Chris Stahl, CEO and co-founder of Portland-based Knapsack (www.knapsack.cloud), joined Cascadia Report for an interesting and heartfelt discussion about his career to date, what it takes to start your own business, and his passion for the tech community here in the Pacific Northwest.

Stahl is a serial entrepreneur, startup CEO, and more recently — a podcast host. He is excited to see how Knapsack is going to change the way we think about building software applications using pattern-based experiences from reusable design and code.

As the CEO of an ambitious Cascadia Innovation Corridor tech company, I started by asking Stahl what he loves about his role at Knapsack, and what the day-to-day work involves.

Chris Stahl, CEO and Co Founder at Knapsack.cloud

“The day-to-day changes a lot. It's a startup company so there's a number of hats that I'm wearing on a day-to-day basis. Right now, I'm really focused on fundraising to take the next step in our company's journey. A big part of that is spending a lot of time meeting with venture capitalists and angel investors trying to get feedback on our ideas, trying to raise money, and spending a lot of time building out those materials. Luckily, I have an amazing team that helps me continue to run a lot of the operations side of the business.

I get to work with a lot of really incredible people. Ultimately organizations are about the people that are in them. Obviously, I believe in the mission of the organization and what we're trying to do. We're changing the way that people think about building websites, but also just getting to work with a lot of really incredible folks that are very talented and passionate about what they do.”

A brief look through Stahl’s career reveals a wealth of experience in leadership positions for companies large and small, largely focused in the technology industry. From positions with SAP and General Electric to his more recent roles as CEO of Basalt, and Knapsack, I asked him how his journey started and what had kept him in tech in the Pacific Northwest.

“It all goes back to an experience I had in college. After my freshman year of college, I was faced with the choice of moving back home or going and finding a job somewhere, and I didn't want to move back home. So, I moved to Seattle and my aunt very graciously took me in. I met a friend of hers at a party that was a venture capitalist, she was working with a company that needed an operations manager. She set me up with a job as she also needed somebody to house sit while she was away. It was a place to live, and a job in the interesting world of early 2000s startups in Seattle.

It was an exciting time to be a part of that world and to see it from the inside. I got a taste of it then when I was all of 19 and it stuck with me. After I finished school I went and worked in Big Tech for a while at General Electrics and SAP and ultimately decided that wasn't for me. I got back into the entrepreneurship side of things, starting a company focused on providing accounting solutions for the beer and wine industry, and that was a lot of fun. I sold that business to my partners. That was my first real successful exit, and that company is still in existence today.”

By now it was 2008 and internet startup businesses were seeing huge growth, being at the forefront of the industry with a solid track record behind him, Stahl looked for his next career move.

“I joined a small startup in Boston called Acquia. And that ultimately became a company that went the path of a unicorn. It became a billion-dollar organization. It was awesome to watch that evolve and grow, and it had a huge impact on my career. Getting to see what a well-financed, well-run startup looks like from the inside and to be there relatively early in that company's journey was amazing. I decided while I was there that that's what I wanted to try to do next. But I needed some additional skills before I really got there so I worked at a couple of agencies, did some independent consulting in that agency landscape, found my passion for sales and also this passion for building these large repeatable systems for big enterprise customers. That's how I got to this point.

Finding my co-founders was the last step in that and knowing that I wanted to work with people that I really loved working with that were super passionate and that I could rely on and trust. What better group of people to draw that from, than the people that are your closest friends? The company as it exists today was  founded on chairlifts and airplanes, going on adventures in the Pacific Northwest, and across the world, talking with folks that I loved and deciding to build a company together.”

That entrepreneurial spirit may have come alive after trying out a more conventional career, but Stahl had already experienced building a company of his own. He founded Sentinel Online in 2003, an experience he remembers fondly as a ‘great experiment’ and as valuable firsthand experience of the tech industry.

“It was just after the summer in Seattle. I was still in school and we had a big problem that we were facing, transcript management. I was technically a transfer student because I had taken a bunch of community college classes and managing transcripts was a really hard thing to do. You had to go and get embossed signatures and send all these official copies of transcripts everywhere. It was a horribly inefficient process which took weeks. And oftentimes there was mistranslation or delay in the process.

The director of the entrepreneurship program at WSU and I were talking along with some other friends about how to make an electronic version of that paper process at that time. It was a great idea, but ultimately it never really went anywhere largely because the legal environment around universities is a bit much for a three-person team to tackle. Though we did build some awesome tech and got a lot of the thinking started about what a new entrepreneurial venture is, and how important it is to make sure you can reach your customers.”

