VC Lifestyle Myths (in Retrospect)

December 23, 2006December 23, 2006 / Adam Nash

A great post this week from Susan Wu at Charles River Ventures on the myths surrounding the legendary lifestyle of Silicon Valley venture capitalists:

Susan Wu: VC Lifestyle Myths

I was reading along, waiting for something to resonate, when I saw this screenshot:

Ah yes, it is all coming back to me now. The VC Lifestyle.

Now, let me be upfront about something here. I love venture capital. Honestly, I do. The idea of job where you are striving to know as much as possible about technology, people, strategy, and building businesses is definitely in my sweet spot. Not only that, but I continue to be amazed at the almost accidental set of circumstances that gave birth to the modern venture capital industry in Silicon Valley, and the amazing value that has been generated because of it.

All of that being said, the reality is that the VC lifestyle is not as glamourous as you might think, and definitely has elements to be desired. Susan captures a few key elements that definitely resonated with my memories of being an Associate at a large, early-stage venture fund:

Tyranny of Outlook. Meetings, meetings, and more meetings. Easily 6-8 a day, mostly pitch meetings with entrepreneurs & executive teams. The day is blocked off weeks in advance, and as a result, you are constantly moving things around as things come up, meetings go over, and you are trying to meet with just one more person.
Miles wide, but inches deep. It’s hard to imagine being lonely when you are meeting literally 20 new people everyday, and your rolodex grows to the thousands. But a vast majority of your contacts are people you meet once. Many others you might talk to once or twice a year. Even fellow venture capitalists and entrepreneurs that you are close too might touch base on a weekly basis. The reality is that the only people you truly see every day are those in your office, and our office was small. At it’s largest, we had two partners, an associate (me), an analyst, two executive assistants, and a receptionist. That’s not a lot of people.
Coopetition. Without getting into the nuanced politics of venture capital, it can be draining at times. As a young person in the industry, you are at once trying to build a reputation for yourself and carve out a niche, but at the same time you need the support and assistance of others around you. In the long term, you are judged on your own success, but in the short term, you are judged on your support of the senior partner(s) you are working with.

When I think about my life at eBay, it’s amazing at how much my experience in venture capital has helped me.

First of all, my Outlook calendar still looks like that. 🙂 Maybe that has more to do with growth, drive & Silicon Valley than venture capital itself.

Second, I truly love the number of people I get to work with at eBay. Love it. Not only have I met literally thousands of great people at eBay & PayPal over the past four years, but there are hundreds of people that I now know fairly well. Leading large project initiatives and new businesses at a larger company may be more constrained in some ways than leading a startup, but the counter-balance is the number of people you get to know and work with.

Third, my orientation towards senior executives has shifted. Before venture capital, there was some degree of awe that I felt around CEOs & executives of large technology companies. While I still respect their achievements, I found that venture capital gave me more grounding around the fact that these are, in fact, just people. At eBay, this has allowed me to be more comfortable, in general, around meetings with our senior staff. I still see to this day so many bright people, with excellent ideas, get tripped up the moment they have to succinctly and convincingly present an opportunity to a senior executive.

I’m quite happy with my move back to an operational role in 2003, and I’m extremely happy with the opportunities I’ve been given to help design, launch, and build brand new sites & businesses at eBay.

But some day I’ll likely go back to venture capital. Maybe. Right time, right place, right people. But not yet.

(BTW, If you aren’t reading Susan Wu’s blog, it’s worth bookmarking. I have a special place in my heart for any venture capitalist who actually play World of Warcraft, and can actually comment intelligently on technical issues.)

Blogs I Read: Ben Stein

November 13, 2006November 13, 2006 / Adam Nash / 2 Comments

I really love to read Ben Stein. His first burst of fame, as you may know, came from being the teacher in Ferris Bueller’s Day Off back in the 1980s. More recently, he hosted a game show for a while (Win Ben Stein’s Money), and he writes regularly for the New York Times on Sunday.

What people may not realize from his typical movie and TV stunts is that Ben Stein is really intelligent. Not just in a book smart kind of way, but in a profoundly intellectual way. As an actor, writer, economist and lawyer, he seems to have internalized not just the facts and theories of several different fields, but also how they fit together. I find his writing style compellingly simple, and yet rich and articulate.

