5 Questions with Roger Osorio, Community Leader

May 23, 2022

Roger Osorio is a reinvention coach and author with a mission to help people define success on their terms and build a life in alignment with their values, passion, and purpose. Roger has been walking his own journey to reinvention since 2005. In September 2022, his first book, The Journey to Reinvention, will hit stores.

As a global facilitator for Techstars Startup Weekend since 2014, he has facilitated more than 50 events and helped organize seven Startup Weekend events in NYC. 

Roger is also an entrepreneurship instructor at the University of Pennsylvania and Sarah Lawrence College. 

01. How did you get involved in Techstars Startup Programs?

I got involved with my first-ever Startup Weekend in January 2014 when a dear friend asked me to serve as a coach for the first youth Startup Weekend. A month later, that experience inspired me to participate in the next Startup Weekend event for the full weekend.

I was fortunate to have my idea get voted as one of the ideas we pursued all weekend and I recruited a great team. The experience was truly life-changing because after going through that process, you never see the world the same way again. After the event, an incredible woman on my team invited me to join her effort to host a Startup Weekend later that same year. By the end of 2014, I had helped organize a Startup Weekend, attended the Startup Weekend Summit, and became certified as a Startup Weekend Facilitator. Life was never the same after that year.

02. How have Techstars Startup Programs impacted your life?

We could dedicate an entire 90-minute interview to this question! Ever since 2014 when I fully became a part of the Startup Weekend family, life was never the same. I have enjoyed countless blessings thanks to Startup Weekend. I'm going to highlight just some of the magic moments along my journey.

In 2015, I started applying Startup Weekend frameworks and principles into my role as a middle school math teacher at an all-girls private school. It's no secret that teachers are provided with very few resources, often drawing on their own savings in order to deliver learning outcomes. The lean startup principles helped me become more innovative in the classroom and solve the difficult problems teachers encounter. What I learned from Startup Weekend helped me build solutions to empower my young girls to unleash their inner mathematicians!

In 2016, after eight years in education, I was ready to launch my next reinvention. That year, I felt stuck in my teaching career because no tech company seemed to be interested in hiring a middle school math teacher. Then, Startup Weekend came to the rescue!

I was scheduled to facilitate a Startup Weekend sponsored by IBM and one of the judges was a senior executive who reported to the CEO. Because applying for jobs with my resume wasn't working for me, I decided to "try out" for the company by delivering the best facilitator performance to date. After the event, that EVP reached out to set up a meeting and offered me an opportunity to join IBM. If not for Startup Weekend, I would not have had the space to put my skills on display. In my role at IBM, I had the opportunity to partner with incredible Startup Weekend organizers around the US to support and sponsor their events on behalf of IBM. This was a special opportunity to give back to the community a little bit of what it gave to me.

The last story I'll share here happened in 2018 when I had the opportunity to connect with leadership from Sarah Lawrence College and the University of Pennsylvania at two different Startup Weekends that I facilitated. They each extended me teaching contracts that year. At SLC, I helped them build a semester-long version of Startup Weekend for credit. At UPenn, I helped them add Startup Weekend elements into their master's program in education entrepreneurship. In 2022, I still work with both institutions and the lean startup process has helped me deliver constant and never-ending innovation.

Like I said, life was never the same again after I got involved in Startup Weekend back in 2014. Joining the Startup Weekend family was easily the most impactful decision I made in my life.

03. Why are you passionate about entrepreneurship?

For me, it wasn't actually about entrepreneurship at the beginning. It was more about empowering people to reinvent themselves into entrepreneurs. Like any reinvention, it's scary to step out of your comfort zone and the teacher and coach in me wanted to do my part to help participants explore this opportunity in a safe space so that they could decide for themselves if this was the next step on their journey.

That said, along the way I could not help but fall in love with entrepreneurship. There is something quite special about spotting a problem and knowing there is probably something you can do about it. What I love most about entrepreneurship is the mindset and belief that problems are all solvable. As a former math teacher, this resonated with me.

04. How else are you involved in your community's startup ecosystem?

In my own startup ecosystem in NYC, I got involved as an organizer in 2016 when the lead organizer at the time was looking to pass the baton. The new team and I organized about seven or eight Startup Weekends between 2016-2019, including the one that got me recruited by IBM. As the years passed, I was inspired by a former Startup Weekend regional manager, Adam Haun, to support first-time Startup Weekend organizers around the world. Since then, I have worked to support organizing teams in bringing the possibilities of Startup Weekend to their community. In fact, as I write this, I'm in Cornwall, UK, where I just facilitated their first-ever Startup Weekend. I've been working with their organizers for many months to help them bring their vision to life.

05. What's next for your community's entrepreneurship ecosystem?

Great question, I'm not sure. There's been such a great history of Startup Weekend in NYC going back to around 2010 (I believe). Those organizers did such a great job to lay down a foundation from which so many other great entrepreneurship programs developed. Thanks to their incredible work, aspiring entrepreneurs have an abundance of opportunities to bring their ideas to life. In addition, thanks to them I had the opportunity to take my involvement to the highest levels. I owe a great deal to the work done by Frank Denbow and Andrew Young in building a great Startup Weekend NYC community.

I think the next step for the entrepreneurship ecosystem in NYC is to share and empower working professionals with the entrepreneurial and innovative mindset necessary to help reinvent what corporate work looks like post-pandemic. I believe this collaboration between entrepreneurs and corporations will unleash massive value for both communities.