How great leadership can heal, inspire, and transform, with Alan Todd.

Welcome back to Coding Temples: Agile Leaders! In our latest episode, our CEO and host, Evan Shy, had the privilege of sitting down with the multi-talented Alan Todd. Alan shared invaluable insights and strategies for leaders aiming to increase velocity, drive innovation, and make a meaningful impact in growing organizations.

(Deel like you’re missing out? Catch up with the full episode now on YouTube or Spotify.)

Alan is no stranger to success. Not only is he the host of the widely acclaimed podcast “Leading Up,” which recently clinched the coveted number one spot in business and management, and 17th overall on Apple Podcasts, but he’s also a seasoned entrepreneur. With three successful exits in the ed-tech sector under his belt, Alan’s expertise is undeniable. His entrepreneurial journey led him to become the Vice President at Udemy, following the acquisition of his startup Corp U in 2021.


Who is Alan?

Alan Todd’s entrepreneurial spirit ignited during his senior year in college in 1986. Faced with an unprepared professor in an “Introduction to Microcomputer” course, Alan took the initiative to explore an IBM 5150 PC and Lotus 1-2-3 software on his own. This hands-on experience sparked his passion for technology and set him on a path that would define his career.

By the age of 22, Alan was already helping others learn to use personal computers, sensing the beginning of a technological wave. Over the next decade, he founded tech boot camps focused on Novell networking, databases, and the emerging Microsoft Office suite and Windows platform. He bootstrapped his ventures, relishing in the process of educating and witnessing people’s improvement.

During this period of rapid technological advancement, Alan and his team at KnowledgeSoft developed a groundbreaking learning management system (LMS). Recognizing the potential of the internet and browsers like Netscape, Alan foresaw the revolutionary impact of LMS, which would eliminate the need to install software on individual machines.

KnowledgeSoft’s innovative approach attracted the attention of Gartner, leading to its acquisition and the spin-off of the software company. The learning management system evolved into KnowledgePlanet, which navigated through the dot-com bubble burst and was eventually acquired by a private equity group.

Following the sale of KnowledgePlanet, Alan pursued graduate school and conceptualized Corp U, an online platform aimed at delivering executive education. In 2010, when online education was predominantly focused on tech skills, Corp U pioneered leadership and executive education online.

Today, Alan’s journey has come full circle with Corp U being acquired by Udemy in 2021 and rebranded as Udemy Business Leadership Academy. Through his podcast “Leading Up” with Udemy, Alan continues to evangelize leadership and management development, reflecting on the practices of great leaders and the impact they have on the world. His story is a testament to foresight, adaptability, and relentless innovation in the ever-evolving tech landscape.


Turning Vision into Passion

At Corp U and Udemy, Alan Todd chose to stay on board following the acquisitions, unlike his previous startups where he was eager to move on to the next opportunity. This decision was influenced by the close relationship he built with Udemy’s CEO, Greg Brown, over the years. Greg expressed a desire for Alan to help build a leadership development capability and integrate Corp U’s offerings into Udemy’s broader functions such as sales and customer success. Alan agreed to stay on and has since focused on recruiting his successor, bringing in new managers and leaders, and evangelizing the product through his podcast as part of his commitment to Udemy’s success.


Career Development

When asked “What skills do you think have been most impactful to your success?”, Alan credited his curiosity.

Alan’s entrepreneurial journey has been defined by two critical skills that have contributed significantly to his success: relentless learning and intense perseverance. While many may credit their achievements to specific strategies or shortcuts, Alan emphasizes the enduring value of being a passionate reader and learner. His commitment to continuous education has allowed him to not only identify emerging technological waves but also to build and execute products effectively to ride those waves successfully.

However, Alan also places a high value on perseverance, especially during challenging times that often go unnoticed on paper but are very real in the day-to-day operations of a business. He describes entrepreneurship as a rollercoaster ride filled with highs and lows, good days and bad days, and even good years and bad years. Despite facing existential crises and setbacks in all three of his companies, Alan’s unwavering perseverance has been a driving force behind his ability to overcome obstacles and continue moving forward.


How to make sure you get into the right rooms.

It’s no secret at this point that Alan’s entrepreneurial journey exemplifies the transformative power of unwavering belief, strategic focus, and effective relationship-building. From the outset, Alan prioritized creating the best possible product and forming strategic partnerships with chief learning officers (CLOs) as a starting point. This approach allowed him to work his way up the organizational ladder, gaining endorsements from division presidents and eventually CEOs. By demonstrating tangible value and efficiency in digital learning, Alan was able to turn skeptics into believers, convincing them of the merits of a more streamlined and cost-effective approach to leadership development.


What fuels an unyielding passion for leadership and professional development?

