Built Between Bedtimes

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,...

In this episode, Rob picks up a Tigard flip at the foreclosure auction for $302K — by out-comping the agents who priced it wrong — then goes straight from the courthouse steps to the backyard window to get inside. Chris is still chemo-pal visits, a meetup where he tried to close a deal in the room, and a conversation about why Portland condos are rarely a good long-term investment. Then someone as...

In this episode, Rob's McMinnville property open house has a motivated seller, suspicious buyers, and a Kool-Aid Man moment where a couple threw the door open before he could get to it. He breaks down exactly how to run a Facebook Marketplace rent-to-own campaign without triggering a ban, why the only qualifications that matter are $7,500 and 2.5x rent, and how Claude helped him build a segmented...

In this episode, Dylan is six days out from induction and spending every night until midnight clearing his bottlenecks before the baby arrives — including becoming his own marketing department. Chris shares the hormone tip that turned his wife's postpartum experience from brutal to night-and-day different, and strongly encourages Dylan to look into it. Rob runs down his foreclosure auction process...

In this episode, dads — because that's officially what we're calling you — the guys open with something every new parent knows: the moment you realize you're suddenly more focused, more motivated, and way more stressed about money. Then Rama Capital's 20-unit deal gets down to the wire, with a buried oil tank nobody removed, an addendum being signed that day, and a closing race against Dylan's bab...

In this episode, the guys celebrate over freshly made margaritas on a Friday afternoon. Rob's daughter graduates high school at PSU's packed auditorium — and calls him at 1:17 AM from Conestoga Water Park to pick her up, activating the standing family pact nobody ever actually expects to use. Dylan recaps the Wolfcella music festival and where being a parent starts to hit different. Then it's busi...

In this episode, Rob runs an open house for a McMinnville property that's been sitting for five months — and breaks down the rent-to-own model from top to bottom: how to price the option fee, why Facebook Marketplace beats everything else, the Nerdy Panda bot running 24/7 on a Mac Mini to handle three hundred inbox messages, and how investors are walking away with $60–100K more per deal than a tra...

In this episode, Dylan celebrates his last birthday as a non-parent — two weeks out from a potential induction date, baby formula questions, and a car seat installation class he's not sure he needed. Rob gets banned from Wolfcella, shows up anyway, and brings the whole family without telling his daughter. Then Chris comes back from a GoBundance event in Chicago where thirty people got emotional, g...

In this episode, Rama Capital's earnest money nearly goes non-refundable — until Chris catches a contract clause that changes everything. With one week left, they're still chasing a $50K credit, a clean oil tank scan, and the last of their raise. Then Rob tells the story of a doctor at a conference who showed up with $700K and almost handed it over for 5% equity — and what the actual math should l...

In this episode, Chris shares the moment that stopped him cold — sitting with a 10-year-old boy going through chemo, playing Battleship, building Legos, and getting a text the next day that broke his heart in the best possible way. He opens up about his six years on the Children's Cancer Association board and why he's convinced he's getting more out of this than he's giving. Dylan counts down the...