What Reinvention Really Takes with Ilana Golan

Welcome to Remarkable People. We’re on a mission to make you remarkable. Helping me in this episode is Ilana Golan.

Ilana is a master of reinvention and resilience. From breaking into new industries to building opportunities from scratch, her story is proof that change is not something to fear but something to embrace. She has inspired countless people to rethink what’s possible when life doesn’t follow the script. Her journey is a blueprint for anyone facing uncertainty and looking for ways to grow stronger through it.

In this episode, we explore how Ilana has turned setbacks into springboards for transformation. She reveals why adaptability is one of the most powerful skills you can develop in today’s world. Her insights go beyond motivation, offering practical ways to approach pivots in both work and life. Whether you’re starting over or simply seeking to expand your impact, Ilana’s wisdom lights the path forward. You’ll walk away seeing reinvention not as a last resort but as an essential step toward building a remarkable future.

Ilana’s story will challenge you to view obstacles differently — not as roadblocks but as invitations to evolve. Her candor about the challenges she faced makes her triumphs even more inspiring. By sharing both the struggles and successes, she reminds us that resilience is built in the moments we least expect. This conversation is about courage, clarity, and the willingness to take risks. Most of all, it’s about believing that reinvention is always within reach.

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Transcript of Guy Kawasaki’s Remarkable People podcast with What Reinvention Really Takes with Ilana Golan.




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Guy Kawasaki:
This is Guy Kawasaki. This is the Remarkable People Podcast, and we have a remarkable woman on today. Her name is Ilana Golan, and we're gonna talk about reinvention, and, well, actually a lot of things I'm gonna try to put her on the spot as much as I can. So just a little bit of background.
Ilana is a former Israeli Air Force flight instructor, and now she's the Silicon Valley entrepreneur, investor, and career reinvention coach. She founded something called the Leap Academy to help people reinvent themselves, and basically she empowers these people to change their lives. So welcome to the show, Ilana.

IIana Golan:
Thank you so much Guy. So fun to see you here. And we had you on my podcast, which was really incredible. And I've seen you for the first time in Startup Grind and you've been like a mentor idol since. So thank you for having me on the show.

Guy Kawasaki:
The first question I have to ask you is how did you become a F-Sixteen flight instructor? That's not your typical career path.

IIana Golan:
I guess not, but, oh, well, I'll say a few things. So first of all, in Israel we have a mandatory military service, so it was a little more typical where I came from. And after a few very hard tests, I somehow got into the Air Force, and they did this like very long almost pilot school type thing for us.
But again, at that time Guy, women were not allowed to become pilots. And that's important to distinguish. And so we did a lot of the training with the guys.
But at some point it was very, very clear that they didn't want women beyond the enemy lines and the only option that they give, and we were like a handful of women out of like hundreds of men, but the only option that was really open for us is to go be trainers.
So even though we studied, and we practiced on the plane, and we practiced on simulators and all of that, at the end of the day we could only be flight instructors. It was one of the most incredible roles that I can think of. I probably had at age nineteen, twenty more responsibility than I had at forty. And I learned a ton and I failed a ton. And it was an incredible ride.

Guy Kawasaki:
Wait, so I don't understand something. So you were teaching pilots, but you could not be a pilot yourself. So you've never flown a combat mission.

IIana Golan:
Never flown a combat mission.
Somebody broke the barrier. So right after me, an incredible lady actually sued the Air Force for not allowing them to. For basically not being able to have an equal opportunity.
And one of the cases that they took was that I became the first woman to ever become a commander in my squad. So I was essentially in charge of all the training of all F-Sixteen pilots in our squad and that was the first ever woman. So she took that case into court, and sued the Air Force and she won.
However, she won the equal opportunity, but she didn't get to be a pilot. And after her, they basically opened up the floodgates and now we have literally women pilots, women commanders. It's incredible. So I guess we all stood on the shoulders of people before us, and I'm really, really proud of that.

Guy Kawasaki:
First of all, since I very seldom talk to F-Sixteen flight instructors. Can you just give us the gist? When we all watch Top Gun and Maverick and all that, is all of that all bullshit or is that how it is?

