Katlyn Grasso on Entrepreneurship and Swimming Upstream

Katlyn Grasso is the CEO and founder of GenHERation, a startup that connects young women to companies through nationwide events and a digital platform. During her time at the University of Pennsylvania, from which she graduated in 2015, Katlyn was one of the inaugural recipients of the President’s Engagement Prize, which awards $150,000 to graduating seniors to develop innovative projects with a social impact focus. Her other accomplishments include being selected to participate in the 2015 Millennial Trains Project, a cross country trip for social innovators from around the world to connect and build out their ideas. At Penn, Katlyn took advantage of several entrepreneurship resources to help her grow GenHERation. Read her interview below to learn more.

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Stories worth noting:

1) Balancing entrepreneurship and full-time studies at Wharton
2) Becoming a better entrepreneur by meeting new people every day
3) Katlyn's advice about "swimming upstream" to be successful
4) Common misconceptions about being an entrepreneur

You worked on GenHERation for most of your time at Penn. How did you balance that with your studies at Wharton?

Being an entrepreneur requires a certain set of skills, including persistence, determination, and resilience. It’s something that is tied to your identity and it is certainly not a 9-to-5 job. It’s a 24/7 mentality for me. College is the best time to be an entrepreneur because there is an abundance of resources available for students. There are business plan competitions, grants, research stipends, and fellowships. There are many people who want to help student entrepreneurs succeed and student founders are tasked with finding the best way to navigate the entrepreneurial ecosystem.

One issue I see is a lot of people have ideas but it’s hard to decide whether it’s worth taking on full-time or to keep it as just a side project. What convinced you to pursue GenHERation full-time?

At the end of my junior summer, before the President’s Engagement Prize was announced, I knew I was going to be an entrepreneur full-time after graduation. I received the Wharton Venture Award, which provides $10,000 to rising seniors or second year MBAs to pursue their own venture the summer before their last year of school. At the end of that summer, we had hosted a five-city Summer Leadership Series and grew from 200 to 5,000 users. I thought if we could achieve these milestones during a three-month period, imagine what we could do when we’re working on the startup full time!

Let’s shift to the Millennial Trains Project you were in while still in school. The premise is so unique — tell us about it.

The Millennial Trains Project (MTP) was a transformational experience. MTP is a cross-country train trip for millennial leaders working to advance social impact projects around the world. My cohort traveled from Los Angeles to Washington, D.C. over the course of ten days while visiting historical landmarks along the way. The participants on the train were some of the most inspiring people I have ever met and continue to be an active group of change-makers. The Millennial Trains Project helped me recognize the power of travel and its ability to create new communities.

How did you first hear about the Millennial Trains Project?

I was at a demo day for Wharton Entrepreneurship in the spring of 2015 and the leaders of Comcast’s Entrepreneurial Engagement team were in the audience. Comcast-NBCUniversal was the sponsor of the Millennial Trains Project and was looking to send an entrepreneur to represent the city of Philadelphia. I met with the team at Comcast the week after demo day and they asked me if I wanted to participate in the Millennial Trains Project. The trip started a week later, two days after graduation.

I love how this huge experience came out of one chance encounter — it’s so spontaneous! How can students get themselves more out there at school?

When I was a sophomore, a female entrepreneur told me I should talk to someone new every day, so I started talking to everyone and anyone I could. I talked to a diverse group of individuals ranging from professors to government leaders to business executives to university administrators. You can learn something from everyone you meet and it is an entrepreneur’s job to build a community of experts. Meeting new people every day is my favorite part of being an entrepreneur.

Who were those people or communities for you at Penn?

Penn has a vibrant entrepreneurial community that consists of many support systems, including Penn Wharton Entrepreneurship, the Wharton Small Business Development Center, the Wharton Innovation Fund, the Baker Retailing Center, the Wharton Social Impact Initiative, the Detkin Intellectual Property & Technology Legal Clinic, and the Entrepreneurship Legal Clinic. Every student entrepreneur needs to develop a roadmap that best suits her needs.

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For students who want to pursue social impact or entrepreneurship but may be disillusioned by how hard it is, what’s your advice to them to keep going?

I always say you need to swim upstream to be successful. While everyone is swimming in one direction and pursuing a common goal, you need to swim in the opposite direction. A mentor at the Wharton Small Business Development Center once told me to make sure that you always know your end goal and pursue opportunities that put you on the path to accomplishing that goal. If you don’t feel comfortable enough jumping in and being a full-time entrepreneur right away, you can identify the next best steps that will guide you along your startup journey. First, you should work in an industry that you are passionate about and will allow you to strengthen your expertise in a given field. Next, you can try working for an organization that mimics the environment of an early stage company, such as a startup accelerator, to learn the ins and outs of the business. Alternatively, you can also join a startup that has a more established team of about 200–300 people so you can learn gradually in a collaborative setting.

A lot of people who love social impact or entrepreneurship take the safe route first, hoping to come back afterwards. But they don’t realize how much harder it is to make that 180-degree pivot after being so comfortable those two years. Any founder will tell you that there is not a specific class or job that will prepare you directly for your current venture. The only way to learn is to jump in and “just do it,” as Phil Knight, the founder of Nike, would say.

Discomfort is the impetus of growth and once you become comfortable, it is time to start doing something new.

That’s a good rule of thumb. Two years is definitely not something to casually spend. You grew from 200 users that summer to 75,000 users now in just two years!

In the startup world, a month can seem like a lifetime because everything moves so quickly. Every day counts when you are building a company and every task is pursued with a sense of urgency. As long as you are learning and growing from your work, it will provide you with valuable experience you can apply to any profession.

What are the biggest misconceptions about being an entrepreneur?

I think that people perceive being an entrepreneur to be a lot more glamorous than it really is. When we are on the road over the summer, my team and I work 20-hour days across three different time zones. Successful companies are not built over night; it requires an unwavering commitment to building something you truly believe in. If you like living in a state of constant change, being an entrepreneur will provide you with a fun and fulfilling career.

Lastly, what are your favorite books or pieces of media?

I love reading the autobiographies of successful entrepreneurs. My current favorites are Shoe Dog by Phil Knight, the founder of Nike, and It Takes a Tribe: Building the Tough Mudder Movement, by Will Dean, the founder of Tough Mudder.

Laura Gao

Aspiring designer, entrepreneur, writer and everything in between.

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