[3Qs with AI CoE] Guest Rahul Subramaniam
The “One Week” Horizon & The Art of the $10 Million Dollar Day
Most podcasts are 45 minutes of fluff wrapping 5 minutes of insight. We skip the weather, the “how are yous,” and the generic bios.
Welcome to 3 Questions with Trilogy AI Center of Excellence.
The rules are simple: I ask the guest three rigorous questions based on their actual work. They ask me zero to three questions back. We are done in 15 minutes.
For this episode, I sat down with Rahul Subramaniam. Rahul is the Chief Technology Officer at ESW Capital and the Founder of CloudFix, where his team automates cost optimization across 40,000 AWS accounts. He is a "technologist at heart" who hosts the AWS Made Easy podcast and serves as Chief Mentor for Trilogy Innovations. Despite this massive strategic scope, he still finds time to ship code and build internal tools like Claude Dojo in a single weekend.
![[How-To] Claude Dojo, Cú Chulainn](https://substackcdn.com/image/fetch/$s_!j9O-!,w_140,h_140,c_fill,f_webp,q_auto:good,fl_progressive:steep,g_auto/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F5e6054fc-e2fc-43aa-8337-21f95ad8ffb3_2284x1488.png)
Here is what we uncovered.
1. The Dollar-Value Filter (Order of Magnitude)
I asked Rahul how he manages his time given his insane scope. His answer was mathematical. He realized early on that he has the same 24 hours as everyone else and a hard cap on his capacity.
His strategy is to maintain a cumulative list of tasks that grows by 7 or 8 items daily but he ruthlessly filters them down to just three executable items. To do this he uses a Dollar Value Framework.
Spiky Point of View: “Prioritization generates the highest ROI when you ignore precision and focus entirely on rough order of magnitude.”
Rahul argues that the goal is to identify the massive gaps in value. The only way to normalize tasks is to attach a rough dollar value to the outcome. He focuses on the magnitude. Is this a $1,000 task, a $10,000 task, or a $10 Million task?
Spiky Point of View: “You only have the capacity to execute three meaningful things a day so they must be the highest leverage items available.”
If he spends an hour unblocking a star engineer who is working on a $1 Million problem that hour is worth $1 Million. If he spends that same hour fixing a minor bug himself it is worth $100. By re-evaluating this list every single morning he ensures that his limited bandwidth is always deployed on the highest-magnitude items.
2. The “One Week” Horizon (Agile Execution)
I asked Rahul about his scoping process. Instead of relying on 12-month roadmaps Rahul focuses on immediate clarity. After 25 years in the industry he admitted that his maximum visibility for precise estimation is “about a week at max”.
Spiky Point of View: “The maximum resolution of a project roadmap in a high-velocity environment is exactly one week.”
Rahul operates on a Daily Re-evaluation Cycle. He course-corrects every 24 hours based on what he learned the previous day. This allows him to adapt to unknowns instantly rather than waiting for a quarterly review.
Spiky Point of View: “Daily course correction optimizes execution because it compounds learning at a 24-hour cadence.”
He applied this to Claude Dojo which acts as a tool he built in just two days. He used the Pareto Principle to extract the maximum value in 48 hours by getting the core features and task queues working. He stopped there because moving on to the next “$10 Million” problem yielded a higher return on time.
3. The “Bad Manager” (Hiring for Autonomy)
I asked Rahul what he looks for in an employee. He started with a stark confession. “I personally consider myself as a terrible manager”.
He uses this self-assessment to drive a specific management philosophy. He hires people who do not need to be managed and focuses entirely on enablement.
Spiky Point of View: “Smart people thrive when you define their objectives and unblock their path, not when you manage their time.”
Rahul believes that his primary role is to define the “Why” which includes the clear objective and requirement and then get out of the way.
Spiky Point of View: “Technical leadership is about treating direct reports as peers who need clarity, not subordinates who need instructions.”
He openly admits to his team that he doesn’t have “superpowers” or visionary foresight. By treating his team as peers he invites them to articulate problems for him. This often reveals that their definition of the blocker is sharper than his own and creates a culture of mutual problem-solving.
4. The Estimation Muscle (Parallel Processing)
Rahul closed with a tactical insight on how he executes those three daily tasks. He processes them in parallel to ensure consistent output.
Spiky Point of View: “Parallel processing provides the necessary hedge against getting stuck on a single priority.”
If he blocks off 2 hours for a task and hits a wall he switches to the next item. This ensures that every day ends with at least one “win.” But more importantly this daily repetition builds a critical skill called Estimation.
Spiky Point of View: “Estimation is a neural network that strengthens through daily repetition and feedback.”
Rahul estimates his tasks every morning and checks his accuracy every evening. That is 1,000 reps of feedback annually. This rigorous daily training loop allows him to size up a massive project in seconds because he is constantly calibrating his judgment.
Watch the full 12-minute session below: