The Power of Mentorship: A Conversation with Zachary Regan on Building Genuine Relationships

During a recent conversation with Zachary Regan on his podcast, we explored a topic close to both our hearts: the power of mentorship for young adults. Zac is the owner of Why Real House Stories, a marketing and sales agency that helps entrepreneurs thrive online. He has a great understanding of social media marketing and how to design frameworks for being seen online, particularly helping people develop effective sales strategies.

During our conversation, I shared some of the key principles that have guided me throughout my journey. Here’s a glimpse into what we discussed.

From Engineer to Influencer

My journey began with math competitions and later evolved into a role as an engineer at Yahoo, where I helped build the platform’s analytics 20 years ago. This gave me an insider’s perspective on how search engines work—and how to protect them from being gamed. Ironically, this foundation led me into digital marketing.

As I started speaking about what I knew, my expertise naturally attracted an audience. I didn’t set out to be an influencer, but sharing my knowledge openly earned me a million followers and countless opportunities to speak on stages worldwide.

To me, personal branding isn’t about what you say about yourself; it’s about what others say about you. I’ve built my brand by focusing on paying it forward. Creating value for others—without expecting immediate returns—has opened countless doors in my life.

Unlocking Success Through Mentorship

When I started in business, I thought success was about making a lot of money first. I believed that after hitting milestones like my first million, I could focus on giving back. As a 20-year-old, I had a shallow view of success. But as I met truly successful people, I realized something profound—they were some of the nicest, most generous individuals.

One of my mentors, the CEO of American Airlines, opened doors I never imagined. He introduced me to leaders like the President of Goldman Sachs, former U.S. President George H.W. Bush, and CEOs of major corporations. I was just a young nobody, yet I found myself having lunch with people like the CEO of Allstate Insurance, Dick H. He stood out because of his kindness and willingness to help.

I’ll never forget the time I was in a car accident during finals. Dick didn’t have to, but he helped me. Even though I wasn’t an Allstate customer, he called the CEO of my insurance company and expedited my claim. The next day, it was resolved—a process that normally takes weeks. I asked him how he achieved such remarkable success. He said, “Contrary to what people think, nice guys don’t finish last. They win.”

He explained that as an entrepreneur, you need to attract talented people to work for you. To do that, you must care about them and build genuine relationships. Success, he said, is rooted in kindness, trust, and long-term connections.

This lesson became clearer over time. I’ve met incredible people like Munawar Abdullah, who sold his company for $300 million, and other top leaders who are all generous with their time. For example, during a trip to Dubai, I had dinner with Munawar and ended up missing my flight because our conversation was so valuable. He lives life intentionally—one or two meaningful meetings a day—and prioritizes quality over quantity. Despite his relaxed schedule, he’s made more money recently than ever, purely through the relationships he’s built.

This approach isn’t limited to those with “infinite money.” It works for anyone who focuses on the right people and opportunities. For instance, I was recently helping my friend Elliot Drake, a young entrepreneur who had lost his father to addiction, figure out his next steps. He wanted to enter the rehab space to make an impact. The very next day, I got a message from someone looking for help with marketing their rehab clinics. It wasn’t a coincidence—it was alignment.

Success isn’t about grinding 18 hours a day. It’s about being intentional with your time, building trust, and focusing on quality over quantity. When you live this way, the results speak for themselves.

The Power of Genuine Connections

I believe you’re the average of the five people you spend the most time with.

Whether it’s staying up late talking to a friend in Dubai or mentoring a young entrepreneur, I prioritize building meaningful connections. Every major client I’ve had—Nike, Starbucks, Golden State Warriors—came to me because of relationships, not cold pitches or hard negotiations.

Imagine if young adults, influenced by the latest trends on Instagram, where people fake success and pretend to have it all together, could hear your message. Think about how much that would change lives. They’d see the reality of those who are genuinely successful. It’s about sharing your message. When you hold back, you’re almost doing a disservice by not putting yourself out there. Personal branding plays a big role in this.

Often I fly to Orange County to meet my friend Matthew Janusek, arguably one of the most influential people in the fitness industry. He’s the CEO of Escape Fitness and has interviewed everyone—Mr. Olympias, gold medalists, and CEOs of top fitness brands like 24-Hour Fitness. He’s a real industry leader and has been my client for about eight years.

