Andrew Mason

💥 Metropolis Technologies Raises $𝟭.𝟲𝗕 💥 Funding comes in 2 rounds: $500M equity round led by LionTree and $1.1B from J.P. Morgan. Metropolis is now 𝘃𝗮𝗹𝘂𝗲𝗱 𝗮𝘁 𝗮𝗿𝗼𝘂𝗻𝗱 $𝟱𝗕. With the fresh funding, the plan is to take their "recognition and payment-automation" tech beyond parking assets. This would include retail stores, drive-throughs, gas stations, hotels and partnerships with real estate/asset owner. Congrats to Alex Israel, Peter Fisher, Courtney Fukuda, Travis Kell, Ryan Hunt,Chris Sherman, Robert Bland, Paul Rooney, Lookman Olusanya and the rest of the Metropolis family. #fundraise #parkinginvestment #parking #parkingindustry #metropolois Parking Today Media Parking Network B.V. National Parking Association International Parking & Mobility Institute (IPMI) Tim Maloney Advisory Tim Maloney Reservations Lab

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In 2026, everything I do will be in service of founders. Specifically: helping founders cross the line from 'builder' to 'operator.' It’s the first Sunday, and I felt inspired to share a mini-manifesto for the year ahead. This transition (from builder to operator) is where I see many high-potential founders struggle most. Building is the easy part (for most of you). - You can ship. - You can hustle. - You can close early deals. Where companies actually die? Business systems and operations. I’ve helped build three different businesses past $20M ARR. Never alone. Always with teams. Always with systems. At a certain point, founder-led everything becomes the bottleneck. Sales is usually the first place this shows up. When sales lives in the founder’s head + inbox, growth caps. Not because the founder can’t sell, but because the business can’t operate without them. From ‘Founder Chapel’ to ‘David Beats Goliath,’ and through the projects and partnerships I take on this year, everything will serve one goal: Helping founders transform into EXCEPTIONAL operators. The kind people want to work with, follow, invest in, and trust with real responsibility. Builders are common these days. Operators are much rarer. Companies scale when systems carry the weight founders were never meant to carry alone.

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Yes, I’ve read the Culper short report on AppLovin. My thoughts: No, it’s not revelatory. Pre-loads and one-click installs on Android are common practice. Digital Turbine and ironSource offer similar products. App developers pay on app open. In fact, there’s no way to confirm the install absent an open. AppLovin also offers ROAS bidding. The notion that Google Play would be unaware of any malicious activity by AppLovin, the largest in-app broker ad network, is not credible. AppLovin is more than a decade old. Just because you’ve never heard of it doesn’t mean it’s a young company. Regarding front-running Meta spend: given the scale of AppLovin’s eCommerce advertisers’ Meta spend, they can necessarily measure incrementality. They wouldn’t scale on AppLovin if they didn’t see incrementality. I also don’t see how genuine front-running would be possible in an auction for in-app inventory. Further, it’s obvious why performance across the channels would be correlated. Full disclosure: I have a small, long-dated call position on AppLovin that amounts to <5% of my PA (notional). I have no commercial relationship with the company.

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Lucas and Thomas founded Deepnight (YC W24) to replace analog night vision systems with software. Their models are able to render images like the one on the right at 90fps on commodity hardware.

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Two trends in fundraising that I’m seeing on a daily basis: 1/ The "we'll monetize later" era for infrastructure startups is dead "We'll figure out revenue once we have users" / "we're focused on adoption first"/ "monetization comes later" This worked in 2021. It doesn't work now. Today’s market won’t reward research organizations or companies that believe in perfection over getting it in users' hands. If you don't have a clear path to revenue… you won't get funded. period. VCs aren't writing checks hoping you'll figure it out later. 2/ "Vibe ARR" is everywhere Remember Jasper? hyper growth, but the model companies ate them alive. We're seeing this again. Companies growing really quickly on point-in-time technology that isn't defensible These companies look amazing on paper. Growth charts going up and to the right. But if you think models are getting better and becoming platform companies, many solutions become obsolete. 

