When Stuart Draper, Trevor Erickson, and Brandon Winter joined forces at Stukent, they had no idea their collaboration would eventually support over a million students across 80 countries. In this recent episode of "Startups with Stu," the three former executives reunite to share insights from their journey of transforming an education technology startup from a home-based operation into a global powerhouse.

Stuart, the founder, along with former CMO Trevor Erickson (now founder of Deviant Inc.) and former CRO Brandon Winter (currently running FundRaiseGenius.com) offer a behind-the-scenes look at what it takes to build a successful startup. Their combined expertise in marketing, revenue generation, and business development created the perfect storm for Stukent's unprecedented growth. This blog post explores the key strategies and lessons they learned while scaling their EdTech business from working out of their homes to supporting hundreds of thousands of students worldwide.

Building a Business with a Unique Advantage  

When Stukent first launched, it had a distinct advantage that Stuart Draper constantly emphasized to his team: they were offering something that was "first in the world." This wasn't just marketing language—it was a fundamental truth that drove their strategy. The company created digital marketing and social media marketing educational products at a time when universities were struggling to teach these subjects effectively. As Stuart shared in the podcast, he conducted market research with the help of his early investor Corey Smith. They had students call over 100 business schools to gather feedback, which revealed a significant gap in digital marketing education that Stukent could fill.

The power of being first cannot be overstated. As Trevor Erickson pointed out during the discussion, having a product that was genuinely innovative gave them immediate traction. They weren't trying to convince potential customers to switch from a competitor—they were offering a solution to a problem that educators urgently needed to solve. This positioning allowed Stukent to grow rapidly, moving from zero to 10, then 10 to 100 professors in the first year, and continuing that exponential trajectory through subsequent years.

Stuart Draper's leadership approach included constantly reminding the team of this unique advantage. He described gathering everyone together and telling them, "There are very few people that get to have a time in their career where they get to sell something that no one else in the world has to offer." This mindset created both urgency and confidence, with Draper emphasizing that they had been "dealt a hand that only a stupid person would lose." By consistently reinforcing their distinctive position in the market, they aligned the entire organization around capitalizing on their first-mover advantage.

Nurturing Entrepreneurial Talent Within Your Company  

One fascinating aspect of Stukent's culture was how they approached entrepreneurship within their team. Many startups struggle with talented employees leaving to start their own ventures, but Stukent took a refreshingly different approach. Stuart acknowledged that many of his hires had entrepreneurial aspirations and were working for a startup precisely because they had an appetite for the startup environment—they were comfortable with risk and excited by the possibility of significant success.

Rather than discouraging these ambitions, Stuart embraced them, telling his team: "I want you to stay here and be happy here and I want to treat you right and I want you to give your all here. But I also understand that this is a part of your career and you'll do other things and that'll be okay." This philosophy had multiple benefits—it encouraged employees to think like entrepreneurs while working for Stukent, it fostered transparency about side hustles (with clear boundaries), and it created an environment where people could develop their skills with an eye toward their long-term goals.

Brandon Winter added an important implementation detail to this approach: regular one-on-one meetings. He conducted monthly meetings with leaders and quarterly meetings with team members, creating safe spaces for honest conversations about professional development. These meetings weren't just about performance at Stukent—they included discussions about personal goals, family life, and aspirations beyond the company. This holistic approach to employee development created strong loyalty while still supporting individual growth paths. As Brandon put it, "When you do that, they're invested in Stukent. They're invested in you as a leader."

Data-Driven Decision Making vs. Taking Action  

For aspiring entrepreneurs, one of the most common questions is how to validate ideas before investing significant time and capital. The team shared valuable insights about finding the right balance between research and action. When Stuart was first considering launching Stukent, he didn't rely solely on his instincts. Working with angel investor Cory Smith, he organized research where students called over 100 business schools to gather data about digital marketing education needs. This research confirmed his hypothesis about the market gap.

However, the executives also warned against analysis paralysis. Trevor emphasized the concept that "80% and done is better than 100% and never finished." In the fast-moving startup world, waiting for perfect data or perfect execution often means missing opportunities. As Stuart noted, sometimes with marketing ideas, it's better to simply "go to work and spend a little bit of money" to test concepts rather than trying to validate them through endless planning.

The team's approach balanced thoughtful research with decisive action. For Brandon Winter, this philosophy extended beyond the business itself—when evaluating a potential real estate venture after his time at Stukent, he focused on seeing the actual numbers from a friend's successful subdivision development, understanding the concrete inputs and outputs before making his own investment. This combination of data gathering and action orientation helped the team make informed decisions without becoming paralyzed by the pursuit of certainty.

Overcoming Challenges and Learning from Failures  

Despite their impressive growth trajectory, the Stukent team encountered numerous challenges along the way. One significant hurdle Stuart faced involved raising capital. Looking back, he recognized that in his second funding round, he undervalued the business, raising money at approximately two times top-line revenue when businesses in their space typically traded at more than five times. While this meant giving up more equity than necessary, Stuart found a silver lining: the lower valuation made it easier to deliver returns to investors, as the "field goal posts weren't so far out."

Another significant challenge came from an international partnership gone awry. Stuart and Trevor had to fly to Romania to try renegotiating terms with their software engineers who were building critical simulations. Despite touring "Dracula's Castle" together and making their case about unsustainable royalty rates, they couldn't reach better terms. This forced them to make a difficult pivot, investing in building their own simulation capabilities. While stressful at the time, Stuart described this as "a mega blessing in disguise" that ultimately strengthened the company.

The team also recognized missed opportunities in their scaling approach. Brandon admitted they maintained too small a sales team for too long, relying on just a couple of closers when they could have expanded earlier. However, they found an unexpected advantage in their hiring approach—using college students to sell to professors created natural rapport, as professors were "very comfortable with college students" and more forgiving of mistakes. Other early challenges included resistance to creating comprehensive teaching resources beyond the textbook, with Brandon recalling how they initially thought "the textbook was enough" until customer feedback made it clear that professors wanted complete course packages including syllabi, slide decks, and quiz banks.

Your Call to Action  

The journey of Stukent from a home-based startup to an education technology leader supporting over a million students worldwide offers valuable lessons for any entrepreneur. The team's willingness to share both victories and setbacks provides a roadmap for others looking to build successful ventures. Their story demonstrates that with the right product, team alignment, and strategic growth mindset, extraordinary success is possible even when starting from zero.

If you're building your own venture, consider the following action items based on the Stukent team's experience:

• Identify your unique advantage - What makes your offering truly different? If you have something that's "first in the world," make it central to your messaging and rally your team around this advantage.

• Embrace the entrepreneurial mindset within your team - Rather than fearing employees' ambitions, create a culture that nurtures their growth while channeling their entrepreneurial energy toward your company's success.

• Strike the right balance between research and action - Validate your ideas with targeted research, but don't let the pursuit of perfect data prevent you from moving forward.

• Learn from setbacks - When facing challenges, look for the hidden opportunities they might present. Some of Stukent's biggest "failures" ultimately strengthened their business.

• Listen to your frontline team members - Pay attention to feedback from those interacting directly with customers, as they'll identify friction points that need addressing.

The story of Stukent reminds us that building a successful startup isn't about avoiding all mistakes—it's about making the right strategic decisions, creating a strong team culture, and maintaining the courage to keep moving forward even when faced with obstacles. As Brandon Winter advised, "Fail fast, quickly make those mistakes and adjust instead of kind of sitting on your hands." By adopting this mindset and applying the lessons from these experienced executives, you can chart your own path to startup success.

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