10 Hard-Earned Lessons I Wish I'd Learned 20 Years Ago

Here’s some other content from the Scalable network, plus some other cool stuff I liked and thought you might like, too:

If I could hop in a time machine and talk to 25-year-old me (the guy building his first business from a dorm room), I wouldn’t give him motivational quotes or productivity hacks…

…I’d hand him this list.

These are the 10 lessons that would’ve helped me scale twice as fast, with half the stress, and a lot less sleepless nights.

When I started my first company, I made my college roommate CMO and my receptionist COO. (Spoiler: neither went great.)

Titles = entitlement.

If someone’s “in charge” of something, but they’re not yet operating at a true executive level, call them “Head of [X].”

It gives them ownership without inflating expectations or compensation demands.

Promote the role first…then give them the title to match if/when they earn it.

I used to think salaries were for employees…no “real” entrepreneurs like me. So I rode the feast-or-famine rollercoaster: take a ton out after a good month, starve during a bad one.

A mentor finally told me, “Pay yourself a salary, you idiot.”

He was right.

Paying yourself a consistent salary is proof of a well-run business. It keeps your emotions stable and your decision-making objective.

You’re not being greedy…you’re building sustainability.

Google what CEO’s of company’s your size in your industry make, and start paying yourself that.

Cash = confidence.

So keep at least three (3) months of true operating expenses sitting safely in cash or a money market account.

Then open a separate tax account and fund it every month before you pay yourself or anyone else.

I learned this lesson when I got a Sunday-night call from my accountant telling me I owed a quarter-million dollars to the IRS…and didn’t have it.

Never again.

The only vendor who can take your freedom is the government, and the only thing worse than a big tax bill is not having the cash to pay it.

When that tax bill hit, I made it back in a week because I owned my list, which meant I could reach my customers directly.

Here’s what I did: I researched all the best promotions we ran across all my businesses over the previous 12 months, and I ran all of them simultaneously in a week.

The result? $336K in sales…enough to cover my tax bill plus all the taxes I would owe on sales I just made.

A friend of mine wasn’t so lucky…

He built a multimillion-dollar business selling through Walmart. Things were going great until Walmart replaced his product with one of their own.

If someone else owns the customer, they own you.

Own the data. Own the list. Own the relationship. Always.

Your growth rate and profit margin should add up to at least 40%.

20% growth + 20% profit = solid. 25% + 25%? Even better.

Do that consistently and you’ll double revenue every three years without starving your margins.

Growth is exciting. Profit is oxygen.

You need both to stay alive long enough to win.

At some point, someone will hand you Traction and tell you to find an Integrator. Don’t.

You can’t outsource your chaos.

You need to learn how to run your business first…how to build an operating system, how to track metrics, how to lead effectively.

Then, once the system exists, you can hire someone to run it.

Operators don’t fix broken systems…they operate existing ones.

Build first. Delegate later.

You don’t need five “income streams,” you need one that actually works.

Most founders fail because they never go deep enough to achieve mastery. They keep chasing the next big idea instead of scaling the one that’s already working.

Focus is a force multiplier.

You’re not Elon. (And that’s okay.) Get one business right before you start collecting new ones.

Everyone says, “Hire for your weaknesses.”

They’re wrong.

Hire people who make you better at what you’re already great at.

There’s a reason your business exists…it’s because of something you do exceptionally well. Double down on that.

Hire to amplify your genius, not to outsource your discomfort.

Once that core is solid, you’ll have the margin to backfill the rest.

Show me your calendar, and I’ll show you your priorities.

In 2016, mine showed I loved my business more than my wife and kids. I didn’t say that, but my schedule did.

Now, my wife and I meet every December to block family vacations and date trips before business planning even begins.

If your business takes everything, it’s not a business…

…it’s a prison.

Don’t build something that costs you the very people you’re building it for.

You’ll want to quit. Probably more than once.

That’s normal. Just don’t make the decision when you’re exhausted.

I once fired myself after a terrible stretch, brought in someone new, and nearly wrecked the company.

My new rule: I’m allowed to quit…just not on a bad day.

(Funny thing…after a good day, I never want to quit.)

All these lessons point to one truth: Scaling isn’t about doing more, it’s about doing fewer things better.

You don’t need to become a new person to scale, you just need to stop doing the things your 25-year-old self thought were smart.

⚡️Action Step: Pick one of these ten that stings the most. That’s probably the one you need most. Now, take 10 minutes TODAY and make one small move to fix it, because experience is the best teacher, but learning from someone else’s mistakes is way cheaper (and a lot less painful.

P.S. I’m looking for 5 business owners who want to work 1-on-1 with my team and me to install a custom “operating system” so your business can scale and so you can exit the day-to-day. Click here to get the details.