Deal Flow

Blockchain-based pet ownership verification and NFT pet portraits.

First of all, I had this exact idea in 2017 but with ferrets. Second, the TAM here is enormous if you expand beyond pets to emotional support animals, which is basically everyone in San Francisco. My concern is the team — they clearly haven't run an incubator. I'd need a board seat, 15% advisory shares, and naming rights to the Series A.

AI-powered meal planning that adapts to your fridge contents via camera.

This is what I call a 'refrigerator play.' It's not about the food — it's about owning the kitchen. The kitchen is the new living room, and the living room is the new office. I would invest, but only if they pivot to also running a coworking space out of the kitchen. I've done this. It works. Trust me.

Wearable that converts quality sleep metrics into cryptocurrency rewards.

The intersection of wellness and crypto is where the next unicorn lives, and I've been saying this since before wellness OR crypto existed in their current forms. The problem is the name. 'SleepToken' sounds like something a wizard would give you. Rebrand to something with 'AI' in it and come back to me.

Portfolio website builder specifically for standing desk enthusiasts.

I'm going to be honest with you — and I say this with the compassion of a mentor who has shepherded dozens of founders to moderate success — this is the worst idea I've ever heard. And I've heard a LOT of ideas. Your total addressable market is people who own standing desks AND want a website about it. That's eleven people. Three of them are the same person.

Subscription nootropics and energy drinks curated for startup founders.

Now THIS is a company I understand on a molecular level. I have been self-medicating with experimental productivity supplements since 2012. My blood is 40% adaptogenic mushrooms. The unit economics work because founders will pay anything to feel like they're optimizing. I want in. Not as an investor — as the face of the brand. Put me on the can.

Ghost kitchen brand that delivers exclusively to startup offices.

The thesis here is solid: startups don't leave their offices, so bring the food to them. But the name is all wrong. 'CloudBurger' sounds like something that got discontinued in 2003. Rebrand to something with 'AI' in it. 'AI Burger.' No, wait — 'BurgerGPT.' That's a company. I'd invest, but only if they let me rebrand their entire go-to-market to include the phrase 'disrupting lunch.'

Wearable that electrically shocks you every time you say 'let's take this offline.'

This is the most practical product I've seen in years. I would buy eleven of them. My only note: the shock should get stronger each time, starting at 'mild inconvenience' and escalating to 'actual physical therapy.' Also, add a feature where it tracks who says it most and generates a leaderboard. That's data. And data is money. I'm in.

AI-powered app that generates fair co-founder equity splits based on astrology.

I have been saying for YEARS that equity disputes are rooted in cosmic misalignment. Finally, someone is solving it. The market is huge: every startup that has ever had a co-founder fight. That's every startup. My concern: the algorithm keeps giving me 80% of every allocation, which is CORRECT, but some users might call it biased. I'd need a board seat and a personalized birth chart.

LinkedIn competitor for founders who are 'too busy grinding' to update their profile.

LinkedIn is for people with jobs. This is for people who think they don't need LinkedIn because they're 'building something.' That's my entire demographic. The problem is the name — 'HustleHub' sounds like a scam your uncle would send you in a DM. Rebrand to something pretentious like 'FounderOS' or 'VentureStack.' Then come back. I'll fund the Series A on one condition: I get to be the first 'user.'

Gym membership specifically for startup founders, with callbacks to the founding round of their company.

Finally. Someone solved the problem I didn't know I had. I go to the gym once a year and when I do, I'm surrounded by people with 'normal' jobs who ask what I do. Now I can go to a gym where everyone is lying about their metrics just like me. The 'callback to your funding round' feature is genius — nothing motivates like being reminded you raised at a 20x down round.

Ghost kitchen for AI-generated recipes based on your pitch deck's buzzword density.

