High Five Energy Founders

Jeffrey Chernick
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  • ENTREPRENEURSHIP

Host Jeffrey Chernick, a serial entrepreneur and investor, sits down with the world's top founders to unpack how they build, scale, and think. Featuring legendary entrepreneurs behind $200B+ in exits and IPOs—from Google AdSense to Prodege, Kiva to Telesign. Each episode reveals the pivots, failures, and mindset shifts behind iconic companies. Discover High Five Energy: the magnetic flow state where doors open, the right people show up, and opportunities align. Tools and inspiration for entrepreneurs at every stage. New episodes weekly.  Follow @H5Efounders

Episodes

  1. Raised $1.5B by Listening, Not Pitching (16x Founder)

    2 DAYS AGO

    Raised $1.5B by Listening, Not Pitching (16x Founder)

    Eric Pulier, 16x founder who has raised over $1.5 billion, reveals: He didn't pitch his way to $1.5B — he listened. The most successful companies don't come from brilliant innovation. They come from conversations with people who have real problems. From being named one of the Wall Street Journal's "Top 20 Money Losers in America" to fighting the DOJ, SEC, and NSA simultaneously, Eric shares the mindset shifts that turned catastrophic failure into serial entrepreneurship. THE REAL STORY: At rock bottom, Eric's marriage ended. He lost more money than he had. He was raising four kids — three not yet potty trained — while trying to rebuild from scratch. He'd wake at 4am, swim in pitch-black ocean, then go to the parking lot and cry before going back inside to keep building. "If I'm gonna spend this much energy feeling sorry for myself, I could put that same energy into joy and play." That mindset shift changed everything. WHAT YOU'LL LEARN: - Why the most successful companies come from conversations, not "aha moments" - How to collaborate with people who have real problems (and get them to pay you to solve it) - The pivot from victim to creator — turning depression into creativity - Why Eric believes AGI is 18 months away and what that means for founders - How he fought the DOJ, SEC, and NSA for 5 years — and won on every count - "Ship baby ship" — why getting off PowerPoint has never been more important - The difference between pitching for acceptance vs. expressing with certainty TIMESTAMPS: 00:00 Introduction to Eric's Journey 03:20 Innovative Business Models 04:31 The Rise of Digital Evolution 05:49 Navigating the Internet Boom 08:59 Lessons from Open Source and APIs 09:24 The Future of Cloud and Hybrid Solutions 09:56 Personal Reflections and High Five Energy 17:29 The Vision for Digital Identity and Tokenization 22:22 Facing Financial and Personal Turmoil 25:10 Building New Ventures 26:03 Controversy and Legal Battles 27:49 Emerging Victorious 30:17 Reflections on Identity and Purpose 35:29 The Impact of AI on Entrepreneurship 43:39 Conscious Entrepreneurship 45:22 Advice for Aspiring Entrepreneurs ABOUT ERIC PULIER: 16x founder. $1.5B+ raised. Built companies across every major tech wave from web browsers to cloud to blockchain to AI. Acquired by VMware, salesforce, and others. Creator of one of the first NFTs. Currently building at the intersection of AI, tokenization, and self-sovereign identity. GET THE BOOK: 📖 High Five Energy: A Different Kind of Founder features 18 visionary founders behind $200B+ in exits. Available wherever books are sold: https://a.co/d/iJlOfaq LISTEN ON ALL PODCAST PLATFORMS: 🎥 YouTube: / @h5efounders 🎧 Spotify: https://open.spotify.com/show/0eNPRGMGN1MM7S5bYy31Y8 🎧 Apple Podcasts: https://podcasts.apple.com/podcast/high-five-energy-founders/id1872142713 🎧 Everywhere you listen to podcasts CONNECT: 🌐 Website: jeffreychernick.com 📸 Instagram: @H5EFounders 📸 Host: @jeffreychernick 💼 LinkedIn: / jeffrey-chernick ABOUT THE HOST: Jeffrey Chernick is Managing Partner at Yellow Visor Ventures, and author of High Five Energy. He's a 3x founder (RideAmigos, Vyng - 20M+ downloads) with 20+ years building companies. Featured in TechCrunch, Forbes, NBC, LA Times. #entrepreneurship #startups #founder #AI #AGI #venturecapital #innovation #mindset #ericpulier #16xfounder

