How to win with AI: adopt it fast, admit what you don't know

Executive overview

GaryVee and Alvin Bowles of Alpha AI discuss why executives and marketers are failing to adapt to artificial intelligence — not from lack of intelligence, but from insecurity and a refusal to admit ignorance. Gary argues that technology has always disrupted incumbents and that AI is no different from electricity or the car; the only losing move is denial. The path forward is simple: download the tools, use them daily, and build context through practice before forming strong opinions. Peer communities that normalise saying "I don't know" are undervalued but critical accelerants.

The only strategy that works is radical honesty about where you actually are, combined with daily hands-on practice.

The insecurity trap holding executives back

• Senior leaders often "peacock" on AI — performing expertise they don't have — and the smartest people in the room always notice.
• Fear of disintermediation drives posturing; admitting ignorance feels like a threat to status built over decades.
• Gary compares it to good parenting: genuine humility and toning down insecurity are the prerequisite, not technical training.
• Even Gary acknowledges he is only "a couple of steps" into his AI journey and has declined panels with top AI figures because he cannot yet contribute meaningfully.
• Boards and CMOs who claim AI fluency while not using the tools are a specific problem — they know how to sell platforms but not how to get results from them.

Practice over punditry

• Gary's personal rule: the day he hears about a new tool (Midjourney, Perplexity, ChatGPT), he opens it and uses it immediately.
• Using AI daily is more valuable than consuming AI commentary or attending AI panels without firsthand experience.
• He contrasts this with his Web3 period — when he had put in deep work he was "outrageously loud"; on AI he stays quieter because he knows his current depth.
• People inside his own organisation are now deeper in AI than he is, and he is comfortable with that — it is a feature, not a failure.
• The advice for everyone: download all the major AI tools, play with them, build context, then — when ready to go all in — hire people who have actually shipped results with them.

Technology is undefeated — stop mourning disruption

• The entrepreneur who bought 10,000 horses the day before Henry Ford's factory opened is the cautionary archetype: disruption is not new and sympathy arrives too late.
• Nobody mourned the top Yellow Pages saleswoman when search engines arrived; nobody mourns the deli losing customers to a viral bagel pop-up.
• Electricity was feared as demonic; AI fear follows the same irrational pattern.
• The camera did not kill painting — both coexist as canvases of expression. AI will follow the same "and, not or" logic.
• Technology is not evil; it is a canvas. The people unprepared for it bear the cost, not the technology itself.

The power of "and" over "or"

• Binary thinking — AI is good or evil, red or blue, black or white — is the root cause of widespread anxiety and poor decisions.
• Life is "purple and gray," and leaders who demand black-and-white clarity will consistently misread emerging technology.
• Gary introduces the concept of "maybe" as an underrated operating mode: saying yes is delusional, saying no closes doors, maybe keeps optionality open and has driven much of his success.
• The AI debate is being hijacked by people who posture about bias and societal harm before they have downloaded a single app — performative concern that substitutes for actual engagement.
• Embracing "and" means accepting that AI can create new jobs while eliminating others, that experts and beginners can coexist, and that multiple tools can be right simultaneously.

Building the right community and mindset

• There is no safe, galvanised community where leaders can say "I don't know about AI" without reputational risk — Alpha AI is trying to fill that gap.
• Test-and-learn loops, not grand strategies, are how individuals and organisations build real competence.
• CMOs who have been briefed on best practices by sales teams do not understand the actual algorithm — hands-on testing reveals what the briefings miss.
• Gary's father's standard — "did we sell stuff?" — is the practical filter that cuts through performative innovation.
• The fastest path to credibility is being a practitioner and operator first, talking head second; only discuss what you have actually lived.