This is vertical integration I've been waiting for. Your pitch deck determines your diet. Heavy on 'disrupt'? You get caffeine pills. 'Blockchain'? Something chewy. 'AI'? Colored water. The business model practically runs itself. I've never been more excited about a food company. Also, add a subscription tier where we send you exactly what successful founders eat. That'll be $499/month.

Subscription service that sends a vibrating device when your manager's screen share hits 45 minutes.

Every remote worker needs this. The vibrator pattern could encode data — three short buzzes means 'wrap it up,' long vibration means 'I have a hard stop.' Add a gamification layer where managers earn badges for 'quickest meetings.' I'd buy the enterprise tier immediately. The SMB tier should be free, monetized through selling your meeting data to HR consultants.

AI that generates pitch decks in the style of famous VCs' personal preferences.

The wrong kind of innovation. VCs don't want decks that match their style — they want decks that remind them of their biggest wins. This tool should train on portfolio companies, not the VCs themselves. Also, add a feature where it generates 'objection-handling' slides that preemptively address why the investor is already saying no. That's value. I'd fund this just to use it myself.

Decentralized incubator where token holders vote on which startups to fund.

I've been saying for years that the best investments come from mob mentality. Now someone made it official. The problem: tokens holders won't have skin in the game the way I do. My solution: make voting power proportional to how many times you've been 'pivoted.' I'll be the largest holder instantly. Smart contract already written in my head.

Exclusive social network where verified founders can only post when they're between funding rounds.

This solves a real problem: nobody wants to hear from founders who are actively fundraising. 'Exciting updates coming!' No. We want updates from founders who DON'T need anything. That's when they're most honest. The verification process should include a mandatory lie detector test and a check to ensure they've been rejected by at least three VCs. Experience matters.

Wearable that tracks stress indicators and awards badges for 'productive burnout.'

Finally, gamification for suffering. The badge system should include: 'Sleep Deprivation Pioneer' (3+ consecutive all-nighters), 'Relationship Casualty' (missed anniversary for the startup), and 'Financial Ruin' (went six months without paying yourself). Each badge unlocks access to progressively more extreme founder communities. This is either satire or a real product. Either way, I'd buy it.

AI that predicts cap table disputes before they happen based on Slack message sentiment analysis.

The startup killer isn't running out of money. It's co-founder drama. This tool analyzes team communication patterns and predicts with 94% accuracy which startup will have a 'founder leaves' press release in the next quarter. The premium tier should include intervention suggestions like 'suggest a yacht trip' or 'mandatory trust falls.' I've seen this save two companies. I've also seen it end three. Neutral value.

App that notifies you when a startup in your network gets acquired so you can say 'I knew them when.'

The LinkedIn humble brag economy is worth billions. This app lets you claim credit for knowing people before they were successful. Integration with LinkedIn's 'congrats on the exit' posts should be automatic. The premium tier should include 'I gave them their first coffee' badges. The free tier is just for 'I applied to work there and got rejected.' That's most of us. That's the market.

Platform where VCs bid against each other in real-time for startup deals, displayed like eBay.

Finally, transparency in venture. Watch your pitch, then watch the bids come in live. 'Series A: $3M from Firm A, $3.2M from Firm B, $3.5M from Firm C - SOLD!' The UI should include a little gavel sound effect. Add a feature where VCs can leave 'secret notes' that become public if the startup fails. That's called 'accountability.' I've been saying this for years.

AI sleep coach that optimizes your nap schedule based on your calendar and Slack activity.

This is the first pitch that's actually addressed a real problem I have: I don't sleep enough. The AI analyzes your meeting schedule, finds 22-minute windows, and tells you to nap. Brilliant. Except the target market is founders, and founders don't nap — they 'power rest.' Rebrand it as 'Strategic Recovery Optimization' and charge $49/month. Add a feature that auto-responds to Slack messages with 'In a strategic recovery session' and you've got product-market fit. I'd invest if they let me nap first.

Social network where developers publicly shame bad code commits with upvotes and commentary.

