Lunch with Your CEO: 7 Great Questions to Ask.

Grab your CEO and have lunch. Chances are, she has once started just like you. And everybody has to eat at some point. Here are some questions that are great for getting some insights on strategy, challenges, and culture -- even if you only have five minutes: What the biggest frustration in your job? What's … Continue reading Lunch with Your CEO: 7 Great Questions to Ask.

Sales Strategy — Selling a Product Versus Selling a Platform.

What does your customer want to buy? Are they using your product as a stepping stone or enabler to a much bigger transformation? Or are you part of a larger product and fit the puzzle? Are you selling a product or a platform? I listened into sales conversations at one of our startups. The product … Continue reading Sales Strategy — Selling a Product Versus Selling a Platform.

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.

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.

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.

Negotiations: Focus on What You Don’t Know.

I remember one sentence from the many books I read while doing business in Europe, the Middle East, and Asia: Your relative power in a negotiation is your capacity to use resources to influence another’s circumstances. In 1962, Richard Emerson published Power-Dependence Relations. I found that Richard's focus on "In how many ways can I demonstrate my … Continue reading Negotiations: Focus on What You Don’t Know.