4 days. That’s the amount of time I have left at Silver Lake. Actually, 6 days if you count the weekend. Cigna, I will miss you!
In my last post, I wrote about the electric feeling of shipping product, watching a customer use something I built. In this post, I will tell you about my most recent experience of that feeling, and how it led me to leave private equity.
2 years ago I was living in a 470 square foot apartment in NYC. For those of you who think this is too opulent for a single person, fear not: there were 4 of us packed in there. The kicker is that in addition to all the normal things 4 people might keep in an apartment, I also had several brown boxes of camping equipment (I’m an avid bikepacker).
Those boxes were a problem, and they begged for a solution. A college friend, my girlfriend, and I started imagining a better world: what if we had cloud storage but for real stuff? No car, no problem! Personalized online catalogs would not only allow us to store our stuff but also to retrieve, sell, gift, or donate at the click of a button.
With that idea, we joined the University of Chicago’s Alumni New Venture Challenge, an incubator-like startup contest. After much trial-and-error, and hours upon hours interviewing anyone who would reply to our Craigslist ads, the project pivoted to focus on helping connect people who had excess belongings with expert online sellers (think: Ebay, Mercari, Offerup).
Real estate brokers but for all the stuff inside your house.
And that idea seemed to take off. Within a few weeks of the pivot, the new solution (“Steward”) had customers and agents across Washington D.C., Boston, Chicago, and New York.
But fairly soon, some fatal problems cropped up:
Agents were typically experts in some product types but not others. This meant that the agents spent significant time researching products they didn’t know about, eroding their effective hourly wage.
Low manufacturing costs made it very hard to justify any real “effort” or logistics to sell most household items.
Idiosyncratic (“lumpy”) sales patterns made inventory expensive and, when using an agent's home as a warehouse, very frustrating for the agents. Secondhand glut exacerbated this problem.
Competitors were solving a lot of these issues with better solutions than we could offer (ex. Buy Nothing was exploding for low-cost items; point-solutions like Decluttr were solving for high-value items like phones and computers; large companies like Amazon and eBay were turbocharging the seller “research” process with their own technology in a way that was already baked into the agent experience).
Eventually, based on these variables, we decided to close Steward. But in the process, I learned some important lessons:
Community drives productivity. As much as possible, work around and with people who encourage you. Deadlines, stand-ups, sharing of best practices, abating loneliness.
Low code software is a miracle. I built Steward’s software solution (a proprietary inventory management system for agents and clients) using Glide, a simple low-code UI that sits atop Google sheets. But there are plenty of other low code / no-code solutions out there. I’ll talk more about low code and how to choose a low code solution in a few weeks.
Initial sales come from your network, not digital ads. So important. Again, more to come.
Serving customers consumes your life. When Steward was in full swing, it was not just a full plate but a four-course meal. On top of building the software, fixing bugs, and managing agents, I also became an agent myself - selling everything from baby carriages in Chicago to Don McLean records in New York. I was also juggling marketing, customer interviews, and the nuts and bolts of insurance and legal issues along the way.
It’s a blast. One way to tell if you’re having fun is to think about how much willpower you have to “spend” to get something done. I don’t remember spending much in those months working on Steward.
But the real ah-ha was simple: whatever this pre-seed process was, I wanted to do more of it.
My contract with Silver Lake required me to stay until January, but by October 2021, I was systematically exploring other “problem spaces.” The search led me to consider everything from how to build real-time hospital price transparency (why can’t they tell us how much the blood test costs before they take our blood???) to offshore personal assistants for busy moms and dads.
And then I found the real thing, the thing I plan to focus on for the next few months, and explain in my next post.
It came to me through an unexpectedly sublime experience: playing chess online.