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.

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 breaches. Rob also discovers Thine — a $67 lifetime app that records everything your phone hears — right after Limitless got killed by Facebook. Then it's back to real estate: why the $1M–$3M price band is completely frozen, why the sub-$400K buyer is still moving, and why Chris thinks anyone doing a $900K flip in this market needs to seriously reconsider their numbers heading into 2027.

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: Rama Capital officially closed on the Palladian, the 20-unit deal that Pia first underwrote on January 28th — nine months from first look to close. And Rob's Salem flip is sitting on market, priced right but waiting on buyers, while the Tigard new build just got plans back from the architect and is heading for permit.

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 improving the sales process. But the biggest question comes when Rob says out loud what he’s been quietly thinking: with Rama Capital growing, flips running, and plenty already on his plate, should he even be building HireFlow right now? Parenting chaos, business systems, and the constant question every entrepreneur faces — what’s actually worth your time?

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 value-add no other buyer's agent in Portland is offering right now. And Rob's Salem flip is finally photo-ready: grass dead, contractor stalled, $4,800 in sod later, the house looks the way it should have looked two months ago. On market next week.

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 Clark — twenty minutes away, same-room living, communal bathrooms — and just now fully processing what sharing a room actually means. And Rama Capital is almost there: six LOIs out, a Delaware LLC, an operating agreement, and a close that's been five months in the making sitting right around the corner.