IIana Golan:
It's actually so accurate. It's actually mind blowing. We were watching it when we were training as well. It's actually the simulator is spot on. Kelly McGillis, that was my role. So I don't look like her and I don't know if Top Gun Tom Cruise is there, but that was very similar.
So we were literally figure out kind of the mission, what the person didn't train on. We would figure out the mission, we were executed together. We would give them feedback. It was pretty much the same thing.

Guy Kawasaki:
Wow. I once flew in an F-Fifteen E, I hope that's the right plane. It's the plane where there's somebody in the front and somebody in the back.

IIana Golan:
Yeah.

Guy Kawasaki:
So I went to Elmendorf Air Force Base in Alaska, and I got a ride on that. And I'll tell you something, it is a life-changing experience to be in an F-Fifteen.
Now I gotta ask like very simply, what does it mean to reinvent yourself? You're the reinvention queen.

IIana Golan:
Yes, I think, and the way I was looking at it, Guy. I was leaping in my career again from Air Force to engineering to all the different roles in engineering, like tech sales and product and VP and now entrepreneurship. And one of the things that I realized is that first of all the things that I studied at age twenty, which is electric engineering, where is that now?
But really I kept needing to relearn things and I think the interesting thing is that we're going into an era that we are gonna need to reinvent themselves every year or two. People are not in the same place, in the same industry, in the same responsibility, same function for forty years.
That's gone. So we gonna need to reinvent themselves every year or two, and there's literally a system that works every single time. I just needed to get better at the same steps to start leaping faster and higher instead of getting stuck all the time. So it's been a life changing experience guy.

Guy Kawasaki:
But when you say reinvention, are we talking about fine tuning or to use a computer metaphor? Are we talking about reformatting the hard disc and purging memory?

IIana Golan:
It can be both, but maybe not purge the memory. But the way I would look at it is, so reinvention can definitely be. People put you in a box. I'll start over. Like people put you in a bucket, right? And if I was the geeky engineer, that's how what I'm known for and to now get people to see me as a leader.
That's actually a little bit of like how do I get people to see me as not just the person that will write the code, but actually the person that can lead. And then how do I get people to see me as the product? Or how do I get people to see me as of sales or marketing, et cetera.
So there could be also within your corporate, you're gonna need to reinvent the different responsibility, different functions, but also when you move to entrepreneurship or all the opportunities that exist today, advisory, board seats. There's endless opportunities. Investors, you've done a lot of these things.
There's endless opportunities. How do you get people to see you in that light? How do you get the opportunities that you want for yourself? So it could be a pretty big jump, but it could be also just a slight promotion and just going faster at the pace that you really think that is the best version of yourself if that makes sense.

Guy Kawasaki:
So if I understand this right, this is about reinventing yourself to take advantage of opportunities and take advantage of change but is there a concept of reinvention of you fundamentally.
Well, let's take an extreme example. Like what if somebody came to you and said, “Everybody thinks I'm an arrogant asshole. You gotta help me reinvent myself.” Is this like something you say, “No, I cannot help you?” Or, I'm being not exactly facetious. There are some people who should be reinvented from assholes. So what do you tell those people?

IIana Golan:
There's probably people even in our political environment that I probably couldn't reinvent them. But, I will just say, look, at the end of the day, I do believe that even people who are misbehaving or to some extent assholes, what you say, I think a lot of it has come from just not being happy with themselves.
And again, some people are born as assholes, like there's not much I can do about it, but I do believe that a lot of times we get nasty when we're unhappy. And I can tell you from my experience that if you want rags to riches or riches to rags story, I, at some point a decade ago, I almost lost everything I had in my life.
And, I was a fraction of who I could be. I took it out on my family. I took it out on everybody around me. And it was because I was not happy. And I don't think I was an asshole, but to some extent I was, like I was just grumpy. I was not happy with myself. I felt like a loser. I felt like a failure, and I needed to reinvent myself from the ashes.
So I think there's like sometimes if you are just starting to feel better about yourself, you're gonna be a better version of yourself and others will see it.

Guy Kawasaki:
Step me through the process. Gimme a linear like step one is this, step two is this, step three is this. Step four is this. Just walk me through how people do this.

