30 Years In Business Taught Me These 30 Lessons...

Mark Evans DM

As I sit here in my home office in Parkland, Florida, looking out at the golf course, I'm watching a handful of guys chase that white ball around. The weather is a perfect 86 degrees, the sun is beaming, and there's this killer breeze rolling in.

Honestly? I gotta pinch myself.

I wanted to take a moment to sit down and write out 30 entrepreneurial lessons I've learned over 30 years of being in business. What's wild is that I don't even feel 30 years old (I'm 47 as I write this), let alone 30 years deep into the game. In 15 days, I hit the ripe old age of 48, and let me tell you ... time has some serious horsepower. It just flies.

Let's rewind back to June 4, 1996.

I had literally just graduated high school with a whopping 1.8 GPA... and I was standing at that fork in the road.

Do I go punch a clock for someone else... or build something of my own and make my own money?

Now, I've always been obsessed with "the hustle"

Mowing lawns, selling my sister's toys, trading baseball cards ... you name it, I tried to sell it.

You see I grew up in a trailer park, and watched my parents bust their tails every single day just to barely scrape by.

I knew I didn't want that life for me or for them, and as a kid, the only solution I could see was to make more money.

I can still picture exactly where I was sitting in my parents' house when I made what would become the biggest decision of my life.

At 18 years old I decided to buy a seamless gutter company.

A thousand bucks down and $287 a month. That was literally every single penny to my name. I didn't have a safety net, but I had a relentless work ethic (thanks to my parents for drilling that into me) and I had a vision of where I wanted to go. At that time I had absolutely no clue that 30 years later I'd be sitting here writing this to you.

What's even crazier is that the owner of this seamless gutter company, guy's name was Larry, actually believed in a kid fresh out of high school enough to finance the deal.

Honestly, he was a wheeler-dealer, and to him, I was probably just another transaction on a Tuesday.

I'll never forget standing on his front lawn, stumbling over my words, trying to sound like a businessman while making him an offer.

But he had no idea what that deal did for my life. RIP, Larry.

When I look back on that kid, I get so damn excited about how far we've come. But in that very same thought, that entrepreneur's brain kicks in…

  • How am I not further along?
  • What did I do wrong?
  • What did I miss?
  • How could I have scaled bigger?
  • Why didn't I say "no" to the distractions and "yes" to the right things?

If you're in the game, you know exactly what that self-doubt feels like.

But truth be told, chasing those "what-ifs" is a waste of energy.

The reality is that the life I'm living right now in Parkland is a dream I didn't even know existed back then. Every single decision... good and bad... brought me to this exact moment.

It's easy to get stuck in the comparison trap. People say comparison is the thief of joy, but I actually look at it differently. I love comparison... not to feel bad about myself, but to see what's possible in this crazy, beautiful thing we call life.

Maybe it's a maturity thing, but back in the day, my benchmarks were whatever I saw on TV.

I'm talking Magnum, P.I. and his red Ferrari...

J.R. Ewing running the show on Dallas...

Or Robin Leach hosting Lifestyles of the Rich and Famous...

I used to watch those guys and think, if they can have that life, why the hell can't I?

I didn't have a roadmap, but I had three things:

  • Faith.
  • Execution.
  • And the grit to do the work, even when I had no clue how it would get done.

I have never, not once in my life, been afraid of the work.

But let's get real for a second....

Why do we beat ourselves up so much in this game? We all have that toxic inner dialogue running in the background:

  • I should be further ahead by now.
  • I should have a bigger house.
  • I shouldn't still be dealing with employee drama.
  • I shouldn't have these cash flow tight spots.
  • I wish I had more time with my kids, my wife, my family.

We all hear those voices. True entrepreneurs are just wired differently. It's not that we aren't grateful ... in fact, most business owners I know are deeply thankful for what they have. It's just that we are our own worst critics.

Today, I'm incredibly blessed. I have the resources, the cash flow, the equity, and the assets. More importantly, I get to spend serious, quality time with my wife and kids. But I still want to push for more. Not because I'm greedy for another dollar, but because we only get one shot at life and I want to see just how good the best version of myself can get.

There will always be someone with more, and someone with less. For me, it's about honoring whatever time I have left here by executing at the highest level while keeping my priorities locked in.

I'll be the first to admit. I was a bit of a dick when I first started out. I didn't know any better. I drove my team incredibly hard. But the saving grace was that I was right there in the trenches with them ... not some boss sitting in an air-conditioned office barking orders. I was sweating right alongside them. It wasn't the healthiest way to manage, but hey, we grow up.

