In short
Podcast Episode Summary: Gil Eyal - How Being a People Person Made Me Successful
Overview In this episode of Exit Paradox, host Anastasia Koroleva speaks with Gil Eyal, a successful entrepreneur who sold his influencer marketing software company, HYPR, four years ago. Currently, Gil runs a venture capital firm that leverages celebrity influence to boost consumer tech companies. The episode dives into themes of identity after an exit, personal branding, the intricacies of investing, and the emotional challenges that accompany the transition from founder to investor.
Key Moments
Introduction
- Anastasia introduces the podcast's goal: exploring life after selling a business.
- Gil shares his background as the former CEO of HYPR and current venture capitalist.
The Role of Influencer Marketing
- Influencer Marketing's Impact: Gil discusses how his software changed the landscape for brands and agencies in influencer marketing (00:09:33).
Identity Crisis Post-Exit
- Struggle with Identity: Gil reflects on the identity crisis that came with selling HYPR, akin to “giving away your firstborn” (00:14:41).
- Coping Mechanisms: He describes how he dealt with the sudden loss of his company identity and sought purpose through advisory and investment roles (00:16:55).
Financial Interests and Future Prospects
- Retaining Financial Interest: Gil talks about keeping a stake in his former company and the importance of understanding market dynamics post-exit (00:19:38).
- Advice for Exited Founders: He shares key advice for those selling their companies, including remembering the role of luck and the need for humility (00:24:02).
Building a Personal Brand
- Importance of Personal Branding: Gil emphasizes the significance of establishing a personal brand after an exit (00:26:37).
- Networking and Mentoring: Engaging with other entrepreneurs helps find new purpose and opportunities for mentorship (00:28:25).
Balancing Relationships and Personal Life
- Post-Exit Family Dynamics: Gil discusses the positive impact of his exit on family life, allowing him to spend more time with his children (00:35:06).
- Future Entrepreneurs: He reflects on whether he wants his children to become entrepreneurs (00:37:33).
Insights into Investing
- Investment Philosophy: Gil shares his approach to selecting companies to invest in, focusing on products with strong potential for consumer appeal (00:38:31).
- Challenges of Angel Investing: He elaborates on the risks involved and advises new investors to surround themselves with experienced mentors (00:43:24).
Advice on Post-Exit Lifestyle Changes
- Lifestyle Adjustments: Gil advocates for changing work habits post-exit, emphasizing the importance of taking breaks and enjoying life outside of work (00:46:17).
Key Takeaways
- Navigating Identity: Post-exit identity crisis is common; finding new purpose through mentorship and investing can help.
- Building a Personal Brand: It's crucial for former founders to intentionally cultivate their personal brand and stay connected with their professional network.
- Investing as a Journey: Successful investing requires expertise, patience, and sometimes learning from failed ventures.
- Importance of Community: Surrounding oneself with other entrepreneurs and mentors can provide valuable insights and support during the transition phase.
Conclusion Gil Eyal’s journey highlights that finding fulfillment after an exit involves redefining purpose, building a personal brand, and embracing new roles as an investor and mentor. The episode resonates with anyone navigating the complex emotions and challenges of life after entrepreneurship.
Connect with Gil Eyal
- [LinkedIn](https://www.linkedin.com/in/gileyal)
--- This summary encapsulates the key discussions and themes presented in the episode, providing insights into the entrepreneurial journey post-exit.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00Welcome to the Exit Paradox podcast, where we discuss how to build a fulfilling and meaningful life after selling a business. I'm Anastasia Koroleva, an exited founder who spent the last 13 years researching and collecting stories about life after a successful business sale. I literally sold and the next day didn't work for the company. So it was a very sharp separation. Gil Eyal. Four years ago, he sold Hyper, a software business which revolutionized the way big agencies and brands run influencer marketing. Today, Gil invests in consumer startups that can benefit from having a celebrity on their cap table.
0:38In this episode, we discuss overcoming a post-exit identity crisis, building a personal brand, and dealing with celebrities. Once you start investing, it's very hard to mentor without investing because everybody goes, wait, Gil's involved and he didn't invest? What's wrong with your company? A lot of people who want to be angel investors end up doing one or two investments. It's a portfolio game. Like you have to do a lot of them to succeed. I see about 300 to 400 companies a year to invest in three to four. Why would anybody pay for influencers when you can just buy an ad? If you gave me cream that I could put on my head, grow a full head of hair, no chance you would believe me that works, right?
1:17Unless you saw The Rock using it for six weeks and growing hair every day when you post.
1:28Hello Gil, very happy to see you here today. Thank you for joining me. Hi, Nastasja, thanks for having me. So, four years ago, you sold a software company, which built software for influencer marketing firms. And that company took you seven years to build, and it made quite a lot of noise in the industry. Also, as part of that process, you personally built a celebrity name for yourself. You got all possible awards. You were called the new king of influencer marketing. And you hang out with the likes of Leonardo DiCaprio and Serena Williams. So my question is, when you sold that company, how did you feel in terms of your identity that you were no longer part of Hyper?
