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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.

Ask him anything about startups, product, entrepreneurship, building teams and selling to businesses.  

You can follow David on Twitter: @dcancel and subscribe to his blog at http://davidcancel.com/. David's also launching a new content series focused on startup learnings in 2016. Signup here to be the first to know when it launches: http://davidcancel.com/newsletter.

He will be on live on Thursday, Dec 17 from 930 AM PT for one and a half hours, during which he will answer as many questions as possible.

  • DC

    David Cancel

    about 4 years ago #

    FYI this is the theme song from this AMA:

    https://www.youtube.com/watch?v=UfQOawFwx6w (Kanye - ALL DAY)


  • TS

    Terence Strong

    about 4 years ago #

    Hi David:

    Thanks for doing this!

    I noticed that 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?


    • DC

      David Cancel

      about 4 years ago #

      Hey Terence!

      Thanks for the question.

      First, I'm lucky and I make a point of being grateful each morning for what I have, most importantly my family. :man:‍:woman:‍:boy:‍:boy:

      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.

  • DC

    David Cancel

    about 4 years ago #

    Hey all! Super excited to be here. I even wore my favorite Jordans for the occasion.

    Thanks for the questions!

  • DG

    Dave Gerhardt

    about 4 years ago #

    You read a lot. Pick 3 books that every entrepreneur should read in 2016 if they haven't already.

    • DC

      David Cancel

      about 4 years ago #

      You know the way to my heart.

      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.

      3 Share
  • ES

    Edward Stephens

    about 4 years ago #

    Hi David,

    Thanks for agreeing to do this - really looking forward to hearing your insight!

    A question I had on the back of reading your Linkedin article on Relationship Marketing.

    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.

    Finally, with all the knowledge we can accumulate on users these days, will this naturally lend itself to more cross sell opportunities with other companies as we build out richer user profiles?

    • DC

      David Cancel

      about 4 years ago #

      Hi Edward,

      Thanks for reading my Relationship Marketing post!

      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.

  • MK

    Meghan Keaney

    about 4 years ago #

    Hey DC - Hope you're having a good AMA.

    I would imagine that for any new company, two of the main things to get right are
    1. The problem you're trying to solve, and
    2. The timing

    Go after an emerging problem too early and you risk building a solution before the audience knows they need it. Go after an emerging problem too late and, you're always playing catch-up.

    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?

    • DC

      David Cancel

      about 4 years ago #

      Hey MKA!

      MKA is my homegirl in case you didn't know. Now you do. :information_desk_person:

      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-fucking" 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.

      Thanks MKA!

      2 Share
  • LS

    Logan Stoneman

    about 4 years ago #

    Hey David! You're quite active on Twitter - are there any profiles that you feel are must-follows for growth entrepreneurs?

    P.S. If you have any random profiles you feel are must-follows as well, shoot them our way!

    Thanks for doing this, amidst your crazy schedule, it's great to hear your thoughts on the community's questions.

    • DC

      David Cancel

      about 4 years ago #

      Hola Logan!

      This is fun. Loving the AMA format!

      Must follows:

      dcancel <- of course!

      4 Share
  • BC

    Bob Cavezza

    about 4 years ago #

    Hi David,

    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?

    • DC

      David Cancel

      about 4 years ago #

      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.

  • BT

    Brad Thibeau

    about 4 years ago #

    What is the most important thing you do each day?

    • DC

      David Cancel

      about 4 years ago #

      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.

      8 Share
  • HQ

    Hila Qu

    about 4 years ago #

    Hi David,

    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?

    • DC

      David Cancel

      about 4 years ago #

      :hearts:️ 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.

      • AA

        Anuj Adhiya

        about 4 years ago #

        That moment when you wish you could upvote more than once

      • HQ

        Hila Qu

        about 4 years ago #

        I absolutely love these answers. I wish my parents have shared that with me, but now I got a chance to share that with my kids:)

  • TT

    Tim Thyne

    about 4 years ago #

    Thanks for doing this! You and the team have been doing a ton of research on product marketing/customer success. I'd love to hear your thoughts on what you think the future of these teams will be from an organizational standpoint. The goals of the two teams often overlap. Have you seen a framework for organizing them that is most successful?

    • DC

      David Cancel

      about 4 years ago #

      Yo Tim!

      Hope all is rocking at HelpScout!

      In the ideal world I think those teams would start to merge but I don't see that happening anytime soon. Why I do see happening is the lines between Product Marketing / Growth / Product Management continuing to blur. I think we'll see those roles come together into a single function before we see Success and PMMs coming together.


  • AS

    Abrar Shahriar

    about 4 years ago #

    Hi David,

    thanks for doing this.

    Q.1: As a young enthusiastic of SEO, What is the basic guideline should I follow?

    Q.2: If I grow my career as a content marketer and SEO expert, what will be my daily task?

    Q.3: I need a suggestion that which book or article I should mostly follow?

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