So Many Tries, So Many Entrepreneurial Failures

Recently, a friend was asking about entrepreneurial endeavors I’d tried over the years, and I realized it’d be fun to enumerate them and reflect on lessons learned. From starting a business, talking to customers, finding solutions, and working to build a sustainable business — every part of the entrepreneurial journey is a learning experience.

Here are some of the ideas I tried, in chronological order.

  • Lawn maintenance service – Enjoyed the work, only did it passively as jobs came in
  • Shareware software – Loved programming and fascinated by the idea strangers would pay for software over the Internet without talking to anyone
  • Local classified ads – Bought a second phone line and connected an answering machine for people to call in with their ads, placed printed classified ads in two local restaurants, realized quickly there wasn’t much demand
  • Sports cards dealer – Loved tracking the players, buying cards from different markets, and helping people complete their collections
  • Web design – Enjoyed the creative process of designing a site in Photoshop, crafting all the pages by hand (HTML + Dreamweaver), and delivering a finished product to the client
  • College textbook exchange – Provided a quality solution to students and learned there’s a number of structural challenges to changing the textbook market
  • College professor rating service – Students loved leaving ratings and reviews but a number of ethical questions arose and there was a lack of interest scaling it
  • College laundry service – Clear product demand but a number of logistical and pricing/margin challenges
  • College online food ordering – Built a working prototype but couldn’t get adoption from restaurants without point of sale integration (times are different now, 20 years later)

In hindsight, each idea played on something I was personally interested in and simply translated into a service for the market.

Every idea was a failure in that I wasn’t able to make it into a sustainable, profitable business.

Every idea was a success in that I created a product or service, brought it to market, and gained more experience.

The lesson: it takes a number of failures before a success. Find a problem, create a solution, and start a business — the more you try, the more you learn.

2 thoughts on “So Many Tries, So Many Entrepreneurial Failures

  1. Hi David, Morgan here from SLC, UT. Love all the work you’re doing to open the world of startups to the masses. As someone working at a startup in the angel investing world, appreciate your insight.


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