Sean (@smacmannis) header
Sean (@smacmannis) profile picture

I help technical products make sense to markets. Product marketing, positioning, launches, commercialization. Ex-Pinterest + Gitcoin. SF.

San Francisco, CA
Joined December 2008
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The easier life gets, the more people will pay to do hard things.
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the internet concentrated ownership in a handful of giant platforms. AI could concentrate even more value, or push it back toward users and builders. i’m much more interested in the second future. more ownership more open systems more upside for the people creating the value
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Your career should not be owned by an employer. Your identity should not be owned by a platform. Your AI context should not be owned by a model provider.
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The internet made information abundant. AI makes intelligence abundant. The next generation of infrastructure won’t be about generating more intelligence. It’ll be about proving where it came from, who contributed it, and who should benefit.
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If AI leads to this future then maybe we’ll all be OK
People often ask where Lovable users find time to build side projects. What I'm seeing: people are choosing to build instead of passive consumption, like endless doom scrolling. Creativity is reclaimed from consumption.
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Vibe coding works. Vibe coding your design? Not so much. Met @yarik_designer through @patel0phone while working on @AtriumAcademy. First thing I did as VP Marketing in my last role? Hire him to build our brand foundation. Now we’re building Tribe together. Something we keep seeing: Founders can ship product faster than ever. But they’re still showing up like an MVP. And that gap kills trust. Not because the product is bad. Because the presentation says “not ready.” Most teams think design is polish. It’s not. It’s the difference between “this project is interesting” and “this company gonna blow up.” Getting v1 design done is easy now. Building something that actually holds across product, site, and marketing is not.
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Hot take from @impranavm_ at the Digital Frontier Summit at UC Berkeley: “AI agents right now are basically toys that adults over 25 are playing with.” He’s probably right. But agents themselves aren’t the interesting part. They’re the apps of the AI internet. What matters is the infrastructure underneath. Builders today are racing to figure out: identity permissions payments guardrails But almost no one is asking the deeper question: Who owns the context those agents operate on? Because once agents remember your preferences, goals, relationships, and history… they stop being tools. They become personal intelligence. If platforms own that context → AI becomes the strongest lock-in ever created. If individuals own it → AI becomes open infrastructure. That’s the real battle for the next internet. Who's working on that? DM me.
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if AI makes context the real control layer, what has to exist so individuals retain real leverage instead of all the value compounding to platforms and employers?
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people should not have to rebuild their digital mind every time they switch tools, jobs, or platforms
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Right now in AI: Platforms own your identity. Platforms hold your memory. Platforms run the agents. So the intelligence acting on your behalf runs on context you don’t control. The obvious architecture is the opposite: Users own identity. Users own memory. Agents plug into that. Maybe working in blockchain just red-pilled me. But building “personal AI” on platform-owned memory feels a lot like rebuilding the same old internet… just with better autocomplete.
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i concur. this is a good reason.
if you ask most peeps why they want kids they’ll give you some npc answer. the reason why i think having children would be amazing is that you get a front row seat to consciousness booting up. like watching an os that god wrote light up for the first time. & as they grow up you get to examine the world through an innocence lens you basically shedded a long long time ago.
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vibe coding is how people start noticing where the control points are
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I started my career in ad tech because I believed in the open internet. Back then the web felt like a real market. Publishers had supply. Advertisers had demand. Open exchanges connected them. Then the internet closed. Platforms captured identity, data, distribution, and monetization. The market layer disappeared. Over the past few years I’ve found myself drawn to people trying to reopen parts of the system — crypto networks, DAOs, programmable ownership, public goods funding. Now AI is forcing the same question again. Who controls the infrastructure of intelligence? If models, distribution, and agents live inside a few companies, we may repeat the same story we saw with social platforms. But there’s another path: • open models • local AI • interoperable agents • programmable ownership systems I’m starting to spend more time talking to founders building what I’d call the economic infrastructure of the open internet. Working on open AI, ownership systems, or coordination infrastructure? If so, I’d love to compare notes.
