35:50

In this You Winning Life Podcast episode, host Jason Wasser, LMFT, interviews Josh McCallen, a serial entrepreneur, hotel developer, and GoBundance member. The conversation opens with an overview of the GoBundance mastermind community, its culture of radical accountability, and the $1 million net‑worth entry requirement. Josh shares his unconventional career path—from education and recruiting to European study‑abroad program management, to land‑development lending, to building a vertically integrated hospitality group that owns, designs, and operates boutique resorts. He explains the group’s operational model, including hiring a Disney Imagineer, creating a design‑construction arm, and scaling a management company. The bulk of the dialogue turns to practical wealth‑building tactics: house‑hacking, buying cash‑flowing assets, leveraging government‑backed mortgages, using self‑directed IRAs and private‑money loans, and intentionally taking cheap debt to hedge inflation. Josh emphasizes mindset shifts—seeing assets as income generators, embracing vulnerability in mastermind settings, and redefining financial freedom as expenses below non‑work income. He promotes his “Capital Hacking” podcast and the Accountable Equity platform as resources for aspiring investors. Throughout, the tone is conversational, enthusiastic, and occasionally blunt, with both hosts highlighting the importance of community, personal growth, and disciplined execution for entrepreneurial success.

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