The Exchanges

Q Or what would you say is the key?

A You know, I would say there are a couple. I think that, um, founders and successful entrepreneurs tend to be optimistic. They tend to be decisive. Um, a characteristic of a unsuccessful entrepreneur is the inability to make decisions in particular, hard decisions. So successful entrepreneurs tend to be more decisive. Another characteristic, Harry, is this idea of self-awareness, you know, not getting too full of yourself. Not drinking your own Kool-Aid, um, and, and being brutally honest about what your skill set is and where your weaknesses are. A lot of us as entrepreneurs tend to wait way too long to hire a compliment, you know, to our team, someone who's better at us than marketing, or someone who actually understands, you know, the difference between financial accounting and financial analysis, and there's a big difference there. Um, two of the other characteristics or so, um, You know, uh, one is, is this idea of just, you know, getting up in the morning and being juiced, being motivated, um, to persevere. One of the quotes that I think of, um, that I, I carried with me is, um, you know, the degree to which we persevere in the face of hardship defines the strength of our character. And I think what that suggests is that, you know what, no matter what comes my way today as an Entrepreneur as, as someone who wants to be successful, I'm going to overcome. I'm going to persev…

AI assessment note: “I would say there are a couple. I think that, um, founders and successful entrepreneurs”

Q And did you have a little spending spree?

A Um, you know what? I'll just be brutally honest to that. I actually had achieved a level of financial independence and success before I sold, just cause I had, I used to be a really successful affiliate marketer in those early days, the early 2000. Um, so it, uh, I, did I go on a spending spree? Probably not. I had already moved at that point into my dream home and I was very fortunate, but, um, You know, I thought differently about what I could do for other people. I did, I did swipe a couple of checks to people I love. And, um, you know, I probably gave some money away to charity and stuff like that, which I wasn't in a position to do prior.

AI assessment note: “did I go on a spending spree? Probably not.”

Q So for a potential graduate listening in, say a 23 year old university student, how could they add value to a VC?

A Internships, um, you know, uh, asking them a, like, a very thoughtful question on something that they've written. I mean, if I write something and get it published, and someone reaches out, not unlike you did, and says, hey, you know, I read your article here or there on your blog, or on TechCrunch, or wherever, um, and, and what do you think about this? That's, I, I think that that's, that's one way of doing it, because you're adding value. You're, you're, You're being provocative, if you will. You're, you're challenging, you're, you're getting, you know, the, the venture capitalist or the influencer to, to think. Um, that's a big difference, Harry. Huge difference than what I get all the time. And again, I'm no Mark Cuban. I can't even imagine what Mark's email, um, and LinkedIn and all those things.

AI assessment note: “Internships, um, you know, uh, asking them a, like, a very thoughtful question”

Q So for a potential graduate listening in, say a 23 year old university student, how could they add value to a VC?

A Internships, um, you know, uh, asking them a, like, a very thoughtful question on something that they've written. I mean, if I write something and get it published, and someone reaches out, not unlike you did, and says, hey, you know, I read your article here or there on your blog, or on TechCrunch, or wherever, um, and, and what do you think about this? That's, I, I think that that's, that's one way of doing it, because you're adding value. You're, you're, You're being provocative, if you will. You're, you're challenging, you're, you're getting, you know, the, the venture capitalist or the influencer to, to think. Um, that's a big difference, Harry. Huge difference than what I get all the time. And again, I'm no Mark Cuban. I can't even imagine what Mark's email, um, and LinkedIn and all those things.

AI assessment note: “asking them a, like, a very thoughtful question on something that they've written”

Q Okay, fantastic. And then finally, tech bubble. Is it happening? Is it not happening? Um,

A No, there's, I mean, um, I think the valuations, uh, right now are, um, are very, very high. Um, but I, I don't believe so, and the reason I don't believe there's a tech bubble is because I believe that the period of time we're in right now is a period where you're going to see a lot of disruption, meaning that, you know, industries that have existed, whether it be the auto industry, for instance, Uber, um, or the hotel industry, um, Um, you know, uh, you know, for instance, um, there's so many different, uh, hotel companies out there like Airbnb and others. So we're going through this period of disruption where, whereas these old school industries that have kind of failed to innovate or haven't taken advantage of mobile, um, and in particular mobile, um, are, are really quite honestly, um, they've met their match. And so I think we have several more years of that. And I believe those companies are Should be very, very big company. So I think we'll go into a different sort of era in a couple of years where a lot of the disruption has happened and it'll move over into other industries. Um, but no, man, I'm, I'm long tech and I'm, you know, I'm, I'm investing my money where my mouth is as it relates to early stage tech in particular around, um, around mobile, um, social, uh, local, um, Um, and I, because of my background, I can't help but put some money into, um, to e-commerce.

AI assessment note: “I don't believe there's a tech bubble is because”

Q Or what would you say is the key?

