Let’s Divorce – Working to increase happiness amid this emotional process.

I spend a lot of time thinking about my legacy and what that means. It impacts the way that I approach my utilization of time, what projects I want to work on and who I prioritize spending time with. I would like to think that every decision is run through this legacy filter, but it is more correct to say that it’s a guiding light.

Using this approach to decision making the past couple of years has been interesting for many reasons. One of those reasons being a decision to start a company with a couple partners. The baseline for my decision to join was an alignment in how we were going to approach building a company. There was a product that we wanted push forward, but we also shared a desire to help others take their business ideas and launch them into the marketplace. We knew it would take time to figure it out and were interested in taking multiple shots.

One of the guiding lights in my personal life is to work on projects and start businesses that can help lead individuals to happier and healthier lives. I am most fulfilled when this means helping people reach the edges of their personal performance potential.

I am also committed to the idea that helping people find physical health can establish behaviors that supports their emotional, spiritual and mental health.

All of this is context to share the most recent project that I have been working on. About ten months ago, my team was approached with an opportunity to help create technology that would support people getting a divorce.

Internally I asked, “How can divorce be something that creates happiness or health?” Everything I have ever read about divorce is that it is stressful. In fact, it is often cited as one of the most stressful events in a person’s life, right up there with the death of a loved one and having a child.

A little more context for the story.

In a somewhat cruel twist to the plot, it was also during this time that I was finalizing my own divorce. After several years of knowing my marriage was struggling, two and a half years of therapy and then almost a year of slow progress on getting the paperwork completed, I was becoming a divorcee the same month that this business proposal came.

Through my divorce, one of the observations that I consistently had was that I was a lucky man. During the entire process, my ex wife and I got along quite well. We did not fight over possessions and there were no battles about who was wronged the most. We continued to understand that it was a difficult phase for both of us and worked to make it less painful. I knew that this was rare. Our therapist commented many times that he couldn’t believe how well we treated each other.

To completely understand how surreal it was, when we started talking to recently divorced individuals about their experiences, I asked my ex if she would be willing to be interviewed. She was very unselfish and agreed to meet with my business partner. The day they met happened to be the day we got our decree back from the court that our divorce was final.

Back to the story of the product.

When we sat down and talked about the vision for the product, I started to become more intrigued. The story was not about how we could automate divorce, make divorce easier, or make divorce cheap. The discussions were about how we could make divorces less contentious, less litigious and more cooperative. We began planning out how we could begin making progress in this direction and I started talking to recently divorced individuals.

In these discussions, I learned a lot about the experience that others had gone through. There was a lot of fear regarding what had to be done. This included relationship issues and communication with their spouse during the process. There was a large amount of fear about how to go through the process because information was difficult to find. Then there was the realization that financial statuses were going to be impacted, which included the division of assets along with the cost of attorneys.

When you put all of these fears and anxiety on top of the sadness, stress and broken hearts, it becomes a very difficult time for everyone.

I never talked to anyone who said that they got married with the anticipation that one day they would get divorced. Some shared that they got married and looking back probably should not have (which I guess might seem obvious at this stage), but hindsight is 20-20. The point being that no matter what lead to this place in the individual’s life, regardless of the circumstances, divorce is never easy.

This is the observation that allowed me to become more invested in the online divorce platform, LetsDivorce.us.

If I could find a solution that was able to eliminate divorce, I would work on that today. But when you look at the divorce rates across demographics and throughout the U.S., it’s pretty clear that as long as marriage is around, divorce will be also.  

I accepted that this was the reality. I had to also admit that the amount of lost joy and unhappiness experienced was significant. If there was a way to make divorces better, than I could significantly improve people’s lives. There might also be an opportunity to help couples start working through the process, with the support and guidance they need, which leads them to reconciliation?

How does a better divorce happen? That is what we’ve committed to work on. Today, it is starting with one piece that many of those we interviewed identified as a high stress component. And I’m happy to share that The Johnson Law Group is the first customer who is going to be utilizing the LetsDivorce.us solution to help make divorce better.

