I still remember the first time I decided to start a company. I was 15, thought I was invincible, and had just enough of an ego to believe I could pull it off. What I didn’t know was that I was signing up for a lifetime of sleep deprivation, existential dread, and an unshakable addiction to the entrepreneurial rollercoaster.

Fast forward 25 years, 15 companies, and more battle scars than I care to admit, and I can tell you one thing with absolute certainty: if you’re about to start your first company, you have no idea what’s coming. And that’s fine. None of us did. But let me save you a few (or a dozen) painful lessons so you don’t have to learn everything the hard way.

Lesson #1: You Need More Money Than You Think. No, Even More Than That.

When I launched my first company, I had a rock-solid financial plan — at least, I thought I did. Within six months, my savings account and my plan had been completely obliterated. Whatever number you think you need to raise, double it. No, triple it. Then, for good measure, assume you’ll still need more.

Start-ups are money-eating machines. Your burn rate will be higher than expected, unexpected expenses will hit like a wrecking ball, and investors will take twice as long to wire funds as they said they would. The faster you accept this, the better.

One of my favorite quotes is from Twitpic founder Noah Everett: “Don’t worry about funding if you don’t need it. Today, it’s cheaper to start a business than ever.” Great advice — if you’re selling digital products or living in your parents’ basement. For the rest of us? Get the money.

Lesson #2: Be Wary of the “Keep Going!” Cheerleaders

Look, I love a good pep talk. But there’s a specific type of person in your life — often friends or extended family — who will throw out empty encouragement like “Success is right around the corner!” or “Just keep pushing, it’ll all work out!”

These people mean well, but they are useless in times of crisis. You don’t need cheerleaders. You need people who will challenge your ideas, call out your blind spots, and occasionally shake you by the shoulders when you’re about to make a terrible decision. Find those people. Keep them close.

For me, that person was an old mentor who, after my second company started flailing, sat me down and said, “Listen, you don’t have a business problem, you have a ‘you’ problem. Fix your leadership, fix your business.” Brutal? Yes. Necessary? Absolutely.

Lesson #3: Getting on Shelves is Easy. Getting Off is What Matters.

Back when I was pushing a consumer product, I landed a massive deal with a national retailer. I was convinced I had made it. This was it — I had arrived.

Two months later, I was drowning in unsold inventory, buried in chargebacks, and learning a painful lesson: getting a retailer to say “yes” is easy. Getting customers to actually buy your product is where the real work begins.

Retail is ruthless. If your product doesn’t move, you’re discontinued faster than a failed Netflix series. If you ever find yourself celebrating shelf space, remember — the real battle has only just begun.

Lesson #4: If You Think Your Product Isn’t Ready, It’s Not.

You know that tiny voice in your head whispering, “I don’t think this is good enough”? Listen to it.

In one of my early ventures, I had an MVP that was fine. Not great, but fine. I ignored my gut, launched anyway, and within weeks, I had customers demanding refunds and leaving reviews that could only be described as emotionally scarring.

Kevin Rose, co-founder of Digg, once said, “Don’t let others convince you that the idea is good when your gut tells you it’s bad.” Trust me — if you’re having doubts, your customers will, too. Fix it before you launch.

Lesson #5: Hire People Who Can Do What You Can’t.

Early on, I had a bad habit of thinking I could do everything myself. I’d jump into marketing, operations, product development — like some kind of caffeine-fueled Swiss Army knife. Turns out, I was mediocre at most of it.

The moment I started hiring people who were good at the things I sucked at, everything changed. The best founders aren’t the ones who do everything — they’re the ones who find great people and get out of their way.

Lesson #6: Free Press? You’re Dreaming. Make Your Own.

You think Forbes is going to magically write about your startup? That TechCrunch is dying to cover you? Hate to break it to you, but no one cares.

Early on, I wasted so much time chasing journalists and PR firms, only to realize that the best way to get attention is to make your own noise. Tell your own story. Build a brand. Make people pay attention.

Brian Chesky, co-founder of Airbnb, put it perfectly: “If we tried to think of a good idea, we wouldn’t have been able to. You just have to solve a problem in your own life.” When you do that, and you tell that story well, people will listen.

Lesson #7: Stop Comparing Yourself to the Lucky Few.

Some founders had rich parents. Some went to Yale. Some had VCs on speed dial before they even had a product.

You? You’re playing on hard mode. And that’s fine. But if you spend all your time comparing yourself to people who started the race at the finish line, you’re going to drive yourself insane.

Every founder’s path is different. The only thing that matters is what you build.

Lesson #8: Your Employees Are Not Robots. Treat Them Like Humans.

Here’s what I don’t care about as a founder:

✔️ When my employees work.

✔️ Where they work from.

✔️ If they take mental health days.

✔️ If they work less than 40 hours.

Here’s what I do care about:

✔️ That they’re happy.

✔️ That they have a work-life balance.

✔️ That they feel fulfilled inside and outside of work.

✔️ That they know I have their back.

I hire people because they’re great at what they do. I trust them to do their jobs. Everything else is noise.

How Startups Are Changing (And How You Should Adapt)

With funding rounds getting smaller, here’s what matters now:

1️⃣ Capital Efficiency — Every dollar has to move the needle. No more vanity spending.

2️⃣ Better Starting Positions — Investors want more proof before they invest. Have real traction.

3️⃣ Customer Obsession — Less time pitching VCs, more time building something people actually want.

Final Thought: It’s a Mess, and That’s Okay.

If I’ve learned one universal truth after all these years, it’s this: never assume there’s a grand conspiracy when simple incompetence will do.

Most of the time, things break not because someone is out to get you, but because startups are messy, people are overloaded, and we’re all just making it up as we go.

So take a deep breath. Assume good intent. Keep moving forward.

Building a startup is the hardest thing you’ll ever do. It will test you in ways you never expected. Some days, you’ll feel unstoppable. Others, you’ll question everything.

But if you can survive the chaos, stay focused, and execute relentlessly, you’ll win.

And if not? Well, at least you’ll have one hell of a story to tell.

Now get back to work.