Musings of a VC in NYC

Fifty

The Gotham Gal asked me this morning "how does it feel to be 50?" I said "it feels good. another accomplishment."

It's only a few waking hours into my 50s but so far it feels great. I've never been more content with my place in the world, never felt better, and never had so much I want to do.

A friend gave me a book about turning 50, I've been trying to read it, but it's filled with all these "getting old" jokes and they aren't making me laugh. They don't resonate with me.

What does resonate with me is friends and family. The past week has been fantastic in that regard. This weekend my mom, dad, and brothers and their families are spending the weekend with us. Good times with friends and family at the end of the summer has always marked my birthday and this year has been particularly great in that way.

I'm going to start celebrating turning 50 by going out and getting the makings of breakfast with my brother. But before I do that, let me take one more moment to encourage everyone out there to consider a contribution to the Fifty For Fifty campaign we are doing via Donors Choose. We are getting really close, we passed $43,000 yesterday. Please consider contributing if you haven't done so yet.

Forced Email Bankruptcy

Sometime yesterday morning between 5am and 7am all the mail in my inbox that had come in but had not been responded to in the past ten days disappeared. It appears that it is in my archive (along with a ton of mail that came in the past ten days that I have responded to and archived). Somehow I auto archived ten days of mail in my inbox.

In any case, I am not going to go through the laborious task of fishing out all that unresponded to email out of my archive and put it back in my inbox. So if you sent me an email in the past ten days and I didn't respond, there is a good chance your mail got auto archived. I'm sorry about that. Feel free to send it again.

The good news is for about three minutes I was at inbox zero. It felt good.

Subconscious Information Processing

It's fathers day and I thought I'd tell a story about my dad and something he taught me a long time ago. I was in middle school and I had a school project due the next day and it came up at dinner that I had not done the project. My dad made me stay up very late that night until I had completed it. And he stayed up with me. He made sure I understood two things that evening. The first one is obvious. When assigned something, you do it and you do it on time.

But the second thing he explained to me was more subtle and way more powerful. He explained that I should start working on a project as soon as it was assigned. An hour or so would do fine, he told me. He told me to come back to the project every day for at least a little bit and make progress on it slowly over time. I asked him why that was better than cramming at the very end (as I was doing during the conversation).

He explained that once your brain starts working on a problem, it doesn't stop. If you get your mind wrapped around a problem with a fair bit of time left to solve it, the brain will solve the problem subconsciously over time and one day you'll sit down to do some more work on it and the answer will be right in front of you.

I've taken that approach with every big problem I've faced ever since. I used this technique to get through high school, college, and business school. I've used this technique to develop a career in investing and technology. I've even used this technique to deal with our own parenting challenges.

I'm a big fan of subconscious information processing. It is why I have my some of my best ideas in the shower in the morning. It is why I write every morning right after I get up. I believe that while I'm sleeping, my mind is churning through the things that I'm trying to figure out and often the answers are back (like a batch job) when I wake up.

Thanks dad for that tip. It's been a big part of my playbook ever since. Happy fathers day everyone.

Some iPad Help Please

I want to upgrade my original iPad's system software from 3.2 to 4.0. I've recently added some apps that don't run on 3.2.

The problem is I have no idea what mac laptop I used to setup that iPad. I think it may be gone to be honest. But the iPad wants me to connect it to the laptop that was used to set it up so it can do a software upgrade.

What is the best and fastest way to solve this problem? Should I do a factory reset on the iPad? If I do that will I lose all the apps I've got installed on the iPad? Is there another option?

I'm so confused why I need to connect an iPad to a laptop in the first place. Since that first setup, I've never connected the iPad to a laptop. I just download apps over the air and use them. Why can't an iPad do an over the air software upgrade like Android? Ugh.

Mark Suster Interviews The Gotham Gal

I talk a lot about the Gotham Gal on this blog but most members of this community haven't had the opportunity to see her in action. She spent last week in LA and dropped in on This Week In Venture Capital and had an hourlong chat with our friend Mark Suster. They covered a lot of ground, including sales as a key ingredient to entrepreneurship, women in tech, and what it was like to work with Jason Calacanis. It's long, just over an hour, and the audio isn't as loud as I'd like. But if you've got an hour to kill this weekend and are curious about my better half, its a good one.