Expect Rejection: Learning from every ‘No’ in sales and online dating

There is a new podcast by Reid Hoffman (founder of LinkedIn) called ‘Masters of Scale’. It is a master class in startups with many of the top founders and CEO’s. The guests include successful individuals such as Brian Chesky, Sheryl Sandburg, Mark Zuckerberg and Eric Schmidt. If you only have time to listen to one episode, having listened to all of the episodes to date, my suggestion is listen to the Reid Hastings episode. It is the story about how he created culture at Netflix after learning hard lessons at Pure Software. I’d also recommend that you go view the ‘culture deck’ that they talk about within the episode.

As a bonus learning tool, they published an episode with Tim Ferriss. In that episode, Ferriss takes all the lessons and provides commentary and insight. He pulls together a “10 Commandments of Startup Success”. It was listening to the discussion around the first commandment that I realized that I’ve been getting an entire PhD in startups over the past eight months. I say it’s my PhD because I am now on my fifth attempt at creating a viable and sustainable company. Three of those companies are still in operation and at very different stages, so I would like to focus on Upper 90 and what I am learning through it today.

For context, Upper 90 is a development and sport science company at its core. We have a product that we are trying to bootstrap called PyCoach. PyCoach is an athlete monitoring platform that provides a window into an athletes readiness to perform, for coaches and performance staffs. In addition to the saas product, we provide data management consulting services for colleges and universities that are trying to better utilize data on their athletes.

Back to Tim’s first commandment of startup success,

“Expect rejection. But learn from every ‘No’”

This is something that I have heard successful startup founders and mentors talk about in the past, however I do not think that I have been in a mindset that allowed me to learn from rejection. Rejection was something that hurt a little too much and dug a little too deep for me to ever have a clear and positive reaction.

If you would have asked me about this in the past, I would have likely said that I was able to understand and learn from rejection. However, I had confused the difference between “rejection” and “failure”. There is another common saying in startup culture: “fail fast”. While I absolutely hate failing, I have been able to mature to a point where I understood that failing in the right ways can often be positive in the long term. I drew upon my knowledge and experiences in athletics to help me get to this understanding. In athletics, I have always been able to use poor performances to be the foundation for better performances in the future. The striving and self-competitive mindset becomes addictive. For example, I recently started to rock climb. I am absolutely horrible at it, however I know with each attempt I can learn and grow.

The “fail fast” paradigm isn’t what is meant when the commandment “Expect rejection” is shared. It has taken me awhile to work through this, plus a decent amount of therapy, but I now understand that a rejection isn’t (or doesn’t have to be) a failure. As I look at the two, I see failure as an outcome. In many cases it’s a binary outcome (the easiest to learn from), but it doesn’t have to be. Rejection is more of an interpretation by someone else regarding what you are offering and their desire and need for that offering.

This seems very nuanced, I understand the confusion, so let me share a couple ways that I am currently learning from rejection, but in ways that I don’t believe is failing.

Online dating as a window into rejection:

I’ve been talking to others for awhile about what it’s like to date. I was never good at it the first time around, so it’s pretty anxiety inducing to think about trying to do it again 15 years later. It’s even more challenging when I realize that I don’t have too many settings where it makes “discovery” possible. This is when I started talking to my friends about their successes. I learned that several friends met their partners on Match, two meet theirs on OkCupid and another friend has been using the Bumble app. Inspired by their stories, I first joined Bumble, a week later I signed up for OkCupid and after brief periods of time on those platforms, I’ve moved on to Match and Tinder.

What I’ve come to learn through experience and reading of others, is that volume of interactions is essential for men to be successful. It seems very counter intuitive to my long term romantic notion that you just meet someone as they walk into the room and you know they are the one. The idea of sending out dozens of messages to get no responses, then feel empowered to carry on, is difficult. Whether I want to admit it or not, there’s at least a small feeling of rejection every time I send a message and hear silence.

