Building Roll Up Vehicles and Consolidation Vehicles at @RollupsHQ

Joined June 2020
62 Photos and videos
Joshua Webster retweeted
Jun 12
History's first trillionaire is a guy who catches rockets out of the sky with chopsticks and beams internet to every dead zone on the planet. Same guy ships cars that drive themselves, humanoid robots for the factory floor, brain chips that let paralyzed people move a cursor with pure thought, and an AI running on a supercomputer his team stood up in months instead of years. And the people crashing out about his net worth are doing it on the app he owns. The same app governments spent years trying to censor. You cannot legislate a rocket into orbit.
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Joshua Webster retweeted
Oh yes, I remember that Bond film where the villain decarbonized the auto industry, brought fast internet to everyone on the planet, and helped paralyzed people interact with the world again.
Elon Musk is a real-life Bond villain ft.trib.al/zAOuVKk
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Joshua Webster retweeted
I’m at the bottom of a multi-layer SPV and am looking forward to the SpaceX IPO in much the same way a golden retriever looks forward to a car ride: - thrilled to be involved - no clue how cars work - unsure if going to the park or getting neutered
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Joshua Webster retweeted
The world is run by people who give a shit.
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Not to publicly rant but @qatarairways @British_Airways We booked SEA–BKK via DOH using Avios and were involuntarily moved from our original DOH–BKK flight to another aircraft, resulting in an involuntary downgrade. There is a similar flight with seat availability. Please assist.
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@British_Airways, waiting on you here. @qatarairways followed up and noted this was a British Airways problem. @USDOT are airlines allowed to downgrade passengers without compensation or warning?
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Joshua Webster retweeted
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Joshua Webster retweeted
17 May 2025
Replying to @jordanschneider
Or how about we let free market capitalism work and let American companies innovate and win without burdensome red tape and regulations on top of government bureaucrat central planning on pricing and distribution? This is not some magic chip alchemy. It’s just the next generation of compute. The AI doomsday narrative is conflated and not based on technology reality. If bureaucrats were in charge during the PC revolution, American x86 and WinTel would not have been able to dominate for decades. Free markets work. Government involvement and intervention generally does not (hello Soviet Union). If the government was smart, they would do a nuanced strategy of letting China remain on CUDA but one or two generations behind (keeps USA ahead) - instead of literally creating a chip competitor ecosystem with tens of billions of R&D oxygen from the biggest chip market in the world. Basically, let Nvidia cook.
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Joshua Webster retweeted
Feb 23
When I was 7 years old I was asked by my father what went into the price of a sandwich. Considering it carefully, I answered. The lettuce, the tomato, the bread and the meat. I did not consider correctly. I was short quite a few costs as my father was eager to point out. I had forgot the labor of the worker, the rent of the land, the marketing costs of the chain. I wasn’t seeing the full picture. Today we are all making a similar mistake with AI. We are not considering what cannot be considered. As foreign to the 7 year old as these excess charges were, so are the downstream affects of AI. In 1850, if you had told a teamster that his horse and carriage would soon be obsolete, he would have envisioned a world of mass starvation for men of his skill. He could grasp the concept of a faster carriage, but he could not conceive of the interstate highway system, the suburban real estate market, or the roadside motel industry. These were not just new products; they were an entirely new social architecture. We are currently in the teamster’s shoes. We see AI automating the ingredients of our current economy—the writing, the coding, the data entry—and we fear the void. But history shows that humanity doesn't fall into the void; it builds a floor over it. Karl Marx looked at the dark satanic mills of the 19th century and saw a terminal point. He argued that as the means of production became more efficient, capital would consolidate and labor would become a worthless commodity. He believed capitalism would eventually eat itself because it would run out of things for people to do. Marx was wrong because he viewed human utility as a fixed pie. He didn't understand that technology doesn't just subtract labor; it changes the nature of what we consider valuable. When the mechanical loom made fabric cheap, we didn't stop buying clothes. Instead, we invented the fashion industry. We created brand management, retail psychology, and textile engineering. We moved from a world where everyone owned two outfits to a world where millions of people are employed in the cycle of seasonal trends. In the age of the steam engine, "handmade" was a sign of poverty. Today, it is a luxury. We are already seeing a shift where the human touch—the artisanal, the face-to-face, and the physically present—is becoming the high-margin sector of the economy. Every time we automate a simple task, we move the human to a more complex one. We didn't stop needing accountants when Excel was invented... we simply started asking accountants to perform much more sophisticated financial modeling. The 7-year-old misses the rent and the marketing because they are abstractions. Similarly, we struggle to see the jobs of 2040 because they rely on problems we haven't even encountered yet. We might see the rise of Personal Data Stewards, who manage the interaction between our private lives and public AI models, or Reality Architects, who ensure that the virtual spaces we inhabit are psychologically grounded. The world works itself out because humans are fundamentally restless. We do not tolerate a vacuum of purpose, we seek higher function always.
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Poasters when a new meme format drops
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Joshua Webster retweeted
Introducing: Secondary Vehicles Now companies can run their own secondary SPVs for delivering liquidity to shareholders without the predatory SPV fee/carry structures.
