Built Between Bedtimes

In this episode, Dylan just spoke at the Portland REI meetup and broke down cost segregation for a room full of investors — including the guy who’s about to clear $150K tax-free on a triplex conversion and didn’t even know it. Then the news: Rama Capital submitted on a 75-unit Class A concrete-and-steel building in downtown Portland’s Goose Hollow neighborhood — originally traded at $20M, now offe...

In this episode, the guys kick off Halloween weekend — Dylan’s baby is a rat (technically a mouse), Chris is Batman, and Rob is flying solo for the first time since Max left for college. Then the big recap: Rama Capital’s investor meeting at the Palladian brought people in from Arizona and California, Gabe showed up with four bottles of champagne in a truck bed, and everyone ended up at the Malark...

In this episode, Chris got back from Santa Barbara to find his two-year-old completely unresponsive — turns out it was a febrile seizure, scary but okay, and now every dad in the room knows what to watch for. The guys make a friendly wager: will mortgage rates be over or under six percent by January 2026? Two say over, one says under, and the loser buys burgers at Joe’s. Then Dylan walks through t...

In this episode, Dylan’s baby has declared war on the bottle — five successful sessions in a row, one doula visit, and now it’s like they never happened. Chris introduces Jarvis, his Instinct AI assistant that already cleaned up 400 disorganized Asana deals, emailed brokers, sent LOIs, and sourced a custom-tailored suit from Hanoi in under a minute. Dylan breaks down GrokBot — unlimited agents, ea...

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 h...

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...

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 ev...

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 bac...

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 platform...

In this episode, Chris and Rob go deep on the All-In Podcast's conversation with Jensen Huang — NVIDIA founder, OSU alum, Aloha High grad — and what he said about AI doom and gloom, the Industrial Revolution, and why America needs to lead the charge. Then things get weird: AI models are apparently breaking containment, hacking companies, and leaving hidden files with instructions for future breach...

In this episode, Chris is back from three weeks of back-to-back travel — Caldera Springs, Dave Matthews at the Gorge where he and Sam first met, and a hundred-degree humidity bomb in Texas and Oklahoma — and somehow came home without a single argument. The secret? A house manager who shows up once a week, handles everything, and completely eliminated the pre-trip stress spiral. Then the big news:...

In this episode, Chris’s morning starts with a daycare call — Carter threw up on Tanner, which is somehow better than throwing up on a stranger’s kid. Rob follows it up with the story of Uncle Nick, a dead rat, and the shoe incident that started it all. Then the conversation turns to business. Dylan walks Rob through founder-led sales — from cold calls and CRM systems to using AI for coaching and...

In this episode, Rob drops Max off at Lewis and Clark on a Friday morning and comes home to an empty house for the first time in 18 years. She's already texting from the dunes. Chris breaks down the AI-powered underwriting tool Pia built that's pulling MLS listings every morning, running back-of-napkin numbers, and sending personalized deal reports to investor clients before they've had coffee — a...

In this episode, Dylan is flying solo tonight — Erica's at a Whitney show at Topaz Farms, grandma's coming over for baby training, and he's trying to figure out how to stop answering his Philippine VA's messages at 2 AM. The guys dig into one of the weirder new-parent negotiations: how much grandparent time is actually the right amount. Rob's daughter Max is days away from moving into Lewis and Cl...

In this episode, the guys smuggle a cantaloupe into a theater, Rob gets the boys into swimming lessons, and then things take a turn. Rob opens up about losing $110,000 in a gator lending scheme — transactional lending in Indiana that looked legit, had a spreadsheet, had a track record, had urgency built into every deal, and then disappeared to Mexico eight months in. Then comes the bonus story: th...

In this episode, Chris and Rob pick up where they left off — with Tim Ferriss, the Four-Hour Work Week, and what it actually looks like to stop being the bottleneck in your own business. Chris's wife is already on board with moving the family to a community in Costa Rica — think communal dinners, international neighbors, kids learning in the world instead of a classroom. The time zone math checks...

In this episode, Rob's daughter Max is 20 days from moving into Lewis and Clark — only child, never shared a room, roommate from California who's also in a band. It's happening fast. Then Rob gives a full rundown on how he's using Claude Cowork to manage three flips simultaneously — tracking vendor communications, job costing, and construction timelines across a master folder that cross-references...

In this episode, the guys do something they've been putting off — they talk about the failures. Chris opens up about his biggest: a 65-unit motel conversion in Reno, a $100K earnest money wire, a 60-day DD window he should have fought for, and a $6 million raise he never had a shot at pulling off alone. He missed the qualified opportunity zone deadline by one day, paid six figures in capital gains...

In this episode, Chris recaps the Portland REI Meetup with James Malarkey — grandson of the founder of Malarkey Roofing, which sold for $1.3 billion in 2022. James went from janitor to shareholder, and now he's partnering with his celebrity chef brother to buy the real estate under their restaurants — including a new steakhouse and seafood spot opening in the Pearl District. Then Rob closes the bo...

In this episode, Chris's chemo pal — the 10-year-old he's been visiting through the Children's Cancer Association — just had his port removed. He's done. Chris went over with Crumble cookies, got a tour of the port itself, and left with the kid asking if they can keep hanging out. Then Dylan gives a full baby product breakdown: the Snoo verdict, the bottle that was shooting milk like a fire hose,...

In this episode, Chris finally did it — a half Iron Man, trained entirely by Claude over six months starting from barely completing one lap. The swim was downstream and easy, the bike was brutal, and by the run his legs had completely given up. He shares what worked, what didn't, and why Claude's advice to skip weight training was probably right for someone with four to six hours a week. Then the...

In this episode, Rob's daughter finally has her permit — and Rob has no interest in letting her near the Tesla just yet. Chris shares the story of sneaking out at 12 years old in a full-size Suburban, driving through the West Hills, and ending up in a ditch with cops on the line to his parents at 3 AM on a school night. Then Dylan breaks down a hiring filter that most companies are sleeping on: sk...

In this episode, Dylan is solo with the baby for the first time and learns the hard way that blowouts don't wait for panel interviews to end. The Snoo gets a glowing review — and so does Facebook Marketplace, where you can apparently rent one at 2 AM with two-hour delivery. Chris is carb-loading for tomorrow's half Iron Man, trained entirely by Claude since February. Then the guys get into what Pi...

In this episode, Tanner turns five with real golf clubs and a hand-selected guest list — and Chris is fully locked in on becoming his caddy someday. Rob closes another Tigard auction deal, this time with the whole family waiting in the car while he checks for squatters before letting anyone in. Dylan is running on broken sleep but somehow shipping faster than ever — a Twilio-Basecamp-Google Calend...

In this episode, Dylan is officially a dad — and joins the show exactly seven days after his daughter arrived at exactly 4:00 PM. He shares what the induction looked like, what it felt like to walk out of the hospital with a person, and why the "don't shake your baby" video is apparently the only release form they give you. Then the conversation shifts to Rama Capital: the raise is oversubscribed,...