Built Between Bedtimes
Built Between Bedtimes is a podcast for ambitious dads building businesses, families, and meaningful lives — often after the kids are asleep.
Hosted by real estate entrepreneurs and fathers in the trenches, this show dives into the real conversations behind entrepreneurship, fatherhood, marriage, and personal growth.
We talk about:
- Building real estate portfolios
- Balancing business and family life
- The wins, struggles, and lessons of fatherhood
- What it takes to create freedom and legacy
These are the conversations that happen after bedtime — when the real work begins.
If you're a dad trying to build something meaningful while raising a family, this podcast is for you.
Episodes

Aug 4, 2026
Aug 4, 2026
43 min
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 buyer list that keeps people informed without annoying them. Then the guys get into what's broken in most small business comp structures — why a salaried salesperson is almost always the wrong move, how profit-first incentive design changes everything, and why your QuickBooks setup might be the silent bottleneck you've been ignoring.

Jul 31, 2026
Jul 31, 2026
40 min
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 — how he outbid the field by comping the deal better than the agents did. Then Dylan closes with something that's genuinely baffling: a blinds salesperson who showed up with swatches when ChatGPT could have designed six custom room mockups on the spot, and still lost the sale.

Jul 30, 2026
Jul 30, 2026
47 min
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 baby. The guys also dig into something every business owner deals with but rarely talks about — when your best performer is invisible to everyone around them, and what it actually takes to lead someone without making them feel like a number.

Jul 29, 2026
Jul 29, 2026
36 min
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 business: Dylan launches a $501 refer-a-friend program at Seneca to beat the competitors offering exactly $500 — and Chris breaks down how he's using AI to automate his entire review funnel, replace a $300/month SaaS tool, and build a trust engine for Hireflow VA from the ground up.

Jul 28, 2026
Jul 28, 2026
54 min
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 traditional sale. Then Chris comes back from GoBundance with a question that's still rattling around in his head: if you won the lottery tomorrow, would you still be doing this? And whether the answer to that question should change how you're building your vision right now.

Jul 23, 2026
Jul 23, 2026
33 min
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, got vulnerable, and did breathwork — and introduces the concept of the Masogi: one defining event per year that makes the whole year memorable. Chris is six weeks out from a half Ironman he's training for using Claude as his coach. His buddy doing a full one is logging 15–20 hours a week. Chris is doing four to six. The gap is significant.

Jul 17, 2026
Jul 17, 2026
47 min
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 look like on a deal that size. Plus: Chris submits offers on two properties and gets smoked — nine offers the first day, thirty-two on the next — and breaks down what's really happening in the Portland market right now, why rates jumping three-quarters of a point hasn't cooled things off yet, and how Pia just replaced a $30/month software subscription by building something better in an afternoon.

Jul 16, 2026
Jul 16, 2026
47 min
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 final days before becoming a dad. Rob's daughter turns 18. Then the conversation shifts: Chris gets invited to his real estate team's top-five Closers Club event at a brand new winery with caves, a speakeasy, and 25-year-old vines — and the high-level conversation about inbound leads, AI leverage, and VAs that nobody was having at the regular training meetings.

Jul 9, 2026
Jul 9, 2026
32 min
In this episode, Rob is deep in the AI rabbit hole — and it's getting expensive. After burning through his entire monthly Claude allotment by Monday building three bots simultaneously, he racked up $500 in API overage in two days doing "minimal" work. His solution? Order a second Mac Mini, run it headless under his desk, and spin up a second $200/month Max plan. Chris and Rob get into why the businesses actually winning with AI aren't cutting people — they're amplifying them. Then it's a preview of the next Portland REI Meetup, a sneak peek at guest Arie Van Gemeren and his 300-400 unit pre-war portfolio, and a rabbit hole on whether MLS data could be the final unlock for a truly automated underwriting tool.

Jul 7, 2026
Jul 7, 2026
38 min
In this episode, Chris and Rob swap Mother's Day stories — one involving a perfect embroidered sweatshirt, the other a broken play that turned into cold coffee, canceled reservations, and a lesson in never giving your wife too many options. Then the conversation pivots to deals: Rama Capital's 20-unit is heading into final negotiations with a failed roof, a shot water heater, and original 1928 galvanized plumbing pushing the case for a price reduction — while a brand new 150-unit opportunity lands out of nowhere with return metrics that actually work. Chris breaks down why scaling up changes everything from property management fees to your credibility as an operator, and why getting that first big close might be the only thing standing between Rama Capital and any deal they want.







