The Playbook

Boring and Painful Beats Clever and Novel

Nobody's going to hand you a delightful growth channel. The winning ones are tedious, awkward, and exactly why they work.

← All articles · distilled from real founder research

Founders love a clever channel. Something novel, something that feels like a hack, something you can tweet about. And clever channels are mostly a trap. The tactics that actually built the businesses in every research file I've got are boring and slightly painful — which is precisely why they work. The awkwardness is a moat.

Consider cold email, the least sexy tactic in existence. Ryan Doyle and Jakob Greenfeld built Sales.co — a cold-email agency — by running cold email itself. They offered to run campaigns for a few companies free for a week, then stair-stepped the price: $500, then $1k, then $1.5k, then $2k a month. They hit roughly $10k MRR before the two founders had even met in person, and the business has been reported around $90k/month. Nothing clever there. Just the grinding, unglamorous act of emailing strangers and slowly earning the right to charge more.

Cold email keeps showing up because it keeps working. Jon Perrin got both his first and his tenth customer from Hunter.io — literally looking up email addresses and reaching out. Proxycurl's Steven Goh got his first ten paying customers from cold email, and even at the 1,000-customer mark, about 10% still traced back to that original cold-email blast. Boring. Effective. Years later, still paying rent.

Now look at painful. Some channels win because the product or the topic is uncomfortable, and most competitors won't touch it.

Squatty Potty sells a toilet stool. You have to talk about... bathroom mechanics. Awkward. But that's exactly the barrier they weaponized — the "This Unicorn Changed the Way I Poop" ad leaned all the way into the discomfort with humor and racked up over 140 million views, with sales reportedly running around 600% above projection. The embarrassment wasn't the obstacle. It was the whole reason the ad was shareable. Nightcap, the drink-cover scrunchie built by a teenager after a friend's drink-spiking scare, is another "hard to talk about" product — and it went to roughly 175 million views on TikTok and about $2.1M in sales the year after airing. Founders who run toward the awkward thing find open space, because everyone else flinched.

Then there's the plain grind of showing up in communities and being useful, which is boring in a different way — it's slow. Mateusz Buda built ScrapingFish partly by writing high-quality blog posts that repeatedly hit the Hacker News front page, then getting his first hundred by answering people's actual problems in Reddit, Facebook, and LinkedIn communities — with genuinely helpful posts, not links. That's tedious. You answer questions for weeks with no obvious payoff. But it compounds, and the "give value first, mention the product last" motion is the single most repeated winning move across every founder roundup I've read.

Starter Story itself is maybe the purest example. Pat Walls grew it to its first ~10,000 subscribers by posting entire founder interviews natively inside Reddit — the whole valuable thing, right there in the post, with only a tiny "more on our site" note at the bottom. And he made sharing real revenue numbers mandatory, because number-heavy posts performed best. That's not a growth hack. That's the discipline of being relentlessly, specifically useful, over and over, when it would be easier to just drop a link and run.

Here's why boring wins, mechanically: boring channels are unglamorous, so they're uncrowded. Everyone's chasing the clever viral loop; almost nobody wants to send a hundred personalized emails a day like Intercom's Des Traynor did, or answer forum questions for a month, or hand-stamp popcorn bags at a Brooklyn market like Pipcorn. The tedium filters out your competition. The pain of the topic filters out the squeamish. What's left is open field for whoever's willing to do the dull, slightly cringe-inducing work.

So when you're picking your channel, be suspicious of the clever one. If it feels fun and frictionless and tweetable, so does it feel to everyone else, and it's probably picked clean. Ask instead: what's the boring, effortful, mildly embarrassing thing that I could do consistently and most people won't?

That's usually your channel. It won't feel like a breakthrough. It'll feel like homework. Do the homework.

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