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'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.
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.
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.
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.
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.
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.
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 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.