The Exchanges

Q And what advice then would you give someone looking to join a syndicate, or looking to start one themselves, having the experience that you've had, what would you recommend to them?

A If you want to join a syndicate, uh, I'd say go out there and, you know, just look around the list and, People. I think most syndicate leads actually respond to the people so you can reach out to them depending on your, your check size. Um, if it's very small, uh, you may just want to watch people and observe what deals they do and look to their blogs and see you connect with. But at the end of the day, if you're going to go back syndicates, it's a portfolio play. So go find a syndicate lead or two that you like and try to back as many deals as possible. You're better off investing in our portfolio. Whether it's mine or Jason or Tim's or someone out there, invest in their portfolio, not one deal. If you're going to start a syndicate, please do it once you have some real fucking experience, because there's a lot of people start syndicates who have no business doing so, but it's the same with people who start funds and have no business doing so. If you're going to invest other people's money, you should at least have a few years experience investing your own money or have been investing Money another fund and have true performance. Please don't treat Angelus syndicates as a way. This is my own biased opinion, not Angelus, but don't treat Angelus syndicates as training wheels for becoming an investor is a very real step into being an investor. So please come armed with experience …

AI assessment note: “If you want to join a syndicate... If you're going to start a syndicate”

Q And then what other moment has provided the most profound learning point for you in your investing career?

A I think, uh, the value of my existing portfolio. So I haven't written about this yet, but I wrote Probably the first, the very first check into a company back then known as context logic, which is now wish.com. And they're a very large e-commerce play now, billions of dollars that came from an introduction, uh, from Brian Wong of keep. I really believe in staying in touch with all my founders, not just helping them, but great founders attract other great founders. And so they're, they're an amazing filter for me as I think about meeting people, I constantly ask my founders. In fact, we just closed a deal or closing a deal this week in New York, which came via a founder that I backed five years ago. And I really value the founders I work with, not just in the transactional mode of the companies that are building today or the companies they may build five years from now, but my founders have great opinions and great networks of their own. And I really value the introductions they make for me.

AI assessment note: “I wrote Probably the first, the very first check into a company back then known as context logic”

Q And let's talk about the fund itself now. And Arena VC is extremely unique in the way it's a VC coupled with an AngelList syndicate and now 3.9 million dollars. So congratulations. That's unbelievable. But why did you go for this dual approach to investing?

A I did it because, you know, I, I talked to Jeff, um, my partner last year and sort of, you know, I, I seed funded AngelList, uh, about five years ago. Because I believed in the vision of crowdfunding back then. And finally, you know, this year, or last year, it was a reality that we could actually pull in investors, not just the already wealthy with their big funds, but we could run a fund and do well by our LPs and ourselves, but we could also extend investment to other savvy investors who may be You know, business men or business women in their own industries. These could be professors. They could be engineers. We could bring early stage investing to the masses of accredited investors by doing syndicates through AngelList. And that, you know, that excited me. The opportunity to bring in, you know, in each deal, you know, 80 to 90 other early stage investors who could all benefit from how we, you know, run our funds. And the way we work is that, We, Arena Ventures, invest, and every time we invest, we share a part of that deal with the AngelList community, and they get to invest in, in that deal at the very same terms that we do, and it's an amazing opportunity. This has never existed in the world before, and I wanted to do it very selfishly. I, I love the cause that AngelList is behind, and I wanted to support them and also do well by ourselves.

AI assessment note: “We could bring early stage investing to the masses of accredited investors by doing syndicates”

Q And people look at you at Arena Ventures when they're kind of looking to invest in a syndicate and see two great investors, but what do you think makes a great investor, and what do great investors add to their companies?

A I'd say, so my biggest quality, when I, when I looked around and built our team, so we're a team of seven people here at Arena, the biggest thing I look for in an investor is someone who innately wants to help. As an investor, I view our biggest responsibility after You know, looking for our LPs and picking the right deals is my job is to want to help a founder. And whether that is stealing talent for you, you know, getting a partnership together, thinking of you and making the right connections every day. I think great investors genuinely love the people in the businesses they invest in, and they have a natural quality about themselves where they want to help and serve those founders. So that's, that's probably the most defining thing about us.