More recently, Ben has become more proactive with writing articles to help guide people with their own financial lives. Here is an article he wrote in 2005 on saving for retirement:

The Early Bird Gets the Next Egg

An example passage, which I think demonstrates both his easy way with numbers and his compelling presentation of basic financial facts:

If you start at 25 with six months’ salary saved, you need only save 3 percent of your total, pre-tax salary per year to get the nest egg you need (roughly 15 times earnings at retirement) by age 65. But if you start at age 45, you need to save 18 percent of your salary (again, assuming you start out with six months’ of salary saved). If you start at age 50, you need to save 28 percent of your salary. And if you start at age 55, you need to save nearly 50 percent of your gross salary to get where you need to be.

In other words, if you start with a sensible plan at a young age, you can get to your savings goal without breaking a sweat. If you wait until you are middle aged, it takes some serious doing. If you wait until you are a silver fox, you’re required to do some heavy lifting indeed. If you assume the stock market has passed its glory days, you need to save even more.

I’ve found two great resources now for Ben Stein fans:

He has a website. It’s worth bookmarking.
He has an RSS feed. It’s worth subscribing to.

I’m going to be writing a follow up post on one of my favorite pieces by Ben Stein, clipped from the New York Times last year. I’m having trouble finding an online copy, so I may have to type up the whole thing. In the meantime, check out his RSS feed. It’s so exciting to me to find out that some of my favorite columnists and authors have their own feeds – it’s something I just wasn’t finding somehow before I started blogging myself.

Blogs I Read: Mac Mojo (The Microsoft Office for Mac Team Blog)

November 4, 2006 / Adam Nash

This is a relatively new one for me, but I find the posts pretty interesting from time to time.

This is the team blog from the group responsible for Microsoft Office for the Mac. Most people don’t realize this, but Microsoft Office actually originated on the Mac, and despite all the conspiracy theories, the business continues to be a fairly large one for Microsoft.

For example, check out this post from yesterday about the size of the Microsoft Office for Mac codebase. It shocked the hell out of me:

It’s all in the numbers…

30 million lines of code. For a suite of applications. Unbelievable.

For those of you non-technical folks out there, this is a really big number. I remember when it was revealed that Windows XP was approximately 40 million lines of code, and Sun had a field day pointing out that Solaris was only 7 million at the time.

In software, bigger is rarely better from a complexity or reliability standpoint. This blog post explains some of the very human reasons why.

I personally have always believed that a complete rewrite is likely necessary from time to time with software applications, usually every 3rd to 4th major version or so. The problem is, the economics so rarely support re-writing a codebase. The time you spend rebuilding what already works could be spent on building new features, or fixing old ones.

In a small way, this legacy cost is what helps fuel the ongoing development of new applications, new companies, and new businesses. It is always easy for the new entrant to “rebuild” what already exists. This doesn’t make up for the incredible market advantage that the large players have, but it’s an interesting cost advantage that you don’t normally see in most industries.

Anyway, check it out. Since I am a longtime Office for Mac user, I like seeing ongoing communication from their team to the community.

Blogs I Read: Jason Steinhorn, The Steinhorn Stare

August 31, 2006 / Adam Nash

One of the most fun blogs that I read is one that belongs to my friend and colleague, Jason Steinhorn. It’s called, “The Steinhorn Stare”, I’m assuming after his now infamous poker face, captured on television as part of the World Series of Poker.

Here is a great example of why I love reading Jason’s blog:

2006 Legends of Poker

Now, I will be the first to admit, I am clearly a voyeur of the recent poker boom that has hit Las Vegas, the internet, and about half of the engineers and techies I know. I really appreciate the way that Jason’s posts capture the subtlety and complexity of the game. Poker is a fascinating blend of psychology and math, with a distinct advantage to those who know how to manipulate the perception of their play vs. just knowing the odds.

As a result, Poker lands squarely into my “sweet spot” of fascination – an arena where the ultimately rationale (statistics) intersects with the ultimately irrational (human emotion & perception).

So while I may never be a great poker player, I like living vicariously through Jason and other friends who participate in these events with $10K buy-ins, and who actually win.

True story: Last year, Jason & I were both managers in the same division of eBay Product Management. At our regular Monday managers’ meeting, Jason was nowhere to be found. He was still in Vegas, having won 2nd in the World Series of Poker, and close to a quarter of a million dollars.

That news would be cool enough, but what I liked is that Jason had faxed in the winning check – like a “doctor’s note” to be excused from class that day.

This is Jason’s last week at eBay, and he’ll be sorely missed. But he’s off to a new adventure at another cool company, and I feel extremely fortunate to have been able to learn from him these past two years.

Now, if he would just post more regularly to his blog…

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