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#343 · how to get good at sales (just start)

youtube ↗Sales

How did you get good at sales? Should I just start selling with what little I know, or learn the tech first?

You just start. The only way out is through. You do not need to know a specific platform, tool, or piece of technology, although obviously that helps. The reality is when you sell, you're only ever selling in the space of ideas anyway, so you can sell an idea the same as anybody else with any level of technical skill. What it really is, is putting the words in the right order and understanding, at least to a foundational level, why people make purchasing decisions. Some good books if you want to learn more: Influence by Cialdini, Never Split the Difference by Chris Voss, and Pitch Anything by Oren Klaff — probably my three best sales books out there. If you want a wild card, try When I Say No, I Feel Guilty — written 50-something years ago, it's about how to get over routine social inadequacies around asking for what you want and being assertive. So no, you do not need to know a specific tool stack or piece of technology in order to sell. All you need to do is go out there and sell. Learn the skill of selling and it'll work for whatever product you end up selling.

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Related answers

youtube ↗Agency Operations

As a founder juggling content, sales, and staying technical with AI, I hired someone for content to focus on sales but wonder if I'm spreading myself too thin. Can you help?

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.

delegationtime managementfounder
youtube ↗Client Acquisition

As a beginner in automation/services, what steps should I take to make my first sale?

For your first sale as a beginner in the automation/services space, the most straightforward approach is to go on Upwork and similar job platforms and try to land a paying customer as soon as possible, even if the pay is low or the scope is larger than you'd usually handle. The lifetime value to cost‑per‑acquisition ratio on Upwork is very favorable — roughly a gross‑profit‑to‑CAC of about 10 : 1, making the economics strong. Think of it like online dating: the platform has already filtered people who are looking for what you offer, so you just need to show you can deliver. Focus on proving you can 'juice' the work and stand out among the many freelancers. Even small, low‑paid jobs build reputation and lead to better opportunities.

upworkfreelancefirst salecac
youtube ↗Mindset

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.

analysis paralysisniche indecisiontaking action