The Silicon Valley Brand Problem
Why the most important skill in tech is one nobody is talking about + our startup comedy show.
👋 Hi friends,
Living here this week has been surreal, with the Knicks taking the championship in five games. Their first title in 53 years.
When I told my friends and family I’d be moving to New York in 2020, they said it was a mistake. But to be honest, New York is the only place I’ve ever lived where reality exceeded my expectations. I grew up in China, watching every movie set here, convinced it was the most exciting place on earth. Now that I’ve met the people, built the things, and lived through the sheer randomness of it all, it's somehow exceeded every expectation.
I’m excited to share the events we’re hosting in the coming weeks … A startup comedy show with tech comics you’ve seen on the internet, breakfast with the founder of Zynga, and a rooftop party to kick off the summer.
📅 Upcoming Events
June 23 | 💼 The Shortlist: June Founder Showcase (NYC) – Meet the founders of the breakout startups in New York who are hiring.
June 25 | 🚀 Founder Breakfast w/ Mark Pincus, Founder of Zynga (NYC) – I’m inviting two dozen founders for breakfast and an intimate Q&A with Mark.
June 25 | 🎤 Strong Opinions, Loosely Held: Startup Comedy Show (NYC) – Seven of tech's funniest voices on stage to rant about whatever in tech is driving them insane. A true startup comedy show featuring tech comics.
June 30 | 🍽️ Extraordinary Founders Dinner (SF) – Hosted at one of the few Michelin-starred steakhouses in the country, known for Japanese A5 Wagyu. EXTREMELY LIMITED SPOTS.
June 30 | 🌇 June Tech Rooftop Mixer (NYC) – All friends in tech welcome. Join us for sunset views, conversations, and cocktails on the most beautiful rooftop in New York.
July 28 | 🍽️ Junto Founder Dinner (NYC) – Curated for founders and CEOs only who have raised venture capital or have significant traction.
November 5–6 | 🗽 Outliers Summit (NYC) – A gathering of ambitious people building extraordinary things. Learn from the uncommon paths behind success. Hosted by Andrew Yeung and Ankur Nagpal. Apply for early access!
• • •
Ask yourself how many people you know who switch between ChatGPT, Claude, and Gemini month to month.
The answer is most of them. Everyone is switching back and forth, constantly, to the model with the best perceived product value. There is zero brand equity.
Would anyone pay more to use ChatGPT if they thought it was just as good as Gemini because they love the brand? Probably not. That means it has no brand equity.
This is a problem nobody in Silicon Valley is talking about.
• • •
Before tech, I spent the first chapter of my career in advertising and brand.
At 15, I worked at what I thought were illustrious brands: Levi’s, Nike, and J. Walter Thompson, one of the world’s largest ad agencies at the time. I was starstruck by Mad Men and wanted a taste of the life.
While I was there, I learned the true meaning of “brand.” And the importance of it. For example, did you know that Fortune 500 companies have a line item on their balance sheet to quantify the value of their brand? Firms like Interbrand publish annual rankings of what those brands are worth. Apple’s brand alone is valued at over $500 billion, separate from the company’s products, cash, or real estate.
One time I was in a meeting with the CEO of J. Walter Thompson Asia, Tom, and someone asked what the definition of “brand” was. I never forgot his answer.
He said: “It is the long-term relationship between a customer and a company.”
Fast forward to today. If there is one thing I’ve observed from spending time around Silicon Valley CEOs and tech founders, it’s that so few talk about investing in brand beyond the initial conceptualization, design, and website build. I think this is a mistake. Here’s why.
• • •
(1) Product excellence is not enough
The AI “startups” of today will be the generational companies of tomorrow. Look at how the modern-day stack of tools is changing from Microsoft Excel, Outlook, and Gmail to ones like Wispr Flow, Gamma, and Perplexity. Everything from how we communicate with colleagues to how we find information on the internet to how we talk with loved ones is evolving.
But product excellence alone won’t cut it. The velocity of product development is extraordinary, yet everyone is building the same thing, leading to a fiercely competitive market flooded with identical, commoditized products. Having the best objective product no longer guarantees market dominance.
(2) People don’t trust AI companies
Simultaneously, trust in AI is at an all-time low. There is a massive disconnect between Silicon Valley and the rest of the world, and most aren’t paying attention.
People do not like AI.
A YouGov survey in late 2025 found that 35% of US adults report using AI at least once a week, but only 5% say they completely trust it.
Ask the regular consumer. Most people do not want agents, digital twins, or OpenClaw poking around in their lives.