AI assessment note: “the biggest thing I look for in an investor is someone who innately wants to help”

Q And let's talk about the fund itself now. And Arena VC is extremely unique in the way it's a VC coupled with an AngelList syndicate and now 3.9 million dollars. So congratulations. That's unbelievable. But why did you go for this dual approach to investing?

A I did it because, you know, I, I talked to Jeff, um, my partner last year and sort of, you know, I, I seed funded AngelList, uh, about five years ago. Because I believed in the vision of crowdfunding back then. And finally, you know, this year, or last year, it was a reality that we could actually pull in investors, not just the already wealthy with their big funds, but we could run a fund and do well by our LPs and ourselves, but we could also extend investment to other savvy investors who may be You know, business men or business women in their own industries. These could be professors. They could be engineers. We could bring early stage investing to the masses of accredited investors by doing syndicates through AngelList. And that, you know, that excited me. The opportunity to bring in, you know, in each deal, you know, 80 to 90 other early stage investors who could all benefit from how we, you know, run our funds. And the way we work is that, We, Arena Ventures, invest, and every time we invest, we share a part of that deal with the AngelList community, and they get to invest in, in that deal at the very same terms that we do, and it's an amazing opportunity. This has never existed in the world before, and I wanted to do it very selfishly. I, I love the cause that AngelList is behind, and I wanted to support them and also do well by ourselves.

AI assessment note: “We could bring early stage investing to the masses of accredited investors by doing syndicates”

Q Now, can you give us a little walkthrough of your career so far, and how you ended up investing at Arena VC?

A Yeah, man, you know, I, uh, I spent most of my life, the first half of my life, In the military and national security community, very different from tech. I built up a private military, sold that business, and about eight years ago, decided to go start working with entrepreneurs, and I just started writing checks, and honestly, I didn't know a damn thing when I started. I, I just tried, like founders would try. I, I tried and failed and tried and failed as an angel investor, And eventually, over years and years, I think I got a little bit better. I got a little bit more experience, and I realized I love what I do, and I started a fund early this year with one of my best friends, Jeff Lowe, called Arena Ventures, and all we do these days is invest in founders very early, usually the first money in, and We're very active investors. That's sort of the short summary of my life.

AI assessment note: “started a fund early this year with one of my best friends, Jeff Lowe”

Q And what advice then would you give someone looking to join a syndicate, or looking to start one themselves, having the experience that you've had, what would you recommend to them?

A If you want to join a syndicate, uh, I'd say go out there and, you know, just look around the list and, People. I think most syndicate leads actually respond to the people so you can reach out to them depending on your, your check size. Um, if it's very small, uh, you may just want to watch people and observe what deals they do and look to their blogs and see you connect with. But at the end of the day, if you're going to go back syndicates, it's a portfolio play. So go find a syndicate lead or two that you like and try to back as many deals as possible. You're better off investing in our portfolio. Whether it's mine or Jason or Tim's or someone out there, invest in their portfolio, not one deal. If you're going to start a syndicate, please do it once you have some real fucking experience, because there's a lot of people start syndicates who have no business doing so, but it's the same with people who start funds and have no business doing so. If you're going to invest other people's money, you should at least have a few years experience investing your own money or have been investing Money another fund and have true performance. Please don't treat Angelus syndicates as a way. This is my own biased opinion, not Angelus, but don't treat Angelus syndicates as training wheels for becoming an investor is a very real step into being an investor. So please come armed with experience …

AI assessment note: “If you're going to start a syndicate, please do it once you have some real”

Q And is there any aspects that you'd like to improve on yourself as an investor?