IIana Golan:
Yeah, so the very first thing is that you wanna try to figure out what on earth do you wanna do with your life? The people that come to us many times feel like they should have been further on. They should have been further along. They should have more seat at the table. They should be more accomplished, and they don't know how and what.
And I think today with the endless opportunities, they don't even know, how do I even get started? How do I know what's even on the menu? And this was me, I had blinders on. All I could see is that director role or VP role that I wanted.
Like I didn't even know what are the options. And when you understand that there's more options, the first thing is to understand what it is that you wanna do. What do you wanna be known for? And that's sometimes really hard Guy, because we are wired based on what society expects and what people wants us to be and what's cool to be, and not necessarily what we really want.
So the first step is to understand. The second step is to start aligning your story with what it is that you wanna do next, because again, if I talk about all these cool algorithms that I'm engineering. Nobody's gonna sign up to Leap Academy. So I need to align my story again with complete integrity, but according to what I wanna be, not according to who I've been.
And once you align that story, now you wanna start having ambassadors that will bring an opportunity because the truth is Guy, and you know it better than all of us. All the coolest opportunities come from the hidden market, not on a job board. So if you want people to start seeing you not as who you've been, but who you want to become so that they bring you the right opportunities, how do you get that done based on personal branding?
How do you build, by the way, personal branding in the era of AI when there's millions of pieces of information? How do you rise above the noise? How do you get out of the people pile? How do you create those ambassadors to bring those opportunities? How do you close the opportunities? Et cetera.

Guy Kawasaki:
But what if you are dealing with a system. Yeah, I wanna reinvent myself. Why can't I be CMO or CEO or CXO or CTO, but it's all white males at that level. In my company, it's systematic.

IIana Golan:
Tell me about it.

Guy Kawasaki:
So, yeah, so now it may not be a matter of reinventing myself unless you're advocating gender change.
So now what do you do when the system is stacked against you?

IIana Golan:
So I live and breathe in a very male dominant environment since the Air Force. And then in tech, in engineering and VP, so I've been in a very male dominant all my life Guy. And the truth is I'm not gonna sugarcoat it. It is going to be harder for women.
I remember somebody meeting me. At that point. I already invested with pretty prominent big venture capitalists like Jason Calacanis and others, and my startup already raised capital from people like Oren Zeev and Oren Dobronsky, and you probably know some of them, et cetera.
And so I already raised capital. I already invested with people, and I remember somebody looking at me at some point. I was in some kind of a meeting, and I was on a panelist, and I was talking as the investor, and I remember he came to me, and he said, “That's so funny. I saw you in the park with your kids. I didn't even think of asking you what do you do?”
And the truth is, it's true, it is gonna be harder for women because the instinct, and it's not anybody's fault. It's not the men's fault. It's not the women's fault. It's nobody's fault. Like the instinct is not to look at me and say, “Oh my God, you probably a kick ass businessperson.”
That is not the instinct, and that's okay. It's ours to keep on breaking those ceilings and keep showing templates of what's possible. And to create those possibilities. And I think the more we are out there and the more we are breaking those ceilings, it's gonna become more normal. But it's also for us as women to tell the better story and to stop being ashamed and to stop trying to hide and to stop trying to be humble.
Because the humble doesn't open doors and personal brand does matter. So if you start creating that for yourself, more people will see you in that light, and more people will bring you opportunities.

Guy Kawasaki:
Okay, so specifically for women, I want to get the most tactical advice, how do I reinvent myself as a kick ass woman who should be in the executive suite?

