See show notes for this episode: S 02 | Ep 30 Net Worth vs. Self-Worth: Why Your Startup Isn't You.
Alex: We're joined by two authors of the bestselling book, High Five Energy. They represent a different kind of founder. I'm delighted to introduce you to Jeffrey Chernick and Alix Gitter. The interesting thing is that they're not just co-authors; they are "cohabitators." In fact, they're a married couple who just wrote this book. I'm super excited to have both of you on the pod.
Jeffrey Chernick: Thank you for having us. We've got two little girls, so it’s a whole affair.
Alex: So, it's a family affair?
Jeffrey Chernick: It’s a total family affair.
Alix Gitter: Yeah.
Alex: Well, I’m sure the girls keep that creativity going through the night. I'm sure you wake up and get some nuggets of wisdom. It is incredibly fun to have both of you here. Jeffrey, you come from the serial founder world. Alix, you're from a more creative or artistic universe. Tell us the story of how you met—because everyone is interested in that—but also how that led to this book and the specific topic you selected.
Jeffrey Chernick: Yeah, I'll start. It goes back to Lehman Brothers investment bank, if you've ever heard of it. That was my first and last job right out of school. I was on the banking team in corporate cash management and I wanted to share a taxi to work. This was in an age when it was either a 10-minute taxi or a one-hour subway ride. It was pre-Uber, around 2007. I thought, "Why don't I start a website that can connect me with someone going to the same place at the same time to share a taxi?"
We launched it, and it was my first hit of the "startup life" addiction that has lasted for the last 20 years. I've been scaling and starting companies ever since. I had one exit, and I think I'm going to have my second exit next year—or maybe even this year—which is actually that first taxi-sharing website. It’s still evolving as a commuter management software platform.
I just love coming up with ideas, solving my own problems, and then just doing it. I met Alix in 2016 at a pretty cool after-party for a very "L.A." spoken-word artist named IN-Q.
Alix Gitter: Yeah, I was on a date with someone else, and the rest is history.
Alex: The rest is history.
Jeffrey Chernick: I knew the guy, but I did not know she was on a date!
Alix Gitter: My background is as an actress by trade, and a writer as well. It wasn't really until I met Jeffrey that I realized this idea of creating your own structure wasn't relegated only to the acting world. Actors have to build their lives around auditioning or whatever they’re up to, but that actually extends into the entrepreneurial space as well.
When it came to writing the book, Jeffrey originally wanted to offer a roadmap based on his coaching and mentorship. He wanted to broaden that outreach to a wider audience. When I saw the first draft, I said, "Let me help you."
Jeffrey Chernick: She elevated the words and the ideas. The base layer stories are certainly my lived experience, but the elevation of those concepts into a global theme was Alix's doing.
Alex: Right. It applies to any creative profession, because basically, actors are just good-looking entrepreneurs, for lack of a better term.
Alix Gitter: That's very succinct; I'll take it! But yeah, the book quickly evolved into a larger offering. What started as "hacks"—like "do this to achieve that"—became a wider exploration of what it actually means to be an entrepreneur. What are you going to do if you forego employment at a "real" job to pursue a passion or a problem you want to solve? I think that’s where the magic of the book comes in. From there, Jeffrey had the great idea of including iconic founders to illustrate how these themes—and the "lows" of the journey—are universal.
Alex: It sounds like an acting career is known to the outside world for its ups and downs—at least until you become famous. Even then, people probably ask, "What have you done lately?"
The founder community is similar; Jeffrey and I are part of a serial founder community where there is a constant quest to stay relevant, overcome challenges, and find meaning. Whether it’s acting or a founder’s journey, it’s a bit of a "dojo." You’ve brought in wisdom from successful people, but what have you learned from those who haven't been successful? Or perhaps from those who pursued serendipity, thought they found it, but it didn't pan out?
Business school professors often say the problem with many books is that they only select successful case studies—and sometimes, ten years later, those "successes" are no longer successful, which is embarrassing. For people facing challenges right now who aren't sure if they will succeed, what did you learn?
