Andy has been running his one-person bootstrapped software company for more than ten years. He has two products:
- PerfectTablePlan which creates the best table seating plan in the least time, and
- Hyper Plan which combines the simplicity of sticking colored notes to the wall with the flexibility of software.
Andy tells us why he bootstrapped, how he balances two products, how he stays motivated, and the changes he has seen over the years in our industry.
Peldi Guilizzoni from Balsamiq says he was inspired by you to start his business. Who inspired you and gave you the desire and motivation to bootstrap a software company?
For 20 years I worked for other people writing software that they paid me to write. Most of it never got used, which was very frustrating. So when the dotcom company I was working for laid me off I decided to strike out on my own. Having seen in the dotcom company how stressful it was dealing with investors, I never wanted to take investment.
Two of my friends had been running a small software business for a while. So that gave me the confidence that it was do-able.
I was also inspired by the dotcom boom and bust. A lot of people had started companies who clearly had no idea what they were doing. If they could do it, why couldn’t I?
Lots of other people have helped and inspired me along the way. Too many to mention. But Joel Spolsky’s Business of Software Forum was important in the early days.
It is interesting to see how the people who were on the Business of Software Forum at same time as me have gone off into different directions. Peldi has been very successful at growing his company. He
should be very proud of what he has achieved. But employing lots of people sounds stressful and I have consciously decided not to follow that path.
How did your life change as a consequence of creating PerfectTablePlan as a bootstrapped business?
After a couple of lean years, I am now significantly better off financially and I have a lot more flexibility and freedom in my day-to-day life. My commute is about ten meters and I never have to set an alarm clock for work. So it is mostly very positive. But of course there are always negatives. It can be isolating to work on your own. So I try to keep in touch with other bootstrappers and I do some volunteering to get out of the office.
Developing, marketing, and supporting one product is already a challenge for a one-person company. Why did you add a second product to your workload?
Trying to keep two products moving forward on your own is certainly a challenge. But I felt I had all my eggs in one basket with PerfectTablePlan and no product lasts forever. So I wanted to diversify
a bit. There was also the danger of getting stale after working on PerfectTablePlan continuously since 2005. And the idea for Hyper Plan had been burning a hole in my brain for quite a while. Plus I was in the fortunate position of being able to use the income for PerfectTablePlan to finance the development of Hyper Plan.
How do you balance the day-to-day operations of your two products?
Using Hyper Plan, of course!
I naturally alternate between working on PerfectTablePlan and Hyper Plan. And I try to keep a balance between the reactive stuff (bug fixing, support) and the longer term stuff (major releases, marketing). I never promise release dates to customers and that takes the pressure off a lot.
You started your bootstrapped company in 2005. It is now 2019. Tell us how you deal with the struggle to stay motivated day after day, year after year.
I have tried to keep things varied. As well as creating, supporting and marketing products I have also done some consulting (mostly helping programmers launching products with their marketing) and run some face-to-face training courses for others wanting to start a software business. Having paying customers also helps a lot with motivation.
But staying motivated definitely can be a struggle at times. I think that part of it is accepting that you will go through periods when you have lost your mojo. Don’t beat yourself up about it.
Also I think it is important to exercise. I try to get out of the office to run, cycle, swim or do some martial arts most days.
What changes have you seen in the bootstrapped software industry over the years with regards to sales and marketing strategies?
Obviously the big changes in the market are the move from Windows and Mac software to web-based products with subscriptions and mobile software. The mobile market looks horrible. But maybe I will do a web-based product one day. Some products still make more sense on the desktop.
The marketing channels are changing all the time. For example, download sites like
Tucows.com were big in 2005. And I used to advertise in glossy wedding magazines - remember magazines? And I could get targeted clicks for £0.05 each on Google Adwords!
But human nature doesn’t change very much, so the basics of marketing and sales remain the same.
Compared to when you started, what advantages do first-time bootstrappers have in 2019?
It is easier to write and distribute software now. But that is a double-edged sword as it means a lot more competition. So I think that marketing skills are increasingly important.
What words of advice do you have to someone dreaming today of creating and launching their first bootstrapped product?
I wrote a whole 2 day course on this. So it is hard to condense it down a few sentences!
Bootstrapping a software company is hard. Don’t believe anyone who tells you different - they are probably trying to sell you something. If you don’t have plenty of energy, drive and determination - it’s not for you.
It is useful to learn from forums, books and courses before taking the plunge. But the real learning only starts when you create something and try to get people to pay for it.
Be prepared to learn marketing, sales and business skills. If you want to just program, you are probably better off working for someone else.
Release something as soon as you think it might be useful to someone and iterate like crazy based on the feedback. Be flexible - often the opportunity turns out to be quite different to what you expected.
Strangers giving you money is the only true validation.
When you are running a business there is a near infinite list of things to do and you are never quite sure which one to do next. Get used to it.
Don’t be put off by not knowing everything before you start. No-one starting their first software company has any real idea what they are doing (especially if they think they do).