A reality of using the platforms is that it’s unclear why no response is given. My first interpretation is that she read my message, reviewed my profile and gave the hard pass. However, it’s a story I’ve made up. At least on Match, I realize now that there are profiles that are active yet the person never uses. So another possibility is that she never saw the message. The uncertainty of the situation makes managing the process that much more emotionally challenging.

The value, for me, of using an online platform at this stage of understanding how to date in a modern world, is that the individuals on the opposite end of the conversation are mostly unknown. I do see people I know on the platforms and for the most part I do not engage in conversations with them, as rejection from someone I already know might be too difficult.

The main lesson that I’ve learned, that applies to this discussion, is that there are many stages along the dating path. At each stage, the opportunity for rejection exists. While I have not experienced anything beyond the initial stages of communication to this point, I anticipate that the pain that comes along with rejection also increases with each step forward. As commandment number one suggests, “Expect rejection, but learn from every ‘No’”. If rejection is not a failure nor a binary outcome but an interpretation of your offering by someone else, what can I learn from rejections in the dating world? Here are some thoughts:

1. Did the person communicate values they desired, that I did’t offer? For example: family, political or religious values.

2. Did she want someone that has the personality that I possess? If not where there early signs?

3. Did I communicate my values and desires clearly upfront? Is it possible to improve the way I represent myself better?

Startup sales as a window into rejection:

I am not a great salesman, but in the initial stages of most startups , founders find themselves taking on roles by default. That is where I have found myself many times over the past eight months. Whether it be selling PyCoach to colleges and universities, or selling our consulting services, I have come to realize that you can take all the lessons I just shared about online dating and transpose them into sales. In fact, it’s not uncommon that I find myself sending sales emails to a college coach one minute and then responding to a message on a dating app the next. The majority of messages I send out, even to a coach I have a direct connection with, receive no returned response.

In the sales process, I have had several situations where the communication back and forth start to create feelings of shared vision and alignment. In at least two of those situations, what felt promising and potentially life-changing (for a small bootstrapped startup like us anyway) resulted in eventual rejection. It hurt. What are a few things that I learned from those hard “No’s”?

1. I got a little caught up in the potential sale, even when the customer didn’t exactly fit our targets.

2. I struggled to communicate our value prop in a clear manner.

3. I lost track of the stage of ‘courtship’ we were on, partly due the timing and impending decisions being made.

Some final thoughts on rejection:

Everyone goes through rejection. Going through the process of getting rejected doesn’t mean it’s a failure, however that also does not mean it won’t be a little painful. When I listened to the Master of Scale summary episode with Tim Ferriss, I initially was not sure I believed that a lesson about rejection should be commandment number one. I do now. If not number one, than at least in the top three, because without being able to manage rejection well a founder will never possess several characteristics I believe to be critical:

1. Resilience

2. Self-awareness

3. Humility

If all of this is true, how does someone practice getting better at handling rejection? There are workshops targeted to founders that need to learn about product development, financial processes and fund raising, however I’ve never seen a weekend seminar focused on rejection. My guess is that handling rejection is something we are expected to know, or that we were taught how to handle it at a young age (which doesn’t seem likely, especially in today’s environment).

I believe that we should practice and prepare for important things in our life, to which I’d encourage a founder to not wait until their first big deal to find out how they’ll react to getting turned down. If you are not ready or in a position to face consistent rejection that comes along with online dating, my current training ground, I’d recommend you start small and with something that is very low stakes.

Noah Kagan created the coffee challenge several years ago as a way to get startup founders exposed to the feeling of being rejected. If you haven’t completed the challenge, I’d encourage you to start there. If asking for 10% off your Starbucks is difficult, how will you ever face the risk of rejection associated with your business contracts worth thousands or millions of dollars?

By doing the challenge you’ll learn a lot about yourself, including whether you are an ‘asker’ or a ‘guesser’. I’m 100% a guesser, which is why learning about rejection is so fundamental to my growth as a person, startup founder and romantic partner.


