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

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.

Tom family, real job

Setting up email is pretty much one of the first outward facing things that a startup does.  You need to own your company identity, and folks need to associate you, your product, your everything, with that identity.  This often happens first via email.

So let’s say your name is Bob Fundergrass, you’re a founder, and your startup’s domain is toejamsoup.com.  If I can’t email you at bob@toejamsoup.com, you’re an idiot and you are doing it wrong.  I don’t care if you really use bfundergrass@toejamsoup.com, or some other variation, but your first name, what people actually call you, better work.  If it doesn’t, you’re an idiot.

Please don’t make this mistake.  You’re a founder, claim that first name and own it.  Sure, maybe down the road you’ll have 30,000 employees and need a really stodgy, strict format, but right now, you need to make it as easy as possible for everyone and anyone to email you.  Your first name @ your domain is the easiest way to do this.

You have enough things stacked against you already, please don’t add bounced or black-holed emails to the list.

PS: An easy way to do this if you use Google Docs is to set up a Group and name it and set the Group email address as your “easy” address.  Then just set your main account as the owner and select “Also allow anyone on the Internet to post messages.”  Bingo.  You’ll capture those emails and be able to reply from your preferred address.

Tom being the boss, starting the startup

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.

Tom family birth announcement, facebook

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 …)

Tom 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.

Tom Uncategorized

I’ve heard these stories of startup founders where great stuff just happens to them. They’re telling a friend about their latest idea and are overheard by some angel who immediately writes them a check or they create some neat tool in their spare time, while holding down a real job, and then become superstars earning millions and flying around the world to speak to their screaming throngs, or they create some neat little tool in a weekend and end up selling it a month later for $10 million.

All crap, seriously. I don’t believe any of it. Sure, there might be some fantasized retelling of a startup that starts with these lines, but there not reality. Maybe I don’t believe them because they haven’t happened to me. Maybe I’m just a doubting Thomas after all.

Last spring when we applied to TechStars with the original, now long-dead idea for TempMine, we were very excited to make it through the first cut from a  500 or so companies down to fifty.  But making the first cut wasn’t the goal and we weren’t in yet.  We still had to beat out 40 other teams to get a slot.

I then saw a tweet that Shawn Broderick, the Director of the soon to be first Boston class of TechStars was going to be at Andala Cafe for OpenCoffee the following week.   Did I wait around for someone to overhear me talking about TempMine?  Did I sit in my house and code, code, code hoping to get noticed?  Did anyone buy TempMine for $10M?  No, no, and sadly, no.  I got off my butt, skipped a few hours of work, and got in Shawn’s face.

Applications for TechStars Boston 2010 are now open and getting into TechStars is hard.  The odds are quite literally stacked against you.  Tilt them a bit, go meet Shawn.  Go meet some of the TechStars alums who are going to be there too.  Go find out why I jumped at the chance to leave a great job and chase my dream.

Come learn more about TechStars as Shawn hosts an Info Session at 10:30a on Wednesday, Dec 2nd at Andala.

Screw serendipity – make it happen.

Tom starting the startup, TechStars

When I started this blog it was with the intention of saving some of the great summer experiences for myself and sharing them with my friends / family who weren’t seeing a lot of me.  But then, every time I tried to write something, I couldn’t divorce it from the fact that the reason I was among the missing was that our company, TempMine, had been accepted to the inaugural class of TechStars Boston.

We’d decided that it was best that we keep mum as the word about our TechStars  participation because you only really get one chance to make that first impression.  And frankly, for most of the summer, our product and business model were in such states of flux, we didn’t even know what sort of an impression we wanted to make anyway.

So I started posts, and then left them, to wither on the vine – something that is very easy to do as you have so many other things going on whether it be big sessions with mentors, one-on-one’s with mentors, pitch sessions, weekly updates with Shawn (Broderick, the Director of TS Boston), meetings with potential customers and users, or just plain building something.

