If you ask me what the hardest part of building Plumm has been, I won’t give you the obvious answers.
Everyone wants to talk about the product breakthroughs and the fundraising rounds. Nobody really talks about the relentless emotional pressure paired with the decisions you have to make with half the information you’d like.
The part of founding a company that nobody tells you is that the uncertainty never fully lifts – you just learn to function inside it.
Building Plumm has taught me that the hardest part of this job has nothing to do with product and nothing to do with capital. The toughest call I’ve had to make was pivoting Plumm from a mental health platform into a full HR system with embedded mental health.
We had real traction and people liked what we’d built. And I made the decision to tear it apart anyway because I could see that where we were sitting had a ceiling and that ceiling wasn’t high enough.
It meant rebuilding the product from the ground up and repositioning everything we’d told the market about who we were. There was no guarantee it would work. I just knew that staying still was the wrong answer, even if moving felt terrifying.
That’s a decision I couldn’t have made by committee, and this brings me to something I feel strongly about: who you surround yourself with will make or break you, probably more than any product decision ever will.
I’ve learned to keep a very small circle of people I genuinely trust and I’ve learned to be ruthless about the difference between advice that challenges me and advice that just makes me feel comfortable.
The most draining counsel I’ve received sounds reasonable on the surface: wait for the right moment, don’t take unnecessary risks. That kind of thinking doesn’t build anything meaningful.
The advice that has actually moved me forward is simpler and less comfortable: back your instincts, take calculated risks. Nobody has a clearer view of your business than you do. Don’t let cautious voices talk you out of what you can see with your own eyes.
The same principle applies to the people I hire. I’ve made the mistake of bringing in people who were impressive on paper and fell apart the moment things got ambiguous and, in a startup, things are almost always ambiguous. I don’t hire for experience alone anymore, I hire for the ability to operate without a map.
The founders and operators who struggle aren’t usually the ones who lack talent, they’re the ones who need structure and clarity before they can move and startups are environments where both of those things are in permanent short supply.
On product and fundraising, my views are straightforward. Build something that solves a real and significant problem, something significant enough that people will pay for it without being persuaded and then tell everyone they know about it. That’s the product bar worth aiming for.
On fundraising, I’d say this: don’t make it your priority before you’ve built something real. The founders who raise from a position of weakness are almost always the ones who went looking for money before they had the fundamentals in place. Build those first. The stronger your business, the more leverage you carry into any conversation with investors, and the less you sound like you need them.
The question I get asked most often is how to deal with uncertainty and hard decisions and my honest answer is that there’s no elegant solution to either. Practically, I’ve learned to stop staring at the full scale of a problem and just focus on the next step in front of me. Most decisions feel bigger and more permanent than they actually are.
Emotionally, I’ve had to accept that discomfort isn’t a signal that something is going wrong. More often than not, it’s a signal that you’re doing something that actually matters. The goal isn’t to get rid of that feeling, the goal is to keep moving through it.