Stephen Llevano (@StephenLlevano) header
Stephen Llevano (@StephenLlevano) profile picture

Exited Founder & Operator - Commercial Real Estate Expert

San Francisco, CA
Joined July 2012
Photo by Stephen Llevano (@StephenLlevano)Photo by Stephen Llevano (@StephenLlevano)Photo by Stephen Llevano (@StephenLlevano)Photo by Stephen Llevano (@StephenLlevano)Photo by Stephen Llevano (@StephenLlevano)Photo by Stephen Llevano (@StephenLlevano)Photo by Stephen Llevano (@StephenLlevano)Photo by Stephen Llevano (@StephenLlevano)
Stephen Llevano retweeted
The product wasn't the problem The advice he got on the one thing a working product couldn't fix? "It's gonna take you more than 2 years to change consumer behavior..." The takeaway? Don't burn years changing consumer behavior when you can build where demand already exists @RIsanians, CEO & Founder, Mage Legal on @fondocom START Full ep here: fondo.ai/4irWXQ4 Learn more: fondo.ai/4h4af2N
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Stephen Llevano retweeted
The classic trap: build first, find the buyer second You can't out-engineer consumer behavior
The product wasn't the problem The advice he got on the one thing a working product couldn't fix? "It's gonna take you more than 2 years to change consumer behavior..." The takeaway? Don't burn years changing consumer behavior when you can build where demand already exists @RIsanians, CEO & Founder, Mage Legal on @fondocom START Full ep here: fondo.ai/4irWXQ4 Learn more: fondo.ai/4h4af2N
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Stephen Llevano retweeted
I’m actually very surprised that a guy who moved to Atherton, became a brand ambassador for Loro Piana, and then weaseled a few billion out of the worst SPACs of all time believes that Silicon Valley only cares about money.
Chamath says Silicon Valley lost what made it great and only cares about money now "Silicon Valley has completely lost what made it great. It was a place for weirdos, for people at the fringes, for people that really were idealistic. And it has become something that's far from that now. It is the equivalent of what Harvard used to be. It's a credentialing place." "When we came, we used to aspire to meet the Bill Campbells of the world, Mike Moritz, John Doerr. Those folks are gone. We used to aspire to work for Steve Jobs. He's not here." "And in that breach, all we have done is focused on making money in every single way that we can, hand over fist. And there's nothing wrong with that. Except now it’s at a point where we need to do a better job of acknowledging it and trying to do a little bit better.” “Every time we don't, and we're given a chance to be better, and we're not, the hatred builds, the animus builds. And that's what we're seeing now."
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Stephen Llevano retweeted
In Defense of Writing. A disturbing trend I see emerging is people lazily generating longer form content from bullet points or dictation they give to an LLM, and then passing it off as their own. Beyond the obvious breach of trust and social expectation when doing this, there are several more nuanced but equally insidious problems with doing this. First, writing is thinking. If you aren't taking the time to write, edit, rework, reshape, and play with your words, you're shortcutting a key aspect of refining an thought. You rob yourself of this opportunity if you just skip to the end. I have yet to read anything generated that even comes close to the clarity and impact of a well-written piece. Second, respect. Very few people will tell you this to your face, but as soon as they read something 'from you' that has all the tell-tale signs of AI slop, their respect (and trust) for you drops. What you are communicating is that you don't take the time and effort to do things properly, or at least entirely honestly. This is damaging in way many don't realize. I instantly discount anything I read as soon as I recognize it as AI slop. Third, and I think most important, you are training yourself to take the easy way out. I think this is different than 'working smart'. It's intellectual laziness, effectively choosing cheap calories rather than a nourishing meal, even if it takes longer to prepare. That effort is where good things, as well as your own growth, come from. Many days on here I feel like the last man alive who wants to actually read what you wrote. It's entirely possible that this is a losing battle and the nature of media and medium is trending in an irreversible way. But I really hope it's not. I'll leave you with a philosophical question: every social media platform is going to great lengths to label AI-generated images and video. Why not writing, as well?
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Stephen Llevano retweeted
Today, Substack is launching an AI detection feature, via an integration with @pangram. Going forward, you’ll be able to scan posts, replies, and comments on the Substack app to see an estimate of how much of it was written by a human, or with AI assistance.
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Stephen Llevano retweeted
We keep hearing about 10x or 100x productivity gains in engineering and knowledge work. But outside the model labs, I haven’t seen the corresponding 10-100x revenue growth across the market or increase in quality. So where is the productivity going?
