1/2 of the former Airbnb duo enabling quick, seamless monetization of investment property.
Role: Co-founder, CEO
How did you meet Tom & how do you complement each other?
We worked together at HotelTonight. We were on different teams but had collaborated a bit and I’d always thought he was really smart and saw him as a hustler – he was alway teaching himself new things. He actually ended up leaving HotelTonight, moving to Span, and joining a coding bootcamp to learn how to become a software engineer. A few months later, I bumped into him making coffee and found out that he was just hired by our CTO as a full stack software engineer – turns out I wasn’t the only one who thought he was brilliant.
We grabbed lunch one day about a year and half ago. Then we started doing a weekly dinner. We met pretty religiously for almost a year. At those dinners we talked about startups, company building, our own ideas - what we thought would work, what we thought wouldn’t work. We must have kicked the tires on 50 ideas over the course of a year until we landed on Topkey.
In terms of complementing each other we both have a fair amount of left and right brain compatibility, Tom thinks in a much more methodological, structured way – he has a true engineer’s mind. He’s brilliant when it comes to sequencing work, processes and operations. He also has a strong creative eye, particularly in design.
I used to be an investment banker, so I’m comfortable getting in the weeds with data, numbers and details. I love building relationships and connecting people and ideas, so I was naturally comfortable managing partnerships with third party companies. I also work to sell Topkey to homeowners and suppliers. Finally, I enjoy writing, so I focus a lot of my time on crafting decks, website copy, and other materials.
How do you feel you've grown personally in building Topkey?
What comes to mind off the bat is becoming better at prioritizing around our primary objectives. Building Topkey has pushed us to become more focused, both personally and professionally. While we obviously have support from our investors, like Y Combinator, it's ultimately on us to set the bar for the team and to hold ourselves accountable.
We’ve also become significantly better at soliciting feedback. Specifically, asking the right questions and identifying the right people to pose those questions to. Everyone has an opinion when you’re building a consumer product company. You can’t ignore it all, but you have to be careful about over-optimizing for any one piece of advice. Getting lots of input can be both a blessing and a curse, so you just have to be careful! On that note, I recently read the Mom Test, an awesome little book that has helped me really hone in on how to get input from customers. I highly recommend it!
Is there a specific source of inspiration that keeps you pushing through tougher moments?
We’ve both worked at companies where users truly loved the products. Starwood Hotels built one of the great hotel brands of our time. HotelTonight had a huge cult following and was loved for its simplicity and ease-of-use. Our motto at HotelTonight was to surprise and delight our customers, and I think there’s a lot of wisdom in that mandate. Airbnb is on another level…. It’s arguably one of the most successful consumer brands to have been created in the last 20 years. You know you’re doing something right anytime your brand becomes a verb!
There’s something about working in those types of environments - where your company provides a service that people really love - that is so contagious. When a consumer product really clicks, you can feel it, you can see it. That’s what we’re pushing for with our business, to really build something that makes people's lives better.
What was it like to get into YC and what were your biggest takeaways?
We were honored and excited. Excited for the opportunities that YC would provide for Topkey’s growth. Encouraged that the partners at YC saw the same potential for our business that we did.
YC is an incredible network to connect you with some of the smartest people in the startup game. I’ve worked with amazing people and have been a part of some incredible organizations, but the network that YC offers is like no other. It’s truly world-class.
My biggest takeaway from YC is to focus on your customer. There’s a reason that “talk to customers” is the most repeated advice throughout the batch. Most companies fail to do this and ultimately lose their way.
My other takeaway from YC is to remember that you have to put in the work. Startups = growth. YC can’t grow your company for you. Only you can do that. It’s not like you get accepted into YC and then receive the secret codes to becoming a multi-billion dollar company. YC can give you tools to help answer some of your most pressing questions, but they certainly can’t ensure your success. The same goes for any of your investors - angels or VC funds. You have to do the work to build the business.
What has been your biggest misstep so far and what did you learn from that moment?
I think there have been times early on when we’ve overcomplicated things. This can become even harder to avoid when you’re deep into the weeds on a given problem. Since we started up in January, I think there have been times we’ve tried to spread ourselves too thin and boil the ocean, when we would have been better served by focusing more on one specific challenge. This carries over into our marketing, our messaging, and how we convey our core value propositions.
One example of how we overcame this was when we started talking to investors and putting our pitch deck together. After a few weeks, we realized the message was too complicated. We went back to the drawing board to rework our deck. Tom spearheaded this effort and was incredibly helpful honing in the message. He really helped me better articulate our core value proposition. We both got much more clarity on the long-term vision for our company.
What’s a song or album that’s gotten you through 2020?
According to my Spotify account, I only added 20 songs to my playlists throughout the entirety of 2020... so I’m probably not the best person to ask! Lately, I’ve been listening to a lot of Motown. Temptations, Wilson Pickett, Percy Sledge, Etta James. The Band also made my top 20. I also have some Daniel Caesar, Jacob Collier, Rick Ross and Brad Paisley. That’s some good range!