Jeffrey Chernick is a 3x founder, advisor, angel investor, and former Wall Street wealth manager. Author of "High Five Energy: A Different Kind of Founder" — featuring 18 legendary founders behind $200B+ in exits and IPOs. Host of the High Five Energy Founders podcast. COO of Kabuk, a Japan travel concierge. Managing Partner at Yellow Visor Ventures. Previously founded RideAmigos (leading commute management platform) and Vyng (20M downloads, 5B videos played across 170 countries, acquired by Siprocal). Featured in 30+ media outlets including TechCrunch, Forbes, and the LA Times. Inventor of 21 US Patents. 3x Emory Goizueta Business School Alumni Luminary and advisory board member at Pepperdine University's Entrepreneurship MBA Program.
Alix Gitter is a writer, actress, and co-author of the bestselling business book, High Five Energy: A Different Kind of Founder. Originally from the world of professional acting, Alix discovered that the structure, resilience, and creative essence required in the arts are the exact same tools needed to build a successful company.
As a "co-founder of a family" and a business partner to serial entrepreneur Jeffrey Chernick, Alix brings a vital "human lens" to the often-rigid world of tech and startups. She specializes in helping leaders move away from "dirty fuel"—motivation rooted in fear and external validation—toward a practice of authenticity and community impact. Her work focuses on the intersection of emotional intelligence, storytelling, and the sustainable pursuit of a life’s purpose.
📱 Apple Podcasts | 🎧 Spotify | 🔗 iHeart
1. The Rollercoaster of Success: Why Every Founder Needs "High Five Energy"
Jeffrey is a "serial founder" (someone who starts multiple companies), while Alix comes from an acting and writing background. They explain how they combined Jeffrey’s business "hacks" with Alix’s creative storytelling to turn a dry business manual into a book about the human experience of entrepreneurship.
The speakers highlight a surprising connection: both actors and founders have to build their own lives from scratch. Whether you’re auditioning for a role or pitching to an investor, you are essentially an entrepreneur trying to turn an idea into a reality.
Jeffrey and Alix argue that most business books only show the "winning" moments. They wanted to focus on the pivots—the times when a founder had to change direction entirely. For example, they share that the technology behind Google AdSense only succeeded after eight different failed attempts.
One of the most important lessons discussed is the psychological toll of failure. Using the example of a successful company that collapsed during the COVID-19 pandemic, the authors emphasize that your worth as a person isn't tied to your company’s bank account.
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.(Jeffrey Chernick)
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... that actually extends into the entrepreneurial space as well. (Alix Gitter)
2. Beyond the Billion-Dollar Exit: Finding Your "High Five Energy"
More Than Just a "Unicorn"
The speakers critique the common narrative that "success" only means massive wealth or "unicorn" status (a billion-dollar valuation).
The Holistic View: Alix explains that true success includes building a stable business that supports a family, helps a community, and allows the founder to grow as a person.
Net Worth vs. Self-Worth: A major theme is the need to separate your value as a human being from the ups and downs of your business. Alex notes that being a good parent or spouse is just as much a metric of success as being a CEO.
The Philosophy of "High Five Energy"
Jeffrey introduces the core concept of their book: High Five Energy. Unlike traditional "manifestation" (just thinking about a goal), this is about feeling the result.
The "Feeling" State: It’s about tapping into the physical energy you feel when you land a big sale or help an employee succeed.
The Ripple Effect: When a founder leads with this positive, connected energy, they tend to attract the right people and opportunities at the right time.
"Dirty Fuel" vs. "Clean Fuel"
Alex brings up a powerful distinction in what drives ambitious people:
Dirty Fuel: Motivation rooted in fear, insecurity, or a "chip on the shoulder" (common in many high-achievers and immigrant stories). While it can get you started, it often leads to burnout and unhappiness.
Clean Fuel: Motivation rooted in purpose, creativity, and the joy of building something that thrives—much like raising a child.
First off: how you do one thing is how you do everything. (Jeffrey Chernick)
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. (Alix Gitter)
3. The Soul of the Startup: Why Your "Why" Matters More Than Your Exit
The Trap of "Worthiness"
Alix shares a poignant observation from her background in the acting world that mirrors the startup grind. Many people chase fame or a billion-dollar "exit" because they believe that once they reach that milestone, they will finally be "enough."
The "Dirty Fuel" Cycle: If your motivation is rooted in fear—the fear of not being loved or being a failure—no amount of money will ever satisfy you.
