The boring part of startups

As entrepreneurs, building businesses is our adrenaline rush. The same thrill you get racing cars and hunting, we get turning a vision into a reality. It’s hard to understand unless you’ve done it, been part of it, or even watched it first hand. But trust me when I tel you, we really love this shit. 

As entrepreneurs, we move fast, take incredible risks, and operate in environments with almost no certainty when we make decisions. Few days pass without a crisis or some form of chaos ensuing. Within seconds, an entrepreneur’s mood and entire outlook on his or her future can change for the better, or the worse. 

Entrepreneurship isn’t for everyone. It’s a very high risk, and oftentimes, very high reward situation. Those of us that do it understand this. And more often than not, we do it because of this, not despite it. We thrive on the energy, the speed, and the ambiguity. 

The characteristics and traits that we have as entrepreneurs allow us to endure in situations that would break others. But those same characteristics and traits we consider to be strengths can also be our weaknesses, as I experienced this past week. 

A business that I’m currently building had it’s first paying customer this past week. Hooray! Yes, it was a big, frame-worthy moment for those of us working on this business. This was one of those aforementioned, instant moments that changed the outlook for the future of this business in seconds.  

The customer came from a series of experiments we’ve been running for several months. Incorporating the basic tenants of Eric Ries’ popular book, The Lean Startup, we incorporated an MVP and launched a series of experiments. We incorporated the data from the experiments to run new experiments. Each experiment built on the prior experiments. Within several months we’d run dozens of them and, lo and behold, we got an actual paying customer. 

Up to this point, I thought I’d done everything right. I’d learned so much along the way that I iterated to success. All signs pointed to doubling and tripling down on the strategy. We are on our way to exponential growth. 

I could see it all so clearly in my head. 

The problem is, from the outside looking in, it’s not as easy to see. In fact, it’s pretty easy for people that aren’t involved in the rapid movement of the day-to-day in a startup to have the perception that I just spent several months and thousands of dollars to get a single customer to give me $125. Those of us with the broader vision know otherwise, but by a lot of (very fair) standards, that’s a failure. 

So, as entrepreneurs, our job is not only to turn our vision into a reality, but to ensure that important stakeholders - like investors - understand the vision. It is our responsibility to keep them engaged and informed along the way. This goes against what many of are wired to do, which is, to do. We like to do shit, not talk about it. We like productivity, not activity. We like story making, not story telling. 

And that is where our strengths are also our weaknesses. 

As entrepreneurs, it is important to remember that even if stakeholders understand our vision, they may not share the same degree of passion that we have for achieving it. If they did, they’d be doing what we are doing. Generally, they are investing a great deal of trust (and oftentimes, a lot of money) into us to execute. And in return, we owe it to them to provide honest and candid assessments on progress, and we owe it to them to do so in a way they’ll understand with absolute clarity. 

If progress reports and presentations to document what you’ve been doing sound like torture tactics, I’m with you. This is not what drives us. But it must be done. So, it’s incumbent upon us to make it as easy and efficient as possible. We have businesses to build after all. So, here are a few tips I’ve come up with to make this boring part of entrepreneurship a little bit easier and a hell of a lot faster: 

  1. Track your activity and automate it. I use Workflowy, which is essentially an incredibly dynamic to-do list that allows you to create multiple layers on multiple tasks and organize them. Here is a video of it in use and you can get it yourself here. The use of hashtags and ampersat symbols allow me to filter activity any way I want and I’ve found this to be the most effective way for me to organize my brain, which is no easy task.

    Workflowy also serves another important function: It tracks what I’ve done and sends me a daily email summarizing what I did the day before. These emails and reports serve as an activity diary on autopilot. I save the emails to a folder and when I need to recall details of experiments we ran several weeks ago, which can feel like years ago in a fast pace environment, it’s all there for me. This is helpful when you need to summarize what you’ve done over the past few weeks or months for other stakeholders.

  2. Document learning. The product development process I’m using relies heavily on experiments and iterative improvement. Since we are in the digital space, we can run experiments and measure them at rapid speed. It's not uncommon to run multiple experiments simultaneously. This is all well and good, but the data and learning can pile up quickly and when it’s time to demonstrate to stakeholders what I’ve done and what I’ve learned, it’s overwhelming. So, we have a simple form to use with every experiment that contains four sections: Date, Build, Measure, Learn. The basis of measurement is borrowed from the Lean Startup and I like it for its simplicity.

    For “Build,” I summarize what the experiment is. What are we testing? Who is our audience? What is our hypothesis? How are we testing it?

    For “Measure,” I write what we intend on measuring. When we execute on the experiment, I complete it with the actual data.

    For “Learn,” I write what we learned from each experiment, what surprised us, and how we think we’ll use the findings.

    This process creates a sense of order out of what looks like chaos and it makes it incredibly easy to put together summaries of what we’ve learned when metrics (like revenue and users) don’t tell the story yet.

  3. Be proactive in communication. Investors, employees, and other stakeholders rely on me to give them critical information about the business and thus, peace of mind. If I wait until they are concerned and asking questions, I’ve waited too long. As a rule of thumb, I simply ask stakeholders how frequently they want to hear from me with updates and progress reports. Then I communicate slightly more frequently than that. As I do with other activities, I block time on my calendar to do it in advance of when I need to do it. I don’t wait for a “good time” because there never seems to be one to write progress reports. I put it on my calendar and stick to it.

These a few things I do to provide a bit of structure to our intentionally chaotic environment. My experience has been that the processes we have in place to help us provide clarity to stakeholders also help provide clarity within the team. That ensures our tactics are helping advance the strategy to turn our vision into a reality. So, we all win. 

Have you found tools or built processes that provide some clarity and efficiency in communicating with stakeholders? I’d love to hear them if you have.