Every Generation Learns The Same Lessons

While it’s easy to tell people things, it’s much more powerful to learn things. And, as I get older, I see the same lessons being learned by subsequent generations. While this isn’t a post that says “everything is the same as it was before”, there are foundational lessons in life that play out over and over again.

I spent the weekend with a friend from the last 1990s who was the lead banker on the Interliant IPO (I was a co-founder and co-chairman.) Last night, at the Aspen Entrepreneurs event, I was asked to describe several failures and I rolled out my story about Interliant, which, for a period of time (1999 – 2000) appeared to be hugely successful before going bankrupt in 2002. If you like to read IPO prospectuses, here’s the final S-1 filing after INIT went effective and started trading on July 8, 1999.

A few

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Capital Should Follow Talent

I love today’s post from Fred Wilson titled The Valuation Obsession. It has some good hints in it about valuation vs. ownership dynamics for founders, employees, and investors. It also calls out the silliness about focusing on the wrong things.

Go read it.

I’m even a bigger fan of a statement Fred makes in the post that William Mougayar calls out in the comments.

“I like to invest in companies that smart people are joining. Capital should follow talent, not talent following capital.

This is not just a statement on capital. It’s another hint to the importance – to a founder – of building an awesome team at every level of the journey. It matters at the beginning, as things ramp, and as a public company.

Capital should follow talent. That’s a line I know I’ll be using. I’ll try to remember to say “Fred Wilson says capital should

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The Past, Present, and The Future

The past is ungraspable,
the present is ungraspable,
the future is ungraspable.

– Diamond Sutra

Now that it’s 2018, the inevitable predictions for 2018 are upon us.

I’m not a predictor. I never have been and don’t expect I ever will be. However, I do enjoy reading a few of the predictions, most notably Fred Wilson’s What Is Going To Happen In 2018.

Unlike past years, Fred led off this year with something I feel like I would have written.

“This is a post that I am struggling to write. I really have no idea what is going to happen in 2018.”

He goes on to make some predictions but leave a lot in the “I have no idea” category.

I mentioned this to Amy and she quickly said:

And that, simply put, is my goal for 2018.

As I read my daily newsfeed this morning, I came

Continue reading "The Past, Present, and The Future"

The Past, Present, and The Future

The past is ungraspable,
the present is ungraspable,
the future is ungraspable.

– Diamond Sutra

Now that it’s 2018, the inevitable predictions for 2018 are upon us.

I’m not a predictor. I never have been and don’t expect I ever will be. However, I do enjoy reading a few of the predictions, most notably Fred Wilson’s What Is Going To Happen In 2018.

Unlike past years, Fred led off this year with something I feel like I would have written.

“This is a post that I am struggling to write. I really have no idea what is going to happen in 2018.”

He goes on to make some predictions but leave a lot in the “I have no idea” category.

I mentioned this to Amy and she quickly said:

And that, simply put, is my goal for 2018.

As I read my daily newsfeed this morning, I came

Continue reading "The Past, Present, and The Future"

Lessons From The Internet Bubble: Growth vs. Profitability

Over the weekend, Mark Suster and Fred Wilson each put up awesome posts discussing the idea of profitability in startups. Mark’s is a master class about how to look at the financial characteristics of a startup and Fred’s discusses what he’s been working on with some of his more mature companies. They are both worth reading right now. I’ll be here when you get back. Between the spring of 2000 and the end of 2001, I had the worst, most stressful, and most painful business period of my life. While I’m sure the financial crisis of 2008 was worse for many people, for me it paled in comparison to the misery of this 21-month stretch. A very simple thing happened that year in my world. The market shifted from rewarding (and funding) growth to rewarding (and funding) profitability. It happened over a few quarters, but with the perspective of time
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The Best Time To Invest In Something Is …

At 18 minutes into this awesome talk that Fred Wilson did at MIT a few weeks ago, he finishes the statement “The best time to invest in something is ...” … when nobody wants to invest in it but you.” He adds “And – you have to believe in it and know why.” Truer words have never been spoken about investing as, or in, VC. Just don’t forget the phrase “and – you have to believe in it and know why.” Fred is one of my closest friends in the VC business and someone I’ve learned an amazing amount from him since first meeting him in 1996 when he was just starting to work with one of my male soulmates Jerry Colonna. Watch the video. Listen carefully. Learn from his experience. Fred – thank you for everything you’ve done for and with me
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Monthly Match: National Immigration Law Center #NILCMatch

