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Pursuit of Joy, Fulfillment, and Purpose

Tag: startup culture

  • Why Chris Sacca Says Venture Capital Lost Its Soul (and How to Get It Back)

    TL;DW
    Chris Sacca reflects on returning to investing after years away, emphasizing authenticity, risk taking, and purpose over hype. He talks about how the venture world lost its soul chasing quick exits and empty valuations, how storytelling and emotional truth matter more than polished pitches, and how solving real problems, especially around climate, is the next great frontier. It’s about rediscovering meaning in work, finding balance, and being unflinchingly real.

    Key Takeaways
    – Return to Authenticity: Sacca rejects the performative, status driven culture of tech and VC, focusing instead on honest connection, deep work, and genuine purpose.
    – Risk and Purpose: He argues true risk is emotional, being vulnerable, admitting uncertainty, and investing in what matters instead of what trends.
    – Storytelling as Leverage: Authentic stories cut through noise more than polished marketing. Realness wins.
    – Climate as an Opportunity: The fight against climate change is framed as the defining investment and moral opportunity of our era.
    – “Drifting Back to Real”: The modern world is saturated with synthetic hype; Sacca urges creators, founders, and investors to get back to tangible, meaningful outcomes.
    – Failure and Integrity: He shares lessons about hubris, misjudgment, and rediscovering integrity after immense success.
    – Capital with a Conscience: Money and impact must align; he critiques extractive capitalism and champions regenerative investment.
    – Joy and Balance: Family, presence, and nature are more rewarding than chasing the next unicorn.

    Summary
    Chris Sacca, known for early bets on Twitter, Uber, and Instagram, reflects on stepping away from venture capital, then returning with a renewed sense of purpose through his firm Lowercarbon Capital. His talk explores the tension between success and meaning, the emptiness of chasing applause, and the rediscovery of genuine human and planetary stakes.

    He begins by acknowledging how much of Silicon Valley became obsessed with valuation milestones rather than solving problems. The “growth at all costs” mindset produced distorted incentives, extractive business models, and hollow successes. Sacca critiques this not as an outsider but as someone who helped shape that culture, recognizing how easy it is to lose the plot when winning becomes the only goal.

    He reframes risk as something emotional and moral, not just financial. True risk, he says, is putting your reputation on the line for what’s right, admitting ignorance, and showing vulnerability. This contrasts with the performative certainty often rewarded in tech and investing circles.

    Storytelling, he emphasizes, is still crucial, but not the “startup pitch deck” version. The most powerful stories are honest, raw, and rooted in lived experience. He argues that authenticity is the new edge in a world flooded with synthetic polish and AI driven noise. “The truth cuts through,” he says. “You can’t fake real.”

    Sacca then focuses on climate as both an existential threat and the ultimate investment opportunity. He presents the climate crisis as a generational moment where science, capital, and creativity must converge to remake everything from energy to food to materials. Unlike speculative tech bubbles, climate work has tangible stakes, literally the survival of humanity, and real economic upside.

    He admits he once thought he could “retire and surf” forever, but purpose pulled him back. His journey back to “real” was driven by a longing to do something that matters. That meant trading prestige and comfort for messier, harder, more meaningful work.

    Throughout, he rejects cynicism and nihilism. The antidote to burnout and existential drift, he suggests, isn’t detachment, it’s deeper engagement with what matters. He encourages listeners to find joy in building, to invest in decency, and to reconnect with the planet and people around them.

    The closing message: Venture capital doesn’t have to be extractive or soulless. It can fund regeneration, truth, and hope, if it rediscovers its humanity. For Sacca, the real ROI now is measured not in dollars, but in impact and authenticity.

  • The Snapchat Rebellion: How Evan Spiegel Defied Zuckerberg, Dropped Out of Stanford, and Built a $130 Billion Empire

    TLDW:

    1. Move Fast: A tiny, flat design team ships ideas daily—99% flop, 1% win big.
    2. Listen Hard: User feedback turned “Picaboo” into Snapchat; perfection’s overrated.
    3. Culture Wins: “Kind, smart, creative” isn’t a slogan—it’s Snap’s DNA, guarded by “council” sessions.
    4. T-Shaped Leaders: Deep skills + big-picture thinking drive innovation.
    5. Stay Unique: AR, creators, and Spectacles make Snap tough to copy, even by Meta.
    6. Care Obsessively: Spiegel’s love for users and team outlasted crashes and clones.

