Happy Birthday, HubSpot! 15 Lessons Over 15 Years

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15 years ago today, on June 9, 2006, HubSpot was “officially” started. I say “officially”, because unofficially, I had been noodling on the idea of HubSpot for a couple of years with my co-founder, Brian Halligan while we were both classmates in grad school. I picked the June 9th date, because that’s the official date that I graduated and was no longer a student. (Brian graduated a year ahead of me, and I was still working on my thesis).

I don’t have a lot of photos from the early years, because as it turns out, neither one of us are big “photo people”. But, here’s one of us celebrating HubSpot’s 2nd birthday.


In the past 15 years we’ve had a bunch of fun and learned a ton (rhyming unintended, I’m proud of myself for resisting the temptation to try and turn that into a poem). The company has grown significantly from the two founders (and a house plant named Duo) to a globally distributed company with 4,000+ employees that’s publicly traded on the New York Stock Exchange with a market cap north of $20 billion.

I thought I’d share some of the lessons learned.

Note: These are in no particular order, because I wasn’t sure what sort key to use.

15 Somewhat Humble Lessons From 15 Years of HubSpot  

Build a diverse team early. Of the many professional mistakes I’ve made, not doing this is one of the biggest — and the one I most regret. Candidly, back in those days, we didn’t think about diversity — or for that matter, the broader topic of culture, all that much. But we should have. When you build a mostly homogeneous team, you incur culture debt. And much like financial debt and technology debt, you’ll have to pay it off at some point. But, whereas financial debt can be paid off by writing a check and technology debt can often be paid off by rewriting/refactoring parts of the system, culture debt is much more insidious. It’s really hard to pay it off completely. Try not to take on that culture debt. Your future self will thank you.
Instill a “customer first” mindset and implement mechanisms to foster it. We did pretty well on this. Solving For The Customer has been part of our culture from the early days. We have several mechanisms that help us walk the walk, and not just talk the talk. Examples include having a live customer interview at the start of every company-side, all-minds meeting. We do an NPS survey of our customers — nothing remarkable there. What is remarkable is that we pipe the live responses directly into a dedicated Slack channel.  Over 1,000 people at HubSpot are subscribed to that channel (on a voluntary basis). We maintain a list of what we call “sharp edges”. Decisions that we made along the way that were not as customer-friendly as they should have been. Every year, we work to try and smoothen out those sharp edges.
Good intent is necessary, but not sufficient. Good execution is what pays the bills. We’ve had this GSD (Get Sh*t Done) attitude since Day 1. We’ve always been very execution oriented. Part of this was by necessity. We didn’t have the luxury of some brilliant invention or non-reproducible that would carry us. We had to push to get through.
Learning culture through osmosis stops working pretty quickly. The degree to which people learn by osmosis about the company culture down as the number of people go up. As early as possible, you need to write the culture and values down. It doesn’t have to be a deck with 128 slides, like HubSpot’s Culture Code (v1 of the deck was 16 slides) — it can be a single sheet of paper (I hear those still exist), or even a napkin. But you need something. And that something has to be articulated in collaboration with the team. Otherwise, there’s high risk of it just turning out to be words.
Transparency is scary — but spectacularly effective. It’s scary, because there’s always the risk that someone abuses the trust. But there are many upsides. First, the best people (you know, the ones you’re trying to recruit) value transparency, and the degree to which they value it has continued to go up. Second, transparency is efficient. It makes a lot of things easier when you don’t have to spend hours and hours debating who should have access to what information. It’s why at HubSpot, we share everything with everyone on the team — and have since Day 1. If I could do it all over again, I’d do it in a heartbeat. Or should I say, HEARTbeat?  (Inside joke, sorry).
More companies die of co-founder conflict than any other cause. To minimize that risk, choose your co-founder(s) wisely. The most important thing is not their skillset — it’s mutual respect, admiration and dare I say love. (Hi, Brian, love you dude!).  Apologies for the PDFA (public display of founder affection). That’s not usually my style, but I have my human moments every now and then.
Though it’s fun to create a new category, it’s not always necessary. Elon at Tesla didn’t create the electric vehicle category. Tobi at Shopify didn’t create the eCommerce category. HubSpot didn’t create the CRM category. But, one thing we all did do is helped a bunch of people that might not have been experiencing the benefits of that product category before, start to do so.Note: In our early years, we did create the “inbound marketing” category — and though that helped us with growth in the early years, it was hard, expensive and risky. I don’t know that I’d recommend it for everyone.  
