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Do you share your innermost thoughts with ChatGPT? You might want to think twiceor at least change your settings fast.
Category:
E-Commerce
Fintech firm Mercury recently dropped some data that made me smile. It ranked the top five coffee shops powering founders in San Francisco based on actual transaction data: Sightglass, CoffeeShop, Equator, Saint Frank, Ritual. I’ve built Octolane with my cofounder, Rafi, from every single one of them. But here’s what the data doesn’t show: the $500,000 investment term sheet I negotiated over a cortado at Cafe Réveille. The $800,000 deal I closed while sitting next to a grad student cramming for finals. The three customers who became friends, then advocates, then our biggest champions, all because we met first over coffee, not Zoom. When I was in high school, I cleaned offices at night, empty offices with ergonomic chairs and standing desks and those motivational posters about “innovation.” Meanwhile, I’m building an AI company worth millions from a wobbly table at a coffee shop, and somehow this feels more real, more honest than any corner office ever could. The distributed office isn’t dead, it just moved to cafés. I wake up at 5 a.m. here in San Francisco, because those three hours before the city stirs are mine. I review what our AI models learned overnight. I write. I think. Then I head to whichever coffee shop matches my energy that day. Saint Frank when I need to focus, since it’s quieter, more intimate. Sightglass when I want that productive hum of energy around me. Equator when I’m meeting someone for the first time and want them to feel comfortable, not intimidated. Rafi, my cofounder and CTO, moved internationally to build this with me. One of our engineers handles the front end from one continent, another tackles the back end from another. So why would I pay $8,000 a month for an office in SoMa (the neighborhood South of Market Street) when I can spend $200 a month on lattes and have the entire city of San Francisco as my workspace? What I’ve Learned Building in Public (Literally) The serendipity factor is real. Last month, I was debugging a particularly nasty prompt engineering issue, trying to get our AI to detect deals in Gmail without false positives. I was muttering to myself (yes, I’m that guy) when someone at the next table leaned over: “Are you working on LLM classification?” Turns out hes an AI researcher at Anthropic. Twenty minutes later, I had a completely new approach that cut our error rate in half. You can’t engineer that in a conference room. Practical wisdom. Keep your screen visible enough that interesting work attracts curious people, but angle it so you’re not broadcasting sensitive customer data. The sweet spot is showing code or product UIs, technical enough to spark conversations with the right people, general enough to protect privacy. Investors are humans too. The $500,000 investment I mentioned? It happened because I was at Réveille at 3 p.m., and so was he. We were the only two people there. We chatted and he learned more about what I was working on. I showed him our productnot a deck, not a demo, just the actual thing, running, solving a real problem. He saw me working, grinding, building. The next day, the term sheet came through. Later he told me: “I invested because youre willing to be different and bold to stand out.” What he didn’t say, but I know mattered: Other founders had already told him about the guy who’s always at Réveille, laptop open, building. And when he left that day, I was still there. Midnight founder cafés are a thing now: late-night coffee shop takeovers where founders and engineers gather to build, network, and fuel up on free caffeine, and big AI companies are leaning into it. Cursor’s been running “Café Cursor” pop-ups across San Francisco, New York, Stanford, even Guadalajara, taking over coffee shops for a day, giving out free coffee and those coveted keychains, merch thats shaped like the tab keyboard key (a nod to the keystroke that accepts Cursor’s AI suggestions). Anthropic did a weeklong Claude Café pop-up in New York City’s West Village that drew more than 5,000 people, with their “thinking” hats becoming so viral that people claimed they flew across the country just to get one. These aren’t permanent cafés, they’re pop-up experiences. But that’s exactly the point. They’re recognizing what we already know: The best AI work happens in liminal spaces. Not quite work, not quite social. Somewhere in between. That’s where the guard comes down: You’re not pitching, you’re just talking. And the person debugging next to you might casually mention the fix you’ve been stuck on for a week. And it goes deeper than corporate activations. There’s a founder in the Mission District of San Francisco who literally opened his house as a café after midnight. Just for founders. No tourists, no meetings, just people building. I’ve been there twice. Both times, I left with ideas I couldn’t have found anywhere else. The only AI company that’s actually opened a permanent café? Perplexity, in Seoul. But even they get it! They put a podcast studio and a single computer running their search engine in the basement. The coffee shop isn’t the product. The community is. The Practical Reality (Because Romance Only Gets You So Far) Here’s what they don’t tell you about the coffee shop life: You need three spots minimum. One for deep work (quiet, consistent Wi-Fi, you know the outlet situation). One for meetings (good acoustics, professional-ish vibe, not too loud). One for when the first two are full or you just need a change. Noise-canceling headphones are nonnegotiable. But here’s the thing: I don’t always use them. Sometimes I want to hear the ambient noise, the conversations, the espresso machine. It reminds me that I’m building something for real people, not just for the AI models or the pitch deck. Your burn rate matters. Every dollar matters. An office in San Francisco costs $5,000 to $10,000 minimum. That’s a month of runway. That’s an engineer. That’s 100-plus customer acquisition attempts. So yeah, I’ll take the $5 latte. Time-of-day strategy is everything. I’ve mapped it out. Early morning: Saint Frank or home (deep work, model review, writing) 8 a.m. to noon: Sightglass or Equator (customer calls, team syncs) Noon to 3 p.m.: Avoid peak lunch chaos, take meetings walking or find a quieter spot 3 to 6 p.m.: Ritual or CoffeeShop (energy picks back up, good for creative work) After 6 p.m.: Usually home, but the midnight café if I need the founder energy What Building from Coffee Shops Taught Me About AI There’s a parallel here that keeps itting me: AI works best when it has context. Every engineer here is building on the