Episode 16 – Being an Outsider

Whether you have started a new job, moved to a different town, or created a social enterprise, at one time or another we have all felt some sense of being an outsider. In this week’s episode, Jerrid and Courtney embrace the role of the outsider and discuss how this position provides the perfect opportunity for innovation. As Jerrid defines it, outsiders in the social entrepreneurship world are people who are not of their industries before their social enterprise endeavors.

“I get a kick out of being an outsider constantly. It allows me to be creative.” – Bill Hicks

A significant benefit of being an outsider is the potential for outside-the-box thinking. Outsiders tend not to have the preconceived notions that more experienced people in the field may possess. Industry insiders are by nature close to their professions and have an intimate view of the inner workings of their jobs. While this closeness reaps its rewards, it may also limit their ability to approach issues within their perspective fields from a fresh point of view. Thus, the need for the outsider.  

In the social entrepreneurship world, the outsider is typically met with praise, but sometimes confusion may occur as well. On the one hand, outsiders may generate excitement as they disrupt the status quo and seek to remedy a social ill. On the other hand, the industry insiders may not take them as seriously due to the outsiders’ newness to the field. However, as outsiders become successful in their missions and generate profits, they become more respected by those who may have questioned their capabilities.

So, does it take an outsider to solve lofty problems? Maybe not always, but this was certainly the case in social entrepreneurial success stories Clean the World founded by Shawn Siepler and Recycle Across America founded by Mitch Hedlund. The owners of these social enterprises were very much outsiders when they started their respective businesses which may have given them the distance needed to bring their innovative solutions to life.


Episode 15 – Fear of Failure


The old saying goes “there’s nothing to fear but fear itself,” but how true is this when it comes to failure? Failure is often seen in a negative light instead of a valuable learning tool. This week Courtney and Jerrid discuss their failures, and the role failure plays in the field of social entrepreneurship.

For Courtney, failure isn’t a dirty word. Whether it is an opportunity for growth and self-reflection. This was indeed the case when she offered a staff book discussion. Courtney was super excited to share her love of reading with her coworkers and put a lot of thought into writing discussion questions, bringing snacks, and securing a room. When the time came for people to arrive, she began to watch the clock. As the minutes continued to pass, she came to the realization that no one was coming. Of course, Courtney was disappointed, but her unsuccessful event provided a teachable moment.

Jerrid believes that nothing good comes from staying within your comfort zone. That is why when the time came to start his own business, he leaped. Sure, staring into an uncertain future was frightening–especially when he had a family to consider. All the same, Jerrid did not let this fear hold him back even when he was not quite sure how specific bills might be paid. Luckily, Jerrid found success in his measured leap of faith, but he also had to be willing to accept the possibility that he might fail.

“Fear has the potential to prevent them from living a full life and starting entrepreneurial ventures that could positively impact people’s lives”

In his work with students, Jerrid understands why they fear failure. After all, no one wants to disappoint their family, friends, or themselves. However, this fear has the potential to prevent them from living a full life and starting entrepreneurial ventures that could positively impact people’s lives.

When discussing failure, Jerrid looks towards serial social entrepreneurs for inspiration. These business owners have created more than one enterprise and have had some measure of success. Jerrid believes that there must have been failures along the way that served as building blocks for them to be successful. This becomes important for students to know. Failure is indeed a part of the process. As students go on to become part of various professional communities, they can look to successful companies for best practices and how to avoid pitfalls.

“The fear of failure is much scarier than the actual fear. It is human nature to amplify all the bad things that could happen. But what about the awesome things that may happen if you succeed?”

Moral of the story? If you’ve never failed, then you’ve never done anything of great significance.


**Credit: The theme music for Teaching Change is provided by bensound.com.**

Episode 14 – Empathy

What role does empathy play in social entrepreneurship? Is it important that practitioners in this field understand the experiences of those they help? These are the big questions that Jerrid and Courtney tackle in this week’s episode of Teaching Change.

