Lisa 

I’m Lisa Calhoun, General Partner at Valor Ventures and Atlanta Venture Capital firm that writes first checks into incredible software companies. I’m excited to be joined today on the Atlanta Startup Podcast program by Robin Gregg. She is the CEO of RoadSync, an Atlanta startup. Robin, welcome to the program.

Robin Gregg  

Hi, Lisa. Thanks for having me.

Lisa  

It’s great to see your face. Please tell us more about RoadSync [for] a lot of people who are listening [who] have not heard about what you’re doing [and] have not heard about the company. So, please give us that overview.

Robin Gregg  

A way to think about RoadSync is we function kind of like Square but specifically for the logistics industry. The logistics industry in the United States is a $700 billion industry consisting of everything from trucking companies to warehouses. They really do almost all of their business transactions using paper. Over 60% of their financial transactions are paper-based and that’s really cumbersome. The paper is lousy. It can be lost, it’s slow. It’s just not a great or efficient way to run a business, especially one like the transportation industry that really relies on efficiency and speed. So, what we do is digitize payment transactions. We make it as easy as buying a cup of coffee for us and for truck drivers to pay for things that they might encounter along their loads. Everything from late fees that they might encounter to warehouse unloading fees to heavy truck repairs, and towing, you name it. There are lots of expenses that drivers experience and we make that digital mobile and very easy to use for both merchants and for the person paying.

Lisa  

A $700 billion industry? Wow, that’s strong. Is it a growing industry [or] is it a shrinking industry? What’s the market look [like]?

Robin Gregg  

Yeah, it’s growing now. If you think about it, there’s actually more demand than ever. Amazon is very much impacting transportation and logistics in the United States. Everybody now expects to get their goods faster. That’s creating needs for more warehouses in the United States to stage goods closer to major markets. That means there’s more transportation going on and lots of people are getting things sent to their homes. It is a rapidly growing industry. It’s actually doing really well even [with] the pandemic right now. Not all sectors, but most sectors are really strong, and it’s just super important. It is actually the backbone of our economy. About 7% of the US workforce is employed in logistics. It’s just sort of this thing that as consumers, we don’t necessarily see in experience, but it’s super important for our every day.

Lisa  

You got to your role as CEO through a really interesting route that I think a lot of people admire as an advisor. I would love to dig into that as much as you’re comfortable. There are a lot of amazing advisors in our audience and a lot of founders. And I think that the dynamic between the two is something that you know very well and you’ve been very successful at. Could you share a little bit about how you first found out about RoadSync and sort of your path to the big chair?

Robin Gregg  

Yes, sure. I’ve spent over fifteen years in payments, I started my career after my MBA at Capital One. I had a great six year career there and wanted to do something more entrepreneurial. So, I joined a company called RevolutionMoney which was a seed case back startup out of the Tampa Bay area. That was my first startup experience. I loved it. It was a very interesting ride. It was in 2008/2009 which was probably not the best time to be in a fintech startup in Florida but I learned a lot. We got super lucky and sold the business to Amex in early 2010. Then I joined a private equity backed company called Fleetcor, where a fellow CapitalOne alum was COO. I spent seven years there, we IPOd  and I ended up running a piece of their business in North America. After about seven years, I really wanted to do something entrepreneurial again and I didn’t really know the best way to transition from what had become a pretty big corporate job to back into the entrepreneurial space. I spent a couple years getting to know before I left Fleetcor the entrepreneurial scene here in Atlanta. I actually taught classes at ATDC. I taught a payments class and a distribution class. I tried to get to know some of the startups here and I became an advisor for about three startups in Atlanta usually in spaces that were really connected to the professional experiences I have had. Either small business distribution or commercial payments, or fuel, those were all things that I had experienced from Fleetcor. One of the companies I got to know was this company that was called MyLumper which was the early version and early name of RoadSync. I wasn’t actively involved every single day but I would be a sounding board for strategic conversations and potential partnership conversations. That’s what I did for the companies I was advising and when they went through a period where they needed to have a management change, I was somewhat around the hoop so to speak to take a look and sort of figure out what was the next chapter for the company. Have they built something that was interesting enough for the angel investors to continue to fund? That was how I got involved with a company and ended up taking it over. I just really loved the idea of digitizing payments and modernizing payments in this space. I actually fell in love with commercial payments when I was at Fleetcor. It’s a giant market. I really thought there’s an opportunity to provide better financial solutions to this pretty important piece of the business segment.