A You know, I would say there are a couple. I think that, um, founders and successful entrepreneurs tend to be optimistic. They tend to be decisive. Um, a characteristic of a unsuccessful entrepreneur is the inability to make decisions in particular, hard decisions. So successful entrepreneurs tend to be more decisive. Another characteristic, Harry, is this idea of self-awareness, you know, not getting too full of yourself. Not drinking your own Kool-Aid, um, and, and being brutally honest about what your skill set is and where your weaknesses are. A lot of us as entrepreneurs tend to wait way too long to hire a compliment, you know, to our team, someone who's better at us than marketing, or someone who actually understands, you know, the difference between financial accounting and financial analysis, and there's a big difference there. Um, two of the other characteristics or so, um, You know, uh, one is, is this idea of just, you know, getting up in the morning and being juiced, being motivated, um, to persevere. One of the quotes that I think of, um, that I, I carried with me is, um, you know, the degree to which we persevere in the face of hardship defines the strength of our character. And I think what that suggests is that, you know what, no matter what comes my way today as an Entrepreneur as, as someone who wants to be successful, I'm going to overcome. I'm going to persev…

AI assessment note: “I would say there are a couple. I think that, um, founders and successful entrepreneurs”

Q And did you have a little spending spree?

A Um, you know what? I'll just be brutally honest to that. I actually had achieved a level of financial independence and success before I sold, just cause I had, I used to be a really successful affiliate marketer in those early days, the early 2000. Um, so it, uh, I, did I go on a spending spree? Probably not. I had already moved at that point into my dream home and I was very fortunate, but, um, You know, I thought differently about what I could do for other people. I did, I did swipe a couple of checks to people I love. And, um, you know, I probably gave some money away to charity and stuff like that, which I wasn't in a position to do prior.

AI assessment note: “did I go on a spending spree? Probably not.”

Q Chris, welcome to the 20 Minute VC. It's an absolute pleasure to have you on the show. Um, first, let's start by hearing a bit about yourself and your background. So, what was the driving force for you entering into the venture capital world?

A Well, first, you know, thank you, Harry, for the opportunity to engage with your audience. Um, it's, it's really an honor and a pleasure. Um, so yeah, I've, I've been, Well, I call an accidental entrepreneur. Um, I was a professional student for nine years, um, after high school, so I went to Penn State and got an undergraduate degree in psychology, and then went on to graduate school, um, where I studied experimental psychology, and I got a master's degree, and then I went to law school and got a law degree, but it was in, it was really my first year at Villanova, Back in 1999. So it's really 19, late 1998, 99, where I became enamored, really fascinated by how I thought the Internet was going to change the way we do things. And I guess that was somewhat reminiscent because I think all of your listeners would agree that the Internet has completely changed the game. It's kind of rocked the world internationally, and it's created a tremendous amount of opportunities for entrepreneurship. Um, so, uh, I will get to your question by saying that, uh, I decided to get in the game. You know, even though I was a student, I decided to go online, build my own website, and figure out how to make money. And so what I did for about a year, year and a half was, um, became obsessed with learning, self-teaching, learning everything I could about how to generate web traffic, And then monetize or…

AI assessment note: “I will get to your question by saying that, uh, I decided to get in the game.”

Q Now, what would you say was the most important lesson that you learned from this journey with Pepper Jam from the idea to the sale of the company? What's the most important lesson that you learned?

A You know, that's great. Um, here, here's the lesson. The lesson is that there are a, uh, a number of specific characteristics and qualities of successful entrepreneurs, those that succeed. Um, there are also characteristics, uh, uh, that are, that, that don't contribute to success and, and those entrepreneurs tend not to succeed. So when I look back on Pepper Jam, uh, Clearly I, I made a lot of good decisions, right? Because I, it ended, it resulted in a good outcome, but, you know, being, having hindsight to look back and say, what do I know now that I didn't know then? There's a number of things that I do differently now. Um, but ultimately those characteristics that I referred to are really the value that I give the companies that I invest in. And when I write for Forbes or anchor for any of these, you know, big publications, um, That's what I'm trying to share. I just share, I just wrote an article, um, that I submitted yesterday. It's called the power of gratitude. And it's amazing that, you know, leaders, successful people tend to be grateful. They tend to focus on the things in their life that are positive, um, and that breed optimism. Um, and those are the type of characteristics that, uh, correlate with being grateful for what we have. Um, even though we want more, You know, I mean, I think that's, it's okay to want more, but getting more in tune with what you're grate…

AI assessment note: “getting more in tune with what you're grateful for and stop focusing on”

Q Now, what would you say was the most important lesson that you learned from this journey with Pepper Jam from the idea to the sale of the company? What's the most important lesson that you learned?

A You know, that's great. Um, here, here's the lesson. The lesson is that there are a, uh, a number of specific characteristics and qualities of successful entrepreneurs, those that succeed. Um, there are also characteristics, uh, uh, that are, that, that don't contribute to success and, and those entrepreneurs tend not to succeed. So when I look back on Pepper Jam, uh, Clearly I, I made a lot of good decisions, right? Because I, it ended, it resulted in a good outcome, but, you know, being, having hindsight to look back and say, what do I know now that I didn't know then? There's a number of things that I do differently now. Um, but ultimately those characteristics that I referred to are really the value that I give the companies that I invest in. And when I write for Forbes or anchor for any of these, you know, big publications, um, That's what I'm trying to share. I just share, I just wrote an article, um, that I submitted yesterday. It's called the power of gratitude. And it's amazing that, you know, leaders, successful people tend to be grateful. They tend to focus on the things in their life that are positive, um, and that breed optimism. Um, and those are the type of characteristics that, uh, correlate with being grateful for what we have. Um, even though we want more, You know, I mean, I think that's, it's okay to want more, but getting more in tune with what you're grate…

AI assessment note: “getting more in tune with what you're grateful for and stop focusing on”