#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 ↗Agency Operations

How do you plan your time for planning and filming videos for your main channel while balancing your agency, coaching, and content creation? I'm struggling to manage content output, client work, and scaling my coaching business. Could you share your planning and balancing approach?

I’m hitting the upper limits of what one person can realistically handle with my current level of systematization. I keep seeing situations where a better way would exist, but I don’t have time to figure it out, so I push through at a less effective level. I ran into the same issue with my agency—I know there must be more leveraged ways to do the same work without hiring another team member. Pragmatically, I’m at about $2 million a year in profit, which feels like a reasonable ceiling for someone trying to juggle an agency model (which is less profitable per unit time), a main YouTube channel, and other content‑production mechanisms. Even with good time management, that seems to be the upper limit for one person. To give you a behind‑the‑scenes look: I usually start with the video idea, then the title and thumbnail, because those drive performance. I source ideas from YouTube comments using a comment scraper, turn them into titles via templates, then think about a thumbnail (though I don’t over‑think it—content matters more). I’ll sometimes leave a silly clip at the end, but I focus mainly on production. Logistically, I get the ideas into the pipeline, then filming is straightforward: I turn on the camera and talk for an hour or two, sometimes following a strict outline, other times just using my tablet and pen because it’s more time‑efficient.

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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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