Lisa  

Startups are such dynamic creatures. In the beginning, I really think the smartest founders surround themselves with really deep expertise, like you in payments. Advisors who bring so much depth even if it’s in a particular narrow space, in fact, better if it’s in a particular narrow space where they’re deep experts. They know all the people and can walk the company in. I think that’s really exciting. I know a lot of advisors that are around some of Valor’s portfolio. They’re also deep experts. Some of them do imagine themselves in the CEO role often again, or sometimes for the first time. What do you think about advisor compensation? What do you feel is his market? What do you feel is fair as someone who has a lot of experience in that? Now you’re in the CEO chair, so you’re on both sides. I’d love to get your thoughts.

Robin Gregg  

Yeah. I was not compensated with equity when I first started advising MyLumper slash RoadSync. Some of my other companies I was, but not necessarily for them. I think in part, at least in the early days, you are doing it. It’s a little bit of a gesture of goodwill. You have to start by demonstrating that you can provide value and I think something that you were saying earlier was the expertise. The way I found that I could be helpful as an advisor is usually by, you don’t know all the ins and outs of the business, you don’t know it as well as the founders, who you might know better than they do are contacts in the industry, conversations they could be having, how to structure a deal with a particular entity. It’s really being thoughtful about ways you could leverage your expertise in a very discreet way that didn’t require you necessarily to know all the ins and outs of the business. I always tried to find small ways to be helpful and that manifests itself into a deeper relationship where we just realized there was nothing there. Either we didn’t have the right connection, or I couldn’t provide the right level of value or the person just wasn’t interested in hearing what other people had to say. I think that you kind of have to expect that it’s got to start with developing the relationship first before you start to think about the compensation piece.

Lisa  

I love your approach. I think that that is very straightforward. That’s startup friendly, its founder forward. You never know what develops with that kind of an open heart-open hand. How hard is it to open your trusted network to a company you believe in? It’s, as you point out, it’s not really that much time. I really love that. I do know that there are different perspectives out there. I am a really big fan of going down the road a little bit together and seeing what happens. Even as we make investments, that’s often how we approach an investment. “Let’s see if we can be helpful. Let’s see if we can be helpful now and then you’ll know that we are very likely to continue to be even more helpful later if we invest.” So, I love that. I want to bring us back to the current day, though. In this growing business, you raised around, not too long ago, just a few months ago. Congratulations! You guys are thinking full on growth and scale mode. Tell me a little bit about some of the frontier and some of the things you’re excited about for RoadSync.

Robin Gregg  

It’s been interesting. We closed around right before the pandemic. We moved the whole team from in-office to work from home overnight and that was when all our growth happened. I would say about half of our new half of our employees today have never worked in an office together.

Lisa  

Wow. How many [employees] do you have now?

Robin Gregg  

We have almost fifty folks. We’ve really had to embrace the virtual thing. Scaling a business rapidly and this environment has been a unique challenge. It’s exciting, right? But we’ve been really focused on scaling up sales, that was our first focus. Taking the product that we have in deploying it into our core markets more rapidly. We hired lots of sales folks. I really worked on our go to market process. We’re really looking to double or triple our business through selling the products that we have today. We’re also looking at how to expand the product set into other parts of the market. The transportation industry is interesting because it’s highly, highly fragmented. There’s lots of different types of companies that participate in the ecosystem. It’s a very fragmented business in terms of the number of entities. What we’re really working on is finding more and more ways that we can get rid of paper in financial transactions and make it easier to conduct business. Make it paper free and really just provide a better experience for everyone involved. We continue to explore sort of the adjacent markets and figuring out ways we can kind of get ourselves throughout the ecosystem. Our ideal world would be everybody in the logistics industry has a RoadSync account that they can use to get paid or make a payment. We would love to see that one day and that’s what we’re working towards

Lisa  

Are there any large potential accounts in the southeast that don’t yet know RoadSync well enough to say yes? We do have listeners who are well employed, advise, C suite in all kinds of corporate roles. A shout out is always appropriate if there are some major accounts that come to mind.

Robin Gregg  

We’re interested in anyone who handles carrier operations for the major trucking companies or brokers. We’re also interested in any major transportation management or other sort of technology platforms that serve this market. We think that’s a great place to get ourselves perhaps supply our API’s and our payment stack to other people’s platforms. We’d love anyone of that nature. If they’re interested in chatting, it’d be great.

