You are far more dangerous to your startup than competitors are. A hundred times more startups die from poor execution by their founders than are killed by competitors.

When COVID hit, my company at the time was one of the first things hotels cut. That experience taught me one of the most important lessons of my career. I had built a marketing technology company for hospitality. Good product, real clients, and the kind of logos you put on a deck with pride. Then 2020 arrived. Hotels went into survival mode. And I watched, in real time, which vendors got kept and which got cut. Marketing tools got cut. Mine included. Not because they were bad, but because when an owner is fighting to keep the lights on, the campaign tool is the easiest line item to delete. It doesn't touch the rooms. It doesn't make a reservation. It's a nice-to-have. And nice-to-haves die first. The systems that survived were the ones tied directly to revenue and operations. The PMS. The reservation system. The phone. The things hotels literally cannot operate without. Sitting back home in Puerto Rico, I spent a lot of time thinking about what had just happened and what I wanted to build next. That experience changed the way I think about building companies. I realized I never wanted to build a nice-to-have again. I wanted to build something that helps hotels make money, save money, and run better every single day. Something that sits at the center of operations, not on the edge of it. That lesson became the foundation for withQ. Today, we're building AI agents that help hotels capture bookings, answer guest questions, automate operations, and support teams across voice, SMS, chat, and messaging. Funny enough, the hardest quarter of my career ended up teaching me the most valuable lesson: Build for the operations budget, not the marketing budget. Be the thing they can't imagine unplugging.

It’s pretty insane to see founders having to juggle fundraising, managing runway, making product decisions, traveling to the edges of the earth to meet customers, managing board expectations, keeping the culture alive.. all with utmost composure like everything is going to be okay. Very few jobs have that much context switching, chaos, competing priorities, and uncertainty. Just superhuman stuff.

The best pitch test: can you tell this at a bar to a friend? Not the market size, not the TAM, not the deck. Just the story. Why you built it. What you saw that nobody else saw. What happened. If you can't tell it naturally over drinks (or it would feel weird to your friend and they would think "this isn't you"), your idea or pitch or endeavor needs to bake some more. The 9pm-at-a-bar test for your startup idea is a defining authenticity test. And without that, nobody will buy your product, let alone come work for you or invest.

The next wave isn’t software you use. It’s AI workers you hire.

I was talking to a hotel owner last week who pays Marriott 8 to 12 percent of every booking in franchise, reservation, and loyalty fees. His abandonment rate on inbound calls? Around 40 percent. He's paying for demand capture. Then losing it. Marriott just reported Q1 2026: Revenue: $6.65B ( 6%) Fee revenue: $1.4B ( 13%) RevPAR: 4% Fees are growing about 3x faster than the hotels paying them. That is not an accident. It is the model. Marriott owns less than 1 percent of its roughly 9,900 hotels. The fees are the product. Which is fine until you look at what owners are actually buying: The brand The booking engine The loyalty program The call centers And that last piece is where it breaks. High intent guests, people ready to book, hang up. At peak hours. After every fee in the stack has already been paid. Distribution is solved. Response is not. The next layer is not more channels or more fees. It is execution. An AI layer that actually picks up, so the demand owners already paid for does not walk away.

I tried to give a hotel money last week. Nobody picked up. That’s how I opened my talk at the Puerto Rico Hotel & Tourism Association. The numbers behind that one missed call 20 to 40 percent of inbound demand is missed 100K to 250K per hotel lost every year 30 to 73 percent staff turnover. The people who could have answered are not there Hotels don’t have a demand problem They have a response problem The industry knows it 73 percent of hoteliers believe AI will have a significant or transformative impact on their business 77 percent are already moving it from experiment to a core budget line Three things I wanted every operator in that room to walk out with 1. AI does not replace your PMS, POS, or CRM. It activates them 2. This is no longer an IT decision. It is an operator decision. ROI first 3. You will not be replaced by AI. You may be replaced by someone who uses it better Puerto Rico is moving fast. The Caribbean is becoming one of the most aggressive regions for AI adoption in hospitality, and the results are already showing up Huge thank you to Clarisa Jiménez Mayoral for the invitation and Discover Puerto Rico for the support The hotels that win will be the ones that respond the fastest

vc’s don’t build conviction through decks they use decks to justify conviction they already have in the founder by the time you’re presenting they’ve already decided

