Why I left my 6-figure exec role to bootstrap a company

Why I made the decision to leave a comfortable job to start my own company.
Man thinking on rock in front of waterfall

I’ve quit two things in my life. Ironically, both situations were to focus on building a business. At 19 I quit my college basketball team to focus on a pedicab company I’d started. This year, at 26, I left a dream job at Untappd to start Beanie & Blazer, a lifestyle engineering company that trains people to become high performers.

For Christmas last year, my mom gave me a thumb drive full of old home videos. In my favorite clip, my first-grade teacher asks me what I want to be when I grow up. I reply, “I want to be an entrepreneur or a basketball player.” I may have abandoned the basketball dream, but there’s nothing stopping me from pursuing entrepreneurship.

7-year-old me prophesying my career (May 2001)
7-year-old me prophesying my career (May 2001)

My five years at Untappd were expansive. I started as an intern when I was 20, earned an opportunity to sell our first piece of B2B software shortly after my 21st birthday, and within three years had nearly 50 people on my sales team. I was promoted multiple times, saw a dramatic increase in compensation, received recognition for my work, and learned from some of the best entrepreneurs in North Carolina. There was still something missing. Despite the role looking perfect on paper, I succumbed to frequent bouts of frustration and burnout. This started a period of self-examination and reflection that led to my decision to leave the business.

Me and Untappd co-founder, Greg Avola at the Great American Beer Festival (Sep. 2018)
Me and Untappd co-founder, Greg Avola, at the Great American Beer Festival (Sep. 2018)

Burnout

Burnout is “a state of emotional, mental, and often physical exhaustion brought on by prolonged or repeated stress.” Most people conflate burnout with working too many hours, but this often isn’t the case. Some causes of burnout include:

  1. Heavy workload
  2. Lack of control over outcomes
  3. Imbalance of rewards for work performed 
  4. Lack of community
  5. Lack of fairness
  6. Misalignment of personal and professional values

At the onset of COVID-19, I spent time reflecting on why I felt burnt out at Untappd. The answers came quickly. My personal values were no longer in alignment with the company’s trajectory, I didn’t want to cede control over decisions or strategic direction, and I wanted ownership in something that’s mine.

Through this lens, I had an “oh, shit” moment that Untappd was no longer the best place for me to grow my career.

When you identify the cause of burnout, there are three steps to ease out of the slump:

  • Increase your stress tolerance – Focus on sleep, nutrition, exercise, and daily recovery. Oftentimes, people don’t hedge their stressful work life with a healthy recovery plan.
  • Identify and address your weak spots – Maybe you overwork yourself or don’t get the recognition you feel you deserve. People are more sensitive to some burnout triggers than others. Figure out your triggers and work to minimize their effect on you.
  • Change your daily responsibilities – Talk to your manager about what’s causing your burnout. If you’re a solid producer, they’ll typically try to help figure out a better path forward.
Burnout Defense Venn Diagram

Values

Imagine that twenty years from now someone writes a book about your life. The book can only be five chapters long, and each chapter represents a value that you’ve lived by. These values make up your self-identity.

Without self-identifying values, you’ll always be at the mercy of external forces that drive your behaviors. Much like a mountaineer without a compass, your life will lack direction and purpose until you align your actions with your core belief system. 

To decide whether Untappd would be the best place to spend the next five years of my career, I needed to create my own set of values. Here’s what I came up with:

  • Fitness of mind, body, and spirit – I focus on my personal well-being to stay healthy and grounded no matter how chaotic life becomes. 
  • Learning through coursework, reading, and conversations – I pursue education and development across a variety of personal curiosities. Psychology, philosophy, and business are some of my core interests.
  • Dynamic adventures – I regularly do things outside my comfort zone to challenge myself physically, mentally, spiritually, and intellectually.
  • Entrepreneurship – I own my outcomes both positively and negatively. I build teams and systems from scratch to accomplish goals.
  • Quality time with friends and family – I invest in my tribe with my time and energy.

Once I solidified these, I recognized that Untappd wasn’t able to grant me at least two of my core values. My life-long dream of starting a company would never be satiated. Although I was fortunate enough to play a key role in the company’s evolution, I didn’t actually start the business. The buck didn’t stop with me. I was on pace for more promotions and opportunities for upside, but there was always a feeling that I wanted more control over my day-to-day activities and the company’s overall strategy.

Additionally, I was no longer learning the skills pertinent for a start-up founder. Again, knowing this was my ultimate pursuit, developing the skills necessary for a company to grow from $15mil to $100mil in revenue are incredibly different from those required to get a company off the ground. A dissonance grew between the responsibilities I was taking on and how I wanted to apply my newfound skills. The leadership team at Untappd is incredibly talented, and I had a ton to keep learning from my peers and mentors. But mid-to-late stage business growth proved not to be within my personal value system at this point in time.

Control & Ownership

Maybe it’s an oldest child complex, maybe it’s bred from having divorced parents, but I have an insatiable need to constantly be in control of my decisions and outcomes. I love having the final say in decisions and full visibility into the impact these decisions have on the broader goals of the company.

As Untappd continued to grow and new leadership was introduced to the company, I realized that my influence would narrow to my domain of responsibility. I knew that would ultimately frustrate me as I grew further removed from parts of the business that I once directly or indirectly oversaw.

Leadership responsibilities as a startup scales

Compare this to the inherent ownership of a founder over his own company, and the decision becomes more obvious. Starting my own business would enable me to own my failures and successes with finality. No matter how badly I screw things up, knowing it’s my choice to execute in a particular way gives me a sense of freedom I wouldn’t experience under another person’s leadership.

Conclusion

I’ve had a lot of people ask me why I left. A Senior Vice President title and a significant compensation package seem like a 26-year-old’s dream role. It wasn’t until I began exploring the opportunity cost of my continued elevation at the company that I realized I was no longer in pursuit of my purpose.

Bootstrapping a company is a lonely endeavor. I have a ton to learn and will make many mistakes along the way, but I can rest assured that my successes and failures will be mine.

Living in accordance with my self-identifying values is incredibly liberating. It’s an exercise I encourage everyone to reflect on. Without a strong set of values, we’re merely plugging into our daily life and letting extrinsic forces determine our focus for the day. I want to exercise control over my experiences, and starting my own business is the best way I can do that.

There’s a lot of uncertainty for all of us – a second wave of COVID-19 is abreast, 2020 is an election year, and the world is undergoing a much-needed change in equality for under-recognized populations. In the midst of chaos, there’s nothing more empowering than taking account of all that you can control and controlling the hell out of it.


What is Beanie & Blazer?

Beanie & Blazer trains creators to differentiate themselves from competition by leveraging their unique values and talents. We call this process Lifestyle Engineering.

We can help you evolve with intent in just 6-weeks. Join the Mindset Accelerator waitlist to find out how.

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