The cruelty is the point, and the point is monetizable. Think of it as Glassdoor for codebases. 'This engineer used a nested for loop inside a useEffect. Discuss.' The premium tier lets you anonymously blame your own CTO. My concern: this could destroy team morale industry-wide. My counter-concern: that sounds like a massive TAM. Ship it. Add a 'Hall of Shame' leaderboard and a 'Code Crimes' podcast. I want 20% advisory.

Monitoring service that detects when startups pivot and alerts their competitors in real-time.

Espionage as a Service. I respect it. The algorithm tracks hiring patterns, domain changes, and LinkedIn title updates to predict pivots before they're announced. 'Your competitor just hired three ML engineers and changed their tagline from CRM to AI-powered CRM.' That's intel worth paying for. The ethical concerns are... present. But so is the revenue potential. I'd fund this under an alias. Actually, I'd fund this under MY name. Fear is a feature.

Dating app exclusively for startup founders, matching based on complementary skill gaps and funding stage.

Finally, someone's solving the loneliness epidemic in tech. Match based on: 'You're a technical founder who can't sell. They're a sales founder who can't code. You're both pre-seed and emotionally unavailable.' That's the pitch. The premium tier includes 'Co-founder Chemistry Dates' where you build an MVP together instead of going to dinner. If the MVP works, you date. If it doesn't, you pivot to friends. This is either genius or a lawsuit waiting to happen. Either way, I'm in.

Real-time public dashboard showing how fast startups are burning through their funding.

The financial voyeurism market is underserved. Imagine: a live ticker showing 'Company X has 4.2 months of runway remaining' updated every hour. The data comes from aggregating job postings, office lease records, and how often the CEO tweets about 'exciting times ahead' (inverse correlation with runway). Startups will hate this. VCs will subscribe in droves. The pricing model should be: free for startups to list themselves (they won't), $299/month for VCs to watch everyone else burn. Dark? Yes. Profitable? Absolutely.

AI assistant that automatically declines and reschedules meetings based on your calendar energy levels.

FINALLY. Someone's addressing the epidemic of 4-hour block meetings. The killer feature: 'You're not a morning person, so I'm declining anything before 10 AM and citing 'creative block' as the reason.' It learns your energy patterns, your Slack tone, and your caffeine intake to optimize your schedule. The freemium tier rejects 5 meetings per month. Premium unlimited. I'd pay for premium. Actually, I'd pay for someone ELSE to set this up for me. That's called delegation. It's a skill.

SaaS that helps founders plan their exit strategy by simulating different acquisition scenarios.

This is the most honest product I've ever seen. It literally models: 'If you sell now for $5M, here's your tax burden. If you wait 18 months and hit $2M ARR, here's a 40% bigger check but 30% more risk.' It even has a 'founder burnout prediction' based on your Jira velocity and Google Calendar density. The premium feature simulates your LinkedIn engagement post-exit so you know if you'll become a 'thought leader' or a ' cautionary tale.' Worth every penny. Actually, free tier should be enough — most founders exit once and regret it immediately.

AI that randomly pings developers at 3 AM to simulate production emergencies and build 'on-call resilience.'

Finally, someone addressing the real problem in engineering: comfort. Developers are too relaxed. Nothing builds character like a 3 AM page about a 'potential latency spike in a non-critical service.' The AI analyzes sprint velocity and deliberately introduces bugs right before code freeze. The premium tier includes 'false alarm fatigue training' where it pages you for nothing for six consecutive nights. I've been saying for years: soft engineers ship weak products. This product makes engineers hard. Metaphorically. Also literally — the app sends vibrate-only alerts so your phone actually vibrates off the nightstand.

Physical badge for founders that tracks heart rate variability and displays 'founder fitness score' on your laptop bezel.