Jeffrey Chernick: It’s twofold. Within the stories of success, there are countless moments where things almost fell apart. The book doesn't just show the highlight reel. We look at TripAdvisor or HotelTonight, for example; at one point, the founders actually offered to give investors their money back because the business wasn't going anywhere.
There are moments where you’re hitting your head against a wall and running out of money. You might be fifteen pivots deep before you hit on an idea like Google AdSense. In the book, we share Eytan Elbaz’s story regarding Applied Semantics. The common narrative is: "Applied Semantics was acquired by Google for $102 million; that must have been an amazing journey!" What you don’t hear is that it took eight pivots. That’s eight times they thought about giving up, but persevered.
The biggest lesson was that even the most iconic companies went through the same struggles as the everyday founder. They all hit roadblocks and asked, "Does it have to be this hard?" And sometimes, it really is that hard.
We also share stories where it just didn’t happen. We feature a story about Knotel, an amazing real estate play in New York City. They were crushing it, but then COVID-19 hit. Despite having funding, they just couldn't get past it. The book isn't just about business cases; it’s about the psychology of how people get through those moments and the importance of separating your work from your identity.
Alex: Self-worth.
Jeffrey Chernick: Exactly.
Alex: Right. You have self-worth as a parent, a spouse, and a human being. Your startup may go through ups and downs; the first one might fail, but you take those lessons and apply them to the second. Maybe that one fails, too. But the third one—after eight iterations or eight pivots—might succeed. Is the goal to build a "wall" where you separate yourself from the negative feedback the world gives you?
Alix Gitter: Well, that and exploring what "success" really means. The general narrative is that success is a billion-dollar exit or a life-changing bottom line. We propose that while those have value, there is also immense value in the entrepreneur who doesn't have the billion-dollar exit—the person who builds a great business that supports their family and their community.
In High Five Energy, success isn't relegated to "unicorn" experiences. It’s a holistic look at entrepreneurship that activates every human’s capacity to create something.
Jeffrey Chernick: Yeah.
Alix Gitter: ...and become a valuable contributor to society and their community.
Alex: That's beautiful. What I'm hearing is that there is a prevailing narrative typically coming out of Silicon Valley, New York, or parts of the L.A. tech ecosystem. It’s driven by VCs who engage in "thought leadership" and have a very particular return profile that makes their business model work. A lot of people listen to—for lack of a better word—"successful founder porn." It leads them down a path of doing unnatural things and certainly not looking for balance, because that whole business model depends on being unbalanced and exponential.
First of all, they’ll say, "Oh yeah, not every business is for VCs." Jeffrey, you’ve heard that narrative. But then they quickly move on and say, "Well, this is how you become great," and they list specific characteristics. When you go deeper into these stories, that narrative often breaks down because they can't actually predict the patterns.
What you brought up is something I’m starting to explore more with this podcast and the guests we invite: I am far more impressed by someone who continues to grow as a human being while building their business—someone who creates an environment where the employees come out as better people. Making money and building wealth is part of it, but as you said, we should separate net worth from self-worth. You’re giving people opportunities to do their best work and be their better selves. They then take the qualities they learn at work into their family lives. I'm working on this myself—realizing that if I’m screwing up in the same way as a parent, a CEO, and a spouse, there’s a lesson there. If I figure it out in one part of my life, things get better across the board. I’m curious, what have you learned from your conversations regarding this dimension?
Jeffrey Chernick: First off: how you do one thing is how you do everything.
Alex: Beautifully said.
Jeffrey Chernick: That is the family motto. Whether it’s professional, being a dad, or just the general tidiness of your life—there is a correlation. As you were talking, the main thing that came up for me—especially since we discussed VCs on stage talking about "money, money, money" and "$200 billion in exits"—is that there was no real talk of money when I spoke to these founders.