My days look a lot different now.

These days, I'm all about priorities, not "balance." Balance is a myth. Let's call it what it is: your priority structure in years zero to five when you're single with no kids is going to look vastly different than mine. If you've been in the game for 20 years, have a family, and you're still grinding like a single twenty-two-year-old, your priorities are out of whack.

Here's what my days look like now:

Friday Morning Dates. Every Friday from 8:15 to 10:00 AM, my wife and I have a standing date. We go to a quiet little spot, sit down, and just talk. No agenda, no phones, just catching up on life.

Early Morning Workouts. I get up before the sun so my training doesn't steal time from the family. That hour belongs to me, and it sets the whole day up right.

Waking Up the Kids. My son is already an early riser like his dad, but at 7:30 AM I love waking my daughter up and carrying her downstairs to have breakfast together before her homeschool teacher arrives. I know this is a season of life, and once it's gone, it's gone forever.

Being Present. I make it a hard priority to be at my daughter's gymnastics at 2:00 PM and at their tennis lessons three times a week. Non-negotiable.

Is this schedule convenient? Hell no.

But let me tell you. it is worth every single ounce of effort.

This window of time is temporary.

Kids grow up incredibly fast, and you can't wind that clock back.

You have to be hyper-conscious of the game you're actually playing. Figure out your non-negotiables, set your priorities, and then build your business schedule around that ... not the other way around.

You're not going to hit a perfect 100% every day, but the goal is to keep aiming for it.

So, let's get into these 30 lessons from 30 years in the trenches.

And to be completely honest with you?

I'm learning more today than I ever have before,,,

1. Work-Life Balance Lie

If you are a success in business and a failure at home you have lost the game of Life no matter what lie you tell yourself. Life comes in seasons: Winter (business is cold), Spring (new ideas/things picking up), Summer (things are steady), and Fall (things slow down), so know the season you're in and have priorities in place. A true entrepreneur doesn't have balance, we have priorities and those will constantly change.. So make sure you include family and life on your list …. It's not just all about working, building, and acquiring. I care more about my family way more than any business deal I have done or will do.

2. Fall In Love With The Journey

Truth is most are so focused on the destination and thinking it's going to be the end and this big celebration. But it's not. It's just another stepping stone to the next stepping stone. Commit to becoming 1% better every day and enjoy the ride …. because there is no end … well, until your time is up. ;)

3. Your Why?

This changes as we evolve but rest assured I still have the chip on my shoulder and use that negative talk as FUEL. My "why" when I started was to make as much money as humanly possible with the skills I had, and back then it was back breaking construction work which I'm glad I had the privilege of doing at a young age, as mentioned the "why" is different in seasons of the journey.

4. You are YOUR best investment

Go ALL in on you. You're worth it. Mentors, masterminds, meet ups, podcasts, read and read more. Damn near everyone will tell you "it's scam" or "if they were so rich why wouldn't they just be doing it" These are the same people telling you to go to college and playing it safe. Listen … I 100% wouldn't be going 30 years strong in business if I didn't go ALL in on me. I paid for access even when I had to put in on a credit card. I "burnt my ships" … I trusted in me … and once I saw the path I put in the work.

5. Consistency in progress is your friend

You may have heard me say "you're either consistent or non existent" which is sort of correct with context but if you're consistent about going to the bar, talking about the gossip and such well the outcome isn't going to be too good. I got consistent on getting up early, reading books, executing ideas, door knocking, cold calling, showing up to the jobs on time and going above and beyond. This isn't a gift by the way, this is a learned behavior. I had to STOP hanging with the "King of the Dipshits" crowd in order to get to the next level.

6. Who Not How

You need to learn to delegate work, but with a caveat …. don't try to over delegate before you actually get started. I see many that are delegating delegation ;) ... don't be that person. Get in the game and start learning how to "let go"... and trust me many folks will do it better than you … as most have a fallacy that if I want it done right I have to do it myself. ;)

7. Prioritize Health

Your health is your wealth… plain and simple. When you feel good, your business reflects it. I learned this the hard way after grinding way too hard for way too long and letting my body pay the price. Not worth it. Now I treat my health like a non-negotiable part of my day, and everything else runs smoother because of it. Take care of yourself first … the business stuff is a lot easier when you're not running on fumes.

