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

Part III of an Ongoing Series- What They Don’t Teach You in Business School (or startup summer camp)

We often applaud successful entrepreneurs for creating innovative solutions that are aimed at changing the status quo. Our culture prioritizes entrepreneurship skills so much that we now offer summer camps such as Biznovator and school programs like We Grow to empower young entrepreneurs. Where were these amazing programs when I was stuck sweating in the summer heat at tennis camp? By the time I attended university, my school offered a brand new minor that I was excited to partake in called “Entrepreneurship & Management.” We analyzed corporate case studies, developed business plans, and built mock marketing agencies.

I generally agree with the idea that it is important to instill entrepreneurial skills such as creative thinking and teamwork in children and young adults. However, I have also come to understand through my continued Coffee Chats with Founders and CEOs in the digital health space that there is a lot about entrepreneurship that we can’t learn in summer camp, college, or even business school. Below I’ve pared down my findings into three categories: honing people skills, balancing competing priorities, and leveraging available resources.

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The “People Stuff”

Over the course of a business school education, you might dive into classes focused on finance, organizational behavior, management, or accounting. However, one entrepreneur who earned her MBA from one of the most prestigious business schools in the country noted that while her education was incredibly valuable, it didn’t exactly prepare her for all of the “people stuff” that came along with building her business. For example, she found herself embarking on new and exciting quests to better engage her employees and establish a strong company culture. This was what she called “the fun part” of learning on the job. She was also confronted with much more difficult predicaments regarding underperforming hires. No book or course had prepared her to determine when is the right time to let someone go or even how to fire an underperforming employee. She said that as a founder, “it’s important to gain more comfort in living in the grey area, rather
than in a world that is just black or white,” especially when working with and making decisions about your team members.

Another founder spoke about her successes and challenges while bringing together a group of employees with a variety of skillsets and work experiences. She knew early on that there was a great benefit in assembling a team that would offer a diverse set of perspectives. While she was proud of her success in hiring an eclectic team, spanning clinical researchers to software engineers, she was quickly confronted with a significant communication barrier. Since her team members came to the table with different specialized skillsets, they became frustrated when trying to speak and understand one another’s views and ideas. Her background as an investor never fully prepared her for this type of challenge. She found herself acting as a translator between a physician with 5+ years of clinical care experience and a product expert who had never worked in healthcare before. Once she made a more concerted effort to level the playing field by creating a company culture that invites people to ask questions and never assume that any concept should be immediately understood, her team began working well together.

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The Balancing Act

As a millennial living in NYC, I often find myself struggling to strike a balance between my career responsibilities, social activities, and self care needs. If I find balancing these priorities difficult, I was curious to know how founders and CEOs, who have more at stake, attempt to balance their work and personal lives. When I asked these entrepreneurs how they maintain balance, I often received a laugh and the response: “I don’t.” My Coffee Chats have taught me that the idea of a true work-life balance is unattainable for someone who is building a business from scratch. While striking a perfect equilibrium of work, self, and family needs is unlikely, I’ve learned about a number of tactics that these founders have employed in an effort to distribute their time in a way that leaves them feeling fulfilled.

I spoke with a second-time entrepreneur who shared that work truly was his number one priority while immersed in his first entrepreneurial venture. During the time that he built this first business, he also became engaged and got married. He found it difficult to create a separation between work and home life, as he was constantly thinking about the needs of his company. Since then, he and his wife have had children and he has further recognized the need to strive for more work-life balance in his new role as CEO of a different startup. For him, the key was to hire an energetic Chief of Staff with the bandwidth to juggle multiple projects and the ability to take things off the CEO’s plate. With this incredible new hire offering a safety net for any immediate work-related tasks, the CEO is now able to go home at 5pm and spend more quality time with his wife and children.

I’ve also learned about the concept of career-life integration rather than attempting to compartmentalize different aspects of work and home life. I spoke with another Founder, who in addition to her work responsibilities has two young children and two parents in need of care. She said that she is not striving for perfection in any one area, but instead thinks of ways that she can integrate her work and home worlds. For example, working in a startup gives her the flexibility to take her children to school in the morning and to be home with her family at dinner, although she will often sign back online in the evening to answer emails once everyone is asleep. Since her company has grown, she reminisces about the times she was able to get more hands on and involved in the smaller tasks associated with building the business. However, she has investors who say to her, “you can’t do it all, you really need to hire others who can help you.” By making the decision to shift many of her previous responsibilities to her capable employees, she is able to find more time for other aspects of her life.

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The Resources Available

Making time for continued industry learning and professional development is difficult, especially when you are a Founder who can barely find a minute to eat lunch. A number of entrepreneurs voiced their tendencies, for better or for worse, to hunker down, trying to get everything done. However, they often forget to pick their heads up throughout the day to leverage the resources available to them- whether in the form of consumable materials like journals and podcasts, or in the form of people such as mentors and advisors.

One CEO mentioned that he started using a time tracking device to compare how he would like to be spending his time with an accurate assessment of how he is realistically spending his time. He discovered that he wasn’t dedicating as much attention to networking, mentoring relationships, and industry reading as he would have liked. He now has an hour carved out on his calendar every day to read the news, blogs, journals, and other relevant publications.

A first-time founder described how he immediately immersed himself in all the resources he could find online about starting a company and raising funding. He said that First Round has ggregated an incredible variety of resources for founders. Additionally, he mentioned how he was inspired by Nike Co-Founder Phil Knight’s book Shoe Dog and he spoke about the lessons he learned from the book The Hard Thing About Hard Things by Ben Horowitz. Other great resources that entrepreneurs shared included a number of different podcasts, such as How I Built This with Guy Raz, Masters of Scale by Reid Hoffman, and Reboot with Jerry Colonna.

In regards to human resources, many Founders have found wonderful communities where they can share ideas and personal stories with others who can relate. Some leaders I spoke with took advantage of networks built by unique co-working spaces like The Wing, while other leaders have joined what are effectively “business leader support groups” offered by companies like Venwise. I’ve also heard from some entrepreneurs that they enjoy seeking guidance from people in their existing network that comes in the form of family, friends, and friends-of-friends who can relate to starting their own businesses.

These coffee chats have deepened my respect for entrepreneurs and what they are juggling on a daily (or minute-by-minute) basis. They are constantly pulling different levers, continuously learning how to better manage their teams while making time for their personal and home lives, as well as their own professional development. This has also brought to light the psychological impact that many entrepreneurs feel when attempting to portray 100% confidence all of the time without showing any signs of weakness. Michael Freeman, a psychiatrist and faculty member at the UCSF School of Medicine found that Founders are 50% more likely to report having a mental health condition. I wasn’t surprised to read that statistic given everything I’ve learned about
entrepreneurs’ competing priorities and need to depict an impenetrable vision of leadership.

Mike Tyson once said, “everybody has a plan until they get punched in the mouth.” Many of the CEOs and founders I’ve spoken with have incredible educational pedigrees and work experiences, but there is only so much they can do to plan and prepare before actually building their businesses. At the end of the day, these executives are just people who face a lot of the same challenges we are all familiar with, whether it’s about maintaining some balance in our lives or overcoming difficult team dynamics. I believe it is important to continue to have an open dialogue about how we can best support and empathize with these driven Founders so that they can achieve success in their businesses while also maintaining their personal health and happiness.