Dolly Sods

I took a liking to hiking and backpacking in college, having not done much of it as a kid (at least as far as I can remember — though I’m sure my parents will bring up some obscure time when I was five).

I saw hiking and backpacking as a way to escape the monotony of daily life and step outside my routine and comfort zone. There was something special about walking alone in the woods, taking in nature, and letting thoughts come to me. It was my meditation of sorts.

One particular trip stands out. It was my final semester of college, and I was anxious about graduating, finding a full-time job, and deciding whether to ask my now-wife to start dating seriously (we were “just talking” at the time). I decided what I needed was a solo backpacking trip. After some research, I landed on Dolly Sods in West Virginia.

It was late October 2015, and I planned a three-day, two-night trip — Friday through Sunday. Since I had to work that Friday and then drive three hours to reach the trailhead, I made the first day an easy two-mile hike to ease into it.

Ease into it I did not.

In terms of clothes, I showed up with shorts, a fleece mid-layer, my rain shell, a beanie, and hiking socks. That’s it. Big mistake.

That evening, the temperature steadily dropped to 24°F (according to my watch hanging in the tent). My sleeping bag was only rated to 30°F, and I didn’t have a liner. And those shorts? My legs were fucking freezing. You’d think that, being late October and knowing I’d be at higher elevation, I would’ve packed warmer, but I guess hindsight is 20/20.

As I sat shivering in my sleeping bag, I threw on my second pair of socks, my fleece, my rain shell, and my beanie, then curled up into the fetal position. I tried to sleep, only to be woken up intermittently by coyotes howling in the distance and the rustling of leaves around my tent.

The next morning, I couldn’t have been more eager to light my stove and make my Quaker apples and cinnamon oatmeal (two packs of it) and coffee (typically Nescafe instant coffee). I’m pretty confident that first bite of piping-hot oatmeal healed me. I could feel its warmth sliding down my throat and spreading through my core. I couldn’t get the rest of it inside me fast enough. When I finished my oatmeal, I squatted next to my stove, wrapped my hands around my mug of coffee, and sipped until it was gone.

I packed up camp and decided the best move was to start hiking to warm up. But first, I had to rethink my plans. There was no way I was enduring another frigid night like that, but I didn’t want to leave without getting a few miles in. I needed to find the balance between not wanting to be a quitter and not putting myself at risk of hypothermia. I pulled out my map and traced a route that would give me about ten solid miles before dropping me back at my car.

Those ten miles were divine. If you’ve never been to Dolly Sods, go in the fall. The hills of brush turn a deep red, the windswept trees look dramatic, and the solitude is both calming and unsettling. I know it sounds crazy, but those ten miles really changed me. There’s something spiritual about enduring something tough and being rewarded with beauty.

But the fun didn’t end there.

My hike ended back at the car just as the sun was slipping below the horizon. Normally not an issue, except in this case my phone had no service and I couldn’t pull up directions to get down the mountain. And now it was dark. Great.

I figured I’d follow the gravel road down to a major road, then rack my memory for directions. I made it to the base, found the nearest major road, and kept driving until I spotted a McDonald’s. I pulled into the parking lot, connected to the WiFi, loaded directions home, ordered a large fries as a reward, and hit the road again. Thank God for McDonald’s WiFi, I thought as I drove home.

When I finally got home, I crawled into my warm bed, pulled the covers over me, and passed out. What a wild 36 hours.

Clarity

That clarity I’d been searching for — the reason I’d gone on the trip in the first place — I found it. Two weeks later, I asked my now-wife to be my girlfriend. I knew that if I was going through life, I wanted to do it with her. I also kicked my recruiting into high gear to make sure I landed a solid role post-graduation — and I did. That trip was just what I needed.

I’m not sure how long it was after that trip, but I eventually came across the concept of Type 1, 2, and 3 fun one day. Looking back on this trip, it was definitely Type 2 fun. It pushed me out of my comfort zone, but I’d do it again in a heartbeat if given the opportunity. In fact, I wanted to do it again. I wanted to finish the original trip I had planned before I had to cut it short. I promised myself that one day I’d finish what I started.

A decade later, I got my chance. More on that soon. 😉

Enjoy a few photos from my October 2015 trip.

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 🤝

Respectability is seductive. It feels safe. It feels like progress. It convinces you that you’re on the right path. But here’s the thing: respectable people rarely change the world.

Founders aren’t respectable. They’re scrappy. They’re fine with failing, often and in public. They live with rejection, embarrassment, and risk in a way that respectable paths never require.

That was my problem early on. I was raised to believe a respectable career was the goal, and that running a business was, at best, a backup plan. Deep down I always wanted to build, but instead I played it safe. I climbed the corporate ladder. I told myself I was being smart. I was hitting all of the “milestones”: max your 401k, save and invest in stocks, buy a house, etc.

Then one day, I’d had enough. I was in my late 20’s and if I was going to try something different, it’d have to be now. I wasn’t brave enough to quit and start something of my own, but I thought I could at least get closer to the fire. So I joined an early-stage startup, just to get a taste. Worst case scenario, I come back to consulting.

That taste ruined me, in the best way possible. I loved it. I can’t stomach the thought of a corporate job anymore. My body rejects it.

That tiny step towards building was all it took.

Since then, I’ve bought and run a small business. I’ve started a podcast and a newsletter. And now I’m diving into building for SMBs.

So to hell with respectability. To hell with the “right path.” I don’t want a life that looks good on paper, I want a life where I can build something that leaves a mark.

This essay is my second step in that direction.

If you feel the same, reach out. Let’s talk.

- Cyrus

“Let those who wish have their respectability- I wanted freedom, freedom to indulge in whatever caprice struck my fancy, freedom to search in the farthermost corners of the earth for the beautiful, the joyous, and the romantic.” ― Richard Halliburton

“Respectability is a curse; it is an “evil” that corrodes the mind and heart. It creeps upon one unknowingly and destroys love.” ― Jiddu Krishnamurti

A few years ago, inspired by my sister, I reluctantly started journaling - despite a lifelong dislike for writing 1. I’ve always had a preference for verbal discourse 2 over putting words on paper, but to my surprise, journaling changed the way I think.

Structuring your thoughts has its time and place, but when journaling, a stream-of-consciousness strategy can be more effective. Not only does it lower the level of effort to start journaling if you’re new to it (and to continue journaling, if you’ve struggled from on-off journaling), but it also helps you get your thoughts down faster and in a “raw-er” state that you can later review and refine. I’ve found that if I try to placate my perfectionist tendencies and structure my thoughts before journaling, I risk unintentionally biasing them. The structure itself may distort my original ideas or I may overlook deeper meanings while trying to organize them.

Now, this doesn’t mean my journal is full of nonsense - though, I’ll admit, some pages do come incredibly close. After I write my thoughts down, stream-of-consciousness style (the raw data, if you will), I’ll review my notes and create a more structured understanding of my thoughts using bullet points. This method mirrors my approach to research: start with raw data, then refine into structured insights. Afterwards, I’ll add takeaways or action items where applicable, but the key is that I’ve captured my thoughts in a permanent state (that is unless my journal decides to spontaneously combust). After all, journaling isn’t about perfection - it’s about getting started.

So there you have it, my approach to journaling that prioritizes “just writing”. Who cares if it doesn’t make sense right away, it doesn’t have to. The true purpose is to document your thoughts at that point in time so you can reflect on them later. I like to think of it as taking Time Machine backups of my brain at that point in time. And with no pressure for perfection, journaling quickly becomes a habit, one that eventually feels second nature.

What’s your approach to journaling?