1. Master of Scale Podcast

2. Netflix Culture Deck

3. Tim Ferriss summary episode of Masters of Scale

4. Noah Kagan’s Coffee Challenge

5. Brene Brown’s talk on vulnerability (which is a requirement, imo, to face rejection)

Being focused and productive within a distracting and noisy day

In a world that is full of distractions it can be challenging to find the space to work uninterrupted. The physical space or mental space. To be effective and have a high work rate, I find that it requires consistent stretches of time that is interruption free. This is especially true when I am writing or programming. Since the Awesome Inc Web Development Bootcamp started, I have worked at fine-tuning how I can achieve such an environment. At the moment, I have found a system, that works for me. Here is my current process, I hope that it gives you some ideas. I would love to hear your process, if you are trying to work on your productivity.

Taste, Smell.

The first step I take in creating the right environment is to think about all the senses and how they can impact the work. I do not normally have to worry about taste or smell, however I do like to sit in A Cup of Commonwealth to write. The smell of coffee shops is wonderful, plus I tend to drink a lot of coffee and their coffee is much better than anything I ever brew myself.


What about the distractions created by other customers? When I am at a coffee shop, I almost never program. I instead spend that time writing (as I am right now). The advantage of  doing this is that I can close my eyes and type without looking at the screen. This is a trick that I picked up from Luke Murray when he came and spoke to the bootcamp. The idea being that when you look at the screen while you write, your mind is on constant edit mode. It causes your writing to be slower and overly critiqued. On a first draft, the idea of being overly critical is not a good one. By closing my eyes to write, I can just work on letting the thoughts make it to the screen, I then go back and edit at least once, sometimes more. (This post is pretty basic, so it’s had one edit). The only distraction I have with this part of my process is that I can begin to feel self conscious as I type in public with my eyes closed.

When I need to program, I have to be in a different setting to optimize things visually. I have not yet figured out how to effectively and productively program with my eyes closed (still working on the eyes open programming). I also love to have multiple monitors when I code. That way I can have the editor (currently using Atom) and terminal open on one screen, with another screen free to run a browser.

To minimize the visual distractions, I also turn on the mac’s ‘Do Not Disturb’ setting, along with closing any messaging applications such as iMessage, Slack and Riot. Having the little notification number go from zero to 1, or 1 to 5 becomes very difficult to ignore when you are trying to be focused.


I can be distracted by visual pollution, however I have found that sound is a much bigger problem. In the coffee shop it is the sound of customers ordering an interesting drink, or the random conversation by strangers that you want to avoid but don’t seem to be able to. In order to fix this I always try to write and program with headphones on, listening to Spotify. Here are some of the things I have done to optimize this:

1. I used to use my standard Apple headphones, but I often found noise leaking into my bubble. I ended up getting some Beats Headphones, which was a major improvement. At some point, I could see the investment in some noise cancelling, over the ear headphones being another step forward.

2. I listen to the Spotify ‘Focus’ channels. I change it up at times, but my three favorite channels tend to be “Chill.Out.Brain”, “Deep Focus” and “Mellow Beats”. I use these channels because they are background tracks to my work, which do not include song lyrics. I have tried to use normal channels with music I like to listen to, however the right song can really ruin my concentration. I can be writing a post about productivity hacks one minute, then be taken to an old dirt road back home the next and be completely lost. That doesn’t happen with the tracks on the focus channel. A second upgrade I recently made was to start paying for Spotify Premium. I found that the commercials were interrupting my concentration, so for $10 a month I solved that issue. I listen to Spotify at home on my Amazon Echo and when I run on my iPhone, so $10 a month is amazingly cheap, in my opinion.


The only requirement that I have in regards to touch, is making sure that the chair I am sitting in is satisfactory. I don’t require a super comfortable seat, but something that is comfortable enough that I can sit for 25 minutes at a time and feel like I’m not being tortured is helpful.

Managing time and focus.

No matter what type of environment I have created to write or program, I can only maintain focus for so long before my mind begins to drift into another place or time. This is something I used to fight, but today I just accept that it is human nature. I know that there is a decent amount of research on the topic. For performance in athletics, I used to study all I could on getting into a Flow State (read ‘Rise of Superman’ if you are interested). I would love to say that getting into a flow state, where time disappears was a common practice, but that has not been reality. Therefore, I take advantage of this understanding and utilize it.