When in TechStars you have no time. Everyday is jammed. Crazy jammed full of things that you just can’t miss. Meetings that are far to valuable to skip. So taking time to blog, just didn’t happen, especially when I felt like everything I wanted to say wouldn’t have made much sense without the word “TechStars”.

But now, we’re graduates of the program. We’re TechStars alums – a very nice club to be in btw. We’ve longs since had that first impression thanks to TechCrunch (TechStars Debuts Nine Startups In Boston).

We’re actively raising funding. We’re working on our MVP. We’re talking to customers and users. We’re building our company. But now, now I’m going to take a bit of time to catch up on some of those things I wanted to talk about during the Summer of ’09, but just never had the time to.

Tom starting the startup, TechStars

So I’ve actively avoided the subject of TechStars since we were accepted last Spring.  The theory is that we don’t want to 1. toot our horn before we have something worth tooting about, and 2. we’ve been iterating so quickly through how exactly we’re going to change the world, that it’s best not to mention it yet.

Well, we’ve been outed. We knew it was coming and were fine with it, but it’s still a bit weird to see it in (lcd) print:  Fast pace, less funding define TechStars.

Here’s how it went down.  Galen Moore from MassHighTech was in the office and was asking questions – in the bathroom.   Once we moved the conversation a few doors away from the urinals, we chatted a bit about TempMine, what’s public and what’s not about our young company, and how awesome TechStars is.  Yeah, I’ve not just drank the Koolaid, I’ve bathed in it.

Galen must be good, because despite my brain saying “yo, you’re not ready to talk to a reporter”, the rest of me sure wanted to talk about TempMine and TechStars.  So I did.  He was kind enough to keep it general, but I’ll be looking forward to talking to him moew once we have more to say.

Tom starting the startup Press

So yesterday there was this post yesterday on news.yc “Ask HN: Startup founders, would you walk us through a day in the life?” that got me thinking.  What is my day like?

6:20am – One year old wakes up. Grudgingly, I do to.

6:25am – Change diaper, PJs if they’re wet, make a bottle, feed the boy, try to keep eyes open.

6:40am – Catch up on email on the iPhone while the boy plays on the family room floor. Can’t use the MacBook because he’ll want to play with it.

7:20am – Make coffee, clean the boy’s bottles, change his diaper.

8:00am – Wake up wife so I get to shower. Shower.

8:45am – Send replies that were too long for iPhone. Review where last night left us. Review what I want to get done today. Start working.

10:30am – motivate to the subway to go to the office. Pleasure read on the train.

11:15am – get to the office. Talk to office mates. Get situated, try to get back into the groove. Put off lunch as long as possible.

Lunch – try to find something cheap. Generally fail.

Rest of the day – work, have sessions with our mentors. Maybe get some dinner.

9:45pm – head home. Pass out on the subway.

10:30pm – Catch up with wife until she goes to bed.

11:00pm – 1:30am – Work.

Rinse, lather repeat and never second guess giving up that good 4 day a week job I used to have to start my own business.

It’s a pretty fancy life, eh?

Tom starting the startup a day in the life

So yeah, neither of us are graphic artists – that’s for sure.  When we needed to come up with a logo for some business cards from Moo, well, that fell on my shoulders (since I have a legit, real, honest copy of Illustrator – thanks former life in academia).  What we came up with is so not a logo.  It’s kinda just a font, with some color, but it’ll do for now.

So a version of it now lives up there, in the upper right.  That’s us, TempMine.  Neat.  Our biz cards look ok, not great.  Amusingly enough, I apparently messed up the color, so they’re a little darker, and purpleyer.  Whatevers.  There are first, and they’re kinda cool.

TempMine: our first business cards

Take away: Don’t waste too much time or money on your first biz cards.  If you pay more than $25 shipped, you’re wasting cash better used on anything else.  Also, don’t get too into the logo yet.  We’ll have way more time to worry about that later.

Tom starting the startup, Uncategorized business cards, design, logo, marketing