2:16are? You know, it was really hard because you genuinely become one with that company that you build. Like people know you as the person who runs that company. And depending on the type of exit you have, it's not always, you know, it wasn't a billion dollar sale where, okay, now I'm going to become Mark Cuban and life changed. Of course, for the first time in my life, I had some extra money in my bank account. I wasn't worried about paying bills the next month, but I was still going to be working and there's a real identity crisis around it like oh it's almost like giving away your firstborn obviously not the same but this is the company that I built for seven years it's all I did it's the only thing I did other than take care of my family and it's a it's a real crisis it was it took me probably two years to bounce back what did you do to bounce back what was helpful and what maybe was not very helpful that you tried?
3:16I am wired to do work, so I wasn't ready to go relax right away. So I immediately wanted to bounce back, find out what the next thing I'm doing is. But I got unlucky. I sold Hyper in February of 2020. A month later, we were all home with COVID. There was no hiring. Nobody was doing anything. When you sell a company, you do get a lot of offers. But the quality of the offers that you receive are part of what the market's looking like. If people aren't raising capital, if people are firing people, then you get different types of offers. So I found myself doing a lot of consulting work, recognizing that a lot of other founders are going through the same identity challenges that I was going through and dealing with the same pain that I was dealing with.
4:02And that led me to start my own investment arm called Stardust, which is initially was supposed to be with other partners. Now it's just my brother and I. But it allows me to be a mentor and help other people. And that's where I was able to kind of bounce back. Suddenly I found new purpose. I wasn't building a company. I didn't have all the stress and the pain that comes with building a company. But I got to be around really talented, better founders than I was, honestly, that could build bigger and better companies that have eventually become more successful than I was. But it allowed me to just find new purpose after you kind of are left with the carpet being pulled under your legs.
4:45So did it help you with your identity crisis? Because now you could say, I have this venture capital firm, right? So it probably felt good to say that. Yeah, but my identity crisis wasn't about a title. It was more about purpose. Like, what should I be doing? You know, I was at the time was 42 years old. You're supposed to have a midlife crisis around that time anyways. And, you know, where do you go? What do I do? I used to wake up at 7 a.m., you know, put the kids to school and run to the office and then be there till midnight and come back. And suddenly I have all this free time. Nothing's really that important.
5:23Like you can only play so many video games. so you wake up you you still take the kids to school and suddenly it's 8 30 in the morning and I have nothing to do so for me it was about surrounding sorry it was about surrounding myself with interesting people it was about waking up and jumping out of bed knowing that there's a reason for me to come it wasn't really about okay am I still going to win all these awards and am I still going to be considered you kind of feel like the market keeps moving on without you and new and smarter and more developed ideas come from other founders. And you can either choose to continue to compete with them and try to build something or do what I do, which is, hey, let me find people who can do better and help them do it.
6:07So you basically jump back into the activity to feel needed, to feel this purpose, as you said, again. Yeah, I needed a drive. I needed a reason to get excited about the day.
6:24And, you know, when you have a company, it's too much of it. There's never an end in sight. You can work all day long. You're not going to get close to what you need. So it allows you to find a better balance. But I needed to be close to founders. I needed to be close to innovation. So you got that rhythm and you ran back away from it, back to work. Yeah, but a much more, you know, a much more controlled environment. I don't work. Usually, I'll, you know, I'll still answer emails and stuff like that in the afternoon, but I spend a lot more time with my kids now. I'm not tied down to the desk until midnight.
7:04If there's obviously if a founder needs me, then we're there. It doesn't matter what time, doesn't matter if it's a weekend. But you have a lot more control, a lot more free time and a much healthier balance. So how much you work per day and per week, you think? So I do, I work about, I'd say 10 hours a day now. A lot of it has to do with my investors own a really big real estate company. And they asked me to come in and help them with some of the work there. So a lot of my time is spent there. I'd say about 75 % of it. And then I do meet with founders at least five to 10 times a week, either new founders or founders that we've invested in.
7:41And the way that we do it is because of our experience with celebrities and influencers is that we come on, invest, and then for the first three to six months, we work side by side with them to get as much exposure and more importantly, credibility through celebrity and influencer partnerships. And then we kind of take a step back. So I always have one or two companies that I'm working with aggressively. And then obviously if they pop up and say, hey, we need your help. We're in trouble. Something happened. I just had a bad day. I need someone to talk to. then sometimes that will last till midnight, but I don't really see it as work.
8:13It's my hobby. 10 hours a day. Lucky you. Pretty much. So it sounds like you are leveraging that amazing network that you've built with Hyper now in your new venture. Can you tell me a little bit more about how you choose those companies you invest in and help? Yeah. When I was a founder, I used to think that investors are jerks. You would get either a maybe or a no, but never really a good explanation of why. And then when you start investing, you really have to think about what you're doing and who you're going to invest in. And I realized I'm not going to compete with Andreessen Horowitz for the best deals.
8:57They're not going to come to me. But there are spaces where I can be a mini version of that, right? Where the value that I can bring would be enough for the best companies to want to work with me and the best founders. And where that really came to play is companies that have an amazing product, so amazing that you probably wouldn't believe would work because it's too good to be true. and it sells to a consumer that could be convinced and influenced by the types of people that I've worked with before, which are either influencers or celebrities where it makes sense. And so what we look for ideally is a consumer company, often CPG, but also consumer tech, where if I told you, hey, I have this product, you'd be skeptical.
