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I'm the founder of Clearbit and Reflect. AMA.

Hello everyone!

I'm the founder of https://clearbit.com, a ~100 person profitable company in the data space, and of https://reflect.app, a note-taking lifestyle business.

Six months ago I replaced myself as CEO of Clearbit and am now focussed full time on Reflect (and Kiteboarding).

I love writing English and TypeScript. Some of my recent projects include:

Happy to answer any questions, but bear in mind I can be more candid about questions related to Reflect (as I only serve at a board capacity at Clearbit).

  1. 2

    Hi Alex! Thanks for doing this AMA. I'm a big fan of The Great CEO Within and The Manager's Handbook.

    I'm curious what you think your highest-leverage habits are. Really broadly speaking, like anything related to nutrition, exercise, meditation, relationships, communication, routines, etc.

    1. 3

      Great question! Habits maketh man. Unfortunately I figured this out rather late, in my 30s.

      • Eating: Currently I am fasting the whole day until dinner. This is an experiment, but seems to be working.
      • Exercise: Kitesurf when I can, otherwise workout video (Peloton has some great ones).
      • Meditation: I try and meditate every day
      • Relationships: The best book I've found on this is Hold me Tight.
      • Communication: Most of what I know is in the two books listed

      I generally try and work all morning, and kitesurf all afternoon. Meetings are kept at a minimum.

  2. 2

    @maccaw Much respect for what you've built with Clearbit and cool to see what you're up to now with Reflect. I need to check that out.

    Although for me personally, it's your work with Matt and Misha on The Great CEO Within that has been the most impactful. It helped firm up my decision to start a coaching practice. So thank you for helping bring that book to life.

    I didn't have a question initially, I was stopping by to say thanks. But, now that we're here...

    What activities, realisations or new ways of doing things will you keep from this past year? (and is there anything that has been specifically prompted by your new roles)

    PS. ..." the majority of the world's languages don't make a distinction between the colors green and blue." — a gem from when I went down a rabbit hole on your blog some time back. It stuck with me as it really echos the whole point on how much we've invented (er...made up).

    1. 4

      Wow - thank you. I can't take much credit for The Great CEO Within. Matt taught me practically everything I know.

      What activities, realisations or new ways of doing things will you keep from this past year?

      Good question. Let me share a little nugget of wisdom I got from a conversation with Naval.

      We try and avoid boredom, but actually boredom is a fundamental part of creativity. It's only when the mind wanders do we have space to come up truly creative solutions.

      The issue with today's executive's back-to-back schedules is that there is no downtime, and therefore no room for boredom. Ergo, you can't be creative if you have a full calendar.

      So I try not to keep a calendar. I keep my company's communication completely asynchronous and I make space for boredom.

      1. 2

        Getting it from Google Doc to the book was 🎯

        Love that bit of wisdom. Reminds me a little of Paul G's essay on maker vs manager schedule—albeit the framing here from Naval is different, but similar sentiments. Thanks for sharing.

        On that note, you might enjoy this:

        https://moretothat.com/fluid-thought/

  3. 1

    Have you tried wing foiling?

  4. 1

    Hi Alex,

    Thanks for this AMA and congrats on your success.

    What resources did you find most useful for building a DaaS business? Auren Hoffman provides great information but did you find anything else?

  5. 1

    Hey there! Long time consumer of the https://themanagershandbook.com/, it helped me transition from an IC to a manager.

    If you have to name the 3 biggest lessons from your time as a manager/CEO, what would you nominate?

    1. 1

      Thank you! In terms of management, I'm listed the most common mistakes/lessons here: https://themanagershandbook.com/coaching-and-feedback/common-management-mistakes

      In terms of being a CEO - one of the biggest learnings, and I've only figured this out recently, is that it's important to choose a customer base that you really respect and want to hang out with. The more you like your customers, the more customer research you'll do, and the better your product will be.

  6. 1

    Hi Alex, thanks for jumping on. Two questions for you

    1. how did you get your first 1000 customers?
    2. What are your favorite kite surf spots?

    I'm actually learning kite surfing right now as well. About 8 hours of lessons in at this point and still deciding whether or not I should continue. I'd like to be able to kite near my place in Seattle but because it's wind dependent my fear is I'd only to be able to kite when I can travel to an ideal wind location.

