Jonathan Thomas McDermott
Welcome to the digital home of Jonathan Thomas McDermott, a seasoned entrepreneur, connector, and founder of Stash Holdings Corp. This platform showcases Jonathan’s journey as a dynamic business builder and relationship architect, focused on cultivating ventures that blend innovation, authenticity, and long-term vision. Since founding Stash Holdings in 2019, Jonathan has become known for his hands-on approach to business development and his talent for forging impactful partnerships across a wide range of industries. Based in Chicago, he brings a worldly sensibility to his work, inspired by his love for European travel, especially the timeless beauty of Italy and Greece. As a devoted father who became a parent later in life, Jonathan approaches both business and fatherhood with a sense of purpose, presence, and perspective. Through his leadership, passion for human connection, and rediscovered commitment to personal wellness, including Transcendental Meditation—Jonathan continues to shape a legacy rooted in meaningful growth and lifelong curiosity.
About Jonathan Thomas McDermott
Jonathan Thomas McDermott is the founder and owner of Stash Holdings Corp, a forward-thinking private investment and operating company based in Chicago. Since launching the firm in 2019, Jonathan has built Stash Holdings into a multifaceted platform that reflects his entrepreneurial drive, his passion for connecting people, and his talent for identifying unique business opportunities. He thrives in business development and relationship cultivation, often leveraging his deep network and innate ability to open doors and foster long-term partnerships across industries.
Known for his collaborative style and strategic mindset, Jonathan is less interested in balance sheets and more inspired by vision, helping founders, operators, and creatives bring ideas to life, scale ventures, and create enduring value. At Stash Holdings, he stays close to the ground, working alongside his partners to navigate growth, operations, and innovation with a distinctly human touch.
Outside the boardroom, Jonathan’s life is anything but conventional. He became a father for the first time at 57 and proudly wears the title of “older dad” to his spirited three-year-old daughter. “You get less sleep, but more perspective,” he jokes, often reflecting on the joy and grounding that parenthood has brought to his life in this new chapter.
A devoted traveler with a particular love for Europe, Jonathan finds inspiration along the coastlines of Italy and the ancient ruins of Greece, where culture, history, and cuisine meet in perfect harmony. His recent return to Transcendental Meditation has also been a meaningful part of his wellness journey, offering a quiet counterbalance to the fast-paced world of entrepreneurship.
Jonathan’s story is one of reinvention, not just professionally, but personally. With a career that has evolved beyond traditional finance, he’s focused now on legacy, purpose, and meaningful connection. Whether mentoring young founders or exploring the Mediterranean with his family, Jonathan is most fulfilled when he’s building something, be it a business, a relationship, or a moment worth remembering.
Why Soft Skills Are the Real Hard Currency in Business Development
In the fast-paced, results-driven world of business development, attention often tilts toward hard metrics: pipeline numbers, revenue growth, conversion rates, and return on investment. Amidst this quantitative obsession, soft skills are frequently overshadowed, relegated to the realm of “nice to have” rather than “must-have.” Yet, as industries evolve and the lines between product and service blur, it is becoming increasingly clear that the most successful business developers aren’t merely those who can crunch numbers or deploy automation, they are the ones who can listen, empathize, inquire with intent, and cultivate trust.
Jonathan Thomas McDermott of Chicago understands that these soft skills, particularly emotional intelligence, active listening, genuine curiosity, and trust-building, are the true drivers of long-term success in business development. They are the foundation upon which meaningful relationships, lasting partnerships, and profitable deals are built.
Emotional Intelligence: The Core of Business Acumen
Emotional intelligence (EQ) is the ability to perceive, understand, manage, and regulate emotions, both in oneself and in others. In the context of business development, high EQ can be the difference between an effective pitch and a wasted opportunity. Business development professionals must navigate a myriad of emotional terrains, skeptical stakeholders, disinterested prospects, hesitant partners, and overworked decision-makers. Each interaction presents a chance to either alienate or align.
Professionals with high EQ can “read the room,” adapt their communication style, and address objections with empathy rather than defensiveness. They don’t bulldoze through conversations to meet sales quotas; instead, they engage authentically, sensing when to push and when to pause. They understand that behind every business decision lies a human — a person with concerns, ambitions, biases, and limitations. Jonathan Thomas McDermott explains that appealing to these emotional realities, rather than ignoring them, fosters connection and accelerates trust. Leaders like Satya Nadella of Microsoft have attributed organizational turnarounds to a focus on empathy and emotional intelligence. Business development is no different: the softer the approach, the stronger the results.
