A wife, a baby, a mortgage, and a startup.

I spend a lot of time out and about at startup events here in Boston/Cambridge.  The scene has really been picking up steam lately, to the point where there are at least two or three really great meetups per week.  Being a pretty outgoing guy, I do a lot of networking and answer a lot of questions about our company, mentors / advisors, TechStars and the like.  But this post isn’t about any of them, it’s about my family.  Or more specifically, the question I get asked more than just about about any other – how do you have a startup *and* a family?

Rule zero – Pick an amazing wife / husband

Seriously, the only way to do this is to have someone who will really step up and do way more than 50% of the family work.  Someone who understands that this is what you need, that you have the startup defect(1).   Not everyone can handle the serious ups and downs of being married to a “you”.  The term “startup widow” isn’t a joke.  Respect that.  Seriously.  If after laying out the deal (leaving a well paying job, living on savings, working way to much), your spouse isn’t into this, stick with your job until you can de-risk it for him/her more.  And understand that they may never be into this life.  That’s ok.  It’s certainly not for everyone.   If that’s the case, maybe you can join a funded startup and still keep your startup defect happy.

Rule one – Learn to juggle

I’m not kidding.  Really, do it now.  Why?  Cause you’ll quickly see that juggling isn’t about having everything precariously up in the air.  Juggling is about control.  It’s about keeping as many things under control as possible and realizing that you’re constantly going to be losing control of something (a bit), but that’s ok when you’re gaining control of something else and have full control (ie: it’s in your hand) of the last ball.  For me there’s my company, TempMine, my wife, and my son.   I will never be able to do everything I wish I could for everyone.  It’s ok to let your startup fly a bit, so you can keep your wife happy (and sane) and your son remembering what you look like.  Just keep the flight of the company in mind and realize that you have to toss something else before the company lands.

Rule two – Keep everyone in the loop

If I have something family that has to happen, I let my team know.  If I have something startup that has to happen, I let my family know.  Sure, there will always be surprises, but work really hard to make them the exception, not the rule.

Rule three – Over deliver

Your schedule is just plain insane when running a startup, but you make sure you over deliver often.  If this means cranking late in to the night to get something done for your team, do it.  If it means blowing out of work early so you are home for bath-time on a day when you normally wouldn’t, do it.  Realize that your role is hard on everyone, but they’ll forgive you for a lot of the not being around if you over deliver when they least expect it.  This stuff also goes a long way towards keeping you sane.

Rule four – Weekly something

Every Saturday we have a family breakfast.  It’s usually a little  more elaborate then a regular breakfast.   We sit at the table (something we don’t do together often enough) and eat and laugh and just enjoy each other.  I make it.  I clean up after it.  It’s one of my favorite times of the week.  I don’t think it matters what you do, but pick something and do it with everyone.  I wish we could eat together every night, but for now, Saturday breakfast will do.

Hash browns, scrambled eggs, and sausages? Oh yeah!

So, what works for you?    Leave a comment!

1. What’s the “startup defect”?  Well, it’s that thing that makes you *have* to do this.   Starting a company that has a little chance of success and a major chance of eating up your savings and retirement is a *not* the smart thing to do – even when you’re smart person (and I hope you are, because I hear it really helps to be smart when running a startup …)

family, starting the startup

It was about this time last year that I started to think in earnest about TechStars.  I had the original (612 iterations and now one pivot old) idea for TempMine and thought that maybe that nice, stable job I had wasn’t really what I wanted.  So I started digging into TechStars.  I followed everyone TechStars related on Twitter (heck, I *joined* Twitter as a research tool for my application).  I listened to interviews with David Cohen and Brad Feld.  I read blog posts.  Oh my, did I read blog posts!  I devoured all I could find that had anything to do with TechStars.

Through all of that content, there was one recurring theme that rose above all others – “mentorship-driven.”  Everywhere I turned, when I saw TechStars, those two words were not far behind.  And you know what?  They are why I applied to TechStars.  It wasn’t the seed funding (though that did help nudge my wife to agree to the insane idea of my leaving a perfectly good job).  It wasn’t the fact that such a high percentage of past companies had raised seed rounds and gone on to create very cool companies – and sometimes sell them!  It was the people who helped the teams.  It was their bios.  It was what they had done.

You see, it’s not even the intros to these folks (but trust me, those are crazy valuable on their own – especially here in chilly Boston).  It’s also not really the sessions that they give (though there are a ton of those and they are freakin’ amazing, you’ll be shocked afterward at how much you didn’t know).  It’s their availability.   When you meet these mentors, you’ve already crested a threshold that many, many others haven’t.  Where many of these folks are also investors, they are constantly pitched, yet when you’re a TechStar, they are voluntarily lowering their guard for the most basic of reasons – they want to help you.  They all had help along the way.   They know the value of being helped.   They know that we, as a startup community – whether we’re in Boston, Boulder, Seattle, Valley or wherever, will all do better when the more experienced help the less experienced.

So look at those lists of mentors (Boulder, Boston, and now Seattle).  Look at what those men and woman have done.  Look at what they do now.  Are you seeing the value I saw before applying?  Here’s the best part.  As much as I thought I got “the TechStars way”, this mentorship-driven thing, and I did, conceptually -  I was off by an order of magnitude.  It’s way, way better.

The mentors have been there (where you want to go) and done that (what you want to do).  Your mentors will ask you smarter and far tougher questions about your plan, your assumptions, your direction than anyone else.   They will challenge you and sometimes tear your idea apart.  Don’t worry, that’s a good thing.  Better they do it during TechStars, than the market afterwards.

The mentors know everyone.  They knew people who you never knew even existed.  They bypass gatekeepers, email filters, and all the other stuff that was designed keep you out.  They will make intros to folks who just don’t have time to talk to startups, but for your mentor, for you, will.

The mentors care.  They carve out real time, often a crazy amount of real time, in their schedule to help you and your little startup.   It’s amazing how much you can get done in a 30 minute meeting, with an insanely sharp, outrageously experienced { VC | serial entrepreneur | angel | lawyer … } who’s there to ask questions, to push you, to help.

This is starting to sound like an infomercial “but wait, there’s more!”

There is more and if you don’t screw it up, there’s a lot more.  Here’s the real special sauce that I don’t see mentioned enough (so I might get in trouble for letting this slip – oops).  TechStars is not a 3 month program.  Sure, the main program lasts for three months, but being a TechStar does not end with the last pitch on investor day, or when you move out of the penthouse, bunker, or where ever they shack you all up in Seattle.   Your relationships with your mentors don’t end.  Your access to great help, to people who are invested in you (personally as well as in some cases, financially), does not end.  If you do it right, you’ll exit your three months in TechStars with friends who just happen to have IPO’d a company or two, angel invest, and know pretty much everyone – and man, those are great friends to have.

If you’re working on a great startup, something that keeps you up at night and gets you out of bed in the morning, something you’re excited about and you realize the value of great mentors – apply to TechStars.  But hurry up – applications for this Spring’s Boston session close on the January 11th.

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