I signed a pref doc that let the sponsor put money in ahead of me and then he did
$900k into a pref position on a suburban office-to-flex conversion, 12% accruing, no current pay for the first eighteen months, 1.35x minimum multiple at redemption. I read the whole operating agreement. I flagged four things. I did not flag the one that mattered.
Buried in the additional capital section: if the company needed capital to cure a default under the senior loan, the manager could admit new preferred interests ranking senior to or pari passu with existing preferred without consent of the existing preferred members. I read that as a protective clause. It protects the deal, sure. It doesn't protect me.
Month twenty the senior lender called a covenant breach on the debt yield test. Sponsor brought in $1.6m of rescue capital at 15% with a hard first position in the distribution waterfall ahead of my 12%. Entirely permitted. My accrual kept accruing behind a bigger, faster-growing claim on the same cash.
We got out at a sale eleven months later. My 1.35x minimum multiple was a real contractual number and there simply wasn't enough proceeds behind the senior loan and the new pref to reach it. I received 1.08x on three years and one month. On paper that's a positive outcome and it's roughly half what a bank CD ladder would have felt like for the anxiety involved.
What I'd do differently: treat any language permitting new senior or pari passu preferred as a priming clause and price or refuse it accordingly. If a sponsor wants that flexibility, I'd want a consent right, or a cap on the dollar amount, or my multiple stepping up if it's used. Have counsel read the waterfall and the capital sections together, because each one looked reasonable alone.