Taking the leap

To many I’ve talked to recently, this isn’t necessarily news . . . but about 7 weeks ago I left my very, very good job as a product manager at InsightSquared. InsightSquared is doing really well. And I enjoyed my 19 months there. But it was time to leave. I’m incredibly grateful to the folks at InsightSquared. Folks like Sam and Fred and Bryan gave me a ton of autonomy and a big challenge. But . . .

It was time to leave because I had completed that big challenge they initially had given me.

It was time to leave because it was a little too early to leave. And I’d never left a job too early. Always too late.

It was time to leave because I couldn’t shake the idea that it was time for me to challenge myself as much as possible and try to start my own company.

It was time to leave because my risk profile allowed for me to take a big risk this year. (By the way, my wife is really incredible and I am one super lucky guy).

It was time to leave because I am excited about trying to help folks with Fulfilled.

So I have turned my side project at Fulfilled (p.k.a Diseer) into my full-time job.

I’m currently working on Fulfilled full time, getting some help from some friends part-time and starting to build a product. We’ll see how it goes. If you want to keep tabs on Fulfilled, subscribe to the blog. Or even better, sign up to use the product when it is made available. Go on, sign up.

Louis CK, the scientist

So I’m doing some reading on the concept of context collapse and social media the other day for my work at Fulfilled.  And I hit this quote:

Social psychologists argue that we come to know ourselves by seeing what we do and how others react to us, and that through interaction, actors seek to maintain the identity meanings associated with each role.

This kind of stopped me in my tracks because it reminded me of this Louis CK clip:

The most relevant segment starts at the 1:25 mark. From Conan’s helpful transcript, when talking about kids and their mobile phones:

Louis C.K.: You know, I think these things are toxic, especially for kids. It’s this thing. It’s bad. They don’t look at people when they talk to them. They don’t build the empathy. Kids are mean and it’s because they’re trying it out. They look at a kid and they go, you’re fat. Then they see the kid’s face scrunch up and say ooh, that doesn’t feel good. But when they write they’re fat, they go, hmm, that was fun.

CONAN: That tasted good.

Louis C.K.: The thing is you need build an ability to just be yourself and not be doing something that’s what the phones are taking

The parallel between Louis CK talking about kids “trying it out” and the social psychologists talking about how we “come to know ourselves by seeing what we do and how others react to us” seemed like too much of a coincidence.

Either Louis CK is pretty well read on social psychology or he simply stumbled into this particular grain of truth when telling his jokes (like most good comedy). Given the forethought and planning that the best comedians put into their routines, I like to think it is the former.

My Current Side Project

Hello loyal blog readers,

Just a quick post to say that most of my deep thoughts outside of my day job at InsightSquared are being put down in writing at my new side project, Diseer. Head on over and check out my writing on you and your career path over at the Diseer blog.

So go on over there, check it out and let me know what you think.

2013 Chilly Half-Marathon Review

I ran, for the third time, the Chilly Half-Marathon. I’ve run this race the last three years.

You can check out my review from running the race in 2012 for a description of the race itself. It is a well run race. There aren’t too many frills — the start/finish line isn’t a carnival or anything. It starts early in the morning and it is nice that given the time of year, you can stay in the high school to stay warm.

I was generally pretty pleased with my time – 1 hr 40 minutes. It was 1 minute faster than my previous half-marathon (last year’s version of the same race). It was a personal record. It is not entirely surprising that my time only came down by 1 minute. My training hasn’t changed significantly over the last year. I prepared by doing the same program I did last year.

This was the first race I’ve ever run with my GPS watch so I can see bit more data about my performance. After a slow first mile warming up (8:11), the splits show that I ran pretty fast for miles 2 – 6. All but one of those miles were in the 7:30 – 7:35 per mile range. At this point, I was thinking to myself “Lets see if I can slice a big chunk more off my best time.”

Then the hills of miles 6 and 7 hit. This course has a tough stretch at this point with a steep, extended hill. I knew it was coming and I worked hard to power up the hill. My mile 7 pace drops down to 8:06 however.

Once the bad hills were behind me, I made a strong effort to return to my 7:35 pace. But by mile 11 I could feel myself fading and the hills had taken a lot out of me. I struggled to keep a 7:40ish pace the rest of the way. I passed a bunch of folks coming in the last mile or so, but was also passed by few as well. At the 12.5 mile mark I was really dragging and I did not feel strong at all — but powered hard for the last half mile.

I’d be interested to see what I could do on a “flat and fast” course. Maybe something in the spring. With some real hill training in my plan.


Paddy O’s Race Recap – 2013

Here’s a quick and belated recap of the Paddy O’s Shillelagh Shuffle. Mostly, I’m writing this to help me remember how the race went this year.