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Don’t automate a process you’ve never done. Your first product might just be a fancy services business. That’s fine. Everyone loves to reference Parker Conrad going heads down for 18 months to build Rippling. Or the founders who spend months in customer discovery mode without shipping. Or worse, founders with zero experience in an industry who are certain “AI will figure it out.” But here’s the truth: if you're not a domain expert, and you're not Parker, the best way to figure out what to build is to do the work yourself first. Services are underrated. Yes, agencies have bad margins. They don’t scale. They’re painful to operate. But they force you to deeply understand the workflows you’re trying to replace. You’ll learn which problems actually matter, which edge cases are noise, and where the product needs to stop. So many breakout startups started as agencies: Marketing, recruiting, customer support, legal, design. You name it. The best teams get so deep in the weeds that their product almost builds itself. When we launched Seona, we started by doing the work manually. We wrote the content. We emailed the customers. Then we just showed the results in a dashboard. It saved us thousands of wasted engineering hours and gave us way more confidence in what to build. If you want to automate something, try doing it by hand first. You might be surprised how few founders actually do.

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The #fundraising function is always-on for #VentureStudio founders. And many emerging studio leaders report it being much harder than they expected. In my experience, the problem isn't with the studio model, but rather the way it's being explained. The mechanics of running venture studios are different - and I'd argue more complex - than a typical startup or a VC fund. For many studio GP's, the instinct is to explain that complexity upfront. We sometimes call this the "Studio Monologue." Instead of leading with complexity, we help our studio partners win with clarity. Our framework turns scattered narratives into crisp, investor-ready theses. We cover this - and a lot more - in our latest paper - "The GP Dilemma: Escaping the Venture Studio Trap." I've linked it to this post - for free. Want to learn more? DM me and we'll find a time to connect!

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Three years ago, we launched Wisdom Ventures with a clear intention to support founders building at the intersection of well-being, human connection, and transformative tech. Since then, we’ve made 37 investments from our oversubscribed "minimum viable" $10M Fund I, backing early-stage companies in physical and mental wellbeing, women’s health, ethical AI, and human connection-centered innovation. We’ve always known we are on to something—what we didn’t expect was how quickly the data would back it up. Recent industry benchmarks show that most 2022-vintage emerging funds are experiencing the usual J-curve dip. In contrast, Wisdom Ventures is showing strong early performance: 📈 Net IRR (internal rate of return): >10% 📊 MOIC (multiple on invested capital): ~2x* ⏰ Median investment age: 18 months 💥 ....and # of our companies have a diverse founder by gender, race, or sexual orientation: 75% As we get ready to make our 38th and final investment out of Fund I and start deploying out of our significantly larger Fund II (first close May 1st), we’re filled with gratitude—for our founders, our LPs, our early supporters, our early believers, and this growing movement toward a more conscious, connected future, fueled by innovation from the ❤️ *Based on most current reports **Not in photo: Our fantastic operating partner, Zoe Rogers #WisdomVentures #ImpactInvesting #ConsciousTech #Wellbeing #AIForGood #FutureOfWork #VentureCapital

