Entrepreneurship is often sold as a dream. Inspirational LinkedIn quotes, founder stories ending in IPOs or exits—it all paints a pretty picture. But after ten years of building, breaking and rebuilding, I’ve learned that the reality is much messier.
Here’s what I know:
- Scaling isn’t glamorous.
- The "overnight success" stories are usually a decade in the making.
- And failure? It’s not an option; it’s your initiation fee.
If you want the truth, here it is: You’ll make mistakes. Your plans will blow up. People will let you down — and you’ll do the same to others.
Entrepreneurship isn’t about having it all figured out from the start; it’s about adapting, pivoting and occasionally face-planting on your way to the next big thing. The key is learning, adapting and building momentum through all the messy moments.
Here are ten hard-won insights I wish someone had handed me on day one. They’re hard-earned, often expensive and painfully simple. But if you absorb even one of them, it might just save you a year of setbacks — or at the very least, a couple of sleepless nights.
- Big ideas matter, but execution pays the bills.
People love big talk about “moonshots” and “world-changing ideas”—but here’s the reality: ideas are the easy part. If you can’t roll up your sleeves and execute on them, you’re just playing mental gymnastics. The real differentiator? Consistent, relentless action. Week in, week out. Fancy pitches are great, but it’s the follow-ups and unglamorous day-to-day that get results.
Think big. Ask, “How can we 10x this?” Then break down your goals, tackle them piece by piece and keep moving. At WithMe, we don’t scale on vision alone; we thrive by stacking small, consistent wins, building momentum step-by-step. Fancy pitches won’t pay the bills, but focused, gritty follow-through will.
My tip: Track your team’s progress on micro-wins. Those add up fast.
- Growth doesn’t happen by accident.
Scaling isn’t something that just “happens” if you’re in the right place at the right time. If you want exponential growth, you have to be intentional and take risks. That often means tearing down something you thought was working and rebuilding it with new insights.
You have to be intentional. That means asking yourself uncomfortable questions: What’s working? What’s not? What’s the bottleneck?
If you want 10% growth, tinker. If you want 10x growth, rethink everything. Big leaps require uncomfortable choices and serious risk-taking. Growth only happens when you let go of ‘good enough.’ If you’re not rethinking the fundamentals regularly, you're just coasting.
My approach: Regularly challenge the status quo. If something is only “good enough,” it’s time to rethink.
- People are your greatest investment.
Hiring the right people is like collecting rare art. The best talent isn’t always on job boards; they’re out there doing great work. Finding these people requires patience, vision and sometimes years of connection-building.
Some of the best people I’ve hired were conversations years in the making. Play the long game with talent acquisition. It always pays off.
Remember, the best talent isn't on the market — they’re out there waiting to be discovered. When you find them, move fast. Pay upfront in value, and over time, they’ll return more than you imagined. When you spot someone with the right spark, act fast.
Pro tip: Find smart people, pay them well and get out of their way. When you spot a standout talent, move fast.
- Leadership is serving your team.
The most effective leaders serve their teams by removing obstacles, providing direction and stepping aside. If you think your team works for you, you’ve already lost. Your job is to clear obstacles and make sure they have everything they need to win. Enable people to perform at their highest level—and that starts by empowering them to own their roles.
Key insight: Leadership isn’t about control—it’s about service. If you’re micromanaging, you’re bottlenecking your business.
- Don’t confuse movement with progress.
Being busy doesn’t mean you’re being productive. There have been weeks where I felt like I was running on a treadmill—doing a lot but moving nowhere. Progress is about completing the right things, not just checking off endless tasks.
Here’s how I spot wasted effort: If it’s not moving the needle, it’s a distraction.
My rule: Ruthlessly prioritize what matters, and let the noise go.
- Mistakes will happen. Own them.
No one gets through entrepreneurship without a few bruises. I’ve micromanaged when I should have trusted my team. I’ve raised more capital than I could deploy effectively. But every mistake became a lesson that shaped how I lead today. Create space for yourself (and your team) to learn from missteps.
You’ll screw up—more than once. It’s part of the game. Admit your mistakes fast, learn from them and move on. No one has time for excuses. The trick is to own those mistakes fast, learn from them and get back on track.