    47 min

  2. 2 DAYS AGO

    Darren Berkovitz: How to Build a $230M Company Nobody's Heard Of

    Darren Berkovitz, co-founder of TeleSign ($230M exit to BICS), reveals: The real money is in solving boring problems nobody wants to talk about. From living at home with zero external validation to protecting every major internet platform on the planet — clients paying $2 million a month — Darren built a 12-year overnight success in the unsexy world of SMS security and two-factor authentication. THE REAL STORY: Before the $230M exit, Darren spent three years hearing nothing but "no." He was living at home. No external validation. People told him to get a job. His first product lost 17 cents per transaction. But when Craigslist gave him a shot and TeleSign cut their fraud by 99% overnight — everything changed. "Find your Craigslist. Find someone who doesn't mind taking a chance on a startup." WHAT YOU'LL LEARN: - Why "boring" B2B problems are where the real money hides — and why less competition is your advantage - How TeleSign sent 30,000 cold emails per WEEK to build an enterprise sales machine with zero inbound leads - The FanDuel horror story: Why founders sold for $500M and got ZERO (liquidation preferences explained) - Why Darren coaches entrepreneurs NOT to raise VC money — and when you should - The mental health crisis nobody talks about: anxiety, depression, and a fellow CEO's suicide - How one unsigned inventions agreement nearly torpedoed a Series A - Why every single thing must be memorialized in writing — especially equity TIMESTAMPS: 00:00 Introduction to Entrepreneurial Challenges 04:10 The Birth of Two-Factor Authentication 07:28 Cold Emails and the Craigslist Breakthrough 09:23 Navigating Industry Challenges 12:13 Dealing with Outages and Security Issues 15:53 Building and Scaling the Team 17:15 Equity and Co-Founder Dynamics 28:30 VC Funding vs. Bootstrapping 30:29 The Cost of Testing Business Ideas 31:08 Hacks for Early-Stage Startups 32:02 The Reality of Raising Money 34:40 The Importance of Networking and Press 39:31 The Acquisition Journey 44:19 Mental Health in Entrepreneurship 46:58 Challenges in Recruiting and Product Development 59:13 The Importance of Documentation 01:03:10 Final Thoughts and Advice ABOUT DARREN BERKOVITZ: Co-founder of TeleSign, the company that pioneered SMS-based two-factor authentication. TeleSign protects the world's largest internet platforms and was acquired by BICS (Belgium's largest telecom subsidiary) for $230M in 2017. Darren is now an angel investor, mentor at USC's accelerator program, and serial entrepreneur building his next ventures while coaching the next generation of founders. GET THE BOOK: 📖 High Five Energy: A Different Kind of Founder features 18 visionary founders behind $200B+ in exits. Available wherever books are sold: https://a.co/d/iJlOfaq LISTEN ON ALL PODCAST PLATFORMS: 🎥 YouTube: https://www.youtube.com/@H5EFounders 🎧 Spotify: https://open.spotify.com/show/0eNPRGMGN1MM7S5bYy31Y8 🎧 Apple Podcasts: https://podcasts.apple.com/podcast/high-five-energy-founders/id1872142713 🎧 Everywhere you listen to podcasts CONNECT: 🌐 Website: jeffreychernick.com 📸 Instagram: @H5EFounders 📸 Host: @jeffreychernick 💼 LinkedIn: https://www.linkedin.com/in/jeffrey-chernick/ ABOUT THE HOST: Jeffrey Chernick is Managing Partner at Yellow Visor Ventures, and author of High Five Energy. He's a 3x founder (RideAmigos, Vyng - 20M+ downloads) with 20+ years building companies. Featured in TechCrunch, Forbes, NBC, LA Times. #entrepreneurship #startups #B2B #telesign #cybersecurity #twofactor #founders #venturecapital #bootstrap #exit #acquisition #mentalheath #founders

