. Um but the problem with brand and me trying to share that with other people and tell them to build is, you know, it's not a short-term thing. Yeah. It it's it's a it's a long-term play. And and so you posting on LinkedIn or doing something what people should think of traditional brand building of like sharing my thought knowledge and all that stuff. Um you know, they're like, "Yeah, but I got to close this deal. Yeah, but like I'm not going to get anything." Cuz likelihood of you posting something and getting somebody to say, "Oh yeah, let's do business." is not high. So, how do you how do you position brand and how do you justify it to people that say, "Uh Alana, I need a job right now. I get it, the whole brand thing, but I get kids. I got to pay the bills here. Me posting on LinkedIn or whatever is just not really I I see as a high value." But you and I both know that you started this with trust. Yeah. Trust is everything moving forward and nobody knows who to trust. So, brand is a big part of trust. So, how do you cross that barrier with people and how do you get them on that journey to start paying attention to their?

>> is a important question. Um so, first of all, it cost me a lot of millions to not have a brand. So, I just start with a story. You know, like I was trying to raise capital that you know in another time and you know, and I was coming to these investors again again again and eventually I was and and they kept wanting to meet me, but I was like, but where's the money? Right? Like John. You know, so um and eventually the partner there leaned in and said, "Look, Ilana, like we looked at like we really want to invest in you. We love your story. We look at you with we looked you up, but the truth is there's nothing. We Googled your name, there's like almost nothing comes up. We looked at your LinkedIn. At that point I had 400 connections. I have 40,000 now, but I had 400 connections. And he's like, "You're telling a story that we don't know how to how to latch on it unless we start calling, you know, all your connections." And I think it was the first time I realized like I was working on some like on somebody else's dream, but I completely forgot myself on the journey. And one of the things that I say today, John, is first of all, whether we like it or not in 2007 we became a media company. If nobody hears from us, the assumption is that we don't have anything to say. So, we can love it or we can hate it. It doesn't really matter, but it's an incredible way to control the narrative. Um so, that's first of all. The second thing right now specifically, especially when you're going to leap, like the shelf life of skills right now is about 2 years. It used to be 30. So, right now you going to whether you like it you going to reinvent yourself every year. So, your brand is actually a currency. This is what you have. So, it it's not a nice to have. It is a must have. Now, that I will say that you can look at it in a more intentional strategic way. You don't have to just spray and pray. You can, you know, kind of think about, "Okay, I'm trying to close this deal and it's not going to be immediate. Maybe I have some time with that, but I need to build some trust. Maybe I can look for a podcast that it talks about these kind of things and yeah, it's not going to be a popular podcast like yours. It's going to be somebody with some mom and pop. It doesn't matter. Look up to check out on Facebook, you know, podcast guests. You're going to see Brazilian podcasts that are begging for guests, you know, and and all you need to do is just reach out to the person that you're closing the deal and say, "Hey, I just spoke about exactly what I want to do with you on a podcast." Like I would love to sit for another meeting. You know, like just build like be more intentional about how you build it. I think people don't realize that there's like 20 ways to build your brand. Posting is one of them, right? I mean, you can get awards, you can write on Forbes, you can even do the you know, media, you can be on podcast, you can be speaking, you can be on panels, you can do a webinar, you can there's so many ways today that so be strategic with it of what actually going to get you to the results fast. Because I truly believe your brand right now is worth millions to you. So, you better figure out how to collect them.

Yeah, and it's the whole like what do people say with when you're not in the room? You know what I mean? Like that's what you always I'm always very conscious of that of like, you know, cuz cuz most of the time you're not in the room. Yeah, and if we're confused, everybody else is confused and they're not you're not getting the opportunities. Yeah.

>> No. All right, so let's finish on this one. You how old do you said you have a son? A son and a daughter, yeah. 18 and 16, yeah.

>> 18 and 16, so perfect ages right now to like what in the world to tell them, right? My daughter's 15. I'm curious whether college is even going to be a thing in 2 years when she graduates high school. Kids going into college right now, it's hard to look them in the eye and say, "Okay, in 4 years, whatever job you think you're going to have with this career is still going to be there cuz the like the strong likelihood is is it's not. So, knowing what you know at LEAP Academy, knowing what you've seen people go through the traditional um where are you right now with college and advice to kids who are getting into that part of their life that is going to it historically dictate what they do, but these days is a is a debate on is it worth it?

