• #book
• #generation x

Generation X: Tales for an Accelerated Culture is weekend reading for anyone who wants to understand me and my generation.

I was born in 1965 – right at the beginning of the transition from “Boomers” to “Xers.” I’m glad my parents had me in 1965 instead of 1964, where I’d spend my life arguing (maybe with myself) that I’m not a boomer.

A millennial friend of mine didn’t know anything about Generation X, so I sent her a copy of the book. I suppose I was teasing her too much about being a millennial, which was just me mostly being a typical ironic Gen X slacker.

I reread Generation X a few weeks ago, and it held up. The definitions in the margins made me flash back to phrases we used in my early 20s. Douglas Copeland’s brilliant imagination shines throughout. And, at 55, I’ve become comfortable saying “Kids today …” which is what I’m sure my parents (and the boomers) said about me and my generation.

This week sucked emotionally. The Boulder shooting on Monday took the wind completely out of Amy and me. It’s Friday, and I’m winding down for the weekend. Work was intense, so I didn’t have a lot of time to feel my feelings. We were in the car for a while this morning driving back to Boulder from Aspen, so I let myself settle into how I felt. Now that I’m not shocked anymore, the best word I can come up with is “sad.” Very sad.

Grunge is my music. Pessimism abounds in Gen Xers. I’ve adopted the mantle of “paranoid optimist,” which I first heard from Madeleine Albright. At 55, I prefer to be happy and optimistic, but underneath it all is cynicism.

I’m glad to be back in Boulder.

Thanks to everyone who sent a note to me in the past few days about the shooting in Boulder on Monday.

10 people murdered in a city of 100,000 people, in a place that I love where I’ve lived since 1995, is an extremely difficult thing for me to process.

On Monday, Amy and I were shocked. On Tuesday, we were both shaken and stunned. The emotions really hit us both on Wednesday.

Last night I went for a long run with some of my favorite childhood music (Pink Floyd). I listened to Dark Side of the Moon, The Final Cut, and half of The Wall before getting back home. I sat in the hot tub for 30 minutes and then went to bed. I woke up this morning feeling a little calmer but still unsettled.

Some of you have asked if there’s anything you can do. The Boulder County Crisis Fund is the best choice. The Community Foundation: Boulder County is partnering with others to support the victims, their families, and our community in dealing with and processing the March 22 supermarket shooting in Boulder. Some of the partners include:

9News, the City of Boulder, The Daily Camera, iHeartMedia, The Colorado Healing Fund, Community First Foundation, The Denver Foundation, Longmont Community Foundation, Rose Community Foundation, Boulder Mennonite Church, Community Church of Lyons, Congregation Bonai Shalom, Congregation Har Hashem, First Congregational Church, First UMC of Lafayette, Islamic Center of Boulder and Westview Church.

If you are up for making a financial contribution to help people out in the crisis, please make a donation to the Boulder County Crisis Fund.

• #Venture Capital
• #mahendra ramsinghani

Today’s book recommendation, for anyone interested in venture capital, is The Business of Venture Capital: The Art of Raising a Fund, Structuring Investments, Portfolio Management, and Exits by Mahendra Ramsinghani.

A decade ago, I got a cold email from Mahendra. He was investing in Detroit and eager to write a book about the art and science of venture capital. At the time, Jason and I were just finishing up the 1st edition of Venture Deals: Be Smarter Than Your Lawyer And Venture Capitalist and I was enthusiastic about helping anyone else working on a book that demystified venture capital investing.

I immediately introduced Mahendra to a bunch of Foundry Group LPs, partners, and entrepreneurs. He made progress quickly, and I fondly remember the first edition with the green cover.

Mahendra and I kept in touch. During a book tour for the 1st Edition of Venture Deals, Jason and I visited the University of Michigan. Mahendra cornered me in a hallway and pitched the idea of doing a book together around how a board of directors works at a startup. A few months later, we started working on it.

Startup Boards: Getting the Most Out of Your Board of Directors was released in 2014. Soon thereafter, Mahendra started to work on the second edition of the Business of Venture Capital. Given our recent collaboration, he asked me to write the foreword for the second edition, which was an easy yes for me. The 2nd edition had a blue sky cover and was also released in 2014. In the foreword, I wrote that “VC is a business where each investment teaches you something new – the book provides only a basic framework but each one has the ability to carve a different path in this universe.”