Since I started running in earnest, I’ve run the Paddy O’s 3 miler. At this point, I don’t particular care for short races and the pain associated to running a fast time. But I try to run this race annually because it acts as a nice benchmark. It helps me measure my short-distance pace general fitness and helps to trace a year over year arc since I started running. I also run it because it starts and finishes about 300 yards from my house. I can walk to the start line.

This was my third time running this particular race. The course is very flat and fast and it passes through residential areas. It is a 3 mile loop (not sure why they don’t make it a 5K).

This year, I was hoping to see improvement on my pace from 2 years ago when I ran the race wit a 7:28 mile pace. Given I ran a half-marathon with a 7:45 pace last year, I was confident I could do that.

This year, I forgot to bring my GPS watch but the race had timers calling out pace at the 1 and 2 mile marks. I was pissed when I hit the 1 mile mark and the timer called out 7:49. What the heck? That’s like a normal training run these days. What’s going on? I kicked myself into a higher gear. What I didn’t realize was that it had taken me 40 seconds to pass the start line at the gun. I was really running about a 7:10 for that first mile.

Anyway, I push myself harder for the 2nd mile and heard the timer call out 14:48 (gun time again, so close to a 7 minute pace for mile 2). And then kept the peddle down for the last mile. I didn’t have much of a kick left at the end, but finished up with a race time of 20:53, a 6:58 pace.

Overall, I was very pleased with the race. I was pleased to get my pace under 7 minutes. Two years ago, I ran at a 7:28 pace. Three years ago I was at a 7:36 pace. So I’m getting faster in my old age and have continued my streak of year over year improvement.

Chilly Half-Marathon Review – 2012

Last weekend I ran my third half-marathon — the Chilly Half-Marathon in Newton, MA.

This is the second time I’ve run this half-marathon. The 2011 edition was the first half-marathon I had ever tried.

In terms of the race, it is essentially unchanged from last year. It was again run in the early morning, starting from Newton South High. The course did not change. The course itself is pretty hilly, especially in the mid-section where there are some steep hills and we get to descend Heartbreak Hill from the Boston Marathon course.

This year, the weather was a bit warmer. Though the race was in the shade for much of the time, by the home stretch, the sun was shining and I felt the warmth of the sun for the last couple hundred meters.

Rather than (useless) medals, the finishers got running gloves. I liked it.

The race itself is recommended.

My performance

I was pleasantly surprised by my personal performance at this race.

I had battled shin splints most of the summer and took 6 weeks off from running from July through mid-August. I got healthy enough to squeeze in enough training to ramp up to two 12 mile training runs in late October. But because of the lay-off, the caution I exhibited in not training too hard coming off the injury, and the hilly nature of the course, I didn’t expect to improve upon my time from last May at the half-marathon in Gloucester.

I ended up running the race in 1:41, or a 7:45/mile pace. This is 13 seconds per mile faster than my previous half-marathon. I dropped my time by 4 minutes or so.

I attribute my much better performance here not to better training, but to better racing. My general MO in road races has historically been to take it easy in the early stages and then gradually build up my pace. In each of my half-marathons prior to this one, I had a lot of kick left in my for the last two miles and came in faster than the others on the course with me, passing lots of folks.

This time, I had a better feel for my capabilities and ran the first half of the race at an 8 minute/mile pace. I forgot to bring my GPS watch, but a fellow runner gave me the data data point of 39:30 at the 5 mile mark. I basically ran the entire race with people at my ability.

In this race, I didn’t pass many folks in the second-half of the race, and was passed by a few. I was still able to pass folks on the hills, but many fewer and some would pass me back on the down hills.

Once I hit mile 12 or so, I was passed by a woman in a pink running top. I figured it was time to turn on my usual end of race kick and pass her back. But when I tried to turn it up and leave nothing on the course, I didn’t find any more speed. I couldn’t catch her for the last mile or so. I tailed her and finally passed her in the home stretch when I sprinted.

What’s next?

Probably more half-marathons. I figure I’ll need to do some more speed work to continue my trend of half-marathon improvement. I also think I need to figure out how to run the downhills with less effort and more speed.

I’ll look for more to do either this winter or the spring. Open to recommendations for local races. Any ideas?

4 Lessons Learned Working at HubSpot

After two great years, I left HubSpot last month.

I’m not sure what’s next, so don’t expect a forward looking just yet. Right now, I’m focused on taking stock of all the things that I learned from HubSpot, all the great folks with whom I collaborated and the new perspectives on the software business I gained. HubSpot is an incredible place — I learned a ton. Here, mostly for my own documentation, are a few of the key lessons that I either learned or were reinforced working at HubSpot.