8. You're Either Growing or You're Dying.

Never get complacent. The World is dynamic. Continually evolving helps you stay relevant and competitive in business. (You hear that Blockbuster) Always improve, always add on products/services, always test new marketing channels .... the moment you let off the gas .... is the moment you start to die.

9. Lessons Not Losses

You will learn more from your failures then you EVER will from your wins. Don't let a loss derail you for too long. Many folks take an L and let it control their life forever. Learn from it, and get back to work.

10. Borrow Belief

I didn't know what was possible. I only knew what I knew. Get in the right rooms where folks are talking about growth and the future, NOT the past and why they can't do something. The room matters. Latch hold of the right person that is where YOU want to be and borrow their belief until it becomes your own.

11. Invest in Branding

Branding is more than just a logo or tagline. It's a lifestyle. And we all lean towards brands. Think Harley Davidson, Nike, Louis Vuitton, Deal Maker ;) they mean something way more than a logo and tagline; it's a lifestyle. What does your brand say about you?

12. Be Curious

We've all heard the saying "Curiosity killed the cat." Well, I can tell you that I have made many millions by being curious about how things work and bringing solutions to market to solve problems I found during the process.

13. Be Impatiently Patient

I get it everyone will tell you to be patient, things take time, and many are right. But most use that as an excuse to drag their feet. I like urgency on things and it's served me well but also maturity in the game will teach you where to be patient vs others using that as an excuse.

14. You Don't Gotta Get it Right, Just Get It Going

Too many people wait for the perfect moment or the perfect plan. The first step doesn't have to be flawless, it just has to be taken. Start messy, start unsure … but just start. If you're waiting for all the answers … you'll be waiting for the rest of your life. You don't gotta get it right, just get it going.

15. Relationships over Transactions.

This is why I still do deals with guys I've known for 25+ years. I've never been interested in doing business with someone one time and then bouncing. Unless of course I didn't like how they did business … then it's a one and done. I'm more interested in building a relationship with you and helping you along your journey, and vice versa. I actually care about seeing people I work with do better ** GASP ** crazy concept, right?

16. Know What You DON'T WANT

"I want to be a billionaire!"

Do you? You wanna fly around the world ... sit in boardroom meetings all day ... and have zero life outside of the business? Stop pulling numbers outta your ass ... reverse engineer your dream life, not the life of someone else that doesn't know what they want. Get serious and write this down. You'll be shocked at what you see.

17. Always Build to Sell

Even if you want to work until you're 100 years old ... building to sell gives you options. Plus it allows you to run an operation that doesn't rely on you. So take 2 weeks off. Take 2 months off. Build your company around systems, procedures, and amazing people. It'll be more valuable in ways other than a big multiple.

18. Don't Sell Anything You Wouldn't Sell Your Own Mom

We all sold products/services when we were younger that we knew were decent. We just sold them because the numbers looked good and the product/service got the jobs done.

But it wasn't the best! (even though we said it was)

Start selling stuff that you're TRULY proud of ... stuff you'd "die on hill" defending ... stuff you'd want your own Mom to take/buy … I don't care if I make a few bucks less on the sale. Because I KNOW that customer will come back to me and/or refer other customers my way.

19. Be a Man of Your Word, Even When It Hurts

Do what's right. Even when it sucks.

This means having those tough conversations.

Your reputation is your brand. It speaks for you even when you're not in the room. So guard it with your life. I don't care what names people call me … but one thing I know to be true, is no one can say I'm not a man of my word.

20. Give, Give, Give

Money is great. But it's just a tool. There comes a point in every wealthy person's life when the "high" of buying another exotic car, another home, another whatever ... does NOTHING for you.

Being able to do cool things and have nice stuff is great ... but the greatest feeling that only gets better is the ability to give back to someone who's lost hope, got hit with something they didn't see coming, or someone who is just eeking by. Being able to help take a bit of pressure off their chest, and let them breath …. Man oh man … makes me tear up just writing this.

21. Old School Check In's

In a world of automation, emails, social media, and now AI ... sending someone: a customer, friend, family .... a short personal video from your phone or a letter just checking in and letting them know you're thinking about them .... with NO MOTIVE other than a "hey hope you're doing well, here if you need anything" ... it means more than you'll ever realize.

