I recently had a chance to sit down with John Saddington. John has been an executive at some of the largest companies in the world and has started, exited, and invested in a handful of bootstrapped and VC-funded start ups. His current project, Desk, was recently awarded Best App of 2014 by Apple.
Let’s get into the interview.
Can you explain what Desk is and why you started it?
Desk is a project that I actually thought about back in May of 2002. I had purchased a car off of ebay and was traveling to pick it up. While I was traveling, I couldn’t blog while I was on the road and wished I had a desktop publishing client. This is when I first visualized it, but knew it would have to wait.
It ended up taking about 350 days to build and it has been out about 75 days at this point.
Were you surprised that Desk was awarded one of the best apps of 2014 by Apple?
This was totally a surprise to be given this award and totally humbling experience at the same time.
Can you explain what you are doing over at The Iron Yard?
We are doing a couple of things there. We are helping to accelerate companies and we are investing in students. We have nearly 50 portfolio companies. A couple of them have done outstanding. The other side of this is education. As companies grew, we knew there was going to be a lack of good development talent. This would help with that problem.
In late 2013, we decided to expand. During that time, we have scaled 10x. We went from 4 employees to over 40 in one year.
I know you are a very busy guy. How do you stay organized and what are some of the tools that you use?
I do not subscribe to any mainstream methodology on this (i.e. GTD). I do not use a to-do list and do not use any task management software either. I use “Frankenstein” approach with my email. It is my to-do list, calendar, and everything else.
If someone would see this without any context, they would think that it is crazy. One of the keys to staying organized for me is that I have created a boundary system and those most important to me are very patient with me on this.
You’ve wrote about getting up early in the morning. What does a typical morning look like for you?
I am not sure that any morning is typical. However, I do all of my writing in the morning before my daughters wake up at 7:00 a.m. I typically get up around 5:00 a.m. and can write up to 7,000 words during this time. This is when I feel the most productive with my writing.
Have you always been this way?
No, not really. This is something that I have learned about myself over time.
Do you have a similar routine in the evening?
All of my software development is done during this time. I find that this is the best time for me to do this type of work.
With the type of schedule you are running, how much sleep do you typically get each night?
It is usually anywhere from 4-6 hours. I had some major health problems a while back. I lost 31 pounds in the past year and am much healthier now. This has really helped with my sleep. For anyone who is reading this, your health should be your #1 priority. It will change everything for you.
We touched on this a little bit earlier. How do you actually handle email since it is controlling everything for you?
It is not a real rigid approach. I try to get to inbox zero. What this means to me might be different than what it means to someone else. I either delete the message (i.e. ignore it), archive it, or respond immediately. Most of it, I simply delete, because it is just not that important. If it is not critical, I just don’t do it.
How do you stay away from doing busy work that a lot of people get caught up in and do not get any real work done?
I am really not sure how I do this. It is really a grand annoyance for me to see an inbox full of nothing. This is where I typically answer it immediately or I delete it. If not, it will get lost in the ether and no one cares. It seems like a lot of people are not able to prioritize email. By not doing this, everything becomes a priority and this is a problem. There are so many things out there more important than answering emails. I have people to mentor and software to build. I am the only one who can be a husband to my wife and a dad to my children. These are the important things I need to be doing.
How do you know when it is time to kill a project you are working on (i.e. Pressgram)? Is this a gut decision?
It can be a gut decision. However, the problem with using this exclusively is that it is all emotional. Emotional decisions can cloud judgment very quickly. You really have to be careful of this. Pressgram was a disaster as a business. It was a great product though. Just a bad business. You have to look at the whole situation.
What social media do you use? Do you still only use Twitter?
I actually just quit Twitter yesterday and wrote on my blog about this. It was consuming too much of my emotional time. The value of using it became very low for me. Because of this, I decided to stop using it.
How do you stay balanced with work and family?
I don’t really agree with work life balance. I think of it more as tension like you would have with a rubber band. The idea is how you manage that tension so the rubber band doesn’t break. There are times when you have to deal with the tension that is higher. This really depends on the season you are in at the time. You can look at this for the future if you don’t like how it is going and say to yourself that you are going to try and do better. You have to actually do something to change it though if you don’t like it.
One thing Michael Hyatt talks about is “The Drift”. How do you stop yourself from falling into this drift?
I do think this is a real thing. I believe that we all have blind spots that we cannot see ourselves. I think that the best remedy for this is having people around that you trust and care about you to see these things for you. They can help you stay on track by seeing the things you cannot.
What advice do you have for people who are afraid to fail?
I don’t really have any grad statements on this. I personally would much rather do than regret. I would rather know that I tried and failed as opposed to do nothing. I think one of the biggest failures that you can have is to regret your time. I want to maximize my time.
I have seen that you were teaching one of your daughters some basic programming. How important do you think it is for young kids to learn?
Exposure to it for sure. I try to expose them to as many things as possible. Every company is a technology company now. To be able to speak intelligently about technology is a liberal art. I really think it going to be very important to know how to speak intelligently about it more so than it already is.
One final question, because I am a geek at heart, what do your workstation setup at home look like?
You would be surprised how sparse it is. I use an 11 in macbook air with some cloud based storage (dropbox, google drive, and icloud) and that is about it. Here is a picture of what it actually looks like in a blog post that I wrote recently. A lot of people can’t believe that this is it.