Editor’s note: From Cisco to Automated Insights (formerly known as StatSheet) to machine learning startup InfiniaML, Robbie Allen has been one of the Triangle region’s most aggressive and boundary-pushing entrepreneurs. He recently left Infinia and has launched a new company – Startomatic based on the concepts of Ikigai – along with veteran attorney Andrew Fisher. In his own words, here is Robbie describing the adventure to become “what I want to be when I grow up.”

RESEARCH TRIANGLE PARK  – I’m Starting a New Company. Why? Ikigai
After working for 23 years, I finally have a handle on what I want to be when I grow up.

Ikigai is the intersection of your passion, profession, vocation, and mission.

A few years ago, I stumbled on the Japanese concept of Ikigai and it really resonated with me. In the entrepreneurial world, you’ll often hear that you should “follow your passion,” but I’ve learned that advice is incomplete. Ikigai, as it applies to your career, goes beyond passion to include not only what you love doing but what are you good at, what the world needs, and not to be forgotten, what can you make money at.

I’m excited to announce that I’m starting a new company with Andrew Fisher called Startomatic, and it’s the best intersection of my Ikigai so far. It’s taken my whole career to figure this out. Let me tell the story of how I got here.

Ikiagi from Robbie Allen’s posts about his new venture

As I’ve written before, it’s important to work on something you enjoy doing. Your career takes up a big part of your life — would you rather do something simply to make money or work on something that doesn’t actually feel like “work”? I think most would agree it would be better to do something you enjoy, but that’s where the advice falls short. By definition, you are passionate about a small number of things but how many of those are great business ideas? I’m passionate about my two kids, but they have a tendency to generate more expenses than income 🙂

At least for me, it took a number of years working in different environments and doing different types of jobs to figure out what kind of job and company would create the biggest intersection in the Ikigai diagram.

I found what I’m good at early

I’m one of the lucky few that learned the line of work I wanted to do at a young age. I was a sophomore in high school when I took a “Business Machines” class and saw my first computer. From that point forward I knew I wanted to do something related to computers.

In 1997, I was a junior in college and did an internship at Cisco in Research Triangle Park, NC. It went so well my manager asked me to move out to San Jose, CA and join the company full-time. I jumped at the chance even though I’d have to finish my degree in my “spare time.” For me, the whole point of college was to get a good job, and if I got one without first getting the degree, that was ok with me.

I also thought I might work at Cisco my entire career. My dad worked at AT&T for 30 years. I thought you go to college, join a company, and work there until you retire just like he did (by the way, he was pretty miserable with his job most of the time).

Cisco was a phenomenal experience for me. I got to live in Silicon Valley during the dot-com boom (and bust). Because Cisco was growing so fast, I was given more opportunities than most early 20-year-olds. Plus, the money was good. Ultimately, I became a Distinguished Engineer, which is one of the top engineering positions you can get at Cisco. I was really fortunate, but despite that, after 10 years, I wasn’t enjoying it. I got tired of the big company politics, endless meetings, and the feeling I wasn’t actually making a difference.

If we look at the Ikigai diagram, I was getting paid nicely and was doing something I was good at, but I wasn’t loving it and I thought I should be making a bigger impact. I knew that simply having a “profession” was not going to satisfy me.

Cisco was a great job, but in the end, I just wasn’t into it anymore.

What I learned from following my passion

Once I started to think Cisco may not be for me long-term, I decided to go back to school. I finished my graduate work at MIT in 2006, and I was dead set on starting my own company. Just one little question: what would the company do? The “follow your passion” advice was really popular then, so I made a list of all the things I was passionate about. That list consisted of “web programming”, “doing interesting things with data,” and “UNC basketball.” The website I created at the intersection of those passions was StatSheet.com.

StatSheet was one of the first websites dedicated to advanced sports analytics. Over the next three years, I developed a lot of code and had a ball doing it. In 2010, I raised my first round of funding. But it turns out not enough people wanted to pay for StatSheet’s analytics — the market was just too small, and there was a lot of free content to compete with.

Returning to the Ikigai diagram, StatSheet was lacking in two areas. It wasn’t something the world really needed, and very few people wanted to pay for it. Sometimes it (literally) doesn’t pay to follow your passion.

I really enjoyed working on StatSheet but it was hard to make money at it.

Show me the money!

