Category Archives: hubspot

Summer 2015 update

Hard to believe it’s been almost 10 months since I last blogged: September 30th, 2014. It’s been among the best 10 months of my life, happily filled with much growth, satisfaction, adventures, and smiles.

One of the reasons I’ve been blogging less is that I’ve been using other social media tools more. Many things that would have been blog posts in the past now go to Instagram or Twitter. I think I’m actually creating more content, not less, but in smaller pieces.

The blog is still useful for longer pieces of writing, of course. But I no longer have any illusion about regular posting here, and don’t want to set any expectations.

The last 10 months have brought some significant events, all positive.

First and foremost, I got married 🙂 Lisa is amazing, and I couldn’t be more excited for our future together.

At the 2015 SuperBowl in Arizona.

Silly tourists driving around Santorini, Greece.

At our wedding on Boston’s Charles River Esplanade.

I also want to congratulate my HubSpot (NYSE: HUBS) colleagues and friends on their successful initial public offering last fall. It was a great journey, with many smart folks working hard, working together, for a remarkable outcome. I feel #blessed that something I helped start grew into a world-class company. Thank you to everyone involved, now and in the past.

Picture from a BetaBoston article by Dennis Keohane.

I thought the above IPO would increase my desire to retire, or at least significantly relax/chill out. Strangely, the opposite has happened. I’m as driven and hungry as I’ve ever been, maybe more so.

Work at Jana is going well: we’re making great, measurable progress on an awesome mission/vision.

Want to know why they’re wearing wigs? Ask me. We’re hiring 🙂

I’ve been working and traveling enough that I think my fitness has suffered this year. But that’s been a relatively known/calculated sacrifice for other good causes. Overall, I’m really lucky and blessed, can’t complain at all 🙂

Happy summer, everyone!


Last week was busy but fun

Quick recap of last week, which ended up being slightly busier than planned, and as usual, made awesome with stellar company.

Went to the new Belly wine bar / gastropub in Kendall Square on Monday with a friend. We’re both foodies and she’s also industry, so we showed up early a day after they opened, chatted a bunch with the staff, and had a great time. I love their idea, want less Beaujolais on the menu, and wish they took reservations.

Belly before the crowds.

The charcuterie and cheese options at Belly were very good.

After that I met another friend for dinner at Vejigantes, the Puerto Rican place in the South End. There too the food was delicious, and the Coronamea was a fun drink combining a margarita with a Corona. I didn’t drink too much, since I had a 5:30am wakeup the next morning to run the stairs at Harvard Stadium.

A Corona – Margarita combination…

The November Project is one of my new favorite things in Boston. I actually joined before my trip, but it’s become a regular thing now for me, and the group has grown a lot too. It’s free, open to the public, friendly, welcoming, and has many fun folks. Three workouts a week at 6:30am, rain or shine, all weather, all seasons, and they’re each hard. I don’t do the Monday morning one, but Wednesdays at Harvard Stadium and Fridays at Summit Ave are a ton of fun.

I started and finished before the main group, which you can see above.

Last Wednesday I set a new personal best for the “full tour,” i.e. once around the entire Harvard Stadium, which always feels great. It’s a brutal workout, maybe the hardest one I do all week. It has not been getting much easier. I wonder how many people will drop as the weather turns wintery.

On Thursday after some morning business, I joined a friend down in Newport, Rhode Island, for an afternoon of polo. I had never seen it in person, and it was interesting, entertaining, and fun. I forgot that each player has multiple horses, or ponies as they’re called, leading to a whole bunch of horses being around waiting for their turn to play.

Gaucha, a friendly well-trained horse.

While I can’t ride well and can’t play polo well at all, this was still a fun experience, especially observing my friend play. Unfortunately I had to leave early-ish to drive back to Boston, missing the post-match BBQ.

I had dinner that night with another good friend and business colleague at Myers & Chang in the South End. I hadn’t been in a while but remembered how much I liked the braised pork belly buns. Having just been to Hong Kong (more on that in an upcoming #rtw2012 post), I wanted to compare — and these stacked up very well.


