About Ben

Just a guy from the Pacific Northwest 🏔️ living in the Midwest 🌾 now.

I grew up in Eugene and then moved to into cohousing on an island off of Seattle when I was seven. I was an only child until the age of four when my parents adopted my sister from São Paulo. I remembering the tangible excitement of having a little sister leading up to the trip and then the frustration of this little ball of energy that wouldn’t do what I wanted. Another strong memory was putting my dad’s sunglasses above and behind the seat on the taxi cab. We discovered that the glasses were lost when we returned home and I set out to find all of the phone numbers for the taxi’s and call them all. I remember being blown away when my dad explained how many phone calls that would take and the sheer size of the problem.

In Eugene, I remember practicing sleeping and being able to close my eyes at night and open them in the morning with continuous cognition. I skipped dreaming and simple snapped between night and day. I’ve tried to reproduce this as an adult and have not been successful. I also remembering sitting on the floor of my room and gazing out of the window and the realization that my parents would die someday made me profoundly sad. This was around the same time that I got in trouble at school for peeing outside. I was so confused as I went to a private school and was doing a private thing. I loved this school and remember being in the lunch room and meeting a new friend and explaining that I was two and seven twelfths old because there were five more months until I would turn three. Another fold memory was our neighborhood block party for the fourth of july. I remember setting up a firework that would spin on the ground. I put it on its end and it spun into the air and into a woman’s shirt! When I was six we took a trip to Bainbridge to visit the our new potential home. We stayed in a guest room and all of my new friends came over to pay legos. I remember being upset as one of them took parts I wanted to use.

As I grew older in the community I became engrossed in building things and complex systems. My dad had an early Macintosh and I spent hours building spreadsheets and writing. My best friend and I also started to build role playing games. I spent years developing dice frameworks for damage and character attributes that diverged from D&D. I created a game called DWK and my best friend created DSK. We would play ofter and he would always be the dungeon master and I would be the player. Later we branched out into sports games and created a baseball one with mechanical attachments to players so they could shoot the ball and have better “throws” to based.

The community was a wonderful place to grow up. Most of my friends lived just down the walking path and we would spend our days playing in the rec room and at each others houses. We would simple walk in to play. We also had a small field that hosted soccer, baseball, and football behind the common house. There was a small pond next to the field where we lost many balls. We would build rafts when it rained and filled and would spend hours walking in the woods and building tree houses. Later on we found massive blackberry patches and took clippers to make intricate paths and rooms that we called SPDs (super protected defense).

My elementary school was similar to the community with a large wooded area and many trees that we climbed. We would play at recess for hours each day and create games like digging for gold and long jumps into the sand. There were many fun activities including sleep overs out in the woods under the cover of the gym. One night during a sleep over I remember coming out of a dream jogging down a trail in the woods. One of my teachers had woken up and was jogging along behind me 🙂

Life on the island was wonderful and I spent many summers on my friends sail boats and dock jumping into the frigid puget sound water. High school was a big transition. I moved from a small private middle school with a tight knit class of 30 close friends to the public high school with 1200 students. I remember going into it with the intention to create a varied group of friends. I wanted to be able to flow in and out of different groups with ease. A friend of mine would just walk into a group and stand there until he had something to say. I thought this was so imposing and awkward. I met friends in classes and built many groups of friends: some academic, some social and different sports friends.

Two moments in high school stand out. I remember playing soccer behind the football field and the football team running by and feeling ashamed that I didn’t play football because it was cooler. I also remember taking a C++ class in high school and a “cool” friend walking by the class and being ashamed of taking it ever though I really enjoyed building programs.

High school was a transformative time. I learned to drink and to party with the cool kids. A neighbor invited me to my first “party” at a friends house and I went and dug up my “party shirt” and wore in proudly and was very disappointed when everyone didn’t recognize me for my white t-shirt with the tokimon logo on it. I quickly learned that going out was more about joining a select group of friends at a house party and just hanging out. My mom also moved away to Eastern Washington as high school started and my dad struggled immensely.

The last year of high school contained massive loss. A girl that was pursuing me was killed suddenly in a car crash. A few more friends were severely injured and died in car crashes. My dad went bankrupt and lost our home. We were fortunate to move into a beautiful home on Rockaway Beach that a friend owner and was designed as a single level home for when she was older. She lived next door in an older two story home.

As the bankruptcy proceeded things became very hard for my dad and my step mom and they got divorced. He also lost an awesome investment property they had purchased and fixed up. My dad moved to Madison Park in Seattle and I went away to college.

College was a very interesting experience. I remember observing friends in high school that were focused on going to certain schools from an early age. I was not like this. I just went through the motions. My parents set me up with a college advisory service and we picked schools on a whim. I wanted to get away from home and move far away but I did not care where. I had chosen a number of schools on the East Coast and then my dad took we down to California to visit schools. I look at Santa Clara and fell in love with the beautiful campus and decided to attend ever though it was a safety school. California was just so beautiful and warm and I loved the fast pace of life.

College was very challenging. I entered a new group of friends and a new world and struggled managing my own life. I lived in the dorms in a suite with seven other students. I didn’t eat much and struggled with discipline. High School was much more academically challenging and rigorous and I found that I could skate through college without doing very much work which turned out to not be a great thing. I fell into a group of friends that were all studying Electrical Engineering and so I decided to study the same thing as it was easy and seemed like a good degree. A friend and I were on the same path junior year while in an engineering physics course. He worked part time building circuit boards for a local startup and we build a really technical amplifier together. Then I went to Florence to study abroad and he stayed home. When I returned he was still focused on physics and went on to a Ph.D. at Yale and I finished out my undergraduate degree and joined a fast growing startup.

