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Granted 90% of the time I can't truly comprehend all the vernacular and terms. Heck I just "tumbled" in to Fred Wilson for the great tunes, but am quite glad I decided to stay for the full conversation. I say keep it coming. I'm having an absolute blast learning and it's a heck of a lot cheaper than Wharton. ;)
I think the challenge with your point is that the number you refer to as investment value is a tricky number.
1. It's too low and given that our job is to create 10x the value (minimally) that number might not seem very high (especially over 4 years)
2. That number (say @ Yelp or Heavy or Slide or something) could be very difficult to achieve when valuation has gone up in inflationary times. That can become misleading and entrepreneurs rarely say, "Well the value of this grant is $80,000 but hey that could become meaningless given our huge valuation and the preferences etc." To me this is Chris' broader point.
To me, Chris' post is more relevant by how entrepreneurs set expectations for their team and maintain their integrity by being candid and transparent. Everybody talks in small companies. So CEOs need to be honest and they will find that the truth will keep things far simpler.
I made an offer to a young man this week who has a chance to participate in a Ycombinator style program and maintain a majority of the equity in his anayltics startup. I strongly encouraged him to go for it, but he might join Nate and I because he wants to get better faster and come back to people like you with more experience. He's getting a very small percentage of this company, but over the length of his career it might very well make sense for him to join us.
Chris and Caterina are likely to do far better on Hunch than anybody else and that's fine. They started it. But if Hunch does well then it creates opportunities for everybody see PayPal Mafia or Google riffs Chris Sacca and FriendFeed etc.
Not everybody can be an entrepreneur, but if I've learned one thing over the past 12 years it's that you really don't know know who will be the best or why they will be.
Startup employees may choose small for the lifestyle, the autonomy or a whole host of other advantages. Equity compensation is nice, but I encourage my colleagues not to underestimate their ability to one day do it themselves. That can really, really pay off well.
If you enter Slide (post of $500mm or Yelp (post of $200+mm) maybe you will make money on the stock, maybe not. But either way if those companies do well and you were a key factor you will have positioned yourself well for the future. Long ago, that was me at Concrete Media and it paid off.
http://www.feld.com/wp/archives/2005/05/term-sh...
Google feld.com vesting and see what comes up
Happy side effect: you attract founders who want to do business the same way you do.
If you're comfortable sharing, I'd love to know what percentage of the company is typically granted for various positions based on your experience. If I were offered a VP role at an early stage startup, for example, what's a reasonable grant? I assume it varies by level (VP, Director, Manager, etc) and by company stage (at incorporation, pre-Series A, post-Series A, etc). Any benchmarks you can provide would be interesting to know.
"50% of something is a lot more than 100% of nothing."
My dad was the first person to tell me this, when I got started with BricaBox. With that venture, I owned well over 50% of the company still when I decided to close it. That well over 50% turnout to be of nothing.
With my new venture, I'm sitting well south of that 50% number, but with little sacrifice to ownership. Why is this?
It's because my "less" comes with "more" team of invested people. The more people who feel like meaningful owners of the Company (meaningful in terms of both % and their attitude towards it), the more valuable my Company is.
So, % matters, for sure -- it's the basis on which investors and employees can do real back-of-envelope dreaming -- but so does the culture around that number.
Chris' post originally was about how engineers could be more sophisticated about evaluating an options proposal. If you say to someone who doesn't know the drill, "the investment value of your options is $100k," they are going to think that is much the same as giving them $100k in cash.
BTW, I actually think the strike basically doesn't matter when it's an early stage company with super high volatility and strike is standard 20% or so of last round valuation. See http://www.cdixon.org/?p=259
Scott Edward Walker
Walker Corporate Law Group, PLLC
That being said, having worked with portfolio companies and the venture investors that fund them all of my career, I have not seen any evidence that Companies have ever tried to “trick” engineers or other employees by playing with the share numbers of a grant and keeping the percentage of the Company represented by the grant a secret. That is not to say it doesn’t happen, but these Companies generally grant options with the goal to incentivize their employees (partly to incentivize loyalty, partly as a salary substitute accepted by the recipient because of the upside potential) and any “trick” played by the Company will likely defeat this goal. Consequently, my experience has been that Companies generally grant options in an amount that they think will provide the respective employee with a sufficiently incentivize employees to give their best efforts in a job where the risks are much higher, but the rewards can also be much bigger than non-startup jobs.
Employees that cannot deal with some risk and uncertainty, both of which are great words to characterize options generally, are better off not working for a startup.