idea that AI should understand the full context of your communication, not just isolated data points. Coffee shops give me context. I see how people actually work. I hear what founders are struggling with. I feel the energy when someone closes a deal or the deflation when funding falls through. You can’t get that from a dashboard or a user interview. You have to be there, in it, living it. When I’m prompt engineering at 9 a.m. at Saint Frank, watching the barista dial in the espresso, I’m thinking about patterns. About how humans and machines both learn through repetition, through feedback, through context. The best prompts I’ve written came from coffee shops. The best features we’ve built came from problems I overheard someone complaining about two tables over. The deeper insight is that building in isolation makes you optimize for the wrong things. You optimize for elegance, for technical beauty, for what impresses other engineers. Building in public, literally surrounded by your users, keeps you grounded in what actually matters: Does this solve a real problem for a real person? Building from coffee shops keeps me honest. I can’t hide behind the performance of “founder working in office.” I can’t pretend to be productive when I’m not. If I’m stuck, I’m stuck in public. If I’m building, I’m building where people can see the mess, the mistakes, the reality. We’re trying to replace Salesforce with Octolane. That’s aggressive, maybe delusional. But I’ll tell you this: I’d rather chase it from a coffee shop in the Mission, surrounded by other founders equally delusional and equally committed, than from a sterile office where everyone pretends to have it figured out. How to Actually Make This Work If you’re thinking about ditching the office, here’s what I wish someone had told me: Map your energy to your spaces. Don’t just pick a coffee shop because it’s close. Figure out what work you do best where. I write best at quieter spots. I sell best in energetic spaces. I code best with moderate ambient noise. Become a regular somewhere. Not everywhere, somewhere. One spot where they know your order, where you have your table, where you’re part of the ecosystem. For me, it’s Réveille. That consistency matters when everything else is chaos. Respect the space. Buy something every two to three hours. Tip well. Don’t monopolize tables during peak times. The coffee shop isn’t your free office, it’s a business that’s subsidizing your dream. Honor that. Build relationships, not just networks. That Anthropic engineer? We’re friends now. The investor? We get coffee every few weeks. The other founders? We text each other when we’re heading to a spot. This only works if you’re actually present, actually human, actually building relationships. Know when to go home. Sometimes you need silence. Sometimes you need privacy. Sometimes you need to take a call that can’t happen in public. Don’t force it. The coffee shop is a tool, not a religion. The Launch Is Coming I’ll probably launch our product from a coffee shop. Maybe Saint Frank, maybe Réveille, maybe that midnight café in the Mission. My team will be distributed across the country, asleep in some time zones, working in others. And somehow, we’ll pull it off. Because the best work doesn’t happen in offices. It happens where life happens. Where the coffee is strong, the Wi-Fi is reliable enough, and the person next to you might just have the insight that changes everything. Mercury’s data showed the top five coffee shops powering SF founders. What it didn’t show is why. It’s not the coffee. It’s not even the Wi-Fi. It’s the reminder that you don’t need permission to build something great. You just need conviction, a laptop, and a table. See you at the café.
Category:
E-Commerce
Gen Zers, who were practically born with smartphones and iPads in their hands, have grown up completely immersed in the information highway. Therefore, it should come as no big surprise that those born as digital nativesdeeply connected to culture, trends, politics, and businesshave different ideas about what their contributions to the world should look like. They deeply value work-life balance and they need to feel like the work they do has meaning. Globally, they are the generation most concerned about issues like corruption and inequality. They’re striving to create changeand they’re committed. Still, Gen Zers often get called out for being entitled, lazy, or simply not being driven. However, according to a recent conversation between executive Garry Ridge, former CEO of WD-40, and Simon Sinek, author and thought leader, it’s not a lack of commitment or drive that sets Gen Z apart in the workplace. It’s a well-earned lack of trust in leadership. On his podcast, A Bit of Optimism, Sinek posed a question to his guest about why Gen Z seems to work backward when compared to past generations. Contrary to the old playbook, where employees were expected to work hard and showcase their commitment before getting a raise, a promotion, or other payout, Gen Z needs to see the reward up front. “That could be interpreted as entitlement,” Sinek said. “I understand it as they grew up in a world where there’s no loyalty from the company.” Basically, if a company doesn’t have an employee’s back, should the employee really be expected to hustle for said company? Gen Z doesn’t think so. In his conversation with Sinke, Ridge agreed, noting that the logic is completely understandable, given the generation’s deep distrust of big business. Ridge asserted that companies shouldn’t dismiss these young employees as lazy or unmotivated. Rather, they should work with them to build that essential trust, providing more frequent and clear-cut steps to move up the ladder. “Once upon a time you had these reviews where you were actually looking backward. Well, maybe now the way to go is having steps along the way so you can recognize performance, Ridge said, using the example of giving employees the opportunity to earn accolades by having check-ins every couple of months to assess performance. Further, Ridge and Sinek agreed that year-end reviews aren’t a great stepping stone, either. And, from that lens, maybe Gen Z is spot-on when it comes to phasing out the old system. “I don’t want to wait 364 days for you to tell me what I should’ve done better or how good I’ve done,” Ridge explained of the Gen Z mindset. “What I want to do is be coached along the way.” Call them lazy and entitled all you want, but Gen Zers, many of them having watched their parents work hard their whole lives with little to show for it financially in their later years, don’t want to hustle without a clear payout. Honestly, who could blame them?
Category:
E-Commerce
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