1. Be unafraid to make aggressive changes

This is the thing I would emphasize more than any other. At HubSpot, things are generally going well. Its no secret the business is growing. I think one of the reasons it continues to grow is that leadership team is unafraid to tackle problems with big changes. They don’t save big changes for when the business is facing big, threatening problems. They are aggressive in solving the monthly/quarterly problems with bold change. It pays off.

2. Transparency empowers

I have never ever worked at a place as transparent and open as HubSpot. Virtually everything you’d want to know about the business is known and shared on the HubSpot wiki. To paraphrase Dharmesh, you need to have a really good reason to  keep something a secret at HubSpot.  With more people empowered with more information, better ideas are generated, millions of small decisions are better informed and the business just runs smoother. People trust each other with open transparency.

And this extended to our relationships with our customers. We were able to more effectively work through problems or changes with the product by being 100% honest with our customers at HubSpot. The more they were informed, the more our customers trusted our judgement and accepted changes to the HubSpot product.

I loathe the prospect of ever working somewhere that wasn’t as transparent and open as HubSpot.

3. The answer is always “ship it”

Hat tip to David Cancel here. As a product manager, you’re not always sure when to ship something or take the next big step. And the answer is almost always “ship it”. Should you wait for the next round of imminent improvements to the tool? Do you wait for another round of performance improvements? Do you wait for the next round of UI tweaks? Don’t wait. Ship it. Those improvements might end up being the least important thing you should be focusing on. Your priorities need to be customer focused. And if you are teetering on making something more widely available, just ship it. You’ll learn from your customers if your priorities are right.

4. Use good judgement

This one comes from observing Brian Halligan. Occasionally there would be some cultural question or some HR policy debate that would bubble up. And eventually, Brian would weigh in with his “ruling”. And it would almost always be “use good judgement”. Should you come into work when you’re sick? Use good judgement. Should you come in when its snowing? Use good judgement. How should you behave on social media? Use good judgement.

If you have adults at your company (and having aged a certain number of years doesn’t mean you are an adult — I forget where I stole this idea from), trusting them and empowering them to make their own decisions ensures happy employees, and usually the right outcomes.

(Ex-)Hubspotters, what did you learn?

Twin Lights Half-Marathon Review – 2012

Today I ran my second half-marathon — the Twin Lights Half-Marathon in Gloucester, MA. Overall, it was a great experience. Really, no complaints.

I chose this race since it would provide nice excuse to go see my parents who have a house a few blocks away from the starting line. The course ran from Good Harbor Beach in Gloucester, up the coast north into Rockport. It was a lollipop route, running a loop around scenic Rockport and then coming back to Gloucester on the same road. We caught sight of the ocean throughout the race, also running through some residential neighborhoods and quant downtown Rockport. There was a nice ocean flavor throughout as the homes seemed to either be vacation homes or filled lobster traps.

The course had some hills, but it wasn’t nearly as hilly as the first half-marathon I ran last fall nor the roads in Newton where I train. The hills at around mile 7 and mile 10 weren’t too big, but well timed as part of the course to really push you.

Because of the lollipop layout of the course, there was always lots of water stations — the stations could pull double duty for going out and coming back in. The course almost always had a nice smattering of spectators which always helps.

The setup at the start/finish line was just right — lots of bathrooms, water and gatorade and lots of food at the end, but not too much of a circus. Access to the Good Harbor parking is always slow so plan on it taking 15 minutes to drive the last 1/2 mile.

In terms of my own performance, I was pretty pleased. I finished in about 1:44 — my pace was a shade under 8 minutes/mile (7:58). This was faster than my previous half-marathon by about 4 minutes overall and 17 seconds/mile.

This time, I didn’t go out too slowly — covering the first two miles in about 16:20. I kept the pace pretty steady throughout. I also warmed up a bit for the first time before a race, doing a light jog for about 1/2 mile 30 minutes pre-start. I think that helped me at the outset kick into gear. At about mile 6, I fell in with a nice fellow from Pembroke named Troy (a minister). We ran together and chatted for a bit. We really cranked at this point, he estimated we were doing a 7 minute/mile pace but then he fell behind at the hill at mile 7 (the endorphins really kick in for me at mile 6).

Just after mile 11, I passed a woman named Macaleigh. She didn’t take that too lightly and pulled right back up next to me for the remainder of the race. We chatted through to the end which helped both of us, I think. Just at 13, I was starting to fade, she gave me a bit of encouragement and I powered home (even outkicking her in the last 300 meters).  The support of the other runners was great. Its one of the reasons I love running.

Now I’m on the prowl for another race. I had been planning to do the Chilly Half again in November . . . but that seems like a long time to wait. Any good half-marathons in the next 8-12 weeks?