SBC February Newsletter: Learning from an Entrepreneur & Millennial Mindset
Erik Benjamins: How did you choose the path of entrepreneurship?
Ryan Sheffer: Up until I was applying for college, I thought that “becoming a business person” was the thing you did as a career. I didn’t know that becoming a filmmaker—or doing your own thing—could be a job. In my head, it seemed like something that others did. When I started to get into the technology industry about ten years later to start my own company, I didn’t know what venture capital was. I didn’t use the word entrepreneur to describe myself. I was just an editor doing my own thing. I had this inherent desire for freedom, but didn’t have a clear cut way to define it. I realized that the key to choosing a path was understanding that it’s there. We often define our ceiling because it’s what we’ve seen, what we know.
EB: When was that moment for you? When you shifted from working in the film industry to the tech industry?
RS: It was a process. I was always brought into the film industry as the tech person that you’d call when something was technically difficult. Around that same time, I made a New Year’s resolution to teach myself how to code. It made sense given my interest in the tech side of the film industry. A few months later I sat down with some coders and showed them what I built after dedicating a month to learning this new language and they thought it was pretty good. I walked away from that meeting thinking that this may be something I could do. It was a shift in perspective.
EB: Tell us about your interests in an open source education?
RS: Before teaching myself how to code, I taught myself how to use a camera. My desire to continually learn has objectively fueled my career path. When I first went out and tried to start a company, I felt like no one wanted to share the simple things. Everything I found online were either stories of great success or massive failures. There wasn’t any “brass tacks” information like what to do when hiring a lawyer. No one thinks these are interesting things to share, but it was all I wanted to know. I started a video series called 12 Months to share these brass tacks kinds of things I was learning as I was starting my own tech company. It didn’t do very well, but I did get a lot of emails from people thanking me for being open and honest about all the non-sexy stuff I had to go through.
My blog has been the most successful thing I’ve done in my career. It now gets hundreds of thousands of reads per year. My outlets for sharing these process, successes and failures have a lot to do with sharing outward, but also forcing myself to verbalize my process. It lets me understand and follow through on it.
EB: What have you learned about your professional trajectory thus far?
RS: I need to be building something ambitious. Success isn’t going to happen instantly so I want to build something that will light me up as I struggle through it. Setting ambitious goals lets me work as my best self. The most important thing for me is to pursue my own excitement about learning and discovering, pushing myself to be better and better.
EB: How do you see and engage with risk in your work?
RS: I don’t see risk the way others might. With my first foray into the tech industry, I invested a lot of my own money I had been making as a filmmaker into a company that I eventually ended up shutting down. But I viewed that decision as an education. I could have spent the same amount of money for a masters or PhD, but I’d rather invest in this style of learning. That being said, I’m starting a family now and need to work in a more responsible way. Risk is important, but I also need to set hard deadlines. For example, I’m in the process of fundraising right now and if I don’t raise the amount I need, I’ll have to put the company on hold and find a job.
EB: What advice do you have for someone struggling with their identity as a worker, or someone interested in taking the non-obvious work path?
RS: If you find yourself working at a job and you feel like they can’t give you enough work to do and you have six other side projects going, you’re not an employee. You can either choose to refocus your energy towards being an employee or you can accept that this seems like the energy of someone who wants to start their own thing.
EB: How can upper management engage with entrepreneurial minded talent?
RS: I had an employee like this and my method was to put that person in charge of their own department. I gave them as much autonomy as I could without sacrificing the clarity of vision for the company. Once you identity someone with an entrepreneurial spirit you need to incentivize them with responsibility and autonomy. My experience in the film industry helped with this. The director is the dictator, but he or she surrounds themselves with department heads like lighting, costume, etc., that make large decisions without the director’s constant oversight. When it comes to managing Millennials, it’s about working with people who have a ton of passion and have a desire to have an ownership in what they do.
EB: Is this an experience that for you is generationally specific?
RS: I don’t like using the phrase the “Millennial attitude”, but there is definitely an element of Millennials not wanting to hear you tell them your business. The counterpoint of empowering Millennials is that they may feel deserving of autonomy, but are unable to provide the output. The “Millennial attitude” lends itself to a side effect in which the second you micromanage, they are upset. It’s an attitude of “we do it differently and you don’t understand”. It may also have to do with the fact that jobs and work is shifting. For example, I don’t have folders and I don’t have an office. My whole company works remotely. There’s an element of needing to find people that work more comfortably in that environment, to be go getters and get stuff done. I think we’ll see a trend of a company having it’s separate sections run like individual companies.
EB: Lastly, who has been your influence or inspiration?
RS: My grandfather for always wanting to learn and my father for being the most dedicated family man I know.
It never hurts to reflect on the powers, complexities, and new styles of the Millennial mentality as we continue flying into this new year. It speaks to the changing nature of work and our ability to balance existing structures with entirely new ones so we can do our best work.