Every executive (startup or otherwise) needs to be accountable to the rest of the leadership team and the company’s board.  This is pretty obvious.  It is perhaps even more critical at startups compared to larger companies as larger companies typically have more executives who can mitigate the negative impact of one under-performer.

In my experience, lack of willingness to be accountable is one of the leading “business” reasons for executives resigning or getting fired.  I write “business” reasons to set them apart from non-work related matters.  Here are some red flags for non-accountability:

1. Failure to communicate in terms that are clear and concise. This might be a sign of communication inability or just dancing around lack of good results.
2. Failure to give explanations that make business sense. I have seen this from engineering heads, for example.  Even for complex engineering problems the head of engineering needs to be able to explain to the rest of the team what those problems are and how they are being solved.
3. Failure of a sales executive to talk actual numbers ALL the time. This is a big one.  To have any credibility, the head of sales must be crazily numbers focused. Building customer relationships only goes so far – getting orders is what counts ultimately.
4. Hearing “almost done” too many times.  Almost done = not done.
5. Inability to deliver simple things to CEO after repeated requests.  This needs no explanation.

I would love to see some more red flags in the comments so please chime in.  If you see red flags, act quickly, which is often very hard to do.

I was recently in a board meeting and the topic of change of control stock option vesting acceleration came up.  I wrote a pretty long post on this topic already so won’t rehash the basics again here.  But the recent discussion confirmed my view that double trigger stock option vesting acceleration is very clunky, difficult for management teams to understand when it actually matters (at the time leading up to the change of control) and, in my view, should be used infrequently.  I am pretty sure that my view on this is not that widely shared.

Absent provisions in a stock option plan or stock option agreements issued under a plan, an employee’s unvested stock options will simply terminate on a change of control (this is the default plan rule).  This makes complete sense – once a company is sold in a change of control, the actual stock underlying the option is worthless going forward (in other words there is no longer a company to hold equity in as it was sold).

When a company is sold it is often very attractive for option holders to have their vesting accelerate immediately prior to the time of the change of control.  This allows the option holder to participate in the change of control exit to a greater equity extent assuming the options are in the money.  As pointed out in my prior post, option agreements may provide for single (just the change of control) or double trigger (change of control followed by termination of the employee following the change of control) vesting acceleration.

Implementing double trigger acceleration is often really confusing for the option holder (who likely worked hard to get the company sold).  Implementing single trigger is easy, understandable and better for the option holder (again, who likely contributed to getting the company sold!!).  So, I remain a big fan of single trigger.  Simple = more understandable = better for the management team.

Critically, change of control acceleration is NOT standard.  Often it will just apply to senior members of the company’s team.  If the board (who grants options) is concerned with inadvertent windfalls (like when a senior team member joins 6 months prior to an unpredicted change of control and has vesting acceleration), then there are very easy ways to avoid that.  Just have the single trigger acceleration kick in after a set period of time (like 2 years after employment starts) or have it apply ratably over a time period (like 25% of unvested options accelerate if the team member has been employed less than one year, 50% if less than 2 years, etc., so that any windfall is limited).

My overarching theme is that team members work hard to get to exits.  Without the hard work of a senior team a good exit won’t happen.  Reward them with single trigger acceleration.  All incentives will be aligned and, most importantly, the team members will fully understand what they have in terms of equity potential.

Happy Halloween!

Sorry for the big gap in posts!

As a bunch of you probably know, James Holzhauer is on a streak to set the record for Jeopardy game show wins.  I just read that the show picks back up on May 20th with “live versions” (which are actually taped).   I do not watch Jeopardy at all.   But, the news stories have caught my eye so I have read a few of them.   The other day I came across a print interview that included this question:  Would you describe the traditional way of playing “Jeopardy!” as overly risk-averse?

Holzhauer’s answer: “I would definitely say it’s too risk-averse. The funny thing is, my strategy actually minimizes the risk of me losing a game. There’s times in a football game where a team goes for a big TD pass. If you don’t take a risk like that, you’re not going to win. Really, the big risk is never trying anything that looks like a big gamble.”

In case you don’t know, a core part of Holzhauer’s strategy is to go after the $1000 “answers” first so that he builds up a pot to bet when he hits a daily double.  This is why he is the fastest money winner in Jeopardy history.

Anyway, I loved his answer as it made me think of many entrepreneurs – they take risk all the time!  And guess what, so do VCs when they bet on those entrepreneurs!  Risk is a given and taking risks is required.