Welcome to the first very episode of Generation E Radio, Whiteboard Youth Venture’s new podcast station. Each week, Whiteboard founder Frank Pobutkiewicz will be sitting down with real entrepreneurs who have started real companies that make real money.

The entrepreneurs we bring onto the Gen E podcast will come from diverse backgrounds working in a range of industries, including technology, advertising, automotive, legal, mobile apps, education, design, and more. The goal of each interview is to bring valuable advice to our listeners by sharing real stories about starting-up, selling, and scaling.

In the first episode, host Frank Pobutkiewicz shares his story about becoming an entrepreneur and a major setback that almost caused him to walk away from it all.

The Origin Story

Growing up, Frank was surrounded with entrepreneurs in his own family, but failed to recognize or appreciate it. His father owned an accounting practice, his grandfather owned a tavern, his great uncle owned a restaurant, and other family members had their own businesses.

Frank learned to love selling at a young age. Like many, he sold iced tea and lemonade curbside and figured out he could sell other items throughout the year, sometimes using his younger cousins to attract attention of passing cars.

During middle school, he offered to make website for each of the teachers in his school. And in high school, we continued to learn more about web development before receiving some odd advice from a guidance counselor. “By time you graduate from college, there won’t be any jobs left in computers,” he was told.

So he switched tracks and focused on his interest in international politics. After graduating from high school, he studied International Relations and Business at Boston University.

The First Entrepreneurial Experience

Funny enough, it wasn’t Frank’s business education at BU that led him to his first venture. Instead, he got involved in a debate organized called Model United Nations. By time Frank was a senior and was in a leadership position, he helped to transition the Model UN student club into the Boston University International Affairs Association, which had 300 members and a $250K budget.

Only after spending upwards of 40 hours per week working on the International Affairs Association did Frank realize this was his first real venture, albeit in a non-profit structure.

The First Launch

Career plans derailed for Frank during his senior year in college as the 2009 financial crash wreaked havoc on the jobs market. Forced into taking a temp job to pay the bills, Frank credits sitting in a cubicle for 8 hours a day as motivation to start his first education company.

Parlaying the experience he had in Model UN, he started the All-American Model UN Programs, a Model UN honor team made up of high-performing US high school students. The All-American Model UN team started as a single team that attended a conference in Beijing, which Frank helped to start while in college.

Soon, other conferences started inviting the All-American team to competitions around the world. This year, All-American teams will compete in Washington DC, Budapest, Hyderabad, Beijing, Cartagena, with an additional study program in Boston.

The Start of Whiteboard Youth Ventures

With news of the success of the All-American Model UN teams spreading, Frank has approached by international school teachers to host a new program in the United States for their students to attend. Working in the Cambridge Innovation Center in Kendall Square, Frank was surrounded by hundreds of other founders and decided that entrepreneurship could be a powerful vertical to use in an education context.

He developed the curriculum for the Young Entrepreneur Challenge, a week-long bootcamp and competition designed to teach high school students how to plan for their first companies. The YEC is still the flagship program of Whiteboard Youth Ventures and attracts over 50 students from around the world each year.

A Bad Decision with Serious Consequences

A year into the launch of Whiteboard and the Young Entrepreneur Challenge, Frank was invited to judge the final round of a high school pitch competition hosted by a local nonprofit. One of the student presenters discussed his plans to launch a new smart watch that could monitor movements to predict and prevent when people were falling asleep. Impressively, the student also had a working prototype and a manufacturer.

Frank offered to invest a small amount in the idea to pay for marketing, legal, and web development expenses. The student venture would only pay back this investment if they sold over $10,000 of products. While this is still the model used for the Whiteboard Incubator, the first investment went horribly wrong.

The student launched a successful Kickstarter campaign, raising over $23,000. They were able to sell another $5,000 preorders on their website. Frank wanted to make sure all of the customers received their products and was promised the watches would be delivered by Christmas.

In January, a customer called Frank to complain that he still hasn’t received his order. And then Frank found out a second Kickstarter campaign was launched without his knowledge and raised an additional $11,000.

At this point, Frank knew he was in a bad spot. Even though the student still owed over $6,000 to Whiteboard, Frank offered to close the deal for a one-time payment of $800. The student refused, and when his father got involved, things went from bad to worse. The father alleged Frank was orchestrating childhood slavery and after a bitter battle with attorneys, the deal imploded.

Mental Impact and Resurgence

The mental ramifications of this experience took a huge toll on Frank, and after months of contemplation, he decided to shut down all of his education ventures and walk away from entrepreneurship. The stress, anxiety, and regret became too much to shoulder.

During the wind-down period, Frank changed his daily routine, improved his nutrition and sleep schedule, and started making healthier choices. He started to enjoy his work again, and more importantly, was reminded of why he got into education in the first place– his students.

Ultimately, Frank decided to keep going. In 2017, the All-American Model UN Programs are stronger than they’ve ever been, and Whiteboard Youth Ventures is undergoing a rebirth. In addition to the YEC Boston, Frank is exploring new cities such as St. Louis; Bucharest, Romania; and several locations in the Middle East to host new program. The Incubator will continue to operate, and in 2018, Whiteboard will hopefully have its largest class.


Thanks for tuning into the first episode of Generation E. We’ll be back next week with an interview with benja founder and CEO, Andrew Chapin, who is also a Whiteboard Youth Ventures Entrepreneur-in-Residence. Andrew will share his story about founding benja and some other cool projects that he’s currently working on.