The path to executive leadership is rarely linear. Each scar tells a story, and each setback teaches a lesson. To help aspiring entrepreneurs and emerging leaders navigate their own journeys, we spoke with eight successful business leaders across diverse industries—from real estate and fitness to law and technology. Their collective wisdom offers a roadmap for avoiding costly mistakes and accelerating growth.
Here’s what today’s most successful CEOs wish they had known when they were starting.
The Power of Building Genuine Relationships
Brandon Hardiman, Owner of Yellowhammer Home Buyers, emphasizes that business success ultimately comes down to people. “I wish I’d understood earlier that your network isn’t transactional,” Hardiman explains. “Every relationship you build should be authentic and long-term focused. The deals that matter most come from people who genuinely trust you.”
This sentiment resonates across industries. Sain Rhodes, a real estate expert at Clever Offers, adds that relationships built on integrity create compound interest in your career. “The reputation you build today follows you forever. I spent years chasing quick wins when I should have been focused on becoming someone people want to work with repeatedly.”
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Don’t Hire Too Fast, Hire for Culture Fit
One of the most common regrets among growing business owners is scaling the team too quickly without maintaining cultural cohesion. Mike Aziz, co-owner of M1 Home Buyers, reflects on this challenge: “When you’re growing, the temptation is to fill seats immediately. But hiring the wrong person costs you far more than staying understaffed for a few months. I should have been much more selective about cultural fit early on.”
Armstrong Lazenby, CEO of Fitness Image Personal Training, echoes this concern in the highly personal fitness industry. “Your team becomes your brand. I learned that lesson the hard way by onboarding people with the credentials but lacking the passion for our mission. Now, I’d rather train someone with limited experience who truly believes in what we do.”
Master the Fundamentals Before You Scale
Carter Crowley, Owner of CB Home Solutions, wishes he’d spent more time perfecting his business model before expanding. “I was eager to grow quickly, but I hadn’t optimized my core operations. I’d tell my younger self: master your business at a smaller scale first. Scaling a broken process just scales your problems.”
This applies whether you’re running a home-buying company or a specialized service firm. Harrison Jordan, Founder and Managing Lawyer at Substance Law, emphasizes that building proper systems early prevents chaos later. “In law, we’re taught to be detail-oriented about cases, but not necessarily about running a business. I wish I’d invested in proper workflows, documentation, and delegation frameworks from day one rather than trying to retrofit them later.”
Understand Your Unit Economics
Financial literacy can make or break a business, yet many entrepreneurs operate without a clear grasp of their numbers.
Rafael Sarim Oezdemir, Head of Growth at EZContacts, expands on this: “Many founders assume that growth equals success. But if you’re not profitable at scale, you’re just burning cash efficiently. Understanding the financial mechanics of your business should be priority number one.”
Delegate and Let Go of Control
One of the hardest lessons for ambitious entrepreneurs is learning to delegate effectively. Ali Zane, CEO of IMAX Identity Theft Attorney Firm, reflects on the personal cost of holding on too tight. “As a founder, you feel like no one can do it as well as you. That’s partly true, but the cost of that belief is your own burnout and stunted growth. Delegation isn’t giving up control; it’s multiplying your impact through others.”
Brandon Hardiman reinforces this: “I spent my first five years doing everything myself. Looking back, I should have hired someone to handle operations within the first year. The money I would have saved in stress and the time I could have invested in strategy would have been worth far more than the salary I feared spending.”
Embrace Data-Driven Decision Making
In today’s business environment, gut instinct alone is no longer sufficient. Rafael Sarim Oezdemir emphasizes the importance of building data into your decision-making process from the start. “Technology has made it easier than ever to track performance, but many leaders still operate on intuition. I wish I’d implemented analytics and performance tracking earlier. The insights from data would have accelerated our growth by years.”
Chris adds that data should inform strategy, not replace judgment: “Data tells you what’s happening. Experience tells you why. The best decisions come from combining both. But you need the data first to even have this conversation.”
Invest in Your Own Education Continuously
Several leaders mentioned that ongoing education wasn’t a priority early in their careers. Armstrong Lazenby notes that the fitness industry evolves rapidly and that continuous learning is non-negotiable. “I was so focused on building the business that I neglected investing in my own skills and knowledge. Now I’m a lifelong student of business, psychology, and market trends. I should have started that practice years earlier.”
Harrison Jordan similarly notes that legal expertise alone isn’t sufficient to run a successful law firm. “I had legal knowledge but lacked business knowledge. Taking time to study entrepreneurship, finance, and leadership would have transformed my practice much faster.”
Protect Your Mental Health and Set Boundaries
One theme that emerged across nearly every conversation was the toll that unchecked ambition takes on personal well-being. Mike Aziz speaks candidly about this: “I wish I’d understood that sustainable success requires protecting your mental health and family time. Burnout doesn’t lead to better decisions; it leads to worse ones. Setting boundaries early would have made me a more effective leader.”
Ali Zane reinforces this sentiment: “You can’t build a great company if you’re falling apart personally. The best investment you can make is in your own health, relationships, and mental well-being. That’s not a distraction from business success, it’s the foundation for it.”
Build Your Brand Before You Need It
Sain Rhodes emphasizes the importance of building personal and professional credibility long before you need it. “Social proof, testimonials, case studies, reputation—these take time to build. I wish I’d started documenting our success and building our brand much earlier. When opportunities came, we were ready, but we could have been positioned even better.”
Chris Yan, CEO at Link Building Agency, stresses the importance of knowing your metrics inside and out. “I didn’t fully understand my unit economics for years. Once I did, my cost per acquisition, lifetime value, conversion rates, everything changed. You can’t optimize what you don’t measure.”
adds that in the age of digital marketing, visibility matters. “Many business owners ignore content marketing and public positioning. By the time you need a platform, it’s too late. Building your voice and authority in your niche should start before you’re desperate for clients.”
The Importance of Strategic Partnerships
Several leaders reflected on missed partnership opportunities early in their careers. Carter Crowley notes that partnerships can accelerate growth dramatically. “I was so focused on doing everything myself that I missed opportunities to partner with complementary businesses. Strategic partnerships would have opened doors much faster than going it alone.”
Rafael Sarim Oezdemir emphasizes that in the growth space, partnerships are often more valuable than advertising spend. “Finding partners who serve your target audience and can introduce you to customers is gold. I wish I’d prioritized partnership development over paid acquisition much earlier.”
Final Thoughts: The Wisdom of Hindsight
What emerges from these conversations is a clear pattern: the most successful CEOs didn’t get every decision right. They learned quickly, adapted, and focused on fundamentals while remaining flexible on tactics.
Brandon Hardiman offers a fitting conclusion: “If I could tell my younger self one thing, it would be this: the business you build is a reflection of the person you become. Invest in yourself, your relationships, and your systems. The success will follow.”
The leaders we spoke with all acknowledge that entrepreneurship requires sacrifice, resilience, and continuous learning. But with the benefit of hindsight, they’d all tell emerging business leaders the same thing: don’t wait to learn these lessons the hard way. Start with a clear vision, build strong foundations, invest in people, and remember that business success is inseparable from personal well-being.
The journey to the corner office is a marathon, not a sprint. And the CEOs who got there fastest were often the ones who understood that early on.
