Building meaningful strategic relationships is a powerful way to accelerate success, no matter your age.
At the annual Better Wealth Mastermind in Denver, Jack Wendt shared his approach to building meaningful relationships, overcoming challenges, and how anyone—even introverts—can begin making valuable connections.
How Jack Wendt Became the Strategic Relationship Guy for Caleb Guilliams
Building strong relationships is about more than just knowing people—it’s about asking the right questions and being willing to learn. Jack Wendt’s story shows that sometimes, the best opportunities come when you take a chance and reach out to the right people.
Jack didn’t know Caleb Guilliams before he decided to work with him. He was just drawn to Caleb’s ability to connect with others and his smart way of thinking. Jack says, “I always say it’s asking the right people, the right questions. That’s a lot of the hardship in life—just figuring out who to ask and what to ask.” Jack saw Caleb as someone he could learn from and wanted to be part of his world.
After Jack graduated high school, he joined the Army National Guard to train in aviation intelligence. He worked hard, finished his training, and then did something bold—he flew to Nashville just 12 days later to meet Caleb.
“I had no job offered to me,” Jack says. “I just wanted to learn and help. I wanted to figure out what I could do to be a part of what Caleb was building.”
Jack didn’t expect to get a job right away, but his approach worked. Caleb was impressed with Jack’s drive, and they made a new job just for him at BetterWealth—Strategic Partnerships Manager. This role is all about building relationships and creating partnerships, and it didn’t even exist until Jack took the first step.
Jack’s story proves that sometimes, it’s not about waiting for opportunities to come to you—it’s about creating your own path by asking questions, being humble, and learning from others.
How to Overcome the Fear of Approaching High-Value People
When you’re trying to build relationships with high-profile individuals, it’s easy to feel intimidated. Jack Wendt, at 19, didn’t let that stop him from reaching out to Caleb Guilliams. So, how did he overcome the fear of rejection?
Jack explains, “We live in a world where everyone is a consumer. You scroll through TikTok, and there’s no judgment, no risk of rejection. But if you want to succeed, you can’t be afraid of rejection.”
Jack points to a unique example from Salt Lake City, where some of the best salespeople are made. “They go on a mission for two years and face rejection every day. They get over the fear of rejection because it’s constant.”
Jack’s advice: if you’re afraid of putting yourself out there, remember the worst that could happen is simply hearing ‘no.’ It’s all part of the process.
Jack also offers a simple solution: “Put yourself out there and see what happens.” Overcoming self-doubt and putting yourself in uncomfortable situations is key to building relationships. It’s about being brave, even when you’re uncertain.
Building Strategic Relationships vs. Selling
Jack Wendt sees building relationships as a better way to generate business than traditional selling. He believes that word-of-mouth and personal connections are the key to scaling any business.
“One of the best ways to scale sales is through personal connections,” Jack explains. “When you have someone who can vouch for you, that’s where strategic partnerships come in.”
Jack highlights an interesting example: selling life insurance to people who enjoy fly fishing. It might sound odd, but it’s a smart strategy. “You wouldn’t think that a 19-year-old working for a life insurance company would collaborate with a fly fishing YouTube channel, but there’s real value in it.”
Jack’s story shows how creative partnerships work. At 13, he started flipping watches for profit after helping his grandpa find a deal on a $4,000 watch. “I saved my grandpa $500, and I got $250 for my work. As a 13-year-old, that was amazing,” Jack remembers. Later, during quarantine, he took it further, buying and selling watches as a side business. His profits grew, and he learned to scale his success using what he calls “parlaying” money, reinvesting profits to keep the business growing.
Now, Jack is applying these relationship-building principles in his newest agency, High Rise Influence—which focuses on helping his clients become the leaders in their industries.
Jack shows how personal interests, like his love for watches, can open doors to high-quality connections. “I can talk to someone about the watch they’re wearing, and it breaks them out of autopilot. It sparks a real conversation.”
