Author Archives: Ben Casnocha

Why Do So Many VCs Say They’re Introverted?

Posted inBusiness2 Comments on Why Do So Many VCs Say They’re Introverted?

I wrote a tweet a couple months ago:

Who knew that introversion/extroversion was such a hot topic?! It generated a lot of replies from people I respect. Here’s one:

And this:

And this:

The three replies above, as I understand them, all make a similar definitional point: A person can be introverted and still be highly social; it’s just that the social interactions drain them of energy and they need to re-charge alone afterwards. Fair enough and I appreciated the clarification.

Now, if we accept the premise that VC is an extremely social enterprise, does this mean that VCs who consider themselves introverts by this definition — capable of being highly social — do these VCs find themselves drained of energy at the end of most days?

Mike Arrington replied and said yes:

Brad Feld has also written about how he is “fundamentally an introvert” and, similar to Mike, the venture work stream drains him completely once a year:

About once a year I completely use up my extrovert capacity.  I drain it completely to zero. … The last sixty days have been awesome but extremely intense. My ordinarily full days had the Do More Faster book tour layered on top along with a bunch of other public appearances, interviews, speaking engagements, and events.  About two weeks ago I started feeling a fatigue that I couldn’t get in front of and the last two weeks pushed me over the edge.

For those for whom this is true, who am I to judge their career decisions? It’s hard to perfectly match career to personality; no job will ever be 100% perfect. And this dimension of social/energy is just one consideration on whether VC is the right fit. Both Mike and Brad have been extremely successful in tech and venture capital. I don’t know Mike personally, but I do know Brad, and I know that on balance Brad loves what he does. The VC job, on balance, appears to be a great fit for him.

My point is that, in general, most of the VCs I know are highly extroverted. And this would be logical, because people tend to gravitate to jobs where a primary piece of the job description energizes them, not drains them. So with respect to VCs and introversion/extroversion, I believe there are not as many Mike Arringtons out there as we may think — i.e., people who are “painfully introverted” who do the job well even though it leaves them “exhausted.”

Among this crop of extroverted VCs I know, some still call themselves introverted, which perplexes me. They’re highly social and do not seem — at least to me — not very drained by all the socializing. Yet they nonetheless refer to themselves as introverted.

What’s going on?

First, as mentioned in my original tweet, the “introvert” label has come to be associated with adjectives like thoughtful, intellectual, wise, evolved. Introversion may be a higher status description than extroversion. Extroversion is associated with smarmy networkers. I don’t read many extroverts declaring themselves proud extroverts in public. I do routinely read about people proclaiming their introversion.

I’m fascinated by the evolution of terms and connotations. As “networker” has evolved from being a cutting edge business skill in the Dale Carnegie era to now being term to describe the worst excess of that original skill, so too has “introvert” evolved from formerly describing a shy, awkward minority to now being a broad term that connotes a refined, thoughtful, intellectual air about life that seemingly a majority of people now claim.

Second, the comparison set. VCs in general are among the most extroverted humans on the planet. They (we) are professional meeting-takers, emailers, phone callers, conference attenders, deal makers with others humans. (To be sure, I appreciated the point in the reply tweet embedded above that 1:1 founder meetings is a different type of “social” activity than big group meetings, and VCs do a lot of 1:1 small meetings.)

When you work in venture, you’re comparing yourself to other VCs. I know VCs who take 7-8 calls/meetings a day and then a long dinner, and they do this 4 days a week. But, they look around and see another VC who does all of the above PLUS post-dinner drinks followed by an all-weekend conference, and the first VC thinks, “Gosh, I’m an introvert compared to that guy.” It’s LeBron James comparing himself to Steph Curry and concluding, “I’m not a very good three point shooter,” when LeBron’s 3 is better than 99% of all humans’ 3 point shot. So, it’s a comparison / frame of reference issue.

So, to recap my thinking here:

  • You can be introverted and be highly social. If this is the case, you probably find those social interactions draining. But you can do it successfully.
  • Some VCs are introverted, successful, and are simply drained by the social part of the job.
  • The vast majority of VCs in my experience are highly extroverted, which makes sense in terms of trying to align career with personality.
  • Many more VCs describe themselves as “introversion” than who probably are. Perhaps because of status considerations. Perhaps because of their comparison set.