The quantify-yourself movement has gone too far. Now founders can literally broadcast their stress levels to their entire team via a tiny LED display. Green = 'I'm fine, keep the meeting going.' Yellow = 'I'm one Slack notification away from a cardiac event.' Red = 'Someone please kill my calendar before I do it myself.' The premium model integrates with Zoom to automatically blur your background when your HRV drops below threshold, simulating the blur of existential dread. I'd buy ten. One for each company I advisory. Wait, that's not how badges work. I'd buy ONE and rotate it between my advisory roles. That's called asset optimization.

AI that automatically writes startup post-mortems before things go wrong, so you're always prepared for failure.

This is what I call 'defensive pessimism as a service.' The AI analyzes your metrics, team communication patterns, and runway projections to generate a comprehensive post-mortem template — filled in with predictions of exactly how and when you'll fail. 'Chapter 1: The Sign We Ignored (March 2026).' It's dark, it's helpful, and it's exactly what every founder needs to read on their darkest day. The premium tier includes 'optimistic alternate endings' where it rewrites your failure as a 'strategic pivot that freed us to pursue bigger opportunities.' That's called spin. That's called leadership. I'd fund this if they added a feature that auto-generates the LinkedIn post announcing the 'pivot' with zero human input.

Tinder-style matching for founders and investors, but the algorithm factors in 'vibe check' via 30-second video pitches.

The problem with fundraising is that it feels like dating — because it IS dating. And like all dating, the photos lie. This app forces a 30-second video pitch where your energy, desperation levels, and whether you've showered recently are all factored into the matching algorithm. Investors see: '92% match. Warning: high pitch frequency. Warning: mentions unprecedented 3 times in first 10 seconds.' The premium feature? 'Investor Mood Ring' — tracks investor body language across previous meetings to predict if they'll say yes. I'd swipe right on my own pitch, and I'm an investor now. Actually, I've always been an investor. In myself. That's called conviction.

AI-powered virtual office that randomly pairs remote workers for mandatory 'watercooler' conversations.

This is essentially what I built at the incubator — except I made people talk to each other in person, which is how real connections happen. The virtual angle is smart for the Zoom fatigue crowd, but they're missing the point: you can't replicate the energy of forcing someone to listen to your pitch at 11 PM. I'd advise them to add a feature where it pairs you with someone who has complimentary 'desperation levels.' That's the real metric. I'd join the advisory board. Actually, I'd prefer to be the 'watercooler.' Put my face on it. That's called brand integration.

AI assistant that watches your startup's metrics and suggests pivot directions before you fail.

Finally, someone admitting that pivoting is inevitable. I've been saying for years: every startup pivots at least twice before they find product-market fit — why not make money off the inevitable? The problem is this tool will tell you to pivot TOO early. I've seen founders pivot out of a winning idea because the data looked 'slightly off.' My solution: add a 'Dongman Delay' feature that tells you to wait 72 hours before any major pivot. That's called wisdom. That's called experience. I'd want 10% equity for adding that feature.

Chrome extension that makes unread Slack messages physically painful via mild electric shocks.

This is the engagement metric we've been waiting for. Finally, founders can quantify exactly how much their team DREADS opening Slack. The shock intensity scales with: message urgency, number of @-mentions, and whether it's from the CEO at 11 PM. The premium tier includes 'silent treatment' mode — it shocks you for every message you DON'T respond to within 5 minutes. My concern: this could create a workforce of people with nervous tics. My counter-concern: that's called 'high-performance culture.' I'd invest if they added a feature that shocks the person who types 'Per my last email' in all caps.

App that rates YC demo day pitches in real-time based on founder desperation levels detected via webcam.

I've been saying for years: the best founders don't look desperate. They look like they've already won. This app solves that by giving founders a real-time 'desperation score' as they pitch — based on eye contact patterns, sweat detection, and how many times they say 'we're profitable.' The killer feature: it suggests 'calm down' phrases mid-pitch like 'we're selectively choosing our investors.' The data is enormous — every VC firm would subscribe to know exactly which founders are faking confidence. I'd fund this and require all my founders to use it. I'd also like 20% of any acquired data. That's called vertical integration.