I’d ask, "How did it feel when you finally closed the deal?" I asked Eytan Elbaz what it felt like when he sold Scopely for nearly $5 billion. Maybe after your second time at bat, you get a bit immune to it, but for him, the money didn’t outweigh the feeling of having an amazing day with his family. Those are truly inspirational conversations because we all have these fantasies about what it’s supposed to feel like when we "finally get there." They demystified that a bit.
Perhaps it was the type of entrepreneur I attracted for this book. Taking a step back, this book is about what happens when you lean into your passion and the thing you want to create. When you live in that state, coincidences start to happen, you meet the right person at the right time, and things fall into place. That is what we call "High Five Energy."
Alex: By the way, I feel like we need to do a "Zoom-style" high five. Jeffrey, join in.
Jeffrey Chernick: This is a very important note: it’s not just a typical, "Yay, high five!" It is grounded in a feeling—the energy you feel when you truly connect with someone. The idea was born from books like Napoleon Hill’s Think and Grow Rich or The Secret, which are all about imagining something so clearly that it manifests.
I always had trouble just thinking of an idea and connecting with it. But when I root it in a feeling—like, "What would it feel like to make that big sale we’ve been talking about? What would that energy feel like?"—I feel it in my body, and it starts happening. That’s where the title came from. It’s the same energy that happens when you build your group, talk about your ideas, ask for advice, and pay it forward. When you lean in that way, things start to roll. That is the message we want to leave for founders. The through line of all these conversations was that energy of never giving up, paying it forward, making employees happy, and realizing it’s about more than just building a business.
Alex: Alix, a question for you as someone married to a founder who has worked through all of this. I feel like there is "dirty fuel" and "clean fuel" for accomplished people. Dirty fuel comes from fear—the fear of not being enough or not being accepted. I come from a refugee immigrant background; in the Soviet Union, you had to thrive and be the best engineer just to get anywhere. That legacy creates a need to always do better and achieve more. The through line of fear is the feeling that you’ll never actually achieve "success."
Many founders start with a chip on their shoulder. But as the company scales or they mature and start families, they need to connect with different types of people. It feels like the most successful ones—the ones I want to imitate—evolve to be driven by purpose. Not just a generic purpose, but the meaning found in creating something that thrives, much like raising a child. Is that what you’re referring to? That these founders gravitate toward "clean energy" and away from fear?
Alix Gitter: I really like your definition. I think that’s a very visual and accurate way to articulate what you’re talking about. You’re right—we’re at an interesting apex in our culture, not just regarding entrepreneurship, but regarding everything.
I fear that "fear" is a huge motivator across all industries. Take acting, for example: so many actors just want to be loved by their parents. they go out and think, "If I can be famous and loved by the world, I will finally feel a sense of worthiness. That will be enough." Those themes are soul-deep.
What’s interesting about Jeffrey—and I can say this from the outside as his partner—is that he is genuinely a light. He is motivated by joy and connecting with people. He wants to leave the trail behind him better than he found it. That’s why I married him. That’s what inspires me and why I aligned with him on this project. I am truly inspired by the love and goodness he imbues into entrepreneurship, fatherhood, and being a husband. To broaden it out again, I’m going to "borrow" that "dirty fuel" concept because I think it’s brilliant.
Alex: Don't worry, I’m sure I stole it from someone else! Feel free to use it.
Alix Gitter: I think that’s why it doesn’t matter if you sell your company for a billion dollars or if your returns are massive—it will never be enough if your motivation is rooted in fear rather than joy, love, or solving a problem. Once you hit those numbers, there is still more to go because the fear is still there.
We are at a sort of cultural crisis, and that’s what we hope to shift with this book. We want to offer everyone—entrepreneur or otherwise—the understanding that their creative essence and their capacity to create are inherently theirs. Their worth is inherent. To be a collaborative force for good, to make the world a better place, and to enrich your community—that is the ultimate payback. That is the return you should be after. That’s the message we’re trying to deliver.
Jeffrey Chernick: Amen.
Alex: Amen. Beautiful. As you were describing Jeffrey’s characteristics, I almost wanted you two to give each other a little kiss or at least a high five! That was lovely. I hope one day my partner says something like that about me—I have a long way to go.
