Sramana Mitra: Your strategy is to not worry about the ones that are not really making it and will have to raise money with liquidation preference where you don’t have the negotiating leverage. Focus on the ones that will get to decent exit and you need three of those to make your fund economics work.
Charlie O’Donnell: Yes. I do 80% to 90% of my total investment upfront, which is a deviation from the way that most fund managers work on it. The way to think about my fund is, if you had a $100 million seed fund, what percentage of that fund goes into the seed round? If you’re following on three to one or four to one, you’re really talking about, at most, 20% of the fund and the rest of it was dollars when you double down on your winners. >>>
Brian Jacobs: As far as the future of the cloud is concerned, I think we continue to see more and more innovation. I believe innovation begets more innovation. Once you see how the cloud changes your business, you start to see new opportunities that maybe weren’t so visible initially.
I think that this idea around industry cloud, which is a vertical software company that is enabling competitors to aggregate data and share data without compromising their trade secrets, is an exciting opportunity. It’s a mix of vertical software with Big Data with the idea that by sharing data in the cloud, you can do some things that companies with an on-premise solution just can’t do. That’s one of our key investment themes.
Another one is mobile business applications. We think that the mobile phone is now effectively a supercomputer in your pocket. >>>
Sramana Mitra: Media buying has been the most obvious areas which needed to be automated because of the trends that you described. Machine learning applies very well into that space. Can you talk about other areas in marketing technology, where, powered by machine learning, there is venture-scale opportunity?
Ashu Garg: I’m going to talk about very broad themes. The beauty of entrepreneurship is, startups always prove investors wrong. I’m sure that there are folks in this audience who will have ideas that we haven’t even thought of. With that caveat, I published a book called The Decade of The CMO last year. We talked about five major technology trends within marketing technology and five buckets of areas where I think mostly billion-dollar companies will emerge. >>>
Sramana Mitra: How do you process the current investment climate where capital is moving further and further upstream? Some of the funds that I’m sure you were involved in your previous life are becoming gigantic funds. As a result, they have to move upstream and deploy larger chunks of capital right away. How does a seed investor mitigate the Series A gap?
Charlie O’Donnell: For every fund that you’ve seen move up, you have some set of funds that fills in that space. The capital environment is pretty efficient. We certainly have Series A funds that insist on deploying $8 million to $20 million. It’s very hard to get a seed-funded company from their initial check to a position where they can take on a $10 million investment. >>>
Brian Jacobs: As we learned more and more about how the cloud changes everything, we have evolved our investment thesis. We found some new areas where the cloud really does provide a new opportunity. Rather than disrupting incumbents, we’re taking advantage of the cloud to do things that we could never do before.
For instance, we knew that the social wave in the consumer world was going to affect businesses. If all of the employees and customers are on social networks, that’s going to affect businesses that try to serve consumers as well as the companies who have those workers in their midst.
We’ve invested in a number of companies that are bringing social technologies to business. We started to realize that the >>>

There are currently about 500 funds spanning pre-seed, seed, post-seed, pre-Series A and startup investing is constantly evolving. Entrepreneurs with an eye on financing need to keep up with the trends and special interests of VCs, Angels and seed investors. Have a listen to my recent 30-minute podcast interviews with five investors who have a wide range of interests, from AI concepts to women entrepreneurs, from Indian startups to non-Unicorn ventures. Perhaps your startup fits within one of their areas of interest?
Ankit Jain is Founding Partner at Gradient Ventures, Google’s new AI venture fund, which will invest in and connect early stage startups with Google’s resources, innovation, and technical leadership in artificial intelligence.
Sramana Mitra: You spoke with me a year back about marketing technologies. It was a core area of interest at least a year ago. Help us understand what drives that interest.
Ashu Garg: That is absolutely a core area of interest for us. I would say it is one of the trends in the broad bucket of the transformation of software using machine learning. Marketing technology is probably, by far, the first category where that happened. We definitely made significant investments and have big bets on that. >>>
Sramana Mitra: I was talking to John Staenberg up in Seattle. He’s one of the most prolific investors in the North West. He’s invested in 300 companies. One of the drivers of how he chooses which entrepreneurs he wants to engage with is what he wants to learn about.
For example, he’s not very knowledgeable about Bitcoin and he is interested in learning about Bitcoin. He’s interested in entrepreneurs who are working on new opportunities in Bitcoin as a mechanism of understanding that trend.
Yes, investors do look to entrepreneurs to educate them and train them, which is what was driving my question