Anna Fenstermacher: From $100 Brand Deals to Building Real Influence

Photo Courtesy to @verameyphoto

Anna’s journey into the influencer space didn’t start with a strategy or a vision board. It started in 2018, right after she graduated college, when a brand messaged her out of the blue asking if she could create 15 product photos a month - for $100. At the time, she didn’t even know what UGC meant. But the offer felt like magic. She was getting paid for doing something she loved.

Looking back now, she laughs at how little she was paid, but she doesn’t regret it. That moment marked the beginning of a career she’s since built with intention, honesty, and a lot of backend work most people never see.

There’s a romanticised version of what it means to be an influencer, but the truth is, most of the work isn’t visible. There’s planning, analytics, outreach, brand negotiations - and a constant commitment to integrity. For Anna, every partnership starts with a single question: “Would I spend my own money on this?” If the answer isn’t an immediate yes, it’s a no. No matter the rate, no matter the brand name.

Authenticity isn’t something she layers on - it’s the foundation.

She knows the value of her time and her platform, and if a deal doesn’t align with her values, her audience, or her schedule, she walks away. That clarity didn’t happen overnight. It’s been shaped by years of showing up online and learning how to balance transparency with growth.

When it comes to building a following, Anna’s approach is deeply human. Her most engaging content isn’t over-edited or heavily curated - it’s the simple, stripped-down sit-down videos where she shares what’s actually going on in her life. Those are the moments that build trust. Those are the videos that turn viewers into community.

She’s also fiercely supportive of other creators. She engages with their content, shares their wins, and treats them the way she hopes to be treated. That reciprocity has shaped her growth just as much as her content has.

The Strategy Behind the Storytelling

While most people focus on going viral, Anna focuses on staying consistent. She checks her analytics every week, pays attention to what resonates, and then iterates - creating new versions of what works, over and over, until it builds into something real. She doesn’t chase algorithms; she builds patterns. And that’s made all the difference.

What she didn’t expect, however, was the financial unpredictability that comes with being a creator. Waiting 30, 60, even 90 days to get paid for a campaign can be stressful - especially when bills don’t wait. That’s why she still keeps a full-time job. It’s not always easy to juggle, but it gives her a stable foundation and the freedom to be selective with her partnerships.

Multiple income streams, she explains, are essential. Relying only on brand deals is risky. She suggests platforms like Amazon Influencer or Like to Know It as ways to even out the income flow—especially when one side slows down.

If you ask Anna what she’d tell her younger self - or anyone just getting started, it’s this:

"Be patient, be consistent, and don’t be afraid to be seen trying. Growth won’t always be linear. You might not see results after 30 days. Post for 30 more. Some months you’ll explode, some you’ll plateau. That’s part of the game."

She also wants new creators to remember that being themselves is more powerful than any aesthetic. Don’t copy someone else’s formula just because it’s working for them. What people are really looking for is a connection-and that only happens when you’re honest about who you are and what you love.

It’s scary, she admits, to be vulnerable online. Especially when your personal life overlaps with your career. But that vulnerability is what makes the job meaningful. She didn’t have a blueprint when she started. She still doesn’t. But she shows up anyway, building something real one post, one partnership, one connection at a time.

Being a creator isn’t just about content. It’s about the conversations, the consistency, the character. And Anna has built hers with all three. No shortcuts. No gimmicks. Just a quiet confidence that being yourself is enough, and that staying true to that can take you further than anything else.

🎥 Watch the full GRWM interview now on Roe’s YouTube channel.