Mahendra recently came out with the 3rd edition of The Business of Venture Capital: The Art of Raising a Fund, Structuring Investments, Portfolio Management, and Exits. It’s now 500 pages and includes much-needed frameworks for culture, diversity, and values that are timely topics when we look at the challenges we have seen in venture capital around gender, race, diversity, and sexual abuse. This time the foreword is from Scott Kapor of A16Z who in 2019 wrote an excellent book on venture capital titled Secrets of Sand Hill Road: Venture Capital and How to Get It.

If you have suggestions for the fourth edition, please reach Mahendra at mr “at’ secureoctane.com.

• #Boulder

A mass shooting happened at a King Soopers on Table Mesa in Boulder Monday afternoon.

Amy and I are safe. So are our friends and family. But 10 people in Boulder, including one police officer, are dead.

The King Soopers was the one that Amy and I shopped at from 1996 – 2014 when we lived in Eldorado Canyon. I’ve been there hundreds of times. It was at the six-mile mark of my ten-mile run to town. Many friends live within minutes of it, including my brother and his family, my partner Chris Moody and his family, Amy’s current assistant Rebecca and her family, and Amy’s prior long-time assistant Naomi and her family.

Amy’s nephew Jason had gotten his groceries there fifteen minutes earlier. A friend of a board member worked there and snuck out the back. So did a neighbor of my brothers.

Whenever something tragic happens, the quick rationalization is “Well, at least that won’t happen here.” Boulder has always felt incredibly safe to me. I won’t even read a popular crime/thriller novelist whose books are set in Boulder because I don’t want anything to damage my calm.

My calm is very damaged right now. I was going to head out for a long run at the end of the day but couldn’t leave the house. I just sat with Amy, while she doom scrolled through Twitter and texted with friends and family. I ate something but don’t remember what it was. Upon reflection, that sounds a little like a shock response to me.

Last night, an endless set of IMs and emails rolled in checking on us. That calmed my nerves a little, to be loved, but I kept realizing how fragile and arbitrary things are. The phrase “the victims are in our thoughts and prayers” is nice, but it seems so inadequate. We find ourselves in 2021, still in a pandemic, with extraordinary heath, financial, and emotional stress everywhere, and then this.

Boulder has been a special place for me and Amy since we moved here in 1995. Evil showed up in our town yesterday.

• #give first podcast
• #maelle gavet

David Cohen and I recently interviewed Maëlle Gavet, Techstars new CEO. It’s a great way to get to know a little more about her in under 30 minutes.

I met Maëlle about a week before I talked to her for the first time by reading her book Trampled by Unicorns: Big Tech’s Empathy Problem and How to Fix It. I knew I’d like her before we talked, and after almost two months of working with her, I’m psyched she’s at the helm of Techstars.

Amy and I have been collecting contemporary art since we started dating in 1990. Every morning at our place in Aspen, over morning coffee, we get to enjoy this amazing piece by Julie Maren.

When I wrote the original post, I got a short email from Phi Pham.

I hope you’ll be mindful of collecting art from Black and POC artists too! 

My response was:

We have some, but not mindfully. For example, we are a huge collector of Emilio Lobato.

It’s a good reminder.

Do you have any recommendations for artists in the Western US who are Black or POC?

A few months later, I got another email from Phil with an amazing list that was compiled by Phil and his sister with help from Hannah Leathers and Solomon “Solo” Muhammad,

Phil, Hannah, and Solo – thanks for the great list.

• #stoicism

I no longer subscribe to many daily email newsletters, but I’ve kept a few. My favorite to wake up to is Ryan Holiday’s The Daily Stoic.

Today’s headline was It’s Possible to Tune These Things Out but it linked to an older post titled The True Power Behind Stoic “Indifference”.

At morning coffee a while ago, Amy and I had a long conversation about the phrase “I don’t care.” I struggled to explain what I was trying to say and how it was often misunderstood when I said it. Through her reaction and feedback, she helped me better understand what people heard when I said “I don’t care.”

I tried shifting to the phrase “I’m indifferent” instead of “I don’t care.” I continued to feel that I was being misunderstood when I said this. I’d often provide strengths and weaknesses of each option presented but then end with “I’m indifferent.” I knew that this was confusing to some, but I didn’t know why until I read The True Power Behind Stoic “Indifference”.

