Story really starts when I was quite young, I was always hustling small businesses. I had a DJ business that I started when I was in eighth grade and I would DJ parties and dances. I can't even believe it today. But when I was in eighth grade, someone actually hired me. I think they paid me like, $125 to play music at their wedding. I think they must have been really desperate and my dad was nice enough that we would drive me around with my speakers and my music and and then I got a little older. I expanded that business and then I think by the time I got into college and I was studying business, it became more clear to me that entrepreneurship, the idea of owning your own business or starting your own business seemed really attractive, and it just began to sort of explain who I was to myself.

Break that answer into two parts. For many, many years, I've been an angel investor, and I've just invested my own capital. I didn't have any institutional investors to answer to, and so that created a lot more flexibility around the stage that I might invest at, the types of companies I might invest in, and I think, sometimes you invest for greed but often times there are other reasons. For example, several years ago I invested in a cosmetics, a beauty company called Julep, and part of that motivation is because I have five daughters and I thought it would be an interesting outlet for me to expose them to business in a category that they might enjoy, and it was a female founder who I really look up to, and I thought she would be a terrific role model for my daughters, and so I would often bring one of my daughters to the board meetings and so my motivation was not primarily money or a return, it was more of an experience and other times that made investments. For example, when I was starting stance, I did a research project on about 300 different consumer product categories, and I rank them based on the size of their market, the gross characteristics, the homogenization of the competitive set, gross margin profile, repeat purchase rate, Internet friendliness, these kinds of things, and I became, quite researched in all of these different categories. I really began to understand them. Eventually I chose to start Stance, which was focused on socks at the time. But I also liked the characteristics of luggage and perfume, there were several other categories that I really liked. I just didn't do them. And so eventually when the founders of Away approached me to do luggage because already understood the category and it spent a lot of time working on it, it was a really easy investment decision, and later I was approached to do a perfume business and same thing. The reason why I didn't pursue it was because I knew it would be difficult to sell smell over the Internet. But I felt like this particular company had done a good job of sort of overcoming that, and so sometimes I would say the investments come in and they align on a thesis that I had earlier, and and so it's a really natural investment at that point, the second part of the answer would be now that I am best on behalf of institutions, our charter, the scope of the kinds of investments that we make is much more targeted, and we primarily invest in series a rounds of financing. We like to be the first institutional investor, we like the lead, we like to have ownership percentage targets of 15 to 20% and like most other venture capitalists, we tend to invest in businesses that have high gross margin profiles, have a large R and D capital expenditure upfront, but eventually, when they build their product will have high gross margins into the future. Of course, software and other kinds of technology businesses fit that perfectly, which is why I believe most venture capitalists target those kinds of opportunities. So today I probably wouldn't invest in a perfume company, whereas if it was just me as an individual, I might. So the kinds of investments that I do today are slightly different. It would be hard for me to invest in a chain of Mexican restaurants, but I did that earlier in my career as an angel investor for fun.

That really stands out above all is the trajectory, the traction and and however that is measured. It's often not revenue or profit because the company's are so early. So, figuring out as an entrepreneur how you communicate the traction that you have, in whatever format that might be. It could be as rudimentary as you know, transcripts of customer calls, but figuring out a way to communicate to the investor why you have positive momentum, I think above all else, that's the thing that gets someone's attention. If you're earlier than that and you don't have any traction or momentum yet, then you really have to rely on your historical credentials, the team, other, the market characteristics, maybe why your team is so perfectly suited to create a solution to this problem, but you have to rely on other elements. I think that's one of the reasons why it's easier for second or third time entrepreneurs to raise money because they can identify a problem in a market opportunity and they have the credibility to raise money against it because of their past and it's harder to do that as a first time entrepreneur in a pre traction, pre product company, because you don't really have the resume or the credentials to give credibility to the market opportunity that you've spotted. So I think that's why the fundraising is often harder for first time folks. But I don't think it makes them any less capable of solving those problems.