Lisa  

Great. So people who manage carrier platforms, I think, is what you said. It broke up a little bit.

Robin Gregg  

Oh sorry, carrier operations and large trucking companies ,or driver operations, large trucking companies ,or carrier operations and workers.

Lisa  

Awesome. Well, I hoped if you’re hearing this and you’re like, “Hey, why not help out another founder? Pay it forward?” You never know where it leads. Let’s talk a little bit more about some of the human side of your growth: fifty people in a fairly short amount of time. That’s really impressive growth. What are some of the types of people you’re looking to hire in the next six months?

Robin Gregg  

Our current need is a product owner. We’re actively looking for a product owner. We’re always willing to talk to talented sales folks, especially people who’ve sort of done mid market or SMB sales. We are looking for BDR. We’re continuing to grow that team. We will continue to also expand our development team. Engineers as well, but those are the five the main core areas

Lisa  

A little bit about you as a CEO. How do you like the journey of growth as a CEO at a fast-growing company? I mean investor relations, expanding teams, you outgrow the team you built not so long ago. Now, what do you find most challenging and most interesting about the CEO role at a fast-growing software firm?

Robin Gregg  

I think I’ve had to majorly reconceive myself as a leader and manager. When I was in my corporate job, I would never have described what I did as sales necessarily. I spent a lot of time thinking about and managing the business that we had as it existed. Where the mind shift has had to change for me is to really think about how to grow the business and focus my energy on what we’re going to look like in the future. Also, to think of myself more as the ultimate salesperson. I am the head salesperson for the company. I am selling to investors. I am selling to my future and prospective employees. I am selling to our key customers. I am selling to partners. All-day long, that is what I’m doing. To find myself as a salesperson and define that skill set, I think it’s been something that has not initially come naturally to me. But it has been something that I’ve really actually enjoyed and enjoyed seeing that I could do and to kind of put myself out there, I think it’s a tremendously valuable skill set to have.

Lisa 

I couldn’t agree more. I’m working with a really talented executive right now. One of the things he says is, “Oh, I don’t have twenty years of experience in sales.” And I’m like, “The benefit is you have an incredibly sharp mind and sales is a learned behavior.” It is a learned set of skills. As long as you’re a good person, you can build a relationship. You can become an outstanding sales leader. It’s fascinating to hear about your journey in that regard. That’s a great tip for other founders. I’d like to move into a couple more types of tips that I know founders who listen to this program are always looking for. Once you’ve already mentioned is really investor relations. If you’re talking to your younger CEO self, but not so much younger, maybe 18 months ago, what kind of advice would you have for yourself on investor relations? The hunt, the chase, and how to set your mind in the right place for that?

Robin Gregg  

I guess there’s two varieties of investor relationships that I’ve had to think about. One is how do you manage the investors that you have? When I took over the company, I had an existing set of angel investors that I had to think about how to communicate with because I was going to rely on them to bridge us until we get to the next stage. For them, it was about frequent information sharing, being really clear about what was next, being open about the challenges, the misses and to really cultivate trust. I think with your existing investors, making sure that you are very honest and direct about where you’re headed. What’s going on, what’s going well, where you need help? All of those were things that I had to develop in the beginning because I took over an existing investor base that I had to actually develop relationships with. I think that that’s going to carry into the investors that I have now and the investors that I found myself. In finding new investors, I think the thing I learned was that it is a sales process. Do not be too linear about it. When you’re raising a round, you’re raising around. You need to think about what your pipeline is. How many people do you want to contact? Are they buying what you’re selling? I mean, you are selling something. You are selling a stage of the company, a type of industry focus. You really have to make sure that you’re matching what the investors are looking for. Really prioritize having conversations with people who are aligned with what you have to offer. Be prepared to have a lot of those conversations and not just say, “Oh, I’m in conversations with a couple people and I’m gonna see how they go, and then I’m going to find the next couple of people.” I think a lot of founders that I’ve had relationships with, I see that they kind of put all their eggs in one basket. Because they’re on the investor side, their job is to learn as much as they can about you and to be engaging themselves. I think some people kind of falsely read into the positive signals that they might see. You don’t know until it’s done. You don’t know till you’re deep in the process. I think just preparing yourself for having a lot of these conversations with a lot of relevant people, I think it’s important.

