TLDR: After more than 10 years as a full-time entrepreneur, I’m retiring. For the foreseeable future at least. To put my skills to good use, I intend to join a venture backed, growth stage startup.
Update — Jan 16, 2023
I’m thrilled to share that I’ve joined Virginia Venture Partners as an Investment Associate. VVP is a growing family of early stage venture capital funds with $100M AUM and a portfolio of 300+ startups.
We are industry agnostic and invest early in scalable technology businesses at the pre-seed and seed stage. We regularly invest in pre-revenue startups but rarely pre-product.
If you are the founder of a Virginia based startup raising capital feel free to reach out. Apply for investment from VVP or contact me directly at:
I’ve been a full-time entrepreneur for my entire professional life. I started my first real business while I was still an undergrad and never looked back.
To be fair, at 21 there wasn’t much to look back on. In college I worked at the front desk of a hotel. In high school I worked in a retail stockroom. Before that, I washed dishes at a restaurant where I lasted exactly one day.
Entrepreneurship, and especially tech, always captivated me. I was born in 1987. When I was five, Congress passed the Scientific and Advanced-Technology Act of 1992, creating the commercial internet.
Around the same time, my family got our first computer, an Apple Macintosh II. I was hooked immediately. A few years later, I was online thanks to AOL and a dial-up modem. By middle school I was learning to buy and sell things on eBay, inspired by my older brother who launched an online store for rare books in the mid-90's.
In high school I taught myself how to build websites and launched an online fine art gallery with a friend. We represented 15 professional artists and sold their work on commission. In this capacity, I became the youngest member of the Ghent Business Association and helped launch a popular gallery crawl in Norfolk’s high-end retail district.
My goal to play varsity soccer in college was derailed when I suffered a devastating knee injury in 2005. In total, I tore 14 ligaments and tendons. Only my ACL remained partially intact. The injury also caused severe nerve damage which resulted in “foot-drop,” a condition that prevented me from lifting my foot and walking normally.
My knee was expertly repaired by a local orthopedic surgeon. With the help of incredible physical therapists, and many hours in the gym, I was able to rebuild my strength and flexibility. But, I still suffered from foot-drop and my options for repairing the nerve damage were limited.
I had recently turned eighteen and had a difficult decision to make. I could choose an established procedure, with a historically low rate of success, that would put me under anesthesia for 36 hours and cost a king’s ransom. Or, I could undergo an experimental surgery at the Washington University hospital in St. Louis.
The new surgery was adapted from a procedure the surgeon pioneered for a similar nerve injury in hands, but its efficacy for foot-drop was untested. This surgery would last 7 hours and cost about 5% of the more established option. I took the experimental route.
I was the 4th person in the world to have the procedure done, and the first to recover successfully. This was one of the first big risks I took, and it changed my life forever. My risk tolerance, my pain threshold, and my ability to persevere all went way up.
Despite being of no use to the school’s soccer program, I was accepted by the College of William & Mary and enrolled in 2006. There I discovered a love of architecture and occupied my time outside of class exploring various business ideas.
By my senior year at William & Mary, I had an idea that seemed promising. I modified a robotic massage chair to accept payment from debit accounts attached to student ID cards and installed several in the school library.
The massage chairs were a hit with students, racking up tens of thousands of uses in the first few months of operation. Unfortunately, the payment system was unreliable and roughly half of the transactions failed to process completely.
After intense troubleshooting I discovered that fixing the problem would require a major upgrade to the school’s outdated Unix-based network operating system. This was not going to happen. At least not on my timeline.
Given the situation, I couldn’t operate profitability with my pay-per-use revenue model and needed to figure something else out. So I struck a deal with the student council to rent the units on an annual basis and make them free for students to use.
The revenue model adjustment radically reduced my cost structure and increased the size of my addressable market at the same time. I no longer needed to modify the chairs, and I could rent to anyone. This changed everything.
When I graduated in 2010, I went full-time on the business and started working out of an incubator affiliated with the W&M business school. The glacial pace of the higher education procurement process turned me off from chasing more university customers and I started looking for alternatives.
