Today I had the pleasure of interviewing Ryan Smith, CEO of LeafLink.

What is your “backstory”?

I was born with the entrepreneurial spirit. In my Catholic grammar school, we weren’t allowed to bring candy to lunch, so in 3rd grade my friends and I bought candy at the corner deli and would sell it for double the retail price during recess. I got caught splitting up the $50 in cash profits with my group of five friends when a nun walked by and wanted to know what was going on. From there, I became obsessed with online marketplaces and created my first eBay account in 6th grade. The joke growing up was that if something went missing, it was probably in Ryan’s PayPal account. Fun fact, I have over 300 positive reviews on eBay since then; I’ve even sold a single shoe.

That passion only grew and so while I was an undergrad at Colgate, I started two companies. One was a paper supply company that became a legacy business for other students when I sold it in senior year. The second was an investor relationship platform for real estate companies, which I later sold to an NYSE public firm that had over a quarter-million investors at the time.

I met Zach, LeafLink’s co-founder, through mutual mentors and investors. I vividly recall having coffee with him in Grand Central Station, brainstorming given our mutual experience in B2B marketplaces and SaaS; at the time, Zach was at eBay. So, I said to him, “I keep hearing a lot about the cannabis industry…” and he banged his hands on the table and said “Yes!” That’s when we started mapping out the initial plans for LeafLink. After that, we booked a flight to Denver and started shadowing cannabis companies together, learning how we could help solve their pain points and define their operations with LeafLink.

Can you share the funniest or most interesting story that occurred to you in the course of your career?

When we first began doing research in the cannabis industry, we met with a leading cannabis brand and were asking them a series of questions to better understand their business. At the time they were doing eight figures in annual revenue. I remember asking them, “so what was your most sold product yesterday?” and their answer was “well, I think it is one of the fruity drinks.” It was a subjective answer, data-naked, to a very objective question — and that’s when a light went off for Zach and me. We knew we could build an online system to help institute processes and empower other entrepreneurs.

Are you working on any meaningful non-profit projects? How have you used your success to bring goodness to the world?

I enjoy giving back by participating in Colgate alumni events, whether it’s speaking or mentoring students from the university. I started my first two companies in college, and the same Colgate advisors who helped me then later became some of our first angel investors in LeafLink. Their mentorship has been monumental in my journey as a young entrepreneur, and I want to pay that forward.

Can you tell me a story about a person who was impacted by your cause?

I was recently at lunch with a client of ours who moved from Colorado, where we launched LeafLink last year, to another state where the cannabis industry is just starting up. I asked why he moved, and he told me that he loves the chaos and excitement of an early market — but that Colorado had become mature and refined, largely because of LeafLink. That was a “wow” moment for me, because it’s proof that LeafLink is truly defining and scaling this industry.

What are 5 things you wish someone had told you when you first started out and why?

  1. Execution is everything. We have seen a number of companies over the last two years pop up at conferences, make a lot of noise, and then hear nothing about them in the field. Talk is always cheap and in business, dangerous.
  2. It’s good to say “No.” Sometimes in negotiations, agreeing to what the other side wants can just delay the close.
  3. Don’t spend too much time watching competitors. Don’t stress about the competition you know. At LeafLink, we are always planning for and arming ourselves to combat the competition we don’t yet know.
  4. Awesome team required. As LeafLink continues to grow, it is incredibly important to us to welcome team members who are experientially diverse. By partnering individuals with great cannabis experience and those with exceptional technological acumen, we can usher in a brighter future for our clients and the industry.
  5. Don’t be afraid to hire people who are better at something than you are. Stay humble when hiring. This was true for our first hire, Claire Moloney — we didn’t exactly know what her role would be when we hired her, but we knew she understood marketing and operations at a scrappy startup better than Zach and me. That same approach of bringing in people that know more and can truly own what they do, drives our team-building at LeafLink.

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why?

Antoni Gaudí, if he was still alive. Gaudí designed a number of inspiring structures, mostly in Catalan, that were so groundbreaking and with which he was so obsessed that he often lived in the basement of their construction sites. His designs and calculations were so complex that when his studio burned to the ground after his death, it took NASA engineers years to figure out how to build the designs he’d already engineered. Gaudí always impressed me as a person to emulate with one goal: create in reality what’s constantly on your mind.