#349: The Top Tips To Overcome Fear With Your Favorite Guests Best Of Episode: Andrew Metz, Kelly Roach, Sara Blakely, Jesse Itzler, Wendy Smith, Maryann Lewis, & Uri Levine
4 Nov 2025 · 52 min
Heather Monahan compiles advice from Kelly Roach, Uri Levine, Wendy Smith, and others on overcoming fear and failure. Kelly Roach discusses closing the perception gap in entrepreneurship. Uri Levine explains how small wins build momentum toward your next opportunity.
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Everyone knows we have to experience moments of failure to get to the success we so desire. But how do we actually manage the failure, not give up because of the failure, and know the difference between a misstep that we can grow from or when it's actually time to tap out? I've talked about the topic of failure many times on this show and in my life and if you're having this experience right now or struggling with the idea of confronting failure at all, then I've put together a handful of the best pieces of advice from some of.
My most successful guests who who not only know the experience of failure very.
Well, but will share with you their tactics to treating it as a valuable part of the process, including yours truly. I know this one's gonna help you. If you like this episode, please leave a review, share it with someone that it can help. That way I know I'll create more of em like this.
Let's go meet a different guest each week.
What I found and maybe this is just me being brutally honest throughout process but I think because I've had street credibility of my organization going through the ranks, I started as a BDR for.
People who don't know what a BDR is. Can you explain that?
Business development rep or might be known as a sales development rep but that's a fancy term for cold callers. As I like to tell people that enter the org I say my first year I made cold calls and cleaned the toilets, which is partially true. And I've always had a lot of confidence in what I was good at. And that was originally cold calling and then I, you know, sold for my organization. Then I was a frontline leader and a second line leader and so on and so forth. But I also was never afraid to admit what I didn't know. The real buzzword out in the LinkedIn world is vulnerability right in the last couple of years and I think I was doing vulnerability before it was cool. It was just my way of not over promising and under delivering. I wasn't going to tell someone I knew something that I didn't know. And the thought of imposter syndrome is simply the feeling that you're unworthy or you don't exist and everyone has that to some degree. I have that talking to you right now, right? It's like what can I bring to Heather Monahan's world? So I certainly appreciate the opportunity. But there's also a voice inside of all of us that should encourage us to dampen that. Because when you get that imposter syndrome feeling, it really means you're out of your comfort zone. It means you're doing something you haven't done before. And usually when we're proud of an accomplishment or an experience we had, it was something that was uncomfortable initially and we look back on it going, hey, I wasn't sure if I could do it, but maybe I failed or maybe I succeeded. But either way, you got to give yourself credit for taking the shot.
Well, just your own journey, right? Starting out as someone jumping into the cold calling world, which, P.S. hey, I've been there as well. You know, I'm sure on day one, you weren't the best cold caller with the best closing rates, you know, out.
Of everyone, of course. And that's part of it is having the thick skin to take the rejection and really being okay with failing. Looking at failure as the opportunity to learn. Right. The cliche is it's not what happens to us, it's how we respond. But that's true in a lot of cases. And, you know, sales is a good microcosm of life where you're going to go scrape your knee a little bit and it's how do you, how do you react? And are you going to change your approach next time based upon what you learned? And from that, you build confidence from there to approach it differently the next time. And you also figure out that failure is not as scary as people think. Right. People are embracing for, oh, God, how bad is it going to be? Or the rejection. And once you find out that the show goes on the next day, it gives you a little more perspective to have more confidence to take more risks.
So true. It's like anything, the more times that you're at bat, the more comfortable you're going to get when you step into the batter's box. It is no different with failure, although I definitely had a very different opinion of it, you know, when I was back in, quote, unquote, corporate America. But I want to jump in a little bit more to the imposter syndrome to hear your thoughts on. My experience with imposter syndrome was I remember I was advocating for myself to be promoted from executive vice president to chief revenue officer. And I remember thinking, am I even qualified for this? You know, I don't have a master's. I'm younger. Back then I was Younger than the other people, you know, at the scene suite level. I didn't have as many years experience in the company as they did, so I second guessed myself. But there's something probably from the competitive nature of who I am that pushes myself into these situations, even though I don't know if I'm qualified. So there was always that trepidation and fear, what if they actually say yes, then what? And so they ended up saying yes. And I'll tell you, this was a game changing moment for me, Andrew, was when I finally was appointed to the C suite position and my first big executive meeting as a C suite executive. I realized, wait a minute, this is the biggest scam going. I get paid more, I have more resources, I have more autonomy and control. Wait a minute, it's easier at this level. It truly was, it was actually easier and it is the biggest scam going. And so that's one thing I want to impart on everybody. I was so wrong. I was overqualified for all the reasons why I thought I wasn't because I was bringing my unique skillset to this table that needed it, desperately needed. And I was actually already doing the work just with a more junior level title. So a lot of this stuff is just, it's not real, it's built up in our minds. I asked you to try to find your passion.