    Bottom Line: Snapchat didn’t beat giants with cash—it out-cared them, proving grit and vision trump all.


    In 2013, Mark Zuckerberg came knocking with a $3 billion offer to buy Snapchat. Most 23-year-olds would have seen it as the ultimate payday—a golden ticket out of the grind. Evan Spiegel saw it differently. He said no, betting instead on a quirky app built with friends in a Stanford dorm room that let photos vanish after a few seconds. That gamble didn’t just defy logic—it redefined an industry. Today, Snap Inc., the parent company of Snapchat, boasts a valuation north of $130 billion, a user base of over 850 million, and a legacy as the rebel that outmaneuvered tech’s biggest giants.

    Spiegel, who became the world’s youngest billionaire at 25, isn’t your typical Silicon Valley wunderkind. He’s an introvert who grew up tinkering with computers, a product design nerd who dropped out of Stanford just shy of graduation to chase a dream. What started as a disappearing photo app morphed into a cultural juggernaut, reshaping how Gen Z communicates—prioritizing raw, fleeting moments over curated perfection. But the real story isn’t just about dog filters or streaks. It’s about a relentless vision, an obsession with users, and the audacity to carve a path where others saw dead ends.

    In a rare, expansive interview on The Diary of a CEO with Steven Bartlett on March 24, 2025, Spiegel pulled back the curtain on the formula that turned Snapchat from a college side hustle into a global empire. Equal parts candid and philosophical, he shared lessons from 13 years at the helm—through server crashes, copycat competitors, and the pressures of running a public company. Here’s how he did it, distilled into six principles that fueled Snap’s improbable rise:

    1. Move Fast, Ship Faster: The Power of Iteration
    Snapchat’s secret sauce isn’t genius ideas—it’s speed. Spiegel revealed that Snap’s design team, a lean crew of just nine, operates with a single mandate: ship fast, test relentlessly. “99% of ideas are not good,” he says matter-of-factly, “but 1% is.” That 1%—features like Stories or AR lenses—changed the game. The team’s flat structure, weekly critique sessions, and obsession with prototyping mean no idea lingers in limbo. On day one, new hires present something—anything—tearing down the fear of failure from the jump. It’s a philosophy born from Spiegel’s Stanford days, where he learned that waiting for perfection is a death sentence. “Get feedback early,” he advises. “Even if it’s on a napkin.”

    This ethos traces back to Snapchat’s origin. The app launched as “Picaboo” in 2011, a barebones tool for disappearing messages. Users didn’t care about security—they wanted fun. Within months, Spiegel and co-founder Bobby Murphy pivoted to photos, renamed it Snapchat, and watched it spread like wildfire. Speed trumped polish every time.

    2. Feedback > Perfection: Listening to Users
    Snapchat’s evolution wasn’t a straight line. “Your initial ideas can be wrong,” Spiegel admits. “Your job isn’t to be right—it’s to be successful.” Picaboo flopped because it misread what people wanted. Snapchat soared because it listened. Early users demanded captions and doodles; Spiegel delivered. When friends complained about iPhone camera lag, he scrapped the shutter animation, making Snapchat the “fastest way to share a moment.”

    This user-first mindset isn’t just instinct—it’s a system. At Snap’s first office, a cramped blue house on Venice Beach, tourists and users knocked on the door daily with feedback. Spiegel embraced it, turning casual chats into product gold. Even today, he roams the office, bypassing polished reports to hear unfiltered takes from the trenches. “Customers are never wrong,” he says, echoing a lesson from his product design roots: empathy drives innovation.

    3. Culture Is the Killer Feature: Protecting the Soul
    Spiegel’s biggest regret? Not locking in Snap’s culture sooner. In the early days, growth outpaced identity. “We didn’t embed it early,” he confesses. As Snap ballooned, hires from Amazon, Meta, and Google brought their own baggage, threatening to dilute what made Snap unique. Now, culture isn’t negotiable—it’s the backbone. Values like “kind, smart, creative” aren’t posters on the wall; they’re hiring filters, performance metrics, and leadership litmus tests.

