March 2015: Reflections on Being an Entrepreneur


No office. Work when you want, from wherever you want. #Nomad for life. Sounds groovy, doesn’t it? Why, yes, I happen to agree. I’m a few weeks into my entrepreneurial adventure as co-founder of Retrium, and like clockwork, the winter grays are in the rear view mirror. It’s 75 degrees out and sunny. The coffee is strong, the music is playing, and spring is here.

As I continue to adjust to the daily #startupgrind, from time to time I plan to share some insights into what bootstrapped start-up life is really like. For those of us who live outside The Valley, and especially for those of us who live in a “suit city” like Washington, D.C., being an entrepreneur comes with certain stigmas and assumptions. What is it like working without an office? How do you know what to do all day? Can you actually make money being an entrepreneur? That, and more, coming your way. These are my random thoughts and reflections, so read at your own risk Smiley

Lessons from March 2015 (Month 1)
The open-ended nature of building a business is simultaneously empowering and exciting as well as confusing and overwhelming.

There is so much to do when building a business from scratch. We have to build a website, build a product, build a customer base, build a marketing plan, build a business model, build, build, build, and build some more. Since there’s only two of us (myself and my technical co-founder, Ryan), there’s a constant nagging sense that we aren’t accomplishing enough on a daily basis because there’s just so much to do. At the same time, the fact that on any given day I can work on anything I want is incredibly empowering and exciting. It’s a strange dichotomy that, I suspect, will persist for a very long time.


Working in the same physical location as your co-founder is both challenging and invigorating at the same time.

As a cash-strapped startup, we have no office space. Some days, Ryan and I choose to work separately from our homes. Other days we decide to meet and work together out of a coffee shop. As a social guy, I thought that I’d prefer working with Ryan from the same physical location. Sometimes I do. But working together also presents challenges of its own. It can be distracting. It can be far too easy to disrupt each other. At the same time, being together enables you to easily share the joy you get from tweets like this:

It feels great.

I finally feel that I have control over my own life. I no longer have a one hour commute every day to and from the office. I no longer have to request days off to take care of a sick child or to celebrate a holiday. I no longer feel like a bad employee when I have to go to a doctor’s appointment in the middle of the day. At the same time, I wake up excited to start working. The day goes by in a flash because more often than not, I’m in the flow. Assuming the whole “I need to make money” thing solves itself at some point, this lifestyle is far superior to the 9-5 office job.


Friends and family are genuinely interested in what you’re doing at work.

“How’s work going?” used to be a relatively empty question. Sure, I could give an answer, but with the exception of my spouse, my parents, and perhaps a few others, no one else really cared that much. That’s no longer the case. Friends, family, former colleagues, and even random people I meet genuinely want to know how Retrium is doing. It’s kinda cool.


That’s it for this month. Now, back to work Smiley

Why Retrium?

This past week, I told my boss at work I’d be quitting my job to be the co-founder of a startup, Retrium. Over the years, I’ve had plenty of ideas — some more successful than others — but I never quit my job to work on them. One might reasonably ask: why go “all in” on this one? In other words, what makes Retrium different from my past entrepreneurial endeavors?

Good question! Here are three reasons why I believe Retrium has a really great shot at becoming a very successful company:

1. Broader Market Forces

Retrium is a toolbox of facilitated retrospective techniques built specifically for distributed scrum teams. If you’re not in my target market, that might sound like a jumble of jargon, but it sits at the intersection of two powerful market forces:

  1. The increasing popularity of remote work and distributed teams
  2. The incredible adoption rate of agile and scrum within the software development community

Let’s start with the first one: the increasing popularity of remote work and distributed teams. According to ESNA, 20% of the global workforce telecommutes. More anecdotally, we’ve recently witnessed the incredible popularity of websites like Nomad List, which provides information about the “best cities to live and work remotely”. We also have lengthy crowdsourced lists of startups with a distributed workforce. In short, companies have begun to realize the importance of hiring the best talent, regardless of location. This trend is only going to continue as technology gets better and better at reducing the friction of a distributed workforce.

