Built Between Bedtimes

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: the second operator who cussed him out on a group thread for asking too many questions, banned him from future deals, and then — two months later — got investigated for something significantly darker. The lesson? Vet the person, not the spreadsheet. Background checks exist for a reason.

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 out: Portland is one hour ahead. The mosquito situation is still unresolved. Rob breaks down the practical steps he's taking from the book right now: cutting email to twice a day, handing off responses, and designing the business so it runs while he sleeps. The goal isn't retirement. It's optionality. And Chris is being held publicly accountable to picking a date.

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 itself. He also admits to handing a contractor his credit card for Lowe's runs, which nobody around him thought was a good idea. And the biggest insight from his book stack this year: he's been talking too much in team meetings, not listening enough, and the one time he reversed that — asking questions and staying quiet — his team surfaced problems he didn't even know existed.

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, and walked away with $25K in sunk costs and a lesson that eventually led him to Dylan and the Rama Capital model. Dylan follows with his own: leaving a six-figure tech career, starting Seneca with no salary,putting a strain on his marriage, and not paying himself for over a year while the business quietly scaled to $45K a month. Two very different failure stories. Both completely worth hearing.

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 book on McMinnville: a fail flip that became a rent-to-own deal, a $25K option fee from the most committed buyer in the funnel, and a system that's now fully built and ready to scale. The property didn't make anyone rich, but the playbook it produced might.

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, the grandma hack that eliminated the 10-minute warm-up cry, and the bottle warmer that doesn't require descaling. And then the show goes deep on one of the most overlooked tax plays in real estate — the $500K capital gains exclusion for married couples on a primary residence, how live-in flips work, and the actual math on what you're giving up if you hold or sell at the wrong time.

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 conversation gets real: Rob's been building sales systems with AI, but keeps running into the same wall — chasing KPIs instead of the behaviors that create them. Dylan breaks down how to use data to surface problems without making your team feel like they're failing. And Chris admits out loud what a lot of entrepreneurs won't — he might be building too many bridges at once.

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: skip the résumé wall, get a two-minute video, then have Claude watch it, score it against your criteria, and cut your funnel to only the applicants worth talking to. And Chris shows off what Pia's been building — a morning email that underwrites 30 investor deals overnight and lands in your inbox before you've had your coffee.

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 Pia built this week: an automated workflow that pulls investor buy boxes into the CRM, searches the MLS every morning, underwrites every result, finds the top three deals, and sends a personalized email at 9 AM — something no other agent in the market is doing.

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 Calendar bot that confirms jobs, reads calendars, escalates weird questions, and already exists on his Mac Mini. He's just waiting to roll it out so Gabby still has something to do in the morning. Then the guys talk about what AI actually is for small business visionaries right now: not a tool, but an integrator — and how a verbal brain dump on ten past jobs might be the fastest way to train your next estimator.