The biggest national homebuilders in the Southeast have overbuilt and are canceling contracts, Brandon R., who runs a land-entitlement fund, told a Family Office Club panel on Centimillionaire Strategies.
Investor panels usually trade winning deals. Brandon and three other operators each named the mistake that cost them most: Rich J., who runs a debt fund of about $800 million; Richard, a contrarian value investor; and Karl P., founder of the home-care software company OnTime ATS.
"The mistake was going all in on dirt for the biggest national home builders in the country." — Brandon R.
Brandon is now putting up his own equity to protect his investors. Rich lent through the 2008 crash and changed how his fund lends because of it. Karl built the timesheet software he then held back from customers.
The full episode is covered here so you can skip it.
Here are the 4 lessons that matter.
Centimillionaire Strategies · Oct 24, 2026
With Brandon R., Land Entitlement Fund Operator · Rich J., Debt Fund Operator · Richard, Contrarian Value Investor · Karl P., Founder of OnTime ATS
Key Takeaways
Going all in on land for the biggest national homebuilders was Brandon's costliest mistake
He is putting up his own equity to protect his fund's investors
The Southeast's biggest builders have overbuilt and are pulling back
Buyers have stalled over AI job fears and 6.5–7% mortgage rates, in a slowdown Brandon compares to 2008 for different reasons
One fixed exit plan on single-asset loans forced Rich's fund to sell at the wrong time in 2008
The fund, about $800M, now lends against portfolios instead
Buying sectors the market has written off is Richard's edge, a view he ties to Oaktree's Howard Marks
Karl delayed OnTime ATS to match incumbents' features instead of launching the one solution that already worked
1. Too Much Land, One Buyer
Brandon's fund entitles land, taking it through zoning and permit approval so it can be built on, and sells it to homebuilders. He concentrated the fund on deals for the largest national builders.
The largest Southeast homebuilders are canceling land contracts
"The biggest builders in the country in the Southeast have overbuilt and they're pulling back." — Brandon R.
A fund that sold mostly to those builders loses its main buyers when they pull back together. Brandon said he is putting his own equity into the fund to protect its investors.
Brandon compares the housing slowdown to 2008, for different reasons
"They're worried about losing their jobs to AI. They don't want to pay a 6 and a half, 7% mortgage." — Brandon R.
Brandon listed three causes this time: sub-3% mortgage rates, buyers' fear of losing their jobs to AI, and current rates of 6.5–7% that buyers will not pay. None of the three was the cause in 2008.
