As part of our interview series called “5 Things I Wish Someone Told Me Before I Became A Founder”, I had the pleasure of interviewing Alex Zekoff.

Alex Zekoff is the CEO and co-founder of Thoughtful, an automation-as-a-service platform whose mission is to enable all organizations to free their workforce of time-consuming processes. Thoughtful creates and manages automated digital workers that supercharge the operations of their customers across all major business functions including revenue cycle, finance, legal, HR, IT, and beyond. As CEO, his responsibilities include leading the revenue team, helping build a superior go-to-market and growth engine.

Alex started his career in technology consulting at a large multinational aerospace and defense company in 2009. He helped the company develop their enterprise resource planning (ERP) application and trained users to operate the software. Ten years later, he came back to that same company and helped build software bots (digital workers) to operate the ERPprogram. It was from this experience that he saw the full potential of enabling technologies like robotic process automation (RPA), cloud, optical character recognition (OCR), natural language processing (NLP) and artificial intelligence (AI).These insights led to the inception of Thoughtful.

Alex received his MBA in Entrepreneurship, Design Thinking from the University of California, Berkeley, Haas School of Business and his BS in Finance, Decision Science from Miami University (OH). Alex currently lives in Chicago and enjoys photography, traveling and DJing in his freetime.

Thank you so much for joining us in this interview series! Can you tell us a story about what brought you to this specific career path?

I now look back at my life and see it as a series of events leading up to the manifestation of me becoming a founder. It started as a young boy, learning from my father the grit and resilience needed to succeed in starting a business. (He started his own veterinary practice when he was 28.) After learning finance and statistics in undergrad, I learned software development, management and customer tact from my first corporate experience right out of undergrad. I then went on to grad school, where I studied tech entrepreneurship, venture capital and design thinking. That experience led me to dig into robotic process automation, which ultimately led me to the problem space that Thoughtful was founded in.

Can you tell us a story about the hard times that you faced when you first started your journey?

There have been many instances where I have identified as an imposter on my entrepreneurial journey. Specifically, when I was in grad school studying to be an entrepreneur, I felt like a fraud. I believed that my classmates were much smarter than me and had a higher likelihood of success. But 95% of being an entrepreneur is mindset. It’s how you view yourself and the world around you that enables you to achieve the impossible. Working through my imposter syndrome has been the largest achievement in my journey.

Where did you get the drive to continue even though things were so hard?

Motivation comes and goes, but discipline is the steadfast anchor of entrepreneurship. The hardest part for me was learning how to truly sell my product — to be all in with what I was selling. Early in your product development lifecycle, you don’t have much to sell, so you have to listen extremely well, set boundaries and be ready to hear NO a lot. Like 100+ times. The only way you get through those early days is through consistent execution and discipline.

So, how are things going today? How did grit and resilience lead to your eventual success?

We are very fortunate at Thoughtful to be in the position we are in. Not only do we have an amazing team of 30 U.S. employees and 25 full-time automation engineers who build on our platform, but we have amazing customers that have bought into the digital worker revolution. The first two years weren’t easy. We’re building incredibly complex technology at a fraction of the current market price and delivering exceptional value. Grit, resilience and dedication are just some of the ways that we have achieved so much in such little time.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

So many mistakes. Where to begin? My funniest — and, ultimately, most innovative — mistake was pricing our first digital worker (software bot) for customer №1. I cared so much about the sale that I priced it at $2,000 per month (what the customer was willing to pay) without any regard for cost or margin. After subsequently deploying it, our team realized it cost us around $5,000 per month to host and maintain the digital worker for our customer. Yikes!

It was because of this silly failure to look at the costs that we ended up having to figure out how to innovate on the technology side to support our business model. We ended up moving the digital worker to our own tech stack and reducing our ongoing costs significantly in the process.

What do you think makes your company stand out? Can you share a story?

Our mission is to build the world’s largest digital workforce and free up time for people around the world to pursue more meaningful, higher-value work. We are organized around this singular focus, and you can see this drive in the way our employees show up everyday to help realize this mission. We are building a culture of mission-driven warriors that understand that freeing up time for the global workforce will help solve existential human challenges like food production, climate change and safe drinking water.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Think in longer timeframes and understand that gratification will be delayed if you pursue this career path. Instead of 2–3 years to realize your vision, think 15–20 years. That longer time horizon will lead to more rational thinking around the near-term goals needed to achieve the overall mission.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My parents have been a relentless supporter of me my entire life. They have shown what unconditional love and commitment to excellence looks like. When I was growing up, my father pushed me to be the best version of myself. If I brought home a 96 on my math test, he would help me figure out why I missed the perfect score and where I could improve. That relentless pursuit of finding the truth and achieving mastery has served me well my whole life.

How have you used your success to bring goodness to the world?

We are givers is one of the key values at Thoughtful. We aim to bring more jobs to Python developers across the globe to help support our mission. We believe it’s not necessary to take on student loan debt to have a meaningful, fulfilling career. With that, we aim to develop more jobs for the modern economy using our platform.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

Be all in. Starting a company is extremely difficult. Before I made the decision to start Thoughtful, I had tried to start companies in the past with no success. One of the limiting factors was that I had a backup option. I knew I could always go back to my cushy job in management consulting. It wasn’t until I put my entire self and finances into a singular focus that I was able to achieve success.

Don’t be afraid to ask for help. Starting a company is an exercise of asking for a lot of help from trusted advisors, investors and employees. In my 20s, I had too much ego to ask for help. I thought I could solve all my problems on my own. It wasn’t until I went to graduate school that I figured out that leveraging your network was a key accelerator in life.

Trust your gut. Data is important, but intuition is more powerful. I have learned over decades now to trust my gut feeling and to use that feeling to be more skeptical in certain areas where I was overly optimistic, and vice versa.

Be direct. Startups are default dead by nature. There isn’t time to be indirect or wait and see. Every time there is a conflict at Thoughtful, I go straight to the source to understand the root cause. Instead of weeks, it takes hours or days to resolve issues.

Have integrity. Life is a series of completing and committing to an endless list of tasks. When people know they can count on me to complete something when I say I am going to do it, it creates a culture of trust and performance.

Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder”?

In the end we always have balance. Equilibrium. With a slow and steady uptick. Even if you look at the stock markets, there are ups and downs with a slow inevitable up. Keep your eyes on the emotions. Notice when it’s time to re-center. If it’s too high, it’s time to recalibrate. Additionally, it’s important to have a trusted council of healers (I do Reiki!), coaches and advisors around you when the stress becomes overwhelming. For example, my fiancee, Ashley, is my mindset coach. She helps me uncover my blind spots and motivates me to dig into the root cause of my issue.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

The anti-consumption movement. We have built civilization on the idea that more is better. This accelerates progress but with negative externalities (i.e. energy usage, pollution, waste). If we dial back consumption and focus on gratitude for what we have versus what we lack, I believe there is true transcendence in that space.

How can our readers further follow your work online?

We’re posting a ton of new content about automation and the future of work at Thoughtful+, our free-to-subscribe content area. Check out Thoughtful to learn more.

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This was very inspiring. Thank you so much for joining us!