Board Questions to ask about Stock Options, NSOs, ISOs, Restricted Stock, Restricted Stock Units (RSUs).

[Earlier I wrote about the different vehicles] You're sitting on a board and the CEO presents some proposed grants. Motion to approve - second - all in favor - ay. Here's what you should have asked before the board meeting. A. Economics What's the vesting schedule? What are these options worth right now? What do … Continue reading Board Questions to ask about Stock Options, NSOs, ISOs, Restricted Stock, Restricted Stock Units (RSUs).

The Pitfalls of Benchmarks.

Benchmarks are great to tell you where you are compared to others. In venture capital, there are three common problems with benchmarks: History, math, and ego. 1. Benchmarks are History Benchmarks are backward looking. Past performance is no guarantee of future results. Maybe market mechanics changed. Maybe the supply and demand of startup funding in … Continue reading The Pitfalls of Benchmarks.

The Future of IT: The Next Five Years.

Enterprise CTOs or CIOs often ask me about how IT will change in the future, about the "Disruption of Technology in 3-5 years". Most CTOs and CIOs realize that that is primarily a strategic question rather than a question about a certain vendor or technology. I usually explore the specific challenges together with the executive … Continue reading The Future of IT: The Next Five Years.

Digital Transformation Strategy — You Don’t Need One.

I talk a lot with very large enterprises in Europe, Asia, and Latin America.  Sometimes they have a question regarding their IT infrastructure, sometimes they want to hear about shifts in industry trends (few of them want to hear 'trends in the Silicon Valley,' thank god!). Sooner or later they tell me about their digital … Continue reading Digital Transformation Strategy — You Don’t Need One.

“Flipping” your Company to the US?

I mainly help U.S.-based companies set up shop and scale for revenue in non-US regions. But I see more and more interesting deals where European or Asian companies are coming to the U.S. (Disclaimer!) There are usually two considerations why companies (startups and enterprises alike!) set up a dedicated U.S. entity: international regulations and litigations, … Continue reading “Flipping” your Company to the US?

Bring me Problems.

The management-craze of "bring me solutions" has gone too far. I recently met with two spin-out teams of enterprises where the engineers and interim-CEO were scared to share any challenges or problems with corporate management because they were expected to be more "solutions-oriented." When I went back to one of the senior executives with a problem … Continue reading Bring me Problems.

HBR Whiteboard Session: 4 Things Successful Executives Do Differently.

Wow, just re-found this 5 minutes 56-second video with I had bookmarked. I usually hate these "Five Things Successful Executives Do" etc., but this one was a pretty good framework of four recurring patterns -- instead of "do your taxes yourself." or "smile more." or all the other nonsense you read on clickbait. This one has … Continue reading HBR Whiteboard Session: 4 Things Successful Executives Do Differently.