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The underrated hire is whoever understands the customer and the market. Airbnb saw this early when they merged PM and PMM in 2023. Product advantage now = speed. Fewer people. Faster decisions.
the most underrated hire right now is a great product person. when i say product person i'm def not talking about a product manager. perhaps i think there has to be somewhat of a new role. i don't have a good name for it yet but maybe something like "product thinker".. someone with an intuitive grasp of the product as it exists, where it's soft, where it sings, & how to iterate it toward something even sharper. in some sense, this person has to cohesively hold in their head where this product should be 2 years from now & work backwards from that. i say this cuz when building was hard, engineering was the bottleneck & the status hierarchy often reflected that. building is no longer hard. which means the variance in outcomes has shifted almost entirely to judgment on what to build, how to sequence it, & how to talk about it. & the story matters as much as the thing. internally, it organizes the team around a shared model of why. externally, it shapes the interpretive frame users bring to their first experience. you can't retrofit narrative onto a product & expect it to land, it has to be load bearing from the start. the rarest version of this person sits at the intersection of culture & deep technology. someone genuinely bilingual. they know what's technically possible & they know which cultural currents are real vs. ephemeral. that combo is what separates products that feel inevitable from products that feel assembled. before ppl clap back with this person has always been valuable, i know.. i am just saying now they might be the most *important* person in the room. their value compounds like never before.
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neither of those seems right to me... the AI wave is a big one, but it's more a continuation than anything else... software is still eating the world, it's just eating a lot more labor right now
was at a party this week & i was having a convo with a guy who said hiring is hard in sf because there are roughly two types of people right now.. those who won’t leave their job because they know the market’s brutal & those who think this is the last window to get rich building something. one side is playing defense… risk off, clinging to safety because they’ve seen friends laid off, etc. the other side smells the blood. ai changes everything, & the next generation of giants gets built in famine not feast. it’s fear vs urgency. both very rational in many ways. fascinating dichotomy.
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Were we lied to though? I say we as a partner of a strong woman, a son of another, a girl dad, and a long-time advocate for gender equality. I don’t think we were lied to by Sophia and Sheryl. I think we just didn’t get the full picture. Sheryl Sandberg didn’t promise that hard work would override biology. Sophia Amoruso wasn’t saying that resilience could replace systemic support. What they did offer was a kind of permission: to want more. To push back on the idea that ambition made you less of a woman, or that you had to choose between power and partnership. What got lost was everything else—the infrastructure we never built, the conversations we never had, the emotional costs we never factored in. And now that grief is bubbling up, often in moments that feel deeply unfair: an IVF cycle that doesn’t work. A partner who wants to support but doesn’t know how. A system that cheers on women’s ambition but offers no margin for the rest of life. I’ve tried to show up differently. I cook, do drop-offs, have structured my career for flexibility, said no to jobs that would cost me time with my kids. Not because I’m some kind of hero—but because I believe in a shared story. I believe we’re all better off when no one has to carry the whole load alone. So no, I don’t think we were lied to. I think we were told a hopeful story. One we now get to revise—together—so it reflects the whole messy, human truth. And all of us have a part to play.
The hardest part about going through IVF is the letting go part. My entire life has been defined by grit, hard work, and resilience. Someone like me statistically should not be where I am today without defying the odds. Born to a rural farmer's boy in China, went to a non-target school, and worked my way up from customer service in tech. But with IVF I can't work harder, push myself, or optimize my body more in this process. My entire conditioning is working against me. I spent my 20s working at elite institutions, trying to act like a man. Pixie hair cut and androgynous clothing. I listened to Sheryl Sandberg and drank the Lean In Kool-Aid thinking I would have more time and deferred my personal life and family planning for my career. Now in my 30s I'm feeling so much grief for believing I could have it all. I know each cycle and every body is different. The journey is not over...but man, we were so lied to by the Girlboss and Lean In era.
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Fun experiment from @p_millerd using @metalabel_ to get his book out there. I have the physical copy on my bedside table, but good to add the digital collectible as well 😀 Spreading Good Work is good work!
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picked up one of these today. epic collector number you know, for the memes. excited to check it out.
