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There’s a YC company building these mini drones to kill mosquitoes. It sounds ridiculous… until you remember: - Ring started as “a doorbell with a camera” - Roomba started as “a vacuum robot” - Whoop is a bracelet that tells you when to sleep - Peloton is a bike with an iPad Do you think this is a billion dollar business or something that will be on the clearance aisle at CVS?

I have a friend with the most lucrative side hustle I have ever seen. He makes over $500k a year introducing companies to private equity funds. And he does it completely anonymous on Reddit. Just a random username with absurd karma. He writes posts breaking down valuation, capital structure, and diligence in a way founders actually understand. His best ones go through pricing power, customer concentration, repeatable systems, cash conversion, and what unit economics look like when growth slows. Founders DM him because his posts make them feel like someone finally understands their business. He never tells them he knows investors, he just listens. And when the business is real and the numbers make sense, he moves the conversation to WhatsApp and quietly asks if they want an intro. Then he sends the deck to 7 PE funds that he's worked with for years (all of them know who he actually is). Most intros go nowhere. But 1-2x a year an intro turns into a management meeting, then a term sheet, then a closed deal. And when it does, he gets a percentage. Last year he made more behind his anonymous Reddit username than he did at his full time job. I asked him how he built a deal flow machine without a name, a brand, or visibility. He said something I will never forget: “Founders do not care who you are. They care if you understand them. Investors do not care about your title. They care if you only send them real opportunities. Nail those two things and you do not need to be visible.” He's the be the best PE scout nobody has ever heard of.

I had lunch with a well-known growth-stage investor who told me “the most important metric we track isn’t CAC, LTV, or retention, it’s time-to-$2M of ARR.” He’s been generating massive returns for decades and shared what has excited him over the last 15 years: 2010: $2M of ARR in 3-5 years 2020: $2M of ARR in 2 years 2024: $2M of ARR in 1 year 2025: $2M of ARR in 10 days He believes AI and viral content will continue accelerating this timeline and over the next few years he’ll be looking for: 2026: $2M of ARR 24 hours 2028: Exit stealth with a 5 minute launch video and sell $2M of ARR before the video ends 2030: Sell $2M of ARR before you even tell customers what your idea is 2040: (-1) year to $2M of ARR (he expects advancements in quantum physics to enable startups to launch in the past) Exciting times ahead!

Investing in seed *ideas* is largely BS. We raised our seed as an adtech company and sold the business 10 years later as a vertical SaaS company for flooring retailers. Coming out of Google to build an adtech startup was sexy and exciting to VCs. The irony is that the quiet, unsexy market nobody paid attention to ended up producing the real outcome. Investing in *people* at seed though is never BS.

Worst "Oh Shit" moment in my company's history: We spent $75,000 for a new custom logo. One day before the re-brand... Leonardo DiCaprio launched a climate tech VC fund and trademarked the exact same logo. Not joking. Still no idea how this happened.

Apple Intelligence is so bad that it isn't impacted by the AI sell off.

The best pairing is two people with enough patience and energy to battle startup life together for a decade without giving up. It doesn’t matter if you’re technical or not. We built a $200M business with business + business. People > technical ability

The 4 pillars of building & selling a vertical SaaS company: 🐴 Trojan horse software to get your foot in the door 🪴Add on software to increase NRR & logo retention 📈 Increase TAM through fintech/marketplace to take % of GDP 🤝 Sell to growth equity at $10M ARR & rule of 40

Constellation Software 2.0 is a unicorn waiting to be built. Thousands of startups raised $3-$5M million seed rounds at 10-20x revenue multiples during ZIRP and now they’re trapped. - Growth VCs won’t invest - Founders can’t take on more capital without significant dilution - Too small for PE - Executive team running out of steam without capital and running lean on resources The numbers tell the story: - Over 50% of post-2020 SaaS startups are now “zombies” (stalled growth, no clear exit) - AI competitors are putting margin and churn pressure on legacy vertical businesses - Venture funding (outside of AI) is at a 5 year low and founders are exhausted But here’s what many overlook. These are GOOD businesses. They just have bad cap tables, and probably burnt out founders. But this is where Constellation 2.0 comes in. The playbook is simple. Growth equity + AI - Acquire company and recap the cap table - Optimize pricing and upsells - Focus engineering team on internal AI to gain efficiency and reduce payroll costs - Reinvigorate the team with a new culture and vision - Drive cash flow and profitability If you’re building Constellation 2.0 or have a startup with an upside down cap table, reach out! Would love to chat.

