Gary Vee Says the Smartest Investors Are Going Analog
TL;DR
Gary Vee thinks AI will make analog assets more valuable, not less — he argues the next decade is a “barbell” where extreme AI creates extreme demand for physical retail, restaurants, concerts, collectibles, sports, and even things like drive-in movie theaters.
The real opportunity isn’t complaining that AI lowers the bar — it’s asking what new scarcity it creates — Gary’s answer is that scrappiness just moves somewhere else, whether that’s photographers shifting into new premium services or entrepreneurs building businesses around trust, community, and in-person experiences.
He says most big brands are still wasting marketing budgets because they haven’t adapted to a mid-funnel world — his blunt take: marketing departments waste “93 cents of every dollar,” while the winning play is to spend roughly 20% of total budget on organic social production and then promote what already works.
TBPN’s own growth story reinforces Gary’s old advice: start ugly, go hard, and publish everywhere — the hosts credit Gary’s early push to go multiplatform with YouTube, Instagram, and a newsletter, even if the early content felt “subpar,” because the compounding kicked in early.
Alternative sports are one of his biggest analog bets because AI can’t replace live human stakes — he pointed to investments in pickleball, Unrivaled’s 3-on-3 league, whiffle ball, sailing, slam ball, and padel as examples of assets that benefit from decentralized media and can’t be disrupted by synthetic content.
He’s also quietly bullish on live social commerce, with China as the warning shot — Gary says China will do $1 trillion in GMV this year through social selling, and argues TikTok Shop, Meta, and YouTube are all positioned to make live commerce a major consumer-business shift in the U.S.
The Breakdown
From “womos” to a real growth lesson
The interview opens with Gary doing what Gary does: riffing on “womos,” short for “word combos,” tossing out mashups like “quirky + niche” before the hosts pivot to a sincere thank-you. They credit him for pushing TBPN early to “go harder” and, more importantly, go multiplatform with YouTube, Instagram, and a newsletter — even when the content was rough. Gary’s point is simple and very on-brand: everything starts subpar, and with distribution now basically free, not playing the attention game is “uncomprehendable.”
Live content is still early, even if it feels old
They talk about how strange it is that livestreaming can feel both mature and still underbuilt, despite Twitch, Ustream, and years of precedent. Gary says it’s “always the beginning,” and the hosts give a concrete example: a daily live cooking show with a real set, multiple cameras, a fixed time, and guests could still become a serious media business. The format isn’t the moat by itself — breaking through is still hard — but they both see huge open space if creators add just a little more production and consistency.
AI lowers the bar online — so where does the edge move?
The hosts bring up GPT image tools and how they’ve basically democratized high-quality product photography, erasing one old signal of entrepreneurial competence. Gary doesn’t deny the flood is coming; he says everyone will soon be able to make video, image, and audio at a level that would have seemed absurd a few years ago. But his historical framing is the interesting part: electricity, typewriters, computers, mobile, open source, social, and now AI all reshuffle advantage, and the scrappy people don’t disappear — they just redeploy that scrappiness somewhere new.
The big thesis: extreme AI creates extreme analog
This is the core of the episode. Gary says he sees a “barbell” where the faster AI advances, the more people crave physical, trustworthy, tactile experiences: retail, events, venues, restaurants, flip phones, vinyl, and collectibles. He even talks about wanting a restaurant where you check your phone at the door and sit at communal tables, because within five years he thinks people may not trust “a single video” online without wondering if it’s fake.
Why vinyl, collectibles, and backlash matter
Asked about vinyl surpassing $1 billion in annual sales, Gary says the explanation is both decorative and deeper: yes, some people want wall art or collectibles, but a lot of this is a subconscious pushback against infinite digital feeds. He connects that same dynamic to consumer backlash when big brands use obvious AI creative — mentioning companies like McDonald’s getting heat — because people are scared AI will take their jobs and they react emotionally. His larger belief is optimistic: humans self-correct better than we give ourselves credit for.
Sports, the Sphere, and other analog assets that AI can’t disrupt
When the conversation shifts to Josh Kushner looking at the Giants and the success of the Sphere, Gary’s answer is basically: yes, and more of it. He says decentralized distribution and AI-proof entertainment are exactly why he’s spent the last six or seven years investing in alternative sports like pickleball, Unrivaled, whiffle ball, sailing, slam ball, and padel. Then he gets more imaginative, sketching out ideas like someone building 39 modern drive-in theaters or rolling up 900 local restaurants into an experiential chain that beats private equity’s old assumptions.
Books, MasterClass, and a brutal take on wasted marketing spend
There’s a lighter detour through Ryan Holiday, Ryan Serhant, and Gary’s belief that people often write their best book first and last — first because they have a lifetime of observations stored up, last because they finally have the wisdom to synthesize it. From there he plugs his MasterClass, framing it as a practical alternative to taking on $300,000 in MBA debt. He closes with the sharpest line of the interview: big-company marketers are wasting “93 cents of every dollar” because they still guess at top-funnel campaigns and old-school lower-funnel tests instead of investing heavily in organic social production for the “midfunnel” world.
One last warning shot: live commerce is real
Right as the segment is ending, Gary insists they barely touched one of the biggest shifts ahead: live commerce. His headline number is that China will do $1 trillion in GMV this year through social selling, and he says TikTok Shop is already proving the model in the U.S., with Meta and YouTube likely to follow. His punchline on whether TikTok’s future owners would need to subsidize commerce is pure Gary: “You only need to subsidize shitty [stuff].”