9:46That's the beginning, right? Because some of the example I always give is if you gave me cream that I could put on my head, grow a full head of hair, no chance you would believe me that works, right? Unless you saw The Rock using it for six weeks and growing hair every day when you post it. So we're looking, you know, that's the ideal company. If you're out there, call me. We're going to do big things together. But we look for companies where, sorry, we look for companies where that's the story, right? Where that's being able to do. And then we say, okay, let me see if I can pitch the company back a plan and say, hey, if you bring me on board, here's what I'd want to do.
10:23I'd want to bring this celebrity, and then I'd want to go to this retailer. And that would require you to offer the celebrity compensation because we won't do it for free. Are you willing to do this path? And if they do, and we love the product, and more importantly, we love the founder, we have to love the founder, then we think about it as a viable investment. The result is that there are plenty of amazing companies that we pass on that just because we don't have the right value for them. The great example of that is a company called Deal, D-E-L. We were one of the first. I've known the founder for many, many years.
10:59He's offered me an opportunity to invest. And I said, look, I don't know this space. Obviously worth$12 billion now or something like that. Would have been nice had we invested, but I can't look at it that way. I have to focus as an investor. What we do try to do is be very direct with the founders and tell them the truth. Why didn't we invest? If it's really because it's just not a good fit for us, or do we think there's some flaw in the pitch? You know, maybe the market's not big enough. Maybe there's better competition that we've seen out there, things like that. Fascinating. So let's go back to you personally.
11:35Your motivation to work, and as you said, you work 10 hours a day and you're happy to do that. how how did your motivation change from the time when you just started at hyper and today what's driving you so you know I started hyper I was really no one you know no one knew me I had a pretty good education I didn't come from a lot of money but very loving and warm family and supportive family and you know my brother was a successful uh private equity and you know manager and my younger brother worked for, you know, big tech, Intel and then Apple. So, you know, a lot of disappointment to fail or not fail.
12:20And not a person who generally loves stress. But when I was working, before that, I got exposed to some celebrity work and I realized the impact that the then nascent influencer marketing space would have on digital marketing. So I felt like I really needed to do something in that space and thought that maybe I could make a lot of money. But I knew that it would take a long time for me to make a lot of money. What really drove me was to build my own reputation. That's my recommendation to every single person, whether you're a founder or not, is think about yourself as a brand, your personal brand.
12:54And how do you get to the point where people think of you as the authority figure about something? And it doesn't matter if you're starting a company or if you're just working at a big organization. If you want to be promoted, if you want to get bonuses, then you need to be the recognized expert about something. You want to be the person that we can't deal without. So I was very driven to try to build myself into that person. And I thought I had an opportunity because it combined a few things. One, it was an up-and-coming market where the old guard wasn't really excited about people who were doing digital marketing.
13:31really dismissed it at the time. They thought, why would anybody pay for influencers when you can just buy an ad? And I've heard that sentence so many times back in the day. So I felt like there was a big opportunity for a market that was going to be really, really big. The current active players are dismissing. So I could carve myself out a spot in it. And I also, you know, interesting people and the type of people would be attracted to this industry or the type of people that I want to work with. So I got into the space and started, you know, iterating because it probably took me five or six versions of the product before anyone was willing to pay for it.
14:17But what I found was that once I found a product that people were excited about, they were really excited about it. and so it became fun the first few years are just fun I felt like I was on this project that was kind of had the legs of its own legs people were excited to meet me you know I'd always been trying to get meetings suddenly people were asking to meet me I was being asked to speak so once it once I got some confirmation that wait I might be on to something it was very fun for many years until the later years which we'll talk about which became much much harder but the first two years were literally the best job anyone can ask for with you know the greatest people and in a space that was just tons of fun to work in.
15:05Are you happy you sold or do you ever regret? I wish I'd sold a year or two before we talk about a little bit but the market had shifted on us we recognized the market shifts pretty early because we were a data-driven company but not all of our investors agreed to sell we did have some offers that were higher so I wish we had taken them. You know, sometimes you get, you need luck. So we got lucky that we sold before COVID because we probably wouldn't have even sold maybe a few months later. But had we sold a year or two earlier, I think we'd all done a lot better. But, you know, hindsight is 20-20.
15:43Am I happy I sold? Yes, 100%. I think by that point I was fed up. The market had changed. We clearly recognized that the market was going to become a lot more difficult. Social networks who had previously dismissed this market couldn't really care about who's doing it, recognized that this was taking a chunk out of their revenue stream and started implementing different algorithms and doing everything they could to make our lives miserable, to make it harder for people to work. An example is a big social network. We won't say the name, but I'm sure people will guess. Called me up and said, hey, we suspect that you're doing something improper.
