AMA: Chris Kalani — Ex-Facebook Designer / CEO of Wake

over 1 year ago from , CEO at Wake

Chris Kalani

Hey everyone! I’m Chris Kalani, a former Facebook product designer and recent co-founder/CEO of Wake.

I knew I wanted to make stuff on the internet since I was 14 and I pretty much started my career while I was still in high school. I decided to skip college all together and over the course of the next 6 years, worked for a couple small companies, a VC funded startup and a large agency or two.

I mostly did work for Nike, Microsoft, Visa and Adobe. But also did a bunch of personal projects on the side to stay sane.

In 2011 I joined the product design team at Facebook where I worked on Messenger, Growth & Engagement, and Graph Search. I loved it, but ultimately ended up leaving after I felt the team had gotten too big for me to be impactful. That experience changed my life and I learned a lot.

Last year I started a company called Wake with my friends Tobias and Johan who run an agency in Norway called Bakken & Bæck. I’ve spent nearly 8 months off and on living in Oslo, and what started out as a little project quickly turned into an actual company. Read the origin story.

I’m doing this AMA to answer any questions you might have about design, Facebook, Wake, starting a company or building a career without any formal training or schooling.

If I’m able to inspire just one person to go out and make something cool, then this will be worth it. Let’s go!

52 comments

  • Joel CalifaJoel Califa, over 1 year ago

    Does everyone who leaves Facebook get a goodbye letter from Adweek? :P

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  • Lanya OlmstedLanya Olmsted, over 1 year ago

    When you say that you left the FB team because it had gotten too big for you -- can you elaborate on that?

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    • Chris KalaniChris Kalani, over 1 year ago (edited over 1 year ago )

      When I joined the company there were maybe 18 product designers not counting the 2 design managers. We all sat together and operated as a single team working on multiple products at once. As we grew the team was broken up into product specific teams. We moved campuses and began sitting in different buildings.

      Design became more integrated into each product vertical, which was the right call and the only way we were to scale. But as time went on, more and more designers got thrown at projects once handled by a single person. So a product like Messenger which had 1 or 2 designers suddenly had 5+ designers. Same app, smaller slice of the pie, more cooks in the kitchen, more engineers, more PM's, more meetings == less doing what I wanted to be doing.

      By the time I left I think we had almost 100 designers. The company more than doubled and we went from 500M users to over 1 billion. Things just changed, as they were supposed to. I just wasn't able to handle the growth as well as others.

      Long story short, I LOVED (and still love) the company and everyone there. I owe so much to Facebook and I am glad I was there when I was. And I would still recommend working there, just not if you like small teams :P

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  • Jason AmorJason Amor, over 1 year ago

    Would you recommend Ham Horn to others? What problems does it solve for you?

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    • Chris Kalani, over 1 year ago

      Ham Horn really just kicks things up a notch. It gets the people going. Other apps pale in comparison. And I'm not just talking air horn apps. I mean all apps.

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  • Joshua JenkinsJoshua Jenkins, over 1 year ago

    I think Wake is great because it has hooks into my workflow. I probably wouldn't use it if I couldn't just claw a keyboard shortcut from Sketch which then pushes to Slack. I dig the interfacelessness of the whole thing. Also a big fan of the recent desktop notifications update so I can see when someone comments without looking at another app.

    Any thoughts on how you think about these kinds of workflow integrations? Can you do backflips or anything like that?

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    • Chris Kalani, over 1 year ago

      Removing as much friction and thought that goes into sharing stuff is key. We don't want people thinking too much about how to organize things or who they're sharing with. Sharing straight from your design creation tool is a start. Eventually sharing straight from your brain / exporting your imagination is where we'd like to end up.

      I can do a kick flip, a side flip and a backwards rotating front flip. And a sideways front spinning flip flap.

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  • andrew mundy, over 1 year ago

    Hey there Chris! I've really enjoyed following you from all the way back in yay!everydays. Super excited for you and wake and where it'll take you. I guess if you were to squeeze some question juice out of me I'd have to ask you a development thing. Swift. Any experience? I'm extremely development vanilla and finally pushing myself to learn a coding language. Any advice?

    Also, can you still crazy cool backflip?

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    • Chris Kalani, over 1 year ago (edited over 1 year ago )

      Hey thanks! Honestly my time these days isn't best spent coding, so I haven't had a chance to dig into it unfortunately.

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  • Crampa ...Crampa ..., over 1 year ago

    Have you considered dating Pasquale, or is he just not your type?

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  • Koen Bok, over 1 year ago

    For Wake, what kind of teams do you see adopt it successfully, and what are some great arguments that I can use for my team to start using it?

