An Interview on Entrepreneurship with Codesmith Sr. Advisor Eric Kirsten

As software engineers increasingly lead organizations across all industries, entrepreneurship becomes an important consideration. Our community of graduates embark on new challenges within their growing organizations, and many are forming organizations of their own. Since we are seeing growing demand for guidance around entrepreneurship, we sat down with Eric Kirsten, a Senior Advisor to the Board at Codesmith, to learn more about his background, the work he does with Codesmith, and his advice for aspiring entrepreneurs.

At Codesmith, Eric advises on strategy, graduate hiring, and outcomes. With a wealth of entrepreneurial experience, he shares his valuable insights with the Codesmith community.

• What is your role at Codesmith?
• What is your favorite part about working at Codesmith? 
• Why did you decide to work at Codesmith?
• Walk us through your professional background. 
• What advice would you give to someone looking to launch their own company?
• What advice would you give someone considering an entrepreneur route in their career?
• Would you recommend a would-be entrepreneur try to get hired at a company after graduating Codesmith, or is it better to just jump into starting something?

What is your role at Codesmith?

I’m very fortunate to have been a part of Codesmith for more than eight years now- since the first-ever cohort, in fact. My official title is Senior Advisor to the Board, but in actuality I split my time pretty evenly between strategic issues for Codesmith and hiring/outcomes for our graduates. In the first role, I get to work with some really brilliant leaders within Codesmith, and in the latter I get to have a front-row seat to graduates changing their lives on a daily basis. 

What is your favorite part about working at Codesmith? 

I think what I enjoy the most is being a part of a hiring program that prioritizes our students’ authenticity while simultaneously imparting a distinctive focus on the type of communication - both, technical and cultural - that’s required when those students graduate and need to represent their true capacity as mid-level (and above) engineers.

I was at a Silicon Valley tech company in the early 2000’s, and I can tell you that engineering culture back then was all about how many check-ins you could do in a day. And to be fair, there are plenty of startups where that’s still the situation. But the modern engineer is one who can communicate with a non-technical CEO, or an investor, or two-hundred salespeople, as easily as they can with a fellow engineer or a CTO. The modern engineer is strategic on product vision, can work well within a team, or build their own from the ground up, and can pivot easily between technologies - much of that stemming from a deeper understanding of how the tech all works “under the hood” - but the rest coming from a thoughtful approach to collaborating, networking, and even inspiring others. So I’d say that watching our grads incorporate this advanced level of communication into their own job searches has been the most rewarding for me, because in a lot of ways, it can be the hardest part to teach, and for them, consistently leads to incredible roles and salaries - not just for their first role post-Codesmith, but for their roles that follow after.

"Codesmith supports grads for life, so I speak to graduates from six or more years ago on a regular basis, and to hear how they’ve accelerated their own careers by utilizing what they uniquely know about all of this - it’s so ridiculously cool."

So many of them are founders and CEO’s now, and I guarantee their pathway there was smoother because of their deeper technical knowledge.

Why did you decide to work at Codesmith?

The initial reason I wanted to be a part of Codesmith was because of its founder, Will. I remember meeting him very clearly. I walked into his complete mess of an office and the first words out of his mouth were, “Does it not bother you that the best university in the world in the year 1096 is largely still considered the best university in the world?” He never talked about launching a “bootcamp” or even an advanced immersive program. His singular goal at that point was to create an engineering community that was centered around the unifying concept of excellence. But not in the exclusionary way that universities have conducted their admissions processes for hundreds of years; it was about offering true excellence to people, regardless of age or background, whenever they were ready to commit to the work. That really resonated with me.

I had recently gone through a corporate acquisition, and following a couple other projects, I was sort of feeling out what I wanted to do next. The acquisition wasn’t a huge one, but I’d been through others in my past, and I’d also worked in some very large corporate environments, so as Will dug deeper into this next-level hiring program for engineers, an opportunity presented itself for me to share lessons I’d picked up over 20 years of starting companies, leading large teams, and interviewing and hiring engineers in a variety of settings. I’m the son of two teachers, so it was exactly the kind of meaningful mission that I’d been craving, and there was no shaking me after that. 

"My first job was working as an assistant to a film executive at Universal Pictures. I answered phones, I read scripts, I managed schedules and correspondence. Not a typical gig for a law school grad."

Walk us through your professional background. 

Oof, that’s not an easy thing to do for a guy my age. If you yawn, I promise I’ll speed up… 

I’ll give the quick rundown, but at the same time it’s important that I point out up-front that, beyond my “tech side”, I’ve also been involved with film and television for just as long. So there are periods where I may have stepped aside from tech to focus on that world. What can I say? - it’s a little odd, but it’s how I’ve decided to live my life. I find there to be a really foundational synergy between technology and the arts, at least as far as my own brain goes, so I made a very conscious decision to pursue both simultaneously. It’s led to a lot of days that have ended at 4 a.m., but I don’t regret a thing. :)   Anyway, here goes - 

"Based on some stuff I’d written, I suddenly had an agent, and I found myself developing projects with producers who’d gotten some great films made."

