How to Turn Fear Into a Superpower

21 Jul 2025 · 29 min

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Problem Solvers Podcast Summary

Episode Title

How to Turn Fear Into a Superpower

Host

  • Jason Feifer, Editor-in-Chief of Entrepreneur Magazine

Guest

  • Eynat Guez, Co-founder and CEO of Papaya Global

Episode Overview

In this episode, Eynat Guez shares a pivotal experience from her entrepreneurial journey that transformed her understanding of fear and risk. She recounts how a contract clause nearly bankrupted her first company, and how confronting her worst-case scenarios led to a significant shift in her mindset and leadership strategy.

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Key Themes and Takeaways

  1. Confronting Fear:
  2. Eynat faced a daunting situation when a contract clause required her to buy back shares from a holding company at five times their value. This clause threatened her company's existence.
  3. Initially overwhelmed by fear, she chose to confront the worst-case scenario instead of panicking.
  1. Visualizing Worst-Case Scenarios:
  2. After allowing herself 24 hours to feel defeated, Eynat mapped out the worst possible outcomes:
  3. Possible bankruptcy of her company
  4. Termination of employees
  5. By visualizing the worst-case scenario, she realized that life would continue, and she could still pursue her passion for travel.
  1. Gaining Leverage:
  2. Understanding that she had nothing to lose allowed Eynat to regain control and leverage in negotiations. She recognized that the holding company also had stakes to lose in a protracted legal battle.
  3. This shift in perspective empowered her to negotiate a more favorable outcome.
  1. Adopting a Strategy:
  2. Eynat consulted with multiple lawyers to assess her options. The right legal counsel helped her create a strategy that minimized legal costs and resolved the issue in a timely manner.
  3. She established a timeline (60-90 days) for resolution, emphasizing her desire to avoid prolonged conflict.
  1. Encouraging a Fearless Company Culture:
  2. Eynat emphasizes the importance of helping her team overcome their fears and embrace change. She encourages team members to confront their own fears, breaking down seemingly impossible challenges into manageable steps.
  3. She promotes a work environment that is dynamic and suitable for those who thrive in changing conditions, fostering a culture of innovation and resilience.
  1. Personal Experiences with Fear:
  2. Eynat also shares her personal experiences, particularly around pregnancy and its impact on her career. She encourages women to view life events in a broader context, focusing on the short duration of absence rather than potential fears of failure.

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Practical Advice

  • Evaluate Risk: Always assess what you have to lose and what the other party has to lose in any negotiation.
  • Seek Trusted Counsel: Surround yourself with advisors who understand your goals and can provide actionable strategies.
  • Embrace Change: Cultivate an environment that values adaptability and innovation, encouraging team members to step out of their comfort zones.
  • Change Perspective: When faced with fear, shift your mindset from loss aversion to viewing challenges as opportunities for growth.

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Conclusion

Eynat Guez's journey highlights how confronting fears and understanding the implications of worst-case scenarios can empower leaders to navigate business challenges effectively. Her insights serve as valuable lessons for entrepreneurs and business leaders on transforming fear into a strategic advantage.

For more insights from Eynat Guez and information about Papaya Global, visit [PapayaGlobal.com](https://www.papayaglobal.com).

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Host Information

  • Jason Feifer: Editor-in-Chief of Entrepreneur Magazine, focusing on actionable solutions for entrepreneurs.

Stay tuned for more episodes of Problem Solvers, released every Monday.

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Transcript

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1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show that solves entrepreneurs' toughest problems. I'm Jason Pfeiffer, Editor-in-Chief of Entrepreneur Magazine, and each week I take a problem that you're probably dealing with and get tactical solutions from people who have been there and solved that. So, let's get solving. Anot Gez has built three companies, most recently a global workforce management platform called Papaya Global, which is currently valued at$3.7 billion. But many years ago, when she was working on her first company, she ran into a problem that would forever shape how she approaches business and how she thinks about risks.

