The truth about being a first-time female entrepreneur

Lisa Rossi
7 min readSep 26, 2019

Sitting in a Starbucks table in downtown Des Moines, a woman asked me what it was like to be an entrepreneur. She was thinking of taking the plunge herself.

I sputtered out a fake answer while this story flew through my head. I didn’t get a chance to tell it, but I’d like to tell it now.

I started a business because I saw a need for better collaboration and innovation in my community and my heart burned to solve it.

But damn.

It’s scary.

It’s wake-up-in the middle of the night scary, dry-mouth-before a presentation scary; it’s the kind of scary a child learning to swim feels jumping into the water for the very first time. As an entrepreneur, it’s like that feeling. On repeat.

At the same time, this has been the most rewarding year of my life, with the most growth and hope for my ability to make a difference than any year of my career.

Bonfire cofounders Lisa Rossi and Nathan Groepper following an early morning workshop at Drake University in Des Moines, Iowa.

Bonfire Strategy, a company I co-own with my business partner Nathan Groepper, turns 1 on Oct. 31. Before our 12-month mark, we’ve booked what I would consider a steady stream of dream clients, excited for learning and change. Those include Drake University and The Greater Des Moines Leadership Institute, who tasked us to support them through reinvention projects in higher education and community leadership. The seeds of this company were planted during my participation in the John S. Knight Journalism Fellowship at Stanford University, where I learned a process of innovation called design thinking. Design thinking is fueled by the listening and empathy I had deployed repeatedly in my previous career as a local journalist. Together, Nathan and I built an idea for how design thinking could build stronger communities, just like local journalism has always reached for.

This first year has surpassed my expectations, particularly with the willingness of early adopters in the Des Moines business and academic community to bring design thinking into their enterprises.

On behalf of Bonfire Strategy, I recently trained Mandela Washington fellows in residence at Drake University in design thinking

But what I need to say here isn’t about the mechanics of the business. It’s about the mechanics of myself as a leader and entrepreneur.

I thought I knew about leadership before. I had been a manager. But entrepreneurship is completely different. My first year of being an entrepreneur involved an enormous amount of work — on myself.

While I was simultaneously developing our service offerings and recruiting new business, I did an intense personal audit. In essence, I turned the problem-solving process of design thinking on myself, looking inward, diagnosing problems to be solved, and rapidly experimenting.

It’s a journey that started during my time at Stanford, where I began regularly seeing a therapist. At the end of my fellowship, I also picked up a design thinking personal journal, and documented my energy and engagement as it related to each activity of my day.

I learned my health was struggling under my ambitions. Through my journaling, I noticed I didn’t work out. Halfway through my first year as a business owner, I started exercising — not just regularly — daily. This was not a quest to get thin. This was a journey to silence the voice in my head telling me I couldn’t do it. Somehow, when my entire body was shaking trying to hold a crow pose during yoga, that mean little voice withered.

The issue of confidence turned out to be a factor I confronted repeatedly. I turned down exciting jobs after my fellowship and moved back to my hometown of Des Moines to chart my own path. But I had a hard time with the transition. I was surrounded by a support network at Stanford, world-class educational opportunities and all those palm trees. In Des Moines, I had a windowless basement office right next to the cat box. On lots of days, I forget about the fellowship and instead fought against doubts that I was legitimate and that I deserved a voice in the business community.

I remember one of my first networking events as a co-founder, at a co-working space in downtown Des Moines. I grabbed a glass of wine, shook hands with a man standing near by and gave him my elevator pitch. At the end of our conversation, he told me he was confident that I had no idea what my company actually was. Maybe the comment was meant to be constructive — of course entrepreneurs grow enormously in their understanding in the first year. But I choose to let his words feed a spiral of self-defeating thoughts, which dumped into a morass of memories of all the times I hadn’t been invited to the conference room table.

I went to one more networking event and stood awkwardly in the back of the room until a friend found me and led me around introducing me to others. After that, I realized I was better at making connection during one-on-one coffees with people I knew.

I kept going to therapy. And we talked about rest. This journey was going to be challenging. And unlike my days as a journalist, I didn’t have an entire newsroom behind me. It was Nathan and me, day-by-day figuring it out. I now make sure my Saturdays are restful, a muscle I had to build. I was ashamed at first. I should be cooking for my family! Socializing in my neighborhood! Reorganizing the closets!

Nope. What I need to be doing is restoring my own voice, telling me I can do this. Sometimes that means a Netflix binge. Other days, it’s a long swim at the pool or quality time with my family. Nothing difficult.

It works.

I blast into Monday like a firecracker when I get this right. I started amping up my presence at community events while also building my abilities to confidently share my knowledge with my clients. We have a list of big, exciting projects on our horizon, including a series of workshops in partnership with the Drake School of Journalism and Mass Communication to reinvent journalism. Just recently, I joined the Des Moines Downtown Chamber of Commerce, a community I found to be enormously supportive to a first-time business owner.

This quote from the UCB Comedy Improvisational Manual pushed me to take risks.

Finally, as I saw my professional world morph, I wanted the same level of growth in my marriage and relationship with my kids. I was determined to bring my learners’ mindset to the most important area of my life: My family. My husband and I have worked hard on building the depth of our own connection in the face of growing careers, multiple relocations, and daily pressures. And my kids and I are growing together too. This summer, I learned how to swim, after giving up years ago, alongside my 6-year-old, learning the basics, and my 8-year-old, fine-tuning his front crawl. Now, I jump in the water with my family instead of sitting on the sidelines, laughing as I mess up and celebrating with them when I get it right.

My 6-year-old son recently made me this Lego creation of a woman at the helm of a spaceship.

So that’s it. Today, I simply want to share the truth with any other woman who thinks she just might want to own her own business, which in Iowa, is an area where we can grow.

My advice? Go for it. But take really good care of yourself on the way.

Resources I used during my first year as a business owner:

The Designing Your Life Workbook: This helped me identify the areas of my life that needed growth and attention.

DreamBuilders at the Iowa Center for Economic Success: I learned about all aspects of managing a new business, from marketing and customer research, to accounting and finance.

Mentor Connection through the Greater Des Moines Partnership: I signed up for a mentor locally, and have been fortunate to receive support from Amy Hutchins, the founder of MarketLogic, a sales and marketing consultancy.


Mindset: The New Psychology of Success: Stanford psychology professor Carol S. Dweck’s description of the growth mindset helped me understand that what I didn’t know wasn’t a permannet character flaw — and that I can learn new skills through hard work.

Each morning, I look at this chart from Dweck’s book, taped to my bathroom mirror.

The War For Kindness: Another Stanford psychology professor, Jamil Zaky, built on Dweck’s work on the growth mindset and applied it to empathy. When we are empathetic with ourselves — and others — our efforts for change and impact are so much more effective. And empathy is also a skill that we can practice and learn.

The Achievement Habit: This book by Stanford cofounder Bernard Roth has been my lifeline. I read little bits of it almost daily to push me past my fear to action.



Lisa Rossi

Obsessed with the growth mindset, design thinking and telling great stories.