I use a pomodoro timer to manage these “focus” and “relax” periods throughout the day. I have my timer set for 25 minutes of focus, with 5 minutes of break time. This has been effective for me. Thomas also uses a pomodoro timer, which I believe he has his set to 15 minutes of focus and 5 minutes of relaxing. I would encourage everyone to test out using a timer and see how it works for them. Once you have determined if using the timer is something you want to stick with, begin to test different intervals and find where you feel most productive.

A tip that I have learned from Thomas, has been to use that 5 minutes of relaxing to completely shift the type of activity I am doing. When I am programming, I am thinking logically and trying to solve puzzles, therefore I try and switch to something that is less analytical. During the bootcamp, I would stand around and talk programming during breaks with other students. I didn’t think about it at the time, but it didn’t give my mind the space it needed. I have completely copied Thomas’ approach, which is to read something different during the breaks. I am currently working through ‘Zen and the Art of Motorcycle Maintenance’.

What have been the benefits of working in this way:

I don’t use this process for all of my work. For example, I do not always use a timer while I am answering email or responding to various networking pings. I use this process when I have work to get done that needs focus, consistency and progress. I have enjoyed the habit of using the timer, because it creates a process that I can repeat each day. It makes the days that I don’t feel like sitting down and programming or writing much easier to initiate. In many ways, it is similar to the run/walk strategy that I have used to coach some of the runners I have helped finish marathons. A task is much easier to start when the challenge is to run 2 miles (or whatever your splits are), then take a break and reassess, compared to getting started with the task of running 26.2 miles. The same is for my 25 minutes of focus.

The other benefit to this process is tracking my productivity. By using the pomodoro timer, I have a log of how many cycles it takes to work on a project. For example, I’m 2 cycles and 20 minutes into writing and editing this post, completed over two days. This type of tracking allows me to manage how I allocate my time and look back on how it matches what my intentions are. To continue with this writing example, I have a goal to do some personal writing for two pomodoro cycles each day (a total of 1 hour). I can see that this week, I have only accomplished it 2 of the 5 days.

Creating an environment where you can be successful, productive and focused can be a challenge in a world designed to distract you. Hopefully some of these ideas are helpful, if you have similar needs for your work environment that I have. If you have other ways to improve upon this practice or processes, I would love to hear them.

Designing for health: Balancing user distraction and engagement.

What are the guiding principles that product managers, designers and developers need to consider when it comes to user engagement and attention distraction?  I find this to be an especially critical question for those of us who are focused on making a user’s life happier and healthier. The dilemma is trying to balance the two different outcomes we hope our products achieve:

1. A user engages with the product consistently.

2. The product helps the user optimize their lives by empowering them to make choices that support their health behaviors and decision making.

These two outcomes can be challenging to achieve in perfect harmony, as highlighted in a recent discussion between Jason Calacanis and Adam Gazzaley on the podcast This Week in Startups. In the discussion, Gazzaley,  author of “The Distracted Mind: Ancient Brains in a High-Tech World”,  shares his research on distraction and its impact on human behavior. The most interesting conversation was when they were talking about social media usage, the distractions that it causes and the impact it can have on mental health. My understanding was that too much distraction, without awareness and guidelines, can lead to increases in anxiety, depression and other mood imbalances.

Understanding how to engage and gain the attention of a user is one place a user’s health needs to be considered when we are developing our products. If we know that constant distractions are potentially detrimental to a user’s health, are we prepared to make design decisions that engage our users in a healthy way? Even when we understand that we should filter creative decisions through this lens, do we design the applications so each user has the freedom to set up the level of engagement they want, or do we remove distractions from the user experience completely? These decisions clearly require careful thought within the context of each development process, however having an ethos that underpins your development philosophy is essential.

The reason that this ethos is critical, is due to the fact that at some point you will be faced with the observation that users are not engaging with your product as much as you (or your investors) would like. In these situations, how will you respond? If it is in your development ethos to prioritize user health over user engagement, it will help you continue developing a supportive and effective application.