2:17So, here's how that story begins. Inat launched that first startup, and after a few years, she decided to sell part of her business to a holding company. I thought that this will actually help the business to grow faster and so on, but it wasn't a great partnership. So after two years of this bad partnership, she says that she wants out. And the holding company says, okay, in that case, you need to buy back our shares for five times their value. Because that's what's in our contract. Are there any scarier words in business? As a young and inexperienced founder, Anot had signed a contract with this crazy monster clause, which said that if things ever went wrong with the partnership, she needed to buy back the shares for about five times the value.

3:08That amount of money would have absolutely bankrupted her. But the holding company that she had partnered with, they didn't care. They were just like, look, here's the contract. You signed it. So now pay up. I remember going home and seeing only black. I was, I don't know, 27, 20 years old. That was my first company. I've built this company from scratch. I was very proud of it. And all of a sudden, somebody is explaining you that you need to pay him a crazy amount of money. And I gave myself about 24 hours of feeling as the most stupid person on earth, of bringing myself to this situation. But then after I said, okay, you need to be practical.

3:49I mean, what do you do? It's a good question. What do you do? And what she did next changed everything. I started imagining the worst case scenario. The worst case scenario is that I don't have the money to pay them and it doesn't make sense to me anyhow to pay them this amount of money to buy my shares back. So, you know, we are going to close the company, the company is probably going to go bankrupt and so on. And everything that I've built will go back to square one. That's not a great scenario. Obviously, I had about 50 employees at the time, so you need also to terminate them. It's not great for them.

4:23But after going through all of those very not great scenarios and sad scenarios, I said, OK, what I'm going to do next? Up until now, Anot was thinking the way I'd say everyone is thinking, probably all the time, which is jumping to some kind of worst case scenario, whether you're in a major problem or not. And in this case, obviously, she was in a major situation. But thinking through what is the worst thing that could happen, and then getting really emotionally caught up in that, really worrying about that, really trying to avoid that, that's the normal thing. And that's what she did. But then she did something abnormal, something that maybe we all should be doing more of, which is that she thought, Well, OK, if the worst case scenario happens now that I have imagined what it is, what happens after that?

5:23What do I do after the worst case scenario? I'm going to travel to India. So I'm actually going to take my backpack and I'm going to take six months off and I'm just going to pack myself and just be on the roads again with zero kind of worries, because honestly, I just got rid of all of my worries. And all of a sudden, this kind of scenario didn't look really bad to me because it says, OK, that's going to be rough. That's going to be a very rough lesson. I'm going to lose a lot of money. I'm going to lose a lot of things that I've built. but the day after I'm actually going to have something that I really like to do.

5:59I like to travel. I like to eventually get into new adventures. I was single at the time. I didn't have a lot of commitment at home so it was a perfect period as well. And this actually helped me to fight back. To fight back. I bet you didn't see that coming. I didn't when she was telling me this story, to Aenat, the logic goes like this. She was afraid of losing her company. Then she imagined actually losing her company, and she realized that, you know, life will go on. If the company closes, that will suck and she'll lose a lot of things, and then she will put herself back together and go traveling for a while and enjoy life, and life will go on.

6:43The worst-case scenario is not actually all that bad. It's bad, but it's not all that bad. And if that's true, well, then the worst case scenario isn't something to fear. Suddenly, she had nothing to lose. She could operate without the fear of the worst case scenario. And when you have nothing to lose, you suddenly gain a lot of power at the negotiating table. This is completely changing the narrative. And actually, this gets you to the point beyond the fear, because you are not looking on kind of failure any longer, because you already know what's going to happen when you're going to fail. And you're ready for that.

7:26And it's not that scary. So, OK, let's work on other scenarios. For example, she could tell this bad partner of hers, look, if you bankrupt me, then you will lose all the money that you've invested into me. So go ahead and do that if you want. Or let's find some way out of this where we both don't have to take a huge loss. And that's what happened. That's how she saved the company. And the lesson that she learned here was, in business, you should always look the worst-case scenario in the face and think beyond it, and it will make you braver and stronger. Today on Problem Solvers, we're going to dig deeper into this lesson and how Anot has applied it throughout her very successful career, which, let me remind you, currently involves being the CEO and co-founder of the$3.7 billion with a B dollar company, Papaya Global.