IIana Golan:
It's a great question. So, one of the things that I don't like, if that's okay to say, is there's a lot of women's groups, and that's a very comfortable place to be. But guess what? The people that will get you in the room are not the women. So stop being in women's groups. That's not gonna help you.
You want the men to be your ambassadors. You want them to think about you when you're not in the room. And so you need to stop getting into those comfortable, oh, let me be in this women group and let me whine to each other. That's not gonna get you there. So what you really wanna create is that really kick ass brand.
And you want the guys and the men to see it because they're the ones that are going to be in the C-suite and the boards and the C-level, whether we like it or not. Now, the other thing that I will say is that there are very specific things that actually put you in an elevated place. If I get off of stage, of I was, I don't know, TechCrunch Disrupt, right? That puts you in a different stage. You've been on many stages, right?
The minute you get off the stage, you already are elevated compared to others, and it creates that pattern interrupt, if you will, for people to say, “Wait, wait, wait. I didn't think of her in that context. Why did I not think of her in that context?” Panels, podcasts, stages, whatever, like boards, advisory.
There's endless ways to present yourself in a way, like I mentored in some of the biggest startup accelerators like Google and Singularity University, et cetera, and just being positioned as somebody that can sit with C-level and move the needle on their companies already puts you in a different phase versus somebody that just raises their hand to another project in the company.
The more you can break the pattern of where people see you and where they put the template that they put you in, the more you can elevate yourself and get the opportunities that you deserve.

Guy Kawasaki:
Obviously many people think that the barrier for women is the masculine, the male mentality, but do you also think that women present a similar problem to other women?

IIana Golan:
Can I be honest?

Guy Kawasaki:
No, you got to lie.

IIana Golan:
I gotta be like really blunt here. Let's go. So sometimes I think women are more chauvinist than any men that I've ever run into. And if I'm being really honest, my podcast talks to the biggest leaders of our time and I cannot get the women to say yes. I talked to Richard Branson and Gary ‘Vee’ and you and president of Starbucks and president of Shopify, and like I can go on and on with accolades.
I don't understand why the men say yes and the women ghost me. I cannot understand that.

Guy Kawasaki:
Wait. So you're telling me that if you reach out to a female CEO, they ghost you. They don't wanna be in your podcast.

IIana Golan:
Again, I don't, as much as I like diversity and equality, I wanna put a focus, like I am not trying to lower the standards for women. This is not what I'm trying to do. I'm trying to get equal opportunity for women. And there's enough really kick ass women influencers, CEOs, that led big companies, or they have millions of followers, and we cannot get them to say yes to a podcast.

Guy Kawasaki:
Why?

IIana Golan:
I do not know. That's a great question Guy. So yes, I think that women are just as biased as men. So I don't think that it's one versus the other. I think we all need to break the templates of what's possible and to get more success stories and to put them more out there.
And again, it's all about pattern interrupts, right? Or it's all about patterns of success. And if women, right now in the average are not a pattern of success. You don't create that pattern in them. So I think it's normal. There's no blaming here. There's just about, oh great, how do we fix it?
And Leap Academy is fifty-fifty, our clients are exactly fifty-fifty. I don't believe in all men, all women. Bring it in. And it's interesting how it's pretty consistent for five years, it's fifty-fifty and we've been one of the fastest growing companies in America, private companies in America for two years in a row, fifty-fifty.

Guy Kawasaki:
If you're listening to this podcast and you're thinking, maybe I need to reinvent myself, is the primary signal that you are not getting your fair share of opportunities? Like what should be the signal that says, “Yeah, I gotta go get reinvented.”

IIana Golan:
I think you're not your full potential. When you're around forty, fifty, sixty, you know if you're full potential or you're not if you maximize everything that you want out of life and out of career and out of your status and, possibilities and impact. And, if you're living your best life, and I think, if you're tossing and turning like I did at three in the morning and you're like, I've been on this horse of success, why on earth am I not further along?
And you felt like you fell off this horse of success. Yeah. Let's go back on, because the truth is when you're more successful, you are happier, you're creating bigger impact, your teams are happier, your companies are happier. We're creating a better society, a better world. So yeah, let's get on with it. But I will say, Guy, it's for driven people.
If somebody has never been successful in their life. I'm not gonna make them successful. There's no magic wand. There's no get rich quick. There's no magic bullet.
There's just a very systematic engineered approach that I wish actually was taught in schools and colleges like I believe my son needs to learn because today adaptability and AQ is probably, which is essentially reinventing and leaping is one of the most important skills for the future work.
Why is this not taught everywhere? This should not be a proprietary, exclusive thing that is taught in Leap Academy. That should be, we should disrupt the whole professional education, which doesn't exist today.
Like what can you do? Go to an MBA? It's good. You get create connections but is this really the thing that will meet you where you are and take you higher? Probably not.

