Gavin McCulley | Angel Investor and Founder of Twin River Holdings : High Speed Low Drag Podcast

Gavin-McCulley-1085918-767Gavin McCulley explains the game of Angel Investing

High Speed Low Drag Episode 6.

High Speed Nation. John Lee Dumas here and I am fired up to bring you our featured guest today, Gavin McCulley. Gavin, are you prepared to ignite?

Gavin: I am prepared to ignite.

John: Yes. Gavin is a former Army Logistics Officer who served in both Iraq and Afghanistan. Gavin left the Army in late 2008 to become an entrepreneur only to find himself ?in a tumultuous economy. In search of capital first owned business, he learned firsthand the game of angel investing and over the last six years has founded his own angel investment partnership and leads one of the nation’s largest groups of angel investors.

Gavin, I?ve given our listeners just a little overview but tell us about you personally and then we?ll dive on in.

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Gavin: John, thank you for having me. I?m beyond excited to be part of this community and a part of this new initiative. I hope that you light this thing en fuego for you. So I?m been a huge fan of yours for a long time.

What I did is I?ve found myself in that spot of I didn?t know what to do. I didn?t know where to go for capital. I didn?t know who to talk to. So I started knocking on doors here, there and everywhere. What I learned was that angel investors are a huge diverse group with different appetites and different ways of doing things. But they?re out there; they’re hard to find. And what I wanted to do was solve the problem of getting interested inventors in a room and helping entrepreneurs find that capital, find that mentorship, get the money they need, get the resources they need and so they could go ahead and launch their business, and then be part of it after the fact where we could be with them along the journey.

So that?s where I started. That was the driving force behind it. I started out with my company. My individual partnership is called Twin Rivers Holding. We have investments in all kinds of different things. We don?t back a type of company. We back a type of person. So as my partner always says, it?s the who not the what. Then we translate that over into a larger group where we brought on other people who want to follow in our example and aggregate our capital and put it to work.

John: So Gavin, my first thoughts here are why does angel investing have to be such a mystery? These are the same thoughts that were going through your mind. How would the average person even start? What would be that first step? I?m so excited that you have been that guiding light. You have been that person that has turned on that lantern and shown people the way. So I have to commend you for that because this is going to launch and it has launched and will continue to launch so many incredible ventures as we go forward. I have no doubt.

We?re about to move into the successful Gavin but before we do, I want to have a little side note, man, because it?s pretty cool. I’m not going to lie. I think it?s pretty cool the history that you and I have because it?s not every day I get to talk to a fellow Patriot Battalion, Providence College Army ROTC alumni.

So Gavin, you are one year ahead of me in college. You and I got there and I was doing the ROTC thing. You were that person that was already squared away. So I looked up to you in a lot of ways. I learned a lot from you. I just want to thank you firsthand for being there for my class.

Gavin: John, I tell you what, man, it was an honor. You were always a lot of fun. You were one of the funniest guys in our battalion. I can recount those stories later. But thank you, John. It is really cool. I watched you come up and I watched this amazing transformation happen to you after your transition from the military that you’re abroad traveling. And then to find what you?ve done with Entrepreneur On Fire is just amazing. So I?m really proud of you, man, and congrats.

John: Thanks, Gavin. It?s all part of the journey, for sure. You would not have tagged me at all as somebody that was on his way to success within the Patriot Battalion my first couple of years. I was kind of a little bit of a rebel — didn?t want to shave, didn?t want to go to PT — all that stuff that everybody listening because you?re veterans, you know.

But lo and behold, I got my act together and my mindset shifted between that junior-senior year when we had to go and actually be at Fort Lewis, Washington. When I saw that I could actually have success if I applied myself and I graduated number four in our battalion, that?s why I kind of had that mentality shift. So you never know what?s going to happen or who it?s going to happen to. So it?s cool just to think about it.

Gavin, let?s not delay anymore. You have an amazing success quote for us. So take it away.

Gavin: Okay. “Formal education will make you a living. Self-education will make you a fortune.” That was by Jim Rohn.

I tell you the way I apply that, you know, I’ve heard some great successes on your shows, on Entrepreneur On Fire, and others. But the way that that one resonates with me, guys, is we are responsible for our own education. I spend an enormous amount of time. You can ask my wife. I walk around the house and the office always with earbuds in. I?m listening to books on tape. I?m writing notes at nighttime. I?m reading my Kindle and making notes.