Pro tip: Create a culture where your team feels safe to fail and learn. If they’re too afraid to make mistakes, they won’t push boundaries—and neither will your company.
- Competitors are a distraction.
It’s easy to get obsessed with what the competition is doing. But unless they’re paying your bills, their moves shouldn’t drive yours. Focus on listening to your customers and solving their problems. Listen to their pain points. Build solutions that genuinely help them—and your growth will follow.
Markets evolve, and so do your customers' needs. Obsess over meeting those needs better than anyone else.
My approach: Keep your head in your game and stick to your strategy. Outflanking competitors is easy — listen to customers louder than they do.
- Your best salesperson is a happy customer.
No ad campaign can compete with a customer saying, “You need this.” The strongest growth comes from people who genuinely love what you do and tell others about it. A product with undeniable value creates advocates naturally.
Nail your product-market fit, and customers will sing your praises.
If your product isn’t generating enthusiastic referrals, it’s time to go back to the drawing board.
Takeaway: Build something that people love so much, they can’t help but tell others. Happy customers are the lifeblood of sustainable growth.
- Not every fire needs your attention.
In a growing business, there are always fires to put out. But knowing which fires matter—and which ones to let burn—is a game-changer. Early on, I tried to handle everything myself. Now, I triage: if it doesn’t impact the long-term vision, it can wait.
You’ve got limited time—spend it on the fires that actually matter. The art of prioritization is everything.
Lesson learned: Prioritize only the fires that matter. Not every problem deserves immediate attention.
- Sometimes, the best move is no move.
In moments of stress — a sleepless night, a tough quarter or a rough meeting — pause. Acting rashly rarely helps. Inaction, when applied wisely, can prevent avoidable damage and keep trust intact.
When you’re overwhelmed, resist the urge to react impulsively. I’ve learned the hard way that acting while exhausted, stressed or frustrated rarely ends well.
My advice: Sleep on it. Most problems can wait a day. The ones that can’t? They’re rarely solved with rushed decisions.
Enjoy the journey, or what’s the point?
If you’re always chasing the next thing, you’ll miss the good stuff. The best moments aren’t just milestones—they’re found in the chaos along the way.
There’s always another mountain to climb, but if you don’t enjoy the journey, what’s the point? The biggest wins come in unexpected places—sometimes between meetings, other times during failures that seem devastating at first.
Entrepreneurship isn’t a straight line. It’s messy, unpredictable and exhausting—but it’s also incredibly rewarding if you stick with it. Just remember: It’s okay to stumble as long as you keep moving forward.
Reality Check: You’ll Wear Every Hat—and You’ll Still Drop a Few
In the early days, I was the CEO, customer support, IT troubleshooter and supply chain manager. You name it. And yes, things still slipped through the cracks sometimes. That’s just reality. As we grew, I learned the importance of building a strong team—one that could take some of those hats and wear them even better than I could. Eventually, I learned the importance of knowing which hats I could keep and which I needed to pass on to someone better suited for them.
As WithMe grew, I made a conscious choice to hire people who were stronger than me in specific areas. This wasn’t easy; it meant letting go of control and trusting my team. But it was a game-changer. Each person I brought on brought something unique that took WithMe to the next level. The lesson? You might start out juggling it all, but eventually, you need to step back and let others wear some of those hats. That’s when your team—and your business—will really take off.
Advice: Hire people who are better than you at specific things and let them shine.
The Bottom Line
Ten years in, and here’s what I know for sure: you’ll never have it all figured out—and that’s okay. The journey is about learning, evolving and staying curious. If you can embrace that, you’ll find that every setback is a step forward and every challenge is an opportunity to grow.
The journey isn’t always glamorous, but it’s worth every stumble. These 10 lessons? They’re battle-tested and scraped together from 10 years of face-plants, late nights and surprising wins. Take them in, and they might just save you a few trips down the “What the heck am I doing?” road.
And if you’re curious how WithMe is applying these lessons to reimagine multifamily living, check us out. From simplifying daily life to creating standout resident experiences, we’re just getting started.
