Is using structured financing terms (e.g., guaranteed returns, conversion thresholds) to bridge a valuation gap a sound practice, or does it create harmful misalignment?
5 recorded positions from 3 people, first said Oct 11, 2023. They do not agree — the readings below are what each one actually argued.
Also on the record
Deven Parekh · Oct 11, 2023
Raising a heavily structured security to preserve a stale headline valuation is the most dangerous thing a company can do
It creates an artificially high valuation inconsistent with current values, makes it harder to strike the 409A where it should be, and is not intellectually honest with employees who already know the valuation isn't flat
13:50 Structured financing to preserve a stale valuation is the most dangerous choice a company can make
Jason Lemkin · Oct 11, 2023 · hedged
A modest amount of structure to bridge a valuation gap is not the disaster the internet makes it out to be
If founders are in it for ten years and intend to IPO into a much larger outcome, a guaranteed 2x for the investor is debt-like but tolerable — Box and others had structure at IPO
14:46 Modest structure to bridge a valuation gap is tolerable for long term holders aiming at ipo
Deven Parekh · Oct 11, 2023
Structure only looks fine in the scenarios where the bet pays off; its cost shows up when the outcome disappoints
Like betting at a casino — betting on red and winning is great, the problem is when it comes up the other way
15:29 Structures appeal fades once the downside scenario actually materializes
Woody Marshall · Oct 11, 2023
Structure is bad because it puts investors and founders on different sides of the table, creating 'heads I win, tails you lose' motivations
Value creation should benefit everyone equally; differing securities create differing outcomes and therefore differing incentives when things don't work
15:39 Structure creates heads i win tails you lose misalignment between investors and founders
Deven Parekh · Oct 11, 2023
Structured rounds with conversion thresholds destroy alignment at exit, because founders will refuse a good strategic offer that sits below the conversion trigger
Roughly 75% of such companies never go public, so the realistic outcome is a strategic bid — and a 2x conversion hurdle turns what would be a good exit for both parties into a fight
16:55 Structured conversion thresholds destroy exit alignment since most companies never ipo
Your assistant can query this graph directly — 5 positions here, 19,646 across the corpus. Add 996.fm over MCP.