Alix Gitter: Jeffrey, don’t get me wrong—doing a creative project with your spouse means we can be quick with the sassy comments! But there is also a level of depth, intimacy, and a reward in truly getting to know the other person.
Jeffrey Chernick: There is a reward, though it's not without its challenges. It’s been a wild ride, that’s for sure.
Alex: Beautiful. Alix, as you were talking about actors, I was reminded of Jim Carrey’s acceptance speech from a few years ago. I’ll put it in the show notes.
It goes something like this: They introduce him as "two-time Emmy award-winning actor Jim Carrey." He gets up and says, "I am Jim Carrey, two-time Emmy award-winning actor. When I go to sleep tonight, I won't just be getting any sleep; I’ll be getting well-deserved shut-eye. And I won't be having just any dream; I’ll be dreaming about becoming Jim Carrey, three-time Emmy award-winning actor... because then I will finally be enough."
He’s clearly on his own spiritual journey. It was incredible to see the faces drop in the audience—full of famous actors—because it was the ultimate counter-punch to the culture you were describing. We often imbue these values without reflecting on them, and the worst part is we pass them on to our children.
Towards the end of their lives, many people realize this chase is meaningless. They get sick, or they retire and realize life isn't what it was cracked up to be. Whether it's a founder looking for a milestone or any human being, we set these goals and eventually realize that achieving them can feel empty. Perhaps what’s more meaningful is how we go about achieving them.
What have you found regarding how successful entrepreneurs set goals? How do they measure themselves—not looking backward at the end, but throughout the journey—to keep themselves going? Especially for those who have already had a few successes and have "proven" themselves: what is the fuel they are putting into their engines now?
Jeffrey Chernick: It’s certainly a spectrum...
Jeffrey Chernick: You know, one entrepreneur who had a very large exit is already thinking about the next one because they don't want to be known for "just" one giant "B"—a billion, not a million—exit. And you're just like, "What?"
Alex: The chip on the shoulder remains.
Jeffrey Chernick: Exactly. It just depends on the person.
Alex: "I need a decacorn, not just a 'B,'" or whatever.
Jeffrey Chernick: Yeah. Then on the flip side, I mentioned Eytan with Scopely. When I bring that stuff up, he talks about his family. Every Friday night he’s with them; that’s their tradition. So, I think the greater lesson is that there is no die-hard commonality between everyone we interviewed.
In my coaching and advisory work, I feel like half my job is consistently reminding entrepreneurs that this stuff isn't that big of a deal in the long term. I tell them, "Relax." I’ve been through it so many times. I remember thinking I had to do a round of layoffs—it’s the worst feeling in the world. But you know what? You hired good people, and they’re probably going to be fine.
When you go through that enough and look back, it’s a revelation. I used to have a joke at my app, Ving—it was a video caller ID app for Android that went viral in India with 20 million users. At one point, we had to lay off a bunch of people. We joked that everyone got their dream job after Ving. The guy who loved sneakers became the head of engineering for a sneaker exchange; the person who loved scooters went to work at Bird. We were just a jumping-off point.
It took going through enough cycles to gain the perspective I have now. I remember telling my lead investor I thought we were going under. That was my ultimate fear: losing my investor’s money. He just looked at me and said, "What are we going to work on next?" It was mind-blowing.
Alex: You were thinking—and this is common to a lot of humans—"Oh my god, I’m the only one going through this shitshow." Whether it’s life, pregnancy, or a startup failing. We hold it inside because we’re embarrassed or ashamed. It’s not socially acceptable to look like you’re not "crushing it" in every part of your life. On Instagram, everyone is crushing it. On Facebook, the older generation is crushing it. On LinkedIn? Definitely crushing it.
Jeffrey Chernick: You're just watching everyone’s highlight reel.
Alex: Exactly. And then there's reality. I’m married to a French woman, and in France, the one good thing is that they do like to complain. It’s almost a "I complain, therefore I am" type of thing. There’s still a bit of ego involved there, but generally, in the world we live in, we only see the highlight reel. We don’t see the messy stuff underneath.
