Interview with Alicia Underwood, Founder | Chief Social and Influencer Marketing Strategist, TwentyThree, LLC
You were an early pioneer in influencer marketing. What gave you the confidence to step into a space that lacked a clear blueprint?
Honestly, I'm not sure it was confidence as much as it was instinct. The space didn't have a blueprint, but that was exactly the point. I wasn't trying to follow something. I was responding to what I could see forming in real time.
I've always had a strong read on human behavior and digital culture, and an affinity for writing. In hindsight, it makes sense. I majored in Journalism with minors in Business and Psychology. I could see how people were connecting, who had real influence, and how brands were completely missing it. That gap felt more obvious to me than the risk did.
When something feels that clear, you stop asking, "Am I ready?" and start asking, "Why isn't everyone else seeing this yet?"
After years of agency success, what made you decide to stop addressing industry problems and instead build a solution through The Social BoxTM?
Because I got tired of purchasing the same tools and running into the same problems over and over again. Most of these tools were born from a tech perspective, not a lived one.
In the agency world, you're constantly rebuilding systems from scratch for every client. New spreadsheets, new workflows, new ways of tracking content, approvals, usage rights. It's inefficient. And more importantly, it keeps the industry fragmented.
At some point, I realized I wasn't just running campaigns. I was building the same infrastructure repeatedly, just in different forms.
The Social Box™ came directly from that frustration. Last December, I was trying to review influencer content and package it up for a client, and I thought: why does this still not exist? It's the system I wish I'd had after 15 years of doing this manually. Instead of patching the problem client by client, I wanted to solve it at the root.
Many women build deep expertise but hesitate to turn it into a product or platform. What helped you take that leap, and what would you say to others considering it?
I think a lot of women underestimate how valuable their lived expertise actually is. It took me nearly a decade to realize I had the ability to not just visualize a solution, but to actually build one.
We normalize what we're good at because it comes naturally to us. And in doing that, we underestimate our potential to solve things at scale.
For me, the shift happened when I stopped looking at my work as execution and started seeing it as intellectual property. The way I think about campaigns, structure workflows, manage creators. That's not just "how I work." That's a system. And once I saw it that way, it became obvious it could live beyond me.
To anyone considering it: if you've solved the same problem 50 times, you're not just experienced. You're sitting on a product. The question isn't "Am I ready?" It's "Am I willing to think bigger than services?"
What has been the most challenging part of transitioning from agency founder to SaaS builder, and how has that experience reshaped your view of yourself as a leader?
The biggest shift is going from being in control of outcomes to building something that has to work without you.
In an agency, you can step in, fix things, adjust in real time. In SaaS, you have to think in systems, not saves. You're designing something that other people will use without your context, your instincts, or your presence. That's been both humbling and clarifying.
It forced me to do real work on myself too. Therapy, a career coach, asking hard questions about what was actually holding me back. And it made me a more intentional leader. It’s about being less reactive and more strategic, so I can build something that holds up without me in the room.
You have to sell your vision to your developer, your marketer, your peers, and ultimately your customers. That muscle gets stronger every time.
There is a growing conversation about whether women are encouraged to “play safe” in business rather than build boldly. Have you experienced this, and what needs to change?
Yes. But it's more subtle than people often realize.
It's not always someone telling you to play small. It's the quiet expectations around what's "reasonable." Stay profitable. Stay stable. Don't take unnecessary risks. Be responsible. Those are all valid on their own. But together, they can quietly keep you operating beneath your ceiling.
And if you look back through history, women were told to keep their voices small. To not push. To conform because it was easier. Part of that legacy is that women were conditioned into survival mode for a long time. When you're constantly surviving, you don't have the bandwidth to build boldly.
Building something like The Social Box™ requires a completely different mindset. You have to be willing to forgo immediate returns, to invest ahead of validation, to take bets that don't make sense to everyone around you.
What needs to change is how we define ambition. Women aren't lacking boldness. We're often just navigating environments that reward caution.
On a more personal note, was there a moment in your journey where you doubted yourself, and what helped you push through it?
Absolutely. Honestly, all the time. Especially in this phase.
Building a product is a completely different game. There are moments where you question whether you're overreaching, whether the market will get it, whether you built too early or too late. And feedback can sometimes feel personal, even when it isn't.
What grounds me is going back to the problem. Not the noise or the opinions. Just the actual pain point. What am I trying to solve?
I've lived this problem for over a decade. I know how broken the workflows are. I know how much time and money gets wasted.
When you anchor yourself in something that real, the doubt doesn't disappear. But it stops being the thing driving your decisions. And the thing I always come back to, for myself and my team: is this fun? Because if it's not, what's the point?