I think that in the world of online marketing and with social media, you know, obviously online entrepreneurs use social media to promote their brand and to grow their business. And so obviously the focus and the goal is to show how well you're doing, to talk about what's working to show, showcase all the highlights of your brand and of your life and of your business. And that's great. And it works, right? It works for all of us. But you know, as our company went from seven to eight figures and I began to realize, like, okay, like I play a role in the conversation that is happening in the online space. I have a responsibility to actually let people know what it takes to build an eight figure business, to run a team that is, you know, spanned across the United States and serve thousands of clients and all these things. And I kept hearing all of these online influencers and course creators and people that have a huge voice in the online space saying, you know, it can be easy, it's going to be so fast, you know, you can do this overnight. Like, you know, and I started thinking to myself, I couldn't imagine if I was a new entrepreneur that was coming up today that was working really, really hard to build my business. And it wasn't happening overnight, and it wasn't easy, and it wasn't happening at hyperspeed, and it felt a little stressful along the way. And I really put myself in the operating reality of what is the experience of the online entrepreneur. That's not yet where we are, right? We came to the other side. Like, I already fought all the battles and went through all the scars and the wounds and made it to the other side. But how many entrepreneurs are having depression, anxiety, thinking about quitting their businesses, wanting to give up? Because the perception online is that it's easy. You barely have to work. This is going to happen overnight for you, right? We all just hang out in our Lambos and in our private jets and sit on islands. There is really no work to be done. We actually can't find anything to do with our time because it is so easy, Right? So I just realized, you know what? I am going to do something different here. I'm going to be a truth teller. So I just started, like, two and a half years ago really talking about, like, what the true experience of entrepreneurship is and telling stories of, you know, just mistakes that I've made and failures that I've had and struggles and setbacks. And, you know, I feel like when you have a voice, you have a responsibility to use that voice for good. And I do use my voice for good. Obviously, I help people build wildly successful businesses. That's what I do for a living. But there's a whole nother piece of that, and that's the human element. And so I just want the people out there to know, like, when you see Heather, you know, and Heather, you talked about this on my show, right? And when you see people like me that, you know, run these companies and are having this level of success, like, pure failure. Like, pure failure on the way to that success. Like, so many mistakes. So many mistakes, so many setbacks, so many moments of doubt. There's been so many times where I've shared publicly, like, a big goal that I was setting, and then afterwards, I'm like, why? Like, why? Can I put that back in my mouth?
Why.
Why did that just come out of my mouth? Like, it just accidentally. Because I was so passionate, I, like, said the thing out loud that no one was supposed to hear because I didn't know how to do it right. So, yeah. So, I mean, I think the big thing, I just want entrepreneurs to know, as you build your business, that if it's going a little slower than you thought it would, or if it feels hard or you're dealing with some stress along the way, that is you building the muscles that you need to get to where you want to go. You're not doing it wrong. You're not failing. You're actually right where you need to be, learning the exact things that you said that you wanted to learn so that you can get to where you want to go. And I just want to keep repeating that message over and over again because, you know, having crossed that bridge, what I'm seeing now, because I do coach so many people and building their businesses is it's actually a perception gap that is killing so many businesses right now. And it's the perception of what does it take to be successful versus what it looks like to be successful. And I believe that if we close that perception gap and people understand the amount of trial and error, even with mentorship, even with coaching, businesses can't be built in theory. They can only be built on the field, in the trenches every day. And I think if we're able to close that perception gap, I think many more people are going to their dreams come true. And that's what my goal is.
You know what's interesting to me about what you just said, and I'm really curious how you're going to answer this. In my opinion, there's a big difference between working with someone, a hypothetical client, right? And they're saying to you, kelly, this isn't getting off the ground. I'm trying so hard and it's not working. And you're cheering them on and trying to get them to work through these low moments, like you're saying that you had that I certainly have had. For me, the pandemic was like the biggest low moment ever. My business got crazy, crushed, and disappeared overnight. So we've all been in these really delicate moments where you do consider giving up. You do say, do I trash this business and start something new? What is that difference between someone who's just way off the market, it's not going to work, or versus, hey, you got to grind this out and push through?
