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

New jobs for both of us.

Tom — Tue, 25 Oct 2011 14:38:43 +0000

Yesterday was my first day at HubSpot. It was my first “first day” at a job in a very long time. There wasn’t really a first at my last company, play140. We just got started. There was no culture, no “way things are done”, nothing was set in stone. That’s one of the coolest parts of startups, you get to do it all. It’s exciting. You can try to do everything right that everyone you’ve worked with or for before has done wrong. And you’ll probably fail. But that’s a part of the adventure.

HubSpot is still called a startup by some, but in reality, I don’t think it is any more. This is a *big* company. They have an unbelievable sales team who sell what is built here for real money every day to people who want to buy it. They have set “way things are done” for just about everything. They’ve been around for five years. There are nearly 300 people here. It’s kinda crazy. Maybe I need to change the title of this blog …

While yesterday was my first day here, it was also my wife’s first day as a full-time Mom with our 3.5 year old, Thomas, and our 12 day old, Miles. So while I was here trying to get up to speed on years of history, projects, work, style and about 30 new names to remember, she was at home entertaining our two monkeys. I’m not sure who’s day was more exciting or exhausting. She did let me actually get my shoes off before handing over Miles though. So it couldn’t have been that bad.

All your life are belong to us

Tom — Fri, 14 May 2010 11:22:26 +0000

102 weeks ago, I spent way too much time assembling a list of the folks we wanted share our “hey, our inside baby just became an outside baby” email. This was not a fun process, but we did it anyway and I’m happy we did. I also blogged the entire hospital -> labor -> birth from the tiny, craptastic “keyboard” of our long since gone, original iPhone. In short, I worked to get the message, a message I was very, very excited about, out.

Today, not even two years later, things are different. With my role at my new startup (+ dad of the aforementioned 2 year old, and husband of a super patient wife), I just don’t have much time to fart around online. While the world has transition on to Facebook, I’ve slowly transitioned off. This hasn’t been a big decision – no, I’m not taking a stand against the Rube Goldberg machine that is Facebook’s Privacy Settings. Rather, it’s been a consistent string of small decisions – decisions not to open the app on my phone or site in my browser. Decisions to not consume the little blips of my friends and family’s lives.

Missing out

You see, I have a serious issue with status updates. I must consume them all. This was easy when FB was small and I could count my “friends” on a couple of hands and feet, but now, even with very managed growth of my friends list and an iron “Ignore” finger for new requests, I just can’t keep up. Since I can’t handle just a snack of my friends’ lives, for the fear that I’ll miss out on something, I’ve stepped away almost entirely.

In doing so I’ve missed two births and a tenure award/promotion. Three life changing events that used to merit phone calls and emails blasts are now owned by Facebook. When I found out the other day that friends of ours had their first child five days earlier I was floored. Floored that I didn’t know, that I hadn’t somehow heard. I *never* miss an email (note: this is not a guarantee that I actually reply, just that I never miss even one). I was told “it was on Facebook”. The same thing happened last week when my brother-in-law was awarded tenure and a promotion. I missed it. It was on Facebook only. Sure, eventually I got a call with the info, but I’d missed it when it was news.

This seriously bums me out. Not that I didn’t see these when they happened, or that I wasn’t personally notified, but that these really amazing, important, life-changing events have been dumbed down to a Facebook status update. That the care that goes into an actual email, a call, a blog post, is gone. Now that everyone is on Facebook, you can just carpet-bomb your life’s best moments into the stream that will get lost below the fold before you know it, and way before I know it.

Five rules for startup + family happiness

Tom — Sat, 30 Jan 2010 17:58:54 +0000

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 …)