#051: How a $50M Business Cut Shipping Costs by $250K Using ShipPlug – Nick DiNatale Tells All

Typically, if a brand's doing $50 million in revenue, their shipping cost is 10% of that. So let's assume you spend $5 million in shipping. Through finding errors, billing errors, refunds for late shipments, and some of our other services, we typically save customers 3 to 5%. Our culture is, is you need to work as hard as you can to get the job done, or as hard as needed to get the job done. Now, for me, I need to work harder because I don't feel I'm as talented as everybody. But at the end of the day, business is made to change people's lives, to add value. And I think in either direction you can make it work.

Nick DiNatale, founder of Shipplug, is transforming the logistics industry by automating refund processes for high-volume shippers. Leveraging his FedEx experience, Nick spotted a market gap for a service that recovers funds from shipping errors without adding extra work or cost for companies. Since starting Shipplug, Nick has grown the team from 4 to 26 members, focusing on educating clients and building trust to overcome initial skepticism. In this episode, Nick shares insights on scaling a bootstrap business, the evolving role of leadership, and the influence of his hardworking single mother. He also highlights the importance of simplifying complex problems and delivering clear value, drawing inspiration from industry leaders like Netflix's Reed Hastings. Welcome back to Season 2, Episode 14 of the Turning Pro Podcast. Today we have Nick DiNatale, the founder of ShipPlug, joining us. Thanks for joining today, Nick.

Thanks, Ben.

Nick's the, uh, Nick's the VIP of Season 2 of the Turning Pro Podcast. This is awesome. I was looking forward to this. Um, I mean, let's jump right into it. What are you, what are you working on right now?

Well, we're working on a few things. So we're growing our business right now. That's, that's the main thing. Now, as a founder, we've went from similar to Ashley Platