Erik Chelstad on ‘grinding’ at startups and how avalanche safety led to launching Observa

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Observa CTO and co-founder Erik Chelstad hiking along the Ruth Mountain and Icy Peak Traverse in Washington’s North Cascades with Mount Shuksan in the background. (Photo courtesy of Erik Chelstad)

Erik Chelstad wants you to pay a little more attention to the person using the bathroom — not literally, but metaphorically.

Chelstad is co-founder and chief technology officer of Observa, a Seattle-based AI company that helps brands track the in-store marketing and placement of their goods.

The Observa team, which includes 18 employees, is seeking a place of greater security. The 4-year-old company has raised about $1.5 million and is talking to VC firms about more funding.

“I feel like we hear a lot about entrepreneurship, but like actors in the movies never using the restroom, we don’t hear much about the middle part between the ‘aha moment’ and the unicorn valuation,” Chelstad said. “It’s the grinding time, where every resource is scarce, every moment is precious, and every decision could potentially make or break the future of the company.”

Here’s how Observa works. When someone with the Observa app is in a store near the display of one of the company’s customers, they’re prompted to take photos of the shelves, submit them and then get paid. Observa uses AI to analyze the images and share the information with brands using their service. Nationwide, 85,000 people are submitting millions of photos daily.

Chelstad had a winding path to Observa. He grew up in Alaska, then studied computer and electrical engineering at Purdue University. A decade ago he returned to school to pick up an MBA at the University of Washington with hopes that it would improve his odds in entrepreneurship.

When it comes to startup flops, “in most cases it’s not the technology that is problematic,” he said, “it’s something about the business side that is the failure.”

Chelstad describes his varied career as working for big businesses like Honeywell, decades-old companies like Data I/O, “entertainment megaliths like Pearl Jam (he worked on the back end of the fan club website), startups no one has ever heard of, and well-funded companies hell-bent on an IPO like Isilon.”

Erik Chelstad astride the ravens at Mount Baker, which he describes as “sort of our Pacific Northwest version of ‘Game of Thrones.’” (Photo courtesy of Erik Chelstad)

But it’s his volunteer work that perhaps best prepared him for Observa. Chelstad, who is on the board of directors for the Northwest Avalanche Center (NWAC), helped build digital tools used in the Northwest and Colorado that allow backcountry skiers and snowmobilers to make and share observations about avalanche conditions while in the wilderness.

Chelstad joked that the poor internet connectivity and bad lighting found in some retail stores can create even “scarier” conditions than avalanche prone backcountry.

We caught up with Chelstad for this Working Geek, a regular GeekWire feature. Continue reading for his answers to our questionnaire.

Current location: Seattle’s Ballard neighborhood by the climbing gym and between the bars.

Computer types: All of ‘em, but mostly some flavor of Linux in a container.

Mobile devices: Samsung, and I have insurance because I move fast and own pants with small pockets.

Favorite apps, cloud services and software tools: Apps that let you tinker with the crazy device you carry are great. Tasker lets my phone do the right thing in all of the spaces of my life. Cloud services that let you keep ideas and tasks synced are great, so Todoist, Google Keep and Evernote. Without Evernote, I might be a lonely hoarder living in a house full of “interesting” articles. Spotify keeps me entertained during long drives or coding sessions.

Erik Chelstad, left, working with software engineer Alex Harrison at the sky’s-the-limit, warehouse-like offices of Observa in Seattle. (Observa Photo)

Describe your workspace. Why does it work for you? We’re in a funky warehouse in Ballard that we grabbed from our friends at Rad Power Bikes. It works because it feels like a startup with infinite possibilities instead of the infinite candy dispenser. Seriously, we could be building a time machine, a genetically engineered dinosaur or an amazing AI company to get brick-and-mortar up to speed with ecommerce. Tall ceilings and windows to the sky; it reminds you to drop limits and low expectations when you walk in.

Your best advice for managing everyday work and life? Love what you do and who you do it with. Sounds like a bad bumper sticker, but really, time is limited, so be excited about every day and fully engage in what you’re doing. That question about the interrupt-laden mobile devices? Keep them in your small pockets unless it’s really necessary.

