Jonathan’s Winding Path

I met Jonathan Engle five years ago through a fellowship where I was serving as a Coach-in-Residence. At that time, I was immediately struck by the breadth of intellectual pursuits he engaged. I’ve watched from afar his dedication to the Salt Lake City startup scene and his recent joining of the Utah Army National Guard. Jonathan, 27, is the co-founder of mystartupstack.com a marketplace for service and deals for startup founders.  

In two-three sentences how would you describe what you do most days/weeks?

I’m working full-time on the Startup Stack, often switching between sales calls, and building our systems and processes. Throughout the day, I take breaks by doting on my wife and cuddling with our 2-month-old. When I’m not working, I enjoy catching up with friends and family and practicing Capoeira, a Brazilian martial art. I’m also a bit of a nerd and enjoy a show or video game when I can - I’m finally watching “Game of Thrones” (just finished season 5) and am playing “Red Dead Redemption 2.”

What did you want to be when you were eight?

When I was eight, I wanted to move to Australia and work at the Australia Zoo with the Crocodile Hunter. I knew that living far from home would be hard for my parents, but the Crocodile Hunter taught me so much and was just such a nice guy. I liked how watching his show made me feel.

What did you learn about work that you learned from your family? 

We didn't talk about work much growing up since my parents were pretty hands off. My dad had a very simple career - he worked at the same University he got his bachelor’s from until he retired. As I entered the workforce, I carried my own expectations, but I've been pleasantly surprised that all my parents care about is that I enjoy what I do. They never talk about the money much. I guess I learned from them that I want my work to be something meaningful and worthwhile.

What professional experiences/employers had the greatest impact on you?

Be Deliberate and a Professional

University Impact taught me about being deliberate and a professional. Our leader Dan Blake was an amazing person to work with. Every interaction was a rich learning opportunity. He thinks through things deliberately and involves you in the process. This gives everyone a voice. He’s a successful operator in businesses with a talent for teaching what he does well. That trickled into the rest of the work environment, so I learned immensely from my peers. In hindsight, it’s a work environment I’ve never seen replicated and I left that job too early!

Entrepreneurial Bias

Beyond traditional working environments, I’ve always had an entrepreneurial bias. The Startup Stack is my fifth time starting a business (exempting numerous childhood lemonade stands with limited success). Other businesses include working in real estate as an agent and as an investor, a bike rental business, revenue operations consulting, and now a startup perks marketplace. Every other job I’ve had was always entrepreneurial, such as running a business franchise in Paraguay or being the first sales representative at another software startup. These experiences taught me to set my own schedule, navigate ambiguity, create a strategy, make a plan, iterate based on lessons learned, and frankly, care for and strengthen my mental health.

What is something about your career journey that people might not expect?

From Investing to Janitor

I quit my job at  University Impact so that I could have time to date my now wife who had a busy schedule finishing up her dance degree. So, I took an early morning shift as a custodian. At the time, I told myself and others that I was quitting that job because it was time for me to start my career as a real estate agent. I already tried real estate once before, but I thought that I had finally learned enough to make it happen. But it was really for the relationship. Freeing myself up was worthwhile for us and for myself mentally. I’d like to think we would have still worked out without that sacrifice, but maybe the relationship wouldn’t have progressed without that availability.

Work in Paraguay without Speaking Spanish

Another unexpected aspect of my career journey is that I didn't speak Spanish when I moved to work in Paraguay. I learned when I arrived. To be fair, I already spoke Portuguese fluently and took Spanish in high school, but that was far from enough. My first day in Paraguay was an entrepreneurial initiation. I was given a ball of clay and had all day to trade it, and make as much money as I could. With a handful of words, a terrible accent, and a lot of sweat, I made the equivalent of $50USD. I was short of my $80 for the day, but it was yet another step in my entrepreneurial training. That was just the warmup for many long, hot days selling people cookies on buses (all part of their entrepreneurship training program).

Why did you pivot?

In 2020 I was the first salesperson for a new software startup. It felt like a dream come true at the start. But I soon found that there was no product-market fit. Covid tanked our go-to-market strategy too. I made over 6,000 cold calls to no avail.

I felt a deep lack of meaning in life after a year of working from home selling a software that no one wanted. I still had an entrepreneurial itch, but I was temporarily burnt out on those dreams of building something special.

At the same time, there were a lot of wildfires in Utah. I really wanted to help in my community, and a friend of mine brought up the Army National Guard casually on a phone call. By the end of that conversation, we both committed each other to message a recruiter and learn more. He didn't join, but I swore the oath and joined the Utah Army National Guard. I chose a job that required nearly two years of training. I wanted what I called my "military sabbatical" to get away from Utah, figure out what I wanted, who I want to be, and come back with a fresh take on life.

It worked! Despite how much the Army can suck, I love it and enjoyed most of my training. I made amazing friendships and got a break from what feels like Utah’s monoculture. Since returning home in December 2022, I’ve enjoyed a renewed sense of meaning in life, found my entrepreneurial stride again, and am enjoying broadening and deepening my relationships. I’m glad I listened to my craving for change and had the courage to do something people would call crazy.

What skills were portable from what you had been doing previously and what was brand new to you? 

