Burn it all down

I don’t generally take time away from work to attend conferences. I like digging in and making progress on the work more than spending time talking to people about it. However, I went to EntreFest to reconnect with the incredible startup community in Iowa and friends I made during the Iowa Startup Accelerator.


(Photo credit: @pennerj via Twitter)


I got exactly what I wanted – a super recharge of energy and enthusiasm for my work.  And that would have been enough. Truly.

Something else happened though. Something unexpected.

I spent three days talking to people about their projects and ideas and startups. I talked to several people who are just starting out. Maybe they went through Startup Weekend or Venture School and are still in the early stages of customer validation, prototyping, and lean testing.

And I asked them questions, riffed on their ideas, helped them brainstorm, and could picture paths they could take to make their product a success.

I envied them. They had so much possibility.

So many options for how they could move forward with their idea. They could really use the Lean Startup methodology and do it right, testing riskiest assumptions along the way, building MVPs and iterating to get them right. They could work fast. They could fail with tiny experiments or fail in big, “this is a no go” way and it would be ok.

Wow, to have that flexibility and ease. To have that ability to build just the right thing.

I didn’t think I had those options.

I’ve been working on the Kids Calendar for four years. I’ve built a product that a lot of people use regularly and appreciate, but it’s not really the product they want. It’s what I was capable of hacking together as a non-technical hustler. It represents the very best of my ability to duck-tape together third party code and pray it all works together correctly.

And because we have users who count on us and paying customers who expect the products and features we promised, we also have a certain way of doing things. We’ve got systems and procedures. We’ve got spreadsheets, how-tos, a CRM, and invoicing systems.

Since doing customer discovery in the ISA, I’ve known the Kids Calendar should have other features and operate differently than it does. Those customer interviews were great for helping me see what the Kids Calendar could be if we weren’t limited to what I personally could build.

But I was still hamstrung by the old way we were doing things.


old user stories

Even as recently as three weeks ago, I attended a day workshop on Agile user stories. I mapped out all of the things the Kids Calendar does – both in terms of product and how the business functions, including sales, marketing, and support.

Without even thinking about it, I described our current reality and pictured how great it would be when we had improved technology that let us do what we currently do, but faster and more efficiently.

Turns out, all of this time working with our functional MVP has led to a suffocating amount of technical and operational debt.

Even when I knew we needed to build something different, I couldn’t really imagine it.

Attending EntreFest helped shake me out of my rut. 

At the end of the second day, I wrote myself a note:

“How would I launch the Kids Calendar today if we had no technical OR operational debt? Would it be worth it to push the pause button and restart?”

Today, I’m back to work in my new office, prepping for my interns who start tomorrow. I’ve put together a cross-functional team of developers, designers, and marketing. We’re starting the summer with Google Ventures’ 5 Day Design Sprint, and I needed new user stories to describe what we’d be designing and building this summer.

So I burned the old way to the ground.

With some blank sheets of paper, I worked through the core UX questions. Turns out four years of working on this problem has given me lots of domain knowledge around what we need at a basic level. In just a couple of hours, I was able to completely re-envision how we organize, manage, and display content while keeping true to our value proposition: comprehensive, local, relevant, constantly up-to-date.

The old Kids Calendar was built on the question of “what can I personally create using pre-made tools?” I spent the morning asking myself “what’s the best way to solve these problems?”

The-Holstee-Manifesto excerpt

What resulted was a far superior solution. Not only is the functionality/feature set better, but the user interface will be more cohesive and easy-to-use. And… I was able to see solutions for two of my biggest, intractable “how do we scale this thing” challenges.

Figuring out what the Kids Calendar 2.0 will be was bigger than just throwing out old code. I had a lot more than technical debt. I had four years of “this is how we do things around here.”

When my intern team starts tomorrow, they get to be a part of the construction of a completely new system. A new company really. One where we, too, can design and build using Lean techniques.

I’ve got a lot of assumptions about how this new product should operate and what our users and customers will value. I can’t wait to test them.

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