It sounds like the common thread among the founders you interviewed is that they developed the pattern recognition to handle the "messy stuff." But what are the tools for someone new to this journey who doesn't have an enlightened investor to tell them it’s not the end? What are your tips? One thing I love about your book is that every chapter has practical applications. Could you share some of those nuggets?
Alix Gitter: The short answer is: buy the book and you'll get all the nuggets!
Alex: All right, let's talk about that.
Jeffrey Chernick: Tell us.
Alex: First of all, this is one of the best new releases on Amazon.
Alix Gitter: Yeah.
Jeffrey Chernick: It’s number one for starting a business, number two for entrepreneurship, and number two for business culture. You can get it on Amazon, Barnes & Noble, and all the different sites.
Before we jump there, I want to mention that there is a chapter on meditation. Not everyone likes to meditate, but even if you only take two minutes to just take a break—just taking a moment to step out—it makes a difference.
There’s another chapter about being in the moment. What is the one thing in your life that makes you feel present when you do it? Is it running? Playing music? Going out and dancing? Is there a certain activity or hobby? Remember to do that thing during the hardest times because it helps create that separation; it reminds you that "this is just something I am working on—it is not me."
Alex: Right.
Jeffrey Chernick: In order to remind yourself of that, you have to find your "thing." For me, I love yoga. When I do yoga, I feel like myself again. It’s like putting your life on airplane mode for ten minutes.
Alix Gitter: Ultimately, what this book explores through Jeffrey’s stories and these successful entrepreneurs is humanity. What is the human lens through which entrepreneurship is explored? Once you see that our humanity is what connects us, you realize that while these businesses are different and your professional lives are different, the core is the same.
We explore how to bring a more human lens to entrepreneurship—being able to stay grounded and stay human. In fact, "Stay Human" is the name of our last chapter. We believe it is the way through to the next phase of entrepreneurship. We’re currently at a cultural crisis with a lot of shifts happening. What do we want to create in the future that offers stability on both a macro and micro level? We believe that supporting your life’s purpose and being the most authentic version of yourself enriches not only your life but your community, your family, and your business.
Alex: Let’s build on this. First of all, double thumbs up on meditation. I think the challenge is building the habit. Most people probably try it at some point—they download Calm or a similar app—but once the crisis passes, they feel they don’t need it anymore. They fall back into the same unsuccessful patterns.
I used to be in that category; I never really meditated. But eventually, I tried it and saw improvements. I "took a chill pill" regarding things that were stressful. Now I’m working with a coach who says that for our work to be effective, I need to integrate that practice. The theme is that the more you practice, the more space you create between an external stimulus and your reaction. It’s exactly what you were saying: creating space between external events and your self-identity or self-worth.
Let's talk about that. A present parent who doesn't overreact to a child's tantrum is similar to a founder who receives bad news but doesn't react harshly—either by taking it out on their family or chewing someone out at work. These are common patterns we follow without even noticing. The moment you start meditating, you become more self-aware. You start a journey where you realize, "Holy moly, what I thought was 'intense and awesome' was actually unconstructive and unnecessarily harsh."
Meditation is one gateway to creating that pause. What else have you found that helps these founders be better, more present humans?
Jeffrey Chernick: I would say the keyword I heard you use is "practice." That’s why meditation is called a practice. I can meditate for ten minutes and maybe only have ten seconds of actual "no thought."
Alex: Right.
Jeffrey Chernick: And the moment I’m in that ten seconds—thinking, "Oh, I’m doing it!"—the "monkey mind" returns with thought after thought.
Alex: The monkey mind, exactly.
Jeffrey Chernick: Yeah. But being able to get there for even those ten seconds is great practice, because the next time you do it, you can do more. There is a major correlation between that and being an entrepreneur. The first time you have only 60 days of runway and don’t know what to do, it’s a lot harder than the fourth time you have 60 days of runway. It becomes a practice.