Fred Wilson, Joanne Wilson, Amy, and I are doing our second Monthly Match. This one is in support of the National Immigration Law Center. We will be matching $20,000 of contributions that our respective communities make to NILC. We’ve made it easy to contribute – simply go to this page on Crowdrise. Any level of contribution is super helpful. Since we are matching 1:1, each dollar you contribute gets NILC another dollar. The four of us did this on an impulse last month after the Executive Order on Immigration hit. We were all extremely upset about the executive order and decided to do something about it. We ended up raising over $120,000 for the ACLU over the weekend during a period where the ACLU got a lot of visibility for making the first major move against the executive order and ended up raising over $24m. As a result,
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Why the Micro-VC Surge Will Drive Innovation Across the US

The following was co-authored by Ezra Galston of Chicago Ventures(@ezramogee) and Samir Kaji (@samirkaji) of First Republic Bank. Over the last several years much has been made of the opportunity, or perceived lack thereof in technology centers outside of the Bay Area and NYC. From Steve Case’s Rise of The Rest Tour, to Google for […]

We Were Right – Just a Decade Early

This is a line my friend Jerry Colonna uses when something like the AT&T – Time Warner deal occurs. As time passes, the line has shifted to “We were right – just fifteen years early.” Jerry was Fred Wilson‘s partner at Flatiron Partners. We were all investing in Internet-related stuff at the end of the 1990s. Jerry and Fred had one of the most successful VC funds during this time period until the Internet bubble burst and blew us all up for a while. We made plenty of investments together and I sat on a number of boards with Jerry – we had some big winners and a handful of craters in the ground. At the peak, AOL bought Time Warner for $162 billion. We only know that was the peak in hindsight – at the time it looked like it validated a lot of what we were doing
Gartner Hype Cycle
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Love and Venture Capital

If you’ve missed me, it’s because I spent a week in Australia. Ten days ago, after being there for a few days, I came down with salmonella poisoning. I’m finally starting to feel normal again although I’m still exhausted. This has easily been the sickest I’ve ever been. While I was gone, the gang at Reboot put up the Reboot Podcast #45 – What’s Love Got to Do with It?- with Fred Wilson and Brad Feld which was a delightful conversation between me, Fred, and Jerry Colonna. The three of us have a 20+ year history that gives me joy every time I think about it. I first met Fred in the suburbs of Boston at Yoyodyne in 1996. It was also the first time I met Seth Godin. I had just started working with Softbank and had been commanded to go to Yoyodyne and do “due diligence” by Charley Lax. I had
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Reflections on Nice Going Into The Weekend

I woke up feeling subdued this morning. I didn’t know why but after talking to Amy I realized that the emotional impact on me of the horror in Nice is weighing on me. Amy described her connection to it to me – she’s been physically in the same spot that the tragedy happened – and even though we are far away, something very personal hit home about the whole thing. We are long-time friends with Fred and Joanne Wilson. After my call with Amy, I did my daily news routine, which includes a few minutes in Feedly skimming all the blogs I subscribe to and reading the ones that catch my attention. Both Fred’s and Joanne’s did today. I read Joanne’s post from yesterday titled Pledge 1% first. It perked me up a little and made me smile, as Pledge 1% is the evolution of the Entrepreneurs Foundation of Colorado
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The Hidden Challenges of Starting a Company in Secondary Markets

Fred Wilson’s much debated post, Second and Third Tier Markets and Beyond, sparked an important discussion about operating and investing in businesses outside of the Valley. Case in point: within 48 hours, the piece generated a heated Twitter exchange (including input from the one and only Bill Gurley), a Pitchbook analysis of the best M&A outcomes […]

Fred Wilson and Tim Armstrong say policy matters for New York’s tech growth

tcdisrupt_NY16-4843 Against a backdrop of a New York investment scene that’s been long on promise and press and somewhat lacking in terms of exits, tech icons Fred Wilson, co-founder of Union Square Ventures, and Tim Armstrong, (my boss’ boss’ boss) chief executive of AOL, have come together to launch Tech:NYC, a new lobbying group for the technology community in New York. While Wilson conceded… Read More

Do You Regret Failed Investments?

