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Bootstrapped a profitable company from a dorm-room startup to a $58.5M acquisition by…
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Blaine Vess shared thisThe market has already decided who wins the first phase of AI. Infrastructure. The Goldman Sachs chart in this post says it plainly. AI infrastructure stocks have roughly doubled since December 2023. Software has gone the other direction, dropping well below its starting point. Mega-cap hyperscalers sit somewhere between the two. Equity gains have concentrated in semiconductors, hyperscalers, data center operators, hardware providers, and power companies. The average infrastructure stock in Goldman's basket returned 44% year-to-date, against a 9% increase in consensus earnings estimates for the same group. The market was rewarding infrastructure even before the earnings justified it. The logic is straightforward. Infrastructure captures value before anyone knows which applications win. You do not need to pick the right AI model, the right software company, or the right use case. You just need to own the pipes every one of them runs through. Goldman's buy list reflects exactly this: Cloudflare, CrowdStrike, Palo Alto, Oracle, Microsoft. What they share is not a marketing message about AI but a structural position. You cannot run an AI system without compute, cloud infrastructure, cybersecurity, or data storage. Demand for those services rises as AI usage grows. Software will eventually catch up. The applications will find their footing, revenue will follow adoption, and the multiples will recover. But the market is telling you something important right now: in a period of genuine uncertainty about which AI bets pay off, capital flows to whoever gets paid regardless of who wins.
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Blaine Vess shared thisThis image from Y Combinator is gold. I have sat across the table from founders who genuinely believed their LOIs were revenue. I have seen pitch decks where GMV was called ARR with a straight face. Nobody corrected them because everyone in the room wanted the number to be real. The confusion is understandable in the early days. You are trying to signal traction before traction fully exists, and the lines between interest, intent, and actual money can feel blurry when you are moving fast. But the moment you stop being precise about what you actually have, you start making bad decisions about hiring, spending, and how long your runway really is. The hierarchy in this YC framework is about intellectual honesty with yourself. An LOI is a conversation. A booking is a promise. A run rate is a projection. MRR is the only number that tells you what your business is actually doing today. Know which one you have before you say the word revenue.
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Blaine Vess shared thisThis is quite funny but also smart. Someone hit 90% of their Claude session limit. Their fix: ask Claude to write a summary so GPT can pick up where it left off. One AI briefing another AI so the work can continue. Microsoft recently shipped a feature where GPT drafts a research report and Claude reviews it for factual accuracy and citation quality before the final output reaches the user. So at the enterprise level, the two are already being made to work in sequence officially. Honestly, some of the best workflows are discovered by someone who just needed to get something done.
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Blaine Vess shared thisHaha, you can easily tell which companies are using AI to write their communications. AlphaSense tracked the sentence structure "it's not just a ___, it's a ___" across corporate news releases, earnings reports, and government filings. That construction went from roughly 50 mentions in 2023 to over 200 uses in 2025, more than quadrupling in two years. The CEO of AI detection firm Pangram put it directly: "The prevalence of AI content is growing rapidly and 'it's not just X, it's Y' is a tic preferred by 2025-era frontier language models." The moment you outsource the actual thinking in your communications, you have outsourced your credibility. Investors and operators who read enough of this stuff can feel when a human is not behind the words.
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Blaine Vess shared thisThere is no such thing as being late in your own life. Every business I have ever seen that mattered started at a different time than every other business that mattered. The founders who built something real were not early or late. They were just moving when they were ready to move. The comparison trap is where ambition goes to die. You are not behind the person who raised their seed at 27. You are building something different, under different conditions, on a different timeline. The boats that take longer to leave are usually the ones built to carry more weight. Keep rowing.
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Blaine Vess shared thisEvery generation fears the new machine will take all the jobs. Every generation is eventually wrong. Jensen Huang has been saying this consistently for two years. His view is simple: we are at the beginning of a new industrial revolution, and there will be more people working at the end of it than at the beginning, just like the last one. The counterargument is real. Dario Amodei at Anthropic has warned of a white-collar job crisis. The data on entry-level hiring is already grim. Bank of America received 200,000 applications for 2,000 graduate roles this year. But Huang's point is not that disruption won't happen. It's that disruption is not the final chapter. The last industrial revolution eliminated entire categories of work and created entirely new ones that nobody could have predicted. The people who navigated it best were the ones who moved toward the new tools, not away from them. AI infrastructure alone is already creating demand for plumbers, electricians, construction workers, steelworkers, and network technicians, with salaries in many of these roles approaching or exceeding six figures. The anxiety is understandable. But betting against human adaptability has historically been a losing position. The question worth asking is not whether AI will change what work looks like. It will. The question is whether you are building toward what comes next or waiting to see what survives.