Not to be confused with sympathy, empathy is the ability to feel what others are feeling in a given situation. Empathy diverges from sympathy because while you may understand a person’s perspective, you are not necessarily endorsing or condoning it.

One school of thought in social entrepreneurship is that fostering more empathy in society will lead to more social entrepreneurs. When you are in the business of changing people’s lives for the better, it is paramount that, to some extent, you understand their journeys and can identify why they feel the way they feel. Without empathy, the motivation to solve some of the society’s greatest issues, such as homelessness, income inequality, and drug abuse, may not be as strong.

Still, Jerrid receives mixed reviews when he talks about empathy in his social entrepreneurship class. While some students are receptive and embrace empathy, others are more ambivalent. For these students, empathy is another word for emotional and has no place in business. They believe that social entrepreneurs do not need to feel. They just need to do.

Jerrid and Courtney reflect upon how much empathy plays a role in their jobs and life in general. Jerrid recounted a frustrating experience he had recently when he suffered a tire blowout on his car. As he went to various auto stores to remedy the situation, he was met with an indifference which made a bad situation worse. Luckily, Jerrid continued his search and found someone who understood his frustration. This was the store that ultimately received his business.

“Could a greater miracle take place than for us to look through each other’s eyes for an instant?” – Henry David Thoreau

Sure, empathy is a good practice. Both Jerrid and Courtney agree that it could solve a lot of conflicts that we see in the world today. However, could there ever be too much empathy? Courtney offers up a cautionary tale about an encounter in a Publix parking lot. A stranger approached her and asked her for money to pay for a car repair with the promise to pay it back. At the time, all Courtney could think about was what if the shoe was on the other foot and she needed financial assistance. Courtney gave the stranger the money and never heard from her again. Jerrid counters that it was not empathy that compelled Courtney to give the stranger money. At the point, Courtney modified her behavior and “gave the money to the universe,” sympathy became the motivating factor.

Conversations on empathy in social entrepreneurship often end with how to build it—which is easier said than done. The necessity exists. The ability to empathize broadens people’s perspectives and allows them, metaphorically, to walk a mile in someone else’s shoes. Seeing a social ill from the person’s point of view that it affects the most has the potential to galvanize more people to seek innovative solutions. In essence, it will make the world a better place.


**Credit: The theme music for Teaching Change is provided by bensound.com.**


Episode 13 – Purpose

Teaching Change takes a philosophical turn in this week’s episode when Jerrid and Courtney ponder their purpose in life. As educators, they find that this is an area where students have difficulty articulating a clear-cut answer—and so do Jerrid and Courtney! Finding one’s purpose remains an important part of the decisions and careers their students will undertake.

This is also the case in the world of social entrepreneurship where the purpose is a major talking point. Of the two essential components of social entrepreneurship, wealth, and value, value has long been the more complicated one to decipher. In the process of creating social value, social entrepreneurs are changing people’s lives for the better. This type of value creation is often closely tied to their missions in life. Therefore, when social entrepreneurs are presenting their ideas and talking about their organizations, the conversations are often framed by purpose.

“Efforts and courage are not enough without purpose and direction” – John F. Kennedy

Jerrid’s ultimate purpose is to leave the world better than he found it. However, for him, the tangibles of this purpose continue to evolve and can take on many shapes and forms. Jerrid recounts how he started to put his purpose into action in the music field where he helped up and coming bands put on concerts. The gratification he experienced from this morphed into his desire to help people on a broader scale.

Courtney’s purpose stems from her determination to savor life and to enjoy every moment. Lifelong learning is an important part of this. She wants to improve and broaden her horizons each day because life is way too short. In doing so, she motivates others to do the same.

“Education’s purpose is to replace an empty mind with an open one” – Malcolm Forbes

Is following one’s purpose selfish or selfless? Or is it a little bit of both? One of Courtney’s pieces of advice for students is to be selfish in their studies. If they find a way to make each assignment about themselves, they will be more motivated and interested in completing their work. The same could be said of social entrepreneurs. If their own life’s purpose drives their work and business practices, they are likely to be more invested in the success and prosperity of their organizations.  