22. Drop The Ego

In the world of business owners .... you got guys who think their Gods. That they can do no wrong, and shit on anyone they can. When you first start making some money ... it can make you act a certain way. Fight that. Because you will get humbled and quick! Truth is ... we're all learning, we all have doubts, and we all mess up from time to time. Drop the act … it ain't fooling anyone and it ain't helping you.

23. Hire Wrong and You'll Pay The Price

Only hire family and friends if they share your work ethic. You can teach skills but you can't teach work ethic. And the second you bend rules for them and play favorites, because they all 'expect' it, you are building a disaster you won't see coming til everything goes down in flames.

I was once in a partnership where my partner only hired his wife's family and friends. Every one of them was more unqualified, undisciplined and full of hidden envy than the next. It created the most toxic, suffocating environment imaginable. Don't get caught up thinking you gotta 'save' people who don't even want to be saved. Take a chance on an 'outsider' who's hungry and their dreams align with your own.

24. Don't Be Afraid to Say No

If the answer is no, just say no. Don't make other people's problems your problems. If it's a bad deal or doesn't meet your criteria, just say no and end it. Dragging it out when you already know the answer is pure cowardice. Think of how you feel waiting on an answer for days on end. The 'Golden Rule' of treating others how you want to be treated will never go out of style.

25. Overdeliver Everything.

Overdeliver on everything, any chance you can. For customers, friends, charities. Tip big and don't expect anything in return for it. Be known as the person who goes above and beyond and you'll never be forgotten. The more you do this in everyday life, the more natural it'll flow in your business. Even if you can't answer a text or email for a bit, shoot a quick 'busy now but got this' so they get acknowledged. The reputation you build when nobody's looking is the one that pays back most in the long run.

26. Data Not Drama ;)

Your feelings will lie to you about your business every day of the week, but the numbers won't. Don't get emotionally bonded with an idea that's got no track record of working. If it's not working and there's no clear plan to propel it forward, cut it and move on. Stop letting your friends or spouse cheer on something that's got massive problems with logistics and expense, just because it's something they 'think' will be a home run. Numbers tell the brutal truth and the faster you accept that, the faster you win.

27. It's Not a Sale Until Money Moves

A sale isn't a sale until the money's in your account. Read that again. Sharpen your ask for a sale and get a financial commitment. When you're the buyer, just make a damn decision. Back in the preconstruction boom we held onto a couple penthouse condos for a guy who'd already paid for three other units. After missing his deposit deadline he went silent. We scrambled to get buyers and had to slash our margins to make it work. Things happen and people sometimes have to back out, but don't start celebrating until the money clears the account.

28. Highlight Reels Don't Tell the Full Story. Regrets Do.

Ask people ahead of you how they got there and what they'd do over. What are their biggest regrets? Listen when they tell you, because it's almost always the simple things. One thing you'll never regret is paying attention to your physical and mental health. We think we're invincible in our 20s but when 40 comes up we realize we'd have done a lot different.

Don't act like a badass saying you 'have no regrets, it shaped you into who you are now'. Be humble and realize had you done things differently, you could have possibly helped thousands more people and be in better health, better finances, better overall today. And just start over now with that same mentality.

29. Motivation Lies. Discipline Is The Boring, Proven Path to Success

Discipline and motivation are two totally different things. Nobody gets successful being 'motivated'. Repeat the boring shit consistently even when you don't see results. It takes way longer than you think. It's annoying and monotonous. But it's the only true way to success. You don't pick up a dumbbell, do 1 set of curls and start looking for a massive bicep. You don't eat clean for one day and expect to be shredded the next. You build discipline from boring, ongoing habits with no sign of success in sight. That's the formula. It's also why so many people give up when it gets tough. Lack of discipline kills all dreams.

30. Who You Know Opens Doors You'll Never See Otherwise

Never underestimate the power of connections. A network will take you farther than you ever could alone. Back in the early 2000s one key connection shot us into a $250M+ partnership that's still ongoing in other ways today. Don't stay stuck in your small hometown clan if nobody there's growing. One right connection can transform your entire life. So just think if you had dozens of winners on your side. You know the saying "if you want to go fast go alone, if you want to go far go together".

30 years. 30 lessons. And honestly I'm still learning more now than I ever have.

If you take nothing else from this, take this…

The game is long. Most people quit right before it gets good. Don't be like most people ;)

If a kid from a small town in Ohio with nothing but a relentless work ethic and a chip on his shoulder got here then you sure as hell can too.

Go build your life.

Rooting for you,

Mark Evans DM