A year after raising our first round of funding, we rebranded StatSheet as Automated Insights and started selling Natural Language Generation (NLG) technology to large organizations. The pivot moved the business away from my passion-play and towards something that could generate more revenue.

Running Automated Insights was fun and I learned a lot, not only about building a great team and good culture, but about what I liked doing and what I did not. Eventually, I stopped programming and focused on more “strategic” duties as the CEO. We raised a Series A and B. The company grew to over 60 employees. Then we had a lucrative acquisition by Vista Equity Partners in 2015. I stayed on for a couple of years after the acquisition, but running an ever-growing company wasn’t my jam. I decided to step back in 2017 and pursue a Ph.D. in Computer Science at UNC.

Shortly after starting my Ph.D., I was approached to build a new machine learning company called Infinia ML with noted ML researcher and Duke Vice Provost for Research, Dr. Larry Carin. Larry likes to say that Infinia ML initially “collided with the market” by taking on a number of bespoke machine learning projects across a number of industries to see where there was real opportunity. We built an elite team of 20 data scientists (half of which have a Ph.D.) and 10 ML engineers. It’s the smartest collection of people I’ve ever worked with or will ever work with. Even better, they worked together amazingly well. But after a couple of years and 30 completed projects, it was clear the company’s best opportunity remained as a tech-enabled services company to help large companies implement machine learning, rather than developing a standalone product, which is what I was brought in to do. I think there will be very few if any, pure ML-product companies, but I’ll save that for another post.

With this realization about Infinia’s future direction, the board and I agreed that the company would benefit from leadership that could help scale Infinia’s services approach in the enterprise market. At this point in my career, I want to focus on developing a product. So in November 2019, I transitioned out of the company as CEO. I will continue to remain involved as an advisor and support the company however I can.

Automated Insights and Infinia ML had the opposite attributes of my StatSheet experience. The world needs ML and NLG and we could get paid doing it, but I was too far removed from building the technology, which I really love doing. While I’ve successfully built large teams and have a good handle on what it takes to support a growing company, if I’m being honest with myself, I like it better when the team is small. The smaller the better.

There are sizable markets for NLG and ML, but I’m interested in building a small product team.

What’s next?

Now I’m 23 years into my career, I think I finally have a handle on my Ikigai. That doesn’t mean I feel like I’m behind or it took longer than it should have. Some people go their whole career without finding their Ikigai — my father is one example I know well. I was lucky enough to know what industry I wanted to work in while in high school. It’s unrealistic to think that you’ll find the ideal job after just a couple of years or even after just a couple of jobs. It takes time. Not to mention your Ikigai can evolve over your lifetime just as you evolve as a person.


But for now, I know I want to run a small, profitable tech company (vocation/profession) where I’m developing the technology (passion) that helps entrepreneurs (mission). The “profitable” part is a nod to the fact that I want to build a company without outside funding this time around.

Why the focus on entrepreneurs? When I was working on my Ph.D., I had an idea that entrepreneurs in the earliest stages of company creation are underserved by technology. I had a great experience running my own company and think there are many more people that could be successful entrepreneurs if they were willing to “take the leap.”

There is too much friction in the process of getting a company started, which prevents many from even trying. It costs thousands of dollars and several weeks to get a company incorporated. Not to mention all the knowledge you have to assimilate about sales, marketing, finance, HR, etc. How many other Robbie Allen’s are stuck at Cisco and could successfully build a company if they had better support?

I was surprised by the lack of solutions to help entrepreneurs get off the ground. Many existing solutions are either bloated legacy providers that attempt to do everything for everyone (Salesforce, QuickBooks, etc.) or a massive hodgepodge of thin-slice solutions that entrepreneurs have to navigate and piece together for themselves (e.g. Martech 5000, Stripe Atlas, etc.).

I also believe that changes in the workforce (lack of employer loyalty, the gig economy, and increased automation in the workplace) will make entrepreneurship an attractive and maybe necessary career alternative for many people. I want to take out as much of the friction of launching a successful company as possible. So we’re starting a new company called Startomatic. It’s a company to help anyone start a company. I think it will have all the elements I need to achieve the full intersection of my Ikigai. I’m very excited and will be sharing more about Startomatic soon!

If you are interested in updates on Startomatic, head over to our home page and sign-up.

(C) Robbie Allen. Reprinted with permission.