In honor of 50 years of Apple, we're sharing - for the first time ever - Don Valentine's original 1977 memo for Sequoia's investment into Apple Computer. #Apple50

Every founder and CEO should read all they can about the drama triangle. If you cannot face another person directly, you will drag a third person in and call it process. That is how companies rot from the inside.

men in their 40s used to have cool midlife crisis but now they just have agentic workflows

Consider that the dumbest people you know are repeatedly being told "You're absolutely right!" by LLMs.

How much is a missed booking worth to you? For most hotels, capturing just 2 extra bookings a week via Voice AI covers the entire cost of the platform. The rest is pure profit. Q Concierge acts as your most reliable sales agent, ensuring no inquiry goes to voicemail. Calculate your ROI at bit.ly/4pQ4OHe #hospitalityindustry #hotelbusiness #hotelowner #hotels #travel

Two years into building this company I’ve learned something simple: Startups are mostly a test of patience. Most days look pretty ordinary emails product tweaks customer calls deals that take twice as long as expected But over time it compounds quietly. Until one day you realize how far you’ve actually come. Still building.

I took this photo last week at a ski resort in Tahoe. Beautiful property. But it’s been a tough winter for many resorts. Across the West, ski conditions have been inconsistent. Some destinations are seeing noticeable drops in international visitors. And economic headwinds are putting pressure on resort operators everywhere. In seasons like this, every booking matters. One of the biggest revenue leaks we consistently see at resorts is the voice channel. Guests still call. A lot. They call to book rooms, ski lessons, lift tickets, spa appointments, dining reservations, transportation, and activities. But during peak hours, storms, weekends, and after hours, many of those calls go unanswered. Every missed call isn’t just a missed conversation. It’s a missed booking. At a ski resort that often means losing the entire guest journey. Room stay Lift tickets Ski school Rentals Dining Spa Activities In a challenging season, capturing the demand that already exists becomes critical. That’s exactly why we built @withqconcierge Our Voice AI workforce answers every guest call instantly, 24/7, and handles bookings, reservations, FAQs, and transfers across the entire resort. Across our ski resort partners, the pattern is consistent after deploying Q Concierge: missed calls drop, booking conversions rise, and reservations teams finally get breathing room during peak weekends, storm days, and after hours. No hold times. No abandoned calls. No lost revenue. When resorts are fighting for every booking, the phone should never be a bottleneck. Curious how much revenue might be hiding behind your busy signal?

Sequoia (@sequoia) Partner @JulienBek tells us why the next $1Trillion company will be a software company masquerading as a services firm: "Ultimately, if you look at the TAM today, for every dollar that you spend on software, $6 are spent on services". "If you sell the tools, the models are getting better and better and so you're at risk... whereas, if you sell the services, you're actually delivering outcomes." "Until now, we could really just go after the $1, but now with services first and human at the centre, we think you can capture the six".

One thing I’ve always liked about Silicon Valley. When people make money, the natural instinct is to start angel investing and help the next generation of founders. In a lot of other cities, the instinct is to buy a Ferrari. Just a very different culture.

Q Concierge doesn't just talk; it acts. Our Voice AI syncs directly with your PMS to log requests, update checkouts, and route tasks without a human lifting a finger. Modern tech for a timeless industry. Check out our ROI today at bit.ly/4pQ4OHe. #hospitalityindustry #hotelbusiness #hotelowner #hotels #travel

Not a bad winter day in San Francisco 🌁☀️

Hot Take: If your staff is too busy answering "What's the Wi-Fi?" to look a guest in the eye, your human touch is already gone. Automate the routine. Save the hospitality. Book a demo at bit.ly/4pQ4OHe. #hospitalityindustry #hotelbusiness #hotelowner #hotels #travel