16:20So just know that we're considering suing you. And I said, what do you think I'm doing? They said, well, we can't really tell you. And I said, well, are you going to write me a letter? No, just know this. Now go raise capital when, you know, a very, very well-known, guess which one, one of the biggest social networks in the world, just called you. And you have to, you know, of course, you're going to disclose it to any future investor because you're not going to raise capital and get a lawsuit a week later. Of course, they never sued us. They never called us again. But good luck, right? So the market was starting to take a shift.
16:48The big players are doing everything they can to make our lives miserable. And the result was that I wanted out. So I didn't regret it, even though it came with a lot of separation anxiety. Yeah, the separation anxiety is very common in our post-exit founder community, as you know. So how did you achieve that closure? How did you move on? It was really difficult because what happens when you sell a company for not, you know, $3 billion is that even investors that made some money or gained some, some of them are happy, some of them are upset. And I had a whole, you know, by that point we'd raised 20 something million dollars.
17:27And, you know, we had co-founders and employees and everyone to take care of. And you never know, like every single person that you tell it, some of them are ecstatic, some of them don't care. And some of them are mad because they thought you're their ticket to God knows where, right? So a lot of it had to do with dealing with relationships and finding out who really was there for me and who wasn't. And not to say that I was perfect, but I did my best to get the best outcome for everyone. And so a lot of the investors were amazing and supportive and happy with the results. And others were, you know, awful.
18:08anywhere from you know just bad mouthing you behind your back for selling the company when they thought you shouldn't have sold the company and different things like that so a lot of it had to do I think it was probably a year of just kind of you know staying out of the out of the light talking to people you know having conversations some of them really unpleasant conversations with people that the people who maybe invested $25 ,000, but felt like they weren't included in the decision to sell. And often, or not often, but some very aggressive. So it's a tough situation. And some people might have thicker skin.
18:47But for me, I really needed, it wasn't a breakup where like one day I sold the company and I was gone. It was more like, okay, I, you know, there's a whole waterfall that is coming after this and I have to deal with every single component of it. It was also interesting because often when you sell a company, they ask you to stay on. We had merged with a competitor and then sold. So their competitor really, their competitor's CEO really wanted to stay on. And it was a perfect scenario because as I said, I was fed up. So I literally sold and the next day didn't work for the company. So it was a very sharp separation.
19:24Okay. Did you keep any financial interest in? Yeah, I still do. We'll go, you know, I still own, the sale had, you know, was broken down for cash port equity. And as you mentioned earlier, the acquirer who was supposed to go public soon after, but the markets, obviously COVID and everything, the markets making it difficult, is now supposed to go public. So it would be nice. Nice if that goes well, but we'll see. You'll have a good outcome. So you're happy you kept a bit of your equity? Yeah, no, look, I still like the company. So a lot of the people still work there. It was a great place to work, I think.
20:03and it would be nice to have a happy even happier ending for everyone involved because everyone will get some more cash personally i've been a lot more successful as an investor than as a founder meaning that i've made a lot more money on other people's exits as part of your venture investing after you exit or you're talking about your investments even before you exited yeah no after Now that I do my own investments afterwards, some of those companies have grown to be unicorns and done much better than our sale. And so instead of tens of millions, we're talking about billions in sales. And so it's just compounded, right?
20:42So as an investor, I found that I have done better. And I think I may end up being a founder again, but I think version one of Gil as a founder, looking back, there's a lot of things that I could do better because I'm learning from the founders that I invest in today. So for many of us, it's actually very hard to transition from a founder into an investor, just psychologically. Because what's required from a founder is so different than what's required from an investor in terms of your personality. So what's your take on that? I don't think I was a regular founder ever. I was very much a people person.
21:19I built an amazing team around me. People wanted to work with me with all modesty. you know we consistently would check if people are happy we never had people leave the company people only wanted to join and we built something that I felt was very special for everyone involved but it allowed me to attract people that were really really good at what they did so I think that component is a really good fit as an investor too you know people want me on their board people I think you know a very supportive investor so a lot of those qualities kind of transform. If you're the type of founder that's a very diligent CEO that needs to know everything that's going on, that micromanages the company, that was never me.
22:06And those qualities create really, really good founders. They're not the only qualities that create really, really good founders, but they're often seen in really good founders. for me I think my personality was always a good fit for someone who's an advisor or an investor and I think a lot of the founders that we work with feel like they get a lot of value simply but from the fact that I tend to analyze and understand what's going on and kind of give them a clear vision when often you know you get tunnel vision when you're a founder and that's what I did for my company you know I had an amazing CFO I had an amazing marketing person I had an amazing COO and those guys, I let them do their work and just kind of helped whenever it's time to notice, oh, wait, you kind of missed something or there's something else you should look at.
22:54I was the type of founder that I think easily transitioned into this position. Yeah. But there's a variety and I don't think I was the best founder. You know, I think there were better, not that I was bad, but there are definitely better founders out there and I'm finding that out every day. So basically, it was your people skills that made you a successful investor. It's a combination of people skills. And I have this ability to kind of envision, kind of build out where I think the challenge is, where the strengths are, and kind of really quickly analyze and understand strengths and weaknesses.
