Debrief: my 30 days plans to crack product marketing freelancing

I have to confess: I’m not really the kind of person who designs great plans and religiously executes them. Usually, I feel more comfortable setting macro-targets and doing quick, spontaneous iterations to reach them. That’s also why I thrive in early-stage startups’ fast-changing environments.

Writing “My 30-day plan to crack product marketing freelancing” was a bit of wishful thinking. By doing so, I was hoping to enhance my chances of actually defining a plan and following it.

Turns out, I surprisingly stuck to that plan.

Not on purpose, but because it just made sense.

I’ve done most things I said I was going to do in my previous build-in-public post:

• I’ve talked to 7 early-stage founders.

• I’ve networked with 12 other product and marketing freelancers.

• Instead of job posting, I’ve directly applied to a few job offers and learned a lot more in the process.

Time to share my learnings. It’s month 2 of my 6-month journey from 0€ to 10,000€ / month.

In my previous post, I explained my ambition of cracking down a niche offer with a replicable methodology and a go-to-market strategy that would allow me to get 10k€ / month revenue before February 2025.

My priority during the last 30 days was to find out what urgent problems my ideal customers (early-stage startup founders and leaders) are facing.

I started trying different initiatives:

• Partnering up with an incubator and providing 1:1 mentorship. (3 leads generated)

• Reaching out to founders manually on LinkedIn. (2 leads generated)

• Answering job posts. (2 leads generated)

I talked to 7 founders over the last few weeks – all of them had different problems.

From pre-seed SaaS founders focusing on product-market fit to post-seed fintech companies looking to create the Product Marketing function within the organisation, the challenges varied widely.

Which makes sense, as Product Marketing and go-to-market are extremely broad discipline.

Needless to say that I’m not even close to find that niche offer, BUT I’m taking a step toward that goal.

I’m going to need to talk to WAY more founders in the following weeks.

Ideally, I would do at least one 30-minute consultation per day (23 per month).

I believe that best way to achieve these goals is to position myself as a generalist for early-stage companies, meaning a founding PMM or first PMM.

I know what you might be thinking:

So, your strategy to crack down a niche offer is actually to position yourself as a generalist?

Yes.

Y Combinator has this saying, “do things that don’t scale,” and that’s exactly what I’m doing. I’m always looking for shortcuts – but sometimes it’s about doing things in the right order.

Scaling is great, as long as your scaling the right thing.

At this stage, my priority is to iterate through various product marketing tasks (pricing, positioning, GTM strategy), create case studies, and refine my approach until I find the combo value proposition + standardized method + and GTM strategy.

What comes next? I’ve started a new strategy to nurture my relationships with early-stage founders. I’ll share more about this in my next post.

Over the past few weeks, I’ve interviewed over 30 freelancers, with 12 of these conversations taking place in the last month alone.

When asked, “How do you find clients?”, the most frequent response was unexpected: “luck.”

However, upon deeper analysis, what freelancers describe as “luck” often means:

• Inquiries through freelancing platforms

• Referrals from past colleagues or clients

• Unexpected opportunities arising from their professional network

This points to a significant insight: many freelancers lack a structured, proactive approach to client acquisition.

I’ve identified three main categories of freelancers:

1. The “network guys”: These freelancers heavily rely on their the professional connections they build over the years to find clients.

2. The “balanced”: They try different strategies, balancing their existing network with occasional posts on LinkedIn and attending events.

3. The “niche specialists”: These freelancers are actively working to develop a “personal monopoly” in specific domains. They are usually the top performers in the freelancing game.

There’s not one recipe to succeed in Freelancing, but there are recipes that have proven to work. Finding out these recipes is going to be my next goal.

What comes next? I’ve decided to laser focus on networking with niche specialists.

Instead of analyzing job offers, I’ve applied directly to them. Product marketing is still an emerging practice in many European countries, and there’s a clear lack of expertise for these roles. The market is booming and getting interviews for permanent positions is quite easy.

Getting interviews is only one part of the job. Then, there’s the skills / company fit-discussion part and then agreeing on the terms of the collaboration. That’s usually where the process ended.

From getting a permanent contract to working with freelancers, there’s a psychological gap that some founders are not willing to bridge. Moreover, the fact that I only work 100% remotely is a deal-breaker for many companies.

I got two interviews for VP and Director Product Marketing roles. Both have fallen short because they were either in-person or not willing to work with freelancers.

Even though I haven’t been successful yet with this approach, I believe there’s room for improvement. There’s a clear potential here.

• First, because it’s a great way to start conversations with clients and learn about their needs.

• Second, because these companies are in-market, they are actively looking for someone.

While negotiating full-remote instead of in-person might be hard, I believe there’s space to convince founders that working with a freelancer could actually be a great idea for their business.

Finding how is going to be my next priority.

What’s next? Keep applying to PMM jobs in early-stage startups and optimize my selling strategy and process. Ask more questions about the “why,” pinpoint precisely the objections, and deal with them.

Two months in, and this freelancing journey has been a rollercoaster of insights and challenges. As I move forward, my focus is clear:

1. Multiply consultations with founders up to 20 per month.

2. Work as a founding / first PMM in early-stage start-ups to get a better chance of identifying niche opportunities for the future.

3. Network with successful niche specialist freelancers to learn about their journey.

4. Improve my job application strategy, addressing freelance objections head-on

5. Iterate until I develop a structured client acquisition process

The path to 10,000€ monthly isn’t easy, but each learning brings me closer. I’m excited to implement these strategies and see where the next month leads.

Stay tuned for my next update on nurturing relationships with early-stage founders. The adventure continues!