This weekend I’m co-hosting the Reboot.io VC Bootcamp at my house in Boulder. It starts tonight and goes through mid-day Sunday. It’s an experiment with Jerry Colonna and about 15 other VCs to see if the Reboot.io bootcamp construct, where the tag line is:
Practical Skills + Radical Self-Inquiry + Shared Experiences = Enhanced Leadership + Greater Resiliency
It’s either going to be valuable to this group or not. We’ll know more on Monday. The only way to learn is to try. As part of the pre-work for the weekend, I went back and re-listened to several of the Reboot.io podcasts that Jerry recommended in advance (for you Soundcloud people I made a Reboot.io VC Program collection.) So, my brain was already trending toward the headspace around radical self-inquiry in the context of
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What I Use My Phone For

Bijan asked me about this in the hallway chat I did with him and Nabeel last week.  According to my battery usage data (which may be a bad proxy for usage), I use my phone for:
  1. Gmail
  2. Soundcloud
  3. Chrome 
  4. iMessage
  5. Swarm
  6. Twitter
  7. Phone (voice)
  8. Foursquare
  9. Google Now
  10. Kik
I wrote this post on my phone too

Artificial Art

Last week we opened up a new thread on USV.com to think about and discuss the intersection of creativity (art) and artificial intelligence. We have seen a lot of interesting companies in this area but have not yet made an investment. Of course, the entire notion that machines will help us make art or even make it without human intervention gets to the essence of what art and creativity are. Last summer I posted an art project by Ian Cheng that my daughter was involved in. The cool thing about that art project is that it evolves over time based on rules provided to a machine. The art is initially made by humans but it evolves and changes over time using a machine. That is one of many interesting ideas that artists are exploring at the intersection of creativity and computing. An existential question that society is grappling with right now is how humans and machines will co-exist in the future. And one of the roles of art, maybe it’s most important role, is to force us to confront issues like this. So while the idea of using a machine to make a song or an image or a novel or a sculpture without human intervention is at some level disturbing, it is also revealing. We expect that artists will push the envelope of what is possible with technology and we also expect that technologists and entrepreneurs will be willing collaborators in this effort. Whether this will lead to interesting investment opportunities is anyone’s guess, but we think it might. And so we are going to spend some of our time and energy thinking about it and we’ve created a public space to do that. If you are interested in this area you can follow the thread and contribute to it here.

Hallway Chat

Yesterday I hung out (virtually) with Bijan and Nabeel at Spark Capital and joined them in their podcast they call Hallway Chat. Here’s what we talked about: -questions from Twitter, including how Fred started investing in social media, & YC’s recent move to recommend exercising options from 90 days to 10 years -Fred’s post, “The New Entertainment Bundlers” -Chris Dixon’s, “What’s Next In Computing?” -Why haven’t we seen a new breakout consumer app -AI -Steph Curry vs Michael Jordan So, here’s our “hallway chat”

Become A CSNYC Founding Partner

Three years ago, I co-founded the nonprofit organization CSNYC to address the extreme scarcity of computer science education in the NYC public schools. I am proud to say that we are now reaching nearly 10% of the city’s schools and more than 12,000 students. But our mission is to reach every school and every student. In September 2015, Mayor de Blasio and I announced Computer Science For All (CS4All), a 10-year, $81 million plan to bring computer science education to every student in New York City public schools. The costs of CS4All will be shared equally between the city and private philanthropy, and CSNYC and Robin Hood have each committed $5 million to get the initiative off the ground. As leaders in the local technology community, we collectively have the potential to support what will be the largest scaling of access to computer science education in the country. Early, meaningful access to computer science can change students’ educational lives and create pathways to future educational and career opportunities. These students are our future employees. I am reaching out to NYC tech companies to help fund CSNYC’s ongoing efforts by committing to an annual membership of between $5,000 and $25,000. As a CSNYC Founding Partner, you will support our work in the schools and enable us to connect your company to employee engagement opportunities, internship programs, and more. csnycpartnersPlease consider joining this distinguished group of companies: About.com, AppNexus, Bitly, Clarifai, Contour Ventures, Etsy, Facebook, HyperScience, Insight Venture Partners, Justworks, Kickstarter, MongoDB, Nestio, Postlight, Resy, Return Path, Simulmedia, Tapad, Techstars, Tusk Ventures, Warby Parker, and Yext. I am hopeful that we can add your company to this list.   If you are interested in joining as a CSNYC Founding Partner email us and we will follow up with you directly, or you can simply fill out our online membership form.