Thanks to everyone who replied to the tweet and emailed me about it. Definitely pushed my thinking. Happy to hear any additional feedback on these points in the comments.

Comment

Village Global: Hiring, Network Catalyst, Founder Retreat

Posted inVillage GlobalLeave a comment on Village Global: Hiring, Network Catalyst, Founder Retreat

A few Village Global updates:

– We’re hiring a full time GM of Network based in San Francisco. Job description here. Wonderful opportunity for someone looking to break into VC in a non-investing role. A good fit for supreme operators who also understand the startup/venture game. Former bankers, consultants, startup CEOs/COOs, or VC ops people could all be a good fit.

– We run an accelerator program called Network Catalyst. Think Y Combinator, but more personalized, more intimate, more about connections than content. Application deadline was  couple days ago but if you’d like to be considered, email me.

– We hosted an awesome retreat for 80 of our founders near Yosemite last summer. Here’s a video recap of what went down. It highlights some of what makes the Village community special:

Comment

How I Officiated a Wedding

Posted inRelationshipsLeave a comment on How I Officiated a Wedding

I was honored to officiate a wedding recently for some friends.

As I prepared for the duties, I reflected on the number of weddings I’ve attended where, by the end of all the festivities, I couldn’t answer two basic questions:

  1. Who is the other person in the marriage? I know one person in the partnership really well, presumably. What’s the life story of the guy/gal who’s marrying my friend?
  2. Why are these two people getting married to each other? What’s the essence of their dynamic?

Based on this, I structured my remarks to make sure everyone in attendance could at least nominally answer both questions by the end of it. The three-part structure was:

  1. Describe the bride and groom each as individuals: their childhood, basic attributes/personality, professional activities. [This required interviewing the bride and groom beforehand and collecting stories/anecdotes/nuggets.]
  2. Describe who they are as a unit: why they’re marrying each other, how they’re similar (the hallmark of friendship), how they complement each other (the hallmark of partnerships).
  3. Look toward the future and offer some general perspectives on marriage, love, and life.

There were no other speakers or readings during the ceremony, so I ended up speaking for about 18-20 mins and could cover all these points. It worked pretty well.

Of course, no matter what you plan to say, if the audience can’t hear you — literally — it doesn’t matter. I’ve witnessed my fair share of wedding ceremonies where the house A/V doesn’t work, or more commonly, the people speaking don’t know how to use or hold a microphone. With handheld mics, 99% of people hold the mic like an ice cream cone instead of a toothbrush, and so the audio quality oscillates. (Hold it like a toothbrush very close to your lips!) A lav mic is almost always better for this reason but even still it can poorly positioned on the shirt such that as people turn their head when they speak, you start missing words. Anyway, in this ceremony, the mic situation worked fine, thank the Lord!

Below is an excerpt of my closing remarks from my officiating.

We know there will be moments of joy for you both, we just don’t know what, when, or how. Will they occur at predictable intervals, such as at the birth of a child or the realization of a huge professional goal? Or will joy sneak up on you, will it happen when the two of you are going on one of your regular walks around New York, and for whatever reason you see something that reminds you both of an inside joke and you both laugh uncontrollably?

A spiritual teacher once taught me: Don’t miss the joy when it comes! Stay present with the joy as you experience it, he said. He said to tell yourself, “Oh, this is what joy feels like.” “This is what it’s like when I feel happy.” “This is what it feels like to see a beautiful bouquet of flowers.” “This is what it feels like to experience a beautiful sunset.”  We might even look around the room right now, at all our friends and family, and take a second to think to ourselves: This is what love feels like.

In addition to the joy, we also know there will be moments of serious hardship ahead, we just don’t know what, when, or how. Will there be a wave of expected grief at the death of a good friend? Or will malaise sneak up on you guys in a less expected moment, perhaps a pang of doubt on a cloudy day in late fall, doubt about whether you’re doing the right thing in your career or whether – god forbid – you married the right person.