Another major correlation I found between myself and these other founders is the importance of having a "mind group." People call them advisors—people around you who have been there before and have done the thing. I don't mean your college homies or your "bestie" whom you just like to talk to. I mean people who have actually done what you are trying to do.
That’s another theme: everything we’re talking about in terms of entrepreneurship has been done by someone else at some point. It might not be the exact same business, but they’ve headed in that direction. Instead of trying to hack through a mountain with a machete, find advisors in your community who can help you get there. By sharing those hard times with them, it’s like having a therapist or a coach you don’t have to pay for. You'll get the advice you need and the reminders to take space and get through it.
Alex: So, basically, find peers. Go ahead, Alix.
Alix Gitter: I was just going to say that putting everything into context is important as well. If we’re lucky, we get a hundred years here. People say this all the time, but it’s hard to totally embody.
Alex: Hold on, I’m just going to do some extra walking here while I wait to get my steps in. Okay, so if you're lucky, you get 100 years.
Alix Gitter: Yeah. And—what was I saying?
Alex: Sorry, I went for a stupid joke and interrupted your train of thought. I should have known better.
Alix Gitter: No, it’s about context. Everything is a practice, right? In these moments, you have to realize that life isn't about sustaining one feeling or one success for an entire century. It really is the journey. As corny as it sounds, the cliché is true: it’s about the journey, not the destination. Entrepreneurship isn't just about reaching the exit or launching the product. While that is the goal, shooting for that goal is what makes you feel alive and engaged. Putting the struggle into that context—realizing that the struggle is part of an enriched experience—will help people. It certainly helped us and the founders in the book.
Alex: I want to "double-click" on one idea you covered in a TED Talk: Everybody Poops. Obviously, as parents of young kids, this is near and dear to your hearts, but you meant it in the context of not being afraid to reach out to people. When you connect with someone "big," don't forget they are just as human as you are. They were kids once; they have their own traumas. They’re all humans—and they poop, of course.
I’m curious if you’ve seen that apply to the individual, too? The idea that it's okay to say, "I just 'pooped' all over myself"—metaphorically, of course. Like I just did by making fun of myself for interrupting you when I knew I shouldn't have. We need to accept that sometimes we can be an asshole. Instead of getting all messed up about it, we should realize we aren't perfect. We’re just meeting a bunch of other "poopers," and we’re "poopers" ourselves. Accepting that makes the journey more fun. Is that a pattern you've been seeing?
Jeffrey Chernick: Yes, both internally and externally. Internally, I have to accept my own imperfections—that I’m going to have my moments, have my bad days, be hungry, or be tired. Awareness is the key to change. As long as I’m aware of it, it’s helpful. But I also have to see that in others. It’s related to how we react when we don't hear back from someone...
Alex: Right.
Jeffrey Chernick: For example, I have an investor who told me they were going to give me money this week, but now they’re MIA.
Alex: I’ve been there.
Jeffrey Chernick: You start telling yourself stories about how it’s related to something you did. "Did I say something wrong? Is it my deal?" In reality, 99% of the time in my experience, it has nothing to do with me. Someone got sick, their company went under, or their funding fell through. It’s just a reminder that we’re all going through a human experience. When we take people off their pedestals, we remember that no matter who you are or how senior your position is, you have a boss. Even the CEO has a Board of Directors as a boss. If it’s not a Board, it’s the investors. It’s a cycle of humans having a human experience, and if you can continually remind yourself of that, things become a lot easier.
Alix Gitter: Yeah, and that’s the trick, right? People know these things—we know everyone is human and everyone "poops"—but having the capacity to let that truly change how you approach someone or how you deal with intimidation is the real challenge.
Alex: That’s beautiful. I’m trying to connect this to two things. First, I create stories in my head that I somehow failed because an investor isn't following up, a customer isn't signing, or—back when I was single—a girl I liked didn't respond immediately. We all do this in various phases of life. Right now, it might be, "My kids are disrespecting me," and I personalize it.