23:30It's kind of like a SWOT analysis in the head. And then one other thing is I just have, you know, some people have different gifts. My gift is I have a positive approach, meaning it's very hard to convince me there's no way to solve something. And I usually come up with a creative way around a problem or to solve it. And I think, one, people like to be around that. And two, I think it's very effective often. So as a founder, you're constantly bumping into walls and it can be very, very disappointing, very depressing. and you can lose faith. But for me, for some reason, in life, in business, I always see a way, you know, to move forward.
24:14If you're talking to someone who is just selling their company, what would you tell them not to do? It's a great question. Well, I think, you know, the number one piece of advice for me is that to understand whether it means to be humble or to be less judgmental of yourself, to understand that you're only part of the equation. what you sold your company for, whether or not you failed or succeeded as a founder. A lot of it has to do with luck. A lot of it has to do with decisions that were made with limited information. So if the sale is amazing, you know, stay humble. If the sale is just okay, don't be too hard on yourself.
24:53And if you didn't sell or, you know, it was a bad ending, you know, take some time, pick yourself up, recognize what you did right and figure out how you build, again, And then that's one piece of advice. The other one is, you know, think about everybody who is with you on this journey. And how do you make sure that you don't leave behind people that were unfairly treated? So, you know, we all know about options. We all know about equity. And the result often is that people end up, when it's time to sell a company, end up realizing that they own a lot less than they thought they did. They got diluted.
25:30They didn't realize how much stock they actually had, all these things. So if you haven't been transparent until now, which you should be, is my advice. But if you haven't, make sure you have these conversations. At the very least, let them know that it matters to you, that you care. But more importantly, do what you can to make sure everyone got what they put into this company. I'm sure these were not very easy conversations for you. And you said it took you a year to deal with all of them. It was interesting for us because we were kind of in between. People made money, but it wasn't the dream money that a lot of people had hoped.
Read the full transcript
26:13So maybe 2, 3x of what they put in. But the reaction was very different. Some people were ecstatic. Some people were furious. and I'm the type of guy who really cares when somebody's really mad at them. So it was very difficult to deal with. But at some point, you have to tell yourself, look, I've done everything I can to get the most out of this company and to be as fair as I can to everyone involved. And if somebody doesn't appreciate that or is still angry, then at some point, you have to let yourself off the hook. So you mentioned that you were very intentional about building your personal brand as an expert in your field are you continuing to do that now i think so is it part of your strategy now after you sold i think we should all be doing it all the time doesn't matter again if you're just on your first job or you know you're if you're an intern with 11 other interns you need to be known for something you need to be because nobody will remember you otherwise but you need to be known as a guy who really understands excel or the one who's really funny or the one who has great marketing ideas.
27:25You have to stand out. So do I work at it full time like I did as a founder? No, I had a PR team. We did everything we can to get attention. I don't have the resources and the time to do it now. Do I do everything I can to stand out? That's why Stardust operates differently than other VCs. That's why we bring on board the celebrities. Yes, I think you should always be doing it. and I do my best to always be doing it. So for example, someone sold a company and they're going through the identity crisis and they did not have your story when you already intentionally focused on your personal brand for a while.
28:02They're just thinking, you know what? I really want the world to know what I've done. But at the same time, I do appreciate that a lot of it was luck and I don't want to look like I'm bragging. game. So what would you advise be for a person like this in terms of, let's start with the mindset. What would the right mindset, the healthy approach to building your personal brand post-exit would be? Yeah, I think number one is like what we're doing right now, you know, speak to other founders, people who've gone through a similar process, start not on camera, you know, so I've had a lot of these conversations, just one-on-one.
28:44And, you know, what should we do? What do we want to do? And what you find is that people have a very broad reaction to it. There are people who want complete, want to jump right back into it. They're already ready to start their next thing. There are people who need a lot of time off. So find out who you are first. The only time you have that's a break not to be building your brand is when you're still exploring what that brand is. Like, who do I want to be? And once you do, think about where does that mean I'll be in five years and how do I get there? So if I, in five years, I want to be known for one, two, three, four, what do I need to do to get to that place?
29:24And treat yourself as the brand that your startup had. You know, most of us, even if it was an enterprise SaaS, we built a brand for our companies. And that brand was known for certain things. So now think about yourself as that brand. Okay, so I know that I'm really, really good at one, two, three, not so good at four, five. so I'm not going to bother with that. But one, two, three, where can I be that creates a real impact and helps me become known for what I'm doing? One. And two is what kind of activities can I put out that demonstrate to people that that's what I'm doing? So it's anywhere from, you know, hosting your own podcast to just writing on LinkedIn or on other social networks to joining groups of other founder, former founders, like, you know, that's where we met.
30:08And then what I did, which I think is a really, really recommendation for anyone who's sold a company, is just find a few founders that are getting started and work with them. Go through the entire experience through someone else's eyes without the stress, without the burden of making the final decision. And then evaluate yourself and say, okay, wow, I thought I was really good at this, but I'm looking at another person and you know what? They're better equipped to do it. Maybe it's something else. but really understand what that brand is before you start building it. So I know you've done some mentoring also in addition to investing into companies.
