Thinking about going into sales? Listen to this podcast!

In this episode of The Education Road, we sit down with Michael Shulman, whose career path is rooted in sales!

Michael’s academic road began at York University, where he completed an Honours BA in Business Economics with a specialization in finance. Along the way, he discovered a strong aptitude for accounting and economics, skills that would later prove invaluable.

Although he originally envisioned a future in investment banking, his career took a different turn. After starting in corporate finance at Bombardier, a moment reviewing sales commission structures sparked a realization: he wanted to be on the revenue-generating side of the business. That decision launched him into tech sales, first through finance roles in major organizations like Sun Microsystems, then progressively closer to end-user enterprise sales.

Throughout the conversation, Michael breaks down what sales really looks like at the enterprise level. It’s not quick transactions or movie-style theatrics. It’s long sales cycles, strategic account planning, navigating budget cycles, building C-level relationships, and sometimes waiting years to close a deal. He shares how understanding accounting, balance sheets, international economics, and stakeholder dynamics allows him to have meaningful conversations with CFOs, CIOs, and CISOs.

The episode also pulls back the curtain on compensation structures (base + commission, quotas, accelerators), the realities of prospecting, and the discipline required to consistently perform. One lesson that stuck with Michael from his mentor: “Always be prospecting.” In enterprise sales, if you’re not planting seeds today, you won’t be harvesting deals tomorrow.

For students curious about sales, Michael offers candid advice: there’s no single required degree, but understanding business fundamentals helps. And if you want to get into sales, there is a more conventional path than the one he took, starting as an SDR and building from there.

At its core, this episode explores how an education in finance and global affairs can translate into a high-impact career in enterprise technology sales and why the ability to understand systems, incentives, and people is what ultimately drives success.

Diversified education and the non-traditional education path to career!

In this episode of The Education Road, we speak with Christine Gadsby, Chief Security Advisor at BlackBerry, whose education road is, in her own words, “non-traditional and very bumpy.” Christine’s story is a powerful reminder that learning paths are unique and often not expected.

Christine begins by sharing the reality of her childhood. In high school, her focus wasn’t on a future career, but on getting through the day. As a teenage mother, survival became the priority, and higher education wasn’t immediately part of the picture.

Her path into post-secondary education came later and in pieces. Christine took classes at the University of Washington, but ultimately completed her degree at Western Governors University, earning credentials in information technology and business management.

She then worked her way into technology and security roles, gradually building expertise through hands-on experience. Over time, that foundation led her to BlackBerry, where she grew through multiple roles before becoming Chief Security Advisor.

Throughout the conversation, Christine emphasizes how different her reality was from the traditional “college-to-career” narrative. She speaks candidly about what it means to learn without safety nets. Her story challenges the idea that success requires early clarity or privilege, and instead highlights resilience, grit, and the willingness to keep going.

Mike and Christine also discuss how background shapes leadership. Christine reflects on how her experiences inform the way she approaches security, risk, and decision-making today.

This episode won't touch upon polished resumes or perfect plans. Instead, we'll talk about building something meaningful from unstable ground, and recognizing that education often happens in fragments, including late nights, second chances, and hard-earned confidence.

It’s okay to pursue passions and don’t be afraid to chase the unknown

In this episode, we sit down with Ali Crawford, a Senior Research Analyst at the Center for Security and Emerging Technology (CSET) at Georgetown University. Ali shares her continuous and unexpected journey, taking listeners from the starting blocks of collegiate track and field to the complex world of national security and cyber policy.

The conversation begins with Ali’s background as a Division II sprinter and hurdler at West Virginia Wesleyan College. She discusses the discipline required to balance academics with athletics and the transition to becoming a "NARP" (Non-Athletic Regular Person) after graduation. Ali reveals how a fascination with international business and a pivotal class taught by a former FBI agent during her Master’s program led her to carve out a niche in intelligence and cyber policy.

