Sunday, October 29, 2006

Are early stage startups and normal lives incompatible?

I've been thinking about this the last few months. Much has been written about how todays startups are made up of a bunch of under 25 year old single guys living together in a house they rent to start an internet company.

Well, it's bascially true.

But there's another group that's also well suited for this lifestyle (and it's very much a lifestyle: it effects every part of what you do).

Who? Middle aged folks (between 40-60) who are either single/divorced or empty nesters. It’s not a large percentage of this group. But there’s a lot more potential startup guys in this group than you might think.

I'm in my 40's. I'm divorced. I'm in good health. I don't feel much different than I did when I was 25. I don't party like a 25 year old any more, but I have no problem staying up to 2am, working through weekends and doing whatever it takes. I also have no problem using my personal resources to make this fly, including my house as our office/development lab for the last year. Something tells me if I were married or had a live in girlfriend, that's not something that would have been possible (or, if it had, not gone on for anything close to a year).

In effect, I'm similar to those 25 year olds from a 'point in my life' perspective. I come and go as I please without checking with anyone. I get up when I wake up and go to bed when I'm tired (and the hours aren't even close to 'normal'). I have a social life, but nothing like what a 'normal' single guy in his 40's has. I'm seeing a women, but she'd be the first to tell you it's not a 'normal' relationship (we're lucky if we get one night a week to do anything). It's very much like when I was a 25 year old guy on my own. Only, now I'm a 40 something guy on my own.

The only real differences are financial (I'm at a place most 25 years aren't) and life experience, but that works to our advantage. Having the resources of a house to work from, effectively turned into a sort of residential office building (ahh.. back to that ‘frat house startup thing), not worrying about income for long periods of time and financing the costs of getting everything off the ground and running for a year or so is a real advantage in a startup. Also, having a broad set of experience helps to avoid at least some of the pitfalls, and brings some degree of adult supervision to the party. Some of my folks call me dad though, which both pisses me off and makes me smile.

The reality with a startup is the work comes first. The big difference for me between this and most 40 something's doing a 'day job' is it's also my play. Given a choice in what I'd do in my 'off time'.. well, this is it. So the two (personal and professional lives) merge and become one.

Many would say this is bad, unbalanced, a precursor to burning out. I disagree. Do I want it to always be like this? Well, maybe I'm just not cut from the same cloth as most, but yea, I do. Right now, assuming we succeed with ClickCaster and it goes to it's logical end (being acquired or going public), I would, absolutely, do it again (and again). This must be what they mean when they say 'he's got the bug'. It really does get in your blood.

And to all my 40 something friends who are married with kids still at home with day jobs, car payments and mortgages: you CAN do it, but it's more than a stretch, it's a commitment every bit as big as getting married or having kids. More so in some ways. It's a way of life, and it takes massive amounts of your time and, more importantly, your attention, than you ever dreamed going in.

My guess is only a small percentage of marriages can survive it (and yes, some can). I know though I would not be doing this if I were married. I would not have turned down that mid six figure executive job at the fortune 50 company with my (now ex) wife looking over my shoulder. The privilege of creating something from nothing but your mind, and turning it into something real, useful and valuable in the world doesn’t carry the same weight as the big title and paycheck for many spouses. Nor does the possibility of crashing and burning with zilch to show for it in a couple of years give your significant other a warm fuzzy feeling.

The one's the do make it work, at least that I've seen, have both spouses involved in the business. That, or they have a full and engaging professional life of their own keeping them occupied when you’re working a 16 hour day.

At that point, you have to ask: why are we doing this again? I’ll bet you a day of Iraq war expenses your spouse will.

And kids? Well, that's a tough one. You're going to miss a lot of their lives. Period. You can tell yourself no, I'll make that work, I'll find the time to get to Heather's play or Bobby's soccer game, but more often than not, you won't. The servers will go down. A key customer will show up at the airport 'on a stopover' and want to meet. Something pressing only you can handle will pop up and you’ll have to handle it and miss that play. It WILL happen.

I know this is going to piss off some people. And it's likely to be skewered by some of my own family and friends as well as many who think it can be done (and are trying to do it). But, I've been there (Married, with a kid) and there's simply no way I, personally, could have done a real startup with all the overhead (yea, I know... it sounds cold, but it's accurate) of a marriage, a family and all that requires in the equation.

Much of what I write about here are the experiences of being a first time CEO and startup guy 'later in life', and this is very much part of it. Most people my age (married and divorced) take the easy route of staying in their good paying jobs, doing something they don't particularly like for a company they don't particularly believe in. It really is easier, more comfortable and a lot less scary than starting a company from scratch.

For me, though, it feels a little like being chained up. Really nice pretty shiny velvet lined chains, but chains nonetheless.