Jack’s approach emphasizes how building genuine relationships based on shared interests and knowledge can be a powerful tool for business growth.
Jack Wendt’s Advice for Young Adults Who Haven’t Figured It Out Yet
For many young adults, the pressure to know what they want to do in life can be overwhelming. Jack Wendt, however, didn’t figure it out until halfway through his senior year of high school. “I had no clue what I wanted to do. Is it college? Do I join the military? Do I start working and figure it out as I go?” Jack remembers.
He applied to colleges and got accepted to a few he thought were interesting. But, as he thought about it more, the idea of going into debt for a degree that might not guarantee success didn’t sit right with him. “There are so many people going to college and ending up with six figures in debt, but not that many people actually succeed,” he says.
Jack didn’t rule out college altogether. He might still get a degree later, possibly online, while working full-time. But for now, he knew he needed options. He didn’t want to lock himself into a single path too early. He thought about what his grandfather had done—becoming an air traffic controller while working in real estate on the side. It was a successful path, but Jack wasn’t sure if it was for him.
After considering different options, Jack chose the Army National Guard. He had always wanted to serve, and joining was also a way to honour his family. “My dad regrets not joining the military, and I wanted to put my last name back on an Army uniform. It’s one of the proudest moments of my life,” Jack says.
His advice to others in the same position: You don’t have to follow the traditional path. College is not the only way to find success. “You don’t have to go to college and take on hundreds of thousands of dollars in debt just to figure out what you want to do,” Jack explains. “There are people with $200,000 degrees they never use. Imagine buying a $200,000 car, parking it in a garage, and never using it. That’s what people do with their education.”
For Jack, the message is clear: It’s okay not to have it all figured out. Keep your options open, and don’t feel pressured to follow a path that isn’t right for you.
The Power of Authenticity and Following Through
Speaking in front of an audience can be intimidating, but for Jack Wendt, it was an opportunity to demonstrate the power of humility, authenticity, and following through. During a presentation with Dennis Yu, Jack had the chance to experience firsthand how easy AI can be to use in business. “I was a little nervous because I had no idea what Dennis was going to talk about. He told me I’d find out during the presentation,” Jack recalls.
In front of a live audience of about 200 people, Jack was able to use AI tools to review someone’s website and content without prior training or preparation. “I didn’t touch the laptop once. Dennis did all the technical work; I just talked,” Jack says. This experience showed the power of being open to learning and trying new things, even under pressure.
Dennis Yu, who has experience speaking in front of large audiences, admired Jack’s ability to connect with the crowd. “You can be charismatic and intelligent like Jack, but what really stands out is his willingness to take action and go for it,” Dennis explains. “People can sense your vibe. When you connect with others—whether through something as simple as a shared interest like watches—it shows that you share the same values.”
The key to building high-value relationships, according to Jack, is simple: asking the right people the right questions, being humble, and being authentic. “It’s about doing what you say you’re going to do,” Jack emphasizes. “A lot of people can’t commit on the back end. If you don’t have your word, what do you have? It’s the only thing you’ve got.”
Key Takeaways
- Building Strategic Relationships: Jack emphasizes the importance of asking the right people the right questions, maintaining humility, and focusing on personal connections to build meaningful relationships.
- Overcoming Fear of Rejection: Overcoming fear is key to success, and Jack draws on the experience of missionaries in Utah to highlight the value of rejection as a learning tool.
- Strategic Relationships vs. Selling: Jack explains that strategic partnerships, based on genuine connections, are more effective than traditional selling—citing his experience with niche markets like fly fishing and his passion for watches.
- Advice for Young Adults: Jack shares his journey of figuring out his career path, advising young adults not to follow the beaten path and stressing the importance of keeping options open and gaining real-world experience.
- The Power of Authenticity: Jack highlights the importance of authenticity, commitment, and following through on promises to build trust and long-lasting relationships.