After this post I talked to 4 founders in even more obscurely massive industries. - ERP for drapery businesses - AI for land surveyors - CRM for HOA management companies - Website + fintech for RV parks We live in a time where opportunities are truly endless.

There’s a YC company building these mini drones to kill mosquitoes. It sounds ridiculous… until you remember: - Ring started as “a doorbell with a camera” - Roomba started as “a vacuum robot” - Whoop is a bracelet that tells you when to sleep - Peloton is a bike with an iPad Do you think this is a billion dollar business or something that will be on the clearance aisle at CVS?

I had lunch with a well-known growth-stage investor who told me “the most important metric we track isn’t CAC, LTV, or retention, it’s time-to-$2M of ARR.” He’s been generating massive returns for decades and shared what has excited him over the last 15 years: 2010: $2M of ARR in 3-5 years 2020: $2M of ARR in 2 years 2024: $2M of ARR in 1 year 2025: $2M of ARR in 10 days He believes AI and viral content will continue accelerating this timeline and over the next few years he’ll be looking for: 2026: $2M of ARR 24 hours 2028: Exit stealth with a 5 minute launch video and sell $2M of ARR before the video ends 2030: Sell $2M of ARR before you even tell customers what your idea is 2040: (-1) year to $2M of ARR (he expects advancements in quantum physics to enable startups to launch in the past) Exciting times ahead!

Worst "Oh Shit" moment in my company's history: We spent $75,000 for a new custom logo. One day before the re-brand... Leonardo DiCaprio launched a climate tech VC fund and trademarked the exact same logo. Not joking. Still no idea how this happened.

I have a friend with the most lucrative side hustle I have ever seen. He makes over $500k a year introducing companies to private equity funds. And he does it completely anonymous on Reddit. Just a random username with absurd karma. He writes posts breaking down valuation, capital structure, and diligence in a way founders actually understand. His best ones go through pricing power, customer concentration, repeatable systems, cash conversion, and what unit economics look like when growth slows. Founders DM him because his posts make them feel like someone finally understands their business. He never tells them he knows investors, he just listens. And when the business is real and the numbers make sense, he moves the conversation to WhatsApp and quietly asks if they want an intro. Then he sends the deck to 7 PE funds that he's worked with for years (all of them know who he actually is). Most intros go nowhere. But 1-2x a year an intro turns into a management meeting, then a term sheet, then a closed deal. And when it does, he gets a percentage. Last year he made more behind his anonymous Reddit username than he did at his full time job. I asked him how he built a deal flow machine without a name, a brand, or visibility. He said something I will never forget: “Founders do not care who you are. They care if you understand them. Investors do not care about your title. They care if you only send them real opportunities. Nail those two things and you do not need to be visible.” He's the be the best PE scout nobody has ever heard of.

Constellation Software 2.0 is a unicorn waiting to be built. Thousands of startups raised $3-$5M million seed rounds at 10-20x revenue multiples during ZIRP and now they’re trapped. - Growth VCs won’t invest - Founders can’t take on more capital without significant dilution - Too small for PE - Executive team running out of steam without capital and running lean on resources The numbers tell the story: - Over 50% of post-2020 SaaS startups are now “zombies” (stalled growth, no clear exit) - AI competitors are putting margin and churn pressure on legacy vertical businesses - Venture funding (outside of AI) is at a 5 year low and founders are exhausted But here’s what many overlook. These are GOOD businesses. They just have bad cap tables, and probably burnt out founders. But this is where Constellation 2.0 comes in. The playbook is simple. Growth equity + AI - Acquire company and recap the cap table - Optimize pricing and upsells - Focus engineering team on internal AI to gain efficiency and reduce payroll costs - Reinvigorate the team with a new culture and vision - Drive cash flow and profitability If you’re building Constellation 2.0 or have a startup with an upside down cap table, reach out! Would love to chat.

Investing in seed *ideas* is largely BS. We raised our seed as an adtech company and sold the business 10 years later as a vertical SaaS company for flooring retailers. Coming out of Google to build an adtech startup was sexy and exciting to VCs. The irony is that the quiet, unsexy market nobody paid attention to ended up producing the real outcome. Investing in *people* at seed though is never BS.