(3) We are losing touch with brand marketing
Think back to the David Ogilvy era of enduring brands like Patagonia, Starbucks, and Hershey’s. The brands that make people feel emotion, belonging, and deep trust. Think about the campaigns we still talk about decades later. Volkswagen’s “Think Small” in 1959. Nike’s “Just Do It” in 1988. Dove’s “Real Beauty” in 2004.
You don’t see work like that coming out of tech anymore.
The reason is that companies today are addicted to performance marketing: paid Instagram ads, Google search marketing, paid social. Every dollar attributable down to the click. CFOs love it.
But the issue with overoptimizing for this is that these are transactional touchpoints. People click, download, maybe try the product. Then they forget the brand instantly.
Performance marketing is investing in the next six months. Brand marketing is investing in the next three to five years.
• • •
The cost of overlooking brand
I talk to my friend Lindsay Kaplan about this all the time. She’s the co-founder and former chief brand officer of Chief, the billion-dollar networking company for executive women, and was the first hire and VP of brand at Casper.
I asked her what happens when companies overlook brand. Here’s what she told me:
“I think of performance marketing like a crash diet. You see results quickly, but it’s rarely sustainable. Brand, on the other hand, is how you build a healthy company. It creates trust, preference, and memory. It lowers long-term acquisition costs and improves retention. It gives people a reason to choose you even when products start to look increasingly similar.”
She continued:
“It’s also a misconception that brand only pays off in the long term. Done well, it’s accretive in the near term too. Clear positioning sharpens conversion. A strong narrative improves word of mouth. A distinct point of view makes every channel work harder. The challenge is that this kind of work takes time, judgment, and real talent. It’s much easier to buy clicks than to build conviction.”
That last line is the one to remember. It is much easier to buy clicks than to build conviction.
• • •
A simple exercise to bring this all together.
Look at today’s top LLMs: ChatGPT, Claude, Gemini. People switch between them constantly, chasing whichever one wins this week’s benchmark.
Brand equity is the premium a customer will pay just for the brand. Right now, every frontier AI product has roughly zero.
Historically, early-stage startups didn’t talk about brand because they didn’t have the money to. But the early-stage AI companies of today are not normal early-stage companies. They are the best-capitalized startups in history. They have generational war chests and the shortest window in tech history to use them.
The companies that win the next decade of AI won’t have the best models. The models will all be roughly the same. They’ll have the best brands.
If I were starting an AI company today, I’d hire a head of brand before my second engineer.
• • •
📌 Andrew’s Bookmarks
My favorite links to help you be wiser and more creative.
Your Most Improbable Life by Kevin Kelly – The less predictable you are, the less likely you are to be replaced by AI. Machines are efficient, and they are powered by the predictable. Strive to be a category of one, and to live the most improbable life you can
How to make people trust your brand by Tom Orbach – Related to today’s post! For decades, marketing had a cheat code: capital. You could use it to be seen (TV, billboards), to be first (R&D, development), to look good (packaging, branding), and to be good (product quality, talent). But today, AI can do all those things. So what is the new moat?
Sparkly people and how to find them by Anson Yu – The five people you spend the most time with define you. Here’s how to curate them with sparkly people.
• • •
💃 Tech Community Plugs
Resources for entrepreneurs, investors, and tech professionals.
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🧮 Need a CPA? I’ll introduce you to Alex, with whom I’ve been working for the past three years. He’s excellent and specializes in tax support for high-earning individuals and entrepreneurs. More info here.
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🚀 Have a startup idea you’re considering building? Builders Between Ventures is a 3-week validation sprint with Forum Ventures’ AI Studio to pressure-test your thinking, understand the market, and get clarity on whether it’s worth pursuing. And then pitch them for $250k! Apply here.
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💸 Fundraising – Are you raising capital? Get your startup in front of my network of 2,000+ top-tier VC investors, angel investors, and family offices. Sign up here.
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What other perks should I include? Let me know.
• • •
💸 Affiliates
Founders, make $$$ by booking calls!
Over the years, I’ve partnered with VC-backed software companies that will pay you to take a 30-minute call with their sales team. If you’re a founder or CEO, you probably qualify for most of these.
Block off one day, take a dozen calls, and walk away with $$$. I call it Uber Black money. All you have to do is take the call.
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Ordinal ($200) – The most powerful end-to-end platform for drafting, planning, and scheduling social media content. Trusted by 1,000+ modern marketing teams.
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🖼️ Behind the Scenes
Last week, we hosted Tech Extravaganza. It was one of my favorite events we’ve ever thrown. Over 1,000 people came out!
We turned an entire floor into a casino. Another floor: a content recording studio, vibe-coding lounge & arcade. And the rooftop into a live music stage.
It took an absurd amount of work to pull off. Huge thank you to our Head of Events, Maks, who made it all happen.