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we can see the progress
Tomorrow marks the 100th day of my administration. San Franciscans want change. They want accountability. They need to know City Hall has their back. It’s not political to want to feel safe walking your kids to school, opening a business, or having clean streets. We started working before Inauguration Day—and haven’t stopped since. For the first time in five years, people feel San Francisco is headed in the right direction. I’m incredibly proud of what we’re building, but I’m not satisfied. And I’m going to keep walking and talking to people each and every day, until public safety and public faith have been restored. What I’ve learned in these first 100 days is you can’t solve what you can’t see. That’s why when I call impromptu, on-site meetings about street conditions, we get better plans—and better results. Tent counts are now at their lowest since 2019. To rebuild trust and public safety, we must rebuild our foundation and create the conditions for economic success. Departments must stop working in silos. Everyone must own the outcome. And we are making progress. ➡️Street encampments are dropping. ➡️Violent crime is down 15%. ➡️Car break-ins are at a 22-year low. ➡️Hotel bookings are up 50% from last year. Companies are also betting on San Francisco. Databricks is investing $1 billion. Zara is expanding with a flagship store. Nintendo is coming to Union Square. We have 80 more AI office leases expected this year. People are betting on San Francisco again. But we cannot bank on temporary fixes. We must invest in permanent solutions for our economic success as we dig ourselves out of the nearly $1 billion budget deficit we inherited. Over the last 100 days, we have started to break down the invisible wall that has existed between the two sides of City Hall for decades. That's how we got to: ➡️A 10-1 vote on the Fentanyl State of Emergency Ordinance. ➡️A new unified approach to street response, replacing nine disconnected teams. ➡️A policy shift requiring individuals to accept treatment, counseling, or connections to services to receive sterile drug use supplies. ➡️A clear path to 1,500 new shelter and treatment beds. And we’re tackling housing. We passed legislation to convert empty offices to homes, advanced our Family Zoning plan, and launched PermitSF to cut red tape. In May, we’ll introduce more reforms to make it easier to build housing and run a small business in San Francisco. The people of this city don’t just want change—they want to help make it happen. This is an all-hands-on-deck moment. I love this job, and I love this city. My expectations for success are sky-high. And what’s driving me is that I know yours are too. The people who have committed their lives to this city, the families who are enrolling in our public schools, the businesses fueling our neighborhoods, the elders who want to feel safe again on our streets—they are tired of a City Hall that does things to them instead of with them. San Franciscans want to live in a city they feel proud to call home. And we are going to deliver. Together, we can win, and we will. Let’s go, San Francisco. We’ve got work to do.
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great transparency & execution by @dvassallo. love the bold move to bring this further into the @gumroad fold
Small Bets is joining Gumroad! Yes, I sold Small Bets. I’m going to keep running it myself, but Gumroad is now the 100% owner. It’s a good deal for me, and it should only bring more benefits to the community. Details - $3.6M sale price. - 50% cash / 50% stock options. - Cash payment in 2 parts: $900K received last week, $900K in 12 months. - My options vest in 10% increments every 6 months. - I will continue to run Small Bets for 5 years. If I quit, I lose any unvested options. - I will also be helping part-time to make Gumroad better. - I won't take any salary*. My goal is to help Gumroad (the company) become a $10M profit/yr business and make my equity return a $200K+/yr dividend. * technically my state of WA is forcing Gumroad to pay me a minimum wage of $69,500/yr, but I’ll use that to exercise my options. Valuation - Gumroad had already acquired 10% of Small Bets last year for $500K. - $3.6M for 90% = $4M valuation. - Small Bets made almost $500K in profit last year excluding Gumroad fees. Based on 2024 earnings, this sale would represent an 8X profit multiple. Under the Gumroad umbrella, we expect to grow this business to $1M in profit within the first 2 years, which would be a forward-looking 4X profit multiple. Future - I will continue running Small Bets myself as its own autonomous subsidiary. Basically, nothing changes. I still decide what happens there. Of course, that could change in the future but Small Bets has had 41 consecutive cash-flow positive months, and if that performance continues I see no reason for me getting kicked out. - Payment processing is likely becoming a race to the bottom, almost a commodity nowadays. Gumroad wants to be doing more than just payments to remain a valuable business. - The goal is to eventually turn Gumroad into a community rather than just a payment processor, where new and aspiring entrepreneurs get help starting and succeeding with whatever they want to do, even if it doesn’t involve using Gumroad’s products. The plan is still fuzzy, but that’s the direction. Small Bets will act as a laboratory for these ideas. - Small Bets has already shown the value of a support network and how having people with first-hand experience in your corner can help beyond what any AI or piece of software can. We will try to scale this concept further so that Gumroad can help creators with much more than just payments. - And if you’re one of the 6,692 lifetime members of the Small Bets community, thank you so much for trusting me and supporting my project. You will continue to benefit from all the goodness we’ll add following this partnership. Ask me anything!
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