There's a massive opportunity to launch a buyout fund (think constellation software) focused on buying vertical SaaS companies. I am talking about companies with <$3M ARR Growth equity normally wouldn't touch this, but here's why I believe it's a unique opportunity in time: 👉 ZIRP changed everything - 0% interest rates flooded the market with cheap money and inflated valuations. During ZIRP most companies were raising at a $10M+ valuation with $0 in revenue. The problem is that most companies couldn't grow into valuations quickly enough, creating upside-down cap tables. A lot of these companies have real potential and interesting businesses, but their growth is slow/stalled because we went from spend to generate revenue to cut for profitability and they are stuck in no man’s land without capital. These companies will either turn into zombie companies or look for soft landings when the founder eventually gets exhausted. 👉 AI made it easier to compete - New competitors building with AI are coming out of nowhere and competing with legacy vertical software applications. This has created downward pricing pressure and increased churn for a lot of these startups. Further accelerating ZIRP companies into zombie/soft landing status, 👉 Capital constraints - Just like companies raised rounds that were too big at too high of valuations, so did venture and equity funds. They are still tightening their belt and would rather put money into a new AI startup rather than an upside-down cap table vertical SaaS business. Also, with the lack of venture liquidity/exits over the last 4 years, it’s becoming increasingly difficult for current funds to raise next funds. This opens the door for new funds with new exit time horizons to come in with much better economics and IRR. With the right playbook, this has created a MASSIVE opportunity. If you believe in valuation arbitrage and M&A synergies, the time is now.

Route 22 in NJ. Stay safe out there. 🙏❤️

When we raised in 2013 the biggest concern from investors was that we didn’t have a technical co-founder. Now a decade later every investor I talk to is looking for the GTM co-founder. The technical co-founder used to be the edge. Today, it’s the one who knows how to build distribution.

Apple Intelligence is so bad that it isn't impacted by the AI sell off.

A friend runs a vertical SaaS company doing $40 ARR. We were riffing last night about what comes next. They’ve already built the system of record for their industry (1,000+ SMB customers with 93% GRR). They own the workflow. But they don't own the money flow.... YET Here's a plan we came up with to help him get to an incremental $100M in ARR. 👉 1/ Payments Today, a meaningful portion of customer transactions still run through outside processors or manual methods. If payments were default-on and tightly embedded (instant settlement, transparent rates, volume-based incentives) attach rates could 2x and take-rates could rise 30–50 bps (they are currently only getting 40 bps.. That single operational shift could add $25–40M in incremental annual revenue. 👉 2/ Embedded Finance This company sees its customers’ entire operation including sales, invoices, fulfillment, collections. With that operating data they could layer in: - Working-capital advances for customers with predictable cash flow. - Transaction-based lending tied to verified pipeline. - Consumer or end-client financing embedded at the point of sale. If they financed even 3–5 % of the transaction volume moving through their platform, that’s $15–30M in new, high-margin revenue with best-in-class risk controls. 👉 3/ Marketplace of Aggregate Demand Right now, every customer on the platform spends heavily to acquire their own demand. The platform already knows who has capacity, who performs well, and who’s looking for more work. A curated, verified marketplace that routes business between platform users could easily drive 2–3 % of total network volume, and taking even a 5–10 % transaction fee could yield another $10–20M in revenue. And of course... every transaction in that marketplace flows through the platform’s payments rails. 👉 4/ M&A There are ~20 of smaller vertical SaaS players adjacent to their category each doing $1–5M ARR. Acquire selectively and eun payments, financing, and marketplace layers across the new base. Every acquisition adds not just ARR, but multiple new revenue streams. That’s another $15–30M in accretive upside over a few deals. Here's how the math breaks down: - Payments+$25–40M - Embedded Finance+$15–30M - Marketplace+$10–20M - M&A + Cross-Sell+$15–30M Obviously, this is easier said than done... but the path is there.

The 4 pillars of building & selling a vertical SaaS company: 🐴 Trojan horse software to get your foot in the door 🪴Add on software to increase NRR & logo retention 📈 Increase TAM through fintech/marketplace to take % of GDP 🤝 Sell to growth equity at $10M ARR & rule of 40