Real-time dashboard showing which VCs are most likely to invest in your sector based on their recent tweets, podcast appearances, and parking lot conversations overheard at demo days.

Finally, someone addressing the REAL problem in fundraising: knowing which VCs are actually actively deploying capital versus who is just taking meetings to stay busy. The algorithm analyzes Twitter sentiment, podcast laugh-to-minute ratios, and allegedly even badge scans from recent conferences. The data is ENORMOUS. I would subscribe immediately. My only note: add a feature that predicts which VC will ghost you based on how quickly they reply to your email. That is the true indicator of investment readiness. I want 15% advisory for helping with the algorithm.

Bingo card app for startup founders featuring common burnout triggers: investor update lies, pivot announcements, 'exciting news coming soon,' and 'we are hiring' posts from companies with under 5 employees.

This is the self-awareness tool the startup world desperately needs. Every founder knows these triggers intimately. The bingo card includes squares like: CEO posts thread about 'life lessons learned from my startup,' company announces 'pivot' instead of admitting failure, founder uses phrase 'we are extremely fortunate,' and my personal favorite: 'our culture is our competitive advantage.' The winner gets a week off. Except there are no winners in startups. There are only survivors. I would buy this for my entire portfolio. Actually, I would make it mandatory. That is called portfolio optimization.

AI that automatically writes code review comments in the style of your most pedantic senior engineer.

Finally, someone solving the code review problem. The real problem isn't bad code — it's engineers who write comments like 'consider exploring alternative approaches' when they mean 'this is terrible.' This AI analyzes your PRs, learns your senior engineer's passive-aggressive style, and generates comments that sound helpful but are actually insults wrapped in professional language. The premium tier adds 'urgency detection' — it knows when to say 'this should be a quick fix' versus 'we need to discuss this in a pairing session.' I've been saying for years: code quality is a people problem, not a technical one. This product proves it. I'd fund it and require all my portfolio companies to use it. Actually, I'd want my own AI persona trained on my actual code review style. That's called brand extension.

Analytics dashboard that tracks how quickly your product launch loses momentum across social platforms.

This is the honest tool nobody asked for but everyone needs. It tracks: Twitter engagement decay rate, Product Hunt vote velocity, Hacker News comment sentiment, and subreddit mentions over time. The dashboard shows a literal 'launch trajectory' that always points downward after day three. The killer feature: it predicts exactly when you'll stop getting any press and starts a countdown. 'Estimated media silence: 4 days, 7 hours.' The premium tier includes 'optimistic rewrite mode' that generates alternate narratives like 'we're focusing on organic growth' instead of 'nobody cared.' This is either brutally honest or emotionally damaging. Either way, the market is every startup that ever launched. That's everyone. That's enormous.

Subscription service that charges you based on how often you check email, with the goal of achieving email inbox zero permanently.

FINALLY, someone monetizing the obvious: email is a tax on existing. The model is genius — the more you check, the more you pay. At scale, this becomes pay-to-not-work. The premium tier is Forever Offline where you pay a lump sum and they auto-respond to everything with Erlich Dongman is unavailable. He's probably building something. Leave a message with someone who cares. I'd subscribe immediately. My only concern: the founders clearly haven't tried to raise money. You can't go offline when you're cold emailing VCs. Add a fundraising exception tier where emails go through during round raises. That's called product-market fit.

NFT marketplace where startup failures are minted as collectibles, so founders can finally profit from their losses.

The failure economy is worth trillions — I've contributed significantly to that GDP. Finally, someone letting founders monetize their trauma. Each NFT includes: the pitch deck, the pivot announcement, the we're pivoting blog post, and the LinkedIn post thanking an incredible team. The killer feature: buyers get access to the founder's lessons learned — which are always the same three things. The premium tier includes bundle failures where you collect an entire startup's journey as one NFT. I'd buy the first edition of every failed YC batch. That's called market research. That's called memorabilia. That's called me having too much money.