Posts from life lessons

Fun Friday: Teaching Empathy

This is a serious topic, brought up by reggiedog in yesterday’s comment thread, but maybe we can have some fun with it today.

I agree with reggiedog that teaching empathy to children is necessary if you want to produce happy and healthy adults. We are fortunate that our kids’ school was damn good at that and we certainly never missed an opportunity to point out how their actions made others feel.

The Gotham Gal spent much of her high school years coaching kids sports. She had a whistle around her neck and pretty much every form of athletic equipment in the back of her car. And we encouraged our kids to do the same. Each of them coached middle school basketball when they were in high school. Looking back on that, I think coaching/teaching at a relatively young age is a great way to teach empathy. You learn how to deal with challenging situations and the emotions that come with them up close and personally.

Taking this to another level, teaching in general is a great way to learn to help others and feel the joy that comes from that. If you can put your kids in situations where they are helping others, you are likely to teach them empathy for others, which as reggiedog points out is a badly needed skill in this day and age.

I’m curious to hear from others in the comments how they have approached this challenge as a parent.

Forgive and Forget

My partner Albert has long been arguing on his blog (which you should be reading) that technology is bringing massive changes to society and we are going to have to change the way we think about things in reaction to these changes. One of those areas is privacy and the “post privacy world” that we are entering.

Last week he wrote this about the Ashley Madison hack and argued that society needs to be accepting of and forgiving of transgressions like using a website to arrange extramarital affairs. When I read that post, I thought “oh my, that’s pretty out there.” Mind you, I don’t disagree with Albert’s point at all, I just thought most people aren’t going to see it that way.

So I was pleasantly surprised this morning to see Farhad Manjoo make essentially the same argument in the New York Times.

Farhad quotes a security expert at the end of his post:

True online security is not just defending against compromise, it’s operating under the assumption that compromise will happen.

And of course that is true for the technologists who work in the teams that strive to keep our systems secure. But if you, like Albert and Farhad did, take that point to its logical conclusion, then all of us will have are in for having our deepest darkest secrets outed at some point. So let’s hope society becomes more forgiving over time. It’s going to have to.

Prime Numbers and the Prime of Life

I turn 54 today

54 is not prime

53 is

I enjoyed 53

I expect to enjoy 54 as well

Numbers are fun if you let them be

But numbers aren’t really that important

What is important is enjoying life

And I plan to do that today and every day

Fundraising Tip: Don’t Send The Same Email To Two Partners At The Same VC Firm

Over the weekend I got an email from an entrepreneur wanting to come pitch his startup to USV. He copied my partner Andy on the email.

I immediately thought “I’m going to let Andy reply to this one.” But a couple days later the email still was sitting there in my inbox unreplied to. So then I thought “Andy is probably waiting for me to reply to this.”

Finally I shot Andy an email and we compared notes on it and then I replied to the email.

But it doesn’t always work out like that. I’ve seen a similar situation end with neither partner replying to the email and it goes unresponded to.

I call this situation email hot potato and entrepreneurs should avoid it by sending an email to only one partner at a VC firm, not two or more.

A good alternative is to send an email to one partner and copying an analyst at the firm as well. The analysts are the most diligent people in a VC firm about staying on top of inbound deal flow and they will often step in and reply to an email that a partner has missed or forgotten about.

The important thing here is to avoid confusing who has the responsibility to reply to the email by putting multiple responsible parties on it. While it would seem that it would increase the likelihood of getting a reply, it actually reduces it.

Video Of The Week: Gotham Gal at Columbia

Last month the Gotham Gal gave a keynote at the Columbia University’s #StartupColumbia Festival. Here it is.

It’s also our 28th wedding anniversary today. We are celebrating it in Istanbul. Off to the Grand Bazaar to work on our negotiating skills.

The Blank Screen

I was at dinner last night with some entrepreneurs and VCs in Berlin and we got talking about my ritual of blogging every day. I told them that many days I stare at the blank screen and think “ugh, what am I going to write about today.”

blank screen 2

They asked if there was any correlation to knowing what I am going to write about and the quality of the post. I told them that I don’t think so. The best posts come out in real time and often they start with me staring at the blank screen. Same with the worst posts.

Posting every day isn’t easy for a host of reasons but for me the hardest is that much of what I work on every day is off limits. I wake up thinking about a drama unfolding in one of our portfolio companies and I can’t blog about that. I wake up thinking about a new product one of our portfolio companies is going to launch and I can’t blog about that. I wake up thinking about a neat company we just met and I mostly can’t blog about that.

So on a typical morning, I run through four or five ideas, tossing each out for a variety of reasons, before settling on something, and then I start writing and I go from there. I enjoy the real time nature of this approach to writing. I often don’t know what the gist of the post is going to be until I write that last line and hit publish.

Sometimes this process produces great insights for me and possibly others. Sometimes it produces garbage. But I’ve come to realize that the daily post, and its quality or lack thereof, is not really the thing. It is the ritual, the practice, the frequency, the habit, and the discipline that matters most to me. And, I would suspect, the same is true of the readers and commenters who frequent this blog.

Mother’s Day

It’s mother’s day and I find myself thinking about my girls, who are not mothers at this time in their lives. And yet they both have been working on projects involving motherhood this spring.

