Ryan Smith is now on his third startup and has already raised $51M in equity and $250 in debt to take on one of the most regulated and fastest-growing industries in America.
During our interview on the DealMakers podcast, Ryan talked about how he got his early start in entrepreneurship, the strategies he’s implemented in order to build a successful marketplace, and his outlook for the future of LeafLink and the cannabis industry.
Growing Up In New York
NYC is famous for its fast-paced energy and being a big hub for business; Ryan G. Smith is among the few who were born and raised there.
His parents were both entrepreneurs in the real estate space. Family dinners in the Smith house involved a lot of discussion around business and the challenges of entrepreneurship.
He spent his youth traveling and holds dual citizenship in Italy. Growing up in Manhattan next to the United Nations, he heard new languages on every floor of his building and was fascinated by the diverse culture around him.
When Ryan first arrived at college, his university had set a goal of becoming CO2 emission neutral. So, he and a friend seized the opportunity to help by starting their own company at school. They began importing tree-free paper. Dorm rooms became warehouses for masses of paper, and 18 wheelers would drop off pallets of inventory.
It was a great early experience in managing all of the working parts of a business. Most of all he says he learned the importance of execution and why it’s essential to take action, rather than sitting around to think about problems he sees. He says this is one of the most vital lessons for new entrepreneurs – you’ve just got to jump in and tackle the next step.
Upon graduating, they sold this business and put it into the hands of a new cohort of college students.
From Start To Exit In Just 18 Months
After school, Ryan was quick to jump on a new business opportunity. He had long witnessed the inefficiencies of the antiquated real estate industry, and at the time, was hearing a lot of buzz about the new JOBS Act.
He decided to dive in and modernize the industry with new technology and built a software platform for helping GPs to manage their LPs online.
Then, just 18 months after starting out, a sales meeting with a large publicly traded fund turned into an acquisition offer.
Looking for a new business to tackle, Ryan leaned into his love for marketplace businesses.
During his childhood, it was a household joke that if something went missing, Ryan had probably sold it online and banked the money into his Paypal account. He teamed up with co-founder Zach Silverman, who had spent some time at eBay, and began looking into how B2B marketplace dynamics could create efficiencies for different industries.
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