I Run Three Bootstrapped Companies. Here’s the System That Connects All of Them.
Pablo Gerboles Parrilla is a Spanish entrepreneur based in Costa Rica. He competed as a Division I collegiate golfer, briefly turned professional, then rebuilt from the ground up after his first major venture failed. He now leads three bootstrapped companies spanning DevOps infrastructure, digital marketing, and live event production. Here’s Pablo on the operating philosophy he built across all three.
Who I Am
My name is Pablo Gerboles Parrilla. I’m Spanish, based in Costa Rica, and I currently run three companies: AliveDevOps, a DevOps and software infrastructure firm; Pabs Marketing, a digital marketing and influencer strategy agency; and Pabs Entertainment, which focuses on the strategic investment and organization of live concerts in Costa Rica.
Before any of this, I was a Division I collegiate golfer. I competed at a high level and briefly turned professional after graduation. I stepped away from the sport because of autoimmune issues that caused serious joint problems. Doctors couldn’t pinpoint the cause. I was in Spain, physically and emotionally exhausted, and my family had invested enormous amounts of time, money, and belief into my golf career. Letting go of it was one of the hardest things I have ever done.
That decision forced me to channel everything I had learned in competitive sports into building something new. And golf teaches you more than most people realize.
Why Three Companies Share the Same Operational DNA
At first glance, DevOps infrastructure, digital marketing, and live event production look like three completely different industries. They are. But the operating system underneath each one is largely identical.
Every company I build starts with the same principles: lean teams, automation from day one, global talent, and a weekly payroll rhythm that forces me to stay financially connected to each entity I run. The specifics of what each company delivers are different. The discipline governing how they run is not.
Golf trained me to think this way without knowing it. You don’t treat every tournament like a separate career. You bring the same preparation, the same mental framework, and the same routine to every round. What changes is the course. The same applies across three companies in three different industries. What changes is the terrain. The operating approach stays consistent.
In golf, consistency beats intensity. It’s not about one great shot or one big win. It’s about showing up, making calculated moves, and adapting when conditions change. That’s the same muscle I use across AliveDevOps, Pabs Marketing, and Pabs Entertainment.
The Rule I Invented After Getting Burned
I lost six figures of investor capital on my first major venture. Then I was scammed out of another six figures on top of that. Financially, I was destroyed.
What saved me wasn’t a new idea. It was a services business I had been running quietly on the side while everything else was falling apart. I had hired a small team, acted as project manager, and run it at roughly a 20% margin. When the main venture collapsed, that business kept me alive. It eventually became my primary company, which later expanded into two more.
That experience built the philosophy I live by now: stay small long enough to become big enough.
At one point, client applications were flooding in across multiple companies at once. I could have accepted everyone, outsourced the overflow, and collected commissions. The short-term revenue was real. But I wasn’t confident that other teams could deliver at the standard I required. One bad client experience can damage a reputation it took years to build.
So I intentionally slowed down. I focused only on the clients already inside the system. I avoided aggressive hiring because I didn’t feel experienced enough yet to manage a larger team well. The result: quality was protected, reputation was protected, and scale came when the system was actually ready to support it, rather than simply when demand was high.
Too many businesses grow faster than their internal maturity can support. I made a deliberate choice to let the foundation set before adding more floors. Some founders thought I was leaving money on the table. Maybe I was. But the businesses didn’t break when they grew, and that mattered more.
What Monday Actually Looks Like Across Three Businesses
People assume running three companies means spending mornings on big strategic decisions. Most of my Monday morning is operational.
The first thing I do after waking is a short pineal gland practice, about fifteen minutes. It clears my mind and sets the state for the day. Then a light stretch, a few things I’m genuinely grateful for, and a quick check of my phone: no emergencies, no client issues, everything running.
After that, I pay my employees.
The Payroll Practice Nobody Talks About
Every Monday without exception, I personally review and send every employee’s payment myself. We run on weekly payroll across all three companies. This is non-negotiable.
Most founders delegate payroll immediately. I’ve kept it intentional. It does two things. First, it forces me to stay connected to the financial reality of every entity I run. Second, it tells the team their work is seen. A founder who personally reviews and sends your payment communicates something that no HR system can replicate.
After payroll, I work through the highest-priority tasks across whichever company needs the most attention that day. I go to the gym. I come back and continue into the afternoon. Some days I’m deep in project coordination and strategy until evening. Other days I switch between calls and creative work. The rhythm changes. The foundation stays constant: meditation, payroll, gym, focused work.
What Automation Means at the Ground Level
Automation gets discussed in abstract, enterprise terms. Here is a concrete example.
My mother runs a bakery in Spain. Every night, she manually broke down all incoming client orders to produce a production sheet for the factory team so they knew what to bake the next morning. It took her thirty minutes of tedious, error-prone work, and required her to go to the office late at night to do it.
We built her custom software that reads the orders, processes the data, and automatically prints a ready-to-go production list each morning. One click. What used to take thirty minutes every night now takes seconds and never makes a mistake.
That is what operational automation means at the ground level. Real problems solved for real people. That same thinking, applied at scale, drives the infrastructure work we build through lean DevOps systems and the marketing operations we run through performance-led campaigns for clients across multiple markets.
The goal in every case is identical: make the business smarter, not just faster. Remove the friction. Let people focus on the decisions only people can make.
What’s Next
AliveDevOps is expanding into more automated, self-operating client environments. The long-term vision is infrastructure that maintains itself, where the engineer’s role shifts from firefighter to architect. I believe some of the most successful companies in the next decade will run with a fraction of traditional headcount, not because they cut people, but because they built smarter from the start.
Pabs Marketing is moving deeper into creator economy strategy, helping individuals and brands build sustainable digital presence rather than chasing short-term viral moments. The influencer space is maturing fast, and the operators who understand both content and business infrastructure will pull ahead.
And Pabs Entertainment continues building its position in live event production in Costa Rica, bringing the same operational discipline we apply across our tech and marketing businesses to an industry that demands precision. In live events, you cannot miss a deadline.
The broader philosophy across all three remains the same: build resilient, self-sustaining businesses, stay involved at the strategic level, and keep the foundation solid before the scale arrives. More of the thinking behind it lives at pablogerboles.com.
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Learn More
AliveDevOps: alivedevops.com
Pabs Marketing: pabsmarketing.com
Pabs Entertainment: pabsentertainment.com/en/
Pablo Gerboles Parrilla: pablogerboles.com
