Written by: Aaron
Entrepreneurship has taught me a lot. One of the most impactful lessons I've learned on my journey is the power of iteration.
How I viewed iteration before starting a business
I was no stranger to iteration before I became an entrepreneur. In school, I regularly iterated on essays and other assignments. In jobs, I iterated on slide decks and Excel models. Iteration always used to feel like the process of taking something from "unfinished" to "finished." I was used to iterating on something until it was complete and then moving on to the next thing.
An example of the “unfinished” to “finished” mindset: writing an essay
I used to take writing assignments pretty seriously when I was in school. I can’t remember a time where I ever wrote an essay in one sitting. Instead, I would constantly iterate on my essays before turning them in. My essay writing used to follow the same steps - come up with a topic, create an outline, write a rough draft, refine the draft and make final edits.
It sounds simple enough but this process would require a lot of editing and iteration. Part of that was because I wouldn’t allow myself to move on to the next step of my process until I reached near perfection on all the prior steps. I would tweak the topic of my essay if I realized after writing the outline that I didn’t have a compelling enough argument or narrative. I would re-arrange my outline after writing the rough draft if I noticed that my argument wasn’t logically building on itself. After I had the essay written, I would go through it over and over again. Everything needed to be clear. Every word needed to be there for a reason. It was a painstaking process but it worked to help me go from a blank page to a completed essay.
Essays can always be improved, but I had a clear idea in my head of when one of my essays was “finished.” I had a standard and once that standard was met I could submit my essay and move on with my life.
How I view iteration after starting a business
As an entrepreneur, nothing is ever really finished. There is no submitting something for a grade and then moving on with your life. Instead, you are ALWAYS looking for ways to iterate and improve. If you’re just getting started like we are, it’s very unlikely that you’ll get things right the first time. Whether that’s your product, your positioning, your logo or anything else.
And just because something is finished today, doesn't mean it will still be finished tomorrow. So while nothing ever really feels “done,” some things do feel “done for now.” It’s frustrating because you want things to be done so that you can move on, but that just isn’t the way that it works.
It took me a while to adopt the “nothing is ever done” mindset, but once I did I gained a newfound appreciation for the power of iteration.
Where we have iterated in our business
The topic of iteration is almost always on my mind because there are reminders all around me.
I have the first two prototypes of our shoe in my apartment. I look at them every day, which reminds me of all the iterations we have gone through with our product. We received the first prototype in May 2023. We were super excited to touch and feel a version of the product, but we knew that there were certain changes that we wanted to make. We received the second prototype in October 2023. We were happy with certain changes made, but we knew that the shoe wasn’t quite ready for showtime. We received the next iteration in December 2024. This was the first time that we got a wearable and testable pair of shoes. The previous versions were right footed shoes only and were meant more to assess fit than performance. As I write this, we are in the process of making (hopefully final) changes to the shoe based on feedback gathered from our initial testers.
Looking back, it is hard to believe that we went so long between iterations. But when I look at each version of the shoe, I can point to the features that we wanted to see improved. And when I look at the subsequent versions of the shoe I can see how we addressed those initial concerns.
Another good example of where iteration has helped us is our logo. The logo we use today is the third version of our logo. We paid about $15 or $20 for the first version of our logo. It looks much different from the logo we have today because at the time we were planning to create a shoe for former competitive athletes. We knew that we probably wouldn’t use that logo for long, but we wanted something for people to react to and we wanted to start forming a brand identity.
When we pivoted and decided to create a kids shoe, we knew we needed a new logo. We went back to the proverbial well and got another cheap logo. It worked for us initially because we were still pre launch but again we knew that it probably wasn’t a forever logo. We used that logo for over a year until we decided to invest in a full-on rebrand
Do we plan to change our logo from here? No.
Is there a chance that we move away from the current logo? Yes, but only if a new version better reflects our brand identity or resonates more with customers.
Why iteration feels like magic
Iteration starts to feel like magic when I see the progress we have been able to make in different areas. I’ll say to myself - we really were able to go from that to that? Sometimes I am amazed at how much progress you can make by simply iterating, gathering feedback and repeating that process. For example, we started out with an idea for a shoe which turned into a 2D sketch which then turned into a 3D sketch. We used that 3D sketch to sell our first designer on our vision and have him create our first two prototypes. We used those prototypes to create a wearable shoe. We tested that wearable shoe and now we are on the cusp of releasing our first shoe. All because we decided that we would keep iterating until we got to where we wanted to be.
Sometimes it's stressful knowing that certain things aren't quite there yet. Especially when you have to release them or share them anyway. But if you keep iterating, the improvements you see are amazing. You start to enjoy the fact that nothing is ever done. It becomes part of the fun. You become addicted to the process of improvement. As soon as you have an end product, you start to think about improvements you can make for the next version.
Perfect is the enemy of iteration
We haven’t always gotten it right when it comes to iteration for two reasons. The first reason is we have had to learn when to invest early to avoid unnecessary iteration. The second reason is that we have had to learn when to stop iterating internally and get feedback from potential customers.
When you give things more attention and devote more money to them they will improve. That’s obvious. But starting a company is all about allocating the right amount of resources to the right things at the right time. So you can’t focus on improving everything at once. One tricky consideration that has come up for us is whether you pay up and pay once. This would mean paying for a top of the line footwear designer, a top of the line branding agency, a top of the line website designer, etc. The pay up, pay once approach can definitely make sense, but it is also risky. For example, if we had paid for a top of the line branding agency to create our first logo that money would have been wasted once we decided to pivot.
In instances where you haven’t fully validated an idea, I’ve found that it is better to go with a cheaper option while you continue to gather feedback. Our logo and shoe design really took off once we paid for quality, but I’m glad that we waited to invest. I’m certain that other areas of our business will see step change improvements when we invest more heavily in them as well.
Another ongoing struggle has been understanding when good is good enough. You often hear that “perfect is the enemy of good enough.” I think perfect has another enemy - iteration. When your standards are too high, you don’t iterate enough.
One example of this was not getting customer feedback soon enough on our product. We kept making tweaks to perfect our product before having anyone test it. We could have conducted testing and gathered valuable feedback a lot sooner but we let perfect be the enemy of iteration. We spent too much time hoping rather than testing. We hoped for a long time that our product would meet certain performance requirements. We could have put out a non-perfect product sooner to confirm that it met those performance requirements before proceeding with any further tweaks. We were somewhat lucky that our testing didn’t identify any issues that required us to significantly change course.
It sounds silly typing it out but it didn’t feel that black and white while we were in the thick of it. You don’t want to iterate too much but you don’t want to iterate too little either. You need to push what you’re working on to a point where you can get quality feedback to inform your next iteration. But you don’t want to push it so far that you miss out on getting feedback that could save you time and money.
Iteration is an entrepreneur’s best friend
Iteration feels like magic but only if you invest the time, energy and resources into the iterations. Like a lot of things in life, there is always room for improvement in your business. Constant iteration isn’t feasible or advisable, but you should always be thinking of your next iteration.
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