Three years ago I started ReadyDone, a small web-dev and design business with my friend Josh Lind. Our goal was to work on some fun projects, source others to friends and other independent contractors, and to make getting and doing creative work easier for everyone. Unfortunately, after two years and a few dozen projects, Josh and I decided to close up shop. While I didn't make uber-bucks from the experience, I did learn a bunch. Below is text from an email I sent Josh shortly after we decided to call it quits.

Josh,

As I'm sure you recall, two and a half years ago we were working together on a start-up that was losing momentum. With funding running short, a game plan smashed to smithereens, and team members cleaving off like chunks from a melting iceberg, I realized that my time playing business man was up. In December 2007, I started looking for a new job and within a few weeks landed at a non-profit with a great mission.

While my new job was exciting, my heart still swelled for the dream of "building something", and you and I had recently talked about making it easier to hire contractors and build projects. So, with $400 invested from each of us, a domain name dreamt up on the Ave and your serious design and dev skills, we launched ReadyDone.com, a consulting company.

During the time that ha passed since, there are many things to be proud of. We presented to angel investors and VC, courted clients, successfully competed projects and sourced jobs to freelancers. All this done without taking on debt. At the end of two years, we closed down ReadyDone with more cash in the bank then when we started. Not too shabby!

Although, as you know, this isn't the whole story.

While many good things came from the ReadyDone business, the biggest take-away for me are the lessons I gained from the experience, an experience I'd chalk up as a flop.

This is what I learned, or at least a start on what I learned. I'm sure I'll expand on this into a successful, NY Times-best-selling memoir, and we'll both eventually be toasting champaign to this tomb of regret when taking breaks from racing our Teslas on the sandy beaches of some far off island

In the meantime, this is what I learned...

Be Flexible, But Plan Like You Mean It

I don't think we ever sat down and talked about what the "it" was for our business or researched what else was out there to any great extent before we started developing a consulting company called ReadyDone. That's probably fine in most cases, and is probably how 90% of businesses start. However, I think when it comes to partnerships, we could have gotten our idea a bit clearer to each other and ourselves, before we started picking the color of drapes for our office. This misalignment ended up causing boatloads of passive aggressive energy and internal frustration for both of us. Unfortunately, we weren't able to effectively monetize either of these new-found minerals.

Only Do One Thing

Coming off the heels of our previous start-up experience, you would think we would do everything possible to avoid this, but I think we fell for the "everything now" error. From The Talented Group, the networking group we explored launching, to our website with profiles for talent and by developing internal projects like Drip Networks, we took on too much.

If I were to do it again, I would take the simplest "equation" for a business, and focused solely on that for a year. If that's a web dev firm, that's fine. If it's an internal project, probably even better. It was most likely my enthusiasm and too much coffee that steered this ship off the edge of the ocean. I take responsibility. The problem wasn't finding the next best thing (God knows we had the ideas and inspiration). The problem was trying to finding the next fifteen best things.

Build the Right Team (Only Do Things You Want to Do)

One questions I never asked myself was, "are we the right folks to be doing this?" I should have. While I try to give my best at anything that I'm assigned, one's best is sometimes not even "good".  Asking me to be a designer or the finance manager, is probably a bad call. I'll try, but the end result will likely be wasted time and a poor product. Similarly, asking you to play customer service with testy clients or present at conferences is probably not the best use of your talents.

What I've learned is that of course people can attempt anything they want to. But ultimately, it is unsustainable to work on something that a person is either not good at or does not completely enjoy. We might not have been the best team for the consulting company we wanted to build.

Make Time

Because we were launching ReadyDone on the cheap, and because I couldn't pay my own way immediately with projects from clients, I worked full-time, volunteered a bunch and still expected to fit in building a company. That actually, can happen. Just not in the type of work I was pursuing.

This reminds me of a story from David Heinemeier Hansson, the creator of Basecamp. At a Stanford Though-Leaders lecture He first wrote the software in just 10 hours a week, while he also went to school and worked on other projects. It is totally possible to make something with just a few hours of work each week. But for human-based businesses, businesses that require a real, daytime time-commitment, I can't be serious in thinking I'd be able to do my RD job at 10 or 11pm at night unless I could agree for all my potential clients and talent to do the same.

No matter my best intentions or coffee consumption. It's not going to happen. Similarly, if the only person working during the day is the partner who doesn't enjoy doing the marketing work (you) or project management work, then why would we ever think that the business would function properly. It couldn't, and didn't. The structure was off. I should have made time at the right moments.

Despite these the regrets listed above, I enjoyed working on this with you. ReadyDone taught me a lot. Thanks for being a partner in the journey!

So, that's it. That's my main take-aways from the ReadyDone experience. Luckily, Josh and I are still good friends and maybe one day we'll work together again.