I graduated from Duke for undergrad and then Georgetown Law directly after that - and btw, I never intended to be an attorney, so I never took the bar exam - and then my first job was working as an assistant to a film executive at Universal Pictures. I answered phones, I read scripts, I managed schedules and correspondence. Not a typical gig for a law school grad, but I’ve never really worried about that kind of thing. I was pursuing what I cared about at the time, and that’s what mattered. It was a great experience because I came to realize that the corporate side of entertainment wasn’t as interesting to me, at the same time I was discovering a world of technology and entrepreneurship that shifted my thinking completely.

I stuck a pin in my filmmaking aspirations, and I joined my first ever startup (after moving from Los Angeles to Denver), which was a (sorta) tech company focused on “distributed customer service” (i.e., intelligently routing customer service calls to at-home experts instead of the typical call center). Thrilling stuff, I know. It wasn’t groundbreaking, but what I’m most grateful for is that my role was in sales, because it was in that early role that I saw how deals and transactions actually get done - the networking, the pitch, the follow up, plus the kinds of things that actually inspire people. It was eye-opening in that I learned early on that having a great product was only part of the story. 

"One of the great bonuses to working at a tech-first organization is the opportunity to find potential co-founders… it can be a great pathway for people who don’t have super strong networks."

After that, I was fortunate to find my first real mentor. She was an engineer about ten years out of Carnegie-Mellon who’d hired me as a Project Manager at an organization called CableLabs, which is a non-profit, technical standards body for the entire cable industry.

Again, not earth-shattering in the traditional sense, but what it immersed me into, for the first time, was a first-rate engineering culture. Brilliance was everywhere, and I was suddenly surrounded by the kinds of engineers who could have each done anything they wanted, and yet were choosing to sit tight at a non-profit because it gave them the freedom and space to pursue their own interests in the midst of their day-to-day lives.

This was where I met my co-founders for TrueChat, which was a distance-based VoIP platform that you see in every video game now, but wasn’t a thing yet back then. We raised a quick $500k (from a cable company executive), built an absolutely sick prototype, and ended up being acquired by Terayon Communications in about a year for $12 million. 

"Make sure that the startup is based on a real passion, rather than just something opportunistic… the stress level will always be lower if your day-to-day is rooted in a world you really care about."

After that I ended up in the role of Director of Interactive Television for AT&T Broadband, and then eventually promoted to V.P. After that, the CEO of AT&T Broadband, Leo Hindry, recruited myself and about five or six others to be the founding executive team for GlobalCenter, which was a web-hosting spinoff from Global Crossing, valued at about $2 billion.

Based on the work I did at AT&T Broadband under Leo, I was brought into that new organization as the VP of Product Management (eventually becoming SVP), directly overseeing their Application Services group which was responsible for about $200 million in revenue. Just like CableLabs, the people surrounding me were bright and ambitious, and the challenges were pretty much endless. And again - just to point out here - I had zero experience in product management prior to taking the role.

But just like the role of today’s mid- and senior- engineer, it’s one that requires the ability to communicate with technical talent, salespeople, executives, etc. on a regular basis, and that was something I knew I could do well. So I jumped in, and it all turned out incredibly well. A couple years after taking the job and moving from Denver to Sunnyvale, CA, GlobalCenter was acquired for $6 billion. I stayed on for a bit after that, but the economy was brutal after 9/11, and my interests were moving back toward film anyway.

"Being an engineer is far closer to being a writer or a musician or an actor than it is a dentist, or a lawyer. If you’re good, you’re good."

Bored yet? Anyway, I spent a couple years focused on film development after that. Based on some stuff I’d written, I suddenly had an agent, and I found myself developing projects with producers who’d gotten some great films made. I did get paid to write a couple things, but Hollywood is Hollywood, and getting material across the goal line of actually getting made is extremely difficult (and so out of the control of any one person), so in 2004 (I think?), I decided to go for a role at ESPN that I was just instantly drawn to. The coveted job was Director of Programming (as in TV programming, not computer programming) for College Basketball and ESPNU (the first year of that network), and being a Duke grad, where basketball is practically a religion, I couldn’t resist. After all, it’s the largest sports media company in the world, and I’m admittedly a sports fan. I negotiated contracts with athletic commissioners, I got to pick which games were televised, I oversaw production schedules.

Amazing stuff, and I really enjoyed it. But when a different opportunity eventually opened up internally, I felt that pull back to tech, and I accepted the role to oversee Interactive Television, which was a very new thing for the network at the time. It required a lot to convince a network founded in the 1970’s to embrace new technology, but I’m proud to say that I launched ESPN’s first ever interactive sports experience during a Florida/Florida State football game.

