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).

Five Areas of Startup Equity Awards Boards Should Discuss.

There are enough primers on the Internet. This is not a primer. But take it as a discussion guideline with your board, your lawyers, your executives. Types of Equity Awards Options An option is a contract between a startup and an "optionee" (mostly employees, but could be contractors or board members) that provide a right … Continue reading Five Areas of Startup Equity Awards Boards Should Discuss.

EU / UK / U.S. Data Transfers after Brexit.

[Disclaimer 1: This is not a primer on Brexit -- google it.] [Disclaimer 2: I'm not a lawyer, consult your own!] GDPR and Brexit The GDPR came into force on May 25th, 2018, and is applicable in the UK. It is implemented through the UK Data Protection Act 2018 (short: "DPA") and will remain applicable … Continue reading EU / UK / U.S. Data Transfers after Brexit.

Pitch Clinic: Sell Stock, not Product

I know you have a great product. I wouldn't be talking to you otherwise. But I am not a customer. I am a potential investor. As the CEO, you have been juggling all sorts of crisis situations over the past year, and you have been at the forefront of selling, probably meeting with customers and … Continue reading Pitch Clinic: Sell Stock, not Product

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.

Jocko and Startups: Default Aggressive.

[There are countless obvious lessons from Jocko's books and podcasts that apply to all people and all companies. Here are some insights that might be less obvious from the last #muster.] Some VCs talk about startups needing to be paranoid, with an obsessive attention to what is going on in the environment around them. I … Continue reading Jocko and Startups: Default Aggressive.

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.

Jocko and Startups: Am I a good Leader?

[There are countless obvious lessons from Jocko's books and podcasts that apply to all people and all companies. Here are some insights that might be less obvious from the last #muster.] As board members and VC investors, we often get asked: "What are your other companies and CEOs doing? Am I a good leader?" Most … Continue reading Jocko and Startups: Am I a good Leader?

What’s Hard and What’s Not as a VC.

I often ask entrepreneurs during pitches "What's hard to make this a successful company?" I am particular about this one.  I am not asking "what's difficult." Difficult is fundraising, hiring great people, finding customers, making customers pay on time, getting renewals, opening a new office, etc. "What's Hard" is something that hopefully the entrepreneurs are better … Continue reading What’s Hard and What’s Not as a VC.

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.