In the beginning, our relationship was transactional—typical agency stuff. I had to justify budgets to his board, recommend strategies for Google Ads, optimize the website, and get approvals. Over time, our relationship evolved into something more meaningful. Now, when we meet, there’s no agenda. We spend holidays together, and I even teach his kids math. It feels more like hanging out with a friend than working with a client.

That’s how all the best client relationships feel. They’re built on trust and friendship, not just transactions. And I’ve had bad clients too—ones where it’s strictly business, and it’s exhausting. Good clients don’t feel like work; they feel like relationships. The retainers show up automatically, and you’re happy to collaborate because it’s more than just about money.

Unfortunately, many young professionals hustle solely for cash. They treat relationships transactionally like they’re selling themselves instead of building connections. If you act like that, people will perceive you that way. It’s a cycle, and it’s not sustainable.

Some might argue, “It’s easy for you to say, Dennis. You’ve already made money, built credibility, and have a big team. You don’t understand what it’s like starting from nothing.” I hear that a lot. They feel like they have to hustle because they need clients to pay rent at the end of the month. But is that approach truly working for them in the long run?

Building genuine relationships is key to long-term success, even when starting with cold calls. While financial strain can make it tempting to chase quick wins, sacrificing reputation and meaningful connections for short-term gains leads to high churn rates. Instead, focus on delivering value and creating real bonds, as these relationships open doors and lead to sustainable growth. Patience and consistency set apart those who thrive from those who merely get by.

Let me share a story. I spoke with someone who runs a marketing agency and asked them, “Do you have a client you absolutely love—one you’d want ten more of?” They immediately said, “Oh, definitely!“

So, I followed up, “Have you interviewed that client on your podcast?” They admitted, “No, I haven’t. I just haven’t had the time or even thought about it.“

That’s where most people miss out. When someone says they “don’t have the time,” it’s about priorities. If this client is a dream client—the kind I call a LIGHTHOUSE Client—then they’re not just valuable themselves. They’re the kind of client whose success can be replicated and respected by others in their industry.

I told them, “Imagine interviewing your LIGHTHOUSE Client—not as a testimonial but to elevate and celebrate them. Then, boost that content to others in their space. If they’re in real estate, for example, people in their network would see it and start associating you with excellence. That’s how you attract similar clients.”

I’ve done this myself. Take Tom Ferry, for instance. He’s a big name in real estate. He came to me and said, “Dennis, let’s do a masterclass.” So, we created step-by-step content on digital marketing—how to run Facebook ads, optimize websites, use AI, and so much more. We repurposed that into YouTube videos, blog posts, and social media content.

The results? Phenomenal. Real estate agents kept coming back for more, not because I was selling to them, but because the content was genuinely helpful. It built trust and positioned me as an expert without me ever having to pitch.

I turned to this agency owner and asked, “What’s stopping you from doing the same? Interview your best clients, highlight their expertise, and make it about them. When others in their industry see that, they’ll naturally want to work with you.”

This approach isn’t just about selling; it’s about building relationships, demonstrating value, and creating a magnet for the kind of clients you want most. It’s a strategy anyone can use—so, why not start today?

Simplify to Scale: The Key to Long-Term Growth

I used to think that I needed to wait until I had a perfect, solid case study before talking to clients. But the reality is, you don’t have to wait. It’s all about approaching them and talking about their business.

Ideally, yes, you want results. But here’s the thing — they don’t need to be massive, immediate results. I’ve had some crazy results that were more luck than skill, and I don’t like making promises or guarantees. Instead, I prefer to show typical results. Why? Because if you only highlight the incredible, outlier results, clients will expect that every time. That’s when problems happen. The best clients are hands-off. They don’t demand much.

It’s funny, though: the less clients pay, the more needy they are. The clients who spend over $10,000 per month? They treat us a lot better. It’s a paradox. Early on, we’d take on clients for fun at $1,000 a month, and those were the nightmares — constantly calling, always needy. But when you charge more, you get fewer of those headaches.

When it comes to marketing, I see all digital channels — whether it’s Google, Facebook, TikTok, or email — as tools. I don’t have a favorite. What I care about is using the tool that works best for the client in that situation. I’m not just a Facebook ads guy, even though that’s what people may label me. I’m a data guy. It doesn’t matter which platform or tactic we use; it’s about solving the problem. It’s like when a patient goes to the ER — they all need different treatments. Some need surgery, others need a cast. You have to know what works best.