It was around my third year there that I met Aaron LaBerge, who’s currently the CTO of Disney, but back then was, I think, ESPN’s SVP of Technology & Product Development. We hit it off really well, and our skills/styles complemented each other - major checkboxes before you decide to start a company together, which is what we did about a year later.

The idea was to create a user-generated content platform that allowed for product discovery from a foundation of film, television, sports, and pop-culture in general. In other words, if you saw a cool pair of boots on a TV show, you could come to Coolspotters.com (one of the platforms we launched) and find out exactly what type of boots they were, and also purchase them. We raised a couple small rounds, we signed Pepsi as a sponsor, and we ended up with a very active community of several million unique users per month, all while we were also launching apps for the iPhone. Life was good. And then the tech crash of 2008 happened.

I talk to Codesmith grads all the time who are stressed about the macroeconomic stuff going on. And it is a real thing, so I’m not at all trying to downplay it. But I can’t stress enough how much worse the tech pullback was in 2008 compared to today. Yes, the second half of 2022 and most of 2023 were on the rough side regarding the job market and everything else, but back then, there was this feeling that it was truly game over. Institutional money had dried up completely, with a partner at Norwest Ventures literally telling me that if I was ever gonna “move off to some corner of the earth and just hunker down,” this was the time.

It’s wildly arrogant to say it, but I really think the reason Fanzter (which was the parent company) didn’t get bigger than it did was because it was a little ahead of its time. Cue the eye rolls, I know, but the engineering team at Fanzter was so next level. They were the epitome of who I’m describing when I talk about “passionate engineers who just love to build.” The talent was incredible, but the reason they were so incredible wasn’t because they were great Python engineers, or great Ruby engineers. It was because they were just great engineers. They anticipated user needs, they iterated, they tested, they collaborated constantly.

In fact, the entire platform ended up being built in Ruby on Rails, and our lead engineer had never even worked with Ruby before. But his capacity as an engineer was so on point, that we of course never cared about that. 

We talk a lot at Codesmith about this concept of “engineering capacity” and autonomous problem solving vs. the more outdated idea of focusing on “years of experience,” and I’m so grateful that we do. Being an engineer is far closer to being a writer or a musician or an actor than it is a dentist, or a lawyer. If you’re good, you’re good. You don’t need to know everything, but if you’ve got what it takes to graduate from the rigor of Codesmith, can find your own answers to questions, can work cohesively as part of a team, and communicate across all technology skill levels, then you’re at least a mid-level engineer.

I’ve hired a lot of engineers in my life, and the great differentiator between top-tier talent and the “typical engineer” is almost never their technical ability - it’s all these other pieces, which are so, so hard to find. Anyone can learn to code fast and do a bunch of check-ins. But try finding an engineer you’d put into a pitch room with a group of experienced tech VC partners, or onto a stage in front of 200 sales people. That’s the kind of thing that Aaron does easily, and one of the many reasons I was excited to partner with him.

So, anyway– I stepped away from Fanzter/Coolspotters as a full-time thing around 4 years after launching it because raising a follow-on venture round in that economy was still tough, our margins were thin as hell, and the company was able to operate with a small team. Since I still owned about a quarter of the company, I stayed closely involved, but I was also ready to take a break from the 14 hour days. Roughly a couple years after that, Disney acquired the team and the technology that we’d built. 

After that, I did one year as a CMO/Founding Partner at a VC-backed healthtech company in New York City (living in the city during the week, and then commuting home to upstate Connecticut on the weekends). I was back to negotiating big partnership deals, and co-designing a wellness platform that was built in conjunction with the Cleveland Clinic.

All very cool. But at the same time, I had two young sons who were acting in school plays and playing little league, so in the end, my wife and I made the decision to stay in Connecticut, rather than relocate to NYC, which is where I would have had to have been for the job long-term. I don’t regret the decision at all (even though that company ended up getting acquired as well).

"During almost any investor pitch, there’s a time when you have to put up a slide on your background… I promise that having done some deeper work at respected brands makes that smoother. Track records matter when you’re asking for millions of dollars."

Following that, I did a little less than a year as the Global Head of Digital for Aetna Insurance, conveniently located in lovely Hartford, Connecticut, overseeing a series of great product teams. I hope I did a lot to improve the lives of their customers, but I’m never gonna be a jacket-and-tie type of person who adores corporate culture, so I decided to leave that as well. Again- what can I say? It’s how I’ve decided to live my life. A year here, five years there… I don’t know. I follow my passions, and I’ve learned that it’s a strategy that usually leads to good things.