Second, in other relationships—like a founder/co-founder dynamic—you want to give the other person the benefit of the doubt. But when you have a history, you tend to repeat a negative narrative. You don't necessarily give them that benefit anymore. Often, frustrations build up because people don't talk about them. Two people who generally get along and could be productive start harboring negative stories about each other. Part of that is a defense mechanism for your own self-criticism; you start mentally criticizing the other person to compensate.
These traps don't make sense logically, but as you said, we’re all imperfect humans. What have you found regarding long-term relationships? It takes years to build a company; relationships with VCs can last longer than some marriages. Our "swipe right, swipe left" society makes it a challenge, yet we need to maintain healthy, long-term relationships to do anything meaningful.
Alix Gitter: You said it beautifully. We’re at a moment where all these incongruencies and systems that aren't working in our society are coming to a head. Being able to recognize that allows us to implement tools that support a different way of relating to each other.
There’s an amazing podcast by Esther Perel called Where Should We Begin? During the pandemic, she shifted her model; instead of interviewing romantic couples, she interviewed co-founders. What was remarkable was that the dynamics were so similar to those of a romantic couple. As you said, you really "get into it" with these people. There’s intimacy and real emotions around success, failure, and whether you're doing things right.
As for tools—again, I’ll pitch the book—but in general, I think anyone who is well-intentioned and desires to connect with their co-founder in a different way just has to decide to do it. Decide to hire a coach or someone who can help with company culture. Try approaching things differently. If you do the same thing the same way all the time and expect a different result, that’s shortsighted. You have to change it up and try something new. Jeffrey, I’m sure you have a lot to add to this.
Jeffrey Chernick: Regarding the relationship between a married couple versus co-founders: it’s all about communication. I try to convey this to every company I start or work with—there must be a culture of openness. No matter what company I’m running, I try to have one-on-ones with employees. I don't show up as "the boss"; I show up as "the homie." I want them to feel like they can tell me anything. If I don’t know what’s going on, I can't build a better company. Often, people are telling themselves internal stories about a colleague, and that’s especially dangerous with co-founders because if that dynamic deteriorates, it takes the company down with it. If something is brewing, instead of talking to everyone else about it, talk to the person you're actually in the relationship with.
Alex: Right, own the relationship.
Jeffrey Chernick: Exactly. If you can get there—and we cover this in the book—it really becomes a personal journey of emotional intelligence. I did programs like MIT, ESP, and Landmark. The core of emotional intelligence is this: when you talk to someone, don't say, "You did this" or "You did that." Instead, say, "This happened, and this is how I felt."
Alex: Right, you own your feelings. You aren't labeling them; you’re focusing on your experience.
Jeffrey Chernick: Yeah, because you can't tell me I shouldn't have felt that way. I probably learned this from my wife. I used to come at it like, "You shouldn't feel like that," and she’d say, "This is how I felt. You can't tell me how I should have felt."
Alex: I wish I had spoken to you earlier, Jeffrey, because I’ve definitely made that mistake. It's a lesson for everyone.
Jeffrey Chernick: This part of the conversation is so interesting because it goes beyond entrepreneurship. This is just about people in relationships with other people.
Alix Gitter: Which is the foundation of entrepreneurship! That’s the big "Aha!" moment. People who have been in the game for a while know this, and people about to dive in quickly learn it: everything comes down to relationships. Everything is rooted in how we relate to each other.
Alex: Unless you're building that mythical one-person AI startup. That’s the unicorn, right? Just you chatting with an AI—but that’s a whole other story. Speaking of which, you bring a lot of AI tools into the book.
Jeffrey Chernick: We didn't use AI for the editing, though!
Alex: No, but for the recommendations. My general question is this: there is so much going on every day, and founders are trying to keep up. It feels overwhelming. There is more FOMO (Fear Of Missing Out) than I’ve ever seen in my history in the tech industry. The narrative is: "Everything is going to change, everything is going to break, and nobody will have a job."
What is your take? You recommend AI as a tool, but you’ve also written a book that says, "Be more human and focus on the fundamentals." How do I combine those two ideas?
