Shannon Trimble Is Growing Her Freelance Business. One Coffee Chat at a Time

Shannon Trimble Is Growing Her Freelance Business. One Coffee Chat at a Time

The content marketing industry is weird right now, and I’m sure I’m not the only one experiencing this. If you’ve been freelancing for a while, you’ve probably noticed the shift too: fewer responses to pitches, shrinking budgets, and more clients asking, “Can’t ChatGPT do this?”

That’s why this year, I shifted my focus. Instead of constantly applying to job calls, I’ve been leaning into relationship-building and personal branding. It’s a long-term strategy, so I’m building patiently.

Recently, I had a coffee chat with Shannon Trimble, a freelance content marketer and solopreneur who works with FinTech and RegTech brands. I came across one of her posts where she mentioned being open to virtual coffee chats, so I indicated interest.

We had a thoughtful, insightful conversation that gave me a fresh perspective on networking, and I thought to share it with you, too.

In this blog post, I’m sharing what I learned from our chat and why you should consider embracing coffee chats as a way to build meaningful connections, strengthen your brand, and, of course, get clients.

But first, if you’re wondering what a coffee chat even is, let’s clear that up. 

What is a coffee chat?

A coffee chat is a casual, intentional conversation (usually virtual) between two people in the same or adjacent fields. It’s not a pitch. It’s not an interview. It’s simply a way to connect, share experiences, ask questions, and learn from each other. 

Can anyone have coffee chats?

Absolutely. You don’t need to be “established” to reach out for one. Whether you’re new to freelancing or 5 years in, coffee chats are a great way to grow your network and learn from other people’s journeys.

You’d be surprised how many seasoned freelancers are open to chatting, especially when you approach them with authenticity and respect. If you’re worried about what you’ll say, don’t overthink it. It’s okay to just show up, ask questions, and listen.

How do you start having coffee chats?

Start by identifying people you admire (writers, marketers, freelancers, agency owners) and engage with their content.

If they are open to connecting, send a friendly message asking if they’d be open to a quick coffee chat. I found Shannon through one of her LinkedIn posts, and we had an amazing conversation. That’s all it takes.

My Conversation with Shannon Trimble 

Can you tell me a bit about how you got into the fintech marketing space?

It was totally random. I graduated in 2018 with a degree in sports science, then moved to Australia and worked in a school. I loved it, but had no money, so I became a virtual assistant, mostly doing admin work. 

One of my first clients was a financial advisor in the U.S. who asked me to write blog posts. I gave it a try (probably wasn’t great), but I liked it. I started taking courses, improving my skills, and gradually moved into content marketing, mostly in finance.

That evolved into fintech, and now regtech.

Interesting. So, why do you do coffee chats? What inspired you to start?

Two reasons. First, to pay it forward. I’ve had people help me out throughout my career, and this is one way I can support others. Second, I’m a big believer that you can learn something from everyone. Even if the chat isn’t work-related, I always walk away with a new perspective.

That’s powerful. Do you prepare before your chats or go in casually?

Not really. It’s uncomfortable for me not to plan, but I think growth comes from discomfort. I use these chats to practice being present, listening, and just seeing where things go.

Have any of these chats led to work or referrals?

Sometimes, yes, but that’s not the goal. I try to avoid treating it as transactional. I don’t come in with a set agenda. I prefer to let the conversation flow organically.

Would you recommend coffee chats to other freelance writers?

Yes, especially if you’re already doing other forms of marketing. It’s a slow-burn strategy, but it helps keep you top of mind. When someone sees an opportunity later on, they’ll think, “Oh, I just spoke to Shannon!” But it shouldn’t replace higher-priority tasks like lead generation.

>>> READ MORE: 5 Content Writers Share Their Secret Strategies For Landing High-Ticket Clients

TL;DR: 3 Takeaways From Our Coffee Chat

1. Focus on Building Relationships, Not Pitching

Approach coffee chats with a mindset of curiosity, not conversion. The goal isn’t to pitch yourself, it’s to learn, share, and build relationships that might grow into something more.

2. Let Conversations Flow

You don’t need a perfect agenda. Some of the best insights come from unstructured, honest conversations. Get comfortable with the unknown.

3. Use Coffee Chats as a Long-Term Strategy

Coffee chats won’t instantly get you clients, but they’re a powerful way to grow your network, stay visible, and open unexpected doors.

If you’re a freelance writer navigating slow seasons, I hope this post gives you something new to try. Start with one coffee chat. Reach out to someone whose work you admire. You never know where it might lead.

I’m always open to making new online friends. Feel free to connect with me on LinkedIn.