Aspire wanted a blog for founders, and the editor’s row was still empty
In November 2021 I’d just moved back to Belgium and registered my own business, with no retainer client to my name. Then the Aspire job came through Rahul Chawra. I’d already written for his own business, and he was now managing brand and content at Aspire, a Singapore startup building business finance for other startups. He needed an editor for a blog Aspire hadn’t launched yet: the Founder Academy.
Aspire’s project tracker from October 2021 shows how far the Founder Academy had got. Marcella and Rahul were working through a first ideation draft, Hannah and a “2nd writer” had rows for research and writing, and two more rows covered overseeing the writers and preparing distribution. The name next to those two just said “Editor”. There were no posts yet, no shared writing standard, and the topic plan was still an early draft.
So the job was narrower than owning Aspire’s marketing, and deeper. Rahul ran brand and content. I filled that editor row on a retainer, responsible for how the blog was structured, how it was written, and every piece before it went live. It was also my first retainer, the one that turned freelancing into a full-time business.
From Rahul’s first map to a plan of at least sixty researched pieces
The first plan for the Founder Academy was Rahul’s, worked out with Marcella before I arrived. It followed a founder through the life of a company in five stages, from getting started the right way to preparing for growth funding, with ideas for pillar and cluster pages under each. My job was to turn that map into something writers could work from, so I built on it with Rahul: which topics made the cut, how to divide them, and how to position each one. By the time the plan was final, it held at least sixty pieces, each with its keyword research done. That research went straight into the brief every writer received.
The plan ran on the pillar-and-cluster model, a content structure HubSpot popularised years before. A pillar page goes wide. In the writing guide I described it as “essentially a list of all subtopics under a chosen topic”, with a little on each. The cluster pages underneath go deep on one subtopic each, and the guide set a simple bar for them: a cluster page “should leave no more questions about the subtopic.” For founders, that split worked well. The pillar could walk someone through a whole subject, while the clusters took one term or one decision at a time for the reader who needed exactly that.
The model also gave the blog a clean internal linking structure. Every pillar links down to its clusters, every cluster links back up to its pillar, and clusters link to each other where their topics touch. A stream of standalone articles would have been quicker to start, but each post would have stood on its own. With the pillars in place, every new piece had a slot waiting for it and a set of pages to link to. I tracked the whole structure, and every internal link in it, in spreadsheets, so at any point I could see what had shipped, what linked where, and what was still missing.
"I brought him as the editor to project manage content and process for a blog meant for startups. Once again, he created a style guide, oversaw 4 writers, defined posting structure and delivered a proud output."
One writing guide to hold every draft against
Four writers means four ways of explaining the same thing. The Founder Academy’s writers were a mix of Aspire’s own people, including Hannah and Marissa, and freelancers, among them Joshua Poh, the most senior writer of the group. For one important pillar piece, I brought in a fifth, John Paul Hernandez. With that many hands on one blog, I wrote a style and writing guide the whole team worked from, and it started with the reader: founders in South-East Asia’s start-up scene who “won’t be familiar with financial jargon.”
The guide was specific on purpose. Paragraphs ran no longer than four lines of eight words, headlines stayed under 15 words, and writers marked exactly where a visual should go so the designers could get to work. Definitions came from two shared glossaries, one for terms and one for metrics, and anything missing went through Rahul or me, so every term meant the same thing in every article. (It also banned the em dash. Some rules stick.)
I’ll be honest about how far the guide went: not every writer stuck to it. But it gave me a fixed standard. Before any piece went live, I compared it against the guide and the glossaries, so the blog read as one publication rather than four. This was before AI, so that check was manual, with Grammarly for plagiarism and not much else.
The Founder Academy had its system by February, and SEO needed longer
When my Aspire retainer ended in early 2022, after about three months, the Founder Academy had gone from an early topic draft to a working blog. Its plan of at least sixty pieces was mapped out as pillars and clusters, with the keyword research done and every internal link tracked in spreadsheets. The writers had a style guide and two glossaries to work from, and the first pillar and cluster pieces were live, all edited to one standard.
What it didn’t have yet was search traffic to show for it. A pillar-and-cluster blog pays off as the clusters fill in and the pages build authority, and three months is early to see that in SEO. The retainer ended before the model had the time to prove itself. Rahul brought me into more of his own projects after Aspire, and we’ve stayed in touch since.
What I’d do differently: get the first posts live in the first few weeks
The Founder Academy took a month to a month and a half to publish its first posts, and by the end of December only a couple were live. Looking back, I’d push much harder on that first stretch. I’d get the first pillar and a few of its clusters out within the first weeks, even before the rest of the plan was polished, so the blog would have had some early signals by the end of December. In SEO the clock starts when a page goes live, and on a three-month engagement the first six weeks are half of it.