    One tool stands out: council. Stolen from his artsy LA high school, it’s a ritual where teams sit in a circle, sharing raw thoughts—heartfelt, spontaneous, no hierarchy. In 2013, facing pressure to move Snap to the Bay Area, Spiegel held a council. The team spoke; LA won. “It was obvious,” he recalls. Today, facilitators run councils company-wide, stitching together a workforce scattered across continents. For Spiegel, culture isn’t a perk—it’s the moat that keeps Snap nimble.

    4. T-Shaped Leadership: Depth Meets Breadth
    Snap doesn’t reward one-trick ponies. Spiegel champions “T-shaped” leaders—experts in their lane who can zoom out to grasp the big picture. “You need depth and breadth,” he explains. A brilliant engineer who can’t empathize with marketing? Useless. A creative who ignores data? Out. This model mirrors his partnership with Murphy: Spiegel’s design obsession paired with Murphy’s coding wizardry birthed Snapchat’s iconic tap-for-photo, hold-for-video mechanic—a breakthrough that rewrote smartphone photography.

    Leadership isn’t static, either. Spiegel adapts his style per person—pushing some, coaxing others. “I’m not the same leader to everyone,” he says. “That’d be terrible.” The goal? Unlock each teammate’s potential, whether it’s a designer sketching AR lenses or a lawyer rewriting privacy policies in plain English.

    5. Be Hard to Copy: Ecosystems Over Features
    When Facebook cloned Stories in 2016, Spiegel didn’t flinch. “They’re tough to compete with,” he acknowledges, recalling early investor skepticism. But Snap didn’t win by outspending—it outbuilt. Features like disappearing photos were easy to mimic; ecosystems weren’t. Spectacles, launched in 2016, flopped initially but evolved into a developer-driven AR platform by 2024. A billion monthly public posts from creators and a thriving ad network followed. “Build things that are hard to copy and take time,” Spiegel advises. “That’s how you survive.”

    The Meta-Ray-Ban partnership in 2023 stung—he’d pitched Luxottica on Spectacles years earlier, only to be ghosted—but it reinforced his resolve. Snap’s independence, he argues, proves you can outlast giants by staying weird and user-obsessed.

    6. Care More Than Anyone Else: The X-Factor
    Above all, Snap’s rise hinges on one trait: care. “How much you care is the biggest predictor of success,” Spiegel insists. It’s why he and Murphy slogged through a three-day server crash in 2012, convinced users would abandon them, only to see them return. It’s why he rejected Zuckerberg’s billions, believing Snap could stand alone. It’s why, at 34, he still geeks out over design critiques and user quirks.

    That care isn’t blind passion—it’s disciplined obsession. Spiegel’s love for Snap’s community (850 million strong) and team (thousands worldwide) fuels sleepless nights and tough calls, like layoffs that left him ashamed. “I feel a huge responsibility,” he admits. But it’s also what keeps him going. “If you don’t love it,” he warns entrepreneurs, “you won’t survive.”

    The Rebellion That Rewrote the Rules
    Snapchat didn’t win by being first—Facebook, Twitter, and Instagram came before. It didn’t win with endless cash—Meta’s war chest dwarfs Snap’s. It won by out-caring, out-iterating, and outlasting everyone else. Spiegel’s story is a middle finger to conventional wisdom: you don’t need a degree, a billion-dollar runway, or a monopoly to build something massive. You need grit, a user-first lens, and the guts to say no to $3 billion when your gut screams “not yet.”

    At 34, Spiegel’s not done. Snap’s emerging from a “two-year winter” into an “early spring,” he says poetically, with green shoots in its ad platform and creator growth. Spectacles 5.0 hints at an AR future he’s chased since 2016. And while he swears he’d never start another tech company—“It’s way too hard”—his curiosity and care suggest otherwise. For now, he’s steering Snap into its next act, proving the rebellion’s just getting started.