How did you decide to found Crosscut?
Between Intermix Media (MIX) and Adknowledge, I raised money from TCV, TPG, Redpoint, Vantage Point, JMI, Nokia and more… but I never even thought about raising from a venture firm based in LA. Based on that experience, it felt like there must be an opportunity to “plant the flag in LA” and become the “go-to” LA-based venture firm. By teaming up with Rick and Brian (2 very experienced venture capitalists who know the business well), we were able to launch our proof of concept fund in LA in 2008. We’ve never looked back!
What was the first lesson you learned about business?
One of my first lessons in business was around team building and team dynamics. For the most part, businesses succeed or fail based on leadership and the decisions they make. At Intermix Media, I was obsessed with team building but occasionally I would get so excited about a new category (dating as an example) that I’d be willing to start a new business with a sub-optimal team. It didn’t take long to see that most of our failures (and there were many) stemmed from when I liked the business idea much more than the team I was able to quickly spin up. My focus today is almost completely around the quality of the founding team. Once we make an investment, I immediately help teams figure out the holes and how we can fill them. Lesson learned: it’s all about the quality of the team.
What was your first entrepreneurial endeavor and how did it go?
In 4th grade, I started a business selling high-end pencils with cool erasers to the other kids. It went well until I expanded into 2 other classrooms and tried to scale the business. 2 days later the principal shut down my business.
What have you learned as an entrepreneur?
Through the pencil business, I learned how to deliver a good product (I rode my bike to the other side of town to buy special colored pencils with jumbo easers) and make a big mark up and to run a profitable business. But I also learned that if you push it too far (and get greedy), it can all come crashing down quickly when the principal cracks down on you. I learned to know and understand your limits!
What do you look for in founders?
First and foremost, fire in their belly to succeed in their quest to change the world. The startup journey is on a tough road that’s littered with broken dreams. As we’ve all learned, founders have to be prepared to pivot, restart, expect with the unexpected, and make tough choices quickly...all in the same week! It’s not for the faint of heart, but after doing this for 20 years, you can spot the fire (and desire) from a mile away (or not).
Why have you completely avoided being on social media yourself?
People often get a kick of this given my Myspace roots and all, but the truth is that I have never been a “social media” person. From early 2003 and the launch of Myspace, I have been fascinated with watching the way people interact with social media and the way it has shifted human behavior. But I have always been content watching as an amateur social scientist from the outside. I don’t see that changing soon, and for the most part, I think people need to spend less time on their phones and more time talking to each other!