Dec 30, 2015 · 10 min read

David Cancel is a 5x founder and 2x CEO with four successful exits to date. Currently he’s co-founder and CEO of Driftt, where he’s helping marketers transform their relationships with customers to drive retention & growth.

David previously founded Compete, Lookery, Ghostery, and Performable. Most recently, after the acquisition of Performable by HubSpot ($HUBS), David was the Chief Product Officer and responsible for re-architecting the engineering team and HubSpot’s products.

He’s active in the Boston tech community investing in and/or advising organizations like Charles River Ventures, Spark Capital, NextView Ventures, DormRoom Fund, EverTrue, Visible Measures, Yottaa, and HelpScout. David was born and raised in New York City and now lives in the Boston area with his wife and two kids.

Members of GrowthHackers.com recently asked David (or DC, as Driftters and friends like to call him) about everything from startups, product teams, entrepreneurship, sneakers and more. The slightly edited transcript is below.

He even wore his favorite pair of Jordan’s just for the occasion:

How difficult was it to become an executive for a big company when HubSpot acquired Performable after 10+ years of being a founder at smaller companies?

When Performable was acquired we were about a 20 person company and HubSpot was a 200 person company. Like most founders I’m not great at “being told what to do” AKA I’m usually a troublemaker in a larger organization.

The adjustment was hard but HubSpot was not your average company. The only reason I agreed to the acquisition was because we shared the same vision (to build a once-in-a-lifetime company) and the same values (culture, speed, question conventional wisdom, etc). Because of all of this it was easier than it should have been.

Also my mission at HubSpot was clear: rebuild the product, engineering, and design organizations, and rebuild and expand our product as we moved from SMB to serve the mid-market and beyond.

It was an epic mission and I never regretted the decision for a day, but now it’s time to get back to the grind and start something from nothing.

I will add that one of the things I wanted to learn was how to scale a company from 150 people to a 1000 people. The largest any company I had founded ever got was around 150 people with Compete. I wanted to learn how to scale beyond that.

During my time at HubSpot we grew from 200 people to a little over 1000 people. From one office to 3 offices (2 international). And from around 2000 customers to more than 15,000 customers.

These are all scaling points I wanted to learn. I’m thankful to have learned that at a once-in-a-lifetime company.

You have beat the statistical odds of startup failure by creating 5 successful companies. What do you do in your ideation phase, execution phase and scaling phase that is contrary to most other entrepreneurs?

First, I’m lucky and I make a point of being grateful each morning for what I have, most importantly my family 👨‍👩‍👦‍👦.

As an Introvert (INTJ), I think I’m good at being self-aware. I think I have a good handle on my strengths and more importantly, I know my limits.

As Tom Watson Sr., who started IBM, said “I’m no genius. But I’m smart in spots, and I stay around those spots.’ And, you know that is the key. So if I understand a few things and stick in that arena, I’ll do OK.”

The most important thing I think that’s helped me is that I focus on PEOPLE over everything. I started out as a software engineer. It’s more comfortable for me to sit behind a screen and code all day but I recognized early that if I wanted to have a big impact I needed to understand and get good at dealing with PEOPLE.

Over time I think that’s lead me to build companies centered around the CUSTOMER which is key for me. It’s also led me to build what I think are above average teams who are empathetic with the CUSTOMER. If you have those two things it is easy to win.

Like most things in life the answer is SIMPLE but not EASY. People want to spend too much time on process, building, and just staying busy. There’s a time for each of those things but it starts and ends with PEOPLE.

What is the most important thing you do each day?

No contest: Spend time with my family.

After that is my morning practice (do all of the below before touching a phone/computer):

1. Rise early: 5–5:30am
2. 15–20 mins of Yoga (at home).
3. 5 Minute Journal: What would make today great? What am I grateful for?
4. Read a Book: 15–30mins
5. Eat breakfast with my family.
6. Now I can touch a laptop/screen

After spending time ith my family and my morning practice: Focus on one big goal for today for Driftt. Stephen Covey’s lesson on Big Rocks vs Little Rocks is my template here. All my energy on achieving one big goal today. After that I spend time with my team, customers and mentors.