The second market force is the incredible adoption rate of agile and scrum within the software development community. The jury has decided, and agile has won. What began as a simple manifesto has turned into powerful force that is helping teams produce better software, faster. This is true, of course, for the startups of Silicon Valley, but it’s just as true for the multinational enterprises of New York and the nonprofits of Washington, D.C. After all, who wouldn’t want to be more agile?

Clearly, there are plenty of pain points left to solve in both of these relatively nascent markets. Retrium solves one of them.

2. External Hooks That Naturally Reduce Churn

The biggest challenge to the sustainability and profitability of any SaaS company is customer churn. The simplest definition of churn is “the rate at which customers cancel their subscription.” Why is churn so important? For each customer that cancels their subscription, a company has to find another just to maintain current revenue. If a startup wants to grow, then its customer acquisition rate has to be greater than its churn rate. Clearly, the higher the churn rate, the harder this is to accomplish.

One of the best ways to reduce churn is to have a high level of user engagement. After all, users who are engaged with your product are less likely to cancel. One of the things that excites me most about Retrium is the fact that it has a high likelihood of having extremely low customer churn.

Retrium benefits from something I call an “external user engagement hook,” which is something that encourages customers to use your product from outside the product itselfRetrium’s external user engagement hook is the scrum framework, which requires teams to run retrospectives on a regular — and frequent — basis. The hope is that every time a team needs to run a retrospective, it will be reminded to use Retrium. Having an external user engagement hook can be an incredibly powerful driver of low churn, and it makes me confident in Retrium not only as a product, but as a business as well.

3. I’m Passionate About It

One of the worst mistakes a founder can make is to start a company in a market that he or she is not passionate about. Popular culture would have you believe that founding a startup will lead to a glamorous life full of parties and ritz. The reality is quite the opposite — startup life means hard work — really hard work. As a result, founders of startups can burnout quickly, especially those who start companies in markets they aren’t personally passionate about.

As for Retrium, I’m fortunate that it’s at the intersection of two areas I’m truly interested in: agile software development and distributed teams. In fact, Retrium itself is being built with these concepts at its core. Not only are we using the scrum framework to develop Retrium’s code, but we’re also a fully distributed workforce (we have no office).

Looking Forward

None of this means that Retrium will, in fact, be successful. Most startups fail, and it’s far too easy to live in a positive echo chamber that can lead to overconfidence in your idea. Nonetheless, I truly believe the future for Retrium is bright. I’m excited to get going.

Coming soon: a post describing how I got the confidence to quit my job and start Retrium. I’ll give you a hint: Lean Startup.

Excited to announce Retrium — distributed retrospectives made easy

For the past few months, I’ve been hard at work in my spare time on a startup in the agile/scrum space. Along with my co-founder, Ryan Detweiler, I am very excited to reveal it to the world (or, at least to those select few who actually read this blog!). It’s called Retrium — and it’s a tool that makes sprint retrospectives easy and effective for distributed scrum teams.


Here’s why we’re building it. If you’ve ever worked on a team that uses the scrum framework, then you probably know all about sprint retrospectives. Most likely, you’ve been exposed to retrospective facilitation techniques like 4Ls, Lean Coffee, The Wheel, or Mad/Sad/Glad (no? you should try them!). Here’s the problem: all of these techniques require flipcharts, sticky notes, markers, and other physical tools. While that’s fine and dandy for collocated teams, geographically distributed teams are left out in the cold. That’s where Retrium comes in. We want to bring the power of these retrospective techniques to distributed teams.

Here’s what it is. Retrium is a set of super-simple interfaces to some of the most popular retrospective techniques. It is completely device independent, so you can use your phone, tablet, or desktop to participate. Retrium is also a facilitator that guides you through the retrospective itself. Don’t know how to run Lean Coffee? Don’t worry, Retrium takes care of that for you. Finally, Retrium doesn’t try to do too much. It isn’t intended to replace video conferencing, it merely complements it. In fact, we recommend you run a video conference while you run a Retrium-powered retrospective.

Here’s our timeline. We are aiming to launch our MVP in the summer. In the meantime, in good lean startup fashion, we have a pretty landing page with a place to enter your email if you’re interested in hearing more.

So that’s it. If this resonates with you, reach out and get in touch! Please email me so we can schedule a time to chat.

Retrium — retrospectives made easy.