In conversation with
A founder on her path from IT, product management, and board advising to leading her own companies
From computers to medieval literature—and then back to computers
Hi, I’m Betsy Bilhorn. My origin story for getting into tech is pretty interesting. I majored in English in college because I was sure that medieval literature was “it.” I didn’t have a technical background besides the fact my dad used to work for [mainframe and supercomputer firm] Control Data back in the day. We had computers in the house all the time, but it was the typical situation: my dad did computers, so of course, I did not want to do so.
My life plan consisted of going to work for a bank and making lots of money, but that didn’t quite work out, because when I graduated, there was a recession going on. Because it was so hard to find jobs, I ended up taking a data entry position at a health insurance company. I wanted to move up the ladder, so I moved to a position in the annuities department, which back in the ’90s meant using some basic PC software.
We didn’t have an IT team, so we were on our own—no one would come to fix things. Eventually, I had enough, so I went and bought some books about our database, taught myself how to crack into it, fixed it... and got caught. I got called into the VP’s office and was reprimanded because hacking into our systems and changing the code meant I was in big trouble. However, my punishment was being transferred to the IT department, and the company paying me to go back to school at Portland State University to get a computer science degree.
I’ll be honest, I was 23 and accepted because I was trying to make more money. Lo and behold, I was good at engineering. It was fascinating to me. The other side of this is that I have always loved talking to people. The IT team would send me out to communicate with everyone because that meant they didn’t have to [do it themselves].
From that job, I went to a big bank, which was not for me, and then to a small startup in consulting, which was much more my speed. We did consulting work for large financial institutions that were leasing right around all the Y2K stuff, and I got to talk to a lot of people. We were also working to build custom apps for our clients, so developing the conversations around what the customer needed and what parameters were required is what started my product management career, even though I didn’t know it at the time.
Product management and business development
I was at a company called Webtrends doing hardcore IT and I began to realize I didn’t like it anymore. I felt a step removed from the business as massive product decisions were being made and I wanted a seat at that table. I transitioned into a business development role at Scribe because it seemed more aligned with what I wanted to do.
However, there were a lot of things that we were not doing or investing in when it came to product, and I was confused. I ended up writing a Jerry Maguire-style email to our founder and asked him why we weren’t looking at this, why are we aiming for these markets, what about the cloud, et cetera. He came back to me and asked if he could send my email to our chairman. I was convinced I was going to get fired—I even started to look for other jobs. In the end, they told me they thought my ideas were great but they also called my bluff: I was now in charge of product. That’s how I officially got into product management. Scribe ended up releasing one of the first cloud integration platforms-as-a-service and I knew I had found my sweet spot on the product side of engineering.
Dealing with tech debt
One of the biggest tightropes to walk is managing innovation and wanting to adopt new technologies—while also maintaining reliability and not generating too many bugs. The board always wants to move faster, drive sales, and create exactly what the customer wants when they want it to stay ahead of competitors. This mindset is what leads to fun questions like, “Can we have blockchain by tomorrow?” That’s not realistic.
That’s where the idea of tech debt comes in. Coming from an engineering background, I had more empathy for the engineering and QA side when they would come to me and say that our bug debt was too high and they needed time to clean up the code.
Now we call it site reliability, but back in the day it was “business continuity and stability.” To continue driving forward while also focusing on maintenance, we would reserve about 25% of each sprint or development stream to focus on stability and performance. Of course some days we needed to add a little more time or not need 25% of the time, but it established a foundation of integrating reliability into our development process.
Another aspect of avoiding tech debt was making sure we invested in the right tech for our stack, not just what the most popular thing was. I was smart enough to know when I was being BS'ed when people would come to me and say that we needed to change the SQL database to DynamoDB. My first question would be, “Why?” People didn’t like that very much, but I had the technical knowledge to ask the necessary questions. Being able to find the balance between the technical side and the business development side has been very beneficial throughout my career.
Joining the board at ChaosSearch
I was introduced to Tom Hazel, the CTO and Founder of ChaosSearch, through a mutual connection when ChaosSearch was only about three people. We sat down to have what was supposed to be a 45-minute lunch, but once we started geeking out about the technology and he told me more about it, it quickly became a three-hour lunch.