Bryan Hall at Washington State University


Bringing it back to 2020, Stahl co-founded Knapsack in April on the back of a successful agency, Basalt, that built design systems for large enterprises. Realising that the company had created a product that was in demand, they began experimenting with the idea of pivoting the business.

“The agency was successful by all accounts. We were a little bit more than a million in revenue after 18 months of operation, things were going really well. But we sat down and said, I think that the product that we have, this nascent product, based on all this tooling that is probably more valuable and useful to the world than the agency business ever will be. As an agency we were just another agency, as a product company we have the opportunity to really change the way that people think about building websites.

We started a beta program, launched a podcast, did some field marketing, and made some initial hires to move in that direction. And by March 2020 we'd completely changed the business over from a services organization to a product organization. We launched the product in March, changed the company over in April. We didn't finish the final incorporation change of our paperwork until September, so it's been quite the evolution.”

Workflow design and automation is a hot topic for businesses around the world, particularly as the COVID-19 pandemic has accelerated the pace of digital transformation. I asked Stahl what drove him to create the business, what potential he sees in space, and how Knapsack are looking to find their own niche.

“My friends and I started it together. We all worked at an agency and we kept having this ‘Groundhog Day’ experience where we would sit down to implement a big web platform at a major organization. The process would be; create a business requirements document, set up a design team & a development team, build out a list of requirements, create tickets in your ticket tracking system, do the development, do the testing and launch the product. Then you'd throw all that away and start over again with the next part of the platform or the next site to go live. That struck us as a really inefficient process and so my co-founder, Evan, and I said there's a better way to do this.

There was a project we were working on for a cosmetics brand. We decided to create an abstract re-usable set of front-end pieces that you could put together into whatever you wanted. We did that and it worked, we saved a bunch of money on that project. Our agency at the time wasn't that interested in building a practice area around it so Evan and I decided that we'd start an agency around it. We had some other earlier partners that were part of the organization too, that have since moved on to other things.

That became our passion — how do you take these builds, where you have these big organizations that are trying to build dozens or hundreds of websites and make that so it's not this just wasteful, inefficient process? Through that journey we figured out that lots of other companies can benefit from this too, smaller organizations that are just starting out, organizations that are focused on e-commerce, or healthcare and finance. They all have this common need of the ability to build and maintain their web properties with patterns. So that's what we based our business around.”

In addition to building out their company’s product offering, Stahl and the team at Knapsack got to work on delivering a podcast that he describes as a ‘cornerstone’ of their success to date.

“We have a somewhat unorthodox approach to how we talk about what we do. The Design Systems Podcast is all about having conversations in the community. It's not about us pushing our product or talking about who we are. It's about putting the focus on experts in the field and having a really insightful conversation with them to try to show people different points of view about what the future of the web and design and development look like. That's been a really incredible tool for us both just to contribute to the community and to emphasize a lot of voices inside of it that really should be heard.”

A career is rarely straightforward and what we planned at the start, and although Stahl acknowledges that he has ‘always been in a privileged position’ that has not made him complacent or ungrateful about that reality. I asked what challenges he had faced in that context, and he was keen to talk about a few issues that many company founders in the Cascadia Corridor might be able to identify with.

“I think one of the hardest parts has always been this lure away from the Pacific Northwest. Some people might view that as not really challenging, but for me, like I've grown up here. I love this place. I've always wanted to be here. It’s been important to me to partially fund this business out of the Pacific Northwest. It’s been important to me to be somebody that is invested and involved in the community here. When I first started working at Acquia they tried to pull me to Boston, and I ended up starting the Portland office for Acquia. Likewise, when I worked at Phase2, they tried to pull me over to DC, and I just ended up starting the Portland branch of that agency.

I've always viewed my role as somebody that has a lot of roots here that wants to continue to stay here and bring awesome jobs and awesome careers to people in this community. It's always been important to me to look for those opportunities, to give back and to do it when I can. Adversity wise, in my career, I've always been an overly ambitious person when it comes to startups and ideas. I've always had these really big ideas that oftentimes require a lot of buy-in that are based on that idea, not based on the reality of how that idea is working yet. Being able to find people around me that also believing passionately in those same instincts has been challenging. But overall, my challenges have been relatively small relative to so many other people and it speaks to the privilege that I've had. And I feel very fortunate for that.”