**Credit: The theme music for Teaching Change is provided by bensound.com.**


Episode 12 – Benefit Corporations (B-Corps)


In this episode, Jerrid and Courtney discuss Benefit Corporations, also known as B Corps. To obtain a B Corp certification, organizations must adhere to a set of guiding principles that involve the betterment of people and the planet. This process may also include site visits.  Another component of becoming a B Corp deals with legal status. As is the case with other business classifications, registering as a B Corp may impact taxation rates.

Although a worthy certification, many people outside of the social justice and social entrepreneurial fields may not know about B Corps. However, as consumers, having this awareness could help people make more informed decisions about which businesses to the patron. Take a coffee shop for instance. Customers may decide to choose Coffee Shop A over Coffee Shop B if they discovered that Coffee Shop A paid its employees a livable wage and operated sustainably.   

B Corps are still in the business of making money—they would not be able to survive otherwise. They just earn profits in a way that gives more than they take. In doing so, this philosophy encourages organizations to have larger conversations within their internal ecosystems and with shareholders. All the same, not every social enterprise has gone the B Corp route. Reasons include not seeing the value, not being able to afford it, or simply not qualifying.

In the Central Florida area, examples of B Corps include Clean the World, Downtown Credo, and Ten Thousand Villages. Some B Corps may identify themselves to consumers with a sign on the door or next to the cash register. Information of this type is becoming increasingly important to consumers as they use their money to support various causes.

Teaching Change Shout-outs
For more information on topics discussed during the show, see the list below.

What are B Corps?

Clean the World

Downtown Credo

Ten Thousand Villages

**Credit: The theme music for Teaching Change is provided by bensound.com.**


Episode 11 – Moment of Obligation


Join Jerrid and Courtney for a walk down memory lane as they discuss their personal moments of obligation. In social entrepreneurship, the moment of obligation is when social entrepreneurs realize they have to make a change in their own lives or others for the greater good. However, as is evident in the episode, such realizations occur in many different fields and circumstances.

For Jerrid, his moment of obligation came in the form of one of his students. Several years ago, he chaperoned a class of college students on a service learning trip to Immokalee, FL. Immokalee is a rural, farm community that primarily grows tomatoes. Many of its citizens are immigrants and are among the working poor. Jerrid and his students were there to volunteer at a homeless shelter.

Late in the day, Jerrid discovered that the parents of one of the students had been frantically trying to reach her. She had not returned their calls because she felt her parents would not approve of the trip. They were not the type of family that worked for free. In spite of her family’s values, this student went on to become a valuable leader in the service program—all without the knowledge of her parents.

This encounter left a profound impact on Jerrid—even if he did not know it at the time. This is the case with many moments of obligation. Seeds are planted along the way until the feeling or thought of change is crystallized. Therefore, many moments of obligation are years in the making. As Jerrid continued his work, it troubled him that the student thought her wishes to better society and her parents’ philosophy of work were so at odds. Through his work with social entrepreneurship, Jerrid realized that common ground was attainable. He has discovered a multitude of ways that people can have a profitable, beneficial life and still better society.

Courtney’s moment of obligation stemmed largely from her upbringing and a short stint as a middle school language arts teacher. While she lived comfortably as a teenager, there were some amenities her family could not afford. There were no computers and, by default, no Internet in her household. This lack of access to a powerful resource served as a building block for Courtney’s moment of obligation. Reflecting on her own background, she realized that everyone does not begin at the same starting line. Through her work at the library and as a champion of lifelong learning, she is able to direct people to resources that may give them a head start.