The Jim Carrey Moment: Alex references a famous speech by Jim Carrey that poked fun at this exact phenomenon: the idea that even after winning two Emmys, you’re just chasing the third one to feel valid.
Purpose Over Projections
The speakers argue for a shift toward "clean fuel"—motivation born from a genuine desire to solve a problem or help a community.
The Investor’s Perspective: Jeffrey shares a life-changing moment when he confessed to a lead investor that his company might fail. Instead of anger, the investor simply asked, "What are we going to work on next?" * The Human Connection: For the most successful and grounded founders, the "win" isn't the bank balance; it’s the ability to have Friday night dinner with family or seeing a laid-off employee find their dream job elsewhere.
Lessons for the Long Haul
The takeaway for any creator or founder is to gain perspective. Jeffrey’s "High Five Energy" philosophy suggests that while business moves in cycles, your inherent worth does not.
How You Do One Thing is How You Do Everything: Whether you are raising a child or leading a team, the energy you bring to the room matters more than the final spreadsheet.
Success as a Jumping-Off Point: Even "failures" are often just transitions to the next great thing for everyone involved.
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?" (Jeffrey Chernick)
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. (Alix Gitter)
4. The Soul of the Startup: Why Your "Why" Matters More Than Your Exit
Escaping the Highlight Reel
Alex points out that between Instagram, LinkedIn, and Facebook, everyone looks like they are "crushing it" 24/7. This creates a dangerous sense of isolation for founders who are actually struggling.
The Reality Gap: Most people are embarrassed to admit when things are messy.
The "Pattern Recognition" Secret: Experienced founders aren't necessarily smarter; they’ve just seen the "messy stuff" enough times to know it’s normal and not the end of the world.
Practical Tools for Sanity
Jeffrey and Alix share "nuggets" from their book, High Five Energy, specifically aimed at people who don't have a mentor to guide them through the dark days:
The "Airplane Mode" Activity: Find one thing—whether it’s yoga, running, or playing music—that forces you to be 100% present. This reminds your brain that you are a person first and a "founder" second.
Micro-Meditation: Even two minutes of stepping away can create a "buffer" between a stressful event and your reaction.
The "Space" Between: Alex notes that meditation isn't just about relaxation; it’s about creating space so you don't overreact to a child’s tantrum or a bad business email. It transforms "unconstructive intensity" into thoughtful leadership.
The "Stay Human" Manifesto
The episode concludes with a look at the final chapter of their book, titled "Stay Human." * Authenticity as Stability: In a world of constant cultural and economic shifts, the most stable thing you can hold onto is your own life's purpose.
A Collaborative Future: By being the most authentic version of yourself, you don't just help your business; you enrich your family and your entire community.
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." (Jeffrey Chernick)
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. (Alix Gitter)
5. The "Monkey Mind" and the Power of Being Human: A Guide to Sane Success
Taming the "Monkey Mind"
Jeffrey explains that both meditation and entrepreneurship are practices, not things you "perfect."
The 10-Second Win: Meditation isn't about clearing your mind for an hour; it’s about those few seconds of peace before your "monkey mind" (the constant chatter of thoughts) takes back over.
Building Business Muscle: Just like meditation, handling a crisis gets easier with practice. Dealing with a cash shortage for the fourth time is less terrifying than the first because you've developed the "pattern recognition" to know you can survive it.
Your "Mind Group" vs. Your "Besties"
A major tip for founders is to build a circle of advisors who have actually walked the path before.
Don't Use a Machete: Instead of hacking through a mountain alone, find people who have already built the trail.
The "Free" Therapist: Sharing your struggles with peers who understand the specific stress of a startup provides a level of support that friends or family might not be able to give.
The "Everybody Poops" Philosophy
The speakers dive into a surprisingly grounded metaphor for dealing with high-stakes business: Remembering that everyone is human.
Taking People Off Pedestals: Whether it’s a billionaire investor or a famous CEO, everyone has bad days, gets sick, or faces pressure from a "boss" (like a Board of Directors).
Don't Take "MIA" Personally: If an investor stops texting back, Jeffrey reminds us that 99% of the time, it’s about their life—a family emergency or a internal funding shift—not something you did wrong.
Owning Your Mess: Success involves accepting that you will occasionally "poop the bed" (metaphorically). Accepting your own imperfections makes the journey less about reaching a perfect destination and more about enjoying the ride.