30:46What did it give you? Was it a good idea? Was it a waste of time for you personally? So in full honesty, sometimes it's amazing. Sometimes it's a complete waste of time. And a lot of it has to do with who's on the other side and whether or not they want to listen. I am notoriously known for starting my emails with, hey, I'm wrong all the time. So take this with a grain of salt. I just sent one right now. And then, you know, kind of giving them tough love. So I just met with a founder this morning that pitched me on an investment, loved the founder, but the product itself is just a small market.
31:24And I wrote her an email afterwards saying, look, I really liked you. I really liked the product. But, you know, it's a luxury item in a small market. That means that, you know, I'm going through McKinsey style exercises. I can get to$50 million market cap, you know, that's where you're going to end up. And that means you're not going to be able to raise capital from really big VCs in the next round. And it means that because you didn't raise capital from the big VC rounds, you're not going to have a lot of money to market. And that's, I just summarized the email pretty much. And I said, and like, I'm really excited about you.
31:59I want to invest in you, but I can't invest if I, you know, if I know that my money is going to be the last money in the company because I'm a small player. And then I was very tempted to say to her, so I think you should dump this product and start a new company. But I didn't say that. I said, I am here for whatever you decide. Here are some ideas. You could go after a new product. You could convince me that there's a bigger audience than I think for this product, maybe take it off the luxury market and go into a larger place. Let me know what you want to do. But the one thing I really avoided was to say, and then I'll decide.
32:37But I said, but for now, it's a no. And I think one of the things that a lot of mentors, a lot of investors will say is, I'll decide later. Or, you know, let me know what's happening. You know, they're hoping that things will work out. I say no, because I don't want them to change their idea because they want me to join or because they want my money. I say no and I say, well, if something else happens, let me know. And I know it's kind of counterintuitive because you want to stay in the game. And if suddenly a big VC invests, of course, you don't want to be left out. But that's how I do it. And I think it's rewarding because what's happened when I've done that a lot now is often they won't change and they'll stay.
33:16And maybe I'm wrong. Maybe I'm right. It doesn't really matter. I mean, it matters, obviously, if I'm wrong and they do really well, it's a bummer. But I'm happy for them. It's a bummer for me. But every once in a while, they'll come back to you and maybe a week later and maybe two years later and say, hey, we've shifted. You know, maybe it's maybe we've listened to your advice and we've listened to other people's advice. But you see progress that they've made. And those are the people you really want to invest in. You can see that they make sense. So as a mentor, and again, I'm wrong all the time, but if I am seeing them listen to advice, accept it and have a better product as a result or better access to the market or better marketing plan, that's really rewarding, especially if you own part of the company, but even if not.
34:02So it sounds like you've done some mentoring outside of your venture investing, but now you're also doing it as part of your venture investing because you invest in pretty early stage companies, don't you? Okay. So for you, what is more rewarding when you are mentoring as part of investing or without money involved? I'm just thinking for someone who is considering different options of what to do after they exit, which way you think they should lean towards. So, you know, the interesting thing is I found that once you start investing, it's very hard to mentor without investing because everybody goes, wait, Gil's involved and he didn't invest.
34:50What's wrong with your company, right? What does he know that we don't know? And often the reason I don't invest has nothing to do with that. The reason is because I can only write a$50 ,000 check and you need$4 million, right? So I'll invest maybe when there's a round. What I don't do is just mentor and say, hey, I'm not interested in investing, but let me mentor you. And for that exact signal. but if I plan on if I'm really excited about the founder really excited about the company and there's no round happening right now I'll promise them and keep that promise that I will invest as soon as there's a round so that we can kind of circumvent that question of wait why didn't Gil invest I think it's a win-win for everyone one they can go around and say hey Gil's committed to invest I can say to people hey I'm really excited about this company and I'm going to invest So you should, or not that you should, but, you know, I would recommend that you think about it as well.
35:50And if the company, if I write and the company does well, I actually own a meaningful, or not meaningful, but at least I own some of it. So my style has been, if I really, if I'm not going to invest, I probably will not also mentor at that point. Which makes a lot of sense for you, for sure. So your exit, how did it affect your family and your relationships with your nearest closest people? Well, it didn't cause it, but I was going through a divorce, an amicable divorce at the time.
36:27And we're still in a very good relationship, but we weren't a good fit for each other. And I don't think it was driven by the sale, but I think the sale made it easier because at least there was some stuff to split up. and we were very close so we just cut everything in half and we got along really well. I think it was really good for my kids you know that my kids barely saw me. I would see them in the morning by the time I'd get home they were asleep most of the time. I'd see them for a little bit in the weekend but I was working throughout the weekend. I was like okay we'll go out for two hours and I need to go get back to work.
36:59I was working all the time. Now I spend a ton of time with my kids. I work almost entirely from home so I'm always there when they're here. You know if they're at their moms, then obviously no, but when they're here, I'm always there for them. I can drive them around. I pick them up from school. I go to all the school events. I'm the dad with, you know, it's mostly moms, but I'm the dad who shows up to serve pizza on Friday morning for the Friday lunch for the kids. So I think it's been, it's been great. I'm really getting, you know, an opportunity to spend a lot more time with my kids. They're eight and 12 now.
