I keep circling around who and what to sell, which distracts me a lot. I have the most experience in content automation and a background in content marketing/editing, but when I try to move into selling, I get stuck again on who to sell to and which outreach method (Loom, bids, email) to use. How do I get out of this rut?
So many people struggle with this because they think what they're selling matters more than who they're selling to — but honestly, being stuck on 'what to sell' is the same underlying problem as being stuck on 'who to sell to.' The reality is it doesn't matter that much what you sell or who you sell to in the abstract — you're never going to figure this out ahead of time by thinking about it, you only find out by starting. I could give you a list of things to do, but it'll be invalidated in two months because the market moves fast. The only real way to know is to throw a bunch of things at the wall and see what sticks — put together some offers and get them in front of real people. Right now you're working entirely off opinion; you have to actually make progress (e.g. sending something like 100 Loom videos, which is doable) before you'll ever get real data on what works.
Your content is your sales, so hiring someone to handle the most important task doesn't make sense; instead, consider delegating operations, fulfillment, or administrative work. In general, delegate any work that isn't essential to your bottom line to buy back your time—a concept Dan Martell emphasizes. Use that reclaimed time to focus on activities that have a direct one‑to‑one correlation between time spent and revenue, like high‑value sales or product development. You might worry about remaining just the sales guy while others become more valuable to larger companies, and while you're strong at marketing and getting attention, your sales still need improvement. The valuable skill is maintaining client relationships and providing daily progress updates; doing so preserves the relationship and sharpens your most valuable abilities. You're overthinking the situation—you're stuck in your head. Stop spending time on this problem; put your head down, resume the daily outreach and marketing activities that got you meetings, and repeat them all day. These concerns are largely self‑created; you are your own biggest obstacle. Getting out of your own way will unlock far greater progress. I’ve experienced this myself over the last seven or eight years: progressively removing my own limitations has been key to my success. Okay, it's Clark's as I am. Thank you.
I may or may not have had breakfast—I saw evil while trying to build a SAS business and a new short‑form video editor. For marketing outreach, start by building distribution. If you have distribution, you can launch any business and instantly have a pre‑validated audience interested in what you offer. Focus less on the product itself and more on building interest, eyeballs, and marketing. Try every social platform (YouTube, Instagram, TikTok, etc.) and outbound tactics like contacting companies that publish content regularly and offering them a group trial discount. Keep iterating through these methods until you get traction.
But anyway, how do you acquire more upmarket clients? I mean, I wish I could say there's a special system for upmarket clients. A lot of them tend to be more referral-based and gated. They won't take you seriously unless you can accomplish the first hurdle: finding a plausibly deniable reason to reach out to them. That means perusing the network of the people you want to get in touch with, making preliminary introductions or leveraging relationships, then using those connections to find your way to an intro. That's a big thing, but it's very manually intensive and not something you can automate. Aside from that, it's really just the same thing: sending cold emails and working your way up a decision-maker chain, delivering exorbitant value upfront. They're more bureaucratic, with longer sales cycles, but that doesn't mean they're impenetrable. Many cases exist of people in Maker School with zero experience who throw enough outreach to get the attention of a mid-level SVP or similar, then use that to ramp themselves up to a $25–$50 million per year business. It's uncommon, but it occurs.
It's a common problem for beginners to spend too much time thinking about the business model instead of actually doing it. You're likely stuck in your head wondering what niche to pick, how to reach people, and which platforms to use. Rather than overthinking, you should test an idea in the market. Pick three things: choose an outreach minimum per day on platforms you have experience with—like DMs on Instagram, X, LinkedIn, communities, Reddit—and run it for a month without changing anything. After 30 days, if you do about 10 pieces of outreach per platform, you'll have contacted nearly 1,000 people, giving you real data to inform your next step. For example, you might find that your web development offer converts at 2.9% while your cyber offer doesn't perform as well, letting you focus on what works. This approach turns you into a scientist of your own life, gradually carving out the solution space and increasing your chances of success.