Mike Demson @MikeDemson

Building a home for my own family has been the most challenging project of my life. Budgets, permits, and inspections are the easy parts. The hard part is knowing that every decision shapes the place where my wife and son will live, where memories will be made, and where our family will grow. Today, we passed the final inspection from the Fire Marshall. On paper, it appears to be a small step. In reality, it represents years of planning, long nights of problem-solving, and the kind of patience I did not know I had. When it is your own home, every delay feels heavier. Every milestone feels like a gift. The truth is, building is not one big win. It is hundreds of small ones stacked together until the day you finally walk through the door and get a certificate of occupancy. What is the most meaningful project you have ever completed?

Everyone told us to pivot at 400 Bay St. “Why not build apartments? Why not condos? Forget the hotel, it’s too risky.” We ran the numbers. We looked at the trade-offs. Apartments meant no retail. Condos meant parking instead of ground-floor value. Here’s what we found: Apartments have stability, but a lower ceiling. Condos offer the fastest return on investment, but lack long-term durability. Hotels, when done right, combine both. By keeping the boutique hotel, we not only secured the best risk-adjusted return profile, but we also added $1 million in value to the property just by keeping retail on the ground floor. And we still like apartments. We’re moving forward with 258 units at 360 5th St, where rents have increased by 11% in the past year, thanks to the AI boom in SoMa. We still like condos. We’re pursuing entitlements in Stinson Beach, one of the most supply-constrained markets in California. But 400 Bay St is different. Here, a boutique hotel makes sense. We can operate it like a furnished apartment building, powered by technology and automation, while unlocking a much higher ceiling than apartments could ever deliver. What would you have chosen: apartments, condos, or a hotel?

@realEstateTrent San Anselmo and Fairfax should be included

Apartments aren’t supposed to be less efficient than hotels. That’s what the “experts” told us. When we showed a 35% expense ratio on our Sonoma boutique hotel, an appraiser nearly walked out of the room. But we knew something they didn’t. We built a staff-light model powered by AI: •Guests get a code that activates at check-in and expires at checkout. •Automations upsell early check-in, late checkout, and pet packages. •The system even recommends local spots with exclusive offers. The result? A boutique hotel operating leaner than most apartments without sacrificing guest experience. Conventional wisdom said it couldn’t be done. We’re proving it every day. What’s the assumption everyone told you was impossible until you showed the numbers?

@ChidaRajan Let me know when you find out

Airbnb will not replace hotels. I can say that because I lived in both worlds. I was an early employee at Airbnb. I watched a scrappy startup transform how the world travels. It was fast, exciting, and built on scale. Today, we are developing boutique hotels from the ground up. And here is what I have learned: - Airbnbs scale quickly, but consistency is hard. - Hotels move more slowly, but you control brand, design, and guest experience. - The best hospitality assets are not about growth at any cost; they are about creating memorable experiences that last. That is why hotels will outlast Airbnbs in the decades ahead. I shared the full story with Rich Somers on his podcast, from my time at Airbnb to building hotels in San Francisco and Sonoma. Full episode: youtube.com/watch?v=7Nq7U0… Airbnbs are best for groups that want to all be together. Hotels are best for memories that last a lifetime. Which side are you on?

We're preparing to process building permit submittals for the 33 custom home subdivision in Sonoma County. The most important ally I made wasn't an engineer or a city planner. It was the fire chief. When we acquired 42 acres for housing, I knew one thing could kill the project before it even started: fire access. In Sonoma, nothing stops a project faster than safety questions. So I didn't wait for conditions to be handed down. I called the chief. I stopped by the fire station and met with him face-to-face. We climbed into ATVs and drove every inch of the property. We checked slopes. Turnarounds. Staging areas for fire trucks. By the end of the day, we had a plan that worked for him, and more importantly, we had trust. That ATV ride did more for this project than any consultant report ever could. It showed the fire department that we were listening. It showed the community that their safety was at the center. Here's the lesson: Development isn't only about design, engineering, or finance. It's about relationships. You'll never earn approval if you don't earn the trust of the people who keep the community safe. What's the most unexpected thing you've done to build support for a project?

I spent the first decade of my career trying to avoid real estate development. I did what I thought I was supposed to do. I went to a reputable school, earned good grades, and worked in the tech industry. On paper, it made sense. I was an early employee at Airbnb and thought that was the path I was meant to follow. In reality, it never felt like something I could build on. The truth is, I grew up on jobsites. Summers and weekends were spent with my dad in Carmel, working on Tehama, the community Clint Eastwood developed after his tenure as Mayor. My role was not glamorous. I was a hod carrier. I spent entire days in the heat loading, unloading, and mixing 80-pound bags of cement by hand. Hour after hour, bag after bag. That is where I built strength, resilience, and determination. Those summers taught me the lessons that still matter most. Show up early. Do the hard work. Do it right. Your reputation lives in every project you touch. For years, I thought I had moved on from that world. The truth is, those lessons were the foundation I needed all along. What I thought I was leaving behind turned out to be exactly where I was meant to return. It took me a decade to realize I was running in the wrong direction. Have you ever built success in one world, only to realize your future was waiting in another?

He lost money on that deal, but he would have lost many more millions if he had tried to build what he intended. Have you acquired anything you’d brag to friends at the bar about? What was it?

Most people are incredulous when they hear about this deal, but I sat down with the seller and asked how he was valuing his property and project, and then walked him through my numbers. He knew we were serious and could close, but I drew a firm line on what we’d walk away from.

With an average nightly rate of $300 and 70% occupancy, he wouldn’t have just been in the red, he’d have plunged into a financial sinkhole so deep he’d be negotiating with Hades for his construction loan.

The owner spent $3.3 million to acquire the land and then invested an additional $1.2 million in the entitlements. However, he lost control of the design process, and the plans he had developed would have cost him $7 million to build.

I purchased a 3,300 sq ft parcel with hotel entitlements on Fisherman’s Wharf for $ 1.2 million. You can hear the seals barking in the morning and see the cable car stop from the lobby. 🧵

@TheBigRuss77 It’s going to make block parties awkward for sure 😆

Let's hear your development horror stories, and we'll pour out a beer together for the lost sleep, gray hairs, and the hours your partner had to listen to your rants. I'll go first.

My wife and I have been living in our in-laws' ADU for two years, waiting to move in. Do you think Luther will bring over a welcome basket? My one-year-old son isn't old enough to toilet paper his house yet.

He has documented nearly every visit we've made, including weekends, and has even emailed the County with timestamps, attempting to prove violations that didn't exist.