As was the case with Jerrid, one of Courtney’s students also left an indelible mark on her life’s work. As a middle school teacher, Courtney enjoyed taking the journey with her students as they met their academic goals. One memorable student was the class clown who was frequently absent and did poorly on assignments. Courtney and the student would talk after class about his goals and what he wanted from life. Sadly, the student eventually failed her class and had to repeat the grade. The following year, the student came back for a visit and thanked her. He told her he had been listening to their conversations and he was determined to make something of his life. Courtney often looks back at this moment as motivation to listen to people’s stories and to understand everyone has their own unique paths.

**Credit: The theme music for Teaching Change is provided by bensound.com.**


Episode 10 – Interview with a Founding Faculty of The First 30 Social Entrepreneurship Program and Disability Rights Activist Crystal Smith


Mums the word this week on Teaching Change as the hosts interview Professor of English, disability rights advocate, and secret-keeper extraordinaire Crystal Smith.  For Crystal, Valencia College was supposed to be a temporary detour along her journey through life. However, Valencia quickly became a destination when Crystal connected with her students, her peers, and the campus culture.

Crystal plays a unique role in the college’s social entrepreneurship program. She, along with Teaching Change host Jerrid Kalakay, are participants in Valencia’s First 30 course offerings where faculty team teach a group of students using a common theme. Last year’s theme was social entrepreneurship. Crystal felt this was the perfect marriage of the social justice ideas explored in her composition class with the economics and sustainability inherent to social entrepreneurship.

Crystal is also an active member of Valencia’s Peace and Justice Institute. She has taught workshops for Peace and Justice week. One of these workshops focused on the power of love letters to transform and heal. Participants wrote letters of encouragement to strangers and penned the missives on a designated tree. This past year’s theme was letters to the world where students expressed thoughts on news events such as the Syrian refugees and the Pulse tragedy.   

For Crystal, teaching is a deeply personal experience for both her and her students. “The curriculum comes in the room when the students do,” says Crystal. The first essay prompt she gives her students is “tell a story only you can tell.” The intimate nature of the responding narratives often moves Crystal to tears as she reads stories of abuse, hunger, and trauma. These papers are deeply private and Crystal holds them in confidence as the ultimate secret keeper. This assignment builds a relationship with her students and paves the way for community building in the classroom.

Crystal identifies herself as both learning disabled and physically impaired, both of which she readily shares with her students. For Crystal, the disclosure is empowering and models self-acceptance to those who may face challenges in their own lives. The first time Crystal articulated living with a disability was through a college essay when she applied to Stetson University. This proved to be a major stepping stone to the advocacy she practices today. Crystal encourages everyone to embrace their personal power and to claim their personal identity as she did all those years ago.


Crystal Smith’s Biography

Crystal Smith is a professor of English with a bachelors and a masters degrees in English as well as an additional bachelors degree in American Studies focused on American sub-cultures.  In 2005, her work in American Studies and disability awareness campus activism at Stetson University led to her winning multiple awards, including the Dian Christensen Award for Community Activism. Her dissertation in language and literature and continued scholastic interest was on the role of disability, embodiment, and femininity in the literature of Flannery O’Connor. As a professor, Crystal’s interests include social entrepreneurship, and she was on Valencia College’s first team of faculty that developed social entrepreneurship into a meta-major pathway. With regard to disability activism at Valencia College, in 2016, Crystal served on Valencia College’s Accessibility Advisory Group, which is a sub-committee of Valencia College’s Faculty Association.


Teaching Change Shout-outs
For more information on topics discussed during the show, see the list below.

First 30

The World Needs More Love Letters

Peace and Justice Programs


**Credit: The theme music for Teaching Change is provided by bensound.com.**


Episode 9 – Interview with Director of Sustainability for the City of Orlando and Co-Founder of IDEAS for Us Chris Castro Part 2

Episode 8 – Interview with Director of Sustainability for the City of Orlando and Co-Founder of IDEAS for Us Chris Castro Part 1


The surf’s up for this episode of Teaching Change! In this two-parter, the hosts talk chasing waves and sustainability with Chris Castro, the Director of Sustainability for the City of Orlando. Chris’ love of nature started at an early age in Miami, FL where he worked on his stepfather’s palm tree farm. His extracurricular activities included snorkeling, scuba diving, and surfing–which was a major reason why he chose to attend the University of Central Florida (UCF) as an undergraduate. Orlando’s location gave Chris easy access to Florida’s exciting beaches and waterways.