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Stephen Llevano retweeted
new model for engineering team structure in 2026: 2 people only one pirate and one architect the pirate's job is to move as fast as possible to develop valuable, shipped product features by vibe coding. the architect's job is to turn the product surface discovered by the pirate into a reliable, structured machine—also by vibe coding, but at a slower, more well-reasoned pace. every product needs a pirate but most product's only need an architect once they some form of PMF, and in that case they usually don't need one full-time. architects can work across many codebases and solve interesting technical challenges. pirates go hard on a product that they own end-to-end.
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Stephen Llevano retweeted
Public SaaS multiples crashed ~70%. Private AI companies trading at 500x revenue @vivekramaswami co-wrote a piece called "The Price is Wrong." His take: both sides are mispriced Some of those beaten-down software companies are systems of record that aren't going anywhere You can't vibe code an endpoint security solution And on the AI side, 20 companies building in the same vertical aren't all going to be multi-billion dollar outcomes After 11 years of investing across RedPoint, Steadfast, and Madrona, his filter keeps coming back to one thing: the founder. Markets move. Models change. The founder is the one constant And the way he works with founders says a lot. He doesn't pretend to have the answers. He shows up, listens, asks the right questions, and lets the founder get to the conclusion they were already circling 🎙️ @vivekramaswami, Partner @MadronaVentures on @fondocom @thestartpod w/ Guest Host @StephenLlevano 03:03 From Goldman to venture 07:36 Finance discipline meets founder pattern recognition 12:03 Founder quality over static metrics 15:22 Board members as guides, not operators 21:07 The psychology behind founder decision-making 24:17 Supporting the founder while serving the company 26:33 Learning technical markets without being technical 29:55 AI and the changing role of junior talent 32:00 Sourcing, agents, and the new venture workflow 38:49 Small teams, but still the right teams 44:41 Bigger companies, fewer winners, changing venture math 47:37 Multiples, mispricing, and why durability wins
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So excited for this one to finally come out. Thanks again to @vivekramaswami for the great conversation! Always a blast getting to catch up with you my friend.
When AI can handle more of the research, synthesis, and first-pass thinking, the value of junior roles doesn’t vanish ...but it does start to shift Tomorrow on @thestartpod: @vivekramaswami, Partner @MadronaVentures w/ guest host @StephenLlevano
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Stephen Llevano retweeted
He didn’t leave Big Law to build just another legal tech tool. @RIsanians knows what most founders learn too late: don't change consumer behavior before the market is ready He's building Mage Legal, automatic AI M&A diligence across your entire data room 🎙️ Full ep next week on @thestartpod with Guest Host @StephenLlevano and Special Guest @RIsanians, CEO & Founder of Magelegal.com
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All these Ai wrapper products feel like the drop shipping of software. Buy something “cheap” repackage and make a slight “markup”
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Stephen Llevano retweeted
Full ep next week on @thestartpod with Guest Host @StephenLlevano 🎙️ fondo.ai/4st1DHi
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Is @Apple having their “BlackBerry moment” with iOS 26?
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Stephen Llevano retweeted
The best product builders are relentless product users. Taste comes from opening apps, stumbling through onboarding flows, hitting walls, and feeling the difference between smooth and clunky. Chefs don’t learn taste from recipes. They taste food until they can tell what’s missing. Product builders do the same. Sign up for more tools. Break them. Sit through the frustrating ones. Pay attention to the ones that pull you back. Over time, those experiences wire your intuition. You stop guessing what “good UX” looks like. You know, because you’ve lived the whole spectrum from delightful to disastrous.
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Stephen Llevano retweeted
✨Today I'm launching Paraspeech on Producthunt. It's one of the fastest real-time speech to text apps for Mac and it's: •⁠ ⁠100% offline and on-device •⁠ ⁠<40ms cold-start time •⁠ ⁠⁠<300ms transcriptions •⁠ ⁠barely touches battery & just needs 200MB of RAM •⁠ ⁠⁠no subscription! First 100 people get it for $19.99 before prices increase to $39.99. If you tweet about, I'll send you a free lifetime license.
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So fun hanging with @davj and talking about our experiences as startup founders! If you’ve got some time, give it a listen!
Some founders ask what customers want... Stephen watched what they actually did (and that changed everything) Now capabuild.app solves problems others never noticed And users feel the difference
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Stephen Llevano retweeted
Some founders ask what customers want... Stephen watched what they actually did (and that changed everything) Now capabuild.app solves problems others never noticed And users feel the difference
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