Obviously, the Army culture was brand new to me. Basic Training introduces you to the Army culture, customs and courtesies, and the other realities of a U.S. soldier. I was not waking up early before I joined (was definitely, mildly depressed at the end of my last job), so I surprised myself with how quickly I picked up the schedule of waking up early and being active all day. I remember as a kid seeing BYU ROTC soldiers in my hometown running around before 5am while begrudgingly waking up early to go to a campout. I never fathomed that I would one day do the same thing. Now I wake up at 5 a.m. pretty naturally (although a newborn at home has thrown my early rising for a loop).

By far the most important skills I brought into joining the Army was perspective and emotional intelligence. I lived in Brazil for almost two years and in Paraguay for seven months. Both of those were very hard things at the time, but the hardships eventually ended, and I grew from them. That perspective helped me on particularly hard days. My emotional intelligence helped me to connect with my fellow Americans from all different walks of life. I met all kinds of people with backgrounds unlike anyone I'd ever known. Thankfully I was able to make friends with lots of different people. The challenges of military life really bond you to those around you in a special way.

What was the hardest part about making a career pivot?

Joining the Utah Army National Guard was probably the toughest career pivot. I’ve done a lot of non-linear career moves, but I have a family now with more responsibilities. Also, lots of big life changes too frequently is exhausting. Joining the Army at any point in time is not easy. When I joined, I was living the typical Utah career dream of working in tech. Yet I wasn’t happy with my first job in the tech space. I was frustrated with how my leadership handled some situations. What better work environment to transition into than the stereotypical military leadership environment, right?

Most people I spoke to who had never been in the Army told me what a terrible idea it was. Everyone who had served in the Army thought it was a great idea. Disregarding the advice from my existing community to opt into a new community took courage. There was something about this new community that spoke to me.

The time away from a typical civilian career grind gave me clarity. I know better what I value and am more confident to make decisions for myself. Frankly, the military community is awesome! Everyone is down to earth and really accepting of who you are.

What were the most important lessons you’ve picked up along the way?  

No Destination

There’s no point of arrival! It’s a made up and probably somewhat western idea. As I’ve allowed more non-dualistic thinking into my life, it’s brought me great peace. The reality is there is no career arrival point. By tuning into the present, I can recognize what I want more and less of from my career presently. Oftentimes, those needs can be met by working with my current work, but sometimes it can mean changing gears and trying something different. I don’t regret trying new things in my career (except debt is expensive - I could have learned those lessons much cheaper). Exploratory experiences are totally worth it.

You Have Time

I remember hearing in some cheesy, motivational YouTube video recently that you should try everything in your 20s, get really good at something in your 30s, get paid for it in your 40s, and do what you love in your 50s. That’s not a perfect life formula, but it has a good sentiment. It’s about 20 years slower than I thought I was supposed to live.

Always be Networking.

Always get to know people, listen to them authentically, and try to keep in touch. Sometimes it’s overwhelming to keep in touch when we meet so many people, but there are people who anchor us within each chapter of our lives. Those relationships reappear in unexpected ways even if we don’t keep in touch. And frankly, it’s helped me to feel like part of a community and less prone to loneliness and isolation.

Shape Your Narrative

Don't let the last thing you did define you. It's your story. Tell the story that fits your next move. Most career moves make sense to us when we make them. But on paper that weird journey doesn't make sense to other people. That's okay.

What would you say to others who are doubting their ability to make a change in their career/vocation?

You only have to say yes when the offer is on the table. Until then it's all just an idea in your head. Pursue things until the point of commitment. By then you’ll likely know if it’s the right decision. Listen to that inner intuition and you’ll know what to do when the time comes. For example, let’s say I read a job posting that I’m really excited about. There’s absolutely no risk in applying for that job and seeing how far it goes. I can interview all the way to getting an offer. Until I get the offer, it’s a fantasy in my head. That helps me a lot with career decisions and helps me filter fiction from reality when making decisions.

Where did you get the confidence and support to make such a change? 

Doing things I wanted to do, rather than following cliche advice like optimizing for traditional, stable career paths. Pursuing my own path at different times in the past really paid off. For example, moving to work in Paraguay was pretty wild. I got to know the CEO of the company during one of my college courses and loved what they were doing. I asked to walk with him to his car at the end of our last interaction. By the end of that walk, he offered me a fellowship at his business. Little moments of serendipity give me hope that no matter what, a path will open up when we’re ready for it.

What is something about your career journey that people might not expect?

Emergent decision making - it's all been fairly unexpected. I don’t have some master plan that I’m following. Sometimes I wish I had a more deliberate vision of the future. I had that when I first started my career and had no idea what I was doing. I repeated trite goals like, “I’ll make a million dollars by the time I’m 30” and whatnot. I’m humbled by every new experience that I have which makes me more open minded about the future. My key is managing expectations with myself and my wife - we make a great team through it all.

What, if anything, are you hoping happens next in your professional life?

I recently moved to full-time on the Startup Stack as our new ceo and am really driven to support startup founders. We currently support almost 90,000 startup founders, but I think we’re just getting started, so this is yet another big change and a proverbial leap of faith. It was intimidating to leave a full-time job having just had our first baby, but I believe the lessons are compounding into what will be a great experience. The first two months full-time have been extraordinary, both in terms of personal satisfaction and tons of support rallying around our mission of supporting founders.

Besides that, I think there are big opportunities for community building in Utah and hope to play a role there. I’ve served on a nonprofit board in the past and hope to do so again.

What social media links, if any, might you like to share in the piece?

LinkedIn - https://www.linkedin.com/in/jonathancengle/