Stand Insurance, Former CEO HotelTonight

San Francisco, CA
Loved @bgurley’s Runnin’ Down a Dream - highly recommend. It hit at the right time as I think about my next decade. The biggest takeaway for me: follow fascination, not passion.
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An idea for @Tesla navigation: optimize routes based on real-time traffic light sequencing. Example: if going left or straight at a traffic light takes the same amount of time to get to your destination, but the left-turn arrow comes before the main green, the car should choose based on the light state. Green main light? Go straight. Red light or Green turn arrow? Take the left.
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Had @Starlink on a @united flight last week - it's amazing how good it is. One idea is that the hardware should include accelerometers to track flight turbulence and create a real time map of flight conditions to aid other pilots in avoiding turbulent areas.
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Really proud of what we are building at @standinsurance. Big vision, exceptional execution, and a mission that matters more every year.
Introducing Stand’s World Model, a physics-native frontier model for the built environment. This is how we help the world survive catastrophe: by computing how physical force acts on a structure, protecting property from fire, wind, flood, or earthquake.
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Demo day for @speedrun 006 underway!
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Congrats @JeffreyChernick! Was very fun to work with you on a chapter in this book - perhaps the closest I'll ever get to writing my own book!
#1 New Release on Amazon 🏆 High Five Energy just hit #1 in "Starting a Business" on Amazon Hot New Releases. Thank you to everyone who grabbed a copy. This is just the beginning. 18 legendary founders. $200B+ in exits. Real stories about what it actually takes. Link in bio to grab yours. #bestseller #highfiveenergy #entrepreneur #startups #founders
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Hey @jgebbia design idea for you. I had federal court jury duty the past 2 weeks - I was happy to do my part for the judicial process, though I had to login to the website each day at 5pm to check my status. Tedious and easy to forget! I should have been able to sign up for an email or text status alerts.
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Fun talking with you @kentlind! Covered a lot of territory and lessons learned.
Latest episode with @samshank, who built @HotelTonight the groundbreaking last-minute hotel booking app acquired by @Airbnb . How HotelTonight cracked the App Store rankings, turned perishable hotel inventory into gold, and ultimately became a perfect strategic fit for Airbnb.
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Sam Shank retweeted
Latest episode with @samshank, who built @HotelTonight the groundbreaking last-minute hotel booking app acquired by @Airbnb . How HotelTonight cracked the App Store rankings, turned perishable hotel inventory into gold, and ultimately became a perfect strategic fit for Airbnb.
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AI is about to change how we buy things. The last generation of marketplaces optimized for search: List the inventory. Add filters. Sort by price. Remove friction. That playbook is exhausted. What comes next are AI-powered marketplaces with agents that work for you - not just showing options, but advocating on your behalf. Key things they will do: • Understand your constraints and preferences • Decide when to buy, not just what • Negotiate across sellers to get the best outcome Instead of scrolling, you’ll delegate. The future of commerce isn’t better discovery. It’s decision-making and execution on your behalf.
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For more Big Ideas from the @speedrun team, subscribe to our newsletter here: speedrun.substack.com/
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Sam Shank retweeted
Excited to share that I’ve joined @a16z as an Investment Partner. I’ll be focusing on early-stage investing as part of a16z @speedrun, where we invest $1M in new startups and help them scale. I first got to know a16z when I joined Lyft in 2019, where the firm was a major investor and Ben was on the board. I’ve always admired their unique approach to venture as a product, focus on content marketing, and culture of deep respect for the entrepreneur. I’m thrilled to now join and serve founders alongside @andrewchen, @Tocelot, @JoshLu, @tkexpress11, @emilybenn12, @custo_lejla, @samshank, @far33d, @marcussegal, @ndrewlee, and the rest of the team. Thank you to the incredible team at @BainCapVC – who gave me my first introduction to venture and the best training I could’ve asked for. If you’re working on something new – I’d love to hear from you. It’s time to build!
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Sam Shank retweeted
Thanks for chatting with us today @samshank! ☺️ As a power user of HotelTonight, it was extra special. Some things that stuck with me: HotelTonight became a category leader because it created a new market vs Sam’s earlier companies were just better versions of existing products Distribution matters as much as product. HotelTonight was mobile first when the AppStore first launched which gave them a leg up. As an investor, he now looks for founders with a unique distribution wedge 🧀 @Techweek_
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Last call for @speedrun applications! They close tonight at 11:59pm pt. Get ‘em in!
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Don’t start with the product. Start with distribution. I give this advice to entrepreneurs all the time because distribution is the hardest part of building a company. “Build it and they will come” almost never works. And even if you expect distribution to be hard—it’ll be 10× harder. HotelTonight started with a distribution insight. In 2009, we saw that the App Store about to become a massive channel. Billion-dollar companies would be built there, and early movers could earn free distribution before the competition showed up. From that insight, we worked backwards to the product: - A use case uniquely suited to mobile: last-minute hotel booking - Designed to win App Store ranking and retention: beautiful UI, lightning-fast 8-second bookings - Clear, curated choices and amazing deals that fit the mobile moment That combo—a unique distribution edge + a product tailored to it—powered our growth. As you think about your next company, begin with your edge in distribution. Maybe you are an expert at selling into a specific vertical. Maybe you're great at creating authentic content. Maybe you’ve spotted an emerging channel before anyone else. Only then decide what to build—the product that best amplifies your distribution advantage. At speedrun, we’re seeing teams win with GEO, founder-led content, and high-intent launch videos. So I’ll leave you with a prompt: What’s your unique approach to distribution—and what product could you build that maximizes it? If you’re working on this, I’d love to hear from you. Apply to @speedrun at sr [dot] a16z [dot] com.
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Big news! I'm joining the @a16z @speedrun team as a Visiting Partner. I'll be mentoring pre-seed/seed startups in the next cohort—helping founders move faster and I’m particularly excited to work with teams building AI-first marketplaces, AI consumer apps that reimagine how we tell stories and are entertained, and AI agents to enhance or augment labor. Why now? I’ve loved advising startups 1:1, and this lets me do it at scale with a crew that’s all-in on tech, entertainment, and AI. As this role is part-time, I'll continue building @StandInsurance and advising travel and marketplace companies. Applications for the upcoming cohort are open now so I’d encourage you to apply as it would be great to get a chance to work together.
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