Acquisition Capital: Using Retirement Accounts to Invest in Businesses - John Bowens
What's Your Deal? | Buying Businesses, Business Acquisitions, Investing & Exit Strategies
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Show Notes
In this episode of What's Your Deal?, Matt sits down with John Bowens, Director of Head of Education & Investor Success at Equity Trust, to break down one of the most overlooked wealth tools for entrepreneurs and investors: self-directed retirement accounts.
John explains what "self-directed" actually means, why most retirement money stays locked in mutual funds by default, and how investors can use IRAs, 401(k)s (and even HSAs) to invest in real estate, private lending, private equity, pre-IPO stock, cryptocurrency, and precious metals—all while keeping the tax advantages of retirement accounts.
They also dive into the ROBS (Rollover for Business Startups) structure and how some buyers use retirement funds to acquire a business without triggering taxes and penalties—plus the common mistakes and prohibited transaction rules that can trip people up if they don't understand the guardrails.
If you've ever wondered how to put your retirement money to work in the assets you actually understand—this episode is your roadmap.
Timestamps:
1:30 – What Equity Trust does + what "self-directed" means
3:40 – John's background and how he got into this industry
6:40 – Why investors choose self-directed accounts (diversification + taxes)
9:20 – Clearing up a misconception: contributing vs investing
12:15 – Liquidity: short-term vs long-term alternative investing
16:50 – Matching strategy to age, goals, and skill set
20:20 – ROBS overview: using retirement funds to buy a business
29:50 – Costs + when it does/doesn't make sense financially
38:45 – Common mistakes + prohibited transactions
41:30 – John's "hand up" story + mentors
Resources & Links
Connect with John:
Website: https://www.trustetc.com
Instagram: https://www.instagram.com/johnbowenscisp
LinkedIn: https://www.linkedin.com/in/john-bowens/
Connect with Matt:
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