A Yeah, you know, I'd say if you know me well, I'm, uh, you know, I love the people I work with and back. Um, I can also get extremely irritated and aggressive, uh, which is good in some situations where we need to fight, you know, with regulators or we need to fight with competitors. I can be very, very aggressive. Um, and I have to think of that consciously all the time. Luckily, my co-founder is, uh, uh, as well as my girlfriend, Laura, are amazing balances for my natural tendency to want to go into fight mode versus sometimes negotiation mode. I'm, and so that's, that's the thing I have to work on and keep in my head constantly is that I'm a natural Fighter, I'm very aggressive, but that's not always the best answer to every situation.

AI assessment note: “that's the thing I have to work on and keep in my head constantly”

Q Um, why do you think your syndicate has become one of the most successful? What are the key drivers, do you think, to your success?

A Probably because we tell people about it. I mean, that's, we, we tell people on email, and we tell people on conferences, and we tell people, hey, this is what we're doing, uh, we're not ashamed of it, so we talk about it. I think if you look at any of the other top syndicates out there, you'll find that the people who have top syndicates have gone out there unashamedly and told people, hey, I'm doing this, set my flag, and And after that, I think they look at our, our performance and our history, and some people will probably talk to the founders we've backed and realize that we're, we're good people, and we actually give a shit about the founders, and we have had great results. So I think it's a combination of telling the world, hey, we're doing this, and two, when you do look at what we're doing, we're actually really good at it.

AI assessment note: “Probably because we tell people about it.”

Q Now, can you give us a little walkthrough of your career so far, and how you ended up investing at Arena VC?

A Yeah, man, you know, I, uh, I spent most of my life, the first half of my life, In the military and national security community, very different from tech. I built up a private military, sold that business, and about eight years ago, decided to go start working with entrepreneurs, and I just started writing checks, and honestly, I didn't know a damn thing when I started. I, I just tried, like founders would try. I, I tried and failed and tried and failed as an angel investor, And eventually, over years and years, I think I got a little bit better. I got a little bit more experience, and I realized I love what I do, and I started a fund early this year with one of my best friends, Jeff Lowe, called Arena Ventures, and all we do these days is invest in founders very early, usually the first money in, and We're very active investors. That's sort of the short summary of my life.

AI assessment note: “started a fund early this year with one of my best friends, Jeff Lowe, called Arena Ventures”

Q And you mentioned that you're slightly unorthodox entrance into VC with your military background. So taking that into account, how do you think that shaped your investing thesis and what were your biggest takeaways from that experience?

A I think it shaped me because, uh, sort of like a novice founder, I walked into investing knowing nothing. And so having no preconceptions about what was right or what was wrong, And because I didn't know anything, that ignorance led me to doing what I thought was right, which was to focus on the people. And so I've, since day one, always focused on the characteristics and the behavior and the attitude and the drive of the founders first. That's my first filter for how I think about investing. And then second, I think about the product and the market and the business, which is important, definitely. But to me, the, the, Qualities of the founders are the most important, the most enduring part of any company, and the only thing you can truly understand as an early stage investor, and I'd say that my ignorance led me to that realization.

AI assessment note: “ignorance led me to doing what I thought was right, which was to focus”

Q Um, why do you think your syndicate has become one of the most successful? What are the key drivers, do you think, to your success?

A Probably because we tell people about it. I mean, that's, we, we tell people on email, and we tell people on conferences, and we tell people, hey, this is what we're doing, uh, we're not ashamed of it, so we talk about it. I think if you look at any of the other top syndicates out there, you'll find that the people who have top syndicates have gone out there unashamedly and told people, hey, I'm doing this, set my flag, and And after that, I think they look at our, our performance and our history, and some people will probably talk to the founders we've backed and realize that we're, we're good people, and we actually give a shit about the founders, and we have had great results. So I think it's a combination of telling the world, hey, we're doing this, and two, when you do look at what we're doing, we're actually really good at it.

AI assessment note: “Probably because we tell people about it.”

Q And is there any aspects that you'd like to improve on yourself as an investor?