>> So, first of all, I think it's phenomenal. It's the million-dollar question right now, John. I think everybody is asking this. I do have a son in college right now, and the truth is it's probably a waste, right? Um now, I will say a few things. So, first of all, I am a big proponent for gap year, for traveling the world. I learned so much from traveling the world. It made me a better leader. So, first of all, I'm a big advocate for giving them uh freedom. But, again, at the end of the day, it's also their choice, and he chose college, right? So, first of all, I need to let that uh be. Um but, I think today and one of the one of the things that I tell my kids that at the end of the day, what matters is that you're going to be insanely proficient with AI, and you're going to find internship as fast as humanly possible. So, that's what he does. Uh he already had an incredible internship, etc. But, I will say right now what I'm looking at, you know, for for for kids or whatever, there's three really important I guess traits or skills that I want my kids to know. So, first of all, it is about adaptability. So, whether we like it or not, everybody is going to be average. And by the way, the people that are not even average, that don't even understand that there's more than ChatGPT on the line, like they're going to be in really big problem, right? But, even the people that understand that there is, everybody can sound average. So, how do you rise above the noise? So, first of all, like adapt to be you know, how do you get more adaptable? How do you rise above the noise? And then, yes, how do you think about yourself as kind of your own economy in this world? So,

Mhm. that's it. It's funny, I say the same So, I told my daughter, I'm like, "Look, I I do think there's value in the college in college, not from an education standpoint, but from an experience standpoint. You know what I mean? Like the like the just the social component of it. I think I I've always said that undergrad is much more of a social education than an actual education." Um so, there's something but what I told her is, "I don't want her to be dependent upon the degree. Like, I want you to have the experience, but I don't want you to be dependent upon the degree. So, let's let's work on some side hustle things. Let's work on some stuff where you can learn how to generate revenue. And then, go get your art degree. I don't care. Go get your psychology. I don't care. I I actually also want her to have the work experience. Like, I as as as twisted as this might sound, like, I want her to work in an office. I want her to sit in a cubicle and know what how shitty that is, right? Cuz cuz you know, you got to I I always say, "You got to know the rules before you can break the rules, right?" But, I don't want her dependent upon that that paycheck.

>> So good. So, so the adaptability to to figure out a way to create income some way, shape, or form through your own creativity allows you the flexibility to go get the college degree, to go get the job just for the experience purposes, not for the revenue from from the money standpoint. And I think that's the critical factor here that I look at. It's like, "Yes, go to college. Get a job." Those two things. But, but don't but somehow put your own self in a position where you don't have to be dependent upon those things. And it sounds like that's a lot of what you're doing at Deep Academy, which is your your putting people in a position to say, "Look, you know, you can't be a one-trick pony. You have to round out your portfolio so that you can adapt cuz there's nothing but uncertainty moving forward."

>> Yeah, I mean, even if you want a job, you know, like, what else can you build on the side? And if you just want to have your own business, amazing. But, how do you, you know, create a ripple effect? So, for sure. Yeah. Awesome. Cool. Well, I I got so many more questions and I I also know you have a book coming out called The Art of Leaping. Um you got LeapCon, you've got a podcast. So, tell everybody where they can find out more information. And also speak to the people that that might really be good fits for Leap Academy cuz I have a feeling that the people who are listening to this right now there's a lot of them that are in this kind of either already in a transition phase of their life because they've been forced to or are really thinking about it knowing that something's coming that they need to prepare for. So, I think I love it. And maybe we'll give your audience like a free entry to like a, you know, career leap challenge and we do kind of monthly like little, you know, challenges. Um so, we'll gift something fun for your for your own crew here. And but yeah, I mean, for me, if you're driven and you want more out of your career and you're debating whether it's multiple streams of income or maybe you just want a job for now and then maybe to assess what's next or you want to start your own revenue-generating business. Um but you know you want more. Um coming in. So, leapacademy.com. We going to have a gift for you so that you can join a challenge for free. Um and yes, I also have the Leap Academy podcast. We do focus on some of the biggest leaders of our time because I wanted to see their careers, right? Like the Richard Branson and president of Starbucks and president of Shopify and, you know, all the the founders of Airbnb and Zillow. Like I wanted to kind of understand how they make decisions so that you can copy from them and kind of understand like how you can create your own blueprint of a career. So, yeah.