It really is up to us to go out there, to educate ourselves, to make ourselves more competitive, to give ourselves the tools to succeed. So that?s the quote that I hope resonates with you guys.

John: Well, that resonates with me and I can actually vouch High Speed Nation, that Gavin is just that type. He?s always consuming when he has the opportunity. I remember having a chat with you. It was over a year ago for sure, maybe a year and a half ago now, where we were just talking and you were saying, “Hey, Entrepreneur On Fire is going well.” In fact, you are in my earbuds very evening when I?m feeding my baby at night. It was like 2:00 a.m. or something.

That?s the one that struck me. It?s the power podcasting, the power of getting your voice, your message out there. You never know how it?s going to impact people, where it?s going to impact people. That quote is powerful, Gavin. Thank you.

Gavin: All right.

13271640023_1a1d1ac701_zJohn: Military experience, Gavin. I want to take the spotlight and talk about your time in the Army and the military in general. You?ve been to both Iraq and Afghanistan. You?ve done a lot of really cool things. Let?s talk about one of your most pivotal moments. Tell us a story, Gavin, of that moment and the lessons you learned.

Gavin: You know, John, there are a lot and you guys all know, there are so many things that are happening along the way. But there?s one that just stands out for me and will always be with me my whole life, and I want to paint the picture for you guys. If you were in the military and have served in Iraq — this was the invasion of Iraq and it was about the second day of the invasion — my company commander who is my captain, he?d been assigned a mission. He pretty much took all the assets because he was part of the main effort. They were going to take all the fueling vehicles and all the tow trucks. They were going to go off and do this thing.

Well, I was left as the executive officer behind. As it turned out, our roles got switched. Things happened in the Army and his mission ended up being scratched. The Third Infantry Division tapped me to be attached to them for the entire march to Baghdad. I was a transportation platoon leader. We had big off-road vehicles called PLS, Palletized Loading Systems. They are these big gnarly trucks.

We set off into the desert without maps, without communications, without fuel and without a tow truck. If you got big long trucks, just imagine how hairy that is. We were told by a coronel to march on and follow this column of armor to Baghdad. That was the order that I was given. I literally had to use the colonel?s satellite phone to call back to my battalion headquarters in Kuwait and tell them I was no longer part of their unit. That?s how the conversation went. So I?m a First Lieutenant. I?ve got 120 guys with me.

But this was it, John. Here?s where it had happened. We had outrun our maps. We had outrun our supplies. But we?re out there in a middle of an invasion. We don?t know what?s going on. I don?t know if you guys remember if you?ve been over there but there was a fuel stop. It was the first one in Iraq if you?re coming from Kuwait. It was called Seeder and it became a camp. But in any event, we were there.

My platoon sergeant mutinied on me, in essence. He said that if we went on with Third Infantry Division, that essentially I was going to get all our guys killed. He went around talking about this and this went on for about 12 hours. I found out about it from the squad leaders. I had to, at that moment, relieve him of his duties in the middle and he ended up staying with me for another three weeks as a driver. This was Sergeant First Class. The First Squad Leader ended up becoming the Platoon Sergeant and was an amazing guy.

We launched on through the desert and through that terrible, terrible sandstorm. We were listed as missing in action for two days because nobody could communicate with us. We ended up linking up with our element just outside of Baghdad and delivering the ammunition for the assault on Baghdad.

It was one of the craziest, most unbelievable times. We had all sorts of challenges along the way. But I tell you, what I learned in that moment was that I was responsible, that I was in charged. I had a mission to complete, and I couldn?t let anybody get in the way and that there are people relying on me and so I had to make the decision. So at 23 years old, I had to make that on-the-spot decision. There we no captains. There were no senior officers around to support me. There were no other NCOs I could rely on. It was me and my squad leaders and we had to make it happen.

John: High Speed Nation, if the hair on the back of your neck is not standing up right now, then I got to question because it is just such a powerful story. It?s something that every officer knows and may have to face at some point but hopes they don?t have to. But, of course, when you do, you hope you do stand up to the test. Gavin, you did stand to that test and that?s amazing.

Really, what I pull out of that, Gavin, what I?m really taking that I want to show High Speed Elite what I really think is powerful from that is that you knew what that one end goal was in mind. There were so many distractions coming in. Where?s our comms? Where?s our fuel? Our Sergeant First Class, he’s mutinying on us. What?s going to happen? No, you knew what that one end goal was. You knew what that mission was at the end and you did what had to happen to go from point A to point B without letting any distractions take place in between.