8:24So how do you look beyond fear? How do you embrace the worst case scenario? It's all coming up after the break. All right, we're back. I'm talking with Anat Gaze, the co-founder and CEO of the global workforce management company Papaya Global, about facing and overcoming fear in business. And to start, let's go back to that story that she told at the beginning, because I I needed to know, once she overcame her fear of the worst case scenario, what exactly did she do to save her company? So I spoke with five lawyers and I told them, this is the situation. I need to fight for that. What's your best advice?

9:07And, you know, I mean, each one of them had his own strategy and so on. Some of it said, I mean, you have no chance. I said, OK, thank you. Bye. I mean, I went to the other one. And, you know, this is also part of it. And I think when you're an entrepreneur, you are used to hear things that say, that's not going to work. You're not going to, it's not going to make happen. You're not going to succeed. That, you know, if you're going to listen to everyone that tells you that you're going to fail, that's obviously, I mean, you are going to fail because you're not going to try. And I found someone and he made me understand that there is a way and there is a clear strategy here.

9:41And he gave me kind of the tools or the things that I can do in order to change this narrative. And he also explained to me what they have to lose if we don't get to a settlement. Because sometimes when you're looking on things, you understand what you have to lose. You always need to understand what the other party have to lose. Because honestly, when you have a legal dispute with someone, no one wins. I mean, fully. They have a lot to lose. And dragging things is not a great scenario for everyone. And once we mapped everything and I understood kind of what is it that I'm going to do? Can I make it happen?

10:14Is it visible? I mean, one of the lawyers told me, okay, do you have a million dollars to fight back? I said, no, I don't have a million dollars to fight back. And I don't want to pay a million dollars in legal fees. He said, okay, so, you know, so just kind of don't do it. And I went to the other lawyer and he was like, okay, that's not going to cost you a million dollars. That's going to cost you, I don't know, 50K. And this is how you're going to do that. And I tell you that if you're going to do that, it's going to end in two months time because they will understand that if it doesn't end in two months time, you have nothing to lose.

10:42You're going to go travel and they're going to lose the whole business. So I think it's also first, you always need to take advice from people that you feel very comfortable and that they understand what you want to achieve and they can be a good partners to you. OK, and this is very, very personal. It's very individual. But once I had this kind of partners, I mean, aside me, that obviously kind of covered the legal aspect. And once I had this very, very clear path of saying, I don't want to spend two years on this anyhow. I don't want to spend two years of my life going to work and hating the company that I founded because I don't like my partners and I have legal fights with them because it's not fair for my employees.

11:23So I actually gave myself, I don't remember if it was 60 or 90 days, to solve this. And if it's not being solved, I'm quitting. And by the way, this was one thing that he told me. Okay, what happens if you're going to quit? You are the CEO. They know nothing about the business, right? So use the tools that you have. You're recognizing that you have more power in this situation than you thought you did. And I really love this point that you were making there about how at the start you were very focused on what you had to lose, but you recognized that they have things to lose too. And what that really accomplishes is an overcoming of what psychologists call loss aversion theory.

12:04Loss aversion theory, decades of psychological research have confirmed, is that we operate in which our primary objective is to avoid loss rather than to seek gain. And so when we're in a situation where we feel like we have something to lose, what we tend to operate in is a very, it's a crouch position where we think about what we have and we try to preserve that. And any outside actor we see as simply in a position of taking something from us. But this mind shift is really helpful because what you're saying is you are not the only one who has something to lose. You can trigger this same loss aversion theory in other people as soon as you can recognize what they stand to lose and they might actually have more to lose than you do, which is very, very interesting.

12:59The other thing I wanted to just circle back to before I forget is to go even earlier in your story, which is you said there was this provision in the contract, which ultimately was the thing that led to this giant legal fight that almost bankrupted the company and that your lawyer at the time had said, don't sign that. and you hadn't listened to them. And I'm listening to that little moment and I'm thinking about this instinct that you now have to think about worst case scenarios and whether you now look at every detail like a provision in a contract and play it out to its extreme worst case as a means of testing whether or not you should do something.

