Navigating Investor-Founder Dynamics

Brent Montgomery is the CEO of Wheelhouse Group, a family office where he creates entertainment content and a venture capital fund that invests in businesses to amplify brands around talent. Brent is a media producer and operator whose first hit was Pawn Stars at his first production company, Leftfield Pictures. He later oversaw a host of reality television hits, including HGTV's Fixer Upper, Netflix's Queer Eye, A&E's Duck Dynasty, and Bravo's The Real Housewives of New Jersey, while running ITV America after he sold Leftfield to ITV. Our conversation covers Brent's childhood entrepreneurial efforts, creation of Pawn Stars, vertically integrating and expanding Leftfield's business, and the sale to ITV. We turn to the flywheel behind Wheelhouse, monetizing talent and intellectual property across production, marketing, merchandising, and events, its partnering with leading investors, and a few investment examples along the way.

(3:16) Brent's background (8:22) Reality TV (9:47) Starting and operating a business (18:13) Investing in content at Wheelhouse (24:23) Team structure (26:59) Favorite types of investments (32:27) Insider's perspective (34:30) Thoughts on TikTok and Snapchat (36:35) Identifying talent and monetizing brands (39:56) Importance of investment arm (42:47) Trends in the world of content (45:52) Biggest risks (46:30) Closing questions