So Gavin, I?m going to ask you to sum it up as well for High Speed Nation. Sum it up for us, Gavin, and really break it down for just one takeaway from that mission.

Gavin: When you are in charge, you need to be in charge. When it’s your responsibility, at the end of the day, it?s your call because no matter what inputs are coming at you, you need to digest it and you need to take that decisive action and then execute.

John: Gavin, well said. That is one of numerous incredible stories I?ve no doubt you could tell us here today. But we are going to move forward now because we?re really trying to encapsulate your journey just as a person from military to now. We don?t have much time to do it so let?s go to your transition now. Take us to that transition out that you had within the military and really walk us through any failures, challenges, obstacles you might have faced and what were your major lessons learned.

Gavin: So John, you know this quote and I?m going to paraphrase it. No good plan survives the first shot, right? So I had this big plan when I was getting out military that I was going to start an authentic Irish pub here in Charleston, South Carolina. It?s an industry I grew up in, et cetera. I had arranged the financing. I was good to go.

I transitioned out of the military in late 2008. When I did, the economy — I don?t know if you guys remember but it?s starting to fall apart. All the guys who were my backers were bankers. Suddenly bankers who had a lot of money floating around simply had none. So what I found was that I was now transitioning out of the military and I was a man with a new plan. I didn?t have one. My plan had fallen part.

The lesson that I got from that was that I should have probably spent more time building my foundation, building contacts here in Charleston before I came in and building up the greater awareness of what my plan B was going to be. That was tough, but obviously you learn to adapt and then move forward. But that was the big lesson I took away was you got to work on that foundation.

John: So Gavin, here on Episode 6, there?s already been some pretty apparent themes that have been developing. One of those for sure is preparation; in a lot of cases, lack thereof, people in the military that are transitioning out. Myself, I didn?t prepare incredibly well. I did have that goal of going to law school about a year or so after I got out and take some time in travel. I went to Guatemala and India and just took some time off. But I didn?t prepare very well. It sounds like you went to that same thing and so many of our past guests have really focused on that.

So if you were going to kind of go back to that Gavin at that period and knowing what you know now, what would you be telling him?

Gavin: What you?re used to doing is making a plan, executing it. If it fails, you?ve got the next higher headquarters to fall back on, right? But there?s no headquarters out there in the real world. It?s just you. So while it?s good, then make the plan and execute as hard and as violently as you can. It?s really important for you to constantly be cultivating your options and cultivating those plan B?s and plan C?s, keeping your options open.

I think that to me was the biggest lesson learned. I came in with sort of hardcore focus, maybe a little bit too focused so that I wasn?t seeing other opportunities that were actually coming my way and going right past me because I was super laser-like focused which is a double-edged sword. It can sometimes lead to a myopic view of the world and you can miss out on some good things.

John: That?s really well said. So Gavin, one thing that really stands out to me from our conversation we had about 18 months ago was your passion. It came through so clearly over the phone lines when we were talking about the direction that you were going and what you were doing. It was just so obvious to me that you had that spark. You had that fire. And here you are 18 months later still rock and roll. Obviously, some lessons had been learned. I?m sure some pivots have been taken, but you have landed on something that you just get fired up about every single day which is incredible to see.

So take our listeners, take High Speed Nation to that aha moment that you?ve had at some point and then walk us to the steps you took that really turned that into reality.

Gavin: I thought I knew what I wanted to do. I was going to go into what I thought was a comfortable business for me in the Irish pub. My current business partner, when I went and pitched him for capital, he made a really good point to me. I think he was the one who turned me on to the aha moment. He said, “Gavin, I don?t think you love Irish pubs. I think you love business.” In that moment, I realized, my gosh, I wasn?t thinking broadly enough. I was sort of containing myself into what was comfortable. In that moment, I went away from meeting thinking, “Gosh, he?s right. He?s right.”

It took me about a year to realize that my real passion was helping others find the capital that I had such a hard time finding and that my real love was watching them become successful through all the lessons that I?d already learned about where to go for money, how to talk to angel investors, how to prepare yourself, how to get your business ready for an investment. Not every business is the type that needs an investment but there are some that do. What you do to to get your business ready for that? What can you expect?

These things are tough to learn on the fly because a lot of times you go in there and if you ruin the moment, you may never get another chance with that investor or with that group of investors. So the stakes are really high. I just found so much love sharing the wisdom that I had spent a year learning. That was the aha moment and I just felt like that was my calling.

