In 2011, designer Frank Chimero gave a talk called “The Long, Hard, Stupid Way,” and the title has stuck with me ever since. He describes it in a way that’s “painful and difficult,” that “looks a lot like toiling and worrying and starting over and scratching good ideas to look for better ones.” It’s the dedication, compulsion, and near-masochism of the artist who can’t resist doing it any other way.
I’ve realized that doing things the long, hard, stupid way can also be a strategy. For some things, what only matters is the end result, like renaming three hundred photos by date. But for others, what you pick up along the way is a major unfair advantage. The difficulty of doing it the long, hard, stupid way—especially if you consider others’ inability to do it the long, hard, stupid way due to ignorance, impatience, or any other factor—can be a moat.
One of the main pillars of my coaching program for agency owners is that you have to send pitches to prospects every day. I think it’s very hard for agencies to exist long-term without this unless luck is on your side. I suggest sending five pitches a day as the bare minimum, with a hundred a day being the bar to meet.
Almost every agency owner I tell this to is shocked at the magnitude of that challenge. Where are they going to get a list of 100 people to pitch, much less 100 people every day?
99% of them try to automate it immediately. They look for existing lists they can access or purchase, sign up for LinkedIn scraper tools, or try to feed an AI tool a list of parameters to cobble the list together for you. And sometimes, it even works pretty well.
But the next time they need an updated list, they’re just as lost.
I suggest a different way to go about it. I tell them to Google around for companies in their niche they think they could help, find a person who works there that’s most likely to want to hear from you, and add them to an Excel spreadsheet.
Wait, did I say Google? Surely, I meant a Claude or ChatGPT prompt, right? And an Excel spreadsheet? Wouldn’t a Trello card or Linear ticket make it easier to kanban and track through stages?
Nope. I did mean Google search and a plain old spreadsheet. It’s the long, hard, stupid way.
Why? Because only after you spend hours or days making this list, contacting people on it, watching the replies, and assessing the quality of each do you realize that your most promising conversations happened with the people at companies you found listed in that one obscure Wall Street Journal article you paid $2 to access because of the paywall. You would never have figured that out if you automated it. Your fancy vibe-coded list aggregator tool probably would have moved on at the first sign of a subscription fee.
The most valuable part of getting an outreach list isn’t the list. It’s learning where to look.
We’re quickly getting to the point where we can automate anything. Sometimes, that’s the best reason to do it the long, hard, stupid way.
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