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Ava Pipitone | Baltimore | First Domino!!!

From farm to city to community, I grew up lifting hay bails on a horse farm, then I relocated to NYC. Later I left the country for 3 years. Everywhere I went I encountered queerness and non-western concepts of gender. Returning back to the States to start a medical transition, I joined a worker-cooperative and helped found a non-profit. After 2 years as Executive Director of the Baltimore Transgender Alliance, we've grown to ten staff members and I've scheduled my exit to focus on HostHome. I'm also exiting Red Emma's Cooperative. I thought my body and my gender meant I could never be successful, let alone build companies. I was wrong. People support transgender leaders. Thriving in a society not built for us, our survival skills and auto-digestive solutions continually mold transgender folks into native innovators. Literally through necessity. I don't know another transgender woman who has not taken in a younger transgender sibling for a few nights in an emergency. We have always done this labor. We have never had our own tool to support and scale these networks of critical support. I was finding housing for the various LGBTQ youth frequenting our cafe two summers ago; reacting to need and building out networks of hosts. When the local non-profits started calling me and my friend's cell phones to house transgender people because the shelters rejected their clients, we knew we had to formalize this solution. With over 70% of transgender people being attacked or worse in shelters, we and our allies understand that we need a community directed approach. HostHome was born as we noticed we were already doing this.

What were the biggest initial hurdles to building your business and how did you overcome them?

Firstly, finding value alignment in funders is uniquely challenging. We have to determine if an investor believes in our merit or is looking to add diversity to their portfolio. They will interact with us differently depending.

Second, maintaining community support when structuring as a benefit corporation instead of a non-profit. Most people believe that non-profits are the only structures that can do good in society. I challenge this and say that, within our current climate of late capitalism, we must have access to all the tools for growth if we truly want our solution to scale to the size of the problem we are facing.

What books are you currently reading? And your recommendation for entrepreneurs to read?

I read speculative Science Fiction mostly by queer black woman authors. So I have been reading Octavia Butler's works and enjoying the engagements with queer, race, and class issues from a 1980s perspective.

For entrepreneurs, I believe knowledge mostly flows from people, so the people you spend time with are more important that what you read. The best productivity hack is actually doing instead of reading about how to do better. Nonetheless, "Raise Capital on Your Own Terms: How to Fund Your Business without Selling Your Soul" by Jenny Kassan was incredibly useful for me to understand how to discover and access the capital already within my social networks.

Did you ever deal with contention from your family and friends concerning your entrepreneurial pursuits? How did you handle it? What would you do differently in hindsight?

Yes. Legitimizing remote work and virtual teams to family and friends who cannot see them is an ongoing challenge. It's only when they read about me in the newspaper do they feel my work is legitimate. Legitimacy with investors is always correlated to metrics. Legitimacy with family and friends meant patience. They caught on after a few fellowship awards and press events. In hindsight, I would have anchored family and friend understanding as less crucial, while their emotional support remained critical. This would have saved me hours of pitching them on the inner workings of the venture, when they are actually concerned with the inner workings of my life. The people who care about you are only looking to do that; don't try to sell them anything or force them to communicate with you in startup jargon. Turn off the work brain when you can.

What would you say was the single most influential factor in your business success?

Domain expertise; I am working to solve a problem that affects me directly. I have been housed in emergencies by other transgender friends and I often house my friends in need. I know how to solve this problem because I've lived all sides of it.

What do you know today that you wish you would have known when you first got started as an entrepreneur?

People will not understand all the decisions you make, make them anyway. Your actions will speak louder than your words ever will. And this will mean that many friends will not get it. Do regardless.

What advice would you give to an upcoming entrepreneur locally and internationally?

The world may not be ready for your vision. Build the first part that catalyses a path towards your vision and let go of all the steps along the way. If you do a good job with that first domino, all will be well.


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