    So far I've been to Squamish and Hood River.

    1. 1

      Thank you!

      1. For Clearbit, I got the first 10 customers just through hustling, going around my network and Twitter DMing people. The first 1000 customers just came to us inbound. We always had a huge pull from the market. Reflect seems to be on a similar course with 6k people on the beta list.

      2. I've kitesurfed in NZ, Mexico and Puerto Rico. The latter is my favorite. Warm water and consistent wind is key for me. Kiting is very difficult at first, and then very easy shortly after. After 10 days of going every day you'll be up and transitioning.

  7. 1

    Hey Alex! Huge fan of your essays!

    On the Manager's Handbook you mention the Zone of Genius...any more tactics on discovering one's zone of genius?

    Self-awareness can tough, but just wondering if you could share how you discovered yours and seen others discover theirs. Thanks a lot for doing this!

    1. 2

      This is a difficult one. I was fortunate. I knew from the age of 13 that wanted to be an engineer. Others spend a lifetime searching. But don't give up. It's worth it when you find it.

      When picking a career, people often end up going with what they're good at NOT what gives them energy. This is a massive trap, and why you see so many disillusioned lawyers.

      Some ideas:

      • What activity does you achieve flow state in?
      • Is there anything you love so much that the hours pass by without you noticing?
      • Ask friends / colleagues. What am I really good at but also gives me energy?
      1. 1

        Thanks a lot for the time, Alex, really appreciate it! I'm a very happy user of Clearbit at work, and cant wait to use Reflect in my day to day. Thanks for inspiring us all to build and become better professionals!

  8. 1

    Hey Alex, I'm a big fan of clearbit and data businesses in general. So many of these businesses are geared towards sales/marketing with individual contact data and data about businesses.

    Do you see problems in other verticals that could be solved with 3rd party data?
    What do you think the future will look like for data companies?

  9. 1

    Hey Alex,

    I’m curious how you were able to differentiate and win a ton of market share in the enrichment space, especially earlier on. What was Clearbit’s advantage over the other enrichment giants? What was the selling point to early investors? And how did you win over customers from the other big players?

    Thanks!

    1. 1
      • Good data (coverage/quality)
      • Nice design
      • APIs
      • A great team leads to great customer interactions.
  10. 1

    Hi Alex, I just came to know your story via the essay - Traveling, Writing and Programming (2011). Quite impressive by the lifestyle described. And it seems
    that later you mainly work in California. As remote-working is quite heated today,
    would you leverage it to your company, gradually as a norm?

    After all, "The peculiar thing about programmers is that they're the one profession that can easily work remotely and travel, and yet they're the one profession that doesn't."

    1. 1

      It depends what you're optimizing for. For lifestyle, having a totally async business is ideal. To grow and self actualize, nothing beats being in the presence of an incredible team.

      Personally I would never go back to an office. My life is too good now. But I've had that incredible bonding office experience. I worry about young people getting into the industry today. Doing an internship over Zoom has got to suck.

  11. 1

    I read somewhere few years back that you leveraged some incumbent database for building the data store of Clearbit. Can you open on what it was? And how you could get a resell licence?

    1. 1

      Sorry, not sure what you're referring to here. We barely resell any data at Clearbit, and we've only started doing so in the last couple of years.

      1. 1

        The email id, company data that you originally had. Was that all scrapped from Internet? or clearbit was a reseller of some large database?

        I read some article that Clearbit had a licence to resell data from D&B (I think) and Clearbit was successful because of the API infrastructure and ease of use over D&B legacy infrastructure.

        But, I can be wrong as well. If this is true, I was curious how you made it happen :)

  12. 1

    What made you decide to go replace yourself as the CEO of Clearbit? Was it just that it was taking too much time away from Reflect? And how how hard was it give up day to day control of Clearbit to the new CEO?

    1. 1

      I wrote a bit about why I left as CEO of Clearbit here [1]. Suffice to say, I wasn't the right person for the job. My heart lies in the zero to one - creating something from nothing. Not managing a large company.

      A framework I've used often for making these kind of decisions is the Zone of Genius [2], which basically guides you towards doing things that you're great at that ALSO give you energy.

      I left Clearbit without knowing what was next. I only knew that what I do, the zero to one, is fairly rare. I should just focus on that and let professionals do what they do best: scaling.