John: Gavin, you said the phrase “I was containing myself into what was comfortable.” I love that phrase because just human beings in general, one of our greatest faults. We always love to default to what?s comfortable, to what we know, to what maybe what we are going to be good at right from the beginning. That is kryptonite to an entrepreneur because as an entrepreneur, you need to continuously be putting yourself in uncomfortable situations. You need to be pushing your envelope every single day to be failing, to be adjusting, pivoting, and then going in the new direction if need be.

That?s such a powerful phrase. I do want to say it one more time. You were containing yourself into what was comfortable.

jr_seated_1So High Speed Elite, think to yourself, are you doing that right now? If so, is that really the path that you want to take, especially when you go back and remember what Gavin quote was by the great Jim Rohn.

So Gavin, what I wanted you now — because you have a lot to share with High Speed Nation about what you have going on right now, and I want to give that justice. I want to give that time. So take us to today. Talk to us about what you?re doing right now and how that really can inspire High Speed Nation.

Gavin: I?m like you, John. I?m looking for ways to get out of that comfort zone and to grow and to be more and to say, “What else can I do?” while being focused on my passion. So my world is really in three prongs right now. I have Twin Rivers Holdings. This is my investment partnership where we have major stakes in different companies that range from pizza and restaurants that are scaling to hotel development and others.

Every business, there is an entrepreneur that we’re behind. One of it that was just on the brink of bankruptcy in April. We were able to come in one more time and help them out rearrange, help them get ready, did something, and they just signed a massive contract with Nike. It?s like one of those things and it?s been going on for years. We?ve been slugging it out. That?s the kind of stuff that lifts me up. Here are some mistakes you should know about bankruptcy.

But of all those things and all of these companies that we?re involved in, the one that?s got me fired up the most is where I?m going next which is my branching out and helping entrepreneurs find the capital on a one-on-one basis. I have a blog called Southern Seraph. You can go there and learn more about what I?m doing on that end. I?ve just launched Warrior Ventures and Warrior Startups, and coming soon it is going to be an angel investment arena for entrepreneur veterans. That?s something that?s launching right now. These are all centered around my passion and all centered around what I?m doing right now.

The one business that I got that?s really maybe interesting to your listeners is this Voolio platform that I know I?ve mentioned to you before. It’s a brand new way to monetize your videos. It takes away all of the stuff with go try and get pre-rolls, try and get pop-ups and allows companies to dynamically place their ads inside your video as if it was integrated into the background using an amazing technology. It?s called

For you, John, anybody who goes to gets free trial. I set that up today so you guys could check it out and see if it works for you.

But these are the things that I?m into right now and that?s where my passion is.

John: High Speed Nation, Why not check it out? You never know what’s going to strike that nerve. You never know what?s going to kind of light that spark to get you going.

Gavin, what I love that you do and that story that you told, you give entrepreneurs that need more of a runway more of a runway. So many entrepreneurial ventures fail, Gavin, because they just don?t have the time. They just don?t have the money to actually extend that runway enough where they can actually get products, service to market or where they can justify things. With people like yourself, Gavin, and with companies like Twin Rivers Holdings, that extension is given that then boom, that?s all they needed. Now here comes Nike swooping in and what could have never been now is. It?s just so impressive.

Gavin: John, isn?t that part of the journey?

John: I?m so fired up about it.

Gavin: It is. You can see yourself in that room where in April we?re literally around a room and we were talking about what do we do if this fails? That was the question and you could see it. Guys were talking about “Hey, I?ve got a family to feed. I’ve got to go.” And we said, “Well, what can be?” They came and the passion that was in their hearts and the plan that they put together was so tight. We said, “We believe in you again. We?re going to do it again.” We came to them and now to see — just yesterday, I got this notice that Nike has started in on their beta testing with these guys in October.

Can you imagine? Nike? I mean this is crazy. But those are the types of moments that I live for and that the investors in my group live for and that my partner lives for. We?re out there. I want to be the guy who takes your listeners and connects them with the people that I know now.

John: Wow, High Speed Nation, hear the passion. Gavin, we?re about to answer the lightning rounds where you get to share incredible resources and mind-blowing answers. Sound like a plan?

Gavin: Let?s do it.

John: What was the most difficult adjustment you had to make to the civilian world?

