Taking Risks, Building Networks, and Embracing the Unknown with Len Morrissey

By: Carolyn Case, Talent Optimization Strategist

In a captivating episode of the Pain Points Podcast, Lauren Lewis from StaffBuffalo sat down with Len Morrissey, Managing Partner at Morrissey Metcalfe and Associates LLC and recent published author, to discuss his journey from the structured world of banking to the high-stakes world entrepreneurship and publishing his first book, Cursed Gift.

A Clash of Worlds: The Rigid Rules of Banking vs. The Thrill of Risk

Len Morrissey’s career began in banking, an industry known for its conservatism, rules, and obsession with minimizing risk. While banking is an excellent training ground - where you learn the mechanics of business success and failure - it was ultimately a mismatch for Len's temperament.

“I loved the work, but banking is rigid. It’s all about avoiding risk,” Len explained. “I’m not a process-oriented guy, and I thrive on taking risks and being curious, so it became clear that my instincts didn’t align with the industry.”

In banking, decisions are weighed heavily, risk is avoided, and creativity often takes a back seat. For someone like Len, whose natural inclination is to face challenges head-on and embrace uncertainty, the strictness of the banking world started to feel like golden handcuffs.

“There’s a reason why really smart people tend not to take risks,” Len noted. “They understand the consequences. But entrepreneurship requires the opposite mindset—you have to be willing to take calculated risks, even knowing that failure is possible.”

This leap of faith wasn’t just about changing careers - it was about changing his entire outlook. “I don’t want to be on my deathbed thinking that I should have tried something,” he said.

The Challenge of Letting Go

Len became CFO of Rapid, a sheet metal manufacturing company, before eventually stepping into the role of President. His biggest challenge as an entrepreneur? Learning to let go. “When you start a business, you have to do everything,” he explained. “But as you grow, you have to delegate, or you’ll crush your own company.”

As Rapid scaled, Len led the business through the complex process of restructuring and selling the company—a task he described as both the best and worst time of his life. Balancing the needs of anxious employees with the expectations of new management took a toll. “It was like running two companies at once,” he said, referring to the emotional rollercoaster of selling his life's work.

Rediscovering Purpose

After the sale, Len found himself at a crossroads. He briefly dabbled in starting a new venture, DraftPick.com, and then also committed to early retirement for a few years. It wasn’t long before he realized he was extremely bored and was ready for his next challenge. “Everyone around me was working, and my brain felt like it was wasting away,” he said. “I learn by teaching,” he explained. Len expressed how he needs to meet with people and share his ideas and what he’s learning, and all his friends were busy with full time jobs. “My wife didn’t want to hear about all my random hobbies!” he joked.

This led to two years of soul-searching, during which Len realized he needed something bigger to focus on. He co-founded Morrissey Metcalfe and Associates LLC, a firm that helps banks underwrite loans more efficiently, allowing small businesses to access capital faster. He found a new mission in helping others navigate the complex world of banking and finance, while also rediscovering his passion for learning.

Cursed Gift: The Risk-Taker Becomes a Storyteller

Just when you think Len’s risk-taking journey couldn’t get any more interesting, he takes another bold step—into the world of fiction writing. His novel, Cursed Gift, is a captivating exploration of karma and the consequences of the words we speak. The story follows two kinds of people: Glowers, who unknowingly influence the world around them through their emotions and words, and Sensors, who notice these changes.

The idea for Cursed Gift stemmed from Len’s fascination with karma and the unseen power we wield over our surroundings. “What if the things we say in anger or frustration actually came true?” he wondered. That spark ignited the creation of an entire world, one where characters have unique, karmic abilities they don’t even realize are affecting their lives - and the lives of others.

Writing Cursed Gift was, in itself, an entrepreneurial journey. “I spent six months just figuring out how to write a book,” Len laughed. “Then it took me a year to write it. But when I sent the manuscript to an editor, the feedback was so intense that I didn’t touch it for months.”

But Len’s entrepreneurial spirit kicked in again. Just as in business, where failure is an integral part of the process, writing required him to embrace criticism, accept help, and push through self-doubt. “Good writers have good editors,” he acknowledged. “And good entrepreneurs have strong teams.”

Despite the initial setbacks, Len couldn’t stay away from his characters or the story. “I love these characters. I think about them constantly,” he said. “Every day, I’m excited to see how they grow and change.”

“Cursed Gift isn’t just another fiction novel—it’s a deep dive into the human experience of karma, power, and the unintended consequences of our actions,” Len said. “If you’ve ever wondered whether your words could shape reality, this is a story you need to read.”

If Len Morrissey’s story of risk-taking and reinvention resonates with you, why not dive deeper into his world? Visit his website and check out Cursed Gift. Whether you're looking for business wisdom or a gripping read, Len has something to offer.

Taking Risks and Embracing Curiosity

Len’s advice to aspiring entrepreneurs, authors, or anyone facing a big life decision? Make mistakes. “The fear of making mistakes will ruin you as an entrepreneur,” he explained. “You have to make decisions and learn as you go.”

Intelligence, according to Len, is overrated. “Curiosity and hard work are what matter. We live short lives, so maximize the number of things you try.”

In both his business and creative endeavors, Len continues to push boundaries, learn from his failures, and surround himself with people who make him better. His journey from banking to entrepreneurship, from introverted networker to published author, serves as a powerful reminder to always embrace the unknown.

At StaffBuffalo, we understand that taking risks and embracing curiosity are essential ingredients for success in today’s dynamic business environment. Whether you’re a business leader seeking innovative ways to grow your organization or a talented professional ready to make your next career move, our team is here to support you. With expertise across diverse industries, we don’t just match skills to roles; we help you build resilient teams that thrive on curiosity and calculated risk.

Connect with us today, and let’s take the next step in your journey together.