13:43No. The short answer is no. I mean, everything that you said was completely accurate. I mean, you really kind of take everything that I said and kind of nail this to the bottom of how it works in my head. That's my job is to take what people say and say it back to them, but it's shorter. That's basically my whole skill. Amazing. So I would say that I cannot live my life. I cannot do anything in my life if I don't trust the other side. And I think it's impossible. Honestly, if I decide to sign on an agreement, on a partnership, on anything, business-wise, private-wise, I need to trust a person.

14:20I need to really trust a person. Because honestly, legal disputes, doesn't matter what the contract is saying, if you don't trust a person and you're going to eventually end up, or in your mind, the worst case scenario is legal disputes, I don't want this scenario ever. So I'm going to avoid this, okay? If I think that we're going to do business together and we might end up in court, I'll say, okay, I mean, thank you, but we can stay friends, but I don't want to do business with you. And I think this is by intent and by default. What I learned from that is that you need to respect the professional people that are supporting you and that are in your side.

14:53And if someone is telling me, listen, this specific clause is first, is not common. Second, this might be the outcome. And it's not on every single kind of clause in the contract because, you know, it's endless and you cannot really do that. But those are the specific things that you know that can change the outcome drastically. you need to listen to them and you also need to give them the space and respect them and not to kind of bypass them okay i think at the time i was young i was naive i wanted to please this partner i wanted to show him that i trust them and obviously that was the wrong decision how do you apply this to your work now you're now running a much more substantial company and you have this experience to bear on it and i want to just take this thing that you said you've been doing since, in some way, childhood of understanding that there's value in playing out the worst case scenario, not to fear, but rather actually to find some strength in it.

15:53How do you apply this to your work now? And do you encourage your team to do it too? First, yes. I think as individuals, the one thing that always holds us back, I mean, on our personal life and our career is our fears. Once you are willing to give up your fears, This is where you are starting to move forward. This is where you can do major shifts. This is where you can really kind of bring a completely different kind of contribution and values to yourself and, you know, to the company, to anything that is around you. and I really try to get people out of their fear zone and try to break this down with them when they say no this is impossible no I cannot do that though this is a huge change okay I'm in love with changes I can do constant changes because I really feel that this is how we develop as people and so on and so I try to break this down with them and I do try to take this to the worst case scenario of a business by the way it's much easier you don't want to do a change because you don't want to fail at the end of the quarter okay it's not your personal failure right it's the company failure.

16:56You're still going to go home. Everything's going to be okay. Maybe you're going to feel bad. But generally speaking, what's the outcome of not doing this change? I mean, what are we losing by not doing it or by deciding to avoid kind of the decision? And I think this is a constant kind of thing that you need to take people through this journey. By the way, I also think that if people, for example, are not so great with changes or are not kind of very kind of great with dynamic kind of workplace and so on, they're probably not going to come to work at Papaya because really this is where people thrive with us.

17:32But people that are looking for their very, very same routine, this is not the greatest kind of place. I think that the tech industry in general, I mean, you cannot build a hyper-growth company by kind of being on consistent patterns. And it's great for you to be able to articulate that so openly and clearly. I mean, you're saying like, look, this is a great workplace for a certain kind of person and not a great workplace for other kind of people. And that by itself will do some weeding out of the kinds of folks who can join your team. But still, everybody is concerned about some bad outcomes.

18:10And I wonder maybe if as a object lesson in leadership, if you could unpack like, what is it that you're doing? Or can you give me a scenario in which someone on your team is either coming to you for counsel or you're seeing something that they need a shift in perspective in and how you help them face the scary unknown. I would say, you know, there are a few kind of ways to get there. I used to be a professional kind of swimmer when I was a kid. So I always said that the way that for me to be better and to be improved is that somebody yelled at me every single kind of, you know, every time that I finish the pool and tell me you're not good enough, this person did better than you.

