Laid-off tech VP to entrepreneur: 7 lessons I learned

More than 20 years and seven businesses later, I’ve learned a lot, often the hard way.

Here are seven lessons I wish I understood when I started:

1. Your paycheck isn't the same as security.

A good job can provide stability. But someone else still controls the paycheck.

Learn how to create opportunities for yourself. I’m not suggesting this is an easier path. On the contrary, it’s certainly harder. But you’re building toward greater financial independence and something you can be genuinely proud of.

Nothing great in life comes easy.

2. Tighten the belt.

Your business plan and sales projections might show income in month two. With your sales hat on, absolutely plan to hit those targets aggressively.

But with your finance hat on, control and reduce your expenses. Build financial runway. Understand how long you can survive without meaningful revenue.

You’ll have to take risks. Learn how to take calculated risks, not reckless ones.

3. Confidence comes from doing the reps.

After delaying this step for weeks because of my fear of selling, I finally made five in-person pitches on my first day selling website services.

Five rejections.

My co-founder and I were devastated. We almost quit. We figured maybe this wasn’t meant for us. But we had rent to pay, so we kept going.

Eventually, I landed my first $1,400 project. Several years later, we were landing $140,000 projects.

Confidence didn’t come before the action. It followed it.

4. Do the unscalable things first.

A 9-to-5 mindset won’t cut it, and standard operating procedures won’t cut it either. You have to do a lot of new things, and you have to do a lot of them. Things you’re comfortable doing and saying, and things you’re not.

Talk to prospects. Work your network. Deliver the work yourself. Get testimonials.

5. Don't outsource sales too early.

I made a bad hiring decision that cost me tens of thousands of dollars.

Before you understand what’s involved in selling your service, you’re not in a position to outsource sales. You can do that later. For now:

Pitch. Hear the objections. Follow up. Negotiate. Close.

Learn to sell before hiring someone else to sell for you.

6. Sell outcomes, not your expertise.

Your methodology, tools, and technical knowledge matter. So do industry awards, certifications, and published work.

But your clients ultimately want to know:

“What problem will you solve for me?”

Focus the conversation on solving their problem.

7. Build “builder confidence.”

Professionals often develop execution confidence:

“Give me the assignment, and I’ll deliver.”

Entrepreneurs need something different:

“Give me nothing, and I’ll create an opportunity.”

You have no HR department, no finance department, no sales department, and no marketing department. You have to learn these functions, and they’re learnable.

Once you develop that builder mindset, every new function or task becomes something you know you can figure out.

Hit reply and let me know what other lessons you’ve learned on your journey. I’d love to hear from you.