Lisa  

You’re absolutely accurate over, “It’s not done until it’s wired.” Sometimes you switch courses with VCs. Valor’s a little bit small for this but I’m not saying never. A lot of times the people who talk to you about how great the firm is and how great you are, are not the people who actually are making the investment decisions. The investment committee level at Valor, generally speaking, you’re speaking to an investment committee member. Once you get past a certain size firm, and it’s not much, that’s no longer the case. Your signals may be all good, but that’s actually what that person was hired to do is give you the green light.

Robin Gregg  

That’s right. That’s right. At the bigger firms, you just don’t know it could be one person who doesn’t like you or you look like somebody else that they went to college with and they didn’t like that person.

Lisa  

In your industry, twenty years ago?

Robin Gregg 

You never know! It could be some phenomenally stupid reason. You just don’t know. I do like especially in the early stage having more focused funds with smaller and smaller funds because they’re able to be more helpful. They’re also you kind of know what you’re getting, right. If you go with a fund that’s fairly small with a limited number of people, that’s who you’re getting. That’s who’s going to pick up your phone call. You’re also going to be a bigger investment to them versus a massive fund where you’re a teeny tiny little check. I think understanding how important you’re going to be to your investment partner, it’s kind of good to know, especially if you’re relying on help and relying on intros. You really want somebody who’s more than just cash. Thinking about that relationship and being strategic and making sure you know what you’re going to get is pretty important, and I think a lot of people overlook that.

Lisa  

I think they do too, and your experience certainly shows. When you say more than just cash, and of course cash flow is really important, but what are one or two things, even just one thing, that your investors have brought to you that has been that has been important to you? I think founders who are before their first raise, they really focus on the money, as they should. They hear that phrase bandied around, value-add platform, all these things. When it comes down to brass tacks as an early stage software company, what have investors actually provided you that’s not cash but has been valuable?

Robin Gregg  

It’s a lot like the conversation we’re having about advisors. Number one is connections and introductions. A fantastic investor will either help you recruit, or will help you find employees or business contacts. People to help expand your industry knowledge, actual prospective customers, you name it. If they are deep in your sector, they should be able to do some of that. That can be a great value-add. Another thing that I found really helpful from my best investors is they have a broader perspective of what similar companies look like and how they perform, either both in our industry or just have a similar business model. You get a lot of ideas from that. You can kind of benchmark yourself against other people. I found that personally really tremendously valuable. One of my investors led me to my series-A base ten partners out of San Francisco, and they really are very knowledgeable about how different business models perform. They’ve been able to bring people that look like me and say, “Hey, this is how they’ve gone about the market. Here’s some of their product extensions to the extent that you look like them. Are these things you’re thinking about as well?” That’s just been really great to expand my thinking. I think those are some ways that can be helpful.

Lisa  

Yeah, not having to reinvent the wheel is wonderful. You’re inventing enough wheels. That’s really cool. It’s very consistent with what we do at Valor. We do a lot of referenceable enterprise customer introductions. That’s thanks in large part to my partner Robin Bienfait’s network. We also do a lot of introductions to talent. Conceptually, we think of, “Can we help the founder recruit their C suite?” We may not be recruiting all of the C suites, it may only be a v1, but recruiting that talent pool around the founder that really can soar with them. Because it takes a team to scale up, the founder quickly runs out of “I can do it all”, especially with a little capital behind. That’s interesting to get your perspective on it. 

Robin Gregg

I think even if they can only introduce you to people even if that’s not the person you want to hire, knowing what the investor thinks is a good COO for your type of business, or good CFO for your stage business, and kind of getting a sense of that profile. Talking to people is one of the best ways I think to figure it out. I don’t care if the person’s in San Francisco or if I’m actually never going to hire them. I actually like talking to them anyway because it gives me a good idea of what this role should look like.

Lisa  

It sets your bar. Presets your bar so you don’t learn by setting your bar by hiring the wrong talent and that’s great.

Robin Gregg  

I always say yes to those conversations. I think that it’s one of those that’s really valuable because I think it helps me streamline role speaking and understanding what I’m looking for and I think it can be very helpful.

Lisa  

Awesome. You are breaking up just a little bit at that distance. I don’t know if it’s the cord. People are pretty accepting of a little digital signal. Sorry, she’s generally pretty clear. Final questions I like to ask people a little bit about Atlanta and the Atlanta ecosystem and how it’s treated you as a startup because there are founders here who are thinking about, “Should I go out west?” There are people who’ve just landed here and are about to start their business here and they’ve heard good and bad. Just your own experience, what do you think about the Atlanta ecosystem for founders?

