#109 · How to make AI automation into a lifestyle business

youtube ↗Cold Email

Should I show the full workflow in my Loom video, or just the trigger and results to avoid copying?

Well, let me ask you: I show everything I do for my own businesses all the time, and you guys copy it. Does that really devalue my work? Only marginally, and I operate at a much larger scale than you. Showing 20 people a month the systems you build won’t meaningfully impact your ability to do business. So, drop the mindset of gatekeeping systems or knowledge—that won’t help you move forward, Kendra. The fact that it’s not scalable is actually good; I recommend you focus on the things that don’t scale. Many people hesitate to do non‑scalable work, thinking it’s low‑leverage, but until you’re making about $50 k a month, pretty much everything is high leverage for you to do yourself. So, do this yourself: send personalized Loom videos and show the full workflow. It’s not scalable, but you should repeatedly practice speaking about your product. If you want a concrete example, I’ve recorded a step‑by‑step video on how to set up Loom for agency sales—check it out; it’ll put things into perspective.

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Related answers

youtube ↗Lead Generation

Alex asks: I'm brand new on Upwork with zero reviews and no reputation. My competition already has solid reputation, so I feel I need to bring everything with my proposals to get a reply. I've been spending about 30 minutes per application—recording a Loom video, building an N8N workflow, making a diagram—and planning each project beforehand. At your recommended 10 applications per day, that's 5 hours just on applications. Am I overdoing it, or is this normal? How can I tighten the process without sacrificing quality?

This is a core part of my Upwork outreach advice. Start by creating a high‑quality asset—whether it's a detailed Google Doc proposal, a spreadsheet, a workflow chart, a Loom video, or any combination. When you're brand new, building a workflow that solves a client's problem will take time, but after you've built 10 or 20 of them you won't need to start from scratch each time. You can reuse the closest previous workflow as proof of your ability, which eliminates the workflow‑building overhead and leaves you only to record the video. Recording a video after you've done a few dozen takes exactly the length of the video—if it's three minutes, it takes three minutes to record. So the process drops from ~30 minutes per application to about five seconds to pick a workflow, plus two to three minutes to record and send, bringing you to five or six minutes per application. At that rate you can comfortably do ten applications in an hour.

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youtube ↗Agency Operations

When creating Loom videos to solve a client’s problem, how do you plan them out? Do you always follow the same process?

I usually create Loom videos the way I’ve always done: I find it more scalable to move fast and break things rather than spending a lot of time mapping out a detailed workflow. I’ll open many tabs, jump straight into the solution, and just start recording, often saying “Let’s do this.” It’s a bit of a “Leeroy Jenkins” approach—just dive in and iterate as you go.

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youtube ↗Marketing

I run a short-term rental business on 9 acres, starting to document the journey at $20K/month in a similar format and I can tell you used AI a lot for a lot of these. Is that necessary?

Well, the big thing is how much money you're making right now. If you're already making $5-10K a month and have something worth talking about, then it's worth making videos. If not, don't waste time documenting—focus on actually succeeding with the business. Social media is a massive distraction; it's easy to fall into a narcissistic loop of checking impressions and tweaking gear, which is wasted effort unless you've already achieved financial success. Nobody cares about your journey until you've made it, so documenting before that is mostly wasted time. If you do become a big success (e.g., making a million a month), then you can post your first video and build a brand. Aside from that, I’ve been checking stats: my main channel grew 43% in the last 24 hours to 19741 subscribers, Instagram audio glitch aside, Maker School is up to 2111 members, etc. I also realized my earbuds mic got water‑damaged, so I’ll replace them with cheap earbuds and use compression to clean the audio. Finally, I’m going to get breakfast, moisturize, and crush the day.

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youtube ↗Agency Operations

How much time do you spend on client work now versus at peak?

At peak, client work consumed the overwhelming majority of my probably 50-hour weeks - everything from front-end to fulfillment, backend, client relationships, management. Now I have a partner who takes on the vast majority of the work. I'm still figuring out my role; I think focusing on the front end makes most sense, and we've been doing sales calls to shape that. I don't need to transfer my time into the business because my main leverage is distribution and the established value I've built. Instead, I'm looking for the highest-leverage actions: recording a short Loom video that welcomes prospects, answers preliminary questions, and then spends time edifying my partner, who I position as the perfect person to handle delivery. These videos take about five minutes, are the first point of contact, and can eventually generate a high LTV (e.g., $500k) if executed well. This lets prospects get an advisory impression from me while the partner fulfills the work, solving buyer's remorse early.

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