The Truth About Your Energy, Insecurity, and That Thing You've Failed at for 10 Years

Could Superman’s rookie card be the next blue-chip asset?

I walked away from this conversation feeling oddly optimistic about two things I never expected to care about: cartoon characters and patience. What felt like offhand banter quickly became a coherent thesis on culture, markets, and how attention shapes value. Gary’s pitch is deceptively simple — nerd culture’s collectibles are entering the same orbit as sports cards — and he makes a persuasive case for paying attention now rather than later.

Why fictional characters are suddenly investable

The most surprising part? The argument that a Tweety Bird card can have a rookie moment like a Jordan basketball card. Gary traces a cultural collision: Comic-Con collectors are meeting the trading-card crowd at conventions, liquidity is increasing, and a new class of collectors is forming. He points to examples, admits to personal buys, and shows a patience that turned a dropped Ronaldo card into a 6x gain. I liked how candid he was about volatility — flipping can win big or blow up — and how he frames patience as the underrated superpower of modern collectors.

From pantry to pitch deck: Creatures of Habit and democratized investing

When Michael Chernow takes the mic, the conversation pivots from cardboard to breakfast. Creatures of Habit — a high-protein overnight oatmeal and soon a plant-based protein bar — illustrates the kind of small, operational brand that attracts creator-investors. The startup’s StartEngine campaign becomes a practical lesson: crowdfunding tools let fans become investors, and that changes the dynamics between founders and communities. Gary’s anecdote about DMing his way into partnerships felt like a reminder: access is social, not solely credential-based.

Gender, grit, and the meritocracy myth

Gary’s take on women in entrepreneurship hit a mix of empathy and impatience. He argues for parity in expectations — treat founders like players on a court — while acknowledging real bias exists. What I appreciated was the bluntness: he refuses to let perceived inequality become an excuse to underperform. Instead, he insists on market meritocracy: the product decides, not pedigree. He also calls out insecurity as the real constraint, urging women (and men) to stop wasting time on those who don’t believe in them.

Practical pep talks — from loneliness to chasing a pop-star dream

Two audience moments stuck with me. One caller fretted about sitting alone at a table; Gary’s answer was both harsh and human: be your own biggest fan, show up, and try. Another was Melanie, a 23-year-old from the Philippines who wants to join a pop girl group. He refuses to accept “draining” as a reason not to pursue a dream. Instead, he prescribes a hybrid life: do the steady job, use nights and weekends to rehearse, and leverage that double grind as fuel rather than exhaustion. His advice felt practical — not motivational fluff — and rooted in lived trade-offs.

When to quit (and when tenacity wins)

I braced for nuance about quitting and got a zinger: ten years is too long to stick with something that’s failing. Gary’s rule-of-thumb is mercilessly human — he’s willing to endure pain, but not eternal sunk-cost pity. That felt liberating. He champions controlled tenacity: know how long you’ll give something and set a horizon. Persistence is overrated when it’s a ritual of denial; persistence is powerful when it’s informed and time-boxed.

Scarcity, awareness, and the modern art market

On visual art and mystique, Gary made a short, sharp point: awareness creates scarcity, not the other way around. It’s counterintuitive but convincing. The Mona Lisa isn’t valuable because it’s secret; it’s valuable because so many people know it exists. Marketing and scarcity are not enemies — they’re partners in the creation of cultural value.

A personal takeaway

I left feeling energized and slightly unsettled. Energized because the creator economy continues to invent real marketplaces where everyday obsession becomes capital. Unsettled because this means decisions matter more than ever: what you collect, whom you support, how you allocate time. The throughline of the conversation was clear — build, choose, and iterate with curiosity and urgency. That’s not just advice for collectors or founders; it’s a small manual for modern life.

Reflective thought: What if our hobbies are the early indicators of tomorrow’s markets — and our willingness to chase them decides who wins?