Robin Gregg  

I think this is a great place to build a business, especially for me. Our business is at the end intersection of logistics and ventech, two really powerful industries. There’s lots of talent, there are lots of prospective customers. It’s a great place to build a business in our space. As far as building a startup here, the absolute only disadvantage is access to capital. I think that that is the only thing that can be hard. But even now, like now you’re doing it on Zoom calls anyway, so I don’t think it really matters. The cost to build a business is pretty low. There are lots of tax advantages. There’s lots of talent. I think you can build a fantastic business for a lot less money in Atlanta.

Lisa  

I couldn’t agree more. It’s definitely why I left my previous company and decided to build Valor in 2015. After almost two decades of working with founders, I was like, “Wow, it is only about the access to capital. The talent, the customers, it’s all here.” Early Stage VC? Not yet enough, not as much as this market deserves but it’s exciting to see even that start to change. I’m all with you on two thumbs up if you’re a founder, you’re thinking about it, the water’s warm. Jump right in.

Robin Gregg  

I think the willingness for other investors and other markets to invest in Atlanta is quite high right now. I even saw it change between my seed and series A. Almost anyone will write a check into Atlanta. The ecosystem is getting to be well known. People like Rob and Kathryn of Kabbage and Kyle at SalesLoft, we’re getting to be known for a place with talent and with good startups. I think that it’s a great time to be building a business in Atlanta.

Lisa 

Oh, I think it’s not a bad litmus test for growth-stage investors. If they’re an AB investor and they will not invest in Atlanta, they are probably not the team you want to be with. That’s just not looking at the market appropriately, the demographic, and the size trends that we’re scaling here, the whole southeast. But, that is not the soapbox for me. I want to talk about you. I want to ask you as a founder, who do you think other founders need to know from your own experience, two or three people that every founder in Atlanta should really make an effort to get in front of and get to know?

Robin Gregg 

Kathryn Petralia of Kabbage. I just adore her. She and I worked together at RevolutionMoney and have been so helpful to me throughout this entire journey. Before I took this job, I told her I wanted to run a startup or to build my own startup and she told me it was harder than it looked. She was 800% correct and has been gracious enough to never say, “I told you so.” when I was crying on her shoulder with whatever problem I had. She and Rob are fantastic and really just know the ropes on scaling a business and raising money. There’s just nothing you can’t go to them about and they’re really generous with their time. I think they’re just fantastic for the ecosystem.

Lisa  

Awesome. Rob and Katherine are amazing. Anybody else come to mind?

Robin Gregg  

Yes. Jeff Levitt is my lawyer at DLA Piper and I think he’s fantastic. He also sits on all my board meetings and has been very helpful to me and [gives] board guidance, just weirdo corporate issues, and raising outside of Atlanta. He has just been fantastic to me. He’s a really super smart guy and has seen a lot of things. I think one of the things that have been interesting is he’s seen a lot of businesses do what I’m trying to do in Atlanta and has that broad perspective and is all about wanting to grow the company because he serves the company and has just been really helpful to me. I think he’s been great and I feel like he’s been a great resource. I love the people at ATDC. Jane and Frank have been great resources. I loved being at ATDC and we were there for quite some time. I think that ecosystem and having the chance to interact with the other CEOs, it’s a great place to start. Plus, it’s cheap, it’s subsidized, and I think everybody should make a little pit stop, if you will, or want to be located in Midtown, you should totally take a pit stop to ATDC. I know we’re all probably going to go virtual here but when we all end up back in offices. It’s a really convenient place to be and I think it’s a good experience. 

Lisa  

Virtual events are pretty amazing, too. For those who are taking notes, that’s Jane McCracken at Atlanta Technology Development Corporation at DC, and you mentioned someone else?

Robin Gregg  

Frank Tighe.

Lisa  

Frank Tighe and Jeffrey Levitt at DLA Piper. So, three people, four people now. It’s awesome that Robin Gregg says, you as a founder need to know. You have your homework. Robin, thank you so much for sharing so openly about your leadership, your journey, the incredible growth at RoadSync. I really wish you the best and love seeing you in the ecosystem. You bring so much light power and energy. I look forward to staying in touch.

Robin Gregg  

Right. Thank you for having me.

Lisa

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