37:32So I've just been, I've been happier. I I think they've been up here. I get to embarrass them every once in a while. It's great. Would you like your kids to be entrepreneurs when they grow up? Wow, that's a great question. I haven't thought about it. I think when I was younger, we were always taught that we need to find a serious job and that we need to make a great living. And the generation above mine was all about keeping one role, keeping that one job. And there are certain people who can be happy that way. I was not. I started my career working in that type of environment, left and people thought I was crazy to go to business school and then start my own company.
38:17But I found what made me happy. So to answer your question, if that's what would make them happy, yes. I don't think, you know, they're still young, but I don't think that would fit both of them. I think my older son is a creative type. He doesn't like high stress environments. You'd probably do better somewhere else. I think my daughter could be a real extender. She's only eight, so we'll see. Whatever makes them happy. If they want to, great. So do you see yourself as an investor in the foreseeable future? Yes, I think what's happened to me is, you know, I made some money off the sale, invested a small part of it.
38:56We did pretty well. You know, instead of 25 investments, you know, probably we have three or four unicorns. And then we have probably 10 or 15 others that still have a shot. So we'll see what happens. We did pretty well. But it takes time to get liquid with these deals. So on paper, we've made a very, very successful effort. But we haven't seen 90 % of it hasn't come back yet. As that comes back, I want to start writing bigger checks. But in a perfect world, five years from now, I have a$100 billion fund. and I invest much larger checks and don't need to chase other investors to join me in the round, but kind of just do it myself, yeah.
39:43So what part of the job you don't like? One, the hardest part is saying no. You know, I always, as a child, I remember thinking I was really, really jealous of the extremely beautiful people. Like we all know one or two of those people that you just, they walk into a room and they're like, oh, they're so beautiful. And I had, and like, as I got older, I had a friend who was one of those people and became his friend. And he said to me one time, something that really struck me, which is like, he said, you know, you're my only friend. And I said, what does that mean? He's like, I don't know. Guys don't want to be friends with me.
40:18And, you know, because the girl's around. And women, you know, they only want to date me. They don't want to, no one wants to be friends with me. And I said, so what's the hardest part? He said, well, people are always hurt. Women are always hurt when I'm not interested. And it seemed at the time very, very, I was like, ugh, that's kind of like icky. Don't say that to people. But as an investor, you're kind of the prettiest person in the room, right? Like people reach out to you. And that part I love because, you know, I'm not a huge extrovert. Like I'm not the type of person just going to reach out to people all day long.
40:51But you have to say no all the time. That's really hard. Like it breaks my heart sometimes. Like this founder we talked about this morning, she's amazing. and I know she's good I don't know if she's going to take my no the way that it's meant which is look I would love to invest in you but the product needs to be targeted a larger audience I think she might because I used to as a founder just take it personally and say like oh I guess you know that's all you know investors speak for you're not good enough and that's not the case but you're consistently drafting these emails where you explain to people why it's a no and you know that even if you're as gentle as possible, you're hurting their feelings.
41:28And that part, I really dislike. So how much risk are you taking personally in these investments? Like, are you using most of your money to angel invest? Or is it just a small portion? So my brother and I do all of our investments together. So it's always 50-50. I would say about, so, you know, we all have piles of money, right? We have what I need to pay the bills and all that stuff I don't touch. Then I have some solid solidified investments in stock and stuff like that. But then there's a pretty, for a person like a pretty meaningful pal that I invest, it's probably like 10 to 15 % of my income goes into investments.
42:11So pretty significant for considering I come in very early, very high risk. But what we found was based just based on And what we've done so far is that even though it's considered high risk, if you bring on board, if you have a really, really good plan, then we're definitely doing better than one in 10, which is kind of the number of people throw out for startups. It hurts when you lose, but it's the kind of excitement that I want to have in my life and I'm willing to pay that price. Even if it is risking a pretty meaningful chunk of my net worth. So you are doing it primarily not for money. You're doing it because that gives your life purpose, as you said.
42:55I don't know if I would say that. I do want to be a billionaire someday. I'm still a very, very, very long way from there. But yes, no, if there was no money involved, I'd probably have to find something else. I do have a responsibility for the next generations and my family. And as I mentioned, like my first exit was, it set me up, but it didn't really, it was not a retirement type style exit. So, yeah, I think when I get called to be on Shark Tank, then I'll know that I've made enough. So you clearly have some very specific value to bring into all these companies with your backgrounds, with your connections, with influencers and celebrities.
43:37But for someone who doesn't have that, do you think angel investing is a good investment from purely rational financial standpoint? I don't think so. I think that if you're not an expert in the area that you're investing in, you will not do well. I see about 300 to 400 companies a year to invest in three to four. And the reason why we've been successful is because we really, really know the space we invest in. We can create value immediately. We can get them into retailers. We can get them partnerships with technology partners. we can get celebrities on board. I try to look back at how companies did.