Gavin: Guys, I think the one thing was leaving my buddies behind in the military. When you get out, that sense of values-driven organization, just your friends and the guys that you’re in unit with, that you’re in uniform with, separating from them was the hardest thing. I kind of felt like a fish out of water.

John: Yeah, it?s that camaraderie. You can?t put that into words for people that haven?t been in the military. But I mean you, Gavin, who have been to both Iraq and Afghanistan and then myself who spent 13 months in Iraq, in Falluja, in Ramadi, in Habbaniya — those relationships and brotherhoods that you build during those times are just hard to match.

Gavin, what business advice would you pass along to those making the transition now?

Gavin: Read, read, read. Go on to John?s booklist and start at the top, work your way to the bottom. I mean that, guys, gals, listen, get an Audible account. I signed up for Audible and I listen to business audio books and self-development books constantly. I just cannot tell you how much that has added to my lexicon in business and also how many mistakes that has helped me to prevent from making. So that?s my best advice right now — study, study, study.

John: Gavin, those potholes are everywhere. And High Speed Nation, just why not avoid them if you can. All you have is time. Don?t waste your most precious resource.

Gavin, what?s one of your habits that you believe contributes to your success?

Gavin: I hark on disciplined execution. You make the plan; you stick to the plan. You can adjust the plan but you got to think about it. No excuse, guys. You got to get up every day and you?ve got to execute that plan. So disciplined execution.

John: One of my favorite quotes most recently, Gavin, is “What?s easy to do is also easy not to do.” If you don?t have that disciplined approach, you will find that even though things that are easy to do, since they?re also easy not to do, Gavin, you just won?t do them. That compound effect won’t happen.

Gavin: John, you mentioned the other day, you said something about the 80-20 rule and how you?re sticking to it. I threw a curve at you and you [0:25:37] [Indiscernible] it right off. I appreciated that because I said here?s that guy who?s disciplined. He knows what he?s doing. He knows where he?s going. He knows what?s important. Good job, man.

John: Thank you. But at the same time Gavin, it also shows how much respect I have for you and a lot of other people that come at me with opportunities because I know that if I can?t give you the time that you deserve, I can’t give the right amount of effort into a project, it?s not good for either side of the party. For me, within Entrepreneur On Fire, we know where the bread and butter is. We know where our focus is. We know that if we don?t just continuously drill down into that, then we?re going to start losing our grip on where we are right now which is right at the top.

Gavin, you deserve just the best partners possible. So I will say this though, in the back of my mind, it’s great that you still did reach out to me because I?m already thinking about some people that I want to connect you with that could be great partners for you. So that?s why, High Speed Nation, even if you think you?re going to get it a no, reach out because that person that say no may very likely have somebody that they know that wants to say yes.

Gavin, you?ve talked about a lot of books. Let?s just give one book recommendation for our listeners.

Gavin: Guys, I?ve went through this, I?ve thought about this: Street Smarts by Norm Brodsky. The lessons in there, they drill down. It summarizes understanding things like cash flow. That?s something in the military you never have to worry about. The sales suck of trying to sell yourself out of a bad cash flow situation. The lessons are easy to digest and they are the best. I actually ordered a copy for every entrepreneur that we are invested in. I got a big box of them and sent them out.

John: And Norm is still time relevant, guys. He writes an article for Inc. Magazine every single month, one that I will not miss because it?s always relevant and inspiring.

Gavin, I wish we had more time to talk, my friend, because you are inspiring. We will be talking again. I want to put a spark in your arena to launch your podcast when you?re getting these arenas up in the Warrior Forum and all of these different things.

So Gavin, thank you for being inspiring to us today. Give High Speed Nation one parting piece of guidance. Share the best way that we can connect with you and then we?ll say goodbye.

Gavin: All right. Well, listen, guys, my parting piece of guidance is work on building a network. Use those social sites. Use the ROTC offices at wherever your locality is and ask them to connect you to the business school professors because the professors know everybody. They know every angel investor, every CEO in town. If you can get in and get introductions from them, those guys can light your career on fire.

So you can connect with me at, at; and catch me on Twitter at @GavinMcCulley.

John, thank you, man. This is such a great program.

John: It was so fun. So High Speed Nation, to end with Jim Rohn, because Gavin started with him, “You are the average of the five people you spend the most time with.” You?ve been hanging out with Gavin and myself today. So keep up the heat.

Gavin, thank you. Seriously, thank you for being so generous with your time, your expertise and experience. High Speed Nation salutes you and we?ll catch you on the flipside.

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