Love it. Actually, I forgot to ask the I saw in you Were you on his or did he did Did you have him on your podcast? Guy Kawasaki.

>> Both. So,

>> he was on mine and I was on his. Yeah, yeah, yeah. So, I had him on mine and I will tell you right now it was when he came out with Remarkable. Um and I will tell you my audience probably sick of me hearing tell them the story, but I'll say it again. He That interview was when I knew I was in trouble. And the reason was is because it was it was about a year and a half ago when Remarkable came Think Remarkable came out and he had he had and I prepped for the interview and I'd done all and I'd watched his interviews cuz I hate asking the same questions everybody else always ask and in he had interviewed with Google and Google had just posted it 2 days before the interview. And he goes um and he said in the interview if you ask Kawasaki GPT a question, you'll get a better cuz he created Kawasaki GPT with all his books and all his podcasts and everything else. He said if you ask Kawasaki GPT a question, you'll get a better answer than if you ask me. So, the night before my interview with him, I interviewed him. And then I interviewed him and I asked him the same exact questions in the same exact order and I go, "Guy, at the end and I didn't tell him. I go, "Guy, I got to let you know, man, I've already had this conversation with you." And he goes, "What?" I go, "Yeah, your GPT, man." And I said to him, I go, "And I got to be honest, you were right." I go, "Your GPT your I got better answers last night than today." And he starts laughing and he was like, "Well, then why am I" cuz he had just come off of surfing, right? And he goes, "Why am I not out still surfing?" And I go, "Actually, Guy, that's my question." Cuz out of all this, the one I'm genuinely curious about is if I can get better answers from your GPT, what's the point of this conversation? Yeah. And he went into legacy and all this other stuff. I go, "No, no, no, no, no, that's for you." That's for you. For somebody like me who's trying to learn something from you, what is the point of this conversation? And when Guy Kawasaki didn't have a good answer for me on that question, I knew I was in trouble. Somebody who transfers knowledge for payment, right? I that moment, I'm like, I have to change everything. I I Not everything, but I have to adapt hard and fast because the days of somebody paying me for my knowledge that they can just ask GPT for People will not pay for knowledge, but they'll pay for transformation. Yes. And that's what you get in a podcast, and that's what you get from this conversation. Yeah. And that's And that's kind of where I've I've settled in on it. It's like, look, you can my all my I've been putting content online for 20 years. You can literally go on Chat GPT right now and say, "Coach me like John Barros." And it will. And And but that's not what you pay me for. And And so, it's that transformation. It's that mindset. It's that It's that kind of Yeah, accountability that you need. So, you know, I I hope there's I hope there's enough people listening out there that are willing to put in the work to to get better cuz, like I said, I I am very optimistic for those people that are. Um and I and I hope we can reach four of them to wake up a little bit just to your point of like that that getting out of that that that place that people are stuck in and realizing that the world is open right now if you just decide to go get it.

>> I mean, millionaires are always born at a time of change. You just need to decide if it's you or not. Then if it is, then go at it. Like, John, I love your message. Like, this is it, right? Yeah, thanks. So, Alena, thank you so much. This has been an absolutely fantastic conversation, and I hope more people listen to it and more people check out what you're doing and and the When is the book coming out?

>> Um in the making, in the making. I don't know yet. You're making Okay, all right. Well, when it does come out, come on back. Let's Let's talk about cuz I'm Is it cuz even if it's only like three or four months, I what's going to change in three or four months is pretty mind-numbing right now. So, I'm sure we'll have plenty more to talk about. Thank you, John. This is so fun. I appreciate you. My God. Awesome. Thanks, Alena. And everybody, hope you enjoyed the conversation as much as I did. Like I always say at the end of all these podcasts, go out there and make somebody smile today cuz no matter how bad your day is going or how bad you think it went, if you make somebody smile today, you know you had a good day and the world needs a lot more of that right now. So, thank you all very much and I will see you on the other side. Hey, thanks again for listening to the show and for all your support throughout the years. This is one last reminder to check out my training programs at jbarrows.com or leave a five-star review on your favorite podcast platform or G2 if you've already gone through my training or sign up for my newsletter. Any of those will help ensure I can continue to bring you free content and great conversations like the ones you just heard without having to annoy you with sponsors. Again, let's make it happen in 2026 together.