How do I know if I'm hitting the hammer right when starting an agency? Should I spend time looking for projects or learning the skill first, or a combo?
He says you first need to anchor what a lot of money means. AI automation agencies have the lowest barrier to entry and lowest capital cost—comparable to website design agencies in the late 1990s or social-media marketing agencies in the early 2010s. In this space, a lot of money is probably just a few hundred dollars. Any business outside this vertical will cost significantly more than a few hundred to get up and running over a three-month period, so you should expect to spend money to make money. Regarding your specific situation—bidding for email-setup projects on Upwork—lack of experience isn't a time issue; it takes only a couple of weeks to become proficient with any tool well enough that someone will pay you to save them time. So you should combine learning and prospecting. He recommends doing Maker School's introductory automation agency tutorials to gain foundational knowledge and learn to read the language of the tools. Once you understand the language, you can communicate with AI, use Google to find answers to specific questions, and you don't need to know how to do everything right away. The key question is whether a future version of you could solve this problem in the next couple of weeks—and the answer is almost always yes.
Great question, and congratulations on the upcoming baby. If you're asking whether to take a job doing AI implementation for agencies or start your own freelancing AI implementation business, I'd recommend the freelancing route. You'll have far more freedom and flexibility over your schedule, even though you may need to outwork the alternative in the short term. In the long run, owning your time is a major part of what I enjoy discussing. Acting on knowledge is more important than just learning it. In Maker School, many people in your situation—working a stable job but wanting something more—find success through daily consistency: build an outreach habit where you connect with business owners who might need your services, and repeat that effort virtually every day. Over six months, that's about 180 days. Doing 10 unique, high‑quality custom outreach pieces per day yields roughly 1,850 touches. If those pieces are truly high quality and unique, the chance of not getting at least a 2‑3 % booking rate is very low—2 % of 1,850 is about 36 meetings. It's also unlikely you'd fail to turn at least one of those meetings into a paying client. If you really want to get started, just throw the kitchen sink at it: use every tool and tactic you can to generate leads and demonstrate value.
AI will create ads, films, and music videos much faster and for far less money—no production or audio teams needed, as the AI handles scripting and auto‑fixes everything. The output comes from natural‑language prompting; those who know how to prompt the models will do best, though that skill will fade as models become better at prompting themselves. You can definitely earn $10k/month with this right now, maybe for a couple of years. I’m still a beginner in AI automation agencies, but I know some basics and have built a few automations. Your next step is to get in front of paying customers, articulate their needs and problems, and show how your solution helps. There’s no other path—it’s messy, like entering a gladiatorial arena with tigers; you have to win your first fight to earn praise. Start by signing up on Upwork or freelancer.com, treat yourself as a low‑paid API endpoint, gain experience and money, then move to cold email, ads, or other channels to build a sustainable method.
Accept any and all work on Upwork—think of it as an elevator that instantly connects you to large businesses you’d never meet otherwise. Even as a total newbie, you can land a client doing $10–$20 million a year within a week, giving you a powerful case study like 'I helped a $10 million/year business achieve X, Y, Z.' At this stage, don’t worry about qualifying or tightening the funnel; go broad to bootstrap experience, collect case studies, and start making money. The creator shares a personal example: a friend who jumped on Upwork while he was door‑to‑door went from zero to a legitimate $30 000/month income in three‑to‑four months by maximizing opportunity and landing a big‑ticket client whose needs matched his skill set—something the creator missed while grinding door‑to‑door for $5 000/month.
First, I’d join a community like Maker School—not just to use my own products but because membership gives you deep discounts (often a 10x return) on AI platform credits and payment‑processing fees. With those savings I’d start by learning a visual drag‑and‑drop automation builder (such as the n platform) for about four to six hours; that teaches you the fundamentals of systems, workflows, JSON, HTTP requests, etc., which accelerates everything else. Next I’d spend another four hours on a Claude‑code course that covers the technical setup, agent communication, model selection, and so on—roughly ten hours total. After that foundation, I’d devote virtually all remaining time to acquiring customers; the first 90 days would be less than 1% spent on learning and the rest on outreach. You need a customer to actually enter the arena, so I’d use Maker School’s day‑by‑day accountability to hit call and outreach targets, then loop back to upsell from any lower tier to higher ones as the relationship grows.