Mike and Ali then dive deep into the current state of the cybersecurity workforce. They explore the "broken first rung" of the career ladder, debating why entry-level talent struggles to find work despite the reported massive labor shortages. Ali offers expert insights into the disconnect between higher education and workforce demands, the rise of "ghost postings," and the critical need for skills-based learning over purely theoretical degrees.

For listeners who worry that they haven't found their "calling" yet, Ali’s story offers a powerful reassurance: you don't need a perfect plan to end up in a place your younger self would admire.

Her journey underscores that progress is rarely a straight line. It's "continuous and unexpected," often shaped by the detours we take and the mentors we meet along the way. At its heart, this episode proves that education extends far beyond the classroom; it is found in the courage to embrace uncertainty and the willingness to simply chase the unknown.

Prepare to be disappointed!

In this episode of The Education Road, we chat with Ian Kalman, founder and creative director of Bald Guy Greetings, the irreverent, hilarious, and wildly relatable greeting card company found in hundreds of stores across North America.

Ian kicks things off with what he calls “a road full of questionable choices that somehow worked out,” and that phrase couldn’t sum up his story better. From dreaming of writing witty ad copy in college to running a nationally recognized greeting card business, Ian’s journey proves that the best careers often start as happy accidents.

He takes us back to his time at San Jose State University, where he majored in advertising and minored in psychology, a combination that would later help him connect with audiences on a deeply human level. After graduating, Ian landed his dream job in advertising, working on iconic campaigns for Budweiser, E*TRADE, and the Oakland A’s.

But everything changed with a birthday cake.

What started as a joke written in frosting sparked an idea: What if greeting cards were actually funny? On a plane ride shortly after, Ian began jotting down card ideas — 60 in total. Twelve of them became the first Bald Guy Greetings collection, and the rest is history.

Mike and Ian talk about the early struggles of starting a business without a roadmap. No entrepreneurship courses, no investors, just a writer who wanted to make people laugh. Ian admits that his college education didn’t prepare him for payroll, taxes, or packaging orders, but it did teach him creativity, persistence, and empathy.

Ian also opens up about his creative process, describing it as spontaneous and joy-driven. He keeps hundreds of ideas in his phone notes, drawing inspiration from overheard conversations, awkward social moments, and life’s little absurdities. With over 350 cards in circulation today, his brand has become a cult favorite for people who prefer laughter over sentimentality.

“If it makes me laugh, I’ll make it. I’d rather fail on my own terms than succeed at something that doesn’t feel like me.”

It’s that authenticity that’s made Bald Guy Greetings such a success and why so many customers, like Mike’s own family, refuse to buy any other cards.

By the end of the episode, you’ll see why Ian’s self-proclaimed “questionable choices” were anything but. His story is a reminder that passion, persistence, and a sense of humor can take you further than any perfect plan ever could.

How to find what doesn't feel like work!

In this episode of The Education Road, we sit down with Jacob Robinson, an attorney turned sports writer for The Athletic, whose winding journey from law school to becoming a writer covering the NFL is a testament to the power of following your curiosity and doing the reps.

Jacob’s story begins in Ontario, where a dual-degree business program at Brock University led him to Germany for two years of study abroad. That experience, he says, changed everything: living in a tiny village outside Frankfurt, learning to be resourceful, and discovering a love for exploration that would later define his career choices.

After earning degrees in both Canada and Germany, Jacob went on to law school through the University of Windsor and the University of Detroit Mercy, where he earned credentials on both sides of the border.

But it was a single Malcolm Gladwell book that changed his trajectory. Inspired by Outliers, Jacob realized that success often comes from being in the right place at the right time, and for him, that place was blockchain. While studying law, he dove deep into crypto policy, took a chance on a niche elective course, and became an early voice in decentralized law. That curiosity led to a role with the Ethereum Foundation and the creation of a popular podcast exploring crypto regulation.

