The Bridge Round Prices You
A structured bridge with discounts, caps, or preferences isn't a bridge. It's a down round in friendlier language.
The term sheet said bridge. At one company I sat close to, the headline was a $3 million SAFE that everyone called clean and founder-friendly, set to convert at the next priced round. The terms that mattered were lower down, in the discount and the valuation cap. Read together, they priced a Series B two notches below the last round, which is to say a down round with a bridge's paperwork. We told ourselves it bought eight months of runway. It bought a repricing.
The note converted at the next round. The cap table had moved twelve points further than the founder modeled, because he hadn't modeled it at all. The investor who led the bridge had bought, through the discount, more of the company than the headline implied. By the time anyone noticed, the signatures were dry.
Most structured bridges are priced rounds nobody negotiated as one. The format hides the math. Say the SAFE carries a 20% discount. That's the same as pricing the bridge well below the future round, which is the same as pricing today's round at that discount. The valuation cap does the identical job in a different costume. Two SAFEs with different caps and discounts convert at different real prices, and founders rarely run the numbers across the two or three Series B valuations that would show who is paying what.
It gets worse when liquidation preferences and anti-dilution ratchets ride along. A bridge with a 2x participating preference isn't a bridge. It's a priced round wearing hostile terms. The founder, eyes on runway, watches the cash land and skips the modeling.
The thing that prevents all of it is a conversion model. Before signing, build the cap table forward at three scenarios: flat at the last valuation, a modest up-round, a modest down-round. Each one shows your ownership after the note converts, measured against what the company is worth. With a competent CFO it takes an hour. It surfaces what the bridge costs, in dilution, across the futures that are plausible rather than the one you're hoping for.
Most founders skip the model, because building it means admitting the down-round is on the table. The skip is the cost.
The bridge was supposed to be the easy money, the friendly capital between rounds. It ends as the priced round you negotiated worst, on the day you weren't negotiating at all. The cash was never the expensive part. The terms under it were.