What Are The Limits of Tolerance?

I’ve had an emotionally challenging morning so far. I woke up too early and was deeply agitated. I tried to get rolling, couldn’t, and went back to bed. But I wasn’t able to fall asleep and my brain kept cycling on all the political chaos and societal hatred that is going on. I’ve tried to compartmentalize it but it broke through again the last couple of days after Charlottesville.

I got up and realized the Internet was down. I decided to just go running. Two minutes in, Brooks came up lame and I walked him back home. I started again with Cooper but my left knee was a little twingey so I decided to bail and take a few rest days. The Internet was still down.

Amy and I then spent time at breakfast talking about how to reconcile the intolerable. I felt a little better and was helped by Fred Wilson’s

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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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