Guy Kawasaki:
Okay, so Ilana, I'm gonna put you on the spot.

IIana Golan:
Go for it.

Guy Kawasaki:
And I'm gonna to do some case study and analysis. All right? So, pretend that these people came to you or pretend that you're reaching out to them, offering your services for them to reinvent themselves for greater opportunity. So test case number one, Kamala Harris.
What do you tell Kamala Harris to do?

IIana Golan:
Oof. I think, the question, does she wanna go back to politics or not? I think the first thing is what does she wanna do? Does she really wanna get to the forefront, or she wants to write a book about it, she wants to now be a model for women that will wanna follow her, that she wants to create more of a name brand for her as somebody that did try to break the barrier.
She did raise a ton of capital. She did do an incredible campaign. Like I think there's a lot to learn from her. So I think the question is first of all, Kamala, what do you wanna do? And by the way, come to the podcast. Yes.
Well, if it makes you feel any better, I have not been able to get her on my podcast either.

Ilana Golan:
I feel a little better.

Guy Kawasaki:
Okay. So now. What if Benjamin Netanyahu came to you and said, “Help me reinvent myself.”

IIana Golan:
Get out of the government, dude.

Guy Kawasaki:
Get out of the government.

IIana Golan:
Oh my God. I think that Israel has never been in a lower place in its existence. And I do blame the whole government and mainly Benjamin Netanyahu for where we are as a country as what's going on with our neighbors. Again, he does what's known to be very successful in terms of leading by hate, and he creates a lot of hate inside Israel.
Honestly, I think the biggest problem with Israel is not even external. It's what's going on internal. There's so much hate right now going on, based on what we are doing out there in Gaza and other places, like there is so much hate going on inside of Israel that I don't know how easy it is to recover.
And he created that hate. And again, good leaders, quote unquote, know that they're gonna be more successful if they create a lot more hate inside their organization and he did a phenomenal work in us hating each other. And it breaks my heart because Israel was the startup nation. We were insanely proud of what we achieved.
I think I'm still very proud of what we created in a very short amount of time. Again, the Jewish population is what, fifteen million? We're eight million in Israel. We're actually six million probably Jewish people in Israel. Like it's insane what we created by, you know, two million Arabs.
Living in Israel was incredible coexistence. Which I think a lot of people don't understand. And my two best bosses in the world in Intel were Arabs. We live in coexistence in Israel. But what's happening outside is breaking my heart. But again, we are dealing with terrorists too, right?
Hamas is a terrorist organization. Like I wanna make sure that's very clear. And it breaks my heart where we are right now. So yes.

Guy Kawasaki:
This is somewhat facetious because this is not a person, but what if quote unquote America came to you and said, “We need to reinvent America.” What would you do?

IIana Golan:
I think it depends. Trump will say, “They want to ‘Make America Great Again.’” I say that too just in a different direction, but if I'm being really honest, I think that this very similar, maybe different outcomes, different circumstances, I think Trump and Benjamin Netanyahu have a lot of similar agendas in the sense of if I create enough hate, I will be able to stay in power.
So I don't agree with any of that if I'm being really honest. So yeah, that's not my type. I want people to be empowered and inspired to do more and to become their full potential, not to create so much hate that everything collapses. What do you think, Guy? I wanna hear you. What do you think?

Guy Kawasaki:
Okay, I'll give you the very general answer. I think that we should let women run the world and run most companies because men have been screwing things up for about 3,000 years. So why don't we let women have a chance? Because it cannot be any worse than what it is. I want every country, every company should be run by a woman.
I'm willing to roll the dice on that.

IIana Golan:
I'll roll it with you. Let's go. I think we do run it differently. So I think there's just a different approach. And I think the coexistence is beautiful. Like I think there's a lot that we get from men. There's a lot that we get from women, and the more we can really lean on equal opportunity, the better it is.
But the truth is again, we need men to help us get in the rooms, get on stages, get to the board seats, get to the advisory. It's very, very hard to get there on your own. So we actually need you guys to help us.

