When experience becomes the enemy
What if what you know holds you back from progress?
Hi, it’s Melissa, and welcome (back) to “your founder next door”, a weekly publication with stories and tidbits of my human journey bootstrapping eWebinar to $5m ARR. No BS, just straight-up truth bombs on what it’s like to build a company without an abundance of resources or friends in high places.
If you’ve been following along these past few weeks, you know I’ve been deep in the weeds on reframing and identity, and how what we believe about ourselves and our businesses shapes our reality. This week, I want to take that thread one step further.
I’ve always believed that there’s a point where experience hinders you. Admittedly, I’ve been there for a while.
Early in my career, I would do anything. Cold call anyone. Walk up to an important stranger at a conference like it was natural. I once cold emailed the CEO of Zillow, invited him to a dinner at my house, and used his name to fill the rest of the seats at the table. That dinner changed the trajectory of my career and eventually led to the sale of my last startup.
I did that because I was naive, desperate, and had nothing to lose. I didn’t know the pain and suffering I was up against, so everything was worth trying. I was a blank slate.
The Melissa of today would never do that. Not because she doesn’t want to, but because she knows too much.
I know the pain of strategies that don’t pan out. The embarrassment of putting yourself out there and getting silence in return while everyone watches. I’ve built enough comfort around myself that I no longer need to take those swings. Not having pain is its own kind of self-preservation, and it’s easy to hide behind that cozy security blanket and justify it with experience.
I’ve already tried that. I know how this goes. It’s not worth the effort.
That’s what experience sounds like when it turns into a gate. The gate between where you are and all the opportunities you’ll never come across.
Naivety was one of my superpowers that withered away over time. I can’t even pinpoint when, but I can vividly remember all the things I used to do that I’d never do now. The Zillow dinner is a perfect example. That kind of opportunity doesn’t come from playing it safe. It comes from being open enough to try the thing that seems unreasonable.
How many opportunities like that are we leaving on the table because experience told us not to bother?
Everything is moving at an exponential pace now. SEO turned into AEO almost overnight. Software and workflows that used to take months to build are being shipped in days. Everything is getting more niche. Behavior is changing. The people you were trying to reach last year aren’t even behaving the same way today.
When what didn’t work last week could work this week, holding onto old conclusions is one of the riskiest things we can do.
A couple of years ago, we tried expanding into new content topics at eWebinar. We put some pieces out there, they didn’t perform, and we stopped. That didn’t work. So we moved on and didn’t look back.
Now, we’re venturing back into that same territory because we realized we may have stopped short. We’re a different company today. Different features, different messaging, different customer stories. The market is different. The timing is different. The only thing that stayed the same was the assumption that it wouldn’t work because it didn’t work then.
If we let that old evidence be the final word, we’d never discover the much larger audience sitting out there.
The most dangerous place to be as a founder is “good enough.” We had revenue. Happy customers. Sign-ups every day. There wasn’t a clear reason to say things were bad. So we kept doing what we were doing and stalled, not knowing the strategy that got us to profitability was the same one keeping us small.
Complacency doesn’t announce itself. It just happens... quietly.
The more comfortable things feel, the more holes you should be poking in your own hypotheses. Not less. If you’re right about one thing and it unlocks 20% of your business, staying there means you’re leaving 80% on the table.
We only have so much time to put into our companies, so the time we invest should have the highest possible return. You don't get there by only doing more of what's already working. You get there by continuing to uncover what you haven't tried yet, so you can hone in on the things that deliver the most value and keep finding better opportunities.
We need to be wrong more often so we can find the best path forward.
Being right feels good. It feeds the ego. It confirms we’re on the right track. Being wrong is uncomfortable and humbling. It means the thing you were sure about wasn’t the whole picture. It means continuing to chip at something you thought was done.
Being right is a spectrum, not black and white. You can be right and still uncover more that’s out there. Being wrong is how you find it.
The antidote is curiosity. Not just curiosity about new things, new strategies, new tools. That’s obvious. I’m talking about curiosity directed at the things you think you already know. The conclusions you drew years ago and never revisited. The strategies you tried once and wrote off. The assumptions so deeply engrained in how you operate that you forgot they were assumptions.
What if I’m wrong? What if I’m only seeing part of the picture? What if the thing that didn’t work before would work now? What if the limit I accepted isn’t actually a limit?
Curiosity is where growth lies.
Here’s my challenge to you… look at something in your business you decided was “done.” Something you tried, concluded on, then shelved. Ask yourself why you stopped. What’s changed since then? What you might be missing?
Curiosity may have killed the cat. But it could be the thing that gives your company life.
Till next time,
— Melissa, your founder next door ✌️
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Crazy story about the dinner!
And thank you for one more reminder about benefits of being naive!
There is an expression about how bumblebee flies against the rule of physics - they simply do not study physics so they fly
i've watched the same thing happen in myself, and in almost every solopreneur i talk to. the knowing becomes the gatekeeping. a strategy didn't work two years ago and it becomes a permanent fact rather than a data point from a different moment. what struck me most here is the framing around complacency: it doesn't announce itself, it just happens quietly. i had a period last year where things were stable and moving, and i stopped poking at anything because the numbers felt fine. i only noticed the drift months later. the antidote you name, curiosity directed at things you think you already know, is the part i want to sit with. what's the most useful thing you've tried when you notice you've stopped questioning an old assumption?