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.(Jeffrey Chernick)
Life isn't about sustaining one feeling or one success for an entire century. It really is the journey... Putting the struggle into that context—realizing that the struggle is part of an enriched experience—will help people. (Alix Gitter)
6. The Relationship ROI: Why Emotional Intelligence is the Ultimate Business Hack
The "Co-Founder" Marriage
Alix points out a fascinating crossover between business and romance. She references research showing that the drama between business partners is almost identical to the drama between married couples.
The Intimacy of Business: You share money, stress, success, and failure. If you don't manage the relationship, the company will collapse from the inside out.
Breaking the "Negative Narrative": In long-term partnerships, we often stop giving people the benefit of the doubt. We start telling ourselves "stories" about why a partner is annoying or failing, rather than actually talking to them.
Tools for Better Connection
Jeffrey shares a simple but life-changing rule for communication that he learned from his marriage and applied to his startups:
Own Your Experience: Instead of saying, "You did this wrong," try saying, "When this happened, I felt this way." * The "Boss" vs. The "Homie": Jeffrey advocates for a culture of radical openness. He suggests having one-on-ones where you show up as a peer, not a superior, so employees feel safe telling you the truth before a small problem becomes a crisis.
Stop the Gossip: If you have a problem with someone, talk to them, not about them.
Humans in the Age of AI
With all the hype and "FOMO" (Fear of Missing Out) surrounding AI, the speakers offer a grounded perspective:
AI as a Tool, Not a Soul: While the book recommends using AI for efficiency, the authors insist that the "fundamentals" of being a person—empathy, presence, and connection—cannot be automated.
The Antidote to Overwhelm: In a world where "everything is changing," the most stable thing you can invest in is your ability to relate to other people.
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. (Jeffrey Chernick)
Everything comes down to relationships. Everything is rooted in how we relate to each other... That’s the foundation of entrepreneurship! (Alix Gitter)
7. The Death of Excuses: Launching Your Dream in the Age of AI
AI: Your Co-Pilot, Not Your Replacement
The speakers address the "cultural crisis" surrounding AI with a refreshing take: use it to handle the boring stuff so you can focus on the human stuff.
Removing the Technical Barrier: Jeffrey points out that AI "removes the excuses." You no longer need a massive team or millions in funding to build a prototype. You can test an idea in a weekend, de-risking the entire process of starting a business.
The Joy of Creation: Alix emphasizes that while AI can give you "instant results," the real value is in the process of creating. She argues that co-creating with other humans—experiencing that "High Five Energy"—is what actually makes us feel alive.
The "Messy" Path to Success
Alex shares wisdom from some of the iconic founders featured in the book (like the creators of Telesign and Shift) to debunk the myth of the "perfect startup."
Mistakes are the Goal: Success isn't about avoiding errors; it’s about making them quickly and learning. The founders interviewed admit to hiring the wrong people, picking the wrong office, and messing up their pricing.
Perfection is a Trap: As guest Fred Krueger notes, "Perfection is the enemy of progress." The biggest thing holding most people back isn't a lack of talent—it's the desire for safety and the fear of being wrong.
Paving Your Own Path
With the job market feeling like a "bloodbath" for many new graduates, the speakers offer a powerful "mic drop" moment: If you can't find a path, pave your own.
The "Brain on Fire" Feeling: There is no business school on earth that can teach you as much as "getting your hands dirty" and running your own project.
Don't Do It Alone: Even in a world of solo AI tools, the most successful journeys are shared. Jeffrey's secret to success has been partnering with friends and family, proving that open communication is the ultimate competitive advantage.
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." (Jeffrey Chernick)
The act of creating together feels incredible; it’s not just about the result. (Alix Gitter)
Check the episode's Transcript (AI-generated) HERE.
To continue the conversation with Jeffrey Chernick and Alix Gitter, connect with them via https://www.jeffreychernick.com/high-five-energy.
Find their book on Amazon.
Other Episodes
Godard Abel | CEO of G2
S 01 | Ep 6 Where You Go for Software: Reach Your Peak
Dean Stocker | CEO of Alteryx
S 01 | Ep 8 Turning Your Customers Into Your Biggest Champions
Peter Fader | Co-Founder of Theta CLV
S 01 | Ep 10 Turning Your Marketing Into Dollars
AUTHOR
.png)
The fastest way to build digital experiences. We empower businesses to convert PDFs, presentations and other content into interactive experiences & webpages with instant branding, analytics & more
.png)