A chance meeting with the CEO of a design / build firm that specializes in trade show exhibits, resulted in an invitation to meet some of his clients. I pitched the chairs as a unique way for the exhibitors to attract attendees and create a captive audience for their sales people during events. I started taking orders that day.
I had exactly zero inventory, but I had a few months before I had to actually deliver chairs. So, I reached out to the CEO of the company that manufactured the massage chairs I had modified at William & Mary. I explained the new opportunity and asked if he had any product I could use.
The brand had recently discontinued a model he felt would be durable enough to handle the trade show environment and we negotiated a deeply discounted price. The catch: I had to buy all of the remaining inventory. 80 massage chairs.
Even at a per chair cost roughly 85% below retail, that was a lot of money I didn’t have. So I went to a small local bank with my customer orders in one hand and my deal to buy inventory in the other. I fully expected to be laughed out of the building.
To my surprise, they agreed to loan me what I needed. Even more surprising, they were willing to use the inventory to collateralize the note. I borrowed a little less than 30% of the inventory’s retail value, figuring I could sell the used chairs for 50% below retail to repay the note if things didn’t work out.
Thanks to the bank loan, I now had a functioning business with inventory to rent, orders to fill, and a little working capital. I built a website, learned some basic SEO and quickly began ranking on the first page of Google. It helped that there was very little competition for my keywords at the time.
When the business started to grow I relocated to Washington, D.C. and became involved in the local tech community. I helped organize events and built a platform with friends that connected startups to talent, capital, and resources. During this time, I also met my wife while she was helping to launch WeWork in D.C.
New competitors eventually emerged, but a solid foundation of repeat business from blue chip clients allowed us to continue to dominate the event rental niche, launch a direct-to-consumer eCommerce brand, and expand into B2B sales. After seven years of successful operations, I sold the business and launched a software startup.
I teamed up with my partners from the last business and several early WeWork employees. Inspired by co-working, we set out to make it easier for traditional multi-tenant office buildings to manage and monetize shared spaces. To start, we focused on large conference centers in class-A office buildings.
Our first customer was a $10MM conference facility in the base of a $1B trophy class office building on Pennsylvania Avenue in Washington D.C. The building’s 3-person property management team was struggling to manually coordinate reservations for 60+ blue chip tenants ranging from Apple to AstraZeneca.
We took over management of the facility on day one and started building software to streamline operations. In the first three months, we launched digital signage, online reservations, and a novel credit system to manage competing tenant booking rights. In the first year we increased utilization by 1,100% and attracted over 2,000 hours of bookings.
The following year we onboarded several more buildings, added event services to the platform, and doubled the size of the team. In February of 2020 we hit a milestone of $60k of monthly revenues and started pitching well known VCs. In March of 2020, COVID hit the U.S. and our market evaporated.
On April 15, 2020 I was forced to lay off the majority of my team in an effort to survive the pandemic. This was incredibly difficult for everyone, but our strong culture built on kindness, integrity, and responsibility carried us through it. I’m so proud of our alumni who are now thriving at great companies from Accenture to UrbanStems.
When it became clear people were not returning to the office in the fall of 2020, we wound down fully and off boarded our remaining customers. I began consulting while I tried to figure out what to start next. In the following year, I explored and tested more than a dozen startup ideas. Nothing materialized that met my requirements.
Recently I made the difficult decision to retire, at least for now, from full-time entrepreneurship. At this stage in my career, I believe I can learn more by joining a larger organization than by pursuing any startup in which I lack conviction. At the end of the day, I want to be part of a high performing team solving hard problems.
Thank you for reading this far. Believe it or not, this is the short version. I feel very fortunate I was able to chase my entrepreneurial dreams, and experience some success at a young age.
There are too many people to list who helped me throughout my journey in ways I’ll never be able to repay. You know who you are. Thank you for believing in me. I hope to be able to support others the way you supported me as I move into the next chapter of my career.