    1h 3m

  3. 28 JAN

    Jim Armstrong: How To Raise Money In 2026 ($750M in returns)

    Jim Armstrong, 4x Forbes Midas List venture capitalist with $750M in returns, reveals: The first meeting can NEVER end in a yes—and the strategies that actually close deals in 2026. Jim led PayPal's first institutional round, negotiated the Elon Musk merger that created the PayPal we know today, and has backed companies from seed stage to billion-dollar exits. THE REAL STORY: Before his biggest win, Jim made a bet that almost destroyed his career. He wired $20 million into Integrien across 12 bridge rounds while every other investor walked away. His partners were furious. His CFO dreaded seeing him walk through the door. "This is career suicide," they said. But Jim saw signal through the noise. VMware acquired it for $100M—returning $50M to his fund and validating what happens when you back the right product at the right time.  WHAT YOU'LL LEARN: ◼️ Why the first meeting can NEVER end in a yes (and the strategy that gets you to meeting #2) ◼️ How Jim turned PayPal's 80/20 split with Elon into 50/50 over one lunch ◼️ The "comprehensive vs. persuasive" rule that changes how you pitch ◼️ How to get introductions to investors without warm connections ◼️ What "seeing signal through noise" actually means (and how it saved a $100M exit) ◼️ Why AI is killing SaaS revenue models—and where the money's moving in 2026 ◼️ The relationship-building playbook that gets VCs to take your call ABOUT JIM ARMSTRONG: Jim has hit the Forbes Midas List four times and generated over $750M in returns. He backed NetZero ($2M to $5B public in 3 years), Integrien ($100M VMware exit), and Bridge ($500M exit). Jim co-founded March Capital (2014) and Clearstone Venture Partners (2002). He now leads Composite Ventures, focusing on the intersection of AI and brick-and-mortar retail across the $7 trillion US retail sector. GET THE BOOK: 📖 High Five Energy: A Different Kind of Founder features 18 visionary founders behind $200B+ in exits. Available wherever books are sold: https://a.co/d/iJlOfaq LISTEN ON ALL PODCAST PLATFORMS: 🎥 YouTube: https://www.youtube.com/@H5EFounders 🎧 Spotify: https://open.spotify.com/show/0eNPRGMGN1MM7S5bYy31Y8 🎧 Apple Podcasts: https://podcasts.apple.com/podcast/high-five-energy-founders/id1872142713 🎧 Everywhere you listen to podcasts CONNECT: 🌐 Website: jeffreychernick.com 📸 Instagram: @H5EFounders 📸 Host: @jeffreychernick 💼 LinkedIn: https://www.linkedin.com/in/jeffrey-chernick/ ABOUT THE HOST: Jeffrey Chernick is Managing Partner at Yellow Visor Ventures, and author of High Five Energy. He's a 3x founder (RideAmigos, Vyng - 20M+ downloads) with 20+ years building companies. Featured in TechCrunch, Forbes, NBC, LA Times. #venturecapital #fundraising #paypal #startups #founders #entrepreneurship #elonmusk #investing #angelinvesting #seedround #AIstartups #SaaS #VMware #forbes #midaslist