Doing a from scratch technology startup isn't for everyone. I'd say, maybe, 5% of the population can do it; and only a small percentage of that group can actually be successful at it. Society makes it hard for us to break the social contract of getting a good job, finding a mate, having kids and retiring to our 'hobbies'. And for that 95% of the population, it’s a good life. My dad is one of those guys. He’s had a good full life. He’s happily retired from a lifetime job at IBM. He doesn’t fully understand what I’m doing, but he tells me he’s amazed and proud of me for doing it. I’m pretty sure he even means it.

Someone has to start things. Someone, somewhere, sat in a garage or basement or an employers office and thought up IBM, HP, Ford, Apple, CitiBank and all the other big companies millions of us work for today.

We've got to have it, and that small percentage of under 25 year olds who don’t know better and (mostly single, divorced or empty nester) middle aged guys who do know better but have the balls to do it anyway are what it takes to make it happen.


Don Shade said...

Well put Scott. I'm lucky to be married to a gal who comes from a long line of entrepreneurs--on both paternal and maternal sides--who made and lost fortunes. And I have found work in the domain of my hobby. Choice of spouse and work continue to be the most important in my book. At 46, I have images of Shawn Fanning sitting on his couch with laptop and Red Bull hacking out Napster. It's impossible for me to work at home and there's not enough Red Bull to provide me the energy of a 19 yr old. So I spend a lot of time in coffee shops.

Anonymous said...

Great post Scott, and almost dead on fm my past experience and days long past ;-) However, I now have 4 close friends and myself, all of us 40-something, all of us married, and all of us at various stages of our respective start-ups. Having said that, yes, there are some things you miss w/your family, but because we're older, we also know how not to let some parts of the business comandeer our lives, and how to make time for other things available. Not every thing is a firestorm as it once seemed. It becomes more about working smart, not just working all the time.

Start-ups are definitely not for everybody, and every one of these 40-something entrepreneurs has been one before, so they're not newbies at this. Perhaps that also explains how they have learned to balance the effort knowing that there are times when important tasks have to take precedence over family and vice versa. Another common element of all of these entrepreneurs is that their wives knew what they were getting into. Some have been w/them through more than one start-up (w/o necessarily being involved in the biz), others have been around entrepreneurs and knew that this was the type of personality they were attracted to.

I would agree on this point, it's easier to do a start-up at any age when you don't have encumbrances to distract you, but it's not a pre-requisite for start-up success :)

Anonymous said...

This is great! I almost did a re-think after I went to a couple of networking events for web start ups in the Bay Area and I would not have been surprised if they had called me "pops." Like you said there is no reasons why one cannot do a start up at any age othr than ones you nicely captured. However I found that the older I got the smarter I got based on the experience I have gained in the business world. While I may be taking the same amount of risks and also making judgements based on little information, I would also be smart about getting out of potential dry holes and trying new strategies. Thanks for your post, it gives me heart.

meiwah said...

Great write up! As an entreprenuer at age 40 I found your article inspirational. I took the plunge and went out on my own 2 years ago and I can't imagine going back to working for someone else. I've got 2 more ideas so one can say I've got the bug. I also find dating with my crazy schedule a challenge at times then again it makes for a good filter to weed out the guys who can handle it. All in all I love my life and wouldn't trade it for the world.

Roman Rytov said...

What you're basically saying is your time should belong to you or to your idea and your age doesn't matter. As soon as you're single the odds you can devote a big portion of your time to the idea are greater than if you have family burden. Other than that there is no much difference between 25 and 40.
I'm at my 34 and with 3 kids, my wife, and a dog probably in the minority of family-equipped folks that are still possess lots of time when it comes to the business. My wife grumbles at me when I escape house for a couple of hours of long runs but if business/studying takes extra of the family time it finds more acceptance and understanding (still they hate it but accept and understand).

I'm sure there are many successful businesses (and it's not necessarily less time consuming than startups) where families support the entrepreneurs although you have to sacrifice something. No doubt. When you're single you have much less to lose:-)

Chris said...


A very thoughtful post. This is an issue I face myself, as a 32-year-old with a 4-year-old and a 2-year-old. For the time being, I've been working at rather than founding early-stage startups.

Your post was inspiring--when my kids are teens, I'll still only be 42--plenty young enough to start several more companies!

Scott Converse said...

Great comments by all! I especially like Rick Klaus's response on his blog ( and how the feedburner guys, all in their 30's, all married with kids and all riding the incredible success feedburner's experiencing AND having balanced (at least reasonably so) lives.

As I said, it can be done (but it ain't easy), and to those of you out there able to make it work, I congratulate you. What I'd love to see are some posts on how you actually pull it off. We could all learn from those of you really doing it day in and day out!

An excellent read from an ex-evangelical.

  As you know, I once was an evangelical megachurch pastor and my pastoral career stretched over many years. Eventually, I could no longer t...