Listening: The Silent Deal-Closers
Ask any seasoned business development expert what turned a lukewarm lead into a closed deal, and you’ll often hear one word: listening. Not just hearing, but truly listening, with presence, patience, and a commitment to understanding rather than reacting.
Too often, business development conversations are dominated by pitch decks and value propositions. But prospects don’t want to be talked at; they want to be heard. Jonathan Thomas McDermott explains that they want their pain points validated, their unique challenges acknowledged, and their priorities respected. This requires practitioners to shift from performance mode to listening mode.
Active listening involves more than nodding and making affirming sounds. It requires asking open-ended questions, paraphrasing to confirm understanding, and pausing long enough for real dialogue to emerge. When clients or partners feel truly heard, they become far more open to collaboration. Listening builds rapport, signals respect and provides invaluable insights that no CRM tool can extract.
Curiosity: The Secret Weapon of Strategic Growth
Curiosity may be an overlooked trait in business development, but it is a quiet powerhouse. A curious mind resists assumptions and explores possibilities. Jonathan Thomas McDermott of Chicago explains that it does not enter a conversation with a fixed script but approaches each interaction as an opportunity to discover something new about the client, the industry, or the competitive landscape.
Curiosity leads to better questions. Better questions lead to deeper understanding. And deeper understanding leads to solutions that are not only relevant but also highly personalized. In a world where decision-makers are inundated with generic outreach and templated pitches, a curious business developer stands out as someone who truly seeks to serve, not just sell.
Curiosity also drives continuous improvement. It nudges professionals to learn about emerging technologies, evolving customer behaviors, and shifting market dynamics. Jonathan Thomas McDermott explains that this adaptive mindset fosters resilience, another underappreciated soft skill that’s crucial in the high-rejection environment of business development.
Trust: The Invisible Contract That Seals the Deal
Deals are rarely sealed on logic alone. Rational arguments, competitive pricing, and feature comparisons matter, but they are not enough. Trust is the glue that binds business relationships. Without it, even the most enticing offer will be met with hesitation.
Trust isn’t built overnight, nor is it won through charm or charisma. It is cultivated through consistency, transparency, and follow-through. A business development professional earns trust by doing what they say they’ll do, respecting timelines, acknowledging uncertainty, and prioritizing the client’s interest over short-term gains.
In strategic partnerships, where collaboration may span months or years, trust becomes even more critical. It allows for open conversations, constructive conflict, and a willingness to take calculated risks together. And in today’s economy, where trust in institutions is waning, the ability to engender trust at a personal level is a superpower.
The Bottom Line: Soft Skills, Strong Impact
The business world is slowly awakening to the reality that soft skills are not the antithesis of professionalism, they are its highest expression. Emotional intelligence, listening, curiosity, and trust-building are not just intangible virtues; they are strategic assets that drive tangible outcomes. They increase close rates, shorten sales cycles, reduce churn, and lay the groundwork for repeat business.
Jonathan Thomas McDermott emphasizes that as AI and automation take over routine tasks, the uniquely human qualities of empathy, insight, and relationship-building will only grow more valuable. In this new paradigm, the best business developers won’t be the most aggressive or the most technical. They’ll be the ones who connect, understand, adapt, and inspire. In short, they’ll be the ones who realize that in business development, soft skills are the real hard currency. And that currency pays the highest dividends.
Thank you for visiting the online portfolio of Jonathan Thomas McDermott, a seasoned entrepreneur and founder of Stash Holdings Corp. With a career grounded in strategic business development and a passion for building meaningful relationships, Jonathan has carved out a unique space where innovation, connection, and thoughtful leadership converge. Since launching Stash Holdings in 2019, he has dedicated himself to empowering ventures with long-term vision, guiding them with a hands-on approach that emphasizes collaboration, authenticity, and smart growth. His work is shaped not only by professional expertise but also by life experience, from becoming a first-time father at 57 to rediscovering the benefits of Transcendental Meditation as part of a holistic wellness journey. Fueled by a love for European travel, especially the culture-rich landscapes of Italy and Greece, Jonathan Thomas McDermott of Chicago brings a global perspective to everything he touches. Through his ability to connect people, ideas, and opportunities, he continues to inspire a more human-centered approach to entrepreneurship and legacy-building.