The 3 Questions To Ask Before You Exit episode artwork

EPISODE · Jul 21, 2026 · 11 MIN

The 3 Questions To Ask Before You Exit

from Own The Exit · host Caleb Edwards and Aaron Leatherdale

If you have a major liquidity event on the horizon — whether it’s selling a business, exiting a real estate portfolio, or preparing for a large capital event — what you do next matters more than most people realize.In this solo episode of Own The Exit, Aaron breaks down the three critical questions every entrepreneur and investor needs to answer before deploying capital after an exit. From tax strategy and investment timelines to understanding your competitive advantage as an investor, this episode gives a practical framework for navigating wealth transitions with confidence.TAKEAWAYSThe 3 essential questions to ask before deploying capitalWhy liquidity events create both opportunity and riskHow business owners should think about replacing income after an exitThe importance of tax planning before a sale closesWhy investing in familiar asset classes reduces riskHow passive real estate investing can replace active management headachesReal-world examples of investors transitioning into passive incomeRESOURCES MENTIONEDOak IQ InvestmentsFOLLOWS⁠⁠Oak IQ Investments⁠⁠⁠Own The Exit⁠⁠Aaron Investing⁠CHAPTERS00:00 The 3 Questions Every Seller Must Answer01:10 Question #102:05 Question #2 03:41 Question #3 05:57 Real Estate Investor Case Study: Jeff07:39 Multifamily Investor Case Study: Fred09:04 Business Exit Case Study11:00 Planning Your Next Move After A Liquidity EventKEYWORDSliquidity event, business exit strategy, passive real estate investing, 1031 exchange, wealth preservation, entrepreneur investing, passive income strategies, business sale planning, real estate portfolio exit, accredited investor strategies, alternative investments, multifamily investing, tax efficient investing, capital deployment, real estate syndication, investment diversification, generational wealth, financial freedom, investment strategy, private investments, business owner wealth planning, passive cash flowWANT TO LEARN MORE?Join us on ⁠LinkedIn⁠, dive into our enriching content on ⁠YouTube⁠, and explore ⁠our website⁠ to unravel how to secure your future through intelligent passive investments!If you enjoyed the show, please LEAVE A 5-STAR REVIEW and SHARE this episode with someone preparing for a major financial transition. Listen to all episodes on ⁠Spotify⁠, ⁠Apple Podcasts⁠, or any preferred podcast platform!

Episode metadata supplied by the publisher feed · Published Jul 21, 2026

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The 3 Questions To Ask Before You Exit

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