Bloggers Block

After a great run the past month, I've hit a bit of an inspiration gulf. So I'd like you all to help me out of it. I'm soliciting blog post suggestions in the comments. I want everyone to go into the comments and vote up the best ones by liking them. Then I'll take the best five or ten and use them in the coming weeks.

Thanks.

Risk and Reward Are Not Obvious

I went to business school in the mid 80s. Investment banking was hot. The leveraged buyout craze was on. Junk bonds were hot. Everyone wanted to work on wall street.

I was obsessed with venture capital and had worked in a small venture firm the previous summer and had gotten an offer to work full time in venture capital for $60k per year with no bonus and no incentive comp. I also had gotten a job offer from an investment bank at $125k per year with a bonus opportunity of $250k.

Those investment banking job offers were all over the business school and almost everyone I knew took them. They all went on amazing summer vacations and showed up on wall street in September 1987. In October 1987 the stock market crashed and by December many of my classmates were out of work.

I took the VC job, made basically enough to live and work in NYC for ten years (subsidized by The Gotham Gal's income), but I did set myself up for Flatiron and then USV.

I told this story in a comment to my MBA Tuesdays post and figured it was worth posting as a full blog post. Risk is not obvious. And reward is not obvious. Don't do the obvious thing. Because I can assure you it rarely works out as planned.

The Treadpad

I got an iPad as a gift earlier this year. I use it in my home gym. Here's how it looks on my treadmill:

It was pretty simple to do this. I got some double sided velcro tape and put two strips on the treadmill:

And then I put two strips on the back of the iPad:

If you have more than one type of workout machine (ie treadmill and elliptical), you can move the iPad back and forth between both.

Some Thoughts On Aging

It's my 49th birthday today. I am taking the day off and spending it with my family at our house on the east end of long island.

For most of my adult life, my self image has been of the 20 year old me. The young smartass punk kid with a chip on his shoulder out to prove something to the world. That caused me some problems in my 20s and early 30s but worked out pretty well in the end.

That's all started to change in the past couple years. I've got a daughter in college and another planning to go next year. I'm starting to notice some gray hairs when the light hits my head a certain way. And I see a different person in the pictures others take of me. I see the wrinkles and the natural aging. And no Tereza I am not ever going to do the nip/tuck thing. That is most definitely not me.

My self image is changing and I'm starting to accept it. I'm getting older, more successful, and also a tad bit slower. I had to go back to yoga this year to deal with the aches and pains largely brought on by years of stress and bad posture. It has worked. I feel great. The Gotham Gal and I have learned to accept that our kids don't need us as much, that they want to make their own choices, and we have let them do that. Parenting is always the hardest thing to learn but teaches you the most.

Anyway, I am happy with the aging process. I like who I have become and who the people around me have become. My partner Brad told me that next year when I turn 50 I won't be able to pretend I am not middle age. Well I think I gave up pretending that in the past few years. I'm enjoying middle age and looking forward to what it brings.

The N+1 Theory

I lived with a guy named John Doyle in college. Like many people at MIT, John was brilliant. He instantly understood math and physics that sounded like foriegn languages to me. But he had his issues with drugs and alcohol that ultimately killed him before he reached 40. I'm saddended just thinking of John.

John had a theory he called 'the N+1 theory' and while he applied it destructively in his own life, I have often found great inspiration from it in mine.

The N+1 Theory states that there is always one more of anything.

Yesterday morning I was sitting at a cafe staring at my screen thinking 'what more can I write about on this MBA Monday theme?'. And then I thought about off balance sheet liabilities and I was off. N+1

I sometimes think that we've already seen every briiliant idea for a web service and then someone walks into my office and explains something fresh and new to me and I get that excited kid in a candy store look in my eye. N+1

I'll be in yoga class thinking that I can't possibly do another Vinyasa and then I do it perfectly. N+1

I have found that most of the time, there is always more where you think there is nothing left. You may have to look a little harder/deeper but it is there.

That does not mean that there is an infinite supply of everything. Math would say that when you extrapolate N+1 all the way out you get to infinity. But we are talking about life, not math, here.

I find the N+1 theory very inspiring. It is pure optimism sprinkled with tenacity and we need that in our work and our lives.