When Jaime Jay, founder and CEO of Bottleneck Distant Assistants, reflects on his journey into entrepreneurship, one thing is clear: his success is driven by an unwavering desire to challenge the status quo. After more than a decade in corporate America and with roots as a paratrooper in the U.S. Army, Jaime ventured into the world of virtual assistants. His goal was not to be better than the competition but to be radically different. Jaime shares his insights, struggles, and the principles that have shaped his company, now the world’s first dedicated distant assistant service.

A Desire to Break Free

For many, entrepreneurship is about independence, creativity, and pursuing a passion, and Jaime is no different. However, his transition from corporate life to running his own business wasn’t immediate. It took 12 years in corporate America to make the leap, and the decision was catalyzed by his frustration with the bureaucracy he encountered in large organizations.

“I like doing things a certain way,” Jaime recalls. “In corporate America, there’s so much red tape that it takes forever to get new ideas introduced.” One particular event while working in radio served as a turning point. Jaime had successfully organized a heartwarming event to rebuild a mother’s car as part of a contest. Despite the success, the tedious process of approvals, legalities, and corporate delays led Jaime to realize that this was not the environment for him. “That was enough for me,” he says. “I wanted to go out on my own and start something new where I could move quickly.”

Ironically, the radio company he left became his first client when he ventured out on his own, a testament to his skills and the relationships he’d built.

The Birth of Bottleneck Distant Assistants

Jaime founded Bottleneck Distant Assistants with the vision of helping businesses manage their workload more effectively through virtual assistants. But this wasn’t just another VA company. Instead of competing to be the best, Jaime sought to create something different. “We leveraged the power of category design,” Jaime explains. “We weren’t trying to be better than anyone; we just wanted to be different.”

He credits much of the company’s early success to the insights from Christopher Lockhead, one of the authors of Play Bigger, a book that focuses on category creation. It was with Lockhead’s guidance that Bottleneck created the “Distant Assistant” category, carving out a unique space in the virtual assistant industry.

“We launched the Distant Assistant category at the end of 2021, and we’ve spent the last couple of years educating people on the differences,” Jaime says.

Systems and Processes: The Secret Sauce

Jaime’s military background as a paratrooper instilled in him a love for systems and processes—something he has carried into Bottleneck Distant Assistants. His approach is all about documentation, precision, and repeatability. This is also the central theme of his book, Quit Repeating Yourself, which outlines how businesses can leverage systems and processes to grow efficiently.

“One of the biggest differences between our assistants and traditional virtual assistants is how we build systems and processes for our clients,” Jaime explains. “We teach our Distant Assistants to document everything, which helps ensure everyone is on the same page about roles and responsibilities.”

This systemization has had a tangible impact on the business. While the average virtual assistant stays with a client for just five months, Jaime boasts that his Distant Assistants stay for 39 months on average. “I think that’s directly correlated to the systems and processes we have in place,” Jaime says.

A Relentless Focus on Small Business

Despite his success, Jaime remains committed to working with small and medium-sized businesses. “We don’t work with large businesses,” Jaime says candidly. “Even with medium-sized companies, things can get crazy with all the approvals and red tape.” His passion lies in helping smaller companies streamline their operations, freeing up time for owners to focus on growth and innovation.

One of the core philosophies of Bottleneck is the absence of contracts. “We don’t believe in locking clients into long-term agreements,” Jaime says. “If someone wants to stop using our services, they can simply let us know. Everything is month-to-month.”

This approach reflects Jaime’s larger belief in building trust with clients and delivering value without the burden of bureaucracy.

The Challenges of Scaling

Like any entrepreneur, Jaime has faced his share of challenges. One of the biggest hurdles for Bottleneck has been managing human capital effectively while scaling the business. “When you’re dealing with human beings, there’s a lot of weight on your shoulders,” he explains.

Many clients come to Bottleneck in a state of overwhelm, needing an assistant urgently. However, Jaime is adamant about maintaining a thorough vetting process, which can take up to four weeks. “If we rush the process, the relationship doesn’t work out,” Jaime notes. “We have to be diligent.”

Scaling up to meet demand while maintaining quality is a challenge Jaime is actively addressing. Over the next six months, he plans to expand into new countries and establish partnerships that will enable faster hiring without compromising on quality. “We’ve documented the entire process, and now it’s about finding the right partners to help us grow,” he says.

Vulnerability and Networking: Keys to Growth

One of the most surprising lessons Jaime has learned is the importance of vulnerability. “It’s hard for me to be vulnerable,” he admits. “But being open about what I don’t know has led to some of the best growth opportunities.”

Jaime recalls a time when he was invited to speak to a team and felt embarrassed for not knowing the answers to some key questions. “I felt like I had let them down, but it taught me the importance of being honest about my limitations,” he says.

This vulnerability has also helped Jaime form valuable connections through networking groups. “I don’t like selling, but I love sharing what we do,” Jaime says. “Joining networking organizations and being open about our strengths and weaknesses has brought us incredible clients.”

Looking Ahead

As Jaime looks to the future, his goals for the next six to twelve months are clear: continue scaling Bottleneck Distant Assistants while maintaining the high standards that have set his company apart. “We need to grow, but we can’t sacrifice quality,” he says. “That’s why we’ve spent so much time documenting our processes and building partnerships.”

With a new process launching soon, Jaime is optimistic about the future. “We’re ready to take on the next phase of growth,” he says.

Final Thoughts

Jaime Jay’s journey from paratrooper to entrepreneur is a story of perseverance, innovation, and a commitment to doing things differently. His passion for systems and processes, combined with his dedication to helping small businesses, has made Bottleneck Distant Assistants a game-changer in the virtual assistant space.

For aspiring entrepreneurs, Jaime’s advice is simple but powerful: “Document everything, move fast, and don’t be afraid to break things along the way. But most importantly, be open to learning from your mistakes.”

As Bottleneck continues to grow, there’s no doubt that Jaime Jay will keep pushing the boundaries of what’s possible in the world of distant assistants—one documented process at a time.

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