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.
The love of photography and film!
In this episode of The Education Road, we sit down with Rob Fiocca, a Toronto-based photographer and commercial director whose career spans from the early days of darkroom film processing to high-budget ad campaigns for some of the world’s biggest brands.
Rob shares his journey, starting from Humber College’s Creative Photography program, and how early co-op placements with catalog and fashion photographers gave him his first taste of the industry. From those beginnings, he worked his way up through catalog studios, honing his craft, developing a style, and eventually striking out on his own.
He opens up about the challenges of adapting to digital after film, staying current with ever-changing trends, and the differences between capturing a still life and directing a 30-second spot.
Rob also reflects on the “soft skills” behind the lens: humility, collaboration, taking criticism, and building trust with clients and crews. He speaks candidly about the bittersweet realities of the creative business, the importance of passion, and how AI may disrupt photography and filmmaking the way digital once did.
If you’ve ever been curious about what it’s like to build a career in photography, navigate the business side of the arts, or transition from stills to film, Rob’s story is a masterclass in persistence, adaptability, and love for the craft.
Accidental career
In this episode of The Education Road, we sit down with Susan, whose path has been anything but linear. What began as a philosophy major at McGill turned into a detour where she found herself working alongside pioneers of the early internet. That unexpected turn launched a career in technical writing, content creation, and eventually customer education! Fields that she never planned to enter but came to love.
Susan reflects on her years as a technical writer and her transition into leadership roles that taught her the messy, rewarding art of managing people.
Now in marketing, Susan talks about why communication skills matter more than ever, and how curiosity and adaptability shaped her career. Along the way, we dive into her love of reading, her belief in lifelong learning, and her thoughts on how AI is changing the craft of writing without replacing the need for human voice.
If you’ve ever felt uncertain about your path—or wondered how a career could unfold without a master plan—Susan’s story is proof that accidental turns can lead to extraordinary places. And yes, those em dashes were not AI!
Optimizing for fun!
In this episode of The Education Road, we sit down with Randall, whose education road is anything but traditional. After dropping out of UC Santa Cruz, Randall carved his own path through sheer curiosity, hustle, and a relentless drive to learn by doing.
He shares how tinkering with DOS systems and hacking as a kid sparked his lifelong passion for programming. Early on, Randall dove deep into telecom, building open source distros, scaling services to millions of users, and even creating one of the first API services for caller ID data.
Along the way, Randall reflects on the lessons of self-directed learning, the power of wearing many hats, and why becoming both a strong engineer and a good communicator is the ultimate career multiplier.
If you’ve ever wondered whether you need a degree to succeed in tech, how DevRel really works, or how to keep learning alive throughout your career, this conversation offers a refreshing, unfiltered look at building a career on your own terms.
How to accidentally be an academic
In this episode of The Education Road, we sit down with Joe McManus, CISO at Grafana, whose circuitous educational journey led from dreams of being a professional mountain biker to becoming a cybersecurity leader and passionate educator.
Joe's transition into technology happened organically during the dot-com boom when a consulting opportunity introduced him to Unix system administration.
A pivotal moment came early in his career when a compromised web server at the City of Boulder sparked his interest in cybersecurity.
After he earned a Master's in Information Technology and Management, he eventually transitioned into full-time academia at the University of Colorado. As a professor, he developed innovative cybersecurity curricula that combined technical rigor with business practicality, requiring students to take business courses alongside their technical studies.
Joe left full-time academia and his career path continued evolving through CISO roles at various companies.
Currently teaching part-time at Utah State University while serving as CISO at Grafana, Joe embodies the intersection of education and industry practice. His teaching approach has evolved to meet changing student needs, incorporating flexible assessment methods and real-world projects.
Joe's journey illustrates how curiosity, continuous learning, and willingness to embrace unexpected opportunities can create a fulfilling career spanning industry leadership and academic impact, proving that sometimes the most rewarding paths are indeed the most circuitous ones.
Lifelong learning from the skies
In this episode of The Education Road, we sit down with Gary Olson. He is now a Chief Revenue Officer, but his remarkable journey began at the United States Air Force Academ,y where he earned a Bachelor of Science in Engineering with a minor in Political Science. This was a combination that would prove foundational to his future success in both technical and people-focused roles.
After serving as a pilot and transitioning into military intelligence, Gary faced a life-changing decision where he chose his family over a military career. He said it was the toughest but best decision of his life.
As a CRO, Gary operates on three core pillars: releasing control to become an orchestrator, embracing unpredictability while building scalable business models, and practicing extreme ownership - giving credit for successes while taking responsibility for failures. With 35+ years in cybersecurity, he views this field as his craft, requiring total commitment and continuous learning.
This interview reveals Gary as a leader who seamlessly blends military discipline with business innovation. He is an inspiring example of how diverse experiences create exceptional leaders.
In this episode of The Education Road, we sit down with Naomi Thibault! She set out to be a teacher and waited for postings that never came. But one unexpected opportunity changed everything. She stepped into a city service role, discovered a calling, and never looked back.
Inside the fire department, Naomi moved through roles that now inform her leadership: emergency management, public education, fire prevention, inspection, and investigation. She chased every course she could and learned as much as she could from every available resource.
Today, she serves as Deputy Chief, Fire Prevention, Education & Emergency Management, a role that marries public safety, policy, and people skills.
Naomi is candid about her role and believes the culture can change. After decades without hiring a single woman, her department has begun to add more women and she’s determined to make the entire service better reflect the community it serves.
In this episode of The Education Road, we speak with Seeyew Mo, an advocate working at the intersection of data, education, and social impact. Seeyew shares his unexpected path from completing his computer science degree and working as a developer, to completing his Master's in Public Administration, Political Science, and Government, and being appointed as the first-ever Assistant National Cyber Director on Workforce, Education, and Economic Advancement!
He opens up about his early influences in public service, the transition from being a developer to working with policies and governance.
Seeyew offers an honest look at technology, politics, and finding joy in mission-driven work. If you care about equity in education, transparency in policy, or just how to make an impact, this conversation is for you.
In this episode of The Education Road, we dive deep into the dynamic career of Ryan Strynatka, a geography major turned COO! Ryan shares candid reflections on his early days in education, how he transitioned to product, and how his passion for solving problems led him to where he is today.
Ryan talks openly about the emotional challenges of entrepreneurship and what it means to rediscover curiosity.
If you've ever wondered what happens after you leave a structured career path, Ryan’s story offers both guidance and heart.
Somehow, Tony ended up in marketing.
In this episode of The Education Road, we sit down with Tony Sleva to explore his winding journey from a computer science student to a content leader shaping the voice of innovative tech companies. Tony opens up about his early days building computers in high school, his shift from computer science to information systems, and how a hidden passion for writing ultimately pulled him into marketing.
We talk about the art of crafting a company’s voice, the challenge of translating technical concepts into engaging stories, and why embracing critique is vital for any writer’s growth. Tony also reflects on lessons learned from comedy writing and screenwriting courses, sharing how these creative pursuits sharpened his storytelling and helped him bring humor and humanity into technical spaces.
Whether you’re a developer curious about breaking into marketing, a writer navigating tech-heavy industries, or just someone fascinated by career pivots, this conversation offers insights, laughter, and inspiration for your own journey.