Marriage, in my experience, brings more joy, and sometimes more pain, than if you were living life on your own. It adds dynamism and love and struggle. Amazing highs and sometimes really challenging lows.

The natural human thing to do is to try to hold onto the joyful moments, and avoid the unhappy moments.

But that’s impossible, because everything changes. In fact, someone once summarized the entire cannon of Buddhism in those two words: everything changes. The Buddha argued that everything in life is impermanent.

There have been so many joyful moments in your relationship so far. [Personal details]

So there have been some amazing moments. They’re now in the past. Marriage will be filled with millions more of these impermanent moments. The Buddha taught: Stay awake to the moments of joy that arise from being married to each other, and feel them.  Know that they will pass.

Also be aware of the moments of dissatisfaction that arise from being married to each other. Know that they will pass.

And do what you can to have more good moments than bad ones. That is what I wish for the two of you.

Photo Source: A Perfect Match Photography
Comment

Book Review: An American Marriage

Posted inBooksLeave a comment on Book Review: An American Marriage

“Everyone who reads novels has read An American Marriage,” she told me. I guess I’m behind, I thought.

So I downloaded the book on my Kindle, and got hooked. When I finished the book a couple weeks later, I stared off into the distance for about a full minute. Which I guess in the sign that something really sunk in.

It’s a wonderful story, compellingly told from different viewpoints. The primary theme is marriage and its discontents (and contents). Other themes include criminal justice and wrongful imprisonment (the main character Roy, wrongfully accused of rape) and the colors of the American South. The writing is straightforward but often beautiful.

A good chunk of the book is told via letters, sent from prison, between husband and wife. It’s an incredibly effective technique for conveying the intimacy of love — and doubt.

The final letter contains my favorite line: “My prayer for you is for peace, which is something you have to make. You can’t just have it.”

Other highlighted sentences below. Highly recommended.

Still, the truth is that there was nothing extra. If my childhood were a sandwich, there would be no meat hanging off the bread. We had what we needed and nothing more.

It was a wonderful feeling to be grown and yet young. To be married but not settled. To be tied down yet free.

“November 17,” I said before she could complete her thought. Other couples use safe words to call a time-out from rough sex, but we used it as a time-out from rough words. If either of us says “November 17,” the anniversary of our first date, then all conversation must cease for fifteen minutes. I pulled the trigger because I knew that if she said one more word about my mama, one of us would say something that we couldn’t come back from. Celestial threw up her hands. “Fine. Fifteen minutes.”

One of the hurdles of adulthood is when holidays become measuring sticks against which you always fall short. For children, Thanksgiving is about turkey and Christmas is about presents. Grown up, you learn that all holidays are about family, and few can win there.

But a man who is a father to a daughter is different from one who is a father to a son. One is the left shoe and the other is the right. They are the same but not interchangeable.

As I watched her walk away, I made note of everything about her that I didn’t admire. I ignored the devotion that she wore like a cape, I paid no heed of her strength or hardworking beauty. I sat there thinking of all I didn’t love about her, too angry to even say good-bye.

Comment

Smart Is Not Enough: What Marc Benioff Taught Me When I Was 15 Years Old

Posted inCareers2 Comments on Smart Is Not Enough: What Marc Benioff Taught Me When I Was 15 Years Old

Many years ago, I cold-emailed Salesforce founder/CEO Marc Benioff. I was 15 years old and starting a CRM software company like his. Would he meet to give me some advice? I wasn’t the only one inspired by Marc’s vision of the “end of software” at the time. But I may have been one of a smaller group who was especially inspired by the fact that Marc had started companies as a teenager back in his day.

To my surprise, he replied, we met for breakfast, and it kicked off a series of meals that we shared over several years. He eventually wrote the foreword to my first book.

At one of our early breakfasts, Marc told me something I’ve never forgotten. I remember the moment exactly. I was wearing a suit and tie, which in hindsight was kind of crazy. (“I hope you don’t normally wear a suit and tie when you go to school,” he said with a laugh.) He ordered pancakes. He had been telling me about swimming with dolphins in Hawaii, what he learned from Larry Ellison, and riffs on spirituality.

