Proust Goes Tech With Mark Webster, CEO and Founder of Sayspring

Mark Webster, founder and CEO of Sayspring, helps designers create voice applications without code for Amazon Alexa, Google Home, and other platforms. He has founded three startups to date, one of which was acquired by Groupon in 2013.

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In the meantime, you can find Mark on Twitter—assuming he’s not scheming of ways to cut down on his newfound social media habit.

Now let’s find out what else our gamut of tech-inspired Proust questions can tell us about Mark.

What would you otherwise be doing right now?

If I wasn’t working on this specific business, I think I would still be starting something. I’ve done another startup before [Sayspring]. There’s a piece of me that could definitely be in politics. I’m a total politics junkie.

Your main fault?

I can definitely be abrasive. It’s a little part of my Long Island, NY upbringing. You can say really direct things to me, and I’m fine with that, and I encourage that. But it doesn’t really always work the other way.

I don’t have an expectation that you’ll send a card on my birthday or remember my birthday, so I can be bad about working into other people’s expectations. The golden rule only works as far as your own framework of expectations for other people.

The quality you most desire in a tweet?

One of the things I love about Twitter, and what I love about Reddit or the Internet in general, is that it has become this forum of appreciating other people’s humor. The chuckle out of Twitter is one of the main reasons why i use it

Your idea of misery?

My misery is sort of feeling like I’m being forced to serve somebody else. I have no problem with authority. I’m happy to have someone else lead. But I hate feeling like I’m under somebody’s thumb.

What do you appreciate the most in your friends?

Easygoingness… the next time you see them you feel like you are picking up from where you left off.

Your chief characteristic?

Self-sufficient and hard-working. I want people to enjoy having me around. I’m always more than happy to work hard to make somebody else’s life better.

What skill do you wish you possessed?

Focus better. Probably related to my Twitter fascination. I’m kind of like a jack of all trades. I’m [also] totally uncoordinated. I can’t play an instrument. I can’t roller skate. I’m terrible at sports.

What defines success?

Success is being in complete control, in a sense that you are not beholden to other people. I could live my current life in perpetuity and I can be totally happy with that. Do what you want when you want it. Finding work you enjoy doing. Being able to have that pacing.

When is confidence lost?

When something happens that seems contrary to your worldview. A loss of self-awareness.

What virtues do others have that you don’t?

It feels like you could argue I have questionable loyalty. Not that I would stab anyone in the back. But I think part of loyalty is understanding somebody else’s view and expectations or their needs and wants and how to fulfill those things.

What’s the biggest problem tech is failing to solve?

I’m disheartened with the sexual harassment stuff that’s come up in the culture of Silicon Valley and tech in general.  There’s lack of self-reflection and empathy and thinking not of our own problems. One of the big things that’s holding back tech is the tech community and the culture around it. It just makes the community so inwardly focused that I think we are sort of missing the bigger pictures and getting disconnected from other people’s problems. Tech is not the problem; it’s the people practicing it.

Editorial note: Answers have been edited for brevity and clarity.

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