Wednesday, July 31, 2024

Lessons from the Roadside: Embracing Failure in Entrepreneurship


I identify as an entrepreneur - more accurately, a failed entrepreneur - but an entrepreneur, nonetheless. My personal experiences have taught me that failure is not a destination, it’s that strange, potentially intimidating rest stop you may be forced to visit during your entrepreneurial journey through the start-up desert, inching toward the oasis on the other side. Failure is that detour that makes you go “huh…” once its finally in your rearview mirror. In my younger years, I have had the opportunity to stop off at three of these less-than-ideal roadside attractions, each teaching me something new.

My first business, a DJ service called “Shooting Star DJ” (2006-2011), taught me the importance of vision. If only I had asked myself “what happens if I book every single Friday and Saturday into perpetuity?” The public kept crying out “Please don’t stop the music,” but I never considered how pricing and geographic logistics were impacting my business. More importantly, I never considered how I could scale or how scale would affect my offering or my willingness to continue the business. Charging $300 per event with no additional fees for travel or extra hours, I aimed to be the most cost-effective DJ in Northern Iowa. This often meant driving up to three hours one way for gigs, resulting in long hours for little return. This experience taught me the need for vision, understanding scale, and knowing how to price value. Undercharging "Killed the Radio Star." Vision and strategic planned scaling ended up being more crucial than the incremental gig.

My second venture was being a landlord while pursing my undergraduate degree at Iowa State University (2008-2013). My projections PROVED that buying a house was a no brainer: my roommates would pay my mortgage, I would build equity, and eventually, sell the house at a profit after graduation. What did Robert Burns say about the best laid plans? I learned about risk very early in this venture when my “on a handshake” tenants/roommates no-showed on move-in day. Successful entrepreneurs are experts in knowing, respecting, and adapting to risk, none of which I was equipped for in my late teens and early twenties. This venture served as tuition to a school that taught me how to respect risk and understand the difference between projections and actual results.

My third business started after I launched Certified Iowa Agricultural Products, Inc. in 2011. My goal was to develop a brand like Certified Angus Beef, where agricultural products such as beef, pork, dairy, eggs, and poultry produced in Iowa could be certified as traceable Iowa products. This certification aimed to attract consumers who preferred to eat local, valued product traceability, or appreciated Iowa’s high-quality food production.

To bridge the gap and prove the concept while developing a brand and certification program, I sold Niess family-raised beef directly to consumers via farmers markets and Facebook. In 2011, selling meat outside of grocery stores was a relatively new concept, and while the value in traceability and eating local was gaining traction, they were not yet priorities for Midwest consumers. I broke even in 2011, but the market didn’t embrace the value I was offering. I dissolved Certified Iowa Agricultural Products, Inc. in 2012, believing that any future efforts would have a negative return. This experience, in hindsight, taught me that successful entrepreneurs must exhibit disciplined patience and persistence. Success typically comes from continuous effort and improvement, a willingness to climb a mountain without seeing its peak.

The overarching theme is that successful entrepreneurs choose not to go it alone. My actual failure was trying to do too many things, be everything to everyone, and because I didn’t want to give up opportunity, chose to go about building and growing businesses alone. Those strange rest stops and detours weren’t just the universe’s way of giving me a good laugh—they were necessary lessons that shaped my understanding of entrepreneurship. Through my failed ventures, I've learned that in entrepreneurship, the only true failure is failing to grow, and that success is something born out of innovation, resilience, vision, adaptability, and the ability to understand risk. 

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