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Joshua Webster retweeted
"I'm raising a round, can you introduce me to X investor" — question i've had 1,000 times in the past 10 years. and another 1,000 times in the past 10 days 😆 Answer is often* "yes - but please send me something forwardable easily parsable, give yourself best chance of passing the 2-second inbox scan test" Back in 2015 i was the guy who wrote all the "featured startup" emails at AngelList .. email blasts sending out "active rounds" to thousands of online investors. I had the unique privilege of @nivi breathing down my neck, helping pedantically craft every word until we got the formula, format just right. That formula is the one i still use/recommend today. I've been meaning to share it in public, so i can sign-post back for founders requesting intros. And, here we are. So. If you want me to fwd something to someone for you, please send: four bullet points. no more, no less. Each bullet is one sentence, maybe two.. but it's not an excuse to write a paragraph. 1) what does your company do, what problem are you trying to solve? 2) what traction do you have, or how do you know it's working. why is this notable? 3) who is your team, why are they the right people for the job? 4) what's your fundraise status - past & future plans? "raising a seed round, targeting ~$X. ~$Y committed so far, led by ABC. Prev raised ~$Y from D, E, and F." #4 can be a hard one, highly dependent on where you're at in your journey....maybe you're just testing the waters on the round, in which case say that - "planning to go out for a pre-seed next month." If you list investors as committed/previously invested, make sure they actually are (and ideally investing again) because someone will probably ask them. Founders, does that help? Other investors, what would you suggest/iterate on this format? What's your dream intro request to receive?
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Joshua Webster retweeted
14 Nov 2025
Mo (founder of @frecfinance, backed by Greylock) used an RUV to raise $5.6M from his top customers. RUVs have grown entirely through word of mouth. Founders, investors, and lawyers love them. We did very little marketing and no advertising; we just focused on building a great product.
12 Nov 2025
We just raised $5.6m from our top customers on Frec, and the round was oversubscribed in under 48 hours! Here’s how it all went down. Customers have been asking to invest in Frec since we launched, so we kept track of those who asked, provided valuable feedback, or referred customers. The list started growing quickly after launching long short. Although we had the bulk of our Series A still in the bank, we saw an opportunity to make our top customers owners in Frec. So I pitched the idea to the board. The pitch was simple. Customers who want to invest work at some of the most impressive companies in the world, like Nvidia, Meta, Apple, Netflix, Snowflake, Databricks, Stripe, Shopify, Uber, Robinhood, Plaid, Workday, Block, Two Sigma, JP Morgan, and more. Their colleagues are exactly the type of people who could benefit from Frec the most. Offering these customers ownership would create an incredible customer advisory board. The board agreed. And when I sent the invites to the customers, the reactions were heartwarming: “Heck yes, I’m 100% in. Thank you for thinking of me for this. I’d love to be part of it. You know I’m very bullish on Frec’s future.” “I am impressed with how smart it is to engage your best customers with ownership this way.” “I'm glad to be a customer and now glad to be an investor. Eager to see how things grow and develop.” …and many more 🙏 So we raised the money in a YC SAFE note for a fast and efficient close, and we used an AngelList Roll Up Vehicle (RUV) to keep our cap table clean. I’m excited to welcome our newest investors. We always value customers who engage with us and hope to include more of them as investors in future opportunities.
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An excellent example of how using a Roll Up Vehicle can supercharge your fundraise while including your top supporters (your customers)!
12 Nov 2025
We just raised $5.6m from our top customers on Frec, and the round was oversubscribed in under 48 hours! Here’s how it all went down. Customers have been asking to invest in Frec since we launched, so we kept track of those who asked, provided valuable feedback, or referred customers. The list started growing quickly after launching long short. Although we had the bulk of our Series A still in the bank, we saw an opportunity to make our top customers owners in Frec. So I pitched the idea to the board. The pitch was simple. Customers who want to invest work at some of the most impressive companies in the world, like Nvidia, Meta, Apple, Netflix, Snowflake, Databricks, Stripe, Shopify, Uber, Robinhood, Plaid, Workday, Block, Two Sigma, JP Morgan, and more. Their colleagues are exactly the type of people who could benefit from Frec the most. Offering these customers ownership would create an incredible customer advisory board. The board agreed. And when I sent the invites to the customers, the reactions were heartwarming: “Heck yes, I’m 100% in. Thank you for thinking of me for this. I’d love to be part of it. You know I’m very bullish on Frec’s future.” “I am impressed with how smart it is to engage your best customers with ownership this way.” “I'm glad to be a customer and now glad to be an investor. Eager to see how things grow and develop.” …and many more 🙏 So we raised the money in a YC SAFE note for a fast and efficient close, and we used an AngelList Roll Up Vehicle (RUV) to keep our cap table clean. I’m excited to welcome our newest investors. We always value customers who engage with us and hope to include more of them as investors in future opportunities.
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Joshua Webster retweeted
Replying to @sumukhsridhara
SAFE.new is the hidden gem in this update. Send SAFEs with no account or sign up process required.
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Joshua Webster retweeted
Introducing: SAFE fundraising USDC. Sign SAFEs in seconds & get funded even faster. Here's signing and funding an investment in 15 seconds.
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Joshua Webster retweeted
Love to see it: The team at @rollupsHQ is giving all startups that raise a RUV with them a free annual subscription to my newsletter (which comes with the Product Pass, over $13,500 in value—a free year of @Linear @n8n_io @gammaapp @Superhuman @warpdotdev etc). I invest in RUVs (Roll Up Vehicles) all the time because they make it easy for founders to raise money from a bunch of investors while keeping just one clean line on their cap table. Check it out → rollups.com/lenny
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Joshua Webster retweeted
25 Sep 2025
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Joshua Webster retweeted
Important chart. S&P 490 has had basically no earnings growth since 2022, despite rampant inflation. It’s just 10 companies doing really well, while the broader economy is in contraction in real terms.
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Joshua Webster retweeted
7 Aug 2025
Unless your dollar-denominated net worth has increased by at least 11% this year, you've become poorer. The dollar has decreased about 10% in value since Trump took office, so your net worth would have to increase by 11% for you to break even.
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