Yet, the real twist came when Jacob’s side project, a fantasy football newsletter he started for fun, exploded overnight on Reddit. What began as five (forced) subscribers grew to thousands, and eventually caught the attention of The Athletic. Fast-forward to today, Jacob writes the largest NFL newsletter in the world, with over 1.4 million subscribers, delivering daily insights, humor, and analysis to football fans everywhere.

His advice to students and aspiring creators is simple: Don’t wait for permission. Start writing, start posting, start building. Whether it’s a podcast, blog, or newsletter, your work is your proof.

Jacob’s story captures what The Education Road is all about: the unpredictable, deeply human journey of learning, growing, and eventually finding work that doesn’t feel like work.

Solving the problem of isolation

In this episode, we sit down with Ariella Racco, CEO and co-founder of CoLab Education, to explore her fascinating journey from teacher to edtech entrepreneur and how she’s redefining what collaboration means for educators.

Ariella never planned to become a teacher. Drawn first to art and culture, she stumbled into education almost by accident. It was a backup plan that quickly became a calling. After earning her degree from McGill, she spent nearly a decade in classrooms in Canada and abroad, teaching everything from kindergarten to middle school science. Along the way, she learned that teaching wasn’t just about content. It was about connection, creativity, and constant adaptation.

She and Mike discuss the evolution of classrooms, from hands-on group learning to post-pandemic isolation and the heavy reliance on technology. Ariella reflects on how COVID transformed the way teachers and students relate, the loss of human connection that followed, and the urgent need to rebuild community in education.

Her time teaching internationally — from Toronto to Spain — gave her a global perspective on learning cultures and how technology can both help and hinder authentic engagement. That perspective, combined with her entrepreneurial spirit (first seen in a small pandemic-born dog accessory business called Pup + Pine), sparked an idea: teachers needed their own space to connect, collaborate, and grow.

That spark became CoLab Education, a professional networking and collaboration platform for K–12 educators.

Throughout the conversation, Ariella’s story reflects the heart of The Education Road: the unpredictable, winding journey from one chapter to the next. From a McGill student unsure of her path, to a beloved science teacher, to a global educator and now tech founder, Ariella embodies what it means to be a lifelong learner.

Her advice to young listeners and aspiring leaders? Don’t chase a title — chase a problem worth solving. Whether in the classroom or the boardroom, her message rings clear: learning never stops, and the best solutions start when you ask, “How can I make this better for others?”

If you’ve ever wondered what happens when a passionate educator steps outside the classroom to reinvent the system itself, this conversation will inspire you.

The Education Roads: everybody has their own!

In this episode of The Education Roads, we talk with David A. Wheeler, a lifelong learner, engineer, and current Director of Open Source Supply Chain Security at the Linux Foundation, who also teaches as an adjunct at George Mason University.

David’s path isn’t a single straight line; it’s a series of deliberate experiments driven by curiosity, hands-on tinkering, and a stubborn appetite for solving real problems.

David traces his start to an early obsession with electronics and the thrill of taking apart and rebuilding devices. That practical curiosity led him through an electronics engineering degree, decades of self-directed software work, and eventually formal graduate study (master’s and a PhD completed over many years) to fill gaps and formalize his learning. He describes himself as “mostly self-taught” who later went back for degrees to round out what he hadn’t learned on his own.

David emphasizes an engineering mindset: define requirements, weigh trade-offs, and pick tools that reliably solve the problem. Not whatever’s trendy. He urges new developers to start small, learn one language well (Python or JavaScript are good entry points), but to eventually learn lower-level concepts like assembly and memory so they truly understand how computers behave.

Throughout the conversation, David returns to two themes: trade-offs (there are no silver bullets) and lifelong learning. Be scrappy, build small projects to learn, read widely, and accept feedback as fuel for improvement. For listeners who teach, build, or ship software, this episode is a useful blend of practical career advice, a clear-eyed take on AI’s place in development, and a humane view of what it takes to keep learning for a lifetime.

