The BuiltBetweenBedtimes’s Podcast

In this episode, Chris and Rob go two-on-two while Dylan sound bathes in Sedona — and cover more ground than expected. Rob finally cracks the code on getting his 17-year-old to take her driver's permit test after a forgotten PIN and a stranded Saturday do what two years of asking couldn't. Then it's all business: Chris gives a live update on the 20-unit deal with earnest money 30 days from going hard, Rob breaks down the AI general manager bot he built to run his operations while he sleeps, and Chris shares how he's using AI and his VA Pia to turn a monthly meetup into a warm lead machine. The takeaway? Partner with people who have experience, use AI to find your bottlenecks, and leverage VAs to get out of your own way.

In this episode, Dylan feels his baby girl kick for the first time — and responds by reading her a book through the belly. It's baby season all around: a partner's wife is being induced mid-recording, and Rob's sales team is quietly celebrating a teammate's paternity leave. Then things get interesting. Rob pulls back the curtain on the foreclosure auction world — courthouse steps, trustee sale lists, insider networks, and the Salem property he snagged for literally one dollar over the opening bid with nobody else in the room. Plus, why catching a seller before auction might be the single best deal structure in real estate, and why the guys think Oregon's trustee cartel deserves a Vice documentary.

 In this episode, Rob's Sub2 meetup is about to be standing room only — 150 people registered for an 80-person space — and the guys break down why Pace Morby's Creative Nation Tour turned a real estate event into a room where actual deals were closing in the crowd. Chris just got back from Squad Up Summit in Denver, where it snowed after a 75-degree dinner at Casa Bonita. Then Dylan drops some numbers that'll make you rethink everything — a 61-property investor who's been leaving hundreds of thousands on the table every year, a California hotel deal with $1.4M in tax savings, and a deep dive into why comparing real estate to the S&P 500 is the wrong math entirely.  

In this episode, Dylan finally makes it back from Hawaii — just barely — after a once-in-15-years storm dumped two feet of rain on Maui, stranded flights, and turned a family vacation into a survival mode situation with twin four-year-olds and toilet paper earplugs. Chris recaps a Legoland daddy-daughter trip where they arrived late, left late, and somehow squeezed in seven rides. Then the conversation goes deep on AI — how Rama Capital used Claude to redline a PSA instead of paying $4–5K in legal fees, why the guys are rethinking how they hire, and why the most dangerous thing you can do right now is ignore what AI is doing to your industry.

In this episode, Rob's daughter brings up a memory he wishes she'd forgotten — the birthday where a deal took priority over being present — and the honest conversation that followed. Then Chris's son Tanner finally gets his cast off after four weeks, revealing everything you never wanted to know about what happens inside a cast on a four-year-old. Plus — the guys get into the real cost of doing everything yourself as an entrepreneur, why handing off to a VA might be the highest-ROI decision you're not making, and how Hireflow VA was born from a meetup conversation, a three-year assistant relationship, and a lot of people who kept asking "can I just use yours?"

In this episode, Dylan's in Maui and Chris and Rob are holding it down — talking about Rob's daughter's first job at Pizza Hut, a canceled order, a bathroom breakdown, and what it actually means to care about doing good work. Then the conversation shifts to the real cost of buying multifamily that looks great on paper: Chris tours two properties and discovers that spreadsheets don't tell you about 40% tenant turnover, units that feel like closets, or homeless camps cropped out of listing photos. Plus — why Rama Capital is pumping the brakes on new LOIs, and what $20–30K in due diligence costs actually at risk per deal.

In this episode, Rob is counting down the days until his daughter graduates — and the unexpected calm that comes with it. Dylan's baby is making herself known at 20 weeks, and the guys get into the strange, emotional math of how much time you actually get with your kids before they stop thinking you're cool. Then the conversation pivots hard into macro: Portland's cratering multifamily permit numbers, what SDC waivers actually mean for developers, why institutional money hasn't shown up yet — and why that might be exactly the window Rama Capital is betting on.

In this episode, Chris, Rob, and Dylan get into the messy, real, unscripted side of building — as dads and as investors. Chris shares how a taekwondo class next door to a Pilates studio might be the parenting hack nobody talks about, and the guys go deep on the age-old tension between engineering your kid's future versus just shepherding who they already are. Then the conversation shifts to Rama Capital's first deal, still working through the purchase and sale agreement, and what it actually takes to pull off a multifamily raise — from building the investor deck to finding a guarantor who can backstop the debt. It's not closed yet. But it's getting real.

In this episode, Chris sits down with Matt King — CEO of GoBundance, family office operator for David Osborne, and a man who built everything he has by chasing proximity to greatness before he could afford to. Matt shares the locker room moment that rewired how he thinks about wealth, why service is the Trojan horse to knowledge, and what it really means to give yourself permission to pursue the life you want. Then he reveals the most audacious thing he's ever attempted: biking from the Mexican border to Canada — 2,000 miles, 12 days, 150 miles a day — while giving away $1 million to families along the route in real time. No fund. No someday. Just showing up mile by mile.