Casey Woodard is a Buffalo-born, Austin-based entrepreneur and investor. With a background in reselling, he’s scaled Divine which is now the largest paid reselling community in the world. Alongside that, he’s immersing himself into the world of paid online community M&A. He’s a silent partner in some of the most successful paid communities around. Most recently, he became a general partner in Other Health, a VC fund focused on innovations in health and wearables.

Listen to the full interview with Casey on Youtube, Spotify, or Apple Podcasts.

Casey’s sweet spot is turning fragmented niches into monetizable communities. He only takes on projects that offer a foolproof opportunity for him to have notable upside relative to the time and/or money he invests. He sells real leverage (tools, systems, cash, and distribution) to people who already know the basics. For you sellers reading, don’t just target anyone with an open wallet. Target operators with unique pain. They pay more.

Casey’s foundational skill in selling came from flipping. Beginning with $5 shirts at a thrift store, to full estate sale liquidations. That repeated exposure to margin made him fluent in identifying value and understanding other point of views within a deal. Master the art of finding the spread in a deal, then position yourself, your offer, or your product along a midpoint that’s advantageous to you.

It’s no surprise that Casey is now in the business of buying other communities to either run behind the scenes or merge with Divine. Becoming your own testimonial is the ultimate way to showcase the results you can deliver to potential clients. By being front-facing and with your own testimonial, or having a party close to you become one, the inherent trust within any transaction skyrockets.

1. Learn to spot and capitalize on overlooked opportunities.

2. Organize communities where transactions happen by default.

3. Initiate deals by creating value before you try to sell.

4. Negotiate better. Know your numbers.