Yeah, that's such a good question. So I think that there's a difference between what we want to sell to someone versus what someone is interested and willing to buy. And that is a huge distinction that I see a lot of people get stuck in. They'll say, I see that this group of people really needs ABC X, Y, Z. Well, guess what? If that group of people really needs ABC X, Y, Z, but they don't give a crap, and they're not willing to spend their money on it, and they're not interested in solving that problem. It doesn't matter that the problem exists. It doesn't matter that your perception of the problem is that it needs to be fixed. All that matters is is this a problem that that group of people is both aware of, invested in correcting, and willing to put their money behind. Right. And so I do think, Heather, that there is times where people's passion or heart gets confused with actually making a match between market viability and desire to sell something that people are willing to spend money on. And that's where I think it's really important. You can take your passion and, and you can apply your passion in a thousand different ways. You need to make sure. And that's actually why I'll give a specific example. I started the Human Family foundation because I really wanted to do something to give back. And I really wanted to make a meaningful difference by creating an entity of my business that was very focused on service and philanthropy. I see a lot of business owners that they say, I really want to give back. I really want to make a difference. So they start selling to a population of people that they're dead broke. They're never going to be able to invest in their products, programs, or services. They don't have the right mindset. They would be so much better off saying, this is charity and philanthropy. This is my business, and my business can fund me doing good in the world with this thing. But trying to take blood out of a stone with a population that doesn't. They're never going to be who you want them to be. Just because you want to feel in your heart that you're doing something good. It doesn't work out for for them and it doesn't work out for you.
Meet a different guest each week.
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The one thing I needed that we all need is we need a story. We need momentum. People buy into stories and momentum more than they buy into products like we're the Business Plan and When I started out, I started out in the music business. I had a record out on a label called Delicious Vinyl and right when my album came out I did Club MTV which is a big show on MTV. At the time I was 21 years old and I thought, like, wow, man, Mom, I made it. I'm on mtv. This is unbelievable. And I did my first show in Pittsburgh, and I got off the airplane in Pittsburgh, and when I got off the airplane, there was a huge newsstand, and on the COVID of this big magazine called Rap Pages at the time was my picture. And I'm like, holy shit. I'm on the COVID of Rap Pages. And I'm like. I'm like, this is unbelievable. I was like, being like, Forbes Visara. Like, I'm on Rap Pages. And I go and I get the magazine and the COVID of the magazine with my picture on it was, are white rappers ruining hip hop?
That wasn't heard this story?
Why would I tell you what? They married me.
So.
So I needed a story. I needed a story. So for me at that age, you know, it wasn't about when I had an idea telling people. It was about getting momentum. And I went to the New York Knicks with an idea to do a theme song for the knicks. I was 22 years old, and I said, you know, sports is changing. People sit in seats for three hours in an arena, but the game is only 48 minutes. So you have to entertain him for over two hours. Let's do a song and a video, and we'll get all the celebrities in New York. The song was called Go, New York, Go. And the knicks paid me $4,000 for the song. And by the time I paid the studio, the engineer, the singer, the producer, the drummer, it cost me $4,800 to do the song. So is that a good business model?
No.
Right. They paid me 4,000. They paid me 4,000. It cost me $4,800. You guys think that's a good business model? Wrong. That's an amazing business model, because I would have paid the Knicks, right? I would have paid the Knicks $5,000 to do the song for them to help me get to point B faster. Because now I had a story, and I could call up the Bulls and be like, I did the Knicks song. And every team that came into Madison Square Garden was like, why don't we have a song like that? And that was what really jump started my career. So for me, it's like, how do you get from A to B the fastest?
And then you wrote and produced a song for the NBA that actually won an Emmy.
I did.
And then you created a company, another company, out of this concept, Right? So it actually was a good business model losing $5,000.
Yeah, well, I mean, we figured out the business model after that. It wasn't sustainable, but it got me in the door and it got me momentum. And you know, I always tell people that ask me if they're stuck, if they're overwhelmed, small wins. Just, you know, even in this race I just ran, we all go through this period in any part of our journey where we're overwhelmed with self doubt. Anybody, no matter what you're doing, as a parent, as an entrepreneur, as a marketer, someone's bad. I'm not good enough. I don't have what it takes. Whatever we go through this period of self doubt, I had it in my race. I started off, I was like, couldn't run four miles. And once you get momentum and you start to believe and you can, you can have something that you can build on that's super powerful.
