The Rule of Two: How I Automate Like a Madman

In my consulting work, I come across many leaders and entrepreneurs who are swamped in mundane tasks because they don’t know how and when to streamline their businesses.

As a result, they don’t have the bandwidth to think strategically - to steer the ship, avoid icebergs and get to the destination with a happy crew and customers.

Worse, beginning new projects without thinking about automation and delegation sets you up for eventual failure as the manual effort and focus drain compounds as the business grows. So many projects land in the graveyard simply because they run out of steam.

What if we could adopt an automation mindset from day one?

Math Inspired, Battle Tested

In my quest to transform ideas into tangible outcomes as quickly as possible with minimal chaos, I've developed the Rule of Two — an execution strategy inspired by mathematics. Just as you need only two points to form a line, so too do I use two successful data points to form new processes.*

What does this mean?

Simply put, after successfully carrying out a new task twice, I start documenting a process that can be delegated. Just two instances provide enough evidence to consider automating parts or the entire workflow.

If you don’t automate, your odds of success actually decrease the faster your project grows! The Rule of Two sees repetitive tasks through scalability lens—it’s not just about how but when to automate.

Let me illustrate this framework with how I automated the Mind Map Gurus workshop series—my podcast project with 10 steps across 10 platforms totaling 15 hours per session—not including the actual interview time!

The first time I tackle something, I do it myself. By the second go-around, I'm already spotting patterns and (in)efficiencies. Therefore, the first two episodes were grueling solo missions aimed at understanding each step intimately.

By the third episode, I’m documenting in Notion as I go along, creating a one-click template of all the major steps and fields required to put a show together from scratch. On my fourth try, I’m teaching these steps to my operations specialist.

Before you know it – by iteration five – my hands are off the wheel. Automation has taken over and the car’s driving itself.

Mind Map Gurus is a podcast series with 10+ steps across 10 platforms. Without automation and delegation, I could easily sink 20 hours into each episode, making it unsustainable as a side project. I use Notion Kanban boards and templates to coordinate the process with my team.

Streamlining Operations - Kaizen Style

The beauty of having a process in place is that it opens you up to further automation of subcomponents with technology.

Take our post-discovery call email sequence. After I get off the phone with an upcoming guest, I send them a Calendly link that triggers a sequence of personalized communication to gather speaker info and send interview tips without any manual work from my team.

Because I’m running four other businesses, if I hadn’t intentionally planned for automation, I would’ve quit the Gurus project long ago. Instead, we’ve now had 8 successful shows and I’m strategizing on how we can improve the next season of the series, all without worrying about the burdens of operating the venture.

At its core, the Rule of Two embodies a mindset shift towards intentional streamlining from the very beginning. It sets us up for sustainable success with more fun and a lot less stress.

*This is the same process I use to create new mental models. Two occurrences of a peculiar phenomena are sufficient for me to hypothesize and create frameworks based on empirical evidence. I then stress test the new mental model against past and new experiences by assessing their explanatory or predictive power.

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