I’ll be honest about something I wasn’t always willing to admit: there was a period in my career when I thought I had figured it out. I had built something real. The business was growing. The deals were getting done. And somewhere in that momentum, I quietly started believing that the instincts and hustle that got me here would be enough to take me wherever I was going next.
That belief almost cost me everything.
Not in a dramatic, single-moment way; businesses rarely collapse from a single mistake. It was more gradual than that. Decisions that should have taken a week stretched into months because I was too proud to ask for an outside perspective. Opportunities I didn’t fully understand sat on my desk while I pretended to evaluate them, when really, I was just hoping the discomfort of not knowing would resolve itself. And the problems I knew needed addressing got quietly moved to tomorrow’s list, because today I was too busy performing, even if I didn’t actually feel like it.
What changed things wasn’t a crisis, although a few smaller ones caught my attention. What truly made a difference was being honest enough to finally ask for help and discovering what happens when you build a genuine network of mentors and coaches around you. It is one of the most important things I have ever done in business, and I believe it saved the company.
The Myth of the Self-Made Entrepreneur
We admire the self-made story in entrepreneurship. The founder who figured it out on their own, trusted their gut when everyone else said no, and built something from nothing through sheer willpower. That narrative is compelling, and it’s also dangerously incomplete.
I started my first restaurant at age 20. By the time I was building a portfolio of franchise locations and moving into real estate development, I had a decade of hard-won operating experience. However, experience in one area doesn’t automatically transfer to another. The instincts I developed running restaurants didn’t fully prepare me for the capital structures of commercial real estate. The discipline I built managing operations didn’t seamlessly translate into navigating investor relationships and development timelines.
Each time I entered new territory, and in this business, you’re always venturing into unfamiliar ground, I operated with partial information and incomplete instincts. The honest truth is that no one builds something significant entirely on their own. The self-made myth simply overlooks the mentors, advisors, coaches, and peers who were there for the conversations that mattered most.
What a Real Mentor Actually Does
Before I truly understood mentorship, I saw it as a validation exercise, you find someone successful, share what you’re working on, and they tell you you’re on the right path. That kind of mentorship is almost useless.
Real mentorship can be challenging. The best mentor I’ve had in business listened to my plan for about ten minutes before clearly telling me exactly where my thinking was flawed, without softening it. He wasn’t discouraging; he believed in the opportunity but was direct about the gaps between my current position and where I needed to be. That conversation prevented me from making a major mistake and likely saved me six months of wasted effort.
A true mentor does more than just echo your ideas with praise. They offer a perspective you’re genuinely missing. They’ve made the mistakes you’re about to make, or they’ve watched others do so, and they can see the patterns you haven’t noticed yet. They ask the questions you’re avoiding. They challenge the assumptions you’ve accepted as final. And they do all of this because they don’t have a stake in making you feel good, only in whether you succeed.
That kind of relationship is uncommon, and it’s worth deliberately investing in it. It doesn’t always appear as a formal mentorship. Sometimes it’s a senior peer who’s willing to be brutally honest. Sometimes it’s a board member or advisor who takes the role seriously. Whatever form it takes, the willingness to be challenged is what makes it valuable.
The Case for Coaches — Plural
One of the changes I’ve made over the years is shifting from viewing mentorship as a single relationship to creating what I call a coaching ecosystem. Different challenges call for different perspectives, and no single mentor, no matter how experienced, can address every aspect of running a growing business.
I have people in my corner who understand real estate development at a level I’m still working toward. I have others who push me on leadership and organizational dynamics, the people side of building a company, which is often harder than the deal side. I also have peers in the Young Presidents Organization who are navigating the same stage of growth I am, which provides a different kind of coaching: one that comes from real-time shared experience rather than just accumulated wisdom.
Each of these relationships serves a specific purpose. The real estate advisors help me understand deals more clearly. The leadership coaches help me see myself more clearly. The peer network reminds me that the challenges I face aren’t unique; others have also overcome similar issues.
Together, they create something that no single relationship could: a system of perspectives that helps me see my blind spots more clearly and improves my decision-making.
What I Wish I’d Done Sooner
If I could go back and give my younger self one piece of business advice, it wouldn’t be about a specific deal or strategy. It would be this: build your coaching network before you think you need it.
The natural tendency is to seek an outside perspective when things are going wrong. When you’re in crisis, when a deal is falling apart, or when you’re unsure what to do next, that’s when most entrepreneurs finally pick up the phone. But by then, you’re already behind. The decisions that caused the crisis were made weeks or months earlier, often during moments when everything still seemed fine.
The mentors and coaches who provide the most value are those who know you well enough to recognize issues before they turn into crises. Building this level of relationship takes time. It demands consistent engagement, honest conversations, and a willingness to be seen, not just as the successful version of yourself, but as the full range of what you’re working through.
The entrepreneurs I respect most, those who have built something durable over multiple cycles, are almost always people who invest seriously in these relationships. Not as a networking exercise, but as a sincere recognition that their own perspective, no matter how sharp, has limits.
The Return on Humility
There’s a practical benefit to all of this that isn’t discussed enough. Mentorship and coaching aren’t just emotionally supportive; they also have economic value. The decisions I’ve made differently because of outside perspectives have, in total, been more valuable to this business than any single deal I’ve closed.
The mistakes I’ve avoided alone justify the investment many times over. Additionally, the quality of the opportunities I’ve been able to evaluate has improved as my network has grown deeper. The best deals in this industry come through relationships, and relationships strengthen when you engage with others seriously and generously over time.
Surrounding yourself with coaches isn’t a sign that you can’t figure things out on your own. It’s a sign that you’re committed enough to the outcome to leverage every advantage available. That shift in perspective, from viewing mentorship as a crutch to seeing it as a competitive edge, is one of the most important changes I’ve made. I’m a better operator, a better leader, and honestly, a better person because of it.
If you’re handling everything on your own right now, I suggest you honestly ask yourself a question. Is that really working? From my experience, the answer is always no in the end. https://lrecompanies.com/news-blog/