Guy Kawasaki:
I might make the case. All you need is the Y chromosome. You don't need anything else, but that's a whole different discussion. So, when I was preparing for this interview, I thought, well, let's see what AI would do with reinvention. Okay? You're gonna love this.
So I went to ChatGPT, and I said, “How should Elon Musk reinvent himself?” Okay. All of you listeners, I suggest you do this too. It is the most fascinating thing. So I'm gonna read you basically the answers of ChatGPT. I asked it, “How should Elon Musk reinvent himself?” So, point number one is lead with humility instead of provocation.

IIana Golan:
Ooh.

Guy Kawasaki:
Spot on. Second bullet, replace chaos with consistent execution. Two for two.

IIana Golan:
That hurts.

Guy Kawasaki:
Three, rebuild trust with transparency. Three for three. Four, empower others to lead.

IIana Golan:
Slam dunk right there.

Guy Kawasaki:
Okay. And the last one was bring more empathy to the mission. I don't know how you can claim that ChatGPT is not sentient after you read that answer. So now I read that answer. I said, “So Guy, don't be a chicken shit. If you're willing to ask about Elon Musk, why don't you go ask about yourself?”
So I asked ChatGPT, “How should Guy Kawasaki reinvent himself?” And I'm gonna tell you the answer. The first answer is shift from evangelist to elder. Okay.

IIana Golan:
Ooh.

Guy Kawasaki:
Second, build a school of thought, not just a podcast. Ooh, hurt me. Number three, lead into radical candor. Now this one, I'm not so sure I need to reinvent myself to this.
I'm pretty radically candor already. Yeah, I think I can check that box. The fourth one is focus on post achievement mission. I forget who I stole this from. But I stole it from somebody smart. I used to tell people that there's three stages of life.
First you're underpaid and overworked, and then you're overpaid and underworked, and then you pay back. And I used to tell this all over and then I heard somebody say, “There are three stages in life. First you learn, then you earn, and then you return.” And I thought, that is so brilliant.
So now I say that, and if you're the person who's invented those three terms like that, my hat's off to you. I don't know who did it. One of the things I learned from Steve Jobs is you gotta know what to steal. I hear a lot of things. I don't steal that many. Okay, so now, and then the last thing it said for Guy to reinvent himself is to turn Signal, the secure messaging app, turn Signal into a movement to help society.

IIana Golan:
Wow. Okay.

Guy Kawasaki:
And I gotta say, I was so blown away I got in touch with Madisun. Madisun, let me tell you what it said I should do.
But for those of you who are curious, I'm telling you will be fascinated. Go put anybody's name in there and see what ChatGPT says is necessary for reinvention. And if after you do that, you don't believe ChatGPT, I give up.
It's not my problem at this point. Now are there any cases where you tell people, you know what, you should be comfortable in your skin? You don't need to reinvent yourself.

IIana Golan:
I don't know if it's, you don't need to reinvent, but I did tell people that it's not the right time. So I remember there was somebody that came to me, she was eight months pregnant or seven months pregnant, and she's I need you. I need you. I'm not happy where I am. And I'm like, you know what?
Things change once you have a baby. It was her first. And I'm like, have the baby wait three months and if you still think that way, let's come back. And she did come back. But I think, in terms of timing, the timing does matter. And I think there's also an element of do I actually have the capacity to really do the work.
Again, there's no magic bullet. There's no magic wand. There's just very engineered process and it starts with defining what you want. And again, that sometimes we don't know what we want. And if you have a very big life's change, that will change.
Again, life is in phases, different phases bring different things from us, and you called it learn, earn, return, but I think it's like even every few years it changes.

Guy Kawasaki:
Ilana, you just opened up a massive door right then, which is, so here is someone talking about reinvention, and she brings up an example of a woman getting pregnant and postponing her reinvention.
And that's the problem, that you would never say to a man, well, not that men can have babies, but you would never say to a man, you are expecting a baby, you should postpone your reinvention until three months after your baby comes, right?