FYI this is the theme song from this AMA 🙌🙌🙌🙌🙌

What do you believe is/are the most unique advantage(s) of the Boston startup ecosystem? Also, what are the top 2–3 things a startup founder moving to the Boston area should absolutely do take advantage of the resources available?

Unique advantages:

1. It’s f’ing cold here yo. That means less time at the beach and more time grinding. Extraordinary results *require* extraordinary efforts. Simple, not easy.

2. Talent. Boston is UNTOUCHABLE when it comes to its education system. The hard thing is keeping people away from the lure of the beaches and warm weather elsewhere 😉

Top things for founders moving here todo:

  1. Don’t waste time running around meeting people and going to meetups.
  2. “Show me”. Start grinding and earn the right to get out there and start talking to people.
  3. Spend time getting to know the universities. Most of the people you want to recruit will come from them. Start building your pipeline.


Pick 3 books that every entrepreneur should read in 2016 if they haven’t already.

Hard to choose 3. Also hard to choose 3 that you haven’t read yet.

Here’s a quick shot:

1. Total Recall: My Unbelievably True Life Story — Amazing story of a man who was able to achieve every big goal he focused on. Bodybuilder, Hollywood Star, Married a Kennedy, Business Man, and Governor. Wow.

2. The ONE thing by Gary Keller. I bought this book for everyone at Driftt this year. Read it with a highlighter ready.

3. Zingerman’s Guide to Giving Great Service.

Theme across these books: Pick one BIG ROCK and focus on it until you acheive that goal.

Bonus: You must have a copy of Seeking Wisdom: From Darwin to Munger, 3rd Edition on your nightstand.

Do you regret having so many exits and not building a single company for a much longer time or was this intentional?

Regrets? Never. Not even once.


I live in the present. I don’t spend much time regretting the past or much time thinking about the future.

I focus all my energy on trying to make today count. We aren’t promised tomorrow. Make today count. I start my day remembering that simple cliche and it makes all the difference.

That being said I’m doing thing differently with Driftt. I want to build a once-in-a-lifetime company with Driftt. My goal is to build an anchor company here in Boston that will outlive all of us.

I am swinging for the fences at Driftt. I have no interest in being acquired at Driftt, we are going “all in”.


What, in your mind, is the best (programming) learning roadmap for an aspiring PM/CTO? What skills/personalities do you look for when interviewing programmers/engineers? How did you re-architect the engineering team at HubSpot and what are the lessons you learned during that time?

1) If you’re an aspiring PM I don’t think you need to learn how to code. Feel free to do it if you find pleasure in doing so but I don’t think its’ core to the job.

You need to leave “the solution” to the engineering team. As a PM you need to focus on owning “the problem”, aka finding/validating the problem and helping the team drive adoption and usage.

2. I look to find people that are curious, have something to prove, are always learning and are a personality we think will complement the team.

They need to be able to teach us something.

They need to be a person we want to be around.

Simple, not easy.

3. Long answer but some insights here in this post.

Once a company gathers in a user with the aim of creating a long term, valuable relationship — how will this shape how and where product teams allocate resource? Should the product team double down on further delighting and enabling this customer (e.g. retention) and less on product to get people into the funnel (activation)? Or is retention less of a product problem and more of a community manager role.

I strongly believe retention is a product/growth problem. It’s not a community manager problem. We all get why this is true, but most businesses do nothing to maximize retention. Acquisition is great but like drinking a Red Bull it only gets you so far.

The way I implement this is to measure product teams on lots of things but most importantly usage over time by cohort. What I want to see is that we are driving lasting changes with new features and changes. I also measure each team on feature adoption by cohort, customer NPS (again by cohort), etc, etc.