Unconventional Paths Lead to Interesting Places

In this episode of The Education Road, we sit down with Eric, whose career journey proves that a degree in history can lead just about anywhere, including into the world of AI, automation, and customer education.

Eric describes his path as serendipitous, and it’s hard to disagree. From studying History and Technology Studies to becoming an AI and Automation Transformation Lead at Zapier, his story is a masterclass in how curiosity, communication, and creativity can open unexpected doors.

After graduating, Eric dove into the tech world. But he soon realized he craved more creativity and human interaction and this led him back to academia as an academic technologist, helping universities design and implement digital learning experiences. From virtual reality projects to lightboard teaching tools, Eric brought innovation to classrooms on a shoestring budget, proving that constraint often fuels creativity.

Education remained at the heart of everything he did. As he transitioned into instructional design and later into customer education roles at Heap, SmartCat, and ultimately Zapier, Eric discovered a field where his passions for technology, teaching, and communication converged. He explains how customer education isn’t just about training. It’s about helping people truly understand and connect with the tools they use.

Mike and Eric also explore the evolution of online learning, especially after the pandemic. Eric advocates that online education, when done thoughtfully, can be more accessible, inclusive, and engaging than many assume. Drawing from his own Master’s in Educational Technology Leadership at George Washington University and an MBA in Leadership and Change, he reflects on what makes great online education.

Beyond the degrees and job titles, Eric’s story is ultimately about connection between people, disciplines, and ideas.

Whether you’re a student wondering how your degree will fit into the real world, an educator navigating technology’s rapid pace, or a professional exploring what’s next, Eric’s story reminds us that the most rewarding journeys are rarely linear.

A journey that doesn’t stop!

In this episode of The Education Road, we sit down with Ash, Director of Event Marketing at VulnCheck, whose journey from English and linguistics major to cybersecurity marketing leader is full of unexpected turns and inspiring lessons.

Ash shares how her parents, breaking the cultural stereotype, encouraged her to follow her passions rather than a traditional pre-med path. That decision led her to major in English and linguistics at Wayne State University, where a professor spotted her talent and invited her to become an undergraduate writing tutor. From there, her love of writing and editing evolved into a lifelong exploration of how words connect people, ideas, and organizations.

Her early work at Domino’s taught her to write with clarity and purpose for different audiences, while her move to Duo Security immersed her in cybersecurity and showed her how a values-driven culture and transparent leadership can define a company’s success.

Ash talks about the art of editing, the nuances of business writing, and how communication sits at the heart of every strong organization. She reflects on her time teaching business communication at Wayne State as an adjunct lecturer, her belief in empowering students with real-world skills, and her philosophy that “good writers are good editors.”

If you’ve ever wondered how a background in literature can lead to a leadership role in tech, or how communication truly powers culture and innovation, Ash’s story will leave you inspired!

It’s All About Ecosystems: Dan Applequist on Open Source, Standards, and Lifelong Learning

In this episode of The Education Road, we sit down with Dan Applequist, Open Source Strategist and longtime advocate for the open web.

Dan shares how he nearly dropped out of university, why discovering cognitive science saved his academic journey, and the lasting lessons from courses in decision-making and creative writing that still guide his leadership today. He reflects on teaching himself to code as a teen, discovering the power of community through early internet bulletin boards, and eventually building a career at the intersection of open source, open standards, and public advocacy.

Dan has been at the center of the web’s most pivotal shifts. Along the way, he’s grown from an introverted student to a global conference speaker, mentor, and connector who is always pushing for more openness, more collaboration, and more ethical technology.

Today, he works across ecosystems: from the OpenSSF to W3C to content authenticity initiatives, ensuring that the open source projects we all rely on remain secure, transparent, and sustainable. For students and developers looking to break in, his advice is simple: start a GitHub, contribute to projects you care about, show your passion, and share your work.

Dan’s story is proof that curiosity, persistence, and community make all the difference.