A $25M personal income isn't all spendable cash. Matt Paulsen breaks it down: ~$8M to federal taxes, half of the remainder goes directly into trusts for generational wealth, and ~$2M to charity. This leaves about $5M for personal living expenses and investments.
Matt Paulsen views his significant charitable giving as his turn to step up as a community leader, following the example of predecessors in his town. He explicitly states that it's not a financial decision, noting that for every dollar he gives, he only gets 37 cents back in tax benefits.
Matt Paulsen bought a private jet not for pure luxury, but because limited flights in Sioux Falls made chartering inefficient. He leveraged 100% bonus depreciation to offset the cost and charters the plane to operate near break-even, making it a practical business asset in a small market.
Matt Paulsen's decision to bootstrap his company wasn't a strategic philosophical choice; it was a practical necessity. Starting his business in a small college town in South Dakota meant there was no venture capital ecosystem to tap into. The lack of options forced a path of self-sufficiency.
Despite his immense wealth, Matt Paulsen has no plans to sell his company. He equates the business to one of his own children, driven by a deep love for operating it rather than a financial exit strategy. This challenges the common "build-to-sell" mentality prevalent in entrepreneurship.
To keep his children grounded despite his wealth, Matt Paulsen intentionally maintains a relatively normal lifestyle for them. His strategy involves living in a modest house (bought for $400k) and sending them to public school, ensuring their daily lives mirror those of their peers to prevent entitlement.
Matt Paulsen's large real estate portfolio wasn't the result of a long-term asset allocation plan. Instead, he and his partner identified a unique, time-sensitive opportunity during the pandemic with panicked sellers and 3% interest rates. They bought aggressively, viewing it as a generational moment to acquire assets cheaply.
After making numerous small angel investments, Matt Paulsen found the administrative complexity of managing over 100 K-1 tax forms overwhelming. To simplify his life, he now only writes checks of $500,000 or more, filtering out opportunities that aren't worth the mental overhead.
Despite his success, Matt Paulsen maintains a rigid boundary to protect his family life. Because his daughter requires significant attention, he systematically declines 2-3 evening event invitations per week, stating he'll be home with his kids, prioritizing being present during their childhood over networking.