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High Five Energy Founders

High Five Energy Founders

Written by: Jeffrey Chernick
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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.

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© 2026 High Five Energy Founders
Economics Leadership Management & Leadership
Episodes
  • Jim Armstrong: How To Raise Money In 2026 ($750M in returns)
    Jan 28 2026

    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

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    46 mins
  • Eytan Elbaz: You Don't Have to Be The #1 Founder For A Huge Exit
    Jan 26 2026

    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

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    42 mins
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