The next morning, Friday, brought another 5:30am wakeup for the November Project. This time we ran up and down Summit Ave, one of the steepest streets / hills in the Boston area. Years ago I had a tough time walking up this hill, and for a long time I couldn’t run up it. On Friday I helped pace a bunch of people on it, which felt great. Progress is being made…

Brogan’s pic, not mine, from the hill on Friday morning.

That evening the big event was Paul Oakenfold at Royale, but we grabbed some tequila and dinner at Tico first. I love their crispy pork bellies — so good! And a nice selection of tequila as well.


Oakenfold was excellent. He’s become a bit more mainstream, a bit more Guetta-ish in style over the years, but his technical skills and track selection, as well as crowd reading and reactions, remain top-notch. Without much advanced planning, I’ve now seen him, Paul van Dyk, Tiesto, Armin van Buurden, and John Digweed live this year, plus a handful of other notable DJs. It’s been a great year in that regard.



After Royale closed out, we stopped by Rise, the private after-hours club, for a bit of harder trance. That was fun, as always. (And as usual, I didn’t take pictures inside of rise.)

The next day, a Saturday, I went for a short run that turned into a 10K, and then a 5K row in the Charles river, taking advantage of the beautiful weather. Unfortunately I only did this on 2.5 hours of sleep, so it was more of a challenge than usual, but perhaps a good simulation for Ironman conditions.

Another gorgeous September day on the Esplanade.

After that I met a couple of my best friends for lunch at Xinh Xinh, the lovely authentic little Vietnamese place in Chinatown. I had some excellent pho-type noodles, #33 on their menu, a seafood special stew noodle thing.


From there I met up with another crew for the Michigan football game, at Sweet Caroline’s near Fenway Park. I didn’t realize this was the “home bar” of all Boston-area (or even wider…) Michigan alumni and fans. It’s official, with banners and people dressed up and everything. I caught a good video of some cheering after a touchdown, and enjoyed the game atmosphere, even though I have no particular connection to Michigan.

After the game we went down Boylston Street to Sweet Cheeks, as I was craving BBQ. Like any good Jew, I got pork ribs, pork bellies, and pulled pork. We also shared some awesome biscuits. One member of our party, the guy who had the best role in this week’s HubSpot “Gangnam Style” video, is from the southern US, and he testified as to the quality of the food at Sweet Cheeks.

Saturday night needs to stay off this blog, I think 😉 At least for now.

But then Sunday was also great, as I went with a friend to the Patriots home opening game. We had solid seats down near the field, and it was a beautiful day. Unfortunately the Pats lost in an upset 😦 They deserved to lose, and I hope they learn some lessons, improve fast, and win the rest of their games. This week at Baltimore will be tough.


Whew, it was a busy week. I did get about 45 hours of work in, too, including a bunch of open-source contributions. Sunday night I slept for about 11 hours straight 🙂

Life is a marathon, not a sprint

Today is the 2012 Boston Marathon, a race with a lot of tradition, memories, intensity, heartbreak, and happiness.

And this post turned out to be long, almost like a marathon 🙂  It’s a personal post, no tech interest.  You may just want to skip it unless you’re bored… No tl;dr provided on purpose.

One of the things I always liked best about the marathon, which is not unique to Boston’s, is how the non-elite runners (like me), people who’d never win the race, can still get so much joy out of simply completing it.  Completing, not competing.

But, as with most sports and other professional activities, it’s at least as much fun for me to observe the elite runners, the ones who train their whole lives for this (and similar) races.  They are faster, stronger, more consistent, and better in many ways.  We watch and try to learn, or at least be inspired, by them.

There are many similarities (and many differences) between training for a marathon and working at a company that is trying to be world-class, like HubSpot.  Success in both areas requires dedication and intensity, but also an open mind to new training techniques, flexibility in dealing with change, and more.

I could go on and on about the similarities and differences: skill specialization, individualism vs teamwork, training approaches, burnout, the importance of coaching and advice, the impact of technology and equipment, and more.

But that’s not my main point for this post.  The main point is that life itself is a marathon, not a sprint, as well.  After nearly five years of running at sprint speed at HubSpot, we parted ways earlier this month.

