How do I get in contact with people who make big‑ticket decisions?
It's fairly straightforward: you contact big‑ticket decision‑makers the same way you contact anyone else. These people have less time, so their threshold for what deserves their attention is higher—think of turning up the difficulty in a game from medium to hard or extreme. It's still possible; many people succeed at extreme difficulty, though it's a bit harder overall. Their main concern is the extra marginal time they'd have to spend managing you to get a project from start to finish. New business owners often think the amount of money is what matters, but it's really the value you provide and the time that value frees them up. Beginners might say they'll work for free or do anything, but high‑level executives don't care about that; offering marginal value would actually cost them more time than it's worth. The way to pitch them is to make them certain that working with you won't consume any more of their time—that you're 100% self‑managed and will immediately solve a direct need that's currently costing them money, on which you can deliver multiples. It's not about offering to work for free or cheap; instead, you say, 'Hey Pete, I know you're suffering from XYZ problem because I've worked with a big name trying to solve it before—it cost them $48 million a year (or $400 k a year). We've solved it and made them $1.5 million. I've already started working on this for you. I know your time is valuable, so this requires no supervision. I've already eliminated XYZ % of this leak, and I want to continue doing this for you. If I do, you're likely to make this much or that much money. All I'm asking for is a simple okay from you, maybe a 10‑minute call to shake hands and orient you. I'll have no ongoing management costs and am entirely self‑directed. You can think of it as you spending just 5 or 10 minutes of your time and receiving a fix for a $40‑$50 k/month problem. People love this approach because it shows you understand how many directions their time is pulled into. My recommendation: pitch anyone whose problem is worth over half a million dollars a year—which really isn't that much when you think about it.
Think about it from my perspective — I'm already making a lot of money and don't need more talent, so the only way this becomes worth my while is if you do all the work for me upfront. Identify a specific problem I'm suffering from that's costing me money, solve it, and package the solution so all I have to do is click one button — don't make me come up with the problem, the solution, or a management structure for you. Don't pitch like 'I'd like a job, I'm feeling lost' — instead, put yourself in the shoes of the person you're reaching out to, understand what they're actually struggling with, do all the work, then present it: 'I think I can make you this much money — all you need to do is respond with X, Y, Z. Say yes and I'll get started immediately, you can pay me after it's done.' That's how you pitch working for someone for free. I'm good right now and probably will be until $300-400K/month, but when I am hiring again, the people who've engaged with my content will be the first I look to — you can copy this approach for other people too.
When you approach somebody in my position asking to work with them, you can't just hand over a list of your CV — a CS degree, sales experience, following me for a while — that's not inherently compelling, and nobody will tell you this unless you're in a position like mine: when someone says 'can I work with you, I'll even do it for free,' that's not valuable to me, because money isn't the constraint right now, results are. There's a tier list for this kind of pitch. C-tier: 'I want to work with you for free, here are my skills' — the problem is I still have to do the labor of figuring out where you fit in my org, which takes time and energy and isn't sexy. B-tier: 'I've already done some work for you for free, here it is, can you fit me in somewhere?' A-tier, the best: 'I noticed you're leaving X on the table, I already fixed it for free, I want to keep fixing it and I'll charge you a fraction of the value it creates — this takes zero time and energy on your end, I'll manage it all myself.' The reason A-tier wins is I don't have to evaluate you (you've proven it), don't have to place you (you've already found where you add value), and don't have to manage you (you handle it yourself). In any situation where money isn't the bottleneck and results are, this is what you want to do when approaching anybody bigger than you — show up as a self-starter who's already solved a problem for them.
If you’re earning $2,500 per year, you’re essentially being robbed in broad daylight; but if you’re making $2,000 per month ($24k per year), you’re on the lower end yet not necessarily being exploited. To think about your situation, imagine you’re paid $25,000 per year while generating $500,000 in value for the YouTuber—that’s about 5% of the value you create. Most people receive only 1–2% of the value they generate, while strong salespeople earn 15–20% through commissions. My advice for contractor‑partner roles like yours is to aim for 10–15% of the value you deliver, which translates to roughly a 10× return on investment for the client. If the client is smart, they’ll happily pay you $1 to make $10 for them. The mistake many people make is realizing they’re underpaid and then demanding more money outright—a losing approach that comes across as a loss‑based demand and triggers ego or risk‑aversion in business owners. Instead, frame the conversation around growth: remind the client of the results you’ve already delivered (e.g., over $3 million generated together), share your vision for scaling to $10 million, $20 million, or $30 million, and propose a concrete roadmap (start with X, then Y, then Z). Emphasize that you want to take on more responsibility because you believe you can execute better than others, and assure them you won’t take any of their time. Then, at the close, add that you want skin in the game—more upside when things go well, and a corresponding adjustment when they don’t. Present this structure directly to the client. Because you’re leading with growth and a clear path to multiply their business, the likelihood of them agreeing to partner on a new initiative is vastly higher than if you simply complained about pay. In short, if you’re only making a few thousand dollars a year, you are being underpaid; but if you’re earning tens of thousands per month, you’re in a reasonable position. My overall approach to every job or partnership discussion is to focus on mutual growth, not to threaten to walk away unless paid more—that’s blackmail and damages trust. Successful business owners refuse to negotiate with that kind of pressure. When you approach from a desire to grow the pie together, you’ll achieve far better outcomes.
The simplest and easiest way to run a discovery call: somebody comes on, do your building rapport, make them happy, make them smile for a second. Then say, 'Hey, I know we've got a lot to cover, so I'd love to get into things. Here's how these calls typically go — I start off asking you some questions about your business. After that, we'll make sure there's a fit mutually on both sides. I'll walk you through the solution we have for you and how I think it could apply to your particular case. And then if it makes sense, we can chat about next steps. Does that sound good?' Then the first question is: why the hell did you take the call? You probably get brushed by 50 of these emails or Upwork applications or LinkedIn DMs per day — what made you want to jump on this one? That's literally all you need to kick off probably 80% of the call. The reason is: one, you're building rapport so they hopefully like you a little bit. Two, you're setting an agenda for the call, which is important because now the customer knows you're in control and understands where things are going and what's coming next. Three, you literally just ask them straight up, 'Dude, why are you here?' and they'll tell you, 'I'm here because my business is really struggling with XYZ and I was considering this solution and thought I'd give it a try.' Fantastic — they've given you the ammo you need to shoot them later. It's a shitty analogy, but they've given you everything you need to close it and make it a win for both sides. Just ask that question first and your sales calls will immediately go three times as good. Then later, after they tell you what they want to accomplish, ask, 'Have you done anything to try and get to the solution before?' If they say, 'Yeah, we hired somebody 3 weeks ago and they weren't really good,' ask 'Why weren't they good?' — 'Because of X, Y, and Z.' Now they've given you everything you need to close the call and everything you need to avoid too — just don't do what those guys did and you're good. People overcomplicate the sales process and end up talking about themselves for hours. You don't need to make it anywhere near that complex to achieve what both parties want: someone has a problem, and you come in and solve it.