I mean, I would say to add to that, I recognize that the two biggest fears that we all have as human beings are basically the fear of public speaking and the fear of being embarrassed. And so I want that to lose itself power over me. So I will intentionally embarrass myself or I will intentionally find scenarios where I'm not good at something and then I go through it and it usually ends up making me laugh or if something ridiculous happens to me, I am, I immediately want to share it with people because then I start to find that it loses its power over me. And then you also find that when these things happen, if you can make somebody else laugh or smile, then it was, wasn't all in vain. And that's where real human vulnerability and connection happens. Especially even with your customers. So I learned that from selling fax machines. I mean, anytime I tried to act perfect or put on the perfect pitch, I got kicked out time and time again. You know, if I walked in and was like, look, I'm, you know, I'm nervous. It's hard for me to walk through your door. I'm sorry. I know there's no soliciting sign. I mean, I would get farther with that. But just calling out the humanness and the real of what we're all dealing with and not, not being afraid of it. So we do that at Spanx too. We have oops meetings at Spanx where we have the whole company get together and we stand up and we share what we failed at or an oops or a mistake that we made and everybody claps and it's just like diffuses it.
I ask you to try to find your passion. So I do some executive coaching. Not a lot, but I have a select few clients. I work With I try to keep it only to under five clients a quarter that I work with. And two different things happened with some clients in the last month that I wanted to share that I thought was interesting. One, and I've talked to you about this before. There is no place for emotion in business. None. That's taking us back to the woman that fired me. It was completely emotional. Her stock got crushed. And you know, it's just, it's hard when you make a decision based on emotion in business. You will live to regret it. So when someone gives really constructive feedback and it's harsh, sometimes people have a hard time swallowing that pill. Right. I've talked about that on the show before. You know, I've had people somewhat attack me, but you know, say, hey, I'm not attacking you, I'm just giving you feedback. But maybe not position it in the best light. And it's a little painful to swallow that. Well, one of my clients had been running around at the holiday time, 9 million things going on, end of year going on, and a big meeting was coming up and she delegated a lot to her team and whatnot. And come today of she realized she hadn't gone through the paces and checks and balances that she normally would, which happens to all of us sometimes, right? You know, no harm, no foul. And she goes into the meeting and this was a really high profile potential client, not yet a client. And she sits down to make the pitch, which she's done a million times, and she's incredibly successful and brilliant and she starts leading the meeting and the client or potential client stops her and says, well, what about this? You haven't mentioned this. When she did the overview of what they were going to cover and she didn't have what he was asking for. So right there she realized, wait a minute, we didn't qualify correctly on the front end. Right. So going into anything. For example, I'm giving a keynote tomorrow for an MLM company. I qualify ahead of time 9 million times. Just want to make sure that we're on the same page. What is the end result and goal that you have in mind for my keynote? And I had her articulated again. Heather, I want my team motivated, inspired, and I also want them to have tactical tips around social media promotion and tactical tips around sales and sales drivers. So I've written that down 800 times, so I'm crystal clear so I can deliver. My client realized that in all of the hurry and hustle that she had going on, no one had actually had that conversation. So I'm asking you right now for any clients that you have, any business that you're working on, make sure to qualify it first. You know, get clear on expectations on the front end. That's the most important thing to do in your pre work and then put it back in writing so that everybody's on the same page Anyway, she made a mistake, happens to all of us. And she's in the meeting and realizing, holy cow, we blew this. This is a huge opportunity, we've lost it. But she, you know, she made her way through the meeting and I'm sure she did a great job. But they weren't able to answer the one thing that the client really had wanted, the one outcome he had really wanted, because they didn't come prepared. Now that didn't mean they couldn't circle back with him after, of course. And they would. And that was basically what they. Because that's all they could say. They weren't at their office, you know, they were off site, remote location. They said, we'll circle back with all of that after. We'd like to, you know, move on to the things that we can address and cover today and we will get back with you. So it's a bust. And after she leaves, right? She had traveled to see the client. She traveled, brought her team to see the client, right, all these things. And now she needed the follow up. Was really going to be instrumental. And she was very frustrated with herself that she had let this happen. So she gets an email from the potential client that night and it was super harsh, you know, basically saying, listen, you somewhat wasted my time and I don't know how you didn't understand this is what I wanted and or needed. You know, it's really unfortunate and frankly, I'm really shocked that, you know, as the expert, I perceive you as that you would make a fumble like this. It was something really rough. I'm probably