A Yeah, you know, I'd say if you know me well, I'm, uh, you know, I love the people I work with and back. Um, I can also get extremely irritated and aggressive, uh, which is good in some situations where we need to fight, you know, with regulators or we need to fight with competitors. I can be very, very aggressive. Um, and I have to think of that consciously all the time. Luckily, my co-founder is, uh, uh, as well as my girlfriend, Laura, are amazing balances for my natural tendency to want to go into fight mode versus sometimes negotiation mode. I'm, and so that's, that's the thing I have to work on and keep in my head constantly is that I'm a natural Fighter, I'm very aggressive, but that's not always the best answer to every situation.

AI assessment note: “that's the thing I have to work on and keep in my head constantly”

Q And people look at you at Arena Ventures when they're kind of looking to invest in a syndicate and see two great investors, but what do you think makes a great investor, and what do great investors add to their companies?

A I'd say, so my biggest quality, when I, when I looked around and built our team, so we're a team of seven people here at Arena, the biggest thing I look for in an investor is someone who innately wants to help. As an investor, I view our biggest responsibility after You know, looking for our LPs and picking the right deals is my job is to want to help a founder. And whether that is stealing talent for you, you know, getting a partnership together, thinking of you and making the right connections every day. I think great investors genuinely love the people in the businesses they invest in, and they have a natural quality about themselves where they want to help and serve those founders. So that's, that's probably the most defining thing about us.

AI assessment note: “the biggest thing I look for in an investor is someone who innately wants to help”

Q And then moving on to the more kind of broad crowdfunding industry as a whole now, we've seen crowdfunding evolve and really impact the early stage investing environment. Do you believe it poses a threat to the more traditional form of VC?

A I think it's one more animal in the, in the kingdom. You know, there's, There's going to be late stage funds, and there's going to be early stage funds, and there's going to be crowdfunding, and everyone's figuring out how to work with this new crowdfunding movement. You know, we've, we've adopted our strategy, which is to run a traditional fund plus crowdfunding together, but I don't think it displaces any key categories. I think it does threaten early stage funds that maybe are weaker, I think that AngelList definitely brings more transparency to the world of angel investing and early stage investing. Nowadays, if you're an investor and you're not on AngelList, it's sort of like a couple of years, a few years ago when people were like, oh, you don't have a LinkedIn profile. How do you actually have a job? And so you have to have an AngelList profile. And by doing that, you, you know, if you want people to pay attention, you have to put your portfolio up there. And increasingly AngelList is getting more information about when you did that deal, how much you put into the deal, what your returns are. And so I think AngelList is driving more transparency into the environment, which is good for all of us. It's good for founders. It's good for LPs. It's good for syndicate backers to have that transparency.

AI assessment note: “I don't think it displaces any key categories. I think it does threaten early stage funds”

Q And then what other moment has provided the most profound learning point for you in your investing career?

A I think, uh, the value of my existing portfolio. So I haven't written about this yet, but I wrote Probably the first, the very first check into a company back then known as context logic, which is now wish.com. And they're a very large e-commerce play now, billions of dollars that came from an introduction, uh, from Brian Wong of keep. I really believe in staying in touch with all my founders, not just helping them, but great founders attract other great founders. And so they're, they're an amazing filter for me as I think about meeting people, I constantly ask my founders. In fact, we just closed a deal or closing a deal this week in New York, which came via a founder that I backed five years ago. And I really value the founders I work with, not just in the transactional mode of the companies that are building today or the companies they may build five years from now, but my founders have great opinions and great networks of their own. And I really value the introductions they make for me.

AI assessment note: “I think, uh, the value of my existing portfolio.”

Q And when you compare your investment strategy from when you were angel investing to when you started as a VC and then with AngelList, did it change hugely when it suddenly transferred from being your money to someone else's money?

A It's a very big difference in terms of responsibility, but I really don't feel it's that much different nowadays because I have, you know, I came into being a VC after having many years of investing my own money. So, I, I feel super comfortable in this world. I know how to find deals. I know how to evaluate them. I have my own thesis, my own frameworks. I know everything from the finances, the legal, the operations. I, you know, I'm really experienced, so I feel very natural moving from being an angel to a VC. Uh, the biggest thing is that I have a great team of people around me that can help me close deals and find deals, and we write bigger checks. Other than that, the process of finding the deals and closing the deals seems very Very much like I used to do as an angel, just with a better team around me.

