Built Between Bedtimes

Built Between Bedtimes

By BuiltBetweenBedtimesBusinessInvesting
Download on the App Store

Built Between Bedtimes episodes

  • Built Between Bedtimes – Episode 27: She Was Born at Exactly 4 PM, Rama Is Oversubscribed, and the Deadline That Made Everybody Pick Up the Phone

    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, the deal is closing, and it turns out all it took to unlock the final stretch was a hard deadline and a room full of people who finally picked up the phone. Plus — what the next deal pipeline looks like, why 400+ underwritten deals since January is just the beginning, and how track record changes everything for raise number two.

    32 min
  • Built Between Bedtimes – Episode 26: He Broke Into the House He Just Bought, Got Outbid by a Rookie, and Took His Kids Camping (It Did Not Go Well)

    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 asks about camping with toddlers and the answer is exactly what you'd expect: organized chaos, lost gear, and an overdue conversation about whether glamping counts.

    46 min
  • Built Between Bedtimes – Episode 25: Nobody Wanted to Move to McMinnville, the Rent-to-Own Buyer Who Thinks It's a Scam, and the CRM That Now Knows What People Want Before They Do

    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.

    44 min
  • Built Between Bedtimes – Episode 24: Six Days to Induction, a Hormone Tip That Changed Everything, and Why the Blinds Salesperson Completely Missed the Moment

    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.

    41 min
  • Built Between Bedtimes – Episode 23: The Oil Tank That Wasn't Decommissioned, the 150-Unit That Needs a Capital Partner, and Why Your Best Employee Might Also Be Your Worst Communicator

    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.

    48 min
  • Built Between Bedtimes – Episode 22: The Grad Night Pickup at 1:17 AM, the Refer-a-Friend Program That Pays $501, and the AI System That Replaced a $300/Month Tool

    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.

    37 min
  • Built Between Bedtimes – Episode 21: The Question That Broke His Identity, and the Rent-to-Own Model That Printed $100K More Per Deal

    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.

    55 min
  • Built Between Bedtimes – Episode 20: His Last Birthday Without a Kid, Claude Is Training Him for a Half Ironman, and the Japanese Word That Might Change How You Think About a Whole Year

    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.

    34 min
  • Built Between Bedtimes – Episode 19: The $20K That Almost Went Hard, the Doctor Who Almost Lost $650K, and Thirty-Two Offers on a Dump in Lake Oswego

    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.

    48 min
  • Built Between Bedtimes – Episode 18: The 10-Year-Old Who Made Him Rethink Everything, and the Closer's Club Nobody Talks About

    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.

    48 min

About Built Between Bedtimes

From the publisher's feed

Built Between Bedtimes is a podcast for ambitious dads building businesses, families, and meaningful lives — often after the kids are asleep.