FreightCaviar Podcast: Will Jenkins: From Cutco to Co-Founding MoLo Solutions

From the bustling and windy Chicago streets to the helm of a logistics empire: This is the story of Will Jenkins, co-founder of MoLo Solutions and now the founder and CEO of a new venture aptly called Journey.

More than a corporate climb, Will's story is of transformation, from selling knives at 18 to leading a major player in the logistics industry. In this Freight Caviar Podcast episode, Will opens up about his entrepreneurial spirit, passion for sales, and the pivotal moments that forged his success in the business world.

Origins: Grit and Determination

Will Jenkins' story begins in Maywood, Illinois, a neighborhood on the west side of Chicago. Reflecting on his roots, he shares, “I’m from Maywood... it’s got some rough parts. And I think that gave me a lot of character.” Raised in an environment that presented its own set of challenges, Will credits his resilience and adaptability to his upbringing. His parents, both from Chicago's west side neighborhoods, were pivotal in shaping his outlook.

Will's competitive spirit, a key driver in his sales and entrepreneurial career, was nurtured early on through sports. He played football at Illinois Wesleyan, acknowledging, “I wasn’t going to the NFL... but good enough to play in college.” The experience instilled in him a belief that success comes from hard work rather than just natural talent.

“I’m not the biggest, I’m not the fastest, but I will outwork you."

Early Sales Adventure with Cutco Knives

Fresh out of high school and before heading to football camp, Will took on a sales job that laid the foundation for his career.

With no prior sales experience, Will dove into the world of direct selling. He leveraged his high school directory, reaching out to parents of classmates, and navigated through rejections and hang-ups.

Despite the initial setbacks, his tenacity paid off. In just ten days, he sold $10,000 worth of Cutco products, earning $2,000 on commission.

It wasn't just about the numbers. A lesson from his manager at Cutco, Danny Lewis, taught him the importance of maintaining a positive perspective with an easy task: "He taught me something... just take a sticky note, put a smiley face on it, put on your steering wheel and like go do your appointments," Will shares. He met his sales target and sparked his passion for sales.

"At 18 in June, I was like, sales is for me. This is it."

Reading the Manual

In those early days, long before co-founding MoLo Solutions, Will Jenkins embraced a fundamental approach to sales – he simply read the manual. While selling knives, this straightforward strategy laid the groundwork for his future successes.

Will recalls, “I literally read the manual...you read this and sell to the right target market.” It wasn’t about reinventing the wheel but understanding and applying proven techniques.

Will’s method was as practical as it was effective. He targeted a specific demographic – married homeowners over 30 – understanding that this group was most likely to purchase his products. This early experience in identifying and focusing on a niche market worked. Knowing your product and your customer is the first step.

As he progressed, Will's tactics evolved beyond the manual. He learned to handle objections, build rapport, and understand customer needs on a deeper level.

"Once you get better, you start to handle objections differently... How do I build rapport with them?”

Success often starts with mastering the basics and then adapting and growing your skills to meet the changing landscape.

Early Sales Management Experience

Shortly thereafter, Will was managing a Cutco office in Chicago.

"I opened up the office in May of 2010. From May to August, we did $110,000 in business. I had three receptionists that worked for me, 80 sales reps, and I wanted to quit every single day."

Here, he experienced what he calls his first real failure as an entrepreneur. Managing a Cutco office, he faced the daunting reality of business – the pressure to succeed or shut down. "I remember being in tears in my office... Either we figure out how to make this happen, or I close the doors," he recalls vividly.

"That was probably one of the more pivotal moments for me as a young, aspiring entrepreneur. Because that pressure really helps you understand how to go make things happen."

This early management role taught him the critical impact of talent on business success, preparing him for the challenges ahead.

Will's early experience in cold sales, working on 100% commission, instilled in him a fundamental sales principle: the necessity to close and progress through the sales cycle efficiently. Observing his peers who had moved on to own businesses or become top sales executives, he understood the value of perseverance and performance. "Seeing those people be successful gave me great perspective," he notes, acknowledging how these experiences shaped his future aspirations and approach to business challenges.

From B2C Sales to the Transportation Sector

Moving to Kimberly Clark at 22 marked a significant shift from quick, transactional sales to the nuanced world of B2B dealings. "I was used to quick, fast transactional sales," Will recalls, highlighting the contrast with his new role, which required building long-term rapport and persistent, professional engagement for large-scale deals.

Feeling out of his depth initially, Will's journey took another turn when he joined Coyote Logistics in 2014. "I had no experience at all," he admits, discussing his move into the transportation sector. Here, he focused on carrier sales, learning from mentors like Drew Herpick. Will's approach was to seek advice and closely observe successful practices. "What do I need to do to be where I would have been if I would have started here out of college?" he asked his mentor, showcasing his eagerness to learn and catch up.

Carrier Sales Tactics for Success

In carrier sales, Will emphasizes several key tactics for success:

Develop Long-Term Relationships: Focus on building lasting partnerships with carriers to ensure consistent capacity.
Balance Transactional and Strategic Approaches: While same-day freight is important, nurturing year-round relationships is crucial.
Understand Market Volatility: Successful reps make money regardless of market conditions by having reliable carrier relationships.
Leverage Available Resources: Use call-ins effectively but don't rely solely on them for business.
Prioritize Consistent Capacity and Rates: Forge partnerships with carriers who offer stability in rates and capacity.

Taking a Leap: Founding MoLo Solutions

In January 2017, after a few years in the logistics industry, Will took a significant step by joining Transport America as Director of Business Development. Despite initial excitement, he quickly realized it wasn’t the right fit. "I saw a lot of differences... I don’t see myself building here," he reflects. This realization, coupled with a soul-searching backpacking trip to Europe, was the catalyst for his next big venture.

Returning with fresh inspiration from "Shoe Dog" by Phil Knight, Will reconnected with Andrew Silver, his former manager at Coyote, and Stefan Mathis, another future co-founder. They began envisioning an idea for a new brokerage.

During the process, they hit a creative wall – choosing the right name for the company. Initially, they considered several names, including 'Simba Transportation,' but soon realized the pitfalls, particularly in terms of search engine optimization (SEO) and potential confusion with Disney characters.

The team went to Au Cheval in the West Loop, where they faced a six-hour wait. This unexpected downtime turned into a brainstorming session. During lunch, Andrew mentioned an app called ToMo, standing for 'Top Modern.' This sparked a thought in Will, leading him to propose 'MoLo' as a potential name, an abbreviation for 'Modern Logistics.' It was concise and effectively communicated the essence of their company – a modern approach to logistics. By July 2017, they were ready to launch.

Early Challenges at MoLo

In the early days of MoLo Solutions, one of the most pressing issues was establishing credibility and trust with carriers, a vital aspect of their business model.

For an in-depth look at MoLo Solutions' explosive growth to over $600 million in revenue with just 500 shippers, its acquisition by ArcBest, and more, catch the full episode below.