R.J. Talyor is a tech leader. He has founded and exited a number of companies. R.J. got his bachelors and masters degrees in English and Creative Writing from DePauw and Purdue Universities. At one point in time he dreamed of being an English professor and owner of a sandwich shop. Yet, like many of us, he is doing something different.
Today, R.J is CEO and Co-Founder of Backstroke a generative email platform for marketers. He founded the company with his wife and a few others. At Backstroke, they are focused on using artificial intelligence to make 1-1 connections with email at scale.
Prior to founding Backstroke, R.J. worked for and founded a number of technology companies including ExactTarget (sold to Salesforce), Pattern 89 (sold to Shutterstock), and High Alpha, a Venture Studio in Indianapolis, IN. Each of these experiences, being a dad, and coaching sports has helped mold R.J. as a leader and career explorer.
Listen to the full episode. You’re sure to pick up a nugget or three for your own career adventures.
Don’t have time on your commute to work? Skim the top themes below. Then listen to the full episode on your commute home.
6 Core Themes
Here are six themes you should take note of in your own career adventures.
Prepare for Next While Delivering Now
Always be a step ahead. Yes, we all must be present in what’s happening today. Nonetheless, we benefit by planning for the future. This doesn’t have to be all encompassing and a distraction.
After R.J. sold Pattern 89, he and his co-founder created a shared Google Doc called “Next Time.” This became their idea repository, their place to get ideas out of their head and start to make them real. One simple way to do this is to carry a idea journal. How might you take your ideas that are half baked and put them on paper. This is always the first step.
“After we sold pattern 89, which is my first startup, I was like, what can I do next time? And my co founder and I started a shared google doc called “Next Time.” We just started putting notes - we're going to do this, we're going to do that, we're going to do this. I knew I was going to do something else. The second thing I knew from my pattern 89 days is that what made us different than everybody else was we had a giant data set. We had over 7,000 brands connected into our data set. That was the big difference. It wasn't like a fully formed idea”
Slow Burn Then Leap
We’ve all seen the movie before. The hero is at work, frustrated. Their boss sucks. Then, they finally snap and quit. They jump into the new career pool, struggle a ton, and emerge successfully on the other side. Remember, this is the movie, not real life.
Real life is filled with risks and bills. Yes, we all eventually must fully immerse ourselves into what’s new. R.J. shared how he and his wife slowly moved toward the next leap. They made small investments over time to build a data set for their next venture. Then, they leapt into it when they reached a financial crossroads. Eventually you gotta submerge, but don’t believe that you must go all-in immediately.
“At the end of 2023, my wife and I co founded this business, we had this giant data set. We had two years of data and we looked at each other and the cost to maintain the acquisition and storage and then also the services we were using started being a real cost in our monthly budget. And we're like, okay, so we either need to do something with this or to get some customers to buy it, or we need to stop doing this because we can put that money towards the car payment…It's a slow burn until you look at the bills and then make the decision to literally jump in.”
Last Day on Earth
Would you be pissed off at yourself if you knew you spent your last day in that way? This question can help you create a catalyst to do something different. Oftentimes it takes a birthday, death, or some disorienting moment to catalyze change. What if you asked yourself this question from time to time?
It could encourage you to take a small step down a new path. Maybe you are curious about moving into a new field. Ask yourself this question. Then identify a small step like reaching out to someone in your network to learn about their line of work. It could make all the difference.
“I've made a number of big decisions in my life by thinking literally, is this my last day on earth? It's a little cheesy, but go with me…I could die in a car accident or some sort of freak thing. There's all sorts of weird things there. And I think, “Would I be angry, when I'm dead, that I spent my last day on earth doing that thing…”
Tradeoffs Help Prioritize
Life is filled with tradeoffs. We all must choose what is most important. When I was at P&G, an executive named Jim Lafferty did a presentation about only being able to prioritize five roles in life. You only have enough to fit on your hand. Being a father, spouse, and prioritizing family / friends takes up three spots. Work likely takes up one more. You likely only have time for one thing if you are a spouse or parent.
R.J. recognizes this too. Thus, he has prioritized coaching soccer. He can’t do some of the things he used to enjoy. That’s life. We all have dozens of interests. We must make choices throughout the seasons of life to lean into the highest priorities.
“I love coaching soccer. That means that at five o'clock, I'm gone. There are tradeoffs…It's a matter of just piecing it all together and choosing how you want to spend your life. I don't golf, I don't run marathons anymore. My friends, I see on the sidelines of soccer, who are the moms and dads who are also coaching soccer.”
Build Tough Skin
Giving up is easy. Iterating and trying again and again is the hard road. Sure, we should rethink objectives if we are spending time on something we don’t enjoy or isn’t a core responsibility. However, shouldn’t we keep going if we are traveling a career path we enjoy and simply are faced with an obstacle?
R.J. talks about how we become less willing to try and iterate as adults. We tend to ease back into what we know. Sure, we should embrace our strengths. Yet, we can lean into our current strengths to build new ones. This is all about embracing a growth mindset.
“You have to keep trying and iterate, being an adult is we lose the tolerance for that iteration. We just want to be the expert at something. Humans are designed to avoid discomfort. In startup land it's just all discomfort. It's all about saying, “Hey, here's this idea that I had. Here's where you would click on this product. What do you think? And then having people either say, “I love this. Yes, I see your vision,” or “I don't understand this.”
No Job Description
We should ASPIRE to not have a job description. HR and Legal experts might say, “Absolutely not! We need order! How will we set expectations and track performance?!” That’s why I said ASPIRE. Of course we need a general framework for our career roles.
20 years ago, my career coach told me that the best case scenario is to find a job opportunity without a job description. Scenarios like these help you grab the bull by its horns and create what you want. It allows you to build in your interests and skills. R.J. had this opportunity with one of his first jobs. He trusted his network and embraced the unknown. It lead him into the tech realm.
“I applied for a role called a deliverability consultant, which I didn't know what that meant. They did not have a job description. I really, I didn't know what it was or, and then they said, we don't have job description. I said, I don't even know what this means. Then the co founder Peter McCormick called me and he liked me for some reason, and he like, he was like, you got to take this job”
Listen to the Full Story
R.J. is focused on combing his love of language with technology and business at Backstroke. This has come from exploring new paths and being open to undefined roles and ideas. He knows there are tradeoffs and is focused on what matters most both personally and professionally.
Enjoy the episode! Thanks for you support!
Paul G. Fisher
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