Time to Build?

Chasing conviction, one experiment at a time

Over the past six months I’ve been trying to figure out what’s next for me. I was applying to jobs first in VC, then in tech sales. No success, but I should have expected it — I wasn’t all in. I didn’t have the fire in me that I typically have when applying to jobs. So I stopped applying.

Then, something happened.

I decided to explore an interest I’ve long held and have kept pushing off because…it was scary: building something of my own.

The following is taken directly (aside from a few edits) from a recent monthly email update I send to a group of family, friends, and founders/investors I highly respect.

Story time.

Six years ago, I was interested in doing an MBA to pursue one of two paths:

1. Product Management at a tech company

2. ETA / Search Fund

I told myself that I’d see how far I could get with either path before I committed to an MBA. What I also knew about myself was that I was tossing around the idea of starting a company. I had an idea in mind, one that I had actually mentioned to Sid while we were sitting in a booth at a Silver Diner in Tyson’s, VA one evening while I was interviewing for my role at Sunny Day Fund.

Why didn’t I decide to strike out on my own as a founder? Well, at first I thought it was because I wasn’t ready to be a founder and needed to gain a bit more experience in the tech world. However, I eventually realized it was because I didn’t have a level of conviction in my ideas that I required of myself to take that first step down the difficult foudner path.

So, what happened next?

Well, four years ago I landed my role as a PM at an early stage fintech, Sunny Day Fund. Perfect, I thought, I guess I don’t need an MBA.

My search for a startup was deliberate. I was specifically looking for:

1. pre-seed/seed & less than 30 employees (I wanted something small)

2. fintech

3. the opportunity to take on roles across the company

4. do something that had a meaningful impact on peoples lives

I wanted to get as close to being a founder without actually being a founder, as close as possible to being able to build something from scratch.

But I was still thinking about purchasing a business. I had two reasons: 1) Generate cash flow
2) Get a front-row seat to the pain points of SMB owners, then angel invest in or build solutions for them.

I even modeled out purchasing a commercial property and starting an equestrian facility from scratch, but I obviously didn’t have the equestrian-specific operational expertise. I floated the idea around with some folks that my wife and I knew.

Then came the opportunity.

Three years ago, Emma and I were approached by a friend to purchase an equestrian business whose owner was looking for liquidity. We would partner with a friend that knew the operations side and it made sense. We modeled it out, proposed a purchase price, and signed an LOI. Since this was a fast moving deal and I knew nothing about SBA loans at the time, we paid all cash. I had to sell my favorite car (I was a BMW nerd and enjoyed track days), liquidate a large portion of my investment portfolio, move from our house to a tiny apartment on the farm to cut housing costs, and structure the deal to be paid over a few months to make it happen.

Mind you, I was still working at Sunny Day Fund at the time and I knew this business would be a lot of work to turnaround. It was. I ended up working 8am - 7pm for Sunny Day Fund, then evenings and weekends on the acquired business. My social life was non-existent (I was far away from family and friends) and my mental health deteriorated. That sucked.

The result? We grew the business from $500k to $1.3M in revenue within 1.5 years, while similarly growing net income, and we streamlined and stabilized operations.

Nothing crazy compared to other growth stories out there, but I thought it was impressive given the constraints we faced as an equestrian facility (horses per acre, facility size, scheduling, available labor, etc.).

Then one year ago, I had a kid on the way and knew that my window to try my hand at other interests was quickly narrowing. I took a three month break from Sunny Day to travel, live in Mexico City, and do growth for a company going through YC’s S24 batch.

At the end of the three months, I decided to continue experimenting, leading to VC fellowships and launching the podcast.

That brings us to today.

So, what’s next?

There are two paths I’ve been actively exploring and that I’m excited about:

1. Startup: Build, build, build — that’s all you’ve heard from me in this essay. So, what have I been wanting to build? Well, I want to build the tech that I wish I had as an SMB owner, and after talking to other SMB owners over the past couple of months, tech that they also wish they had as well. Owners are experts in their customers problems, not their own operational challenges. I want to build the tech that allows owners to focus on their customers. I know what needs to be built first as the wedge and I’m working on getting it all written down in a clear way. In the meantime, I’ve been interviewing potential technical cofounders and I’m continuing to talk to SMB owners.

2. Another acquisition: I’ve been considering another acquisition for some time, but held off since this time around, I’d need to be able to dedicate myself 100% to the business. Ideally, I’d purchase a business, then once stable, use my cash flow to fund an engineering team to build #1.

Stoked? Me Too.

If building for SMBs or acquiring SMBs excites you, let’s talk 🤝

---