Built From the Field by Chris Momongan
🗓️ Posted: @May 5, 2025
✍️ Category: Lessons from the Journey
The first time I intentionally started using systems was when I was forced to—right at the start of my investing career.
Sure, if you’ve ever worked in corporate, you’re using systems whether you realize it or not. But I had never actually said the word “systems” out loud. I hadn’t even consciously thought about it, embarrassingly enough.
Then I heard Episode 773 of the BiggerPockets Podcast:
"Replacing His Income with $70K/Year Cash Flow After a Close Call with Death"
Pasha Maleknia shared how being stuck in an airport during a war—literally unable to leave—became the moment that pushed him toward building financial freedom through real estate. Coming from a tech background, he talked about how he leaned into systems to scale.
That episode hit me.
I remember showing up to a local BiggerPockets meetup in Augusta soon after, buzzing with excitement and telling everyone how I was going to start using all these new systems. Looking back, I’m pretty sure some of the more seasoned investors were thinking, “Who is this noob?” 😂
But that was the spark.
It didn’t all change overnight, but from that point on, I began to systematize every part of my business. And that mindset shift has shaped how I operate to this day.
💡 The Mistakes I Made Early On
Back then, I was making a ton of mistakes. Mostly from believing I had to do it all myself. I was short on capital, so outsourcing felt like a luxury I couldn’t afford.
Why pay someone $60 twice a month to mow the lawn when I had all the time in the world and was perfectly capable of doing it myself?
So that’s what I did. I crammed a mower and tools into my Nissan Murano and made it work. It was inconvenient, inefficient, and definitely not scalable.
Fast forward to now—I manage five Airbnb units. I don’t have time to be the landscaper, handyman, or cleaner. Systems aren't just about efficiency; they’re about freedom.
🧰 Systems I Use Today
These are the systems—both tech and people-powered—that keep my business running:
- Hospitable – for automated messaging, scheduling, and AI-generated guest replies
- ChatGPT – for responding to more complex guest questions or refining communication
- Google Sheets + Notion – for financial tracking, vendor management, and SOP documentation
- SOPs (Standard Operating Procedures) – for everything from turnovers to repair workflows
- Airbnb + Vrbo – primary platforms for listing and managing bookings
- Yale Keypad Door Locks + Blink Cameras – affordable and consistent smart security setups
- Ecobee Thermostats – to manage HVAC systems remotely
- SimpliSafe – for added security in C/B class neighborhoods
- DealCheck App – for quick deal analysis and running initial numbers
- MileIQ – for automatic tracking of business mileage
- Chase + Bank of America – for managing business and credit card transactions
- Lowe’s, Wayfair, Ace Hardware, Costco – preferred vendors with apps that allow me to pull receipts and invoices easily
- A reliable accountant, handyman, plumber, electrician – trusted people in my vendor network
- A reliable cleaner – a consistent and trusted part of the team
- A trusted landscaper – someone I pay with zero hesitation now
These systems give me bandwidth to focus on growth—not just survival.
🤝 The Power of Community: Aaron Chiles
Another pivotal moment came from someone I met at that early meetup: Aaron Chiles, owner of Prepared Space LLC.
Aaron was a few steps ahead of me in his Airbnb business, but what really stood out was his systems mindset. He had everything dialed in—software, automations, vendor relationships.
He’s an engineer (like many of the sharpest investors I’ve met here) and had a brain wired for optimization. When I was still cleaning units myself, Aaron showed me a different way. He shared his process, his vendors—everything. He didn’t gatekeep.
"A rising tide lifts all ships."
Aaron lived that out. And I tried to follow that same mindset, even when I didn’t have much to offer yet.
Looking back, Aaron was one of the most important people I met when starting out. He embodied stewardship and community, and his generosity helped shape the systems I use today.
Looking back, that BiggerPockets episode and those early Augusta meetups laid the foundation. Systems didn’t just save me time—they saved my sanity. They turned chaos into clarity.
And I hope sharing this helps someone else skip the lawnmower-in-the-Murano phase a little quicker.
🎯 Takeaway
If you’re just getting started, remember this:
- You don’t have to do everything yourself.
- The right systems create space—not just in your calendar, but in your mind.
- Community is a multiplier—surround yourself with people who share, not gatekeep.
Start where you are. Use what you have. And keep refining as you grow.
🔗 Follow the Journey
More entries like this—real, reflective, and in real time—are coming soon.
→ @builtfromthefield (brand)
→ @chrismomongan (personal)