So, post-Aetna, and with no startup ideas to pull from, I started writing creatively again, and I ended up writing a feature length film script that got a bunch of attention in the world of literary agents and producers. It led to a deal with a Warner Brothers production company…which led to another deal with a different production company…and so on. Companies were paying me to write, so I went with it, and one of them even got made (not my favorite of the bunch, but whatever; it made $28 million on a $3 million budget, so a win’s a win). The next phase of my life looked clear. 

And then I met Will. So, after a few years of Hollywood, and a lot of years building and launching tech companies, I was just at a point where my soul was craving real impact. Codesmith was everything I was looking for, and I guess it was the right decision because I’m still just as excited about it almost nine years later.

"Make sure that the startup is based on a real passion, rather than just something opportunistic… the stress level will always be lower if your day-to-day is rooted in a world you really care about."

What advice would you give to someone looking to launch their own company?

I talk to a lot of Codesmith grads who are interested in launching their own companies, and over the years, many have done it successfully. And the first advice I give is to make sure that the startup is based on a real passion, rather than just something opportunistic. Startups rarely go like you expect them to go, and there are so many macro-type issues out of your control, but the stress level will always be lower if your day-to-day is rooted in a world you really care about. 

I also recommend having at least one co-founder, because there will be plenty of emotionally exhausting days, and it’s pretty critical to have a real partner who can relate. I think the best co-founders can often be ones who complement your own skill set, but with most tech companies, the product is everything for the first phase, so two or three engineers can definitely launch a company successfully, as long as they at least have some reliable advisors for legal and financial matters, because those are inevitably going to show up before too long.

"Raising money is time-consuming and forces you to give up a certain amount of control… wait until the lack of financing is genuinely holding you back. Your pre-money valuation is going to be higher and there’s a better chance you’ll have investors who are truly bought into your vision."

“What’s the best way to raise money?” is another question I hear a lot, and the truth is, it probably shouldn’t be your first priority. Focus on the product, as well as getting some alpha/beta customers, then iterate based on the data from those customers, and then continue that cycle for as long as possible before pitching potential investors. Raising money is time-consuming, and it forces you to give up a certain amount of control, so I’d wait until the lack of financing is genuinely holding you back. Your pre-money valuation is going to be higher if you wait, and there’s a better chance you’ll have investors who are truly bought into what your vision is. And hey- if you can launch and grow without taking any outside money, then even better. There are no rules to it.

"For engineers, I recommend spending a lot of time with investors, not to raise money, but to learn the vernacular. You don’t need an MBA to launch a company, but you have to know how to talk to MBAs."

What advice would you give someone considering an entrepreneur route in their career?

First off, I’d make sure that you’re in a period of your life where you’re ready to give virtually everything to your venture. If you’re doing it right, work/life balance will be really, really hard to manage, because that’s truly what it takes to build something successfully. Having a young family made it really hard for me to be away as much as I was, and as I already mentioned, I did decide to put them first at certain points in my career. But everyone’s different, so it’s a matter of self-reflection and deciding what matters most to you.

For engineers, I’d also recommend spending a lot of time with investors (associates and principals at VC funds are perfect) - not necessarily to raise money, but to learn the vernacular. There’s a very specific language that finance folks use (pre/post-money, non-participating liquidation clauses, 409A valuations, etc.) that’s best picked up by spending time with the investors themselves. You don’t need an MBA to launch a company, but you have to know how to talk to MBAs. 

"During almost any investor pitch, there’s a time when you have to put up a slide on your background… I promise that having done some deeper work at respected brands makes that smoother. Track records matter when you’re asking for millions of dollars."

Would you recommend a would-be entrepreneur try to get hired at a company after graduating Codesmith, or is it better to just jump into starting something?

Like most of these types of questions, the answer is ‘it depends.’ We have residents at Codesmith who’ve already started organizations, or come from pretty extensive corporate backgrounds, and so for them, maybe the right answer is to become a Founder/CEO. But I’d say generally, there’s a ton of value to be had from gaining experience first. 

During almost any investor pitch, there’s going to come a time when you have to put up a slide on your background for everyone to see. And I can promise that having done some deeper work at one or more respected brands is going to make that a smoother experience. Track records matter, especially when you’re asking for millions of dollars. 

Beyond that, one of the great bonuses to working at a tech-first organization is the opportunity to find potential co-founders. I’ve done that a couple of times, and it can be a great pathway for people who don’t have super strong networks. You get a chance to see how people work in a professional setting, and you get insights into what they’re good (and not so good) at. Whether you find your co-founder or not, you’ll be motivated to get to know the people around you, which comes with a ton of intangible benefits either way.

It’s important to remember that it’s also not an all-or-nothing kind of decision. I started companies while working full-time because I was willing to sleep less. So for people who have that level of grit, it might take a bit longer, but both can be done at the same time. You just have to be careful not to let your physical and mental health go to hell because it can be a lot at times. But if you’re doing something rooted in an authentic passion, it will be far more energizing than anything else.