Your preferred social network? How do you use it for business/work? Am I being an ironic Luddite if I say email? I like the thoughtfulness and control of one-to-one communication in a work scenario. I also use email to send out newsletters to those that are interested in what I, or my company, has to say.

Current number of unanswered emails in your inbox? Soooo many. I love clean running shoes and zero inboxes, but that tends to happen on an irregular cadence.

Erik Chelstad, CTO and co-founder of Observa. (Observa Photo)

Number of appointments/meetings on your calendar this week? Lots! As a working CTO (or Working Geek, if you will), I need to schedule large blocks of time to design and code. I also run marketing and customer success, so there are many things that need discussions and decisions. During fundraising, internal meetings become a luxury, and outside folks with deep pockets become the priority. What this means is that I block out the morning for architecture and coding, then have a series of 20 minute meetings most of the afternoon.

How do you run meetings? Agendas and input. Set the stage, but let the talent (I really hope everyone you invite to a meeting is amazing!) riff on what’s happening. Keep things short (20 minutes is great) and know what questions you need answered before you start. Some companies like Amazon will set aside time for people to get familiar with the material at the start of a meeting, but in a startup, you have a much more intimate connection with what’s happening, so you don’t have to start at zero like that.

Everyday work uniform? Well, it depends on the temps outside. As an early stage startup in a big funky warehouse, we need to self regulate with shorts in the summer and sweaters in the winter. Of course, the VC meetings require a bit of starch and collar, so there’s a button-up and slacks hanging on the back of the door.

How do you make time for family? Like meetings, you need to set this aside, probably putting on your schedule. I create and share online calendars with families and friends; they get used to it pretty quickly.

Best stress reliever? How do you unplug? Getting off of the grid! Love to climb mountains and ski or slog down them. It’s that whole “getting into the flow” thing, where you have to focus on everything that’s currently making up your physical environment. Is that hold safe? Is that snow bridge going to hold? Are those clouds bringing lightning? Seriously, that’s a different and beautiful type of stress. Added benefit: You really are disconnected, so your tech better be in good shape and good hands while you’re out there!

What are you listening to? Cleaning the house means podcasts like Reply All. Trying to sleep in a tent at the foot of a glacier means audiobooks about the History of British Finance. Focusing on tech and business means lyric-less music from Chopin to The Budos Band. Running brings out things like PJ Harvey and Killer Mike.

Observa’s Erik Chelstad at Vertfest, a benefit for the Northwest Avalanche Center (NWAC) held at Snoqualmie Pass that features snow education and a ski mountaineering or “skimo” race in which participants go up and down mountains on skis. (Photo courtesy of Erik Chelstad)

Daily reads? Favorite sites and newsletters? I try to take “The Black Swan” author Nassim Nicholas Taleb’s advice and stay away from the daily flow of pop news and info. It’s more of a spectator sport than a life guide. That being said, I go for the weekly Economist and veg out on the Slashdot comments if I’m in line for something and need a dose of humanity plus science.

Book on your nightstand (or e-reader)? It’s at least three. I mean, one for sleeping, one for feeling like an instrument of change and one for fun if I just wake up too early: “Quantum Computing Since Democritus” by Scott Aaronson, “Requiem for the American Dream” by Noam Chomsky, and “Rich Man’s War” by Seattle author Elliott Kay.

Night owl or early riser? Both. Sleep is necessary and good, but circadians just aren’t my thing. Back when on-demand content started going mainstream, there was popularity with the concept of time shifting. I try to apply this to sleep, as at every tick of the clock, something amazing is happening somewhere, and you need to choose which things you are awake for.

Where do you get your best ideas? Airplanes. Something about the forced spaces (can I lift my arms to eat?), the simulated privacy (I’m writing, please don’t show me pictures of your grandkids), and the limited stimulation (really, they made more comic books into movies?) allow for some great mind wandering and strategizing.

Whose work style would you want to learn more about or emulate? I’d like to learn more about the work style of immersive science writers like Susan Casey. She must be really good at setting aside massive amounts of time to do work that is really creative and thoughtful, but with only her belief that it is going to succeed. She has to create stories and interest in very complex arenas. This is similar to any tech leader who is trying to convince people, not just to be casually interested, but to get them so excited they want to buy your product, invest in your company, or join your team.





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