Founder Stories: RJ Talyor of Backstroke

RJ Talyor always knew he wanted to be an entrepreneur.

Well, sort of.

He remembers telling people that he wanted to be two things, “I want to be an English professor and I want to own a business.”

The tension between solo, creative and philosophical crafts and customer obsession, actually show up in many aspects of RJ’s life. From his early ExactTarget days to launching Pattern89 and now Backstroke, Talyor’s journey reveals a founder who’s never been afraid of the messy middle. 

Even if it took him a while to step into the role.

“I didn't ever start a business, well I taught swim lessons, which is my own ‘little entrepreneur’” he says, laughing. “I was a lifeguard when I was 14… and I would work for five hours a day teaching swim lessons, teaching eight-year-olds how to do freestyle”.

It wasn’t a tech company, but in our eyes it’s definitely entrepreneurship.

It was also apparent to others in the young Talyor’s life that he had found his calling.

“My dad worked for the same company for 53 years,” Talyor says. “He worked hard, sent us four kids to college. But he always said: ‘RJ, you should be an entrepreneur.’ And I wanted to be an entrepreneur. I had my own kids at the time and thought, what am I going to tell them? They should pursue their passion.” 

That was the tipping point. RJ left his job and finally built ‘the thing’.

A Restaurant Called Roy Jacks (And Other Early Dreams)

Before any of this came to fruition, RJ dreamed of opening a sandwich shop.

“I wanted to own a restaurant called Roy Jacks, which is my name, Roy Jack. I think it sounds like a sandwich shop,” he laughs. “A hole-in-the-wall sandwich shop that serves great sandwiches… I get to serve people. I get to make great food.”

That original instinct - local, warm, built around knowing your customers - is still at the core of how RJ thinks about software. But it would take a few detours through corporate life before RJ would commit to building something of his own.

From Corporate Misfit to ExactTarget MVP

RJ started his career the way many do - wearing suits he didn’t want to wear in jobs where he didn’t necessarily know how he fit into the whole.

“I felt like I was playing dress up,” he says of his first corporate job. “I thought I was supposed to act in a certain way or something”.

Things changed when he joined ExactTarget, the digital marketing platform co-founded by Scott Dorsey, now Managing Partner of High Alpha where Talyor also worked as Operating Partner. “It was so emergent… it was like the wild west,” he says. “I started first as a deliverability consultant. I didn’t even know what that meant”.

He figured it out. And then some.

In six years, he became ExactTarget’s go-to mobile expert, writing parts of books, joining the board of the Mobile Marketing Association, and presenting to CMOs across the globe - all before the age of 30.

“I read all the legislation… I wrote a book about deliverability… I was consulting with CMOs… when I was 25”.

That feeling of being in the wild west seemed to change when Salesforce acquired ExactTarget. “They were great to me, [but] I learned that entrepreneurship and growing a business at all costs is very different to scaling a global machine. They were the first people who came literally and said, ‘Here’s your job description,’” he remembers.

For someone who thrived in ambiguity, it was just… different.

“I get bored. I’m frustrated because there are problems that I’m not allowed to solve”.

So he left Salesforce, but stayed in Indiana.

Staying Put

Partially because of the globetrotting evangelism of being a mobile expert, the conferences and consulting for clients, RJ always thought he’d leave the state. And he did try. Kinda.

“I always thought I’d leave. I did a six-month internship in London, in college for Ernst & Young… When I graduated, I tried to get a job in London.” 

What kept him in Indiana wasn’t just circumstance - it was momentum. He joined the Orr Fellowship, a program designed to fight Indiana’s brain drain. He met his wife. They had kids. And by the time he realized he’d stayed, he also realized he was glad.

“I love having a yard. I love knowing people,” he says. “Building a startup is really, really hard… and knowing people in the city who I can call for a coffee or a pep talk… is really, really valuable”.

Over time, he saw the state around him change too.

“Indiana saw some big successes… ExactTarget being acquired… Angie's List… and that flooded the market with money that entrepreneurs then wanted to invest in other entrepreneurs”.

The state doubled down. Initiatives like TechPoint and Elevate Ventures added infrastructure and capital.

“I know some people in bordering states who have literally moved their headquarters over the border to be in Indiana because it benefits them to do it,” he says.

Building Pattern89 (Before AI Was Cool)

After Salesforce, RJ took one more ‘traditional’ job - VP of Product at Geofeedia - before realizing that if he didn’t start something himself now, he never would.

“I made a few decisions in my life based on the same methodology,” he explains. “If I died today… would I be pissed that I didn’t pursue X?”

So he built Pattern89.

The idea was simple: marketers want to run experiments - but never have time. So what if software could experiment for you?

With early backing from High Alpha, Pattern89 launched in 2016 as a tool that used machine learning to predict ad creative performance on platforms like Instagram and Facebook.

“We figured out that we actually didn’t have to experiment - we could predict what the outcome would be with enough data,” RJ says. “We would really help marketers with saving money… because we could predict what ads would work”.

In 2021, Shutterstock acquired Pattern89 to power Shutterstock AI. RJ stayed for a year - then left again.

If you’re reading this story, you can guess why.

Backstroke: Bringing Email Into the Future

Launched in mid-2023, Backstroke is RJ’s latest business. It’s where all of his experience comes together: email infrastructure from ExactTarget, creative performance from Pattern89, and the now-mature power of generative AI.

“We generate email campaigns that perform,” he says plainly.

Backstroke plugs into an e-commerce brand’s existing ESP (like Klaviyo or Attentive) and creates content variants tailored to each user’s behavior, geography, and engagement history.

“So if you’re living in Michigan, you might get an email that has a blue shirt in it and headphones… with a subject line that is four words and has two emojis,” he explains.

[ED: Or it could be a green shirt, we are quick to point out, to our interview subject.]

Meanwhile, someone else on the same list - maybe a parent in Indiana - gets an entirely different subject line, image, and CTA button.

It’s hyper-personalized performance marketing at scale, powered by a deep understanding of what actually works. Investors seem to agree, with Allos Ventures leading a $2.8m round in which High Alpha and Ground Game Ventures also participated. It’s the second fundraise for the business in just over a year, with the same group of investors participating in a $2m round in June, 2024.

This is further indication that email is - once again - having a moment, especially for anyone whose sales are predominantly online. 

“Email makes between 20 and 50% of the revenue for ecom brands,” RJ points out. “So if we can help marketers get that lift… that’s huge”.

A Professor of Product (Without the Lectures)

Talyor never did become an English professor. But he says he still thinks like one.

“Creative writing is all about iteration - and entrepreneurship is the same,” he says. “You’re staring at a blank screen… trying to figure out what to do. And then you put it out there and someone tells you it sucks. And you have to decide: do I believe them?”

That instinct - refine, release, reflect, repeat - has guided him from swim lessons to startup exits.

And now, with Backstroke growing fast and a team of eight winning over ecommerce brands one dinner and user event at a time, RJ isn’t chasing Silicon Valley’s approval.

“I used to feel like… I live in Indianapolis, but I’ve traveled, right?” he says. “Now, I’m like, you live there. That’s great. I love coming to visit you. But I live here”.

And he’s building here, too.

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