For Alan, the journey began unexpectedly. From teaching computer basics as a Novell certified network instructor to managing teams and eventually diving into teaching the Dale Carnegie course, his path was a blend of tech skills and soft skills acquisition. This journey instilled in him a profound appreciation for the transformative power of learning. Alan witnessed firsthand how learning can change lives, not just in terms of career growth but also in personal well-being and relationships.

Reflecting on his experiences at KnowledgeSoft, KnowledgePlanet, and Corp U, Alan’s purpose crystallized: a fervent pursuit of wisdom to foster shared prosperity through teaching and learning. This passion led him to explore and champion cohort-based learning, a methodology rooted in socio-cultural theory. Contrary to traditional behaviorist approaches prevalent in corporate training, Alan’s insights from his graduate studies at the University of Pennsylvania emphasized the significance of engagement, collaboration, and community in the learning process.


How do leaders prioritize their own development?

When it comes to leadership development, the debate often centers around the value of formal academic training versus experiential learning. For many successful leaders, the school of hard knocks, or experiential learning, has been their primary teacher. Take Abraham Lincoln, for instance, who became a lawyer and eventually the President of the United States through self-directed reading. Elon Musk, too, attributes much of his knowledge to reading books rather than formal education.

However, as one progresses in their career, there often comes a time when connecting theory to practice becomes essential. For some, like our guest speaker, this realization came after leaving a specific industry. Despite having taken courses on Finance and Accounting in college, real-world application proved to be the true teacher. This individual not only learned the intricacies of finance but also pursued higher education, gaining deeper insights and becoming a more analytical thinker.


Can you be positive without taking a moment to see the negative?

Looking ahead, amidst the numerous successes throughout Alan’s career, there’s one burning question that drives his passion and ambition: How can he address the deteriorating human condition in advanced economies like America?

The statistics are alarming. The CDC reports a majority of us are unwell by their standards. A staggering 75% of people experience debilitating stress at work, according to a Sherm survey. Lack of sleep is affecting our cognitive abilities, and loneliness has reached epidemic proportions, equating to the health risks of smoking 15 cigarettes a day, as highlighted by Surgeon General Vivek Murthy. Moreover, our addiction to smartphones and constant distractions hinder our ability to focus and think deeply.

These issues, Alan believes, are failures of leadership. But herein lies the opportunity. Good leadership has the power to heal, inspire, and transform. Research supports that positive leadership not only improves well-being but also leads to longer, more prosperous lives and stronger relationships.

“That’s what I think great leadership can do.” – Alan Todd.

Alan is deeply committed to this vision: to cultivate strong leaders who can positively impact those around them, creating a ripple effect of positive change. Imagine a world where each leader, equipped with the right skills and mindset, influences 10 or 20 individuals to become better versions of themselves. The potential for exponential growth and positive impact is immense.

But leadership isn’t confined to the workplace. Our societal pillars, from education to religion, are crumbling. Alan believes that great leaders can be the catalysts for change, revitalizing these institutions and fostering healthier, happier communities.

“So, as I look to the future, my ambitious goal is clear: to dedicate my time and efforts to nurturing strong, positive leaders who can transform our world. Leaders who not only excel in their respective fields but also embody empathy, resilience, and the ability to inspire others. Together, we can create a ripple effect of positive change, one leader, one community, at a time.” – Paraphrased from Alan Todd.


As we wrapped up this enlightening conversation with Alan Todd, it’s evident that leadership is not merely about steering organizations toward success but also about fostering positive change in society. Alan’s journey, from his early days tinkering with computers to his role as a thought leader in executive education, underscores the importance of adaptability, perseverance, and continuous learning.

Alan’s unwavering commitment to creating impactful learning experiences, particularly through cohort-based learning, reminds us of the transformative power of human connection. In an era dominated by technological advancements, it’s heartening to see a leader like Alan championing the cause of human-centric learning, emphasizing the value of collaboration, engagement, and community.

Furthermore, Alan’s emphasis on the role of leaders in addressing the pressing issues of our time – from stress and loneliness to the challenges facing our societal institutions – serves as a clarion call to action. It’s not enough to excel in our respective fields; we must also strive to be empathetic, resilient, and inspiring leaders who can effect meaningful change.

As Alan aptly puts it, “great leadership can heal, inspire, and transform.” It’s a sentiment that resonates deeply and serves as a guiding principle for all aspiring leaders. The potential for exponential growth and positive impact is immense, and it all starts with each one of us committing to becoming better leaders and human beings.


So, as we look to the future, let us take inspiration from Alan’s journey and vision. Let us prioritize continuous learning, foster human connections, and work tirelessly to create a world where leadership is synonymous with empathy, resilience, and positive change. Together, we can make a difference, one leader, one community at a time.


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