5 Takeaways from 2016

2016 is a year that I’ll remember more about how I felt emotionally rather than the milestones. The specifics of it I don’t think I will recall well 10 years from now. I think I’ll remember more about how I felt at various points this year as opposed to specific events.

Jami broke out on her own in a big way in 2016 professionally and that’s been a change at home. As weekend and nights became time for shoots and creative projects it was an adjustment but a positive one. The amount of work in terms of volume she produced this year is astonishing.

I traveled less and that had benefits as well as new learnings. My Travel in 2016 was ~50% less than what it’s been in years past.

Throughout 2016, work transitioned from ~70 on the team to ~40. Huge jumps in revenues and customers followed. In some cases it’s never been better but the requirements to get the company to where it is over the year were provocative. The provocative nature of the year caused all kinds of provocation. The end result is new partners, a better business, and focus.

Not the path I would have considered 3-4 years ago but looking back on it I’m not sure if there was any other way to get to where we are. I’m sure 2017 will continue to come with a myriad of positive product changes but I can say confidently that I can see most of them coming and am thrilled to be a part of it.

Clay & Milk
Clay & Milk
Outside of my work I’m trying to get more connected to the community in Des Moines again. One of the ways I’m doing this is working with some friends to spin up a new publication called Clay & Milk focused on telling stories that might not be told otherwise. I’m not involved day to day but have really enjoyed seeing it come together. I think Matt is the perfect editor for the project and Geoff’s experience with Silicon Prairie News will play an important role.

At home things are as busy as anyone would expect. Our kids are hilarious and our youngest, Margaux, seems to learn a new skill daily. I’ve gotten used to stepping on Cheerios and Pokemon as a part of my morning routine. I don’t regularly work 16-20 hour days during the week anymore like I used to and I try to be home for dinner by ~6 on a regular basis. The regular sleep and routine has been beneficial to my productivity. Our kids now have a pet bunny, Penelope, and I still don’t know quite how I feel about that.

I started riding a bike this year to and from work which is the first non-work hobby I’ve had in years except for writing shitty code in my free time. My best contribution on the code side was in a distributed memory project that like many open source projects just doesn’t get enough love. I had my first flying lesson this year and I’m hopeful I’ll be able to continue that into 2017.

I’ve focused on sleeping in 1 bed and working at 1 desk as much as possible in 2016.

When I look at 2017 I feel excited and confident. Not just for myself but for the various teams I work on and for my family. As I look at Q1/Q2/Q3 I see all kinds of things I had always hoped to do but never had the opportunity. Knowing that I get to do those things with people I really enjoy is something I don’t under-appreciate.

Looking back on 2016, here are 5 things that stuck out in my head as the year is still somewhat fresh in my memory.

Do the right thing for the customer

After I sold my first company I questioned whether or not I was a good steward of the company because of how the buyers managed it and ultimately shut it down. There were a lot of learning lessons from that experience that go beyond the act of selling, leaving, and installing proper governance into an organization.

The bigger impact for me was the power of asking myself when a big decision needed to be made, what is the best thing for the customer? 

In a number of scenarios it’s helpful in removing your own emotional view of a situation. As companies grow there are often moments where the consideration of the internal dynamics and of the dynamics of communication to non-customers become a leading part of a conversation. They shouldn’t ever be the leading concern.

Always lead with what’s the best thing for the customer? Dwolla made a dramatic change this year removing our consumer apps to focus on our business products. It meant doing something that I admit was challenging, telling a large group of people who helped us build our company and brand that there are better solutions in the marketplace.

We realized we had too many different type of users on the platforms to service them all well as customers. We need to focus on one or two specific best in class products and put all of our resources behind those.

What products to prioritize, what products to discontinue, how to organize teams and how to hire all get easier when you consider what is the best choice for the customer.

For us, it’s made focusing on our business products and APIs an easy choice.

Inspect what you expect

This is one of the best phrases I heard this year. It came from a friend, Sheldon. Sheldon and I were digging through a number of KPIs and talking pretty candidly about process and who owns what.

One of the discussions wasn’t specific to a situation but just in general, that documents or numbers can be taken at face value. Sometimes data is put into a document as a part of a template to be changed later, sometimes there are mistakes, but more often than not they are 100% accurate.

Taking the time to inspect as much as possible as a part of your habit pushes clarity and correctness across the org. This phrase has stuck with me since and is something I’ve probably repeated a hundred times.

Inspect what you expect.

Tell smart people your problems. See what happens.

Albert told me once that “If you don’t tell a doctor what’s wrong they can’t help you”. It’s true in a number of scenarios. It’s true in healthcare and it’s just as true in business.

I hit a brick wall with a few issues this year and I did exactly this. I made a list of people to e-mail who I thought could help me. I also made a 1 sided ask. I wasn’t trying to waste their time, I needed guidance from people who I could trust who had been there before. The e-mail I sent looked something like this:

Life got flipped upside down. I’m trying to solve 3 problems I’ve never had to solve before and I don’t have a lot of time to do it. I moved back to Iowa and could really use some advice. Could you hop on a call next week?

There were variations of this but I just tried to up front. I want to share some problems with these folks because I really trust them. 10 responses I can recall clearly through e-mail or on the phone looked something like this:

  1. I’ve never dealt with this. Good luck.
  2. Hahahaha. I got nothing for you.
  3. Yeah, I don’t even know what to tell you. I think you’re screwed.
  4. Cool. Here’s the 3 people who I know who can help.
  5. I can’t help but here is someone who I think can.
  6. Do these 2 things and then call me right back. Tell me what happened and we’ll go from there.
  7. Cool. Can I invest?
  8. Can you fly to __________ so we can work on this for a day or something? Happy to help.
  9. Here are 5 intros. Tell all of them the same thing you told me and see what happens.
  10. How are you personally doing?

I got a lot of incredible advice because I just told people the problem.

I didn’t lose respect for those who didn’t or couldn’t help me. I thanked them for the time they gave me knowing their time is valuable and hopefully the next time I see them I can do a lot more listening and less talking. If anything, my respect for everyone on this list grew.

Where I’m going with this is pretty basic. If you need help with something tell people you trust what the problem is and be open to their feedback. People will lend an ear and offer some feedback. If you’ve surrounded yourself with people who want to see you grow personally and professionally, your experience will probably be similar.

Lastly, if you do this the following should be remembered. This is reciprocal. When someone who trusts you writes you an email or sends you a text saying “I’m in a jam, can you give me some feedback on my approach”, it is your responsibility to answer that text and get on the phone with them as fast as possible.

We all need others to help steer us in the right direction from time to time.

quit, or don’t

In every book or blog this seems to just say don’t quit. Some people actually should quit and that’s ok.

It’s ok to quit, unless it isn’t. If it isn’t ok, you don’t quit and you don’t waste anyone’s time by having a bad attitude about it. You don’t fake it and you don’t drag other people down by being dead weight. Swallow the frustration, work through the hard stuff and do the work.

I get that it reads pretty harsh and that’s because it is really harsh and there is no pretty version to this. There’s no easy solution to the times when you just have to suck it up and the only alternative is quitting. Don’t make everyone else drag you through it. Be a leader and lead.

Quit, or don’t. Either way, don’t meddle in the middle. I don’t meddle and it’s always served me well.

Celebrate progress, not seniority.


Focus on what’s good. Celebrate the right things that are happening. At work and at home celebrating progress big and small begets more progress.

Win, together.