    46 min

  4. 26 JAN

    Eytan Elbaz: You Don't Have to Be The #1 Founder For A Huge Exit

    Eytan Elbaz, legendary LA founder and 5x entrepreneur, reveals: You don't have to be the CEO or hold the most equity to achieve generational wealth. Eytan created Google AdSense—the advertising platform now generating $40-50 billion annually—and co-founded Scopely, which sold for $4.9 billion. Named one of the Top 100 seed investors globally, he's generated billions in enterprise value. THE REAL STORY: Before AdSense became iconic, Eytan endured 3.5 years of brutal pivots and 8 failed products. The first won "Best of Show" at a major tech conference—then completely failed. Their second product brought in just $250/month, prompting an investor to mock them: "We pay our gardener more than that." But they kept building. By product #8—a revised version of AdSense—they finally cracked the code. WHAT YOU'LL LEARN: ◼️ Why being #2 or #3 on the cap table creates massive wealth with less stress  ◼️ How to navigate 8 product pivots—knowing when to persist vs. pivot  ◼️ The forced stock decision that became life-changing  ◼️ What the $4.9B Scopely exit actually felt like  ◼️ Why founders obsess over being #1 when it's not necessary TIMESTAMPS: 00:00 The Billionaire Engineer and Legendary Founder  01:37 From AMD to Entrepreneurship  02:16 The Birth of Oingo  03:00 Pitching the Idea and Securing Funding  06:42 The Reality of Building a Product  10:08 The Journey of Pivots and Perseverance  12:07 The Evolution of AdSense  18:19 The Breakthrough with AdSense  21:58 A Surprising Meeting at Google  23:23 The Acquisition Dance  29:00 The Car Ride to Monterey  31:47 The Quick Acquisition  31:59 The Surrender Experiment  33:32 The Final Deal  36:11 Life After Acquisition  39:55 Advice for Founders ABOUT EYTAN ELBAZ: Eytan co-founded Applied Semantics (acquired by Google, became AdSense) and Scopely (acquired for $4.9B). Starting from a middle-class LA family with teacher parents, he began at AMD during the first dot-com boom. After 3.5 years and 8 failed products, his team cracked AdSense—now responsible for nearly half of Google's annual revenue.  He co-founded Scopely with Walter Driver, building it into a $5 billion gaming empire. Now a top seed investor, he proves early positioning matters less than picking the right opportunities and staying in the game. GET THE BOOK: 📖 High Five Energy: A Different Kind of Founder features 18 visionary founders—including those behind Priceline, Dollar Shave Club, Tripadvisor, Natera, LegalZoom, and Kiva—who've generated $200B+ in exits and IPOs. Learn the 33 behavioral shifts that unlock High Five Energy flow state: that magnetic momentum where doors open, the right people show up, and opportunities align. Available wherever books are sold: [LINK] HIGH FIVE ENERGY PODCAST: Exploring the mindset shifts, pivots, and flow states that separate dreamers from builders. Raw stories—not the polished LinkedIn version. Hosted by Jeffrey Chernick, 3x founder, angel investor, and author of High Five Energy. LISTEN ON PODCAST PLATFORMS:  🎧 YouTube: LINK 🎧 Spotify: LINK 🎧 Apple Podcasts & all platforms: Live within 6 hours  CONNECT:  🌐 jeffreychernick.com  📸 Instagram: @H5EFounders  📸 Host: @jeffreychernick  💼 LinkedIn: linkedin.com/in/jeffrey-chernick ABOUT THE HOST: Jeffrey Chernick is Managing Partner at Yellow Visor Ventures, and author of High Five Energy. He's a 3x founder (RideAmigos, Vyng - 20M+ downloads, acquired by Siproc

    42 min
  • 4 Episodes

About

Host Jeffrey Chernick, a serial entrepreneur and investor, sits down with the world's top founders to unpack how they build, scale, and think. Featuring legendary entrepreneurs behind $200B+ in exits and IPOs—from Google AdSense to Prodege, Kiva to Telesign. Each episode reveals the pivots, failures, and mindset shifts behind iconic companies. Discover High Five Energy: the magnetic flow state where doors open, the right people show up, and opportunities align. Tools and inspiration for entrepreneurs at every stage. New episodes weekly.  Follow @H5Efounders

Information

  • Creator
    Jeffrey Chernick
  • Years Active
    2K
  • Episodes
    4
  • Rating
    Clean
  • Copyright
    © 2026 High Five Energy Founders
  • Show Website
    High Five Energy Founders