Dashbot’s Dennis Yang: Why Conversational Data Captured His Attention — And Why You Should Care Too

Kelli Kissack
Chatbots Magazine
Published in
6 min readMay 18, 2017

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(This interview is part of the “7Q Series,” a weekly interview series brought to you by Chatbots Magazine.)

Dennis Yang has worn many hats during his career in tech. He’s currently the co-founder and Chief Product Officer at Dashbot, but he’s been involved in more than five companies (in various roles) since moving to San Francisco in 1997. He deeply understands startups, breaking things, fixing things, and the path from idea to profitable product.

1. How did you become interested in bots? Please share the journey that brought you to your current role with Dashbot.

Dashbot is the fifth startup that I’ve been involved with. I was the ninth employee at mySimon (a comparison shopping site) back in the late ‘90s, and transitioned from engineering to product management after our acquisition by CNET. Then, I left to cofound Techdirt, a technology blog that is still doing well today. I was then the ninth employee (again!) at Infochimps, a data marketplace that was later sold to CSC. Then, I cofounded Bureau of Trade, a vintage marketplace that we sold to eBay back in 2013.

I was trying to figure out what to do next when a mutual friend introduced me to Jesse, one of our other cofounders of Dashbot. Over the course of a year, Jesse and I built, launched and scrapped five different products. We were pretty much about to give up when one of my friends, Mike, exclaimed to me that the Amazon Alexa was the most amazing thing that he’d used in a long time, and he convinced me to get one. Once I had the Alexa in my house, I realized that perhaps Mike was right, and conversation as an interface was really interesting.

“Once I had the Alexa in my house, I realized that perhaps Mike was right, and conversation as an interface was really interesting.”

So, we started writing bots. When we launched our bot, GameMonk, a game for Slack— we quickly realized that analytics was a huge need for bots. Coincidentally, that very same day, Jesse met up with one of his old friends from his college days at MIT, Arte (who had previously founded a mobile analytics startup). Arte had also come to the same realization that bots needed good analytics. We joined forces, and a month later, we launched Dashbot. It’s been an amazing ride ever since.

2. Why has conversational data captured your time and attention?

I’ve been lucky to be working in the web since 1995, and back then we had to build a lot of our analytics from scratch to understand what was happening on our websites. When I started working with conversational data, I was impressed with how rich it is compared to the event-based paradigm of web and mobile. Looking at an event stream, you are trying to guess what your user is trying to do. With conversation, you can read and understand the words your users are sending. Conversational data is so much more actionable.

Taking a step back, I’m really excited to help our customers create and develop these conversational interfaces. I was involved in the previous two evolutions of human computer interaction: web and mobile. With each of these developments, these interfaces become more accessible and important to more of the world’s population, and conversation is no different. Conversation is one of the first ways that humans learn to communicate with one another, so to be able to communicate with computers in that same way is incredible.

“Conversational data is so much more actionable.”

3. What’s the #1 misconception people have about bots + data?

There seems to be a “debate” between buttons or natural language, i.e. which interface is best? I don’t think it’s an “either/or” situation because in real life, we seamlessly transition between a “button” interface (ordering from a restaurant menu) to a “conversational” interface (“Please put my salad dressing on the side”), and I hope that bot UI designers allow their users to do the same. My advice is to use buttons where they make sense and allow for natural language where it makes the most sense.

“My advice is to use buttons where they make sense and allow for natural language where it makes the most sense.”

4. How have things changed since 1997? Is there something you wish the new people would learn not the hard way, as you might have?

When I first moved to San Francisco in 1997, everyone complained about how difficult it was to find an affordable apartment — I stayed at a friend’s apartment in the tenderloin for three months until I finally found my own place. That, apparently, has not changed. One thing that I have noticed that has changed is the overall attitude towards competition. “Back in the day” there felt like more of an environment of community and cooperation. Sure, competition has always been around, but it was more common to hear “a rising tide lifts all boats” rather than “crush all competitors at any cost.”

As for advice for new people, here’s a piece of advice I got from one of the founders I worked with a few years ago: “Don’t solve problems you wish you had, solve problems you actually have.” It’s so easy to get mired in the “but what if” scenarios that you easily lose sight of the problems right in front of you.

“Don’t solve problems you wish you had, solve problems you actually have.”

5. Which bots do you use on a daily basis?

I use my Google Home and Amazon Echo every single day. Amazon’s morning update is a part of my daily routine, and I’ve been using Google more and more for random queries. I’m a big fan of game bots, so naturally I play our own GameMonk regularly with our team here at Dashbot. I was a huge fan of Streak Trivia until they shut it down last year. I’ve been enjoying the other games the Streak creators have made since then, like DoodleChat.

“Bots will teach us about ourselves because, in building them, we will learn more about what it really means to be human.”

As an obsessive user of Swarm (FourSquare), I like MarsBot a lot. Whenever I’m looking for something to watch on Netflix, AndChill has been a great help. One last “bot” I use almost every day is “Are You Watching This?” RUWT only delivers you alerts when an epic sports event is happening (a no-hitter, crazy overtime situation, etc). I find it to be one of the best examples of how timely, relevant notifications can surprise and delight you on a regular basis.

6. Outside of Dashbot, how do you like to spend your time?

During the winter, I’m a volunteer ski patroller up at Homewood in Lake Tahoe, and the rest of the year, I’m an avid cyclist. Lately, I’ve been nesting a lot more, making a home with my wife, Tricia and our dog, Bear, in preparation for our first child, who is due any day now. My wife is also a startup founder, so we are going to have our hands quite full!

7. Complete this sentence. “Bots will _______________ because _________________.”

Bots will teach us about ourselves because, in building them, we will learn more about what it really means to be human.

Follow Dennis on Twitter and Facebook. Click the ❤ below to recommend Dennis’s 7Q interview to other Medium readers exploring bots, analytics, and conversational interfaces.

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🖌Writer serving equine+western media 📷Photographer for the equine-obsessed 🦄Rodeo traveler + cowboy's sweetheart 👩🏻Blogs at KelliOutWest.com