3. Estimated Net Worth
His net worth has been estimated at around $300 million by various sources. O’Leary is involved in a diverse array of enterprises, including O’Leary Fine Wines, O’Leary Mortgages, and the numerous companies in which he has invested venture capital. His most successful Shark Tank investment to date has been Talbott Teas, a joint venture with Daymond John that was eventually acquired by Jamba Juice for an undisclosed amount. In 2008, he partnered with Connor O’Brien to open O’Leary Funds. The company currently offers 13 different mutual funds and four closed-end funds spread across a variety of categories, such as equity income, fixed income, and global growth.