Raising Private Money with Jay Conner Private Money Success: Tim Benskin’s Step-by-Step Guide to Raising $940,000
If you’ve ever wondered how to raise serious private money for real estate—even if you’re starting from scratch—you’ll find real inspiration and specific tactics in the success story of Tim Benskin.
On a recent episode of the Raising Private Money podcast, host Jay Conner sat down with Tim to unpack his journey. Tim, a member of Jay’s mastermind group, has already raised $940,000 in private money in less than a year, funding twelve deals since October 2023—all without using a single dollar of his cash.
Here are the game-changing takeaways from Tim’s experience and why they’re so actionable for anyone wanting to break into raising private money.
- Private Money Isn’t About Selling—It’s About Teaching
One of the standout points in Tim’s story is his approach to attracting private lenders. He doesn’t pitch or “sell” anyone. Instead, he takes pride in wearing a cap that says “Private Money Teacher,” because that’s exactly what he does—educates people about the opportunity for them to earn better returns on their money.
Most of Tim’s lenders had never even heard of private lending before. Some had their money sitting in savings accounts, earning modest interest, or in IRAs, but had no idea they could use those funds to lend on real estate. By patiently explaining the process and benefits, Tim creates trust and interest. The conversation is about helping, not selling, and that servant’s heart approach makes all the difference.
- Confidence Comes from Preparation
Tim and his wife Robin started by joining Jay Connor’s mastermind and immersing themselves in learning. They spent the first three months simply absorbing everything about raising private money. This education gave Tim the confidence to talk to potential lenders—with zero desperation or uncertainty.
A key lesson Tim shares: line up the money before you line up the deals. Having committed funds in advance lets you make more offers and move decisively, which is impossible if you’re scrambling for financing after finding a property. For Tim, this was the difference between sitting on the sidelines and closing twelve deals in under a year.
- Your Network Is Full of Potential Lenders (Even if They Don’t Know It Yet)
Tim’s first lender was a longtime friend and fellow church member. The introduction came through casual conversation, followed by inviting him to a webinar about private lending. The friend happened to already have a self-directed IRA—something Tim learned only by asking questions and listening.
The lesson? Don’t pre-judge or “pre-qualify” people based on assumptions. Many in your social and professional circles could become private lenders if you simply share what you’re doing and offer to teach them more. Tim’s story started with a breakfast meeting and a willingness to discuss his business openly—no hard sell necessary.
- Deal Structure: Win-Win for Both Sides
For his first deal, Tim purchased a distressed property in Rockford, Illinois, for $125,000, putting in $80,000 for renovations. The home’s value after improvements was around $250,000–260,000. Rather than flipping the home immediately, Tim found renters—again, through connections from his community—who take excellent care of the property.
His private lender is more than happy with solid returns that far exceed CD rates, all secured with real estate. The lender has earned nearly $20,000 in interest so far, with no roller-coaster stock market risks and no hidden fees.
- Growth Through Education and Consistency
Tim readily admits he started as an introvert, not a natural networker. But by consistently sharing what he knows, holding “lunch and learn” events, and always leading with education, both his confidence and his pool of lenders have grown. He emphasizes the tortoise-wins-the-race mentality—con