As a company founder with so much personal and professional investment in the region, I asked Stahl what companies he had collaborated with in the Cascadia Innovation Corridor in the past. And, by the same token what elements he feels the Pacific Northwest is missing for the tech industry.

We've collaborated with several agencies here. Helpful Human have been awesome to chat with recently, we've also spent a lot of time with other founders of other small startups like Botany.io. Lots of folk have been super supportive and helpful of our startup journey. The Pacific Northwest, Cascadia is home to a lot of people that work at other organizations that are a lot bigger that have also been super supportive of us.

We have friends at Amazon and Microsoft and folks that come from places like Adobe that live and work up here, participate in things like the Seattle Interactive Conference. Those are all wonderful people to get to know and work with in this community. We've also kept a lot of our customers local. Working with Mercy Corps has been incredibly rewarding, and Cambia Health Solutions. We've tried to keep at least some part of our presence local because that helps us remain tied to this area.

Finding venture capital is still really hard here. There is a huge pull for me to go raise money in Boston or New York or San Francisco. I'm trying to remain really committed to being here. It's interesting the take you get from other entrepreneurs; some say don't even spend your time here, that your time is way better spent in San Francisco or in New York. And then there's other folks that have at least found part of their funding from this area in this region.

It's a real mixed bag and it's definitely one of those things where, having more people in the startup community, having more people that make this place feel like a really friendly environment for entrepreneurs, is a hard challenge. It's not like people aren't taking the steps here. There's lots of people that are trying to lead the charge in this area, but we need to continue to be this robust community. I feel like it's not just something that's a Seattle problem or a Portland problem or a Vancouver problem. It is a regional thing that we need to think about especially in the age of COVID and Zoom, how we are open about investments across this region, not just within our single cities.”

While many people share Stahl’s passion for business and startups, it’s invigorating to hear someone with a real commitment to the region that they have grown up in and a dedication to helping to drive growth and prosperity in the local community.

As someone taking a lead in promoting business and the startup community in the Cascadia Innovation Corridor, I asked Stahl how he approached leadership within his business, and what advice he could give other founders and CEOs in the region.

“You're in a situation where your job is to have opinions about everything, but at the same time it's also to hold up the opinions of the people that are closest to the work. I view my role as CEO and the role of the other executives at the company as one of fostering communication. You're the conduit through which information flows and as the CEO you probably have the single best viewpoint of all aspects of the company. It is your job to inject your thoughts and opinions at the right moment to put people on the right pathway, and then just support them as they run with those ideas. It’s important to me to not be viewed as a decision maker and authoritarian. There are times where I need to just make a decision, but on the whole I'm there to offer opinions and guidance to other people that are better suited to make decisions about their individual problems and challenges than I am.

Management is a skill, it's one of those things that doesn't come naturally. Just because you're really good at tech, design, finance, or whatever it is that’s your superpower that helps you start a business, it’s not the same as managing people. Being a sponge from everybody around leadership, coaching, learning how other entrepreneurs have done it, is an incredibly important step and evolving your own leadership style. I think that I would not be very effective at what I was doing, if it wasn't for the people that I leaned on to support me to help learn how to do this, and I'm still learning more about it every single day.”

Talking with Stahl, it is apparent that he understands the value of learning new skills, and investing in both personal and professional growth. With that in mind, I asked him to leave us with three key takeaways from his journey so far.

1. Whenever somebody tells you, how long it's going to take to do something, to assume it's the most optimistic case. Everybody has a hard time being realistic about things because I think as humans, we're just terrible at estimating time. You want to work with optimists, the people that will tell you those ambitious timeframes, but just understand that almost all the time somebody is giving you the most optimistic answer about how long something's going to take.

2. Surround yourself with great people that are better than you. You don't have to be the smartest person all the time. You want to be surrounded by people that challenge you, that you have a lot of professional respect for that you can learn from. Passionate incredible people breed incredible ideas, which gets more passionate incredible people interested in what you're working on. It's as much about your ability to build a team as it is your ability to do a thing.

3. Practice mindfulness. Doing things with intention and with a thoughtfulness how it's perceived and affects other people is a really meaningful exercise for nearly any important action that you can take, as a business leader. Thinking about how it reflects upon you, how it reflects upon the people that are most affected by that action and taking time to pause and understand your intention behind it is an incredibly valuable step. That three second pause to think through the intention of the impacts of your decision is a really important step in maturity of leadership.”

You can find out more about Knapsack here: http://knapsack.cloud