not even doing it justice. And so my client was emotional. She felt angry, offended. Totally happens. First of all, when that happens, never respond in the moment, ever. And my client didn't either. She actually sent me a 911 text and said, hey, I need to get an emergency session on the book in the next 24 hours. Something critical came up. Where can you fit me in? And we made it happen. And she explained to me everything that was going on. That was smart when you feel really emotional. Pause number one. I wait 24 hours to respond to anything when I'm emotional. And that always pays off. Don't respond. Even in my personal life, I Do this too. I did this. I was upset with my son last night and I decided I was just gonna sleep on it, even though I was really upset at the time. And I felt differently this morning, you know, having some time to process it and be rested. So pause first and foremost. Secondly, if you have a trusted advisor that you can reach out to, someone who's an expert in arena that you know you're. You're having some struggles in, tap that person for help. But don't just tap some random person because they're not going to be able to help you and they're probably going to give you bad advice. Okay, so we get on the phone. She takes me through everything I'm listening to now. I have no emotion around this, right? Because I'm a bystander. I didn't not qualify it. I wasn't in the meeting. I didn't get the email from the potential client, and I'm not suffering the potential loss. Right. My client is. So that was really interesting too, because I had no, zero emotional charge around the email. When she read it to me, it wasn't sent to me, it was sent to her, of course. So I processed it from an objective standpoint, only looking at. Okay, fair point. He's right. You know, we didn't qualify ahead of time. He's right. In some ways, we did waste his time. I saw it through a lot of the lens of, oof, you know, he's being really harsh, but he is right. Factually speaking, she did not process it that way. But when I shared with her the lens at which I saw it through, she did understand, right? And she calmed down a little bit. But she kept, you know, circling back to, yeah, but did he have to speak to me like that in the email? And, you know, she was still emotionally charged and upset. So I said, listen, here's the bottom line. Do you want to close this piece of business or not? That's step one. You've got to determine that. Because right now, the way you're acting, it sounds like you don't, like you don't. And that's okay. I remember learning early on in my career, if you don't want to work with somebody, just don't put the effort in, right? If there's not a match or if they disrespect you or treat you poorly, whatever it is, you don't have to take every piece of business. You don't have to let people treat you a certain way. You can respect and create your own boundaries, and you decide right can fire clients. You don't have to entertain clients. If you don't like the exchange with them, that is fine. And so that was my first question to her. She said, no, I want this business. This is what flipping huge, it'll be my biggest client. I said, okay, so we're clear, the goal here is to close this business, Correct? And she says, yes. Okay, then you need to step away from emotion now. Put yourself in his shoes. He was upset, he lost time. He lost time from his family. He had traveled, right? So we started trying to empathize with his situation. I said, now here's what I would do. I would fall on the sword. I would respond and say, I hear everything you're saying and you are right. It is really embarrassing that I did not qualify this. And it's like a rookie mistake. However, I have 25 plus years of expertise in this industry, which is unacceptable. And I so appreciate you taking the time to give me the feedback, to send me this email. Because here's the thing, guys. When he sent the email to her, yes, he might have been pissed. Yes, he might have want get it off his chest. But he's also engaging with her. To me, that's a buying sign, right? When I look at it objectively, he's wanting to do business with her. What? He didn't have to send her an email complaining about that. He could have just gone on with his merry little life and never spoken to her again. So I opened her eyes to the idea, this is a buying sign. He wants to work with you, but he has to get this upset off his chest. So fall on the sword. Take full ownership. Make zero excuses. One of the things I hated about this whole Rachel Hollis thing last year where she had this big social blow up with her team and whatnot. She kept blaming her team for things on social media. That is not a leader, Right? It doesn't matter if your team blew something up. You are in charge. So we talked about that. Own everything. Don't blame anyone. Own everything yourself. Be grateful for the feedback because that means it's a buying sign and he's engaging with you, right? And we're grateful for that and thank him. He didn't have to offer the feedback. It's also going to disarm someone. So when someone's angry and upset, they're gonna lash out more and more when we agree with them. Apologize for the mistakes that we've made because they are honest mistakes. You know, we didn't intend to do that. That's a fine situation to Apologize because we didn't want to waste his time. Certainly we want to earn his business and then thank him for taking the time to give us a feedback. So she decided to move forward with that strategy. And then I said one last thing. I would also suggest adding on as a close, you always want to have a call to action, you know, and any type of follow up. And so I said in the call to action here, I would want to include when is a good day for me to fly to you, not for you to go anywhere, not for you to wasting time, but for me to fly to you so I can apologize to you face to face