      Leaving your own company is extremely difficult. Living something everyday for five years means it becomes more than just a business. It becomes part of you, part of your identity. It took me years of therapy even to get to the point that was a possibility in my mind.

      [1] - https://clearbit.com/blog/company-update/
      [2] - https://blog.alexmaccaw.com/zone-of-genius/

  13. 1

    Hi Alex! I have a few questions, feel free to pick and choose :)

    1. You describe Reflect as a lifestyle business. What were are some things you'll do differently based on that distinction compared to Clearbit?
    2. What do you think is your "unfair advantage" when it comes to building Reflect?

    Happy surfing! 🤙

    1. 2
      1. Reflect is pretty much the exact opposite of Clearbit. It's self-service (vs sales), prosumer (vs B2B), and a UI heavy products (vs mostly data wrangling). It's very much intentionally so. After Clearbit I was keen to get back to my roots building lifestyles bizs.

      The biggest difference with Clearbit is that we will intentionally not grow headcount and try to keep things as lean as possible. This allows us to bootstrap the business and not constantly trying to grow as fast as possible.

      1. Two unfair advantages: speed and patience. The team at Reflect moves at lightning speed. This is because we're four engineers using a modern stack. Patience - at this point I'm not motivated by money or growth. I just want to build the best note-taking app ever created. No matter how long that takes.
  14. 1

    Hi Alex! Literally just spoke over email on the weekend – small world eh 😂

    1. Reflect – I saw you mentioned here it's specifically a "lifestyle" business. That's refreshing to hear. Why are you choosing this path – are you tired / bored of building companies and more excited to build product again? It sounds like you are living the dream!
    2. Stepping down as CEO from Clearbit – was it a hard decision? Was it an easy decision? Any tips you can share for others here? I think many people struggle to disconnect from the businesses they started.
    3. Just wanted to say thank you for writing the Manager's Handbook – it's proven incredibly valuable for me in the past, and is a brilliant resource I share with others frequently.
    1. 2

      After stepping down as CEO so publically I had a lot of other CEOs reach out to me curious about the process. I think it's important we talk more about this. Many founder CEOs are under the (false) impression that they have to hit that IPO bell personally in order to be loved/successful. The reality is, nobody cares if it's you, or some other CEO you hired. Just go live your life and be happy. Ultimately, nothing matters in the big scheme of things! [1]

      [1] - https://blog.alexmaccaw.com/nothing-matters/

      Certainly a small world. Thank you for the kind words. I think management has a huge amount of leverage, so I hope my small contribution goes towards that.

      1. 1

        Gosh that’s a beautifully written piece. Thanks for making my day, Alex!

  15. 1

    Hey Alex! I follow you since CoffeeScript Era – good old times!

    I'm curious how a developer like you, that wrote a technical book, shipped some frameworks there, and started a successful company, decided to leave his own company to "back to origins"

    During your time running Clearbit, what did you enjoy more and you think you could never have achieved as a solo developer?

    Also, What do you really miss but you couldn't do because you are running a company?

    Thanks for your time, hope to see you on the water someday (I do windsurfing!)

    1. 2

      One of the few sustainable addictions is creation. I believe that if you spend your life seeking and feeling that creative energy, it'll be well spent..

      Now, that doesn't mean that everyone has to code. People feel their creative energy in all sorts of different ways (thank goodness!). But for me, it means coding. Every-day I need to code something.

      For many years I forgot that. I had to give up engineering in order to be a 'good CEO'. Once you have > 30 employees your job becomes delegation and team-building. But, while painful, I don't have any regrets that I did the 'big company thing' once. Self-growth, almost by definition, involves a degree of discomfort. Founding Clearbit made me the person I am today.

      I wrote a bit about the pros/cons of lifestyle business here [1], but the major con is they can be a bit lonely. Fortunately, these days, I get my sense of community from outside my work.

      [1] https://blog.alexmaccaw.com/lifestyle-vs-venture/

      1. 1

        This is great insight. Over the last year, I have felt the same ----- developer -> CEO/founder -----> back to developer. I wrote about this feeling on my blog during the lockdown - https://sahilparikh.dev/posts/2020/in-code/

        Thank you for this amazing thread. Need to read all your blog posts as well :)

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