AI assessment note: “I really don't feel it's that much different nowadays”

Q And then moving on to the more kind of broad crowdfunding industry as a whole now, we've seen crowdfunding evolve and really impact the early stage investing environment. Do you believe it poses a threat to the more traditional form of VC?

A I think it's one more animal in the, in the kingdom. You know, there's, There's going to be late stage funds, and there's going to be early stage funds, and there's going to be crowdfunding, and everyone's figuring out how to work with this new crowdfunding movement. You know, we've, we've adopted our strategy, which is to run a traditional fund plus crowdfunding together, but I don't think it displaces any key categories. I think it does threaten early stage funds that maybe are weaker, I think that AngelList definitely brings more transparency to the world of angel investing and early stage investing. Nowadays, if you're an investor and you're not on AngelList, it's sort of like a couple of years, a few years ago when people were like, oh, you don't have a LinkedIn profile. How do you actually have a job? And so you have to have an AngelList profile. And by doing that, you, you know, if you want people to pay attention, you have to put your portfolio up there. And increasingly AngelList is getting more information about when you did that deal, how much you put into the deal, what your returns are. And so I think AngelList is driving more transparency into the environment, which is good for all of us. It's good for founders. It's good for LPs. It's good for syndicate backers to have that transparency.

AI assessment note: “I don't think it displaces any key categories. I think it does threaten early stage funds”

Q And then what's the next industry to be disrupted?

A The next, man, uh, the whole world, but, uh, man, let me pick one. I think government is absolutely horrible and screwed up, and, and it's hard to imagine how a for-profit company can go disrupt it, but I'm very open to Founders who are disrupting government. I have no idea what to disrupt, but maybe go fix, uh, maybe a text bait, maybe magic or like service, but for government, a text interface to our local government. The other area I'm interested in, um, are nonprofits taking activities that nonprofits have traditionally done, but doing them in a for-profit way. Uh, an example that is, we invest in a company called Andela, which is changing education in Africa right now. And they took on A traditional nonprofit mission of education. They made an incredible for-profit model that is changing how we educate kids in, in Africa right now. So those are two off the top of my head.

AI assessment note: “we invest in a company called Andela, which is changing education in Africa”

Q And then what is the most recent investment you've made and why did you say yes?

A Closing right now. So I can't tell you the name of the lady, but it is a woman we met via a company I founded years ago in LA and we decided to do the deal. After talking for a couple hours, she spoke to one of my associates in our EIR, um, and they felt that she was the right personal fit for the company, and I met her, and I was just struck by her, her brilliance, her, her focus, her, uh, her passion for her business, the intensity, and there's all these personal qualities, and, and after two hours of meeting with her, I called my partner, Jeff, and said, This is the kind of lady that we invest in, uh, and that just happened, and we're getting that done right now.

AI assessment note: “I was just struck by her, her brilliance, her, her focus”

Q And you mentioned that you're slightly unorthodox entrance into VC with your military background. So taking that into account, how do you think that shaped your investing thesis and what were your biggest takeaways from that experience?

A I think it shaped me because, uh, sort of like a novice founder, I walked into investing knowing nothing. And so having no preconceptions about what was right or what was wrong, And because I didn't know anything, that ignorance led me to doing what I thought was right, which was to focus on the people. And so I've, since day one, always focused on the characteristics and the behavior and the attitude and the drive of the founders first. That's my first filter for how I think about investing. And then second, I think about the product and the market and the business, which is important, definitely. But to me, the, the, Qualities of the founders are the most important, the most enduring part of any company, and the only thing you can truly understand as an early stage investor, and I'd say that my ignorance led me to that realization.

AI assessment note: “I walked into investing knowing nothing. And so having no preconceptions about what was right”