Believe in your team. If you have an ambitious dream (we certainly did), keep pushing towards it and give your people the autonomy to try — and sometimes fail — in the pursuit of it. They will surprise you with spectacular feats of awesomeness.  One thing I’ve learned, is that Brian and I usually have our dreams and wishes come true — but not always when we want them. Often, things take time. Great ideas can often take years to crystallize into reality. And, it’s not always obvious that an idea is great.
Push yourself and the team to take smart risks. This gets harder and harder to do as you scale, but it’s critical. The natural way of things is to get increasingly risk-averse, because the bigger you grow, the more you have to lose. That’s why, you have to push to make bold bets. They don’t’ have to be bet-the-company scale bets, but they need to have a chance at being spectacularly impactful.
Be rationally generous. Always try to add value before you try and extract it. It’s OK to leave some money on the table. You don’t have to always try and maximize how much of the consumer surplus you capture. It’s OK to let your customers and partners benefit. It’s OK to charge less than the value you create — or even the value that you could reasonably negotiate.
Avoid cynics — they are toxic, energy sucking vampires. I’m not talking about skeptics here — I’m talking about cynics. Skeptics will often push and question and play the devil’s advocate role. But, they do it because they want to make things better. It’s important to have some of those people on the team. Cynics on the other hand are profoundly negative because they don’t believe people/organizations can have good-intent or motives. Deep down inside, they don’t believe the organization will improve or get better. You get bonus points for recruiting smart people that are energy accretive and lift everyone’s mood. They’ll make you happier too — life is short.
Your long-term success will be defined by the “systems thinkers” on the team. These are the folks that like to analyze things. They are bothered by manual processes. They are always looking for leverage (i.e. finding clever ways for seemingly small things that can have disproportionate impact over the long-term). They are pattern-seekers and puzzle solvers. Note: When I say “systems”, I don’t mean just technical systems — and I”m not just referring to engineers here. This applies across every department and every discipline. Find and foster the folks that think in frameworks and flywheels.
 Most things are learnable skills both at a company level and an individual level.  When someone has “natural talent” for something, all that usually means is that they’ll be able to acquire that skill with less time/energy expended. But, if you’re willing to do the work, you can get pretty good at whatever you choose to do. Even for the company — acquiring a particular skill (or “building a muscle”, as we say in HubSpot) may be hard, but it’s usually not impossible. You just have to figure out which hard skills are worth acquiring. At HubSpot, we started being really good at marketing and sales. Then, we deliberately decided to invest in making an amazing product. In our early years, we were really good at inside sales. A decade later, we decided to invest in getting really good at freemium and product-led growth.
 Learn as much as you can, from anywhere you can, constantly and forever. Don’t be a know-it-all, be a learn-it-all.  (I got that from Brian, who got it from somewhere else).  It’s tempting to think of ourselves and our companies as these special little snowflakes — and we are. But that doesn’t mean there is not wisdom and insight we can draw from others and pick the ones that feel like they might work in our business. At a tactical level, strongly encourage people read books. Long ago, we implemented a free books program whereby anyone at HubSpot can get any book that will help them learn and grow. Company picks up the tab. One of my favorite things that we’ve done.
 Align your vectors. Make sure that at every level of abstraction things are aligned. Make sure each person is aligned with others on their team. Make sure each team is aligned with the mission of the company. Make sure the company’s mission is aligned with the interests of the customer. The magic of increasing alignment is that you can get more progress while holding both the number of people — and their average competency, constant. Let me say that one more time for dramatic effect: You can take the exact same people and keep their skills exactly the same, and get better outcomes, simply by improving the degree to which they are aligned and pointed in the same(ish) direction. I’ve written about this in more depth on this topic here. Aligning Vectors To Optimize Impact.

Phew!  Once I got into flow, the thoughts flowed more easily.  I’ve got more in my head, but will save that for another time. I believe in “release early, release often”.

Read more: onstartups.com

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