and I can present the missing material that you were so looking for. In that, you know, that's just going the extra mile, showing that I am a true partner. I'm someone that shows up and you matter. I see you. And then I said, because I'm over the top. I said, find out what this guy drinks or find out like what special this guy get it immediately and overnight it so he has it tomorrow with a card saying thank you for, you know, talking with me about this. Just little things like that really make a big difference because a lot of people don't do them. So she did move forward with the plan and he ended up when he. When she fell on the sword, you know, and she owned it. She apologized and then she closed with that call to action. Then she sent the, I think it was a bottle of whiskey or something, I don't know. And he got it. He called her and said, oh my gosh, your response was so kind, so empathetic and I feel like a jerk. I was a little too harsh on you. So do you see how that mental jujitsu works, right? When you really are just so kind and understanding and accepting and owning what went wrong, that other person says, oof, I guess I shouldn't have been so harsh on you in that email. And now he's apologizing to her. Of course he gave her the other meeting. Of course he was willing to do it at a time that worked for her. And of course in the end she gets a deal. So that's just an interesting business example that is really around qualifying expectations on the front end, making sure we do our pre work right, have a checklist so that you don't forget things like that. And then when things do go wrong, and they will right, they go wrong for me all the time. I'm always making mistakes and learning, you know, own it, don't dodge it. Oh my gosh, the lady that I used to work with that ended up firing me. She would never own mistakes, never. Capital N, never. And it was such a flawed character. It was a character flaw in her as a leader that held her back from being a true leader. And everybody saw it. She'd never want to say, this is acceptable responsibility. The reason why the company's not doing well. No, it was always, this division isn't doing this right. This one is not doing. And people don't respect leaders like that. If you want to lead, you've got to be willing to fall on the sword. Meet a different guest each week.
If we think about tensions in our career, we have a lot of times the same things we've actually Wendy and I have seen in strategic discussions with executives, you have this tension between today or tomorrow, meaning am I putting my time, energy, commitment in hitting my current goals, which means performing, or am I looking at how I'm developing, continuing to learn, thinking about what the next step is going to be? Because Wendy and I see so many of these kinds of tensions not purely as oppositions, but as interwoven. Well, if you're thinking about the future, it does inform and shape the choices you make today. Just as the work that you're doing today helps you really think about enabling serendipity or plan, luck and thinking towards the future. So that botham thinking thinks about today, tomorrow, family, work, confidence, fear. Right. As interwoven opposites that actually we need to work through those tensions and learn from.
How can you break down with the example of, like, fear and confidence? Like, what are the steps that somebody takes to do that?
I think fear and confidence is an interesting one. I mean, I was thinking about this, Heather, particularly because of your focus. I think confidence is such a beautifully paradoxical phenomenon. And so here's what I mean by that. You don't get confidence by sitting in a room, keeping the bar low, trying to just mind your own business. You're never going to build the belief in yourself until you put yourself out there. I mean, Brene Brown certainly talks about that. This paradoxical interplay between confidence or courage and vulnerability. I think to me, confidence is very similar in that you build, you learn about yourself, you develop your capabilities, and you certainly grow your confidence through failures as well as successes by knowing what's possible. So when we think about both end thinking, we think about a couple of things. One is we start with saying, you've got to change the kind of questions you ask. If you're always saying, right, should I be brave or should I Be vulnerable. You're missing the point because they go together, right? How do you start to change this point of how do I build confidence? By putting myself out there in uncomfortable situations, by learning through my successes and failures, pushing in these opposing ways. To us, changing the question is absolutely vital. We then also push ourselves and the leaders that we work with to think about how do you take those opposing sides and dive deeply into each one of them? How do you really understand what are your fears coming from? Where do you feel your insecurities? How do you kind of wrap your arms around what's on that side? And at the same time, when you think about your courage, where are your strengths? That deeping, actually dividing and really thinking further about both helps you then step back and say, and how do I pull them together? What's my higher purpose? How am I holding these in a synergistic format that lets me think, what am I capable of if I really push forward? And then I think from changing the question to the separating connection, how do you start to walk the tightrope and learn through this process because it is such a journey? So you're not looking for a one off answer. You know it's going to continue. You're going to make a decision today, but in paradoxical tensions, the underlying issue is going to resurface. And that's okay. That's some of how we build some awareness of what's working in our world, what's working for ourselves. And I think building build that strength.
