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Paul Holliman
Angel Investor & Startup Advisor
Alumni Profile:

Paul Holliman is an angel investor and startup advisor based in Los Angeles. Prior to focusing full time on angel investing, Paul spent more than 20 years at Walt Disney Studios Motion Pictures, most recently as a Vice President of Sales.

What got you interested in angel investing?

My path was not typical. Most angel investors are former founders, or people managing a family office learning the venture part of things. For me, it wasn’t about investing, it was about learning about technology. I was the head of strategic planning at Disney so I was interested in the future – How fast could things scale? What could possibly disrupt us? I was looking at tech for a different reason. Then I fell in love with entrepreneurship. I started investing, and it became this transformative experience.

How many deals had you done at that point?

I had been investing for a couple years before I started Deal Camp. I was really interested in portfolio theory. For me, that was the path to safety because you can minimize risk dramatically by making a lot of investments. At that point, I had invested in well over 100 startups. 

Why Deal Camp?

Taking Deal Camp was a no brainer. At the time, I was trying to learn as much as possible about venture capital, but there wasn’t that much information out there. There weren’t a lot of books, there was a bit of Kauffman data on portfolio performance in the 90’s, but not a lot to learn from.

Deal Camp was a way to meet other investors and figure out what their strategies were. I got to see a lot of 500’s data and check if my assumptions were correct. I wanted to learn more.

What were your favorite parts of the program?

All of the coursework covering cap tables, convertible notes, liquidation preferences, and the nuances of these documents was really helpful. I don’t think I would have learned that information so succinctly anywhere else. 

The exposure to Demo Day and the role play exercise of negotiating with founders also helped me develop a new mindset. That’s where I first thought, “OK, how am I going to approach interviewing founders?” Funnily enough, I had actually invested beforehand in one of the startups that 500 Startups brought to the program. It turned out to be one of my better investments and I even remembered the terms in class! 

The validation I got from learning about 500’s portfolio theory and diversification was also critical, especially in this asset class. And then there were the relationships. I made so many great friends in the class. I felt like I found my people!

How did Deal Camp impact your confidence as an angel investor?

It definitely impacted my confidence. Before the program, I would wonder, “Am I doing the right thing? Is this the right portfolio theory?” After the program, I had the validation I needed and I knew I was on the right path. The results have been great. I’ve made over 350 angel investments and I have 8 unicorns and only an 8% shutdown. 

What advice do you have for aspiring angel investors who are considering the program? 

I recommend Deal Camp to so many people who are starting out in angel investing. The value for me was validation and making sure I understood the technical details of investing, which can be complicated. The other big takeaway is about the importance of deal flow and the network you build. But you’re only going to get the benefits if you work on those relationships in class. I am still seeing benefits years later. 

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What got you interested in angel investing?

My path was not typical. Most angel investors are former founders, or people managing a family office learning the venture part of things. For me, it wasn’t about investing, it was about learning about technology. I was the head of strategic planning at Disney so I was interested in the future – How fast could things scale? What could possibly disrupt us? I was looking at tech for a different reason. Then I fell in love with entrepreneurship. I started investing, and it became this transformative experience.

How many deals had you done at that point?

I had been investing for a couple years before I started Deal Camp. I was really interested in portfolio theory. For me, that was the path to safety because you can minimize risk dramatically by making a lot of investments. At that point, I had invested in well over 100 startups. 

Why Deal Camp?

Taking Deal Camp was a no brainer. At the time, I was trying to learn as much as possible about venture capital, but there wasn’t that much information out there. There weren’t a lot of books, there was a bit of Kauffman data on portfolio performance in the 90’s, but not a lot to learn from.

Deal Camp was a way to meet other investors and figure out what their strategies were. I got to see a lot of 500’s data and check if my assumptions were correct. I wanted to learn more.

What were your favorite parts of the program?

All of the coursework covering cap tables, convertible notes, liquidation preferences, and the nuances of these documents was really helpful. I don’t think I would have learned that information so succinctly anywhere else. 

The exposure to Demo Day and the role play exercise of negotiating with founders also helped me develop a new mindset. That’s where I first thought, “OK, how am I going to approach interviewing founders?” Funnily enough, I had actually invested beforehand in one of the startups that 500 Startups brought to the program. It turned out to be one of my better investments and I even remembered the terms in class! 

The validation I got from learning about 500’s portfolio theory and diversification was also critical, especially in this asset class. And then there were the relationships. I made so many great friends in the class. I felt like I found my people!

How did Deal Camp impact your confidence as an angel investor?

It definitely impacted my confidence. Before the program, I would wonder, “Am I doing the right thing? Is this the right portfolio theory?” After the program, I had the validation I needed and I knew I was on the right path. The results have been great. I’ve made over 350 angel investments and I have 8 unicorns and only an 8% shutdown. 

What advice do you have for aspiring angel investors who are considering the program? 

I recommend Deal Camp to so many people who are starting out in angel investing. The value for me was validation and making sure I understood the technical details of investing, which can be complicated. The other big takeaway is about the importance of deal flow and the network you build. But you’re only going to get the benefits if you work on those relationships in class. I am still seeing benefits years later. 

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