When my little brother and I were growing up my dad gave each of us a small card with a young boy standing at the edge of a cliff. In small letters it reads: “Some were thought brave because they were afraid to run away.”
The sentiment ran deep for both us. Especially Adam, who went from being the smallest player on the football team to the biggest boy in the gym and eventually senior captain.
Adam’s the kind of person who will punch a shark between the eyes if he’s confronted by one. From a very young age, I’ve admired him for standing so confidently in the face of adversity.
Facing fear in business is the same as facing it in life. It’s terrifying.
Often times, shrinking away is more reassuring than squaring your shoulders, punching the shark, and living to tell the story.
The majority of us have to train ourselves to be like Adam – To overcome the challenges that over time fill in the essential parts of our identities.
My friends, especially the ones who contributed to this post, have been huge supporters of me pushing through my fears.
Today, I’m incredibly grateful to share how Brittany, Julie, Mike, and Aaron overcame daunting challenges running their startups.
Brittany Hodak, Co-founder of ZinePak
In ZinePak’s first two years, I was unwaveringly fearless. My co-founder, Kim, and I were the only two employees of the company, we both worked from home, and we didn’t have any real assets. It felt like we had nothing to lose–and in a lot of ways we didn’t. We were so excited to be free from the metaphorical chains of the corporate world that we relished every opportunity to take a chance. Although many of the choices we made were gutsy (and some perhaps borderline crazy, in retrospect), they helped us create a wonderful foundation for ourselves. It’s impossible to be as fearless today since we’ve got close to a dozen employees who are counting on us to make the right decisions, but we strive to make decisions from a place of optimism and opportunity instead of being ruled by fear. By framing each new challenge in this light, it’s hard to pinpoint any one as the scariest. Had we not jumped in headfirst, so to speak, I think many of the events of our earliest days (and certainly of our more recent days) would feel incredibly intimidating.
Julie Lorch, Director of UX at DoSomething.Org
The scariest thing (in my UX opinion) was the state of our website in 2013. It was massive, broken, and difficult to navigate. In fact, it was such a mess that we scrapped everything and rebuilt the site from the ground up. Our nascent product team refined our design process and built a new site at the same time. We emphasized early prototyping and cross-functional collaboration, bringing tech, design, and content together at the start of a project. Yes, our new site is beautiful, functional, and boasts obscene conversion rates (dirt off your shoulder). But we’re better off because our product and tech team took on a massive challenge, figured out how to get sh*t done, and documented it just enough to improve it for the next build.

Mike Townsend, Co-Founder of HomeHero
I have a deep appreciation for how important focus is. When we first started, we didn’t focus enough on senior care, we considered cleaning, personal assistants, and transportation services all in the same experience and it was a tough lesson for us to find a laser focus on senior care.
Aaron Firestein, Co-founder and Chief Artist at Bucketfeet
This is more of a question for my Co-Founder as he’s head up most of our fundraising endeavors. Like a lot of companies there were some 11th hour moments when trying to raise money, but it worked! I think we’re better off because you know you cannot take how far we’ve come for granted.
If you missed last week’s post on the three traits each founder seeks in new hires tune in here.