Emily wrote her bachelors thesis on the challenges of balancing motherhood and careers. She called it “Life Sequencing: A Viable Solution To Work-Life Conflict For High-Achieving Women” and it was a thorough investigation of the challenges of balancing work life issues and some possible answers.

Jessica has been making an Oculus Rift based immersive experience for an art show called Dear Mama where young artists are showing work  “in honor of Mother/s, mothering, motherhood: incl. all the shapes that role may take.”

Each, in their own way, are honoring their mother with their work and it is very satisfying for me to see that. Joanne is many things, but first and foremost she is a wonderful wife and mother, and it pleases me to no end to see her fine work reflected in our girls.

I’m also fortunate to have a loving mother of my own. I plan to call her this morning, then head to brunch with Joanne and Jessica, then to Jessica’s show to bask in art about motherhood.

Happy mother’s day everyone.


For those who are on to the theme of my posts this week, Dedication will seem like an obvious choice to finish with.

I am dedicated to my family, my work, our portfolio, this blog, the Knicks, Mets, Jets, and a host of other things that require daily dedication. This week I was dedicated to the notion that all posts would start with D and end with tion. And I followed through and finished it off.

d ...

That’s what dedication is.

Dedication is also a testimony of affection or respect. At the start of many yoga classes, you are asked to dedicate your practice to something or someone. I mostly pick my kids, whichever I think needs the dedication that day, and sometimes the Gotham Gal too. I’m dedicating this blog post to my entire family on the eve of Passover.

Happy Pesach Everyone.


I was just doing some work on a personal finance thing. I completed one part of the job and went to my email to finish it and saw another email at the top of my inbox about something else, I clicked on that email, started dealing with that, and almost forgot to finish off the personal finance thing. This happens all the time to me. I am so easily distracted.

I got rid of my desk phone in my USV office several years ago because I cannot sit in front of my computer when I am on a call in my office. I have to do my calls on my cell phone and walk around my office, look out the window, or something else or else I will get distracted.

I struggle with distraction big time. It’s not just the attention deficit kind of distraction I just talked about. Distraction crops up in other parts of my life. The Gotham Gal is constantly on me about being distracted in conversations with her. And she’s right to be on my case about that. If she was not, I would be even worse.

I’ve been working on this for much of my adult life. I’ve made progress but the distraction urge still is very much front and center in my psyche and my unconscious. I suspect this is something I will work on all my life.

Some things that have helped me are the aforementioned coaching by the Gotham Gal, yoga, meditation (which I have not yet made a staple in my life but I’m working on that), and a general self awareness of the problem and the need to take as many distractions away from me as possible when focus is required.

I know that I will get a lot of suggestions in the comments for software tools, workflow routines, and other self improvement techniques that have helped others deal with this problem. I will thank everyone in advance for those, but I will also say that I’ve tried all of that before. And tools and techniques haven’t really worked for me. I have found getting into the root causes and developing self awareness and more serenity in my life has worked a lot better.

But I’m still pretty bad. If you find yourself on the phone with me and I sound distracted, I probably am. And please feel free to call me out on it. I would appreciate that.

Reblog: VC Cliché of the Week

Back in the early days of this blog I had a series called VC Cliche Of The Week. I’m not sure how long I ran it but I did eventually run out of material and phased it out. In continuation of yesterday’s good vibes and with yet another shoutout to Bliss, here’s a reblog of one from March 2006:


The father of this weekly series, the guy who taught me at least half of the cliches I know, is a guy named Bliss McCrum. He and his partner Milt Pappas taught me the venture capital business from 1986 to 1996 when I worked with them at their firm, Euclid Partners.

One of my favorite cliches from Bliss is a rising tide lifts all boats.

Whenever things seemed too good at a portfolio company, in the stock market, the economy, or somewhere else, Bliss would quip, “well you know that a rising tide lifts all boats“.

It was his way of saying “don’t mistake a good market for a good business”.  The insinuation was always that the tide would come back in and so would the boats.  And you had to be prepared to make things work in tough times as well as good times.

And we are in good times in the venture business, the internet business, and for the most part, the US economy.  Consumer confidence hasn’t been this strong since before the Iraq war.  The Fed has raised rates 15 times and may not be done, signalling that the economy remains stronger than they’d like it. Venture money is flowing freely in Silicon Valley and China and in many parts of the developed or developing world.  Advertising dollars continue to move from offline media to online media and that is one rising tide that is certainly lifting all boats.

But we know these good times will come to an end at some point.  Are we in 1998 as Caterina suggests and have another year or two before the good times end?  Who knows?  I don’t expect this run of good times to play out like the last one anyway.

The best we can do is prepare our companies to withstand a business environment that is less friendly.  Companies need a business model, they need a seasoned and well constructed team, and they need patient and experienced financial partners.  With these ingredients, hard work, and some luck, you can survive a downturn.

Some of the best companies I’ve ever worked with were funded at the height of the last bubble and they are doing great now.  So it doesn’t really matter when you start a company, but it does matter that you can make it through tough times.  Because right now we have a rising tide that is lifting all boats and that won’t last forever.