Of all the loaded words in Stoic philosophy, “indifferent” is one of the most provocative. Marcus Aurelius, Seneca, and Epictetus each tell us that the Stoic is indifferent to external things, indifferent to wealth, indifferent to pain, indifferent to winning, indifferent to hope and dreams and everything else. You hear it enough times and it starts to sound like these people don’t care about anything. Especially since the modern definition of the word means precisely that. But this is a dangerous misreading.

Recently, I got feedback from several people that I was profoundly unhelpful in a particular situation by saying, “I’m indifferent.” I thought about it on a run, which is unusual for me as I rarely focus on one thing during a run but prefer to let my brain go all over the place. In this particular situation, my brain seemed to lock down on the dissonance around this phrase.

The situation in question had two paths: A and B. I had a modest preference for A, but I was good with either A and B. I had explained this, but when asked which I preferred, I said, “I’m indifferent.”

After my run, I explained this more clearly, reiterating that I had a modest preference for A but was good with either A or B. Instead of “indifference,” I stated that I was “tranquil.” After even more reflection, I think a better concept would have been “equanimity.”

Back to the The True Power Behind Stoic “Indifference”.

The Stoics were not indifferent in that sense at all, it’s that they were good either way. It’s not that they didn’t care, it’s that they were good either way. Does that make sense? The point was to be strong enough that there wasn’t a need to need things to go in a particular direction. Seneca for his part would say that obviously it’s better to be rich than poor, tall than short, but the Stoic was indifferent when fate actually dealt out its hand on the matter. Because the Stoic was strong enough to make good of it—whatever it was.

Boom. After reading this, I got the disconnect people were having, which was reinforced by the contemporary view of equating “I’m indifferent” to “I don’t care,” which is very different from “I’m good either way.”

Think of that today, that it’s not about apathy or even a lack of expectation. It’s simply the quiet strength of not needing a preference, because you’re that strong.

Ryan – thanks again for helping me understand myself a little better.

• #stan feld
• #dave jilk

Two of my favorite men on planet Earth have birthdays today.

Happy birthday Dad.

Happy birthday Dave.

I’ve learned an incredible amount from each of you. And, given all the time the three of us have spent together, from both of you.

One of the best things I’ve learned from each of you is a love of wide-open physical spaces. Dad – I’m so glad you and Mom created Woodcreek Ranch.

Dave – thank you for all the 14ers. I hope to climb many more with you.

Even though we’ve spent a lot of time together as a threesome, one, in particular, stands out. We had a Feld Technologies board retreat in the fall of 1987. I remember the date because it was during the Bork confirmation hearing. We spent the time in New Hampshire, drove around looking at leaves, and talking about what Feld Technologies could become now that the summer of 1987, which was full of missteps, was over. We did a huge reset that weekend on what we were doing, which set Feld Technologies on a path where it was profitable every month for the rest of its life. The other path could have been the death of the company, so it remains a potent and formative moment for me.

Happy birthday to you both!

• #SPAC

Like many people, I’m currently deep in SPACland. I’ve been writing privately about it a lot but have now crossed over into a zone where I feel like writing more publicly about it.

When Jason and I wrote the first edition Venture Deals in 2011, we built off a series of 30+ blog posts we wrote in 2005 about Term Sheets. It’s fun to explore them for historical reference since Jack Bauer plays a major part in the posts.

While these posts were the seed for what is now a book (Venture Deals: Be Smarter Than Your Lawyer And Venture Capitalist), it was also a way for us to think through all the elements of a VC financing, back at a time when there was enormous opacity about how these worked, along with massive information asymmetry between people who did them all the time (e.g., us) and the entrepreneur, who did a few of these over her lifetime.

While the web is a much noisier place in 2021 than it was in 2005, the opacity and information asymmetry around SPACs are remarkably similar to what existed 16 years ago around venture deals.

The cliche “everyone’s an expert, but no one knows anything” applies. Yes, there are some experts, but not that many. And the amount of misinformation, misperception, opacity, and information asymmetry is enormous.

As I continue to write privately, I’m going to start writing more publicly. And I encourage comments, feedback, and corrections.

While there is much debate about SPACs, I believe they are a long-term part of the capital stack. They are evolving rapidly, which is part of what is so interesting about them, at least to me.