😎 $14M at 26 through online communities, cold email alpha, and tax bracket jumps

SELLER’S SECRETS

Who is Casey Woodard and what is he up to?

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 Come Up (in 10 bullet points)

• Sold chocolate bars door-to-door at age 7 for school fundraisers

• Started flipping at 15, found his niche in music equipment.

• Graduated college at 19, earned a master’s in finance by 21.

• Worked 2-3 jobs through school, including tutoring and car sales.

• Consistently took on larger and larger reselling projects.

• Moved to Austin in 2022 to be around more people like him.

• Merged into Divine, scaled to 5,000 paid users and #23 on WHOP.

• Started acquiring under-optimized online communities for equity and cash flow.

• Partnered on new VC fund focused on health and wearables with his friends.

Casey’s Sales Alpha and Best Practices

1. Sell to Niche Operators Who Want Tools, Not Theory.

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.

2. Sell Better by Understanding The Spread of Every Deal.

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.

3. The Closer the Testimonial, the Sweeter the Deal.

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.

Action Items: Take inspiration from Casey (implement these)

1. Learn to spot and capitalize on overlooked opportunities.

• Learn arbitrage with products/services, then apply to people.

• Analyze where underserved audiences spend or circulate money.

• Build systems that make those transactions faster or cheaper.

• Monetize with tools, content, or partnerships native to that niche.

2. Organize communities where transactions happen by default.

• Identify niches already active (resellers, hobbyists, tinkerers, etc.)

• Offer low-friction entry points with high engagement payoffs

• Build in tools, resources, or access people want or need.

• Make it frictionless for people to become invested.

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

• Give your prospect something useful upfront (insight, audit, data).

• “Build a hub” like Casey did. Community, email list, or exclusive group.

• Use free value to warm up cold leads.

• People reciprocate actions. Helping them first helps you.

4. Negotiate better. Know your numbers.

• Understand market value relative to your buyer’s needs

• Know your costs, margin, and minimum sellable price point

• Use simple, direct language when making your offer

• Stay calm and walk away if the deal doesn’t hit the needed margin