#15 · Building an AI Upwork Agent

youtube ↗Mindset

Can you explain your hourly-log feedback loop framework, what you measure, why, and how you use it to reduce distractions?

I don't have an automated feedback-loop system. Instead I keep a simple deliverable tracker where I jot down the tasks I completed in the last hour—a method I adopted after Matthew Larson recommended it. I log the hour of the day, the timestamp, and exactly what I did. Periodically (about once a month) I review the sheet to see whether I spent my time in the most effective way; for example, after getting a new camera I spent two hours organizing my studio, which felt worthwhile. If the retrospective shows the time was well spent, I continue those tasks—it acts as positive reinforcement. I deliberately avoid automating this reflection because analyzing how you spend your time is one of the highest-leverage actions a person can take; outsourcing it to a 'middling intelligence' would miss the nuance and emotional buy-in that comes from being intentional about life optimization.

time trackingproductivitydistractionsfeedback loop

Related answers

youtube ↗Agency Operations

I think you do a lot of tracking and logging like your end learnings in a sheet or another video. I'd be really interested in hearing more about that.

Sure. I use a deliverable tracker. I haven't used this personally, but here's how it works: each hour I note what I accomplished—e.g., created a hiring pipeline, updated a content calendar, added templates, etc. I let AI itemize it into a big sheet. The tracker lists all expenses and tasks, so I can quickly see what I did in the first hour, second hour, and so on. It serves as an accountability metric and I share it with others for transparency.

trackingdeliverableautomation
youtube ↗Mindset

How should you handle time blocking when tasks take longer than allocated, and how do you structure your daily schedule?

Rather than strict time-boxing, structure your schedule by front-loading your highest-ROI, nearest-to-revenue tasks first and taking as long as needed to complete them. For instance, replying to community comments in Maker School directly drives retention, revenue, and goodwill, so it is completed first thing every morning. To speed up execution over time, record yourself completing a recurring task, review the footage to strip out wasted effort, and establish a realistic 'ideal time' benchmark. Track your time daily as a KPI until you consistently reach that benchmark. The key to productivity is productizing your daily schedule—repeating the exact same core high-value actions every day so you build speed and mastery, rather than constantly switching between contextually different tasks.

time managementproductivitytime blockingdaily routine
youtube ↗Agency Operations

How do you keep track of everything on your own with client projects, students, and promises, and doesn't it get overwhelming?

Yes, it definitely gets overwhelming; I have overwhelming days like anyone else. Even the big business titans I admire have extraordinarily overwhelming days, though they hide it well. The feeling of overwhelm exists on a gradient between no stimulation and overstimulation, with an optimal middle spot where you're optimally stimulated—this is the ancient Greek concept of ESS (optimal performance zone). On a stress‑meter graph, the sweet spot is where stress brings out your best performance; high performers operate there, while being over‑stressed (distress) is too much and harmful. I often feel overwhelmed and admit my project‑management systems aren’t the best, but I’m working on them. The key idea is to treat your limited daily time as a constraint and use it for good—find ways to do the same or more work in the same or less time rather than seeking more time. I appreciate the question and note that many one‑person businesses make more money than I do, so I look to adopt their systems. Simple systems that keep things on track are a big lever; publishing content every day is one of them, letting me answer questions and create content simultaneously—killing two birds with one stone. When a student asks a question, I record a video to answer it and also produce content, always looking for opportunities to combine tasks. This approach yields more creative output, a stronger content strategy, and higher volume—a tactical way to work.

project managementoverwhelmsystems
youtube ↗Agency Operations

Can you walk me through your actual daily routine?

I wake up between 5 and 6 a.m., letting nature wake me instead of an alarm to avoid adrenaline spikes. First I check my higher‑ticket community (Make Money with Make) and respond to any recent activity—either writing text posts with Aqua dictation or recording custom Loom videos that solve members’ problems. I repeat the same process for the Maker School community, which usually has more roast requests because it’s larger and full of beginners. After that I take a call—either a community call, a coaching session, or a sales call—usually between 8 and 9 a.m.; if it’s at 8 I sometimes get cut off, but at 9 I can finish my prep work beforehand. Once the call ends I’m warmed up and I record the daily updates video. After the video, if I have content for the main channel I film it, then the rest of the day is agency work: reviewing new LeftClick clients, drafting proposal templates, recording Loom videos for prospects, discussing strategy with my business partner Noah, and working with a developer on our website revamp. I finish the day with lower‑value tasks. I order my workflow this way because I start with the activities that generate the most revenue and move down to those that earn less, ensuring I always hit the high‑impact items first.

daily routineworkflowmake moneymaker school