Alix Gitter: It can go either way. AI could take all our jobs; that’s a possibility. Ideally, it won't. I think it comes down to the question of why. Why are we doing this? Are we doing it just for an instantaneous result? Because that’s what AI offers.
I’ll admit, I’m a millennial—square in the middle—and I recently had to create a reel for Instagram. It took me way longer than it should have. The next one I make will probably be shorter because I’ll find an AI tool to do it for me. However, the act of creating something and exercising that creative spirit was awesome.
We pose AI as a support system to achieve your vision. It’s idyllic because if you don't have the technical skillset to execute a specific piece of your vision, AI can help you get to an MVP (Minimum Viable Product) quickly. But the broader conversation is: is that what we ultimately want as a society? I don't think we have the answer yet. For the individual with an idea, now is the time to try because you have every tool at your disposal. But I always say: don't do it alone. Partner with a human. The act of creating together feels incredible; it’s not just about the result.
Alex: So you feel more alive in the process of co-creation—the "high five" energy—than you do alone in a room?
Alix Gitter: That’s what I think. I’m sure there’s an "AI person" out there who feels differently.
Jeffrey Chernick: It’s all about the person. I’m not a solo founder; I’ve never been one. I usually partner with my closest friends. I’ve started a company with almost all of my friends at this point—I’m running out of people! Finally, it was just my wife left, so I started a book with her. That’s just my personality. People say you shouldn't partner with friends, but my communication is open enough that I can make it work successfully.
AI is an incredible co-pilot. I use it all day, every day, to execute my vision much faster than if I needed a whole team. To circle back to one of your first questions: AI removes the excuses. If you’ve been sitting on an idea your whole life, you can now create a prototype or an MVP without fundraising. You can test the market to see if it’s worth going after. In that regard, we are at the most exciting time of our lives.
Alex: Yeah.
Jeffrey Chernick: We aren't negating the potential dark paths—I’m sure there have been dark paths throughout all of human history for the centuries we’ve been doing this. And I grew up in the...
Alex: Soviet Union, so I’m well aware.
On that note, as you said, AI de-risks a lot of things by allowing you to try stuff out. For the benefit of our audience, I want to quote some of the folks you interviewed for the book.
First, Darren Berkovitz, co-founder of Telesign: "I see entrepreneurs afraid to make mistakes. They end up paralyzed by indecision. We made every mistake in the book. We hired the wrong people and didn't fire them fast enough. We had the wrong pricing and put the office in the wrong location. But the goal is to make mistakes, learn, and move on quickly." It seems AI allows you to make those mistakes even faster. I saw the same mindset from Minnie Ingersoll, co-founder of Shift: "I had ten times the learning experience running my own startup than I did at a large tech company. The intensity—the 'brain on fire' feeling—was unmatched. I had gone to business school, but nothing prepares you for being a CEO like getting your hands dirty and doing it." Then there’s the quote from Fred Krueger: "Perfection is the enemy of progress. It can hold you back and lead to trouble." It feels like the need to be right, the desire for safety, and perfectionism are the primary blocks. Your first chapter essentially says: "Lean in. Don't hesitate—go for it. There are no excuses anymore." Right?
Jeffrey Chernick: It’s all an illusion. There is no company that was born perfectly—where they came up with an idea and it was just "up and to the right" for five years straight. That doesn't exist. If it does, that’s the true unicorn. If someone says it happened that way, there’s probably a backstory we just don't know about.
It's vital to understand that in our hearts. As early founders graduate from college and look for jobs, they’re finding that the market is a bloodbath right now. What’s the path forward? The path forward is paving your own path.
Alex: Mic drop. Jeffrey, Alix, thank you so much for joining us. Everybody, please find the book—it’s called High Five Energy: A Different Kind of Founder. Buy it and apply it. What I love about this book is that it provides concrete ideas you can start using right away. You’ve heard so many great, applicable insights here today. Thank you so much for writing it and for sharing your time.
Jeffrey Chernick: Appreciate it.
Alix Gitter: Yeah, thank you.