Coffee Chats with Nina: Understanding the Entrepreneurial Mindset – Part IV

Part IV of an Ongoing Series – Heavily Caffeinated & Highly Enlightened

Two years! I truly can’t believe that I’m already approaching my two-year mark as a member of the Aequitas Partners team. It feels like it was just yesterday that I moved into my first closet-sized NYC apartment and received a phone call from Tim Gordon. He offered me an opportunity to join his team, that I now consider family. To some people, two years might not seem like a long time. However, upon reflection, I can confidently say that this has been the most transformative timespan for my own personal and professional development in my life.

My skilled colleagues, our innovative clients, and the thousands of impressive candidates I’ve interviewed have all contributed to my development in this field. But I must attribute an important part of my recent growth to the insights I’ve gained from the highly-driven healthcare technology entrepreneurs who have opened up to me during my Coffee Chats. Last year, I set out to better understand the entrepreneur’s mindset and hear stories straight from the source about what it takes to build a digital health business from the ground up – and that’s precisely what I got! I was gratified by these leaders’ willingness to participate in my Coffee Chats with Nina series and the level of genuine authenticity in their shared stories. I had the chance to dive into some pretty touchy subjects and they didn’t hold back one bit. I heard unfiltered accounts of their experiences including all the ups and downs; everything from the first moments when they knew they had novel concepts to the times they thought they were going to fail.

For this final article of 2019, I’m taking a look back at some of the key insights and highlights from my discussions over the course of this past year. I’ll also share some thoughts on what 2020 might have in store for this series.

Wrapping up 2019

Since we are all focused on this complex, highly regulated, and emotionally charged industry we know as “healthcare,” we’re also familiar with the challenges that confront us in attempting to innovate in this space. Instead of developing solutions for industries such as retail or consumer goods, the founders I met with all chose the convoluted world of healthcare technology. On top of the typical challenges facing all entrepreneurs such as fundraising and team building, these leaders have many added obstacles, spanning HIPAA regulations to longer than average sales cycles. In my first article of the series, “Taking the Leap,” I dove into what it took for these founders to actually take that first big step to build their respective companies in this trying industry. I was shocked to hear about how often they felt ill prepared to enter these life-changing journeys. Despite spending years working as venture capitalists or practicing clinicians, all of the executives shared the common sentiment that they had to do most of their learning on the job. While the path to growing their businesses has been difficult, these leaders all refused to accept the status quo and they continue to be driven by the notion that there must be a better way of doing things.

Since there is no all-encompassing playbook for the obstacles faced while growing a startup, I heard stories of some tremendous roadblocks that these founders have overcome. They told stories ranging from how they bounced back after hiring the wrong team member to how they were forced to completely change direction after losing an expected investor in a major funding round. I also heard firsthand accounts of times when founders were offered advice from people whose only intent was to get something in return and instances where there were challenges in working with relatives and close friends. In my second article, “5 Things Entrepreneurs Wish They Knew Before Building Their Companies,” I shared some of the biggest lessons they’ve learned as well as some pointers they wish they were given prior to starting their businesses.

My last article, “What They Don’t Teach You in Business School,” covered the different aspects of being an entrepreneur that you can’t train for ahead of time. While most of the executives I’ve spoken with have earned advanced degrees from the most highly regarded institutions, they all noted the aspects of being a founder that you can’t study. Many of them underscored the difficulties they encountered in assembling their teams. I heard stories about overcoming communication barriers, discovering the best ways to motivate employees, and making tough decisions around hiring and firing team members. I also had the opportunity to dig into another key topic I was curious about – time management. They offered insights on how they’ve attempted to manage competing priorities across their work and personal lives. Finally, I learned about the different resources (i.e., books, podcasts, networks) these professionals often leverage to become better leaders.

Looking at 2020

In speaking with such a wide variety of digital health entrepreneurs over the last year, I’ve heard many different perspectives on what it takes to build a business. I’ve spoken with both clinical and non-clinical executives. I also met with a number of first-time founders in addition to leaders who’ve had experience from previously growing other companies. Heading into 2020, I’m excited to have some more pointed conversations with this eclectic group of ambitious individuals while also adding new executives to the mix who will offer other fresh perspectives on entrepreneurship.

While I’ve had the chance to cover a number of interesting topics, I feel that there is a lot more to explore. Moving forward, I’m planning to tackle a host of new topics such as the challenges specifically facing female founders and the impact of major healthcare policy changes on these entrepreneurs’ business strategies. I’m also hoping to learn more about the dynamics of working with a co-founder versus going at it alone. Additionally, I’ve been increasingly curious about investors’ perspectives on many of these topics and would love the chance to connect with a variety of leaders in that space.

Moving into this next year, I welcome feedback from our readers on things you want to learn or questions you wish I had asked. Please send any thoughts directly to me at Looking forward to sharing more insights in 2020!