dadworking

Reflecting on priorities of family & work

The Tale of the 40 Year Old (Wannabe) Entrepreneur

PrototypeSketch_R2gWhether you agree with it or not, a specific archetype exists of the startup entrepreneur – young, hungry (often literally), and single-minded. Nothing is more important to this person than launching a successful business. Working nights, weekends, and holidays and subsisting on energy drinks with the occasional nap, this person is driven to be first to market with the most innovative new product or service. Equipped with business savvy and engineering chops,, the startup entrepreneur is constantly challenged by others –  those who are already six months ahead, and those who are hot on their heels with another product that looks eerily similar to theirs.

I, on the other hand, am a 40 year-old, happily married, father of two who falls asleep by 10 (to be fair, I am up well before 6), enjoys dinner with his family, and spends weekends coaching soccer and exploring the Bay Area or watching football. I value the fact that my wife works part-time at a job that she doesn’t particularly enjoy so that we can have a little bit of extra money and she can do what she does best – be a mom to our twins. We put money away in college savings accounts, a 401(k), and support the nonprofits we believe in. All in all – a pretty great life.

Over the course of the past 6 months I have been running a startup company largely as a hobby. It started with a win at a Startup Weekend event this past Spring, followed soon after by an incubation over the summer of a prototype within the nonprofit I run. Currently, there is interest from funders, customers, and partners. So now what do I do? Without thought, the archetypal entrepreneur drops everything he/she is doing, seizes the momentum, and goes to market before anyone steals the idea.

Without thought. That’s just it: I have to think,and my thinking is based on a single question:

What happens if I quit my job to launch this startup?

My wife goes on the job hunt to find a higher paying, full time job with benefits. We stop contributing to our future savings, mortgaging everything we have. We put our kids into the after-school program at school until 6PM every night. Before my wife or I get home, we pick up something for dinner and then shovel it down while we ask perfunctory questions of our kids about how school was. While she puts the kids to bed, I jump on my laptop. She tries to engage me in conversation while I furiously email our technical team about the latest bugs and newest features we need. She kisses me good night and goes to bed. I stay on the couch to work and manage about 3 hours of sleep.

My kids wake up, but I don’t know it – because I’m already out the door, boarding a plane to sign up new customers in another state. Before I go home, I have a layover and parlay that into a meeting with a potential funder.  I land around 10PM, drive home, and it’s the weekend. But I have to work. You get the idea. I have no delusions that building a successful startup takes anything less than what I’ve just described. There is a potential pay-off, of course, so let’s play out the best-case scenario for the business.

I decide to go all in and it’s wildly successful. Fast-forwarding three years, we’re acquired by a much larger company.  I work tirelessly within that larger company until I am allowed to exit two years later. I am financially set for life. Or – worst case scenario. All of that happens, but the stock in the larger company I now hold becomes worthless and I am back to square one. Or – most likely scenario. We raise a couple of rounds of funding but after several years, don’t get over the hump to mass adoption or profitability so we shut down.

No matter what, my kids are now 3 years older, and I missed it all. It’s hard for them to understand where I was all of those years. And as I project forward, it’s hard for me to understand as well. So it is with forethought and not hindsight that I made a decision not to pursue the startup. At the end of the day, there are many more things more important to me than launching a successful company.

Launching a startup is about sacrifices. I know this all too well, as before I had kids, I was a social entrepreneur. I started and ran a charter high school in South Los Angeles for 5 years. I had to hustle for customers (students and parents), raise money to supplement the paltry sum we would get from the state, hire and manage a team of 30+ teachers and support staff, adhere to a stringent set of requirements from the state and the local district, and on and on and on. I know 7 days/80-90 hours a week and it’s not what I want to do again. In fact, everything in life is about sacrifices and the one thing I am not willing to sacrifice is being there to watch my kids grow up.

But who knows  – maybe 10 years from now when my kids are in college…

Note to readers: I wrote this 3 years ago and didn’t have a place to publish it until now. It’s interesting to reflect now and know I made the right decision for me and my family. Special thank you to Mandela (check out her blog on the challenges of entrepreneurship) for the inspiration to dig it out and for editing my ramble.

6 comments on “The Tale of the 40 Year Old (Wannabe) Entrepreneur

  1. Nicole
    August 8, 2015

    As a almost 40something, entrepreneur, mother of 1 amazing 2 year old, I must chime in and say it’s not all or nothing. In the last 2 years I moved, opened a school (and am opening another one this coming year), my son is healthy, heading to preschool this year and I’m happily married. No I’m not running co-op parent Ed classes, cooking five course meals or teaching my kid calculus BUT I’m completely fulfilled and a better mom, wife, boss and friend because of it. San Diego has more great schools because of my work and there is one more voice in Ed reform. You chose some other great ways to be an entrepreneur and support entrepreneurs. I would argue you also found a way to have it all. (Although I wish I had My Sci High for my schools). There is something to be said about doing this work later in our life. Maybe it just makes us work smarter and know we don’t have to do it alone and let’s us save the superheroe cape for night story time with the kids.

    Like

    • DadWorking
      August 8, 2015

      First of all – you’ve accomplished way too much to not be 40 yet. Unfair. Anyway – I love the context you contributed as it tells an alternate story. I hope it didn’t come across as impossible; it was more to highlight the choices I made and why. Keep doing what you’re doing and hope to visit your new school soon!!

      Like

  2. Nicole
    August 8, 2015

    As an almost 40something entrepreneur and a mother of 1 amazing 2 year old, I must chime in and say it’s not all or nothing. In the last 2 years I moved, opened a school (and am opening another one this coming year), my son is healthy, heading to preschool this fall and I’m happily married. No I’m not running mommy and me co-op classes, cooking five course meals or teaching my kid calculus BUT I’m completely fulfilled and a better mom, wife, boss and friend because of it. San Diego has more great schools because of my work and there is one more voice in Ed reform. You chose some other great ways to be an entrepreneur and support entrepreneurs. I would argue you also found a way to have it all. (Although I wish I had My Sci High for my schools). There is something to be said about doing this work later in our lives. Maybe it just makes us work smarter, understand we don’t have to do it alone, and let’s us save the superheroe cape for night story time with the kids.

    Like

  3. Pingback: The Tale of the 40 Year Old (Wannabe) Entrepreneur - The Startup Couch

  4. Andrew
    February 13, 2016

    I”m a 59+ Wantreprenuer who started and ran 4 startups b4 40. I gave up 20 years to be with my kids. Now as the last one is about to enter college, the entrepreneur is about to bust out! Keep your dream… It’s never over!

    Like

    • DadWorking
      February 13, 2016

      Thanks for sharing, Amdrew. I’m still channeling my inner entrepreneur but in different ways. I’m sure when my kids hit college – the gloves are off.

      Like

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s

Information

This entry was posted on August 8, 2015 by in Parenting and tagged , , , , , , .
%d bloggers like this: