Kyle Swinsky of AMOpportunities

    We Spoke to Kyle Swinsky of AMOpportunities on Being an Effective Leader During Turbulent Times

    As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company,” we had the pleasure of interviewing Kyle Swinsky who founded AMOpportunities — a Chicago-based startup that helps healthcare students and schools globally obtain clinical training — alongside COO Benjamin Bradley in 2013 at their alma mater, University of Wisconsin.

    While at the university, Kyle launched an exchange program for international students as a premedical student. This grew into the university’s American Medical Student Association chapter that still exists today. After spearheading the largest medical student conference in the world in Washington D.C., and being elected to run a national exchange program, Kyle and Ben founded the business.

    Now at nearly 30 employees, AMOpportunities has upheld their mission of learning anywhere, training anywhere, and working anywhere, and has helped more than 3,000 international medical students and graduates obtain their clinical education. The company has raised $5.75 million in total funding. While Ben completed his JD/MBA at Northwestern University, Kyle completed his MBA at University of Chicago Booth School of Business. In 2017, the company won the University of Chicago’s New Venture Challenge and catalyzed the inflection point.

    To become a U.S. physician, medical students and graduates need U.S. clinical training in hospitals and clinics. This is the critically required, on-the-job component of learning how to actually practice medicine. However, there is a top bottleneck of our healthcare workforce shortage, given classrooms can fit unlimited students but hospitals are at a limit. With 27 percent of the U.S. physician workforce internationally trained, and an impending global healthcare shortage, there is a need for a company that solves the clinical education bottleneck, solving both access and supply. AMOpportunities is that solution.

    Thank you so much for joining us in this interview series. I know that you are a very busy person. Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you grew up?

    Born and raised in Wisconsin and thriving in Chicago. My passion is creating new models for obtaining social mobility, focusing on education and advocating for the global classroom. After going to college in Wisconsin, I moved to Chicago with AMO and then continued with an MBA from University of Chicago while growing the company. Education is life.

    What were your early inspirations that set you off on your particular journey?

    My story began when I snuck out of the children’s section in my elementary school to find Walt Disney autobiographies; three actually until I was reprimanded by the librarian. To build something that lasts you need to mobilize people and stick to a larger vision with persistency. I wanted to be a doctor but started a doctor’s club instead to help others. This led to mobilizing people further in healthcare, including a few conferences and then AMO.

    Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

    The best decisions come with balanced governance. My first attempt was when I gave myself executive control and my other founder financial control, where we had to agree on any financial decisions. While we agreed on percentages, I ended up having to knock on his dorm room door every time I wanted to get paid. Intent was great, but it caused unique situations that we tried to avoid in the first place. Eight years later, we are still best friends but takeaway is even the correct decisions are not good enough.

    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?

    I owe everything I have in this business to my cofounder, Benjamin Bradley. The above is just one example. People will see the outcomes and results, but hidden many times is the emotional mountain of building a business. Your co-ounder becomes your brother you argue with all the time but love. We have supported each other the entire journey.

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

    In the first chapter, the biggest challenge was the balancing of friendship and work. Our founding team would work all day and still spend time together after. In previous experiences, I had lost some friends when work became the only topic of conversation. We created a culture that balanced work and life where this never was an issue as we scaled.

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

    People. Luckily, my friends inspire me. And as we scaled, the more people we mobilized, the more inspiration I found.

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

    We are close to 30 employees with that same startup culture. Coming into 2020 as a travel business that brought students to hospitals proved difficult, but it was our people that drove us to an eventual revenue growth year after a dip. Resilience.

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

    Live anywhere, train anywhere, work anywhere is our mantra as we help thousands of students in over 100 countries obtain their career dreams. Most of our students come as their first trip to the United States. In 2019, we had a Chinese student group visit for their rotations. During their last week, we had a farewell event that featured a table tennis tournament in our boardroom with employees where we shared cultures and learned from each other.

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

    The mind is a muscle. Just like any other muscle it needs rest and will grow, but take care of it.

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

    We are just getting started. Our greatest success is continuing our mission to give students a better future that they choose. Over 3,000 healthcare students have joined AMO and used our training to become physicians, nurses, and more.

    Wonderful. Here is the main question of our discussion. 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.

    1. The more control you give up, the more you gain

    Creating a business requires you to wear every hat of the organization. The more you grow, the more difficult it becomes to hand off responsibility. Think about this early on because once you get past 10 employees, it gets even more difficult. Once you get to 25, you better have middle management planning. Our successful partnerships director, later in the AMO story, had an email inbox I created months before I hired him to begin a transition and meticulously planned so that I could hand off. It made all the difference to empower him.

    2. Every year you will rebuild the CEO position

    Each year you think you know what you are doing, but you have to stick to the overall goal and core assumptions rather than “what I have done correctly before” mentality. If you do not grow with your industry and product-market fit, you will lose.

    3. Balancing human and financial capital becomes all you think about.

    Once you succeed in mobilizing the people and get a product-market fit, everything is about allocation of resources. You raised two financing rounds conservatively and got the best people; it worked. Now you have to balance even more for the next growth chapter. Don’t ask yourself what to do, ask your leaders to decide “this is what we need to achieve, what do you need to get here” and listen to them.

    4. The mind is a more than a muscle.

    I said it before, but I must elaborate, because it is much more. When you hire the best people, they end up overworking because they care just as much as you do. All those late nights worrying about the company, your people have these too. In the “Musk” theory everyone tells you to work as much as you can without work/life balance, and this is just not true. The key is getting the most out of every minute, no distractions, focusing on the job at hand. And ensuring you rest the mind so that it can repeat and grow.

    5. Invest in communication skills more than you think.

    Some of my greatest highlights personally came when I sought coaching. Seeking professional speaking help, utilizing many of my professors, and joining accelerators to be better. The better you can effectively communicate, the better your people can achieve the goals you set for them.

    Now that you have gained this experience and knowledge, has it affected or changed your personal leadership philosophy and style? How have these changes affected your company?

    Yes. I am much more thoughtful about my decision-making and value people in new ways. My philosophy has definitely expanded, and the company has grown the more I grow.

    This series is called “5 Things I Wish Someone Told Me”. This has the implicit assumption that had you known something, you might have acted differently. But from your current vantage point, do you feel that knowing alone would have been enough, or do you feel that ultimately you can only learn from experience? I think that learning from mistakes is the best way, perhaps the only way, to truly absorb and integrate abstract information. What do you think about this idea? Can you explain?

    Most of my experience is from others. A favorite quote I was told in college was, “Experience is wealth, enjoy the journey,” and it is so true. Mistakes are so fun, the data points, and you can learn so much from others’ mistakes. I actively read articles and blogs to learn more why people think the way they do.

    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.

    Mobilizing people will be my life-long passion. I will never forget visiting Gandhi’s burial in New Delhi just hours after a young boy washed my shoes. There was an engraving that basically said think of the poorest person you can imagine, and if you are doing something to help that person, you are on the correct path. I want to keep doing that.

    How can our readers further follow your work online?

    I would encourage learning more about the company at

    You can also learn more about our company at the link here.