IIana Golan:
It's definitely gonna change the women’s view on life and priorities a lot more than the men. That's true. That's just realistically true and I just wanted to make sure with complete integrity that she still wants more.
Because the truth is, let me be honest, Guy, like the first two years of my kids' life, it was very comfortable to be in a place where I could create probably one PowerPoint a week, and I was considered a star. Let me tell you. It was comfortable. I was sitting close to the kindergarten, again, I was very dedicated, I was very hardworking.
But at the end of the day, my priorities were definitely a mix and I'm not gonna lie about it. But I will say that when my second one was five months old, I got sick and tired of my career being on hold. I was just like, what on earth did it happen? Let's go.
And I went all in on work.

Guy Kawasaki:
So you're telling me you started to lean in?

IIana Golan:
I started to lean in all the way. Yes. Maybe a little too much if you ask my husband. I left home for about seventeen years of work. But yeah, it bothered me that I put everything in the backseat for so long and I wanted to go up to be all in again. Yeah. And to create the possibilities that I knew I deserve.

Guy Kawasaki:
Let's take it as a given that in the process of your life, you will have to reinvent yourself. Okay, so now knowing that you have to reinvent yourself at least several times, what would you tell young people to prepare yourself for this so that when you have to reinvent yourself, it's not nearly as hard or slow?

IIana Golan:
Oh, such a good question, Guy. I'll say a few things. I do think that a level of adaptability, call it learning, call it adapting, call it being very agile. Curiosity, like these things will matter. I will say that one of the things that blindsided me is the personal branding piece.
I did not think of building a personal brand. I gave a thousand percent or more to the company that I was with. I was flying all night. I was doing all the things. And I still remember it was actually a very humbling experience. You'll appreciate that Guy.
But at some point I was raising capital and I remember going to the same investor a couple times and I was like, what else do you need to see? Because clearly, I'm coming here again and again. You are giving me your time. But what are you missing? And they're like, look, Ilana, the truth is we're very impressed with what you're building, was very impressed with you.
But we Googled your name, we checked you on LinkedIn. You're non-existent. We don't even know how to validate this type of information. And at that point, it was heartbreaking a little bit. Like I could give them the phone numbers of the boards that the companies that I was with, right?
But I was like. Why did I not build anything? There was nothing Guy, there was no Instagram, there was no Twitter, there's still barely, LinkedIn barely existed. I was like, why did I not build myself on the journey?
And the truth is, and I was impressed with you of how you leaned into building that personal brand and creating that evangelist when it was really early on, like people didn't even understand the power of it. And I completely missed the boat on it. And now I will say to anybody young, the only thing that will help you leap again is your own personal brand.
That's the only insurance policy you have. So build it.

Guy Kawasaki:
Ilana, to be honest with you, if during that process when you came to that conclusion you needed a personal brand because of this interaction with this VC, if we knew each other back then and you called me up and said, “Guy, what's your advice?”
I would tell you that VC is an idiot because, okay, so you're telling me that when they could fund Mark Zuckerberg, they said, “Oh, Mark, we looked you up on LinkedIn. You weren't in LinkedIn, you didn't have a Twitter. Oh, how about Steve Wozniak? Oh yeah. He didn't go to college. How about Steve Jobs? We looked at his LinkedIn. Oh, attended Reed College one year.”
So all these people who have been very successful, you could make the case that none of them had personal brands. So that's one thing I'll tell you that VC's an idiot, but that's a redundant statement, VC idiot.
But anyway, so the next thing I would tell you is that people think that Guy Kawasaki has this personal brand. And to some extent that is true, but if they think that I consciously built the personal brand, they would be wrong because I have this theory that a personal brand is not something you build.
It's something that forms organically and the way it forms organically is you do good shit. So the way to ultimately build your personal brand is to do good shit and everything falls from that.

Ilana Golan:
We don’t agree on that, but let’s go.

Guy Kawasaki:
Oh, that's okay. But like I refuse to believe that Jane Goodall or Steve Jobs, or Neil deGrasse Tyson, or Stephen Wolfram, or Margaret Atwood, ever sat down and said, “How can I build a personal brand for myself?”
I don't think that discussion ever happens.