I asked you to try to find your passion.
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You know, if, if we say that this is a roller coaster journey and I think that I heard the best expression to define this roller coaster journey by Ben Horowitz from Grisson Horowitz venture capital firm. And he used to be a CEO of a startup. And he was once asked whether or not he was sleeping well at night as a CEO and said, oh yeah, I slept like a baby. I woke up every two hours and cried. This is the reality of the roller coaster journey. This is something that we need to realize. There is one part that people don't appreciate. The attitude towards risk and change is different for entrepreneurs. They are looking for the change. They want to change things, they want to change the world, they want to change, they want to create an impact and they are willing to take the risk because not all of them are successful. In fact, most of them are not. And the reality is that many people are risk averse. They don't want to take risk, they prefer to go into corporate America or they prefer to have stability rather than roller coaster journey. And therefore not everyone should be entrepreneurs. And it doesn't feed all the people.
One of the things that I found really interesting that you had attributed some of your ability to take on risk and your strength and resilience stem from your childhood with your father. Can you share a little bit about how your father impacted you?
You know, I think that was at the time I, you know, no one realized that, right. And, but when I would come to my dad with a crazy idea, he would say, why don't you give it a try? And, and the most important part is that you were just encouraged to try something new that you haven't done before, right? And, and obviously in many of those cases it didn't work. Right? And there was no judgment because the encouragement to take risks or to try new things or to do something, even if it's crazy, but actually go and do that has to be supported with the no judgment. And this is how you create lower fear of failures, right? Because every time that I try something, there was no judgment, right. If it didn't work, it did not discourage me from the next time to try something even crazier or something completely different. And usually the way that we grow our kids is totally wrong in that sense, right. We expect them to bring A plus and if they bring F, then we punish them. Right? And this is totally wrong. We instead of encourage them to try new things and fail, we essentially discourage them and they become afraid to fail. And if you're afraid to fail, then you're not going to try new things.
So true. And you know, even the way that you're explaining raising children, my career in corporate America was very similar. Yes, Heather, go try to change and innovate, but no surprises. Don't allow for any opportunity to drop any balls. Make sure we're still going to hit the P and L goals for the quarter. And as long as you can do it within that window, everything is fine. So there are all these, like you're saying, judgments and conditions that are really opposing the opportunity to innovate. So how do you, as an entrepreneur, even with that background, with your father supporting you to try things and embrace failure, how do you know when you start a company or start a concept that, okay, this has gone too far, it's not working, I need to give up on this now.
You know, for a second, I would say that entrepreneurs will never know when it's time to quit. One of the most significant behaviors of entrepreneurs is the greed is the perseverance, right? Is the never giving up attitude. And it goes together with the passion and the mission that is totally engaged with the, with this journey. Right? And so if you look at what is the most important behaviors of entrepreneurs, never giving up is number one. There are probably more into that, but never giving up is the most critical one. And an entrepreneur will never give up. And they simply don't have that in their dictionary.
Did you ever feel when you were starting ways that, oh my gosh, this, the challenge ahead of us is so big, I feel like I want to, I'm just not going to allow myself or that idea never even crossed your mind.
You know, the journey starts with falling in love with the problem, right? With really falling in love and actually defining that mission as your life mission.
Right?
And what happens? Well, the journey is that, number one, you don't remain in love for that forever, right? You hopefully you change that into other passions and other area, but you don't remain in love forever. The number two is that you face challenges that you had no clue that are going to show around the corner. And what happened is that you get your perseverance from two factors. Number one, the mission. You know, helping drivers to avoid traffic change, it's a big task, but it's also a mission. And when you have that in your mind, you feel like, you know, this is my mission in life. This is exactly what I'm going to do the world is going to become a better place if I'm successful in that and I want to do that. The second part is your teammates. So they sign up for your journey and they want to go into this journey with you and you are committed to them the same way that they are committed to you. And so the team and the mission are the one that actually helps you to go through the hardship and the challenging periods of this journey. And look, all the startups have hard times, right? A lot of hard times.
