Last night a dinner discussion turned again to private equity markets, blockchain, stablecoins, and money. The argument went that public markets had less risk because they have stricter audits, governance. In private equity, you also have to find a buyer and negotiate a price and terms of your private equity stake. Stocks that are traded … Continue reading How to think about risk in Blockchain, Private Equity, Public Markets
When I came out of my own startup in 2002, I decided to focus my efforts on public land preservation and low-income housing. I signed a bunch of different (financial) products, and quite frankly didn't know much about US products, closed-end funds, and tax implications. When I had to restructure our family trust, I had … Continue reading $125M Evergreen Fund
Aside from the Books I Recommend, I noticed that every two weeks or so someone asks me about good blogs or podcasts to follow. For the longest time I had mixed feelings about it. Books are static. The opinion (and sanity) of bloggers and podcasters might change. I also don't catch every podcast or blog … Continue reading Podcasts and Blogs I Recommend.
Statistically, startups mostly fail. We love to think of ourselves as great investors. But Venture Capital fundamentals still didn't change: Fund returns are driven by outliers, and returns are concentrated in few firms. All VCs are constantly evolving and refining their thinking, processes, conviction. That's why we write long investment memos: Not because be need … Continue reading Venture Capital: Preparing for Failure.
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.
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.
[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).
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.
[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.
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.