Accelerating my business learning: setting a goal for a new business every month

Posted: - Modified: | entrepreneurship, experiment

The first year of my five-year experiment is going well. I learned how to set up the structures for five different kinds of service businesses:

  • web development contracting
  • social business consulting
  • illustration
  • conference/event sketchnoting
  • public speaking

and two kinds of product businesses:

  • writing e-books
  • selling used books

… and I got to my first sale (and often beyond!) for each of them (WOOHOO!), which is a thrilling milestone to reach. In addition, I brainstormed more than a dozen other business models that might be interesting to explore, and listed even more ideas for things I wanted to see fixed.

I learned a ton from events, books, and conversations – and what’s even more fun is that I finally got to put into practice some of the things I’ve been learning about entrepreneurship and negotiation. It’s true! You learn things so much more deeply when you actually get to use them.

Looking back, it’s hard to imagine any better way I could’ve used that time. Leaving the relative certainty of a corporate environment was definitely the right thing to do. Gradually learning about business through a combination of familiar skills and new opportunities – that was a good thing to do as well.

Seven(!) micro-business experiments in almost a year works out to a business experiment roughly every two months. Let me look at the pattern more closely:

Business First sale
Social business consulting March
Illustration April
Used book sales April
Web development contracting May
Writing e-books June
Public speaking August
Conference/event sketchnoting December

What could happen if I experiment with trying to build a business every month? When I first started considering it, I thought: “That sounds intense!” But looking at this past year, it’s almost like taking that first sprint of March to August (six businesses in seven months) and extending it just a few more months. What could I learn and share if I had the capability to test an idea every month? How could I learn how to structure it so that my co-experimenters – people who are interested in being part of this, and the clients who are part of that first sale – get the value they want without being burned by the nature of the experiment?

I think that would be an interesting book – something along the lines of Start-up of the Month. I’d love to read it. I could wait for someone else to write it, but I’m not sure how many people have the time and space and combination of skills to go ahead and try it, so maybe I can write it.

I’ll start in March, because I want to make sure that my current consulting clients are totally happy and that they transition well to being independent. There are lots of things I can do to prepare for that. Part of that preparation includes imagining what it would look like and feel like if I had this smoothly running machine for generating and testing ideas.

Being super-good at building a new thing each month means being able to:

  • Generate business value propositions, perhaps picking common markets/personas so that I can get transferable insights and good lists for validating ideas
  • Quickly validate problems and solutions through interviews (maybe through Skype – a community of early adopters who are willing to let me pick their brains?)
  • Create visual mockups and sign-up pages
  • Test pricing and get payment
  • Build minimum viable products using popular APIs and toolkits
  • Do a whole bunch of businesses and then evaluate which ones to invest more time in, or even spin them off as people are interested

To prepare for that, I can:

  • Add more business ideas to the list of  things
  • Flesh out more business models
  • Start building my tribe of co-experimenters (people who are interested in the journey? potential customers?)
  • Map how the different business models relate to each other, so I can organize them in a logical sequence
  • Develop my prototyping skills (mockup, design, MVP)

The risks:

  • Creating new businesses as experiments can be risky – why should people buy from a pop-up business that may not be around later on? Maybe I can draw ideas from software lifecycles: each month, there’d be a business in startup phase, a business in go phase, and a business in maintenance phase, and I’d build processes or open up the possibilities so that people can take over the business if it promises to be interesting.
  • Supporting previous businesses can distract me from creating new ones. Again, processes can help here.
  • Business start-up costs can be high; will I see the return on investment? Possibly, if I stay laser-focused on creating that first customer with a minimum viable product. Also, I’ll get a lot of value from the learning.

I think this will be an excellent use of my second year of the experiment, and a good foundation for the other years. Exciting times! Whom should I learn from? Who wants to learn with me? How can we get started?

You can comment with Disqus or you can e-mail me at