The discussion of notifications and distractions is not one sided.  Having some distraction does not necessarily mean the product is only negatively impacting the user’s health. The optimistic side of this product design decision making, is that when an application can engage a user at the right moment in time, it can support a user’s goal to live healthier. The insertion of an appropriate ‘trigger’ is part of the theoretical foundation of B.J. Fogg’s behavior change model. When our products can provide a trigger to the user at the right moment, paired with a behavior that is within their ability and given adequate motivation, then our products can become a positive tool for change.

In the interview, Gazzaley said multiple times that one of the best behaviors an individual can have to combat negative impacts of distraction is to engage in physical activity and exercise. One positive strategy I have seen in multiple technologies and applications is to provide a nudge towards movement precisely at the moment a user will find themselves getting ready to read their Facebook, Twitter or email inbox.

I conclude with a question targeted at myself and others creating products that desire to improve a user’s health and happiness:  How are we defining the amount of distraction and engagement required by a user, as we design our products?

My Startup Weekend Experience

This past weekend I participated in Startup Weekend Lexington. It was an amazing experience, where I walked away with a new understanding of myself as ever aspiring entrepreneur. Now that I have been able to catch up on sleep, here are my key take-a-ways:

Lesson One: 

A lot can be accomplished in three days.  I have had business ideas in the past, along with the many ideas that I had to expand business when Endurance Base Camp was my full time focus. The issue with those ideas was that I rarely committed to an idea, in a way that allowed me to understand if it was valid. I would try to work on it in the spare moments, which meant starting and restarting on a project. What I learned this weekend was that you can validate an idea in a short amount of time. It is better to commit to the idea and validate the concept, then letting it linger, distract and compete with other business ideas and actions. It may take more time than three days, but it should not take months to determine if the idea is worth pursuing.

I initially wasn’t going to pitch an idea on Friday night, but I got caught up in the moment. In the end, I am glad that I did. It allowed me to put the idea that has been hanging around in my head, out into the world. I am honored that out of all the ideas pitched, it was one of ten that made it to a final pitch. I am honored that Rick, Sarah, Demeisha and Rockwell decided to take the journey with me. I also can let the idea go dormant for now.

Lesson Two: 

Ideas are easy, business models can be uncovered, but proving a business can acquire customers is tough.  It was a lot of fun to debate features, customer motivation, benefits of the product, but the largest question we didn’t answer was if we would be able to acquire paying customers. This can be challenging to do over three days, but it can be done. The Wyhoo guys (an on-demand oil change service) had revenue within 24 hours. While we had a strategy on how we would acquire customers, we didn’t have any actual traction to show.

I love this lesson because it helps me further understand that having a great idea is never enough. Unless you have people paying you money, it is not a business. I would also make the argument that unless you have a clear path to profitability, it is not a business.

Lesson Three:

Criticism can be the most valuable input you receive from someone else about your idea.  It hurts to hear someone tell you all the reasons why your idea is not very good and why it will not work. It feels much better when they say they love the idea. But it is the criticism that allows your idea to become a product or business.

Our team spent all of Friday night and Saturday morning working with an idea that we thought would be a great product. As we iterated on the idea, surveyed people to validate the concept, shared with other teams and worked with the mentors  on the business model, we got a decent amount of confusion and skepticism.  It got to the point where I was not sure what we were trying to create. We completely changed the business model at 3pm on Saturday, then made several small changes over the next 24 hours.  Each of those changes were positive. Every change was made because we were willing to hear the criticism, listening to the honest assessments with an open mind.

Final Thoughts: 

I am incredibly happy that I made the decision to participate in Startup Weekend Lexington. Having just finished the Web Development Bootcamp at Awesome Inc., I went into the weekend thinking I would join a team as a developer to promote my newly learned skills. In the end I walk away with many new lessons as an entrepreneur, leader and presenter / pitcher. Maybe the most important thing I take away from the weekend are all the connections I made with other people in our community that are interested in startups and technology.