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    • Chris Kalani, over 1 year ago

      We typically see bigger teams with multiple designers or multiple projects happening simultaneously. Tiny teams already know what's going on with everyone so they don't have a big communication problem that needs to be fixed yet.

      That said, we have a lot of 1 designer companies who use Wake to document their own process and in doing so the rest of the their team still finds a lot of value in seeing the progression and thought process.

      Teams who began conducting all their critiques through Wake, pulling it up on a screen in a meeting room and going through what's been shared has helped get everyone on the same page.

      Also just leading by example and sharing your own work will usually get others to follow. If Wake becomes the place where everyone is able to see new fresh work, then your team will continue coming back. Does that help?

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  • Bryn JacksonBryn Jackson, over 1 year ago

    What's your approach to building a focused product? I feel like we always hear people wishing that all their tools were combined into some kind of Swiss Army Franken-tool.

    How do you keep Wake focused when people (myself included) are always asking for more features?

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    • Chris Kalani, over 1 year ago

      It's best to separate your goals and values from functionality and execution. I'll give you an example:

      People have requested we add the concept of projects or sub-teams. And those requests seem reasonable and useful at first glance. But, we want Wake be the fastest way to share with your team and we want it to provide transparency. Those features, if not done right could impose friction when sharing and silo off groups of people. Both going against our core values.

      So as long as we have these overarching values, we can design everything with those in mind instead of just building features aimlessly.

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  • Pete LadaPete Lada, over 1 year ago

    Can anyone just start their own AMA now? Honestly curious how the process is supposed to work. Also I feel like a ton of questions were left unanswered? Haha.

    Interesting story though; good luck with Wake!

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    • Chris Kalani, over 1 year ago (edited over 1 year ago )

      I'm not sure... I recently launched my company which is specifically for designers. And I'm good friends with Andrew, the new DN overlord and we discussed me doing an AMA, so I did it.

      We posted this last night before I went to bed, in hopes to promote and answer everything in the morning and throughout today. I'm at the office now, so I will begin answering everything!

      Also, it takes a while to come up with a thoughtful response! I don't want to look like a total IDIOT here.

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    • Maxwell LindMaxwell Lind, over 1 year ago

      We asked Chris to join us and share his thoughts on everything from design to Wake to starting a company to intro videos! ;)

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  • Tyler StickaTyler Sticka, over 1 year ago

    How do you decide which compromises benefit a design and which damage its vision or integrity? Did you find that your approach to compromise changed significantly as you moved from smaller agencies to Facebook to your own company?

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  • Mitch De CastroMitch De Castro, over 1 year ago

    What do you think design students, who are in college now, should be learning if they want to prepare themselves for a career in product design?

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    • Chris Kalani, over 1 year ago (edited over 1 year ago )

      The best possible thing you can do outside of whatever school is teaching you, is MAKE SHIT. Anything. Preferably your own self-initiated stuff. Modern companies with legitimate product design teams are looking for people who have the skill necessary to bring an idea to fruition. Your work will get you the interview, but your ability to think through problems, explain your thinking and your ability to get shit done is what will get you the job. Doing your own projects will prepare you for all those things.

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  • Josiah DJosiah D, over 1 year ago

    What do you eat while designing? Do you enjoy the fine taste of a Quiznos toasted submarine sandwich?

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  • Pasquale D'SilvaPasquale D'Silva, over 1 year ago

    Adam DeVine, is that you??????

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  • Caleb JessieCaleb Jessie, over 1 year ago

    When you worked for the smaller companies, how did you decide on the next steps you'd take to further your career?

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    • Chris Kalani, over 1 year ago

      I usually either got bored or hit a wall in terms of feeling challenged. I suppose those go hand in hand.

      Each job I left was for a different reason, but typically I had reached a point where I no longer felt I could muster up anymore or excitement or creativity. I think it's natural to outgrow your roles, especially early on. You should look at every gig as a stepping stone to learn and build relationships. I always went into it with that attitude. I always looked for something else that was harder and that I was afraid of. Your next gig should probably always dump you in over your head with people who are way smarter than you.

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  • Colm TuiteColm Tuite, over 1 year ago

    What are your plans for the future of Wake? What direction do you see it going? What problems do you see it solving?

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    • Chris Kalani, over 1 year ago

      Obviously I'm not going to give away everything. But at a high level, we want to fundamentally change the way people build products and make decisions. By providing a place where raw ideas have a chance to evolve and be refined.

      I won't consider Wake a success if all we do is provide tools that enable everyone to continue doing the same things they've been doing for the past 10 years. We have a lot of ideas around how this might be accomplished, but it will evolve over time as we continue to try new things. Our biggest challenge is changing people's mindsets, not building features that have been tried elsewhere.