18:53I mean, what's going on with you and so on. And I'm saying it because I think that there are few ways to get to the same outcome. I think that the best thing that I can do for someone is trying to get him out of his own story that he has in his head. Because 99 % of the thing, when people will tell you why they cannot do something, they will not tell you because I'm afraid of failure. They will tell you, this is impossible. You know, I don't have enough resources. I don't have enough time. I don't have enough this. This one is not ready. And there is always so many. I mean, the story really stopped them for seeing anything else.

19:28And sometimes, you know, I'll take them to a journey and tell, OK, how much money do you need in order to make it happen? How many people do you need? If I'll give you 10 people tomorrow morning, can you make it happen? And all of a sudden, you know, when we break this to kind of some impossible, possible scenarios, I mean, obviously, nobody thinks that I'm going to just give them a million dollars to solve every problem tomorrow morning. But I think they're starting to really kind of get out of their story. And I think sometimes you also need to be brutally honest to tell someone, listen, this is in your head.

19:58This is your story. I mean, please allow yourself. You're super talented. Just give up the story. Okay? Just try. That's it. Don't, I mean, stop holding yourself. And you're really kind of saying it up loud. They understand that you see it. And sometimes I think people just need to assure that people see it and saying it quite loud and kind of helping them to confront with this. And I think this is really a conversation. I mean, I wouldn't tell you that it's going to be working with everyone because honestly, it won't be working with everyone. And some people are just not attentive to listen or they're just kind of, you know, we leave the room and said, okay, I mean, much more frustrated because they feel that, you know, they wanted to get the approval of staying for their position and they didn't get approval or they get something to tell them your prescription or your, the kind of the signature that you're looking for does not exist or it will not happen.

20:55But I think that you constantly need to get them, if this is hard, through small steps where they feel confident. I mean, some of them can do like large steps. Some of them needs to do baby steps. But once they overcome, and honestly, I've been mentoring people or I have, I think about like 15, people that have been working with me for 15 years or so during my career. And I always gave them bigger role than their experience because I saw something in them that I said, okay, they're willing to listen. They're willing to go to very, very difficult kind of, you know, feedback and experiences because they want to be winners.

21:31And if you get people to be on their winning zone, this is where things change. And I'm sorry, that was my luck. It sounds like this career-long experience of facing major risks, grappling with major things that go wrong, have taught you in a way not just how to face them yourself and not just how to help others face it, but how to develop, I suppose, this very realistic perspective of what risk really looks like in business. But like, I feel like what you're saying is in some ways, like, first of all, you have to discover for yourself whether or not you are the kind of person who can navigate high stakes.

22:18And some maybe can't or don't want to. And that's like totally fine. But at some point, you need to go through a trial of your own to discover if you're the kind of person who can grapple with that. And then as a leader, part of your job is to not save people from these trials, but rather figure out which ones can really navigate them as well. Because the team that you ultimately want to build is a team of people who are able to envision worst case scenarios. And then like you did in your 20s with that first company, understand that there is something that comes next from that. And out of understanding that worst case scenarios are not actually the end of anything comes a kind of fearlessness.

23:09And what you want to build is a team of fearless people. What do you think of that? Yeah, I don't think that I've built a team of fearless people. And I have my fears as well. I'll wrap up with an example. That's a very kind of female kind of example. But I think every female in the world, even, I don't know, Hillary Clinton will feel this way. And when you have your career and you realize that you are pregnant, this is one of the most scary moments of your life. And it doesn't matter how much you are happy about it. Okay, I'm taking consideration that we are all happy to kind of, you know, from this moment.

23:45But a moment after, you are just fearing because this is honestly, you are walking through the unknown. You need to walk to a meeting with your investors, with your managers and tell them, hey, guys, you know what? I'm not going to be here for three months, six months. I'm pregnant. and eventually you know that this is not for the company's best interest, right? You're not going to be at work, so obviously it cannot be for the company's best interest. And I cannot count the amount of conversation that I've done over the course of the past few years with friends, with kind of just random women that people ask me to talk to them, telling me, how do I make this call?