What attracted me to ChaosSearch was that it was completely different [from] what I had been working on, and the technology itself was cool and so disruptive at the time. These two things were the driving factors that made me want to be a board advisor. I also always knew I wanted to be a founder one day, so working with companies that were at a very early stage was a great learning experience. And working with other technologists [and founders] like Tom is like learning through osmosis: you get to see the same problem sets from a new perspective. Acting as a board advisor also lets you see the commonalities of the founding experience—everybody has process issues with agile, investor pressure, HR struggles, and so on. It helped me realize I wasn’t going crazy all the time and that I wasn't alone.
Learning to bounce back
My first foray into founding was a company called DigiPonies, which is funny because it was very similar to the concept of NFTs. You could create your own pony that would be unique and owned on blockchain. You could then use the image to create t-shirts, mugs, whatever you wanted. The second aspect of it was that you could breed more ponies interactively through the app.
I wrote out the DNA engine in the backend. It was cool and exciting…until COVID-19 hit. Our supply chain from China went down immediately. I was also trying to get investors interested because I had been bootstrapping the company. I kept trying through March, April, May, right as COVID really got started. People just didn’t know who I was. Especially at the earlier stages, getting funding is all about who you know. I officially shut down DigiPonies that August and put it on the shelf. From my experience as an advisor, I had seen the struggles and knew that I had to manage my limitations and what I could do on my own.
Trying again with Trender.ai
I was really scared to put myself out there as an entrepreneur again after DigiPonies. However, a year into founding Trender.ai, I can stand here and say that I'm stressed, that I’m working harder and more than I have in a long time, but that I am the happiest I’ve ever been. I had to pick myself up and dust myself off after a big failure, and I didn’t want to fail a second time. I had to relearn having faith in myself. I committed to doing something and doing it right, and it has been very rewarding to see this company grow.
Starting to build with security in mind
Take account of things like architecture and security as soon as possible. Sometimes you want to build new things, but then it might not scale or you have to change out your entire backend or security. As someone who has had to turn around and refactor an entire codebase and add in security after the fact, it is a nightmare—especially when it's a five to ten-year-old codebase. It can take years. You will save yourself so much time by factoring in security early on. That has been the nice part of working on Trender and social media: so much of accounting for privacy, security, and governance is baked into the process, right down to the UX. It’s a conversation that threads through everything.
Mentorship and hiring at an early startup
No one knows who we are yet, so we can’t always get the most seasoned people in the tech and engineering industry to join our team. It’s more like bringing up the next generation of tech rockstars and setting aside time to make sure I’m there for them and available as a mentor. This was an adjustment for me after being in senior management positions for so long, but being ready to invest time into your new employees is an important step as a new founder. When we’re hiring, we look more for the passion and the willingness to join the journey with Trender more so than needing to have X amount of experience or being a technical expert. We’ve taken a chance on almost everyone we’ve hired so far, and they have all been phenomenal. Look for the passion first, because you can always teach the rest along the way.
I’m gonna expose myself here, but I am a pretty heavy gamer. Zombie games are not normally my thing, but I just finished The Last of Us and The Last of Us II and it was like being in a movie, so cool. I geeked out and listened to all the podcasts about it and all that. The designers created an emotional experience so you feel the pressure and the fear.
I’m also currently playing a lot of Elder Scrolls online. It’s a great stress reliever for me because you just get to run around and do quests—it’s so fun.
When it comes to books, I just finished reading The Everything Store about Jeff Bezos and establishing Amazon in the early days. My main takeaway was that even though you read all about these guys like Zuckerberg, Elon Musk, and Bezos starting their companies and seeing how successful they are now, they all had moments on the edge where they didn’t know what they were doing and they almost didn’t make it. They didn’t have it all figured out. As a founder in the first year of their startup, it’s reassuring to hear the whole story. I quote that book a lot with my team to remind them it’s okay if not everything is okay. It helps take the edge off.