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.