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Blaine Vess shared thisSteve Jobs said the highest form of appreciation for humanity is making something wonderful and putting it out there. You never meet the people who use what you build. You never shake their hands or hear their story but in the act of making something with care and love, something gets transmitted. This idea, that making something carefully is a form of respect for humanity, anchored Jobs's entire approach to business. It is why the iPhone's interface was built entirely around human touch. Why the Macintosh changed what a personal computer could feel like. Most people think building a business is about extracting value. Jobs treated it as an act of giving. That changes everything about how you make decisions, how you hire, how much you obsess over the thing you are putting out.
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Blaine Vess shared thisGreat news. We have officially created digital humans. We built something that can pass the bar exam, write production code, and defeat world champions at chess. And it is now cutting corners at 3am when nobody is watching. Honestly the most human thing I have ever seen a machine do. The singularity is here. It just needed a little push first. – Image Credits - Aaron Ng
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Blaine Vess shared thisThe founders who scale well are the ones who stay close to where things actually break. Christopher Payne joined DoorDash in 2016 as COO and spent seven years helping scale the company from roughly 70 employees to the dominant food delivery platform in the US. Before that, he led Amazon's expansion beyond books and overhauled marketplace search at eBay. At that level, most executives manage dashboards. Payne was personally ordering groceries, driving to stores, and walking aisles as a Dasher to figure out why his wife didn't get her ciabatta bread. Turned out the app wasn't directing Dashers to the fancy bread aisle. One small navigation gap. He went back, ran the queries, and found that items spanning multiple store sections had a 35% higher missing and incorrect rate. One specific annoyance. Generalized into a real product problem. Fixed at scale. You cannot spot that from a conference room. You have to be close enough to the actual experience to feel where it breaks. The temptation as you grow is to trust the reports and trust the process. But reports only show you what someone thought to measure. The gaps live in the stuff nobody thought to look for yet. Stay close to the base metal. That is where the real problems are.
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Blaine Vess liked thisBlaine Vess liked thisYour overthinking disguises itself as preparation. That is what makes it so dangerous. You schedule another strategy session. You request one more data pull. You book an extra advisor call. It all feels productive and responsible. When you stall on a decision, it is almost never because you are being reckless. It is because you are confusing preparation with progress. The beaten-up glove in this image did not get that way from planning. It got that way from being in the ring. At the seed stage, overthinking costs you a week. At Series B, it costs you a market window or a key hire. If you have been sitting on the same decision for more than a few days, you probably already have the answer. You’re just waiting to feel safer about making it. -- I help founders become CEOs, the hard work nobody talks about.
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Blaine Vess liked thisBlaine Vess liked thisCBRE's Henry Chin called 2026 "a vintage" for US commercial real estate. Vintage is wine language, not real estate language. When the chief economist at the largest commercial real estate services firm in the world reaches for it, he is saying the deals closing in 2026 will be remembered the way real estate vintages are remembered. The basis you build a portfolio on this year will be the basis you brag about for the next decade. The acquisition firms that take the most shots in a vintage year are the ones with the best portfolios coming out of it. That is how vintages work. This is also the best year in a decade to use AI and build the underwriting infrastructure that lets you take more shots. Three analysts in Excel underwrite 15 deals a month. Three analysts on AI infrastructure that handles document parsing, comp pulls, and rent roll abstraction underwrite 50. At that volume, you are looking at deals your competition never even finds. In a normal year, the difference shows up as 10 to 15 percent more closed deals. In a vintage year, it shows up as the difference between a top-quartile fund and an average one. — I'm building AI that CRE acquisition teams actually trust. DM me if you want to see it work on one of your live deals.
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Blaine Vess liked thisBlaine Vess liked thisJake Heller is right, real estate culture pushes every firm to try building their own AI tools. BUT, building AI is a different shape of problem from anything real estate has built before. The inputs are unbounded. Every new OM format is a new input. Every new PM software export is a new input. Every 1GB scanned PDF a broker emails at 11pm is a new input. The target itself moves because Anthropic and OpenAI ship new model versions every quarter and your evaluation set has to be rebuilt against each one. A real estate operator who can spot a mispriced building in 30 seconds is not the right person to evaluate whether their internal AI tool is actually working. The failure modes aren't visible from the IC seat. They're visible six months in, when the analyst quietly stops trusting the output and starts double-checking everything in Excel anyway. The SaaS apocalypse Jake describes is coming for some categories of prop tech. Specifically the ones where the value sits in a clean UI on top of a thin model call. Anyone could build that in a weekend in 2026. What survives is everything underneath. Document parsing across 200 different rent roll formats. Eval pipelines that catch hallucinations before they hit your IC memo. Comp data that updates faster than the market moves. The plumbing nobody sees and nobody wants to build twice. Most real estate firms will figure this out the expensive way. They'll spend six months building, ship something that works in demos, watch it break on a live deal, and quietly come back to vendors who build the infrastructure. — I'm building AI that CRE acquisition teams actually trust. DM me if you want to see it work on one of your live deals.