24:24How do I tell people that I'm pregnant? And I told them, listen, I've been there, okay? I had three kids during kind of the course of papaya and I needed to go to my investors every single time and tell them that I'm pregnant. And by the way, my reaction to that was very, very different on the three kind of courses of time. First time I was fearing, okay, I literally apologized that I'm pregnant. I think it was a very small group of angel investors. They were all very, very supportive. Not a majority of them, I would say, but that went okay. And I went to the kind of when I was trying to fundraise for our A round, I was pregnant again.

25:02And I went with a full confidence of, okay, everything is good. Our metrics are great. There is no problem around here. And it really kind of hit me badly. Okay. Everybody kind of turned us down because I showed up to meetings while being pregnant. And that was a very shocking experience for me. That really kind of crushed my confidence in myself. I really felt bad for the company. I felt bad for my employees. I felt that I'm failing them because I cannot eventually do what's best for the company because I'm doing what's best for myself. Our kind of my third kid, it was during COVID. We were fundraising at the time and it was during COVID.

25:39Nobody saw me. So Zoom is great for being pregnant. And I was so traumatic from the last round that I literally sent a short email to all of my investors a week before birth. By the way, I'm going to have a baby. Everything is under control. Don't worry. It's very, very different from number one, yeah. I agree. But every time that I try to explain a female founder or a female employee how to deal with it, because they're figuring about what's going to happen with their career, how people are going to react, I tell them, listen, think about it on a completely different way. Each one of us, because, you know, life is not always great.

26:18We have parents, we have kids, we have other issues that will happen in our life that will require personal attention. Everybody is going through something in life. Everybody needs a period of time when they are going to be off work because they have other things. Don't make it over the pregnancy. Make it about the fact that it's actually a very, very short period of time during your career that you are not going to be there. And just assure that you feel this way, okay? Because if I'm working in a place or I'm working in a company for five years and now I'm going to be absent for a month, two months, three months, it's a relatively very, very short period of time.

26:53And once you're breaking it down to units that are not emotional, that are not what people are going to say, how I'm going to fail them and so on, it's also helped you to overcome this fear. And honestly, this is the biggest personal fear that I have. I'm not going to have a fourth kid, so I don't know if it's still actual. But I do think that eventually try to train yourself to be fearless and look on your fears on a completely different way is a very, very important exercise. And this is such a useful conversation. Really appreciate it. I just want to make sure people understand Papaya and that if they are the right customer for you, that they're getting in touch.

27:29So what do people need to know and where would you direct them? Excellent question. So Papaya supports multinational organizations, mean markets to enterprise, with unifying everything that is related to their global workforce and global payments. Really one platform to support 160 countries and make everything much more seamless, much more unified, and so on. So it's a great use case if you have people around the world, or if you have vendors around the world, or if you have contractors around the world, this is what we do on the day to day. And the website? PapayaGlobal.com. PapayaGlobal.com.

Read the full transcript

28:02Inat, thank you so much. Thank you. And that's our episode. Now let's keep the conversation going. I write a newsletter called One Thing Better, where each week I offer one new way to be successful and satisfied and build a career or company you love. You can find it at one thing better dot email. That's a web address. Just plug it into a browser. One thing better dot email. And if you get one of those emails and reply, it goes straight to my inbox and I will get back to you. Problem Solvers comes out every Monday morning. So make sure you're subscribed so you don't miss an episode. The show is produced by Emily Holmes and Money News Network.

28:44My name is Jason Pfeiffer. See you next week.

29:11When it's deep in the rain, it's Persil.

From the publisher

Eynat Guez, co-founder and CEO of Papaya Global, shares how a single contract clause nearly bankrupted her first company and why confronting that worst-case scenario changed everything. Instead of panicking, she mapped out the fallout, turned it into leverage, and negotiated a way out. That mindset became a repeatable leadership strategy, helping her build a $3 billion global payroll platform while navigating both personal and professional risk.
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