R.J. Talyor Joins High Alpha as Operating Partner

We sat down with R.J. to talk about his experience as a founder, his definition of and roadmap to product-market-fit, and the lessons he’s learned along the way.

Article by
Emma Ryan

Tech veteran and repeat founder R.J. Talyor has joined High Alpha as an Operating Partner. R.J. will specialize in helping High Alpha Studio companies achieve product-market fit.

As an English major turned product leader, R.J.’s path into tech was non-traditional, but his career is a great reflection of Indianapolis’ emergence as a MarTech capital. With early chapters at ExactTarget and Salesforce, R.J. is a startup veteran with over 20 years of product experience.

R.J. launched Pattern89 out of High Alpha Studio in June of 2017, scaling the company for four years before their acquisition in 2021 by Shutterstock (NYSE: SSTK). 

We sat down with R.J. to talk about his experience as a founder, his definition of and roadmap to product-market-fit, and the lessons he’s learned along the way. If you’re a founder or tech leader looking to find product-market fit, you won’t want to miss this interview.

What led you to entrepreneurship?

My grandfather was an entrepreneur, and I saw first-hand the combination of creativity and grit it took to be successful. I was drawn to that and looked up at him. That’s why I always knew I wanted to be an entrepreneur. But my journey to entrepreneurship didn’t truly start until I interviewed for the Orr Fellowship. 

The interviewers asked me where I envisioned myself in five years. I always said, "I want to own my own business," or "I want to be a professor," which was met with confusion because I was interviewing at large corporations. 

It wasn't until I met with Angie Hicks, who started Angie's list in 2002, that I was bold enough to share more about what I wanted to do, which at the time was to own a restaurant. And she said, "tell me about the restaurant," and that was the first moment that someone really heard and believed that I wanted to be an entrepreneur. 

Tell me about your experience starting Pattern89 out of High Alpha. What advantages did the studio model offer?

Starting Pattern89 was exhilarating (and often a little scary). I worried about making the wrong decisions. As an entrepreneur-in-residence, I could gather quick feedback from the High Alpha team around me — experts in marketing, design, brand, HR, and finance. In a startup, you don’t have unlimited time or resources, so quick access to subject matter experts makes decision-making easier and faster, accelerating the business. 

What lessons did you learn along the way that would be valuable to other startup founders and leaders?

At Pattern89, I learned the true power of a team. My Co-Founder, Jeff Cunning, was in lockstep daily strategizing and executing the vision. James Winans led our engineering efforts and was the driver of our winning culture. Allison Bantz led the scaling of our business as our COO. Samantha Wells, Bridget Johnston, Keenan Kadam…the list of leaders I could count on goes on. I will never forget the power of the OG Pattern89 team. 

How would you describe your experience going from 0 to product-market fit?  

As an entrepreneur, you're constantly swimming upstream, telling everyone about the change coming their way. In my case, the change was creativity powered by artificial intelligence. Along my journey at Pattern89, I met with brilliant marketers at top brands who initially didn't believe in the capabilities of AI and, quite frankly, didn't believe they needed it. Some of that feedback led me astray from what I knew; I knew that marketers needed a more innovative way to make creative decisions.

Getting to product-market fit is all about finding repeatability. It's asking the right questions, sorting the feedback, and discovering the order of features to meet what the market will pay for. And the definition of product-market fit is elusive, changing, and can be challenging to measure. But then you find it and scale!

After your successful exit, why join High Alpha as an Operating Partner?

Joining High Alpha as an Operating Partner allows me to work alongside startup founders and help them accelerate past the common mistakes to determine product-market fit. This role is a natural fit, given my background as a product leader, startup founder, and mentor. My main strengths are creativity, product marketing, and empathy, and I plan to use my experience to help founders in any way possible. 

Any learnings you would like to share that significantly impacted your journey?

My key learning is this  —  don’t imagine the future pain. Just begin, and be prepared to work really, really hard. 

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