I think businesses are getting good at capturing lots of user data but they suck at being able to act based on that data. We aim to change that at Driftt. Analytics without the ability to act/test/respond is useless. That’s where most businesses are stuck today. We’ve made huge leaps in gathering the data, and in some cases making it somewhat accessible but not in acting upon the data.

Even in the most advanced business, I see the same problems: siloed data, no centralized view of the customer, no ability to understand all the interactions and events that are happening with a customer, an account, a company and no playbooks for how to act upon that data easily.

I think that in here lays the opportunity for the next generation of companies to be built. We will get good at this over time and the result will be more cross-sell opps. and longer lasting customer relationships.

You’ve always seemed to have a good sense for timing, arriving at solutions just as the need reaches a fever pitch. How do you think about timing as it relates to new products and ventures? Is it all just innate?

You nailed it. So much of what we do comes down to timing. I think I have gotten better at timing over the years. Nothing worse than being “way-too-f’ing” early.

I attribute getting better at timing to one change: Focus on the CUSTOMER and not on MY IDEAS.

It’s really that simple. If we listen really closely to our customers they will tell us if our timing is right on, too late or too early.

You’re quite active on Twitter — are there any profiles that you feel are must-follows for growth entrepreneurs?

Hiten Shah: @hnshah
GrowthHackers.com @GrowthHackers
Marc Andreesen: @pmarca
Driftt: @driftthq
Chris Dixon: @cdixon
Dharmesh Shah: @dharmesh
Mike Volpe: @mvolpe
Aaron Levie: @Levie
Tren Griffin: trengriffin
Shane Parrish: farnamstreet
Nassim Taleb: nntaleb

Can you talk about customer development and the parts of building a company that a lot of people don’t ever see? Between HubSpot and Driftt, how many ideas did you invalidate? What were they? Why didn’t they work out? What was the process?

Too many ideas to list.

Here’s the simple way I think about all things customer/product dev related:

Your assumption should be that every idea, every release, every attempt is WRONG. The default state is that you are wrong. Your job is to validate how wrong your attempt was and how to fix it. Were you 10% wrong? 100% wrong? It’s usually somewhere in between those two numbers. Get as many “at bats” as possible and calibrate.

Every creative process follows this model, but we get it wrong so often when it comes to building a Product, writing Software or starting a Company.

When you write do you expect your first draft to be the one you publish?

If you were a woodworker and you built a table for the first time would you expect the first version to be your award winner?

Would a painter expect their first attempt to be a masterpiece?

Of course not. For some reason we think building a company/product/feature to be exempt from this fundamental law.

If your children had just graduated from college and ask you for advice about their personal and professional life, what frameworks or principles you would pass along to them?

Love this question.

I have two kids, 10 and 4 years old, so I think about this a lot.

First, I don’t think everyone should go to college. I talk about that with my family now. I want my kids to find something they are passionate at and can have a chance at being *great* at.

If they did decide to go to college I would support that decision but not push them towards that choice. I want that choice to be theirs to make.

Ok so now imagine they have graduated from college. Here’s what I would share with them:

1. Be Patient. There is no rush. Take time exploring, traveling, reading and learning each day. The road ahead is long, learn to be a great thinker, to be a great friend, to be a great colleague and how to be productive.

2. Experiment. As you are thinking about the future constantly experiment. Try things, measure the results and avoid cognitive biases in analyzing your outcomes. Learn to be a learning machine. Never stop trying to improve yourself.

3. No right answers. Unlike your time in school there are no right answers in life. Only decisions and outcomes. Don’t look for secrets, tricks or shortcuts. The best lessons are right in front of you. Just pick paths that feel right in your gut. Learn to trust your gut, it’s faster than our analytical mind.

David is launching a podcast in January 2016 called Seeking Wisdom. Signup here and be the first to know when it launches. You’ll get nuggets like this once a week.

Customer Driven

Lessons from the trenches of building a customer-driven company.


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Sharing the lessons we’re learning building Boston’s next pillar company.

Customer Driven

Lessons from the trenches of building a customer-driven company.

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