A lot of hard times is an understatement. Yes. And I think people oftentimes lose sight of that because they only see the glossy highlight reel on social media, which can be so challenging.
We don't think of Google as a company that struggled at the beginning, right? But they actually were unable to raise capital. And they approached Yahoo at the time and asked Yahoo to acquire them because they were unable to raise capital. And Yahoo asked how much? And they said $2 million. Two million? Not 2 billion, not 2 trillion, just 2 million. And Yahoo said no. So you look at it today and you say, big mistake. We actually don't know that for a second. I would say there are right decisions or no decisions, because when we make a decision, we don't know what it would be like if we would choose a different path. So we don't know what would have happened if Yahoo would have said yes. We simply don't know that. We want to believe that Google will remain whatever it is today, but that part we don't know. So all the companies struggled at the beginning and the Waze journey was pretty similar. Now we started in 2007 and the real magic of Waze is that we the drivers, crowdsource everything that is being used by the application. So we, the drivers generates traffic information, okay? And we get that. We generate the information about speed traps and accidents, and additional information we get, we the drivers creates the map. So when we started, the map was a blank page. There was absolutely nothing on the map. And the first driver drove. We collected from the device the GPS data. And if we take this GPS data and draw that on this blank page, we start starting to get something that look like all the roads of this person drove and all the turns of this person did and so forth. And if we started take that from a lot of drivers, we are getting something that looks like a map and we have built the software to create the map out of this data. And the map at the beginning is not good enough. It takes time for the map to become good. Enough. And during this period of time, we had no traction because everyone liked the story. We, the drivers, are going to help the rest of the drivers to avoid traffic jam, right? So you are ready to sign up to this mission and then you try it and it's not good enough. And so you give up. And we're trying that again and again and again. And every time we were doing exactly the right thing, right? So we spoke with the drivers, we understand what didn't work for them, and we built the next version knowing that we addressed all the issues and we know that the next version is it and it's not. And we're doing it all over again, whole year of iterations until it eventually become good enough. And that was three and a half years from the day that we started until we were good enough to the level that you would download the app in LA and you'll say, wait a minute, this is awesome, or this is good enough for me, or this is actually valuable. When we think of product market feed, in bringing value to your customers, there is only one metric, retention. People are coming back. If you create value for them, they will come back. If you don't create value for them, they will not come back. At the beginning, they didn't come back. It was really bad. It was embarrassingly bad. And it's evolved and improved, evolve and improved, evolve and improved the whole year of iterations until it become good enough. And this is really the reality of figuring out product market fits. It's an iterative process. Now I call that journey of failures. And the entire startup is a journey of failures. Now if you think of what does it mean journey of failures, then I want you to think of the following. And these are two critical conclusions. If you are afraid to fail, then in reality you already fail because you are not going to try. Albert Einstein used to say that if you haven't failed that because you haven't tried anything new before, if you will try new things, you will fail. As simple as that. The immediate conclusions out of that is that, wait a minute, if I'm due to fail multiple times, then the faster that I fail, I actually increase my likelihood of being successful because I still have enough time and enough resources to try something else. Make another attempt, another version, another improvement, another attempt, another version, and so forth. And the faster that you do that, you actually buy yourself enough time for another attempt. Now it's quite obvious that if you, if you're going to make more attempts, then you increase the likelihood of being successful. As simple as that. This is really important. So once you realize that this is your journey, then you actually have an opportunity to go and improve in the process of building your startup, in the process of figuring out product, market fit, in the process of later on figuring out your growth strategy. Because in many cases I ask people, so exactly how are you going to go to the market with that? And they will tell me, I'm going to put Facebook ads. Okay, maybe. And if it doesn't work, then they don't know. The reality is that if you will build a marketing plan with 50 different actions that you're going to take, what I would say is, okay, now you have 50 different experiments that you are going to make until you find one that does work. And this is the beauty of this year. You are looking for one thing that does work. And that one thing is actually, number one, creates, or it's a make or break for your turn. Number two, it buys you a ticket to the next part of the journey of building your startup.
I decided to change that dynamic. I couldn't be more excited for what you're gonna hear. Start learning and growing. Inevitably something will happen. No one succeeds alone.
You don't stop and look around once in a while.
You could miss it.
Come on this journey with me.
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