What I would tell my 25 year old self about money, risk, and starting over

I was 25 in 2002. I had just started Penebaker Enterprises, my commercial roofing and sheet metal company. I had more confidence than cash, more ambition than knowledge, and a genuine belief that working harder than everyone else would solve everything.

Twenty-four years later, I know what I wish I’d known then.

TL;DR: At 25, I started a roofing company with more confidence than cash. Looking back, I’d tell my younger self to get an accountant earlier, fire faster, save more, and stop equating exhaustion with productivity. Here’s the advice nobody gave me.

Get an accountant before you need one

I did my own books for the first two years. Not because I was good at it, but because I thought paying an accountant was a luxury I couldn’t afford. I was wrong. I could not afford not to have one.

By the time I hired an accountant, I had underpaid taxes for two quarters, missed a deduction that would have saved me $8,000, and organized my receipts in a shoebox. Literally a shoebox.

An accountant at $300 a month would have paid for herself ten times over. Get one before you need one.

Fire faster

Every bad hire I kept too long cost me more than the one I let go too early. I kept a project manager for 14 months because he was likable, even though he was consistently missing deadlines and blaming his crews. By the time I finally terminated him, two good employees had quit because they were tired of picking up his slack.

If someone isn’t working out and you’ve given them honest feedback and a real chance to improve, make the call. Waiting doesn’t make it easier. It makes it more expensive.

Save money like the recession is tomorrow

I made good money in the mid-2000s. I spent it like the boom would last forever. New truck, new equipment, expanded the office. When 2008 hit, I had six months of runway and twelve months of obligations.

I survived, but barely. If I’d saved 20% of every good year instead of 5%, the recession would have been uncomfortable instead of nearly fatal. Young me thought saving was for people without ambition. Older me knows it’s what keeps ambition alive.

Stop confusing exhaustion with productivity

I worked 80-hour weeks for years and wore it like a medal. I’d tell people how early I woke up and how late I stayed like it proved something about my character.

It didn’t. It proved I was bad at delegating, bad at setting boundaries, and using work to avoid other parts of my life that needed attention. The 80-hour weeks didn’t build the business. They burned me out and nearly cost me my family.

The business actually grew faster once I cut back to 50 hours and hired people I trusted enough to handle the rest.

Your reputation is your retirement plan

In the trades, word of mouth is everything. I’ve gotten million-dollar contracts from referrals and lost them from a single bad review. Every interaction, from the guy at the supply house to the client’s assistant, shapes how people talk about you when you’re not in the room.

At 25, I thought reputation was something you earned once and kept. At 48, I know it’s something you earn every day and can lose in an afternoon. Protect it.

The last thing

I’d tell 25-year-old me to call his stepmom more. To show up for his brother’s stuff. To not wait until a crisis to tell the people in his life that they matter. The business will survive a missed afternoon. The relationships might not survive a missed year.

Last updated: March 13, 2026