When I left college I experienced another profound loss of community and friendship. All of my friends moved onto work and a separate life. It hit me that our schooling system sets us up to be separate and alone (in its aim to make us self sufficient and individual). We go through elementary school then move to a new environment in middle school and then again in high school. Then we have a massive change when we go to university and then again when we enter the working world. Many people enter the working world lost and spend the rest of their life finding their tribe and their circle of security and comfort.

I experienced another one of these short journeys over the next five years building the startup from pre-revenue to 115M in annual revenue and sale. It became obvious after three years that we did not want to build a business and instead were intent on building something to sell. Lipstick was plastered all over the pig, key decisions were made and the company survived to sell a few years after I left. The CEO and a few select lieutenants in the business carved out a large chunk of money and the stock was converted so that everyone else was left without anything to show for our work. It was a blessing and an expensive lesson. I had friends and friend’s parents that had been successful in the startup world and now had an F50 in the garage and financial security. I learned that this life was risky and if I was not in control of the company then I stood to lose a lot if things did not go to plan, and things never went to plan. It was about good people, simple ideas and consistent execution.

At this point I was seriously dating my future ex-wife and we were both working crazy hours. She was an accountant working for a big audit firm. Her mother had build and sold an executive search firm in St. Louis and had bought another one that she now ran. My parents were both from St. Louis and my grandma was still there and in great health. We decided to leave the startup grind and move to St. Louis for three to five years so she could work for her mom’s company. We left Silicon Valley and I took a role with a SaaS startup out of Ottawa. A good friend of mine was an investor and advisor and brought me in to help scale the business.

I joined the fledgling company with high hopes but a realistic outlook on their potential. The founder ran and sold a successful graffiti removal franchise. He fell into a lot of government work in Ottawa and his revenue skyrocketed. He saw a need for better scheduling, dispatching and management software in a massive niche that was not being address and set out to build a solution. It was a great idea but poorly executed. When I joined they had a robust platform that worked for their clients build on .Net. When I showed up to join the executive team, they had made the decision to throw away the codebase and build from scratch with Ruby on Rails. They had no reference to get to feature parity. Over my two years with the company, they never achieved feature parity. Ever worse, when I joined they touted customer counts and revenue numbers that were fabricated. I was in a discussion to move from COO to CEO of the company and turn it around when my CEO made a terrible side deal with investor and began drinking heavily in secret in the back room. I got my money out and moved on. Again I had built something powerful that for many reasons was not successful.

I now found myself living in St. Louis without a strong social network beyond couple friends and a young group of friends from a charter school I volunteered for. I set out to rebuild the SaaS company and network. I spent two years decompressing from working all of the time and learning about raising capital and building a business from scratch. I learned about my limits as a solopreneur. When you do everything yourself, you quickly run out of time to do the basics. I hired an offshore team and build the SaaS product on a modern stack. I had daily calls to manage the development backlog. I build slides and roadmaps and talked to investors. Ultimately, I decided to shelf the project. I bootstrapped everything and make the choice to not take on growth funding. I had lived the growth funded startup life and wanted to make good long term decisions and not be pressured to acquire customers and meet financial goals. I also wanted to see software deployed and built at scale. So I joined a software consulting firm to work with big St. Louis companies.

Through schooling and work I slowly began to understand the employee / employer relationship. Companies work in defined markets and can teach and employee a lot about an industry and a discipline. Employees must be consistent and stable and do what they say they are going to do when they say they are going to do it. Joining a venture backed startup out of school was a blessing because it exposed me to so many disciplines and allowed me to bite off as much as I could chew. It was also a unique environment where change is desired and the current state is not the expected future state. One secret I have learned is that the vast majority of organizations don’t want change. They want things to stay as they are (predictable) and incrementally grow their top line revenue. Consulting was different because we are brought in to fix a current problem or grow something new in an established business. It is an environment where change is not only desired but expected.

I joined a rapidly growing local consulting firm and was able to consult for Fortune 100 and 500 companies locally in St. Louis. I helped strategically and I build software. The fast pace was a nice change and the autonomy was wonderful. My office was walking distance from my house but I sent most days between my home office and client sites. We were the fastest growing office and with this came a lot of politics. After three years it came to a head with many people leaving and the culture falling apart. Although it was sad to see something great fall apart again, I had gotten what I came for and so I moved on.

Being a part of so many startups is rewarding but it is also draining and so in 2021 I decided to take proven processes and build something with a few more guardrails. I purchased a franchise out of Montreal and started to build it in St. Louis.

I quickly found that starting a Canadian franchise that is just beginning to scale is completely different than buying a well established franchise from someone like Neighborly. This particular brand was even more challenging because they run three separate businesses under one roof. I started out selling and installing kitchens only in the fall and winter and then took on exterior projects in the spring and summer. Various things happened in the business but it was incredibly educational and after one rockstar year, I shelved the business.

Next I moved on to an acquisition and establishing my Private Equity company. I purchased a small freight company and started operating long haul semi trucks across North America. Initially I planned to buy additional tractors and scale the company but after operating for some time it became clear that the best path forward was through additional acquisitions.

Today I spent most of my time on Windrush Capital and acquisition activity. I play hard with my kids and am active in my local community. I play competitive soccer and ultimate frisbee and have gotten deeply into pickleball in the past few years (sort of a requirement being from Bainbridge Island!).

If anything peaks your interest or if there is shared experience you’d like to dig into please don’t hesitate to shoot me and email and or connect with me here.