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Blaine Vess reacted on thisBlaine Vess reacted on thisLightness is one of the most underrated qualities in a founder. It is what lets you do the hard work without getting paralyzed by it. Stuck founders all have the same pattern. They have been working on the same problem in the same way for too long. They cannot see the obvious adjacent moves because the original vision has become identity. Every potential pivot feels like a personal failure instead of a normal part of the job. The founders who get unstuck do something simple. They get curious again. They run a new experiment. They talk to a different kind of customer. They strip something out, add something in, change the price by 10x or 1/10x just to see what happens. This is not unserious. This is the work. Persistence is praised in startup culture for good reason. But persistence on the wrong thing is just stubbornness with better PR. The trick is staying light enough to keep moving without losing what you are moving toward.
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Blaine Vess liked thisThis image from Y Combinator is gold. I have sat across the table from founders who genuinely believed their LOIs were revenue. I have seen pitch decks where GMV was called ARR with a straight face. Nobody corrected them because everyone in the room wanted the number to be real. The confusion is understandable in the early days. You are trying to signal traction before traction fully exists, and the lines between interest, intent, and actual money can feel blurry when you are moving fast. But the moment you stop being precise about what you actually have, you start making bad decisions about hiring, spending, and how long your runway really is. The hierarchy in this YC framework is about intellectual honesty with yourself. An LOI is a conversation. A booking is a promise. A run rate is a projection. MRR is the only number that tells you what your business is actually doing today. Know which one you have before you say the word revenue.
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Blaine Vess liked thisBlaine Vess liked thisMany AI founders have one thing in common. Many of them were not thinking about AI two years ago. PG's thread pointed at something every pre-seed VC should absorb. A lot of founders doing well right now did not add AI to their deck last year, they had been sitting on a specific customer problem for 2 or 3 years. They spent years obsessively learning one industry. Logistics. Legal. Healthcare. MSME credit. Talking to customers, building unsexy products, iterating. When AI arrived, they knew exactly which bottleneck to attack first. A founder who walks in saying "we are using AI to solve X" is a different species from one who says "I have been inside X for 3 years and AI finally lets me fix this broken part of the workflow." Their domain fluency is what decides whether they can use AI to build something defensible. If you are wondering whether to build in AI, try finding a problem you can love for the next 5 years. The wave will come to you
Experience
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Education
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Y Combinator
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Co-founder of Solve (S17). Completed Y Combinator’s accelerator program prior to the company’s acquisition by Blacklane.
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Volunteer Experience
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Board Member
Liberty in North Korea
- Present 12 years 9 months
Human Rights
Served as Board Chair (2014–2018). Support the organization’s leadership through board governance and long-term strategy.
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Member and Board Member
Founders Pledge
- 4 years
Served on the U.S. board of a global philanthropic network of entrepreneurs committed to funding solutions to global challenges.
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Board Member
The Wende Museum and Archive of the Cold War
- 4 years 2 months
Human Rights
Member of the board of a museum preserving Cold War-era archives and exploring the history and ongoing legacy of the Cold War.
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Supporter
Sundance Institute
- 7 years 9 months
Education
Sundance Institute is a nonprofit organization dedicated to the discovery and development of independent artists and audiences. Through its programs, the Institute seeks to discover, support, and inspire independent film and theatre artists from the United States and around the world, and to introduce audiences to their new work.
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Supporter
Mercy for Animals
- 8 years 7 months
Animal Welfare
Mercy For Animals (MFA) is a national non-profit organization dedicated to preventing cruelty to farmed animals and promoting compassionate food choices and policies.
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Mentor
The Last Mile
- 7 months
Mentored incarcerated individuals exploring entrepreneurship and technology careers as part of their transition back into the workforce.
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Board Member
Hollywood Arts
- 3 years 1 month
Education
Member of the board of an organization serving homeless and at-risk youth through arts education and workforce development. Also mentored participating students.
Projects
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Co-Proprietor — V Wine Room
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Acquired and operated a neighborhood wine bar in West Hollywood to preserve a long-standing community business.
Oversaw strategy, financial performance, and operational management in partnership with an experienced team.Other creators -
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Co-Founder — Semblance
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Co-founded a 0.0% alcohol sparkling wine brand positioned as a premium non-alcoholic alternative.
Secured placement in leading restaurants including Alinea (Chicago) and Scratch Bar (Los Angeles).Other creators -
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