Chris may have come for the surfing but he quickly found himself at home among Orlando’s emerging innovation and technology scene. Within these budding platforms, Chris saw the potential for initiatives involving sustainability. Chris’ path to his current advocacy and life’s work is a testament to the power of higher education and the personal development it affords. When asked about his interest in sustainability, Chris recalls the course in Environmental Sociology he took as a student at UCF. He credits this class with opening his eyes on how humans impact the world and each other with actions such as energy consumption and waste. These revelations sparked his interest in sustainability activism and in solutions to issues that plague the environment. That’s when Chris went mobile.

He rallied his peers together and formed IDEAS for Us, which began in 2008 as a UCF interdisciplinary organization of students working on policy and solutions to make college campuses more sustainable. Now IDEAS for Us has chapters all over the world, including one at Valencia College. The focus of IDEAS for Us revolves around energy, water, food, waste, and ecology. Two initiatives spearheaded by IDEAS for Us include Kill-A-Watt and Green Your Game. For Kill-A-Watt, students living in dorms compete to conserve energy and save money to win scholarships. Green Your Game promotes recycling, reducing, and reusing efforts at UCF’s tailgating events.

The conversation then turns to Chris’ work as an urban farmer and the importance of creating a sustainable agricultural system. Chris shares that food currently travels an average of 1500-1800 miles before it reaches a person’s plate. To address this issue, Chris co-created the Fleet Farming program that converts lawns and underused land into farms. Fleet Farming is made possible through Swarm Rides which consist of volunteers on bikes collecting the city-grown produce. The produce is then sold at farmers markets and to local vendors.

Chris wears many hats in addition to his day job. This episode just scratches the surface. Be sure to check back next week to hear the conclusion of Chris Castro’s interview.

Chris Castro’s Biography

(Per LinkedIn)

An award-winning sustainability professional, eco-entrepreneur, urban farmer, and community organizer working to accelerate the transition to a smart, resilient, and sustainable future.

Chris is currently the Director of Sustainability, Senior Advisor to Mayor Dyer, and Co-chair of Smart Cities for the City of Orlando, developing partnerships, policies, and programs to support the sustainability, clean energy, & climate-related goals of Mayor Buddy Dyer’s Green Works Orlando initiative.

In 2008, Chris co-founded IDEAS For Us, a global 501c3 non-profit & UN-accredited NGO, working to incubate global environmental solutions and fund local action that advances the UN Sustainable Development Goals. In 2013, he helped co-create Fleet Farming, a renowned urban farming program that is refining local food by building distributed organic agricultural systems through neighborhoods and communities.

Chris has held sustainability & energy-related positions with University of Central Florida, Orange County Government, and the US Department of Energy. In 2012, Chris also co-founded a clean energy consulting firm, Citizen Energy, that provides custom energy efficiency & renewable energy solutions for commercial buildings in the Washington DC Metro area.

In addition, Chris is a public speaker and has been recognized for his effort as an emerging environmental leader; including the ‘Guru of Green’ by the Orlando Business Journal, the 2017 Grist 50 Award, Top 30 Under 30 sustainability professionals by GreenBiz, formal recognition from President Bill Clinton, and a ‘Champions of Change’ awardee from the U.S. White House & Obama Administration. Chris has spoken at more than 100 conferences and events, including the United Nations HQ & the UN Rio+20 Summit, NASA Kennedy Space Center Innovation Expo, TEDx Orlando, Better Buildings Summit, and more.


Teaching Change Shout-outs
For more information on topics discussed during the show, see the list below.

Fleet Farming

Green Works Orlando

IDEAS for Us


**Credit: The theme music for Teaching Change is provided by bensound.com.**