I found this wide ranging interview quite interesting.

Alex has been an entrepreneur and is now an investor.

He is operating at the intersection of traditional fintech and crypto, which is a place USV also often occupies.

I backed this documentary film project earlier this week.

I want to see this film made and shown. If you do as well, you can back this project here.

Given the political nature of this post, I have closed the comments.

Something I am a huge fan of is Board Feedback. I’ve written about this a lot here at AVC and I am writing about it again today. Because it is important and not done regularly in my experience.

A founder/CEO and their team spend a lot of time preparing for a meeting, and then they give the meeting their all, and often the Board leaves and nothing is really said about it.

That sucks. For everyone, but most of all for the CEO.

Here is what I try to do and mostly do. I sometimes mess this up but not often.

After the meeting ends, at least one director, ideally the Chairman if there is one who is not the CEO, or the lead director, or the director who is there in person, should lead an executive session without the CEO and get feedback from all of the directors and observers and then they should sit down with the CEO and provide that feedback in an honest and open way.

The sooner you do this the better. No CEO should ever be wondering how the Board Meeting went, what people are thinking, and how they are doing.

And yet that is often the case. That is malpractice. It is wrong. It should not happen.

Last week I started getting lots of stories about Kendrick Lamar and SZA in my Google Now news feed on my phone.  I thought to myself “why all of sudden does Google think I’m interested in Kendrick Lamar and SZA?”

Then I recalled sending a text message to my son about the new Kendrick/SZA song from the Black Panther film and thought “Google saw that text message and added Kendrick to my interests.” I don’t know if that is in fact the case, but the fact that I thought it is really all that I am talking about right now.

That whole “why did I get this recommendation” line of thinking is what the machine learning industry calls Explainability. It’s a very human emotion and I bet that all of us have it, maybe as often as multiple times a day now.

I like this bit I saw on a blog post on the topic today:

Explainability is about trust. It’s important to know why our self-driving car decided to slam on the breaks, or maybe in the future why the IRS auto-audit bots decide it’s your turn. Good or bad decision, it’s important to have visibility into how they were made, so that we can bring the human expectation more in line with how the algorithm actually behaves. 

What I want on my phone, on my computer, in Alexa, and everywhere that machine learning touches me, is a “why” button I can push (or speak) to know why I got that recommendation. I want to know what source data was used to make the recommendation, and I’d also like to know what algorithms were used to produce confidence in it.

This is coming. I have no doubt about it. And the companies that offer it to us will build the trust that will be critical to remaining relevant in the age of machine learning.

Our portfolio company DuckDuckGo which offers a search engine that doesn’t store your search history or track you announced some new offerings this week.
Here’s a quote from the announcement:

Over the years, DuckDuckGo has offered millions of people a private alternative to Google, serving over 16 billion anonymous searches. Today we’re excited to launch fully revamped versions of our browser extension and mobile app, extending DuckDuckGo’s protection beyond the search box to wherever the Internet takes you.

As I understand it, you can get this browsing protection via the DuckDuckGo mobile app and from their browser extensions.
You can get them here:

Firefox, Safari, Chrome, iOS, and Android

DuckDuckGo is moving beyond search into a broader suite of privacy offerings. They have built up the trust of users over the years and can now apply that to a wider set of problems.

Along the way DuckDuckGo has built a great business too. As founder/CEO Gabe Weinberg explains in this interview with Techcrunch, DuckDuckGo has been profitable since 2014.

It’s very satisfying to me to know that in an era where billions are being made walking all over our privacy, a great business can be built protecting it.

ADP announced this morning that they have acquired our portfolio company WorkMarket.

This is a bittersweet moment for me.

WorkMarket has been a big part of my personal portfolio for almost eight years.

USV and Spark seeded WorkMarket in June 2010, backing two serial entrepreneurs Jeff Leventhal and Jeff Wald.

The idea was to create a cloud based SAAS application to allow enterprises to manage their contingent workforces which were growing in size and complexity. It seemed like a timely opportunity at the time and it was. Eight years later the SAAS contingent workforce management market is in the hundreds of millions of dollars annually and WorkMarket is the creator and leader of it.

But like all startups, the WorkMarket story has a number of twists and turns. The market was a bit slower to develop than we had initially hoped and it wasn’t until the last few years that big companies started to include contingent workforce management in their SAAS budgets.

We also lost one of the two founders, Jeff Leventhal, when he stepped aside at the end of 2014 and was replaced as CEO by Stephen DeWitt who was recruited to the opportunity by Jordan Levy, who has been everything you could ask for in a co-investor.

The last few years at WorkMarket have been amazing. The senior team that Stephen and Jeff Wald built is among the best that I have had the opportunity to work with. And the contingent workforce market really exploded in 2016 and 2017.

But like all exploding markets, the expanding opportunity brought a lot of new entrants and buyers interested in getting into it. And one of those big companies, ADP, made us an offer we could not refuse, both in terms of the financial opportunity and the fit with their business. ADP has been helping enterprises, large and small, with human capital management solutions for decades and has the customer base, market knowledge, and capital to lean into this opportunity in a way that a venture backed startup never could.

So WorkMarket is now part of ADP and I am pleased with that outcome. Jeff Wald will take over leading WorkMarket for its next phase and he is well suited and deserving of that role. He has been the one constant for the eight years that I have worked on WorkMarket. Everyone else who was there at the start has come and gone. But Jeff and I saw it through from start to finish and I appreciate that very much.

I also want to acknowledge Stephen and the senior team of Grady Leno, Jim Chou, Marcy Shinder, and Tom Benton. As I said, this is an amazing team and it has been a pleasure to watch them build the product, market, and customer base. They are all superstars in my book.

This is the way of the VC business. You get inspired by an idea and a couple founders. You spend a lot of time helping them build something. You give a piece of yourself to the business. And one day, you are done. That day, for me and WorkMarket, is today and I have enjoyed the ride very much.

It’s that time of year again. The Gotham Gal and I are spending the rest of the winter out west.

Blog posts will start coming in around 6am PT/9am ET.

We plan to spend this winter in Utah (where I am now), LA, and I will also be in the Bay Area a fair bit.

I find this time of year to be particularly invigorating for me.

Getting out in the fresh air and skiing, biking, and that sort of thing always gets me going.

But it’s mostly about reducing the back to back to back meeting grind that my work day in NYC has become and replacing it with reading, writing, thinking, and dreaming that I find so helpful.

The Gotham Gal and I are going to go out and ski the 16″ of new powder that we have gotten in the past 48 hours this morning and then go see some great indie films this afternoon.

Should be a great Sunday.

This was seven years ago. I went back and watched it recently and it has stood the test of time.

I want to see this documentary when it comes out so I backed it on Kickstarter today to make sure it gets made.