IIana Golan:
I don't know. And I'll be really honest. I think that first of all the era changed. So, in 2007 we all became a media company whether we like it or not, and that was not the case previously. So previously you needed to work really hard, and eventually somebody would see your results and somebody would write about it in the press and it would be really, really cool.
The times has changed, and the truth is if nobody hears from you, the assumption is that you don't have anything smart to say. But it's also the best, the most incredible way to control the narrative. And I'm not saying talk about things that didn't exist, but I'm talking about being very intentional and very strategic with how you position yourself out there.
And I do believe that right now with the world of influencers, et cetera, there is a big play there. And if you're not leveraging it, I think you are leaving a lot of money and a lot of opportunities and a lot of impact on the table.

Guy Kawasaki:
How about we agree that there is not a singular path to success.

IIana Golan:
We do agree on that. But again, I look even at Richard Branson or others, I don't know if he meant to do all these adventures for personal branding. But that became his personal brand. And it's very intentional, right? You do need to get outta people's pile, whether we like it or not.
How do you get out of the people's pile? So one option is to be part of really cool companies, right? That really helps. Some of it is to be born to fame, but if you're not any of these and you're like me, came from a small village in Israel and trying to win your place here and to create something for yourself in a network that doesn't exist in a language that is second language, et cetera, you do have to do a little more than the average.
And just working behind the scenes away from the spotlight is not gonna get you there.

Guy Kawasaki:
My last question for you, who is in the Ilana Golan Hall of Fame for personal branding or for reinvention? Who do you hold up as a this is what you should do, this is how you know you can change your brand or reinvent yourself? Who's the hero in your book? Who's in your hall of fame?

IIana Golan:
Wow. That's a beautiful question. I think it's everybody that has been on my podcast, there's a reason why I approach them, because each one is inspiring me in a different way. You inspire me in one way. Richard Branson is the biggest mentor for me. I think what Sahil Bloom did in such a short time and built such an incredible brand for himself very fast is incredible.
So I think each person inspires me in a different way. I love what I get to do, because I get to just witness those changes in people as well and just create that for thousands of people a year. And I think that's just incredible to watch.

Guy Kawasaki:
I'm gonna tell you my favorite Richard Branson story.

IIana Golan:
Tell me.

Guy Kawasaki:
This must be fifteen or twenty years ago. And he and I were both speaking to the same conference in Moscow.

IIana Golan:
Fun.

Guy Kawasaki:
Which I'll never go to Moscow again. But anyway, so he and I were in Moscow, and I go into the speaker ready room and I'm sitting there and then in comes Richard Branson. Someone introduces me to Richard Branson and I never met him before. I didn't know him, but apparently he knew of me.
And so he says to me, “Guy, do you fly on Virgin?” I said, “Richard, I am Global Services on United. I fly only United. I don't wanna lose my Global Services status.” And Ilana, I swear to God, he drops to his knee, he lifts up my shoes and he starts polishing it with his sleeve.

IIana Golan:
That's so Richard.

Guy Kawasaki:
And that's the day I started flying Virgin America.

IIana Golan:
The best story.

Guy Kawasaki:
Yeah. Richard Branson. I should have him on my podcast.

Ilana Golan:
He's an incredible human. He pushes me to my core for sure. He makes me swim and bike and, yeah. Anyway, he makes me do things that are incredible.

Guy Kawasaki:
All right. I am going to let you go. And go help other people reinvent themselves. I thank you for being on my podcast. This has been most interesting.

IIana Golan:
Thank you Guy. Go surf and go do shit.

Guy Kawasaki:
Literally, I am gonna go surf right now.

IIana Golan:
See, I knew that. I already know you.

Guy Kawasaki:
You can tell from the time we record podcasts; it is never when the tide is low. Because where Madisun and I surf, the best time to surf is low tide. So my entire schedule is built around the tide. Seriously.

IIana Golan:
I love your schedule, Guy. You're living the dream.

Guy Kawasaki:
I'm reinventing myself as a surfer. How's that?

IIana Golan:
See that's something.

Guy Kawasaki:
Thank you Madisun for being the co-producer with Jeff Sieh and Shannon Hernandez on sound design and Tessa Nuismer on research. This is the Remarkable People team. Ilana. All we wanna do is help people be remarkable. So until next time, Mahalo and Aloha.

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The post What Reinvention Really Takes with Ilana Golan appeared first on Guy Kawasaki.