      That's probably not the answer you're looking for but there are plenty of other places where I've discussed our vision.

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  • Ronan Flynn-CurranRonan Flynn-Curran, over 1 year ago

    What products or apps do you enjoy the most these days?

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  • Rohit MehtaRohit Mehta, over 1 year ago

    There are days when you feel blocked and can't think through well. What do you do to clear this mental block? What are your sources for inspiration?

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    • Chris Kalani, over 1 year ago

      Personally, I have a lot of ups and downs. There will be days where I can't seem to focus at all and I have yet to find a remedy aside from just leaving my desk or going for a walk. Flow tends to come in waves, at least for me. So when I'm really focused, I take advantage of that and work like crazy in hopes to offset the days when I'm useless.

      Involving more people or just talking about whatever you're working on will also help a ton to get your mind out of that unproductive cycle.

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  • Marco SousaMarco Sousa, over 1 year ago

    Wake is a beautiful product, congratulations. It is also a simple one. Have you considered design teams might not see enough value between paying for it vs having a slack channel where you upload WIP designs and comment? This is something I know my Head of Design is debating and I was wondering if you have a "convince your boss" answer or new features you think make the difference. Thank you.

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  • Jochen Huppert, over 1 year ago

    Sketch or Photoshop?

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  • M. AppelmanM. Appelman, over 1 year ago

    Please do elaborate a bit on the Wake introduction video. Did you guys come up with the script or did a marketing company help out?

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    • Chris Kalani, over 1 year ago

      In December last year I asked my buddy William Wilkinson (the main guy in the video) if he would be interested in coming out to Oslo with me to shoot and direct our launch video. I really liked the video he had done for his app Manual and he also happened to be leaving his role at MetaLab, so he had the time. He agreed and over the course of 2 weeks, he put together a script, a small team, and some sick equipment. We used whoever we could find to be in the video and shot it on a Saturday morning.

      The song at the end was originally put in as a joke by Will. He had heard it on the movie John Wick and thought it was funny. We all thought it was pretty hilarious and perfect for the video, so we reached out to the rapper T-BO DA FIRECRACKER and ended up licensing it for a very reasonable price.

      A few people here and there talk shit about how we swear in it too much, how everyone is white and how "unprofessional" it is. But most people love it, we had fun making it, it got people talking, and everyone is white because we were in NORWAY when we shot it! Overall I was happy with it and people need to chill out IMO :)

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      • Pierre de MillyPierre de Milly, over 1 year ago (edited over 1 year ago )

        I'm not sure the problem is the swearing, the whiteness and the professionalism. To me it's the ultra-fast and weird way the main guy speaks as well as his body language.

        Apart from that, I love that video :)

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        • Chris Kalani, over 1 year ago (edited over 1 year ago )

          I'm sure if Will could swap his head and body out with something else he would.

          William

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  • Gilbert BagaoisanGilbert Bagaoisan, over 1 year ago

    What makes a great product designer vs. mediocre one?

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    • Chris Kalani, over 1 year ago

      I think really great designers take a more holistic approach to their work; they spend more time understanding the problem, more time asking questions, more time thinking about the "why", maybe even questioning the "why", and more time thinking about how their solution fits into the bigger picture (business & financial goals, metrics, etc.). They'll usually see their work through to the end and follow up on it to ensure it meets their standards.

      Mediocre designers tend to spend way too much time wrapped up in the visual execution. They worry about how good something looks or what other designers may think of their work. They usually don't ask enough questions. They rarely think about the impact their work will have on people who interact with it. And they tend to make up excuses for why their work isn't as good as they want it to be.

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  • p k, over 1 year ago (edited over 1 year ago )

    What do you do to stay focused and disciplined? Any favorite technique, habit or story to share?

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    • Chris Kalani, over 1 year ago (edited over 1 year ago )

      I'm honestly not the most disciplined person... but I usually try to think of the 2-3 most important things that I can actually accomplish in a single day and focus on those things. I made a little app to help me with it.

      The idea is that the list can't be edited or arranged, and it wipes itself at the end of each day, so you always start fresh with the most important things for that day.

      Another trick I learned from my friend Jake is to set an arbitrary timer for like 20 or 30 minutes and then work until it goes off. I tend to be less distracted if I tell myself I just need to focus on something until that timer goes off.

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  • Matt ZanchelliMatt Zanchelli, over 1 year ago

    What is an area of design you have that you don't have much experience in but would like to learn more about?

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    • Chris Kalani, over 1 year ago

      There's a lot I don't know about or don't have much experience with. Print, illustration, and industrial design. I think it would be awesome to make a physical product of some kind some day. My mind always gravitates towards furniture or something I could actually use and see everyday.

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