Everything I've Learned from 10 Years in Business

My company, Rogue Pine, just celebrated its 10th Anniversary last month.

To celebrate, I decided to compile all the best lessons I’v learned over the last decade.

Some of these rules, I learned from smarter people than me.

Most, I learned by doing it wrong the first time.

The former is less painful but the latter tends to stick.

(Maybe that should be one of the rules 🤔)

Let’s get straight to it…

1) The buck stops with you (and that is plain hard).

You never truly get time off. You own all the risk, all the time. And no one is coming to save you.

2) Your spouse is your business partner.

Whether they’re involved in the day-to-day or not, your partner in life is your partner in business.

Their support (or lack thereof) will make or break you.

I got extremely lucky on this one 😃.

3) Your kids’ lives will be different from their peers.

They might not realize it now, but your role as a business owner will have a unique impact on them.

4) Nurture your network.

Build it, track it, and for goodness' sake — use it.

You should be one call away from whatever or whoever you need.

5) Surround yourself with doers.

People who have “been there” will offer wisdom, encouragement, and reassurance when you need it most.

6) You will suck at first.

You probably haven't done that thing for long enough or consistently enough to know if it’s working yet.

You have to put in the reps.

Consistency is often the missing ingredient.

7) Remember, the mind lives inside the body.

When things get busy, you will lose sleep, your nutrition will suffer, and you won't get to the gym as often.

Just make sure you adjust as often as needed.

8) Speaking of your mind...

You can literally create your own reality.

If you can see it in your mind, you can hold it in your hand.

9) Learn from your mistakes.

The first time is an accident.

The second time is a choice.

10) Make the most of your flexibility.

Don’t apologize for structuring your days differently.

Yes, I'm at my sons school event on a Tuesday at 10am.

I may also be up until midnight, but it's my choice.

11) Revenue is great, but profit is meaningful.

That said, you need a meaningful amount of revenue to generate enough profit for it to matter.

So, focus on revenue until you're able to cut expenses and drive profits.

12) Pay yourself first.

Systems like Profit First make sure the big guy gets paid (that's you!).

13) Embrace tax advantages.

As a business owner, you will get tax advantages.

Do not apologize for this. This is how they incentivize job creation.

14) Plan for a bigger tax bill as you grow.

Tax breaks won’t mean less tax in the long run.

Eventually, the tax man will come for his pound of flesh.

Prepare accordingly.

15) Keep overhead low.

Regularly review expenses to avoid unnecessary financial strain.

16) Watch for sneaky cash leaks.

Fees and forgotten subscriptions add up fast.

We trimmed about $10K from our budget last year just by removing a bunch of unnecessary expenses.

17) Sales cures all.

Even if it doesn't, it'll sure make you feel better.

18) Get comfortable with difficult hiring and firing.

Hiring is hard, and letting people go is harder.

Get it right from the start.

19) Make hiring a pain.

The tougher your hiring process, the less often you’ll need to part ways later.

Get clear agreements in writing.

20) Think twice about hiring friends.

I have become friends with someone I've hired more times than I've stayed friends with a friend I had to let go.

21) On being a faith-based business owner (or whatever they're calling it at Lifeway these days)...

A mentor once said that, "If I see a Bible verse on a business card, I hide my wallet."

Don’t say it. Show it.

22) On productivity...

A notebook with time blocks for each task often beats any fancy app.

23) Grit is great, but systems scale.

Systems work for you even when you’re not working.

Just make sure the system serves the goal—not the other way around.

24) Plans are useless, but planning is indispensable. — Dwight D. Eisenhower

Without vision the people perish.

Without a plan, the vision is just a dream.

Without the work, a plan is worthless.

Dream → Plan → Work.

25) Write it down.

Nothing helps you think clearly like writing it down. Get it out of your head and see it objectively on paper.

26) Metrics matter, unless they don't.

Metrics are helpful, but if the metric becomes the target, it ceases to be a useful metric.

27) Build your email list early.

In 10 years owning the agency and 15 in marketing, nothing beats email marketing.

When we send emails, we make money.

28) The most important word in marketing is "exactly."

When people say, yes, exactly! you’ve already won.

29) Start creating content today.

Even if it’s rough and unnoticed at first, you’ll be glad you have an archive of your ideas.

30) Be a Go-Giver.

The best way to get what you want is to help enough people get what they want.

31) Beware the tyranny of the urgent.

The siren's song is hard to fight. But fight it, you must.

32) Answer your daggum emails!

That's it. That's the whole tip.

Just being responsive can be a differentiator.

33) Remove friction wherever possible.

Always look for ways to simplify—fewer steps, quicker solutions, automation.

34) Remember that AI is for organizing, not creating.

Use AI for efficiency, but creativity and original thought are still your job.

Best Content We Found This Week

Seemed appropriate, given this week’s theme.

See you next week.

-Reade