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"Theoretically, a startup that actually wants to compete on compensation by sharing in good fortune could craft an equity package which is simple and standardiz

"Theoretically, a startup that actually wants to compete on compensation by sharing in good fortune could craft an equity package which is simple and standardized enough to be comprehensible by ordinary humans." One time, I received an offer from a small, struggling startup. But because it's equity structure was so simple (struggling has a way of simplifying things), I counter-proposed taking less salary for more equity, and they agreed. With the typical equity opacity removed, I viewed the trade-off as more of a bet on myself: the impact that I could make and if I assessed the company correctly. The payoff when we were acquired was just the equivalent of a nice extra bonus. The real satisfaction was having more skin in the game, having the expected impact, being correct on the assessment, etc. But it wouldn't have happened if I felt lost in the complex equity structure and confidentiality barriers that seem to be present in many startups.

kornish 6y ago
What made the offer simple compared to typical modern SV startup offers?
- pointyfence 6y ago
  Just one class of common shares for all the investor groups. New money didn't appear to be coming in. We were either going to go poof, or we were going to get sold. I'm a sucker for turnaround plays because a lot of BS gets beaten out of the organization, and they're more receptive to change.
cabaalis 6y ago
Having done this also, one point of care to take: Make sure your salary is right-sized post-acquisition. The buying company will likely have operating capital requirements based on existing PNL. Assuming you stay on, which key employees will likely have to, your low-salary position could be directly imported into the new position at the new company.
- myblake 6y ago
  No one can require you to stay on though, you’ll either have sufficient equity or bonus potential to make up for the lower salary, a salary adjustment, or you’ll just walk for a market salary.
  - cabaalis 6y ago
    Key employee not coming on could jeopardize the sale. A good bargaining chip.
sk5t 6y ago
It sounds like you actually didn't care about the money or risk/reward, yes? Don't you think it's a lot easier to meet your own expectations under such conditions, as compared to the calculus of startup-joiners hoping for a healthy financial outcome?

kornish 6y ago

What made the offer simple compared to typical modern SV startup offers?

pointyfence 6y ago
Just one class of common shares for all the investor groups. New money didn't appear to be coming in. We were either going to go poof, or we were going to get sold. I'm a sucker for turnaround plays because a lot of BS gets beaten out of the organization, and they're more receptive to change.

cabaalis 6y ago

Having done this also, one point of care to take: Make sure your salary is right-sized post-acquisition. The buying company will likely have operating capital requirements based on existing PNL. Assuming you stay on, which key employees will likely have to, your low-salary position could be directly imported into the new position at the new company.

myblake 6y ago
No one can require you to stay on though, you’ll either have sufficient equity or bonus potential to make up for the lower salary, a salary adjustment, or you’ll just walk for a market salary.
- cabaalis 6y ago
  Key employee not coming on could jeopardize the sale. A good bargaining chip.

sk5t 6y ago

It sounds like you actually didn't care about the money or risk/reward, yes? Don't you think it's a lot easier to meet your own expectations under such conditions, as compared to the calculus of startup-joiners hoping for a healthy financial outcome?