A year after quitting his job, Alex is living the dream and quietly miserable about it. He is stuck in the $1,000s per month and desperate for the single order-of-magnitude jump that would change his life forever. The lever finally arrives, but not from the strategy he spent a year building. It arrives from a stranger’s blog reply and a business model he was certain was beneath him.
The productive-looking way to stay stuck
The most dangerous work is the work that looks like progress. Alex spends a full year pouring himself into SEO as CyberLeads’ second channel, the thing that would finally make the business “safe, stable and scalable.” The scoreboard at the end is brutal: one million impressions, tens of thousands of visitors, twelve months of effort, and five customers. He sometimes gets five customers from a single good tweet. Running the numbers, he realises he grew roughly $1k/month since quitting, growth he suspects he could have matched by spending ten minutes a day scheduling a tweet.
The verdict he reaches is the sharpest idea in the book: it was all pretend work. He thought he had killed his perfectionism, but it had simply learned to disguise itself. This time it wore the costume of responsibility, telling him he was eliminating his last single point of failure by building a second channel. The SaaS database rebuild is the same trap in miniature. A month of building, two weeks of silence, one customer on the final Sunday, and that customer turns out to want the newsletter he already had, plus a bug and a refund. The lesson is not that SEO or SaaS are bad. It is that a clever, top-down story about why an activity matters is exactly how perfectionism smuggles itself back in and keeps you busy going nowhere.
The shotgun: many cheap shots, no favourites
Once he admits he is lost, Alex changes his whole method for finding growth. He describes it as bringing out an old friend, the shotgun: run many experiments, fast, with low expectations, and refuse to fall in love with any of them. Stop thinking top-down, stop trying to be clever, switch to “artist mode” where anything goes.
The results read like a graveyard, and that is the point. A subscription dashboard where nobody bought older lists or upgraded. Custom lists by location, industry and funding stage, which produced a single sale in months. Retention friction with exit questions, bundles and discounts, which did nothing. An affiliate program that grew to over 100 partners, of whom only 4 ever brought a customer and only 1 brought more than three, while the manual commission payments and constant emails made it a pain he eventually killed. Free lists posted to Reddit and Twitter that drew hundreds of people and almost no buyers, a “reverse filter” that attracted beginner freelancers full of questions and empty of money. A podcast interviewing agency founders that was easy to book but felt like being a radio host, so he stopped. He even challenges his proudest decision, niching down to agencies, and tries going broad again on the theory that he might have been fooled by randomness. Conversions drop to the floor, and he is happy, because a win there would have sent him chasing the wrong thing. The shotgun works not by hitting but by cheaply killing bad options and keeping him unattached enough to notice when the real signal finally appears.
Follow the money, not the ideology
The real lever does not come from any experiment. It arrives as an email from Vic, a reader who bootstrapped a software company past $1M/year, and a single disarming question during their chat: “So why do your customers unsubscribe?” Alex’s own cancellation form already had the answer in plain sight. Almost everyone said the same thing, that they did not have the time to set everything up and send the emails, or did not know how. Vic’s follow-up, “Then why don’t you send the emails for them?”, leaves Alex speechless, especially once Vic mentions he pays another company $2k/month for exactly that.
Alex’s instinct is to refuse, because he only wants scalable work that does not trade time for money. But he plays with the idea anyway. He emails customers offering to either refer them to an agency or send the emails himself, and eight people reply where one would have been lucky. One insists on working with him directly, citing years of trust, a welcome gift, replies to every email. He names a deliberately crazy price of $2k/month to see what happens, and they accept instantly. Within a week he closes two more at $1,500/month. When he calls everyone he trusts for advice, they all say the same thing he hates to hear: “Alex, just follow the fucking money.” The whole arc is a rebuke to ideology. He spent years believing product beat service and scalable beat manual, and the market rewarded the model he thought was beneath him.
Rethinking what “scaling” even means
Signing service clients forces Alex to dismantle a stack of beliefs he had treated as law. The comparison that breaks them is stark: four years to crawl from zero to $5k/month with SaaS products, one week to reach $5k/month with a service.
- He thought scaling meant laying foundations for a future explosion, systems that grow without you. He doubled the business with a few manual emails and calls.
- He thought scaling meant building for infinite customers. He now sees scaling as simply taking revenue to the next level, one step, and that he never wanted infinity anyway since $1M/year was always the endgame.
- He thought he had to pick a lane, product or service, scalable or manual. He now suspects the messy hybrid is the answer.
- He thought trading time for money was selling his soul. He notices he already works all day on a supposedly passive business, so the honest question is how much worse it could really get.
The reframe is that “scalable” had been a comforting abstraction shielding him from the unglamorous, immediate work that actually moved revenue.
Impostor syndrome as a compass
The decision is not clean, and Alex does not pretend it is. He procrastinates for days on a contract that reads like a mini employment agreement, and he spends weeks pacing the seafront asking what happens if his life becomes a disaster, whether he will have to hire people, whether he can be anyone’s boss when he hated every boss he ever had. Two tools get him through. First, he reframes impostor syndrome as a compass rather than a warning, evidence that he is pushing the edge of what he can do; before the sales call he was shadowboxing and rehearsing, and afterward felt pure relief and victory. Second, he runs a worst-case analysis: if he succeeds he never worries about money again, and if he fails he refunds everyone, feels embarrassed, and goes back to the newsletter he loves. There is a clear way out of the labyrinth, and he is running out of places to hide.
He anchors the leap in a line he wrote years earlier when he was lost back home in Greece: “When in doubt, do the exact opposite of what you’re doing.” Turning his perfect lifestyle business into a possible monster feels like moving in the wrong direction, which under his own rule is precisely the signal to move. A childhood memory sharpens it further: a friend who had lost his father asked the 18-year-old Alex, mid-complaint, whether his relationship with his own father might already be perfect. Sometimes we moan for things to be different when they are perfect already, and the same could be true of the lifestyle business he keeps trying to escape.
Lessons worth keeping
Activity that feels responsible is the perfect hiding place for perfectionism; measure a channel by customers, not by impressions or effort. Run growth experiments like a shotgun, fast and cheap and unattached, so you can kill the losers without grief and stay alert to the real signal. The signal often comes from outside your strategy, from a customer conversation or a stranger’s reply, not from the plan you are in love with. When advisers you trust all say “follow the money,” the resistance you feel is usually your ego defending an ideology, not a real objection. Interrogate the words you treat as law; “scaling” and “scalable” may just be abstractions keeping you from the unglamorous work that pays. Treat impostor syndrome as a compass pointing at growth, and defuse a scary decision by naming the actual worst case, which is usually survivable.
Sources
- Read the full book: alexwest.co/book-six
- Full text: startups-06-follow-the-money
- Part of the Solo Founder series.