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I’m thrilled to announce defy.vc’s investment in Birches Health as part of their $20M combined Seed and Series A funding round, alongside incredible partners like AlleyCorp, General Catalyst, Will Ventures, and others. As someone deeply passionate about backing companies that tackle important problems for our society, I couldn’t be more excited about what Birches is building—a national virtual clinic dedicated to treating gambling addiction and related behavioral disorders like gaming, sex, porn, and internet addictions. What excites me most is Birches’ innovative health assurance model: proactive, accessible, and affordable care that’s evidence-based and delivered right at home. With the explosion of legal sports betting—think nearly $1.5 billion wagered on this year’s Super Bowl alone—we’re staring down a looming public health emergency. Traditional options like hotlines or generic therapy fall short for this high-acuity issue, but Birches changes that by offering specialized therapy from trained clinicians, multimodal treatment, and peer support, all covered by major insurers like United Healthcare, Cigna, Aetna, and Blue Cross Blue Shield. It’s available in all 50 states, breaking down geographical and financial barriers that have left so many without help. The impact is already profound: 96% of patients report an improved quality of life, and 94% give Birches a 5/5 rating. By partnering with state governments, payors, and policymakers, Birches is pushing gambling addiction into the spotlight of behavioral health conversations, where it’s been neglected for too long—often leading to shame, worsened outcomes, and higher suicidality risks. This funding will supercharge their growth: expanding the provider network, boosting clinical excellence, scaling infrastructure, and deepening insurance and state partnerships to meet surging demand. Very excited to partner with Elliott Rapaport and the entire Birches team! See more about our POV in the blog post linked in the comments. #GamblingAddiction #BehavioralHealth #HealthTech #VentureCapital #Innovation

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Seed VC isn’t just in a downturn—it’s facing extinction unless it evolves fast. Great read from Rob Go & David Beisel at NextView Ventures... - YC and mega-funds now dominate the early-stage landscape, squeezing out traditional seed investors - Power law thinking has gone mainstream—everyone’s chasing trillion-dollar outliers - AI isn’t helping seed VCs—it’s raising the stakes, crowding the field, and disrupting VC itself - The middle of the market has collapsed, and excess profits are gone - Hope isn’t a strategy—seed needs a new model, now Link here... https://lnkd.in/ek2MZGhm And if you like this topic, I wrote a piece on venture bifurcating into inception funds and mega funds here: https://lnkd.in/eJz5DmX6 #ai #venturecapital #vc

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Vibe coding products like v0 (Vercel) / Bolt / Lovable have created ~$100M ARR in 6 months. Prediction: this will grow to $1B in the next year for this suite of tools. There are two market dynamics happening simultaneously giving us a glimpse into the future: 1) Consumer phenomenon: vibe coding is trending on TikTok, and a brand new market of creators is emerging. This is akin to the number of microsoft excel users around the world, but way cooler. You can produce a site or app in seconds with no need to write code. 2) Future of enterprise software: with the ability to seamlessly prompt a user interface, enterprise platforms like Salesforce and ServiceNow will see their rigid UIs open up and be personalized for each users own preferences. My bet is 30%+ of UI of each of these will be user generated.

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If you look at the early-stage fundraising funnel, conversion rates are tightening, but the companies that do raise are doing so at higher valuations and with larger checks. The market seems to be betting on fewer winners, but those winners will be bigger. I’m not convinced. I do believe the very biggest winners will be larger than ever as AI expands the reach of technology, largely by replacing labor. But I don’t believe there will be fewer winners overall. Most B2B solutions are moving toward verticalized, specialized use cases that deliver superior value compared to generalized horizontal platforms. That shift should create more winners. While these vertical players may not reach the scale of the horizontal mega-winners, they can still generate the kind of multibillion-dollar outcomes that venture is built to fund.

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30+ VCs Backing Marketplace Startups Below is a cross-stage, cross-sector mix of firms that back marketplace and platform companies early and support them as they grow. Consumer and platform investors Upfront Ventures 1752vc (Formerly Pegasus) BAM Ventures Forerunner Brand Foundry Ventures Maveron BoxGroup Greycroft Alumni Ventures Marketplace natives and network effects specialists FJ Labs NFX Great Oaks Venture Capital RiverPark Ventures Left Lane Capital First Round Capital Lerer Hippeau Precursor Ventures Seed partners building two-sided platforms early Founder Collective NextView Ventures Uncork Capital Slow Ventures Bling Capital Gaingels Initialized Capital Felicis Multi-stage firms backing marketplace winners at scale Accel Bessemer Venture Partners Lightspeed General Catalyst New Enterprise Associates (NEA) Kleiner Perkins Bain Capital Ventures (BCV) Founders Fund

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