_{Ottawa-based startup DevShop provides a hosted project management tool for software developers. Founder Craig Fitzpatrick recently tested a private beta and launched a public beta this week. Red Canary caught up with Craig to talk about his background, his experiences as a founder and how DevShop gave him a taste of his own risk-analysis medicine.}

For a more robust overview of DevShop’s functionality and UI, read the Techcrunch review.

How’s your workload at DevShop these days?

It’s been a bit lighter since I got private beta out. it was a pretty big milestone, arguably bigger than public beta or even launch.

Tell me about your background

I started coding when I was about 9 – I chose poorly when I got my first computer, a TRS80. I had to type in 50 pages of code to play hangman.

The TRS80 in all its TV-as-Monitor glory

And after College/University?

I had a portfolio of my own software by that point. I applied to my first job and coded for the first two years but then quickly hopped tracks and became a manager.

What led you into software management?
It was a means of influence. If I had vision for something then not only could I work on it myself but I could put a team on it.

So you’ve worked for quite a few small, startup-type companies?
[Ultimately] I was hired as head of development – typically to get [startups] out of the ‘cowboy’ stage, where there’s founders and maybeup to, say, 10 employees. They’ve got a prototype [and] they’re out on the market – they need to scale things up and put some rigor in the process.

I’ve never worked for a company with more than a hundred people.

You’re better off.
That’s what I hear!

“The turning point that led to DevShop was that I realized that development mistakes were being made everywhere”.

I was with a company doing online collaboration software – big deployments. They didn’t really want to exit the ‘cowboy stage’ and I just got frustrated. We experienced a lot of failures as a team, there was a lot of stress and mistakes being repeated. The turning point (that led to DevShop) was that I realized that these mistakes were being made everywhere.

What kind of mistakes?

It was professional naivety in the sense that when you sit down to build something from scratch….well I guess it’s human nature but we always tend to plan the best case. The reality is the direct opposite.

Craig Fitzpatrick, Devshop. Craig’s blog can be visited here

I’d present the first part of the plan which would have padding and buffer and risk-mitigation built in – and that would get stripped out. Three months later they’d realize “oh, that really would have helped”. I realized that this happens everywhere.

So there’s the ‘pain’ DevShop bandages. How did you roll forward from there?

It was after that I realized with a 70% failure rate for software projects [project software] cannot be wholly to blame. That’s when I really stopped and said “I know this field: what would I want as a dream product to be able to manage these projects, build in all of the [software project management] experience that I have accumulated and make it so that if a newbie starts using it they’re going to succeed without ever having managed before?”.

“As a software leader you always have to be the pessimist, you have to think: what are the things that are potentially going to kill me”

Most software developers or managers don’t ever get trained [in project managment] because they begin as developers. I figured the place to inject experience was in the tool – because everyone uses a tool – Microsoft Project, BaseCamp, even Excel. My first step was to try to design a better tool.

“The whole DevShop model was prototyped before I’d written a stitch of code”

Tell me about DevShop’s unique development

(see this DevShop screenshot larger here)

I went through about 7 iterations on design – I started in Excel and got feedback, then went into photoshop and created some screenshots and shopped that around…then HTML. It was very much a front-to-back thing. I always knew (by looking at the UI) – what exactly I was trying to build. It’s now how I’d advocate any software be built.

So what does DevShop do?

Project management just for software teams. Most project management tools are strictly general purpose. In software project managment, the dynamics are different the challenges are different, and the risks are different. [DevShop] is domain specific.

If you’re a software manager your #1 job is risk-management. The way requirements are managed (or lack of it) kills projects. Interestingly enough, people typically know what’s killing them, but they don’t know what to do about it. I can productize [that].

“Dev cycles are shortening…you have to be reactive. Requirements are going to change…you need to plan for it. Accept them as the norm and figure out ways to deal with them so they don’t kill you”

If you’re a software manager your #1 job is risk-management. The way requirements are managed (or lack of it) kills projects. Requirements change all the way through the [development] cycle. Interestingly enough, people typically know what’s killing them, but they don’t know what to do about it. That means I can productize [it].

Tell me what you’ve built into it that separates it from traditional tools?

Let’s say you’re building a new project plan, you’ve worked with your team on one product and now you’re starting a new product…when you sit down you break up the work and start assigning tasks to people – DevShop has gotten to know those people.

“It’s like shoemaker’s children…the people that produce the tools don’t always have the best tools themselves”

Do you plan to sell small, medium or enterprise customers?

It’s more the nature of the team than the nature of the company: from a marketing strategy point of view I’m focusing on the small- to medium-sized shop.

(see this DevShop screenshot larger here)

Did you ever consider a boxed version of DevShop as opposed to Saas?

Boxed was the plan originally…but I’m a believer that hosted software is going to be a major force going forward.

What was the single largest challenge into getting to Private Beta?

What did you run into that you didn’t expect? Here I am developing this project planning software where one of the features is time estimation error….so I’m able to track my own time estimation error and it turns out to be about 300%! I’m a victim of that just like everyone else.

Anything else?

It turns out that everyone and their dog forgets their password….I personally emailed [a password] to about 200 people in the first few weeks. So here I am writing a ‘I forgot my password feature’ [for DevShop]. But I got to talk to a lot of people!

I invested a lot of time in the rich user interface to make it a lot like a desktop app. It turns out that has gotten a lot of attention. A lot of people are more impressed by the user interface than the secret sauce of the product.

User experience is so critical. What seems to be making a big comeback is good old-fashioned customer service. [DevShop is] not just a one-time purchase, I have to deliver month over month. I’ve been frustrated by so many companies recently that I have decided it will not be that way with DevShop.

I pretty much sold everything I owned so that I could workwithout a salary until this thing was launched. It’s great to be able to put your stake in the ground and make sure we invest the time to make a wonderful user experience.

Now that you’re past private beta – what’s coming?

(Editor’s note: public beta is now live)

Thanks Craig, good luck

Thank you.