Built Between Bedtimes
Built Between Bedtimes
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Built Between Bedtimes – Episode 32: The 10-Year-Old Got His Port Out, the Bottle Warmer That Changes Everything, and the $500K Tax Exemption Nobody Talks About

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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.

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Built Between Bedtimes – Episode 34: He Lost $25K, Missed the Deadline by One Day, and Almost Took Down a 65-Unit Alone — Here's What He Learned

Built Between Bedtimes – Episode 34: He Lost $25K, Missed the Deadline by One Day, and Almost Took Down a 65-Unit Alone — Here's What He Learned

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 a…
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Built Between Bedtimes – Episode 36: Costa Rica, a Four-Hour Work Week, and the Plan to Disappear for a Quarter

Built Between Bedtimes – Episode 36: Costa Rica, a Four-Hour Work Week, and the Plan to Disappear for a Quarter

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, i…
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Built Between Bedtimes – Episode 35: Max Is Moving Out in 20 Days, Rob Gave His Contractor a Credit Card, and the Leadership Mistake That Was Costing Him More Than He Knew

Built Between Bedtimes – Episode 35: Max Is Moving Out in 20 Days, Rob Gave His Contractor a Credit Card, and the Leadership Mistake That Was Costing Him More Than He Knew

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…
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Built Between Bedtimes – Episode 33: The Malarkey Family Sold for $1.3 Billion, Rob Finally Moved the McMinnville Property, and Why the Fail Flip Became the Best System-Builder

Built Between Bedtimes – Episode 33: The Malarkey Family Sold for $1.3 Billion, Rob Finally Moved the McMinnville Property, and Why the Fail Flip Became the Best System-Builder

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 restaurant…
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