He then told me: “Ben, people in Silicon Valley are ridiculously smart. Super, super smart. You’re not going to be able to out-smart people. You have to figure out how to win in some other way.”

I was not lacking in self-regard for my own intelligence at the time. But when he said it, I knew immediately it was true. I may be generally smart but general smarts is like vanilla ice cream. Vanilla ice cream is a fine dessert but it’s not going to win a chef any culinary awards. And IQ is IQ. No amount of study would allow me to compete head-to-head in an IQ contest with the highest IQ people in the tech industry. If you regularly feel like you’re the highest IQ person in the room, you’re hanging out in the wrong rooms. The tech industry may not be as intellectually intense as academic disciplines like chemistry but there are plenty of rooms with off-the-charts IQ people in them, and those are the rooms you want to be in — even if they make you feel a bit inferior at times.

As I contemplated Marc’s comment in the months afterwards, my first plan was that I could out-work everyone in order to be successful. I may not be smarter than everyone else, but surely I could out-work them, right? Then I realized that there were people who could work harder than me, and already were. Damn those people who only need 4 hours of sleep a night!

Marc’s advice is not obvious to a lot of people. These days I still meet many super smart and super hard working people in business who, deep down, are mystified as to why they haven’t been more successful in their careers. They really believe their raw intelligence and/or their work ethic should be enough to carry the day.

Anyway, in the years after that breakfast, in my early 20’s, I came upon two deeper insights that ultimately are how I answer and incorporate Marc’s advice to me.

First, I could get good at facilitating the intelligences of other smart people. You don’t have to be smarter than someone in order to enable that person to be all they can be. Most business efforts involve teams — multiple smart people interacting with each other. If you can develop the ability to work with different kinds of smart people, to bring them together, to facilitate all the IQ points sloshing about, you can be a really high-impact player. In fact, I’d argue this is what great CEOs do well. They’re not the smartest person in the company. But they get all the other smart people to play well together. Arguably, that’s the most important job of all on a team.

Some years ago, my friend Auren Hoffman emailed me and said there had been a cancellation at an event he was hosting in New Orleans and asked if I wanted to take the open spot. I said yes. As I reviewed the list of other attendees, it was obvious that I was the B-list invite to an event filled with other A-listers. I was excited but a bit nervous. Then, a few days before the event, Auren asked me to moderate a 90 minute session with 15 accomplished people at the event. At first I thought he had sent the email to the wrong person; I think I was 17 years old at the time. The people in my session were all much smarter and more experienced than me. But I accepted the task, and I did fine. I did good, even. And it emboldened me with the confidence that I could credibly be a participant in a large meeting even if on paper I wasn’t the smartest or most experienced person.

The second insight I internalized in the years after that breakfast with Marc Benioff was that I could get good at combining multiple skills in unique combinations. Scott Adams once wrote that to be successful you need to either be the very best in one field or the top 25% of skill in multiple fields. In other words, if you’re not world class at something but you’re really good at a couple things and the combination of those two skills produces a valued offering in the market, you can be successful. Example: You can either be one of the top pianists in the world and succeed through sheer singular talent, or be a really, really good pianist (if not world-class) and also be really, really good at marketing (or some other skill), combine the two really-good skills, and success will follow.

Given my curiosity and knack for synthesis, I saw a path for me that would involve getting really good a couple things and combining them in interestingly unique ways (versus becoming solely obsessed with one skill area). I could take basic intelligence and work ethic, and layer on top of that very strong — even if not truly world-class — abilities in entrepreneurship and written / oral communication, for example, and that could produce some interesting career opportunities. (That specific skill combination helped me be a complementary partner to Reid Hoffman over the four years I worked for him.) In the years since then, I’ve continued to hone different skills that in combination in an attempt to develop a unique competitive advantage in whatever market I’m playing in.

Like a lot of important wisdom, Marc’s comment to me at breakfast in San Francisco all those years ago sounded simple. The depth of its truth took years for me to appreciate.

Comment