HubSpot was far more than a job: it was a huge part of my life during this time, as my family and friends would gladly tell you.  I learned many, many valuable lessons from my colleagues, our customers, my teammates, and my own work, both successes and mistakes.  I hope I helped the company grow and become the juggernaut it is today.

I am very grateful to Brian and Dharmesh, HubSpot’s co-founders and my bosses, for giving me the freedom to learn, to grow, to experiment, to build, and to try and help make HubSpot the best marketing software company in the world.  Thanks, guys!

I could not be more confident in HubSpot’s future.  The company is crushing it on many levels, and it continues to get stronger, hiring amazing talent in all departments, improving the product, getting smarter, more efficient, and becoming an imposing machine in many ways.  And that’s before the new COO, JD Sherman, is really settled in: I think he will be a tremendous positive impact on the company.

If I could buy more HubSpot stock, I would.  If you have options, exercise them.  (Try to avoid the AMT…)  If I start my own company and need to raise money, hopefully these guys will invest, thereby starting a “HubSpot mafia” in the PayPal style.  We are friends in the special way that people who’ve fought in the trenches together for years can be, and I cherish my time with them.

One of the many reasons I joined HubSpot was to learn about sales and marketing from two fellow Sloanies who seemed reasonably sharp at the time: Mike Volpe and Mark Roberge.  I got more than I bargained for there, as they turned out to be world-class doers, thinkers, managers, and businessmen in their domain, all while being Good People.  We, too, are good personal friends and will remain so.  Thanks for teaching me a ton, guys, and leading by example the whole way.

Our monthly management meetings were a great source of learning.  My colleagues David Stack (our CFO), Jonah Lopin (head of services and customer success), Jim O’Neill (our CIO, but really jack-of-all-trades, problem solver, party host, and more…), Arjun Moorthy, Brad Coffey, and recently-but-awesomely, David Cancel, are an amazing group.  If you sit down in a room with them for a day, no matter what the topic might be, you will learn a ton, guaranteed.  Thanks, guys!

I obviously can’t name everyone at HubSpot, as I like and have learned from (literally) hundreds of people, and this post is already very long.  Many of them will be life-long friends, spanning jobs, industries, personal life changes, geo re-locations, and more.  You know who you are, and you know I’ll be there for you.

To the awesome engineering crew, thanks for all your work building towards a great product.  I hope not too many of my bugs remain in the code base 🙂 As I’ve told a number of folks, I am always available to help.  Just reach out to me 24/7, and I’ll gladly help.  I’ve learned just as much from you as anyone else, and I’m grateful for that.

During my last year at HubSpot, I worked mostly on our platform and marketplace initiatives.  Those projects have high potential not just to delight many more HubSpot customers, making them into marketing stars, but also change a relatively closed segment of the software industry into something more collaborative, more modern, more appealing, and more valuable.  Of course, I’m biased, but this is why I chose to work on them 🙂

As for what’s next for me?  I don’t know yet.  I wasn’t looking around while at HubSpot.  I’m taking a little bit of time to chat with folks and explore the many available options.  I’m lucky to have some reasonable skills in a decent market, and an open mind.

But I do plan to travel a bit, to relax and recharge, before starting to crank on the next thing, whatever and wherever it may be.  It’s kind of like walking half a mile in the 26.2 mile marathon.

One of the most important lessons I learned over these years was a hard one for me to digest and implement.  It’s summarized by Winston Churchill, but the key is that he’s not only talking about speaking in the verbal sense, but in our actions, our choices (career and otherwise).

Courage is what it takes to stand up and speak; courage is also what it takes to sit down and listen.

Stay courageous, and stay tuned 🙂

Yet another reason Brian Halligan rocks

It’s not often I write a blog post about a specific individual, but this guy deserves a special public shout-out.

Our co-founder and CEO, Brian Halligan, is awesome.  There are many ways in which he’s awesome, and it’s been acknowledged with assorted awards, but this post is about two specific reasons not often mentioned.

One is that Brian is willing to trust people with things he doesn’t fully grok right away, and give them the freedom to experiment and innovate.  This is more rare than it sounds.  Most CEOs I’ve known are too arrogant, or too afraid of looking clueless, if they allow things they don’t fully understand to go on.  Brian, on the other hand, looks to hire smart people, trust them, and work together with them as everyone grows.  This is great.

