Humans of Lob is a project dedicated to getting to know our Lobsters on an individual level. We sat down with our COO, Ryan.
Let's start with your childhood. Tell us a little bit about your upbringing and your family.
I grew up outside of Philadelphia, I have a younger sister and brother and we grew up primarily with just my mother at home. I played a ton of sports - soccer, basketball, and track.
I’ve lived in California for almost 20 years, but growing up in Philadelphia was very different. I would say that folks on the east coast are more direct; they share what's on their minds and are not afraid of confrontation.
I’m still a Philadelphia sports nut to this day. My son, who’s grown up in California and loves baseball, had to confess to me recently that he’s more of a Giants fan than a Phillies fan. It was almost like he was asking for my permission!
Tell us about your early career, and how that influences you today.
After college, I moved to the Bay Area because I was doing social work. I worked in Oakland at a drug rehab and youth center. During that time, I realized that I was good at connecting with people and making friends, but I was not cut out for social work.
After three years of social work, I was trying to figure out what to do with my life and considering moving back to the East Coast. Then, serendipitously, I met an engineer who was working at NASA and was visiting the Bay Area because he was just about to join this startup called PowerSet. It was a natural language search engine started by a bunch of former folks at NASA.
He told me his boss was looking for someone to help around the office as an admin assistant. So I went down to Palo Alto to this startup incubator. I remember feeling like I was in the future! Everyone was dressed super casually for work, and they had these silver MacBook Pros that had just come out.
I walked up wearing a tie and jacket, and the COO looked at me like, “what are you wearing”? I fumbled through the interview and convinced him I would do anything to get the job. I started as his admin assistant, and eventually, he hired me to be his Executive Assistant.
That role completely changed my life. I had no idea about technology, natural language search, or anything. But little did I know, this business was one of the next hot startups, and I got to join as employee number six.
I attached myself to the COO, Steve, and watched everything he was doing for two years. I moved into business operations and did some HR.
Fast forward two years later, PowerSet was acquired by Microsoft, and as that was happening, two of my co-workers came to me and said, ‘we're starting a gaming company on Facebook.’
They were like, ‘yo, let's not go to Microsoft, let's start our own thing.’ And I joined them to start Serious Business. We were some of the earliest app developers on Facebook. Definitely the right place at the right time.
We raised venture financing from Lightspeed Venture Partners and quickly grew the business to about 50-60 employees. Then two years later, Zynga, a large maker of social games, acquired that business as a part of their IPO roll-up.
It was this whirlwind experience of going from not knowing anything about technology to being in the middle and having to learn quickly. There couldn't have been a better business class. Since then, I've been doing startups and growth stage companies for the last 15 years.
I was really fortunate; the best opportunities are connected to people. If you surround yourself with the right people, they tend to find their way to the right opportunities.
Is there something about yourself that you think somebody new would be surprised to learn?
I do a lot of yoga and am a personal development junkie! I spent about a decade trying to read every self-help, personal development, and business book I could get my hands on. I've since been trying to implement those systems and strategies at Lob.
Now I spend time reading books and biographies that analyze the state of the world and what the world might look like in the future. Whether it's Churchill or Rick Ross, I like hearing people's personal stories of how they evolved, how they grew, and, more recently, how that impacts the world and events.
I want to connect the head and the heart, especially in business. You can have the best business, the right models, and metrics, but if you don't have people's hearts bought into a larger cause, you're not going to achieve those goals.
Who is the most influential person in your life?
It's easily my mother. I couldn't think of somebody more committed or unconditionally loving. My mom is someone who just lives with her heart. She's really direct, but at the end of the day, she truly, genuinely loves people.
Growing up, I watched her own and operate her own small business - a cleaning service. Watching her problem-solve and hustle was really impressive to me. In the summers, she used to say, "Hey Ryan, I need to clean a house quickly, do you want to come with me and help?" I would go, and it would turn into an all-day affair. Obviously, it was the least I could do, but I dreaded it on summer break. In hindsight, though, I realize why it made my mom such a great business owner and why these people would pay her a mint to clean their houses.
I learned so much, from when she launched the business to getting the word out, particularly watching her find her ideal customer. She had a real knack for connecting with elderly people. She established a smaller cohort of elderly customers who were as interested in spending 20 minutes talking to her and catching up with her as they were in getting their houses cleaned. She was creating that relational connection; she was providing a service beyond just the transaction of cleaning.
Do you have any unique or important mementos you hold on to?
I'm a novice collector, but I don’t have memorabilia. I collect sample postcards and letters from our key customers. I have an overflowing box of the different mail pieces I've collected from senders Lob works with. One day maybe I'll have a canvas made of the best mailings during my time at Lob.
What does your perfect weekend look like?
It sounds crazy, but I get to live my perfect weekend on many, many weekends. My wife and I've been really intentional about crafting our weekend time.
My perfect weekend looks like this: Friday night, I get sushi with my wife, Fiona, at this one place in Alameda. Then we pick up the kids. In the evening, we watch a movie or just do something together as a family.
I wake up a bit earlier to have a little alone time on Saturday, then spend the entire day doing kids' stuff. Maybe we go to food trucks in Alameda for lunch and then have dinner with friends who have kids that are also friends with our kids! Every three weeks, my two sons and I get a haircut together. It's kind of our bonding time, so we roll up at Supercuts, and they're eating lollipops, and we're hanging out having our dude time together. Then we will bring home a quick breakfast from Starbucks to Fiona. She's probably cooked scallion pancakes, a Taiwanese specialty my boys love.
Sunday, we get a little bit of quiet time in the morning. We do church (usually online since COVID), and as soon as that's over, we take the kids to their Ayi’s house (Chinese for Auntie). Fiona and I have Sunday afternoons as our time together. It doesn't need to be anything elaborate - often, it's cleaning the house or getting things done together. Fiona's got me into getting pedicures as a treat-yourself type thing. We'll definitely go to something like that or a nicer meal. Then we pick up the kids in the evening, do family time, and feel ready for the week.
What's one of your favorite memories from the past year?
My oldest son got really into baseball. So I took him to a Giant’s game, and he had the bug. Now he wants to visit every baseball stadium in the major leagues. We've been to six or seven at this point.
My favorite memories from the summer are of us going to Camden Yards in Baltimore, Citizens Bank Park in Philadelphia, and T-Mobile Park in Seattle. Just getting to go to those games together has been so special.
But I told him we'd hit every stadium, and I'm thinking by the time he’s out of high school, we'll have gone to every stadium, right? This summer, we traveled a bit, and when we got home, I mentioned that baseball season was almost over. He just breaks down crying. I ask him what’s wrong, and he says, "we haven't visited every stadium yet." I was shocked! I hadn’t given him a timeline, so he thought it would happen before the season’s over, haha!
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