A Peak into Strategy - Good or Bad Idea? | Lazy Leverage #68

26 snips

Aug 9, 2025

Jon and Peter brainstorm a unique business concept: purchasing luxury vacation properties to provide members with steep discounts while leveraging tax benefits. They debate the viability of this idea, weighing the potential operational challenges against the allure of premium offerings. The discussion touches on balancing creativity with structured strategy and the importance of effective property management. They also delve into the complexities of short-term rentals in regulated areas and the benefits of a membership model for family travelers.

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INSIGHT

Volume + Vetting Finds Real Ideas

Jon uses volume ideation: he generates many ideas to find the few winners.
He refines them through repeated vetting and feedback until they survive the filter.

ANECDOTE

Maple Syrup Metaphor For Refinement

Peter likens Jon's process to maple syrup: initial ideas are watery and need distillation.
He says testing and refining boil off the bad until real value remains.

INSIGHT

How Bonus Depreciation Creates Year-One Deductions

Peter explains cost segregation and bonus depreciation create a large paper loss in year one.
He shows this can legally offset earned income for high earners.

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Jon and Peter dive into one of those ideas that sounds crazy at first but might actually be brilliant: buying luxury vacation properties as a business expense that doubles as a killer member benefit. Jon's been noodling on this concept for months, and it's finally survived his brutal idea-filtering process (which involves annoying everyone from his CFO to random Twitter buddies until the bad ideas die off).

Here's the pitch: Sagan would purchase several properties—think ski chalets, beach houses, maybe something in Mexico—and offer them to members at 50-75% below Airbnb rates. The kicker? Thanks to bonus depreciation and some creative tax structuring, the whole thing could essentially pay for itself while adding a premium benefit that helps with member retention.

Peter initially pushes back hard on the operational nightmare this could become. Nobody wants to field calls about broken ice makers or dirty towels. But as they hash it out, the vision gets clearer: professional property management with multiple layers between Jon and any actual guest issues, properties strategically located for both vacations and corporate retreats, and a focus on serving their high-trust member base rather than random Airbnb guests.

Successful entrepreneurs develop strategy not through formal PowerPoints and weighted decision matrices, but through relentless debate, pattern recognition, and asking "will this actually f***ing work?" over and over until the answer becomes clear.

Key Topics:
(01:49) The Art of Business Ideation: Volume Shooting vs. Analysis Paralysis
(11:56) Introducing the Vacation Property Concept for Sagan Members
(15:29) Bonus Depreciation and Tax Strategy Explained
(21:29) Solving the Property Management Problem Before It Starts
(27:51) Facilitating Global Team Meetups at Member Properties
(31:11) Location Strategy: East Coast, West Coast, International
(34:06) Building the Management Structure and Avoiding Operational Headaches