44:25And generally speaking, I think the one in 10 number is very optimistic. Usually the startups you'll find, if you're not very well connected, you don't have really, really good relationships or reputation where the best companies will come to you, are the ones that are not going to be successful. So you'll do a lot worse than one in 10. So generally, I would say, just be an angel investor? No. What you can do is you can partner with people that do know what they do. Either join an angel group that has people from the industry to his focus in spaces that you know something about. You don't have to, maybe you made money working for a big CPG company.
45:02Great. So join an angel group that focuses on CPG. You don't have to choose the companies, but surround yourself with people that know what they're doing. That's one thing I would say is, definitely do it. The other thing I would say is a lot of people who want to be angel investors end up doing one or two investments. It's a portfolio game. You have to do a lot of them to succeed. And that means that if you're just going to the market without having a reputation, you're not going to see nearly enough companies to invest it. You have to join one of these groups. You have to participate. You have to be willing to take some risks and assume you're going to lose some money in the learning curve.
45:38So my advice is no, don't start being an angel investor out of nowhere, join a group. Don't invest in the first three deals that you see. Just sit there, listen to how people are thinking about it. Think about what you would do and then look back three months later and say, should I have invested in this company or not? And then write your first check alongside a group like that. When you see the best companies, you're like, wow, these guys are so much better than everyone we've seen so far. Then you can write your first check. One exception I have is if you're very, very wealthy and VCs will let you join in on their rounds, you can become a very successful angel investor simply by building relationships with really good VCs and saying, hey, whenever there's$200 ,000 that you need, let me know.
46:20I'm not in a position to write$200 ,000 checks, but that's what I would do in that scenario. Brilliant. So I asked you before what not to do after an exit. Was there anything that you would tell people, do this? This was great. I'm happy I did it. Yeah. First of all, join the group that we're in. That was an amazing experience. So we met through this group of post-exit founders. And I just joined like two or three months ago, and I've met probably 30 or 40 amazing people that gave me perspective on what they're doing, what I'm doing. It's amazing how everybody takes this process differently. But yeah, surround yourself with people who've gone through that process.
47:02Number one. Two, within the people that surrounded your startup, there probably were one or two investors or mentors or advisory board members that meant a lot to you, that did really well for you, make sure that isn't the end of that relationship. You know, stay in touch with them. You know, for me, I had a guy named Charlie Fetterman, another guy named Larry Wagenberg, who are part of this program that we started with that ended up close to me till this day. But for the seven years that we ran the company, they were my closest advisors and supporters. And we're still in touch. Um, and, um, if I ever start something there, there'll be the first phone call I make.
47:45Um, but, um, yeah, so keep in touch with those people that really matter too, is within your team, there are probably a few standouts. If someday you want to do something or you're going to help somebody else do something, make sure you keep those relationships because those are the people that you'll immediately think about, who do I want to bring into this project? And you'll be at an unfair advantage because you already know a few people that could do way better than the average person. And then three is like force yourself to change your lifestyle. Like this idea that you have to work all the time, that you can't go to sleep knowing that you, there's an email in your inbox.
48:21Take it out of your head, you know, force yourself to go on vacation. I hadn't gone on vacation for the seven years I had hyper. I hadn't gone on one day of vacation. One day I was working on planes. I went to visit family. I was working for, I was like, is there a setup for me to work um that's not healthy it's not good so force yourself to take some time off let your brain take some time off to find out what you like that isn't work and do it whether it's playing sports or watching sports or video games or going to parties I'm going tonight I'm going to I paid 70 to go listen to Scott Galloway Professor Scott Galloway talk about his new book I don't know you know I it's what brings me happiness amazing you'll Thank you so much.
49:06There was so much wisdom and you opened up so beautifully. I really, really enjoyed our time together. Thank you so much. Me too. Thank you so much for having me.
From the publisher
Four years ago Gil Eyal sold HYPR - a software business which revolutionized the way big agencies and brands run influencer marketing.
Today, Gil runs a venture capital firm which adds value to consumer tech companies by bringing celebrities onboard.
In this episode, we discuss overcoming a post-exit identity crisis, building a personal brand, dealing with celebrities and becoming an investor.
Connect with Gil:
Linkedin: https://www.linkedin.com/in/gileyal
____________________________________________________
(00:00:00) Intro
(00:01:17) Welcome
(00:09:33) The role and impact of Influence Marketing
(00:14:41) The struggle and lessons of selling a company
(00:16:55) Dealing with separation and moving on after selling
(00:19:38) Retaining financial interest and future prospects
(00:20:37) Reflections on past experiences as a founder and transition into an investor
(00:24:02) Advice for someone selling their company
(00:26:37) Building personal brand post-exit
(00:28:25) Reflecting on mentorship and investment choices
(00:30:06) Balancing relationship with personal life post-exit
(00:32:46) The impact of investing on mentorship
(00:35:06) The effect of an exit on family
(00:37:33) Prospects for children becoming entrepreneurs
(00:38:31) Future as an investor
(00:39:10) Challenges in the investment industry
(00:39:33) The challenges of being an investor
(00:41:20) Personal risk in investments
(00:43:24) Advice on angel investing
(00:45:32) Joining a group and surrounding yourself with experts
(00:46:17) What to do after an exit
(00:48:02) Changing your lifestyle post-exit




