Post-Exit Entrepreneur And Market Disruptor Kyle Wilson Shares How To Hire Right And Win Big

Jeffrey Feldberg
6 min readAug 22, 2024

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One of our sayings at Deep Wealth is “Show us your team and we’ll show you your future.” In the Deep Wealth 9-step Roadmap for success we look to Step 2 X-Factors which has your team as a foundational X-Factor. For most entrepreneurs it’s a hit or miss when it comes to hiring.

The host of The Deep Wealth Podcast and post-exit entrepreneur Jeffrey Feldberg speaks with a fellow post-exit entrepreneur Kyle Wilson on how to hire right. In today’s world, business owners and entrepreneurs often face the challenge of finding the right talent to grow their companies. Kyle Wilson, the founder of ThriveModal and Yellow Diamond Logistics, has a story that can inspire anyone looking to find success, even in tough times.

Kyle Wilson started his journey in Annapolis, Maryland. He then moved to Atlanta, Georgia, in 2005 to attend Emory University. He graduated with a degree in economics in 2009. But like many during the recession, Kyle faced the harsh reality that fancy jobs were hard to come by. “All of those fancy jobs in economics that I thought I was going to be getting were just not there,” Wilson admitted. So, he took the first job he could get as a freight broker.

Kyle worked for a company called Echo Global Logistics. His job was to be the middleman between manufacturers, distributors, and truckers. Even though it was a sales job, Kyle excelled and was the sales rep of the quarter multiple times. Later, he moved to a smaller logistics company, Transdynamics. Here, he learned the art of building relationships. “I really appreciated that experience, right? So I got the dichotomy of kind of working, And my younger part of my career with the bigger companies. And then when I moved to Transdynamics, all of the sales reps were 50 years older. So I really got a good touch of how you wine and dine customers and how really grow a relationship.”

The Birth of Yellow Diamond Logistics

By the time Kyle turned 30, he had eight years of experience in logistics. Realizing that to earn even more, he needed to own his company, Kyle started Yellow Diamond Logistics. His journey wasn’t easy. He needed to hire his first employee but didn’t have enough money to pay someone in America. So, he had an idea: hire virtual assistants from the Philippines. “I just couldn’t do it, right?” Wilson explained. “I’d worked so hard to earn that money that I was very protective over it.”

This idea led him to hire his first virtual assistant, JP. Kyle trained JP by live broadcasting his daily tasks, and soon JP became a carbon copy of Kyle. This strategy helped Kyle grow Yellow Diamond Logistics to over $40 million a year in revenue. “Long story short, I looked up four years later, I had over a hundred people in the Philippines working at Yellow Diamond.”

The Creation of ThriveModal

Kyle’s second business, ThriveModal, specializes in staffing U.S. companies with Filipino talent. He proudly stated, “ThriveModal has grown to about a 12 million dollar a year run rate in just a year and a half.” His vision is to grow the company to about a thousand people, providing more opportunities for skilled professionals in the Philippines.

ThriveModal’s success is built on Kyle’s deep understanding of the U.S. job market and the Filipino talent pool. He highlighted the importance of having a trusted recruitment team in Manila to ensure the best matches. Kyle said, “Having the local element of trusted individuals with great recruitment experience” was crucial to their success.

Kyle’s success with Filipinos led him to start ThriveModal, a U.S.-based staffing firm for Filipino talent. The firm’s mission is to connect businesses with skilled professionals from the Philippines. This idea came to fruition when Kyle was asked to find an electrical engineer for a company. Despite initial doubts, Kyle found Daryl Latrada, who was a perfect fit. This success transformed Kyle’s vision. “I kind of chuckled and said, hey, you may have been missing the point of my story there, but nonetheless, let me go out and take a look.”

Kyle shared the process he uses with his clients. “When we get back that hiring requisition form, really my customer’s job stops.” His team then takes about three weeks to interview candidates and presents the top choices to the clients. This meticulous process ensures that clients find the best fit for their needs without upfront fees or long-term commitments.

Kyle believes that outsourcing can be beneficial for U.S. businesses, despite some people thinking it takes jobs away from Americans. He says, “When you look at the logistics company I started, even 10 years ago, for 50, 000 a year, to get somebody to come in and track and trace trucks, literally just call them, ask them where they are, and write them down in the system…” He believes that these positions are destined to leave America, and by outsourcing, companies can allocate funds to hire better talent and grow their business.

Tips for Entrepreneurs

Kyle offered valuable advice for entrepreneurs, stressing the importance of having an operating partner. He explained, “Having an excellent operating partner has been life-changing. It’s worth it and a mistake that I made at Yellow Diamond was very early in that business.” His experience with an operating partner at ThriveModal showed him the value of having someone who can handle operations meticulously.

Kyle’s journey offers several valuable lessons for entrepreneurs:

  1. Don’t be Afraid to Take Risks: Kyle started his own company to escape a difficult work environment. “And so, to answer your question, was it out of spite? No, I don’t think it was out of spite, but, it was really out of being treated, in a way that I thought the person didn’t value me.”
  2. Document Processes Early: Initially, Kyle didn’t document processes, which made growth hard. “And I wasn’t documenting processes, I wasn’t creating SOPs.”
  3. Find the Right Partner: Kyle’s partnership with Oliver Ung helped ThriveModal grow smoothly. “Oliver Ung… spent the last 15 years in private equity and he came to me after hearing the Yellow Diamond story.”
  4. Outsource Wisely: Hiring virtual assistants who complement your team can be a game-changer. “We recruited the best recruiters in Manila for the finance industry, for the healthcare industry, for logistics.”

Final Thoughts

Kyle Wilson’s story is a testament to the power of hard work and smart decision-making. Despite starting in challenging times, he grew his companies by finding innovative solutions and believing in the talent pool in the Philippines. His advice to entrepreneurs: embrace the journey, learn from your experiences, and leverage global talent to drive your business forward. As Kyle puts it, “At the end of the day, I believe that those jobs are destined to leave America.”

Kyle Wilson’s journey highlights the potential of global talent, especially from the Philippines. His innovative approach to using virtual assistants and skilled professionals has transformed his businesses and provided valuable lessons for other entrepreneurs. As Kyle puts it, “Let me show you before you pay me anything. Let me let you speak to these people individually and you make your own decision.” His commitment to proving his methods based on merit and helping others succeed is truly inspiring.

So, remember, whether you’re just starting or looking to take your business to the next level, there’s always a way to thrive and prosper, just like Kyle Wilson. If you want to learn more or are interested in finding top-notch talent, you can reach Kyle at ThriveModal. He’s passionate about helping others succeed, and he’s just an email away.

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Jeffrey Feldberg

Helping you capture the best deal on your exit through the Deep Wealth 9-step roadmap. Leverage the same strategies I created for my 9-figure liquidity event.