notessamuele onelia

1,500 Cold Pitches at One-in-Two-Hundred

The Story

How Olivia got her first freelance clients, in her own words: “My first couple of years, I got every single client through cold outreach. I pitched to over 1,500 agencies, business owners, influencers — anyone. My partner and I did the math: for every 200 pitches, I got one project” (Source 1).

The 200:1 conversion is the unhedged number she puts on cold outreach as a freelance-writing acquisition channel — roughly 0.5%.

What she did after the cold-pitch phase: “Then I turned to LinkedIn. At the beginning of 2024, I started being really active there, and over the last couple of years, all of my clients have come from the platform — either through people posting that they were hiring, or people seeing my work and reaching out directly” (Source 1).

Her framing of LinkedIn as a portfolio rather than a network: “I like to call LinkedIn a living portfolio — potential clients can look at your posts and think, ‘Okay, this is what I could expect if I worked with them.’ Every writer should be on there in some capacity!” (Source 1).

The single biggest unlock she names, separate from cold outreach: agency partnerships. “Partner with agencies. If you want to get into freelance writing, but don’t want to deal with the hustle of finding new clients every week, content agencies are the answer. A lot of them bring on contractors to handle overflow work or as a core part of their team” (Source 1).

The stability data point: “Agency clients have been my main source of work since 2022, and it totally changed the game. I rarely have to hustle for new clients anymore. There have been slow periods where I’ve had to rebuild my roster, but typically my agency partnerships last a year or more” (Source 1).

A specific tactical move she shares: “If you want to work with agencies, try applying to their full-time job listings. If an agency is hiring a copywriter, reach out and say, ‘Hey, I see you’re hiring. Would you be interested in an interim solution who can start right away while you look for someone full-time?’ That approach has led me to a few big contracts” (Source 1).

The moment she identifies as when the business worked: “Before I partnered with my first agency, I had a couple of clients. I was working five hours a week here, a $1,000 retainer there. It was great, I was getting by, but I was still working part-time at a co-working space as a community host to supplement my income. When I landed my first agency partnership, it was consistent enough — and I was making enough money — that I could go full-time. That’s when I realized, wow, I can actually do this. That was the big moment for me” (Source 1).

What didn’t work: “Upwork. I was a very early user… I found that the clients typically don’t value freelancers at all on Upwork. There was no relationship. I felt like I was expected to turn things around 24/7, with no boundaries. I decided to completely walk away from those kinds of platforms” (Source 1).

The result she lists publicly: “I’ve worked with founders, executives, and B2B brands on LinkedIn content, case studies, long-form technical guides, ebooks, blogs, email campaigns, and Substack ghostwriting. My work has helped clients reach six-figure audiences and get featured in publications like Entrepreneur and Vogue” (Source 2). The trajectory in three lines: “In 2017, I started freelance writing as a side hustle… When the pandemic hit, I took the leap into freelancing full-time. It wasn’t smooth sailing — I undercharged, overworked, and learned the hard way that self-employment comes with its own set of challenges” (Source 3).

Lesson for Creators

Most freelance-writing advice glosses over the early-career conversion math. Olivia’s number — 1 client for every 200 cold pitches — is what the math actually looks like when you have no audience, no portfolio, and no warm intros. The honest framing matters because it sets the right expectation for anyone starting cold: this is not a hack, it’s a numbers game, and the numbers are unforgiving. The more useful insight is what she did after the cold phase worked: she stopped doing it. Agencies replaced cold pitching with annual partnerships, and LinkedIn replaced cold pitching with inbound. The pattern across her career is moving from low-conversion, high-effort channels (cold email, Upwork) to higher-conversion, lower-effort ones (agency retainers, LinkedIn portfolio inbound) as soon as each became possible. The lesson generalizes: cold outreach is the channel you use when nothing else is available, and the goal is to graduate out of it. The 1,500 pitches weren’t the strategy — they were the bootstrap that funded the search for a better one.

Backlinks

External sources