Founder Wisdom: Hard-Earned Lessons From the Trenches

Welcome back to Founder Mode!

Founding a company teaches you more in one year than most jobs teach you in ten. Lessons often come from losses, not just wins. They arise from messy moments, tough talks, and mistakes you’d rather not repeat.

This week, I’m sharing a few lessons I’ve learned recently. They might not be in textbooks, but they offer real-world wisdom. This wisdom saves time, money, and sanity.

The "Free Work" Trap

One of the biggest mistakes founders make is giving away too much free work.

We fell into this recently with a client who kept asking us to “just look into one more thing.” Before we knew it, we had done weeks of work without a clear scope or payment.

At some point, I had to draw the line:

That conversation was uncomfortable, but necessary. We delivered value. Now it’s their turn to pay before we continue. Free work isn’t validation, it’s a slow bleed.

Founder-Led Validation

When you’re testing a new low-cost offering, say $200 a month, you can’t delegate validation. The founder has to be the one making the calls.

I’ve been personally dialing leads. Not just to sell, but to understand:

• What pain points matter most?
• What messaging actually lands?
• Where do integrations break down?

These early calls aren’t scalable, but they’re priceless. They give me the raw input I need to build the playbook for a future sales team.

The Technical "Do-It-Yourselfer"

You might come across prospects who are working on their own take of your solution. These people can be tricky. They often care a lot about prices. They also believe they can do it cheaper on their own.

When I see this, I treat it as a learning opportunity. I pitch our value, but I also stay realistic. Sometimes, they just want free advice to fix their broken setup.

Either way, it’s a signal. I gain insights into their problems and where they feel stuck.

Create Momentum, Don’t Wait

Integration roadblocks happen. A client’s tech team may delay decisions, hold up approvals, or get stuck on other tasks.

But that doesn’t mean we sit still. We started making voice samples and scripts as we waited for one dependency. That way, when the integration clears, we can move fast.

The lesson: always find a parallel path. Don’t let one blocker freeze the whole project.

The Bigger Picture

All these lessons add up to one truth: momentum is everything.

If you give away work for free, you lose momentum. If you avoid tough conversations, you lose momentum. If you wait for perfection, you lose momentum.

Momentum isn’t about speed for its own sake; it’s about progress. It’s about refusing to stall.

5 Key Takeaways

1. Don’t fall into the free work trap. Value delivered must be value paid for.
2. Do founder-led validation. Early calls are unscalable but essential.
3. Handle DIY prospects carefully. Learn from them, but guard against free consulting.
4. Always create momentum. Find parallel paths instead of waiting.
5. Momentum compounds. Small forward steps are better than sitting still.

Final Thoughts

Being a founder is about making judgment calls in messy situations. The wins are great, but it’s the traps you avoid that often save the company.

This week showed me that being clear, direct, and moving forward is better than striving for perfection.

So here’s my challenge to you: look at your week ahead. Where are you waiting when you could be moving? Where are you giving away too much when you should be charging?

That’s where your founder wisdom needs to kick in.

See you next week,

-kevin

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