Two is that although Brian has a vision for HubSpot, and he largely created that vision with Dharmesh, he’s not afraid to see it change.  He’s humble enough to evolve with time, modify the vision, adjust, innovate, and grow.  This, too, is rare and appreciated.

My new(ish) team at HubSpot, the Platform team, would not be possible without both of these personality traits in our CEO.  It’s an expensive team with a bunch of good folks, doing work whose impact is in the long-term.  Sometimes it’s hard to tie our work to immediate goals, whether they are sales goals or otherwise.  But Brian has had faith, patience, and the ability to change and adjust.

The winners are our customers, first and foremost, but also our employees.  This blog post summarizes one of my top, most important reasons for joining HubSpot, for staying here, and for recruiting other friends and colleagues.

I hope you’re lucky enough to work for a CEO as clueful as Halligan in your professional career.  They’re rare.

Thanks, Brian!

Changing roles at work (HubSpot)

I am changing my role at HubSpot to focus less on day-to-day management, HR, and product-centric efforts, and more towards creating a “HubSpot platform” for internal and external developers to build on.

That’s a mouthful 😉  Let me explain in a little more detail, both what I’ll be doing, and why I’m making this change.

For about three years now, I’ve been HubSpot’s VP of Engineering.  In that role I did a lot of recruiting, building a team that’s several multiples bigger than when I started.  We grew from dozens of customers to thousands of them, created a variety of new products, improved existing ones, learned about process and agility, and it’s been a fantastic experience.  I put in place and managed the entire product development process, structure, framework…  It was fun.

But for a while now, I (and several other people inside and outside HubSpot) have felt that although we’re a great sales and marketing company, engineering has been mostly a supporting role.  I want to change that.  I want us to drastically grow our technology chops, start working more with the outside world of developers, and in the process improve our product as well as the lives of HubSpot customers and HubSpot’s own developers.

There is a range of projects in the queue, from internal-facing scalability and reliability improvements, to external-facing APIs and integration opportunities.  I look forward to handling the technical challenges as well as the ecosystem-creation and business development ones.  And since I’ll be managing way less people directly, I hope to have much more time for hands-on coding and development, which I sorely miss.

HubSpot has a very broad, sweeping vision and goals.  It’s unlikely we’ll ever have enough developers in-house to fully realize the extent of our vision.  Even if we did, there would always be more ideas than we can implement.  Many industry-specific or customer-specific types of needs, we are unlikely to address in our core product.  At least not for a long time.  I’d still like those people to be able to use inbound marketing to their advantage, and the platform should help them.  We already have a variety of partners and interested parties queued up to start working with us.

The transition will be gradual and it will take a while.  We couldn’t do it at all unless we already had another fantastic engineering leader at HubSpot, in the form of Jim O’Neill.  Jim is in my top five colleagues I’ve ever worked with, a true personal friend, and I trust him completely.  Otherwise this move would likely be impossible: finding someone from the outside for this role is incredibly tough.

As a HubSpot shareholder, I’m excited about these changes.  Dharmesh, Jim, and I have actually been talking about them for months.  I also sought advice from a couple of great HubSpot friends (and Board members), David Skok and Andy Payne.  They were extremely helpful, as always.

It will take a while, but I hope this transforms HubSpot in the future.  HubSpot Inc v2.0, if you will 😉

By the way, we’re hiring smart engineers 😉  If you want to join us, please get in touch.

Happy birthday HubSpot!

Yesterday almost everyone at HubSpot went out to celebrate the second birthday of our internet marketing company. Alyssa and Ellie did a great job organizing the event, as they always do, and I had a blast. I think everyone had a lot of fun.

We went out to Kings for some food, drinking, and bowling. Apparently we have some ringers who are better bowlers than expected. I did just OK, but then again I bowl roughly once every 3 years, so my expectations are low. Team spirit was evident throughout the event, which was cool. And the new people are blending in really nicely.

We posted a bunch of pictures of Flickr if you’re curious.

Happy birthday HubSpot!