Building my business? Honestly, I’m a terrible business builder. I’m not an operator, I’m a creator. I’ve always been that way. I don’t like the traditional business model. Mark Cuban says it’s always on, and I’m with him on that. There’s no start or stop. It’s a continuous grind.

Early on, I tried to learn everything myself — which taught me a lot but also led me to realize that most people in digital marketing are completely incompetent. I don’t say this to be harsh, it’s just the reality. When you start digging into things, you realize that most people don’t even know the basics. Sure, I’m not the best at everything, but I know the basics, and that’s what makes the difference.

But when I started, I didn’t have all the systems in place. I didn’t have audit checklists. I thought I could wing it. It wasn’t until later that I realized the importance of checklists. My first job at American Airlines taught me this. Airlines operate on checklists — check before takeoff, check before landing. It’s crucial. I didn’t realize how much of that structure was important until I hit 50, and now I find myself telling younger people to follow those same rules. It’s like a rite of passage.

I was a rebel once, too. I thought I could skip the process and use shortcuts. And guess what? It didn’t work. I had to learn the hard way. Some people still try to skip the steps, thinking there’s a magic shortcut to success. But just like losing weight, there’s no magic bullet. It’s hard work, consistency, and the right mindset.

Now, for anyone starting a business in the first couple of years — they try to do too much. They try to be everything to everyone. You can’t do that. You need to focus on one thing. Look at Chick-fil-A — they focus on chicken sandwiches and do it better than anyone else. If they tried to sell pizza, spaghetti, or hamburgers, they’d be a cafeteria, not a successful business.

Focus on one thing, get really good at it, and grow from there. Once you hit $10 million a year, then you can expand. But until then, focus on one core service. That’s the key to success.

Simplicity at scale is what you need. The more projects and clients you take on, the more custom things you’re doing, the more you’re tied up in every detail. That’s when you trap yourself in your own business. I know because I did it. I thought I could handle everything myself — but eventually, you have to step away, or your business won’t grow. It’s like being a chef at your own restaurant. Sure, I love Gordon Ramsay’s food, but he’s not in the kitchen cooking every dish. He’s built a system that delivers consistency, even without him in the kitchen.

When I first started in digital marketing, I did everything myself. I was the one doing the videos, the editing, the uploads. But now, I have a team. If you want to scale, you have to let go and build processes. I was talking to Jake Paul once about his rise on YouTube, and he said something that stuck with me: “Start creating your first video now.” Don’t wait for the perfect equipment, the perfect team, or the perfect situation. Just start.

That’s the mindset you need. Take action. Keep improving. And eventually, you’ll build something that works.

Zachary’s Funnel Strategies

Zac shared his unique approach to combining mentorship with practical business strategies. He emphasizes the importance of starting small and refining over time. He shared strategies for creating effective campaigns, which align closely with my relationship-focused approach. He emphasized structuring email workflows to target users based on their behavior. For example:

• If someone makes a purchase, they should enter a workflow tailored to buyers.
• If they view an offer but don’t buy, a different workflow should nurture their interest.

Zachary also recommended centralizing campaigns on platforms like Go High Level or ClickFunnels, which make it easy to integrate upsells and downsells. A clean, distraction-free sales page with a headline like “Join 325 Entrepreneurs Using the Dollar a Day Program” and a compelling Video Sales Letter (VSL) can drive conversions effectively.

For email marketing, he stressed warming up your sending domain and incorporating features like order bumps, down sells, and upsells. These strategies, combined with a focus on building trust, create funnels that deliver both short-term and long-term results.

One Piece of Advice

Learn to teach by example.

If you want people to buy your product, be a living example of that product. I often talk about the importance of running dollar-a-day ads, and I have countless examples from over 20 years of experience. Every day, I live and breathe this—I’m practicing what I preach.

Whatever you’re selling, ask yourself: Are you a customer of that thing? Do you live and breathe it? I created a tool that builds personal brand websites to help people rank better on Google and improve their SEO. And guess what? My own site uses that same tool. I’m not too good at it. If it’s good enough for me, I believe it’s good enough for your personal brand.

All of our clients use it, and many of my friends do too. I often give it to them for free because I’ve already invested so much into building it. Why not?

With over 800 speaking engagements worldwide and a strong social media presence, I’ve learned that success isn’t about self-promotion—it’s about creating value and building genuine relationships.

Your success begins with your relationships. Invest in people, simplify your processes, and practice what you preach. By doing so, you’ll build a brand and a business that lasts.