Built Between Bedtimes

In this episode, the guys set aside the business talk for something heavier. A school shooting in Bend hits close to home — all three of them are dads, all three of them drove home differently that night. They talk about what it’s like raising kids in a world where shooter drills are normal, why the conversation always gets stuck, and what one father with two daughters at that school did when he heard the shots. There are no easy answers here. But there’s a real conversation — about mental illness, about access, about marketing, about what it means to send your kid somewhere that should be the safest place in the world. Hug your kids tonight.

In this episode, Dylan finally closes the book on a lawsuit that’s been running for a year and a half — a tenant who stopped paying rent, fell on the stairs, fractured a vertebrae, and came after him for $700,000. The stairs were off code by one millimeter. One. The property was in his personal name, not an LLC. The case landed in Multnomah County — the worst possible venue for a landlord. And the mediator’s opening pitch was straight out of a timeshare playbook. Meanwhile Chris survived three weeks straight of back-to-back family travel, did an annual deep clean at the Rhododendron short term rental (the grill situation was not pretty), and learned firsthand why you should never outfit a vacation rental with anything you actually care about.

In this episode, Dylan comes in hot with Seneca’s biggest month in company history — and a rep who closed over six figures in a single month and immediately set her sights on five. He breaks down why firing their ad agency was the best marketing decision they made, how 14x-ing conversions on 30% more spend actually happened, and why most small businesses are handing money to agencies that don’t even connect revenue to ad spend. Then it’s a masterclass on SEO vs. GEO — how AI search engines like Claude and ChatGPT decide who to surface, why a Wikipedia backlink used to print results, and why the content engine you build today is the one that gets you found tomorrow. Plus: Dylan coins “caveman parenting,” and Chris just wants more leads.

In this episode, Chris casually runs into his neighbor Damian Lillard at the kids’ swim class and seriously considers handing Dame one of his Blazers schedule real estate magnets. Then the guys get into Rama Capital — the upcoming Palladian investor event, their plan to overcommunicate with investors, and the hunt for their next 30–80 unit apartment deal across Oregon and Washington. Then it’s back to the reason this podcast is called Built Between Bedtimes: Dylan opens up about the tough early months of being a new dad, Chris survives a 20-minute parking lot meltdown over a pair of shoes, and the guys finish by playing the grateful game and sharing what keeps everything in perspective when parenting gets hard.

In this episode, Dylan is back from the Mandane Conference, where maroon blazers, vocal improv, Pokémon card economics, and a presentation on Rama Capital somehow all make sense together. Chris then tells the story of hitting a hole-in-one at Shortland — on the same round his buddy hit one too. Then things turn to AI: Dylan has been testing Instinct, an AI agent that can log into business platforms, update payroll, onboard employees, and handle tasks from a simple text message. Finally, Rob breaks down a property management nightmare that turned a clogged toilet into more than $5,000 in invoices — and why every rental property owner should take another look at the repair authorization language in their management agreement.