Secret salons, oyster happy hours, coffee raves–San Francisco is back and basking in idyllic weather as rent increases jump to the highest in the nation. Streets are teeming with people racing to events, despite tech season being weeks away, when conferences like Dreamforce, Disrupt, TedAI and SF Tech Week take over the city.
Much of the frenzy is being attributed to the AI gold rush with people returning to town to get a piece of the action, so over the past week I popped into several happenings to hear what everyone is talking about.
Finding your tribe
At AGI House, a sprawling Hillsborough mansion just outside of San Francisco, known for hosting tech celebrities like Google cofounder Sergey Brin and Grimes, dozens gathered for a garden gala featuring talks with industry luminaries OpenAI’s chief strategy officer Jason Kwon and former OpenAI interim CEO Emmett Shear. It was as insider as it gets with a pulsing DJ set by Twitch cofounder Justin Kan, meticulously curated by AGI House founder Rocky Yu and Icons podcaster Melanie Uno.
In the mix was Poshmark cofounder Manish Chandra who shared with me his views on the AI transformation. I asked, what will people do with their lives as AI frees up time, and more importantly how will they pay for it.
He replied, “I feel like we’re moving to more and more abundance, even though the path to abundance always feels a little uncertain and dark.”
“When the dot com boom was crashing, it was impossible to find a job. Highway 101 was emptier than Covid. There were see-through buildings, literally no jobs, and people were throwing in the towel.” Trying times, he recalled. “I remember it from a personal perspective, because I had young kids and had to figure out how to survive.”
He expressed how hard times bring out things that can transform you, whether you discover superpowers or connect with new people. “Human connections deepen when times are tough,” he said. “When times are good, people just kind of ignore each other.”
He also said there have been far crazier boom and bust cycles that have come before, with companies giving away BMWs and other outrageous perks to attract engineers.
“In the nineties, technology was changing so fast, it felt like everything you were doing was going to become obsolete, literally every day,” he said. “Every 10 years, we predict the demise of Silicon Valley, and we feel like whatever the technology is coming is dooming humanity, and is more severe than last time. Yet here we all are thriving, sitting here this lovely evening.”
Emmett Shear, now cofounder of Andreessen-backed AI alignment lab, Softmax, sat down with me to discuss how people can best keep their head straight during these times. He explained that in the seventies there was a seminal work authored by Alvin Toffler, called Future Shock, that explored the psychological disorientation that can occur as a result of rapid technological change.
“This feeling of overwhelm, that if things keep changing, I can’t learn fast enough to keep up with the system,” he said. “But the way you keep up is actually by giving up on trying to understand everything at that level of detail.”
He then shared his barbell strategy for surviving the next five years.
“In a high variance environment where things can change a lot in unexpected ways, you should just YOLO big things that might work, because even if you fail, your tried-and-true plan could also fail. So there’s no point playing it safe, might as well be ambitious,” he advised. “On the other hand, as things get riskier, you’ll need to build up safety and reliability support to counterbalance.”
He said hunter-gatherers lived in the same situation we’re wandering into, a world of forces more powerful than themselves and beyond their control. Not only was it spiritually, emotionally and intellectually beneficial to be in a tight community, but also economically sound. When you store meat from the hunt in the bellies of friends, they’ll be around to help when you find yourself in a tough spot.
Futureproofing AI bets
Back in San Francisco, at a Michelin starred restaurant where the meal was served community style making dining optional, AI unicorn Honeybook gathered the press to discuss how AI is birthing a new breed of one person startups and solopreneurs.
It was here I had a chance to talk with Jeff Crowe, managing partner of Norwest Venture Partners, who told me the story of a 20-year old founder that landed seed funding to create text-to-sheets, text-to-deck apps right before ChatGPT made it a feature. This led to the question, how can VCs futureproof bets to prevent obsolescense in the age of AI.
He said the first thing to look at is product. If it’s a thin wrapper around a core, it’s hard to futureproof as the LLMs eat their way further into the application layer. “It’s how venture capital looked at personal software in the nineties and said what’s the differentiation if Microsoft moves into the space. Thirty-plus years later, it’s a similar phenomenon in AI products, where OpenAI, Anthropic and others keep adding functionality.”
As far as defensible moats, he looks for product capabilities not easily disruptable like those with domain-specific data, integration with large enterprise systems, and bespoke distribution tied to supply chain. If it’s a product that’s been around longer, he looks for how fast it’s pivoting to AI, driving into core functionality as well as operations including development, customer support, sales, marketing, HR and finance. Because if operations aren’t futureproofed, competitors can gain a superior cost structure and become more capital efficient and profitable. He looks to see whether customers are adapting because some are going to get accelerated, and others obliterated, with risks that have nothing to do with the core business. Lastly, he looks for a culture that’s nimble and can move exceptionally quickly.
A fan of young talent, Crowe believes hiring AI-natives is the best way to transform an organization, because their rate of change is less than a worker whose baseline is pre-AI.
Embracing AI workers
Across town, Initialized Capital was hosting its own press dinner, introducing their portfolio of agentic startups deploying digital workers.
Runway cofounder Siqi Chen told me from the moment he launched his startup in 2020, he knew they’d never have more than 100 people, because they had early access to GPT-3 and knew they could scale faster with AI, than headcount.
In contrast to Crowe’s hiring strategy, Chen said, Runway is hiring only senior talent. “The profile of how we hire is quite different today than it was even three or four years ago. It’s staff or principal level only at this point, because junior stuff can basically be done by LLMs today.”
“We’re seeing non-technical people contribute on a technical level like never before– tagging a robot to write the code for a bug–that’s just magic,” he said. Runway uses bots for everything, from qualifying leads to reviewing documents.
One of Initialized other portco commented that they deployed AI in Slack for IT support under the name of Paul, not AI Paul. A bit head-spinning to think you can be chatting with an AI colleague and not know it, even if they are funny.
Initialized Capital’s managing partner Brett Gibson said it’s the natural progression of where we’re heading.
I asked him whether this was the end of the app economy. He replied, “Software is going to trend towards being generatable. There are going to be a lot of apps you still want a relationship with for a variety of reasons, because they have other people on them and you’re collaborating, or perhaps the AI itself has a personality you want to interact with. It’s not going away, it’s just going to have to adapt.”
And what about humans, I asked, what’s next for humans?
“The one thing that makes me very hopeful is that if there’s anything AI is very good at, it’s personalized education. And so hopefully, that will be the path for those feeling left out. People should follow whatever they’re interested in and curious about because a high agency person using high leverage tools are going to do something cool and that’s valuable,” he said.
AI gets the last word
Back at AGI House, hanging out with hashtag inventor Chris Messina, I asked what advice he would give Gen Alpha on where to focus their energies, considering how pandemic losers have become AI winners, with ballet dancers, hair stylists and bartenders the few trades AI can’t replace.
“VCs are over, SaaS is over, everything that’s been going on for the last 10 or 15 years kind of doesn’t really make sense anymore,” he replied. “If you really want to invest in the future, it’s about having a perspective, being able to bring people into that and creating movements.”
Echoing what Chen said: “There’s only one Mr. Beast–and so if you develop relationship as a brand, that becomes sustainable value because AI cannot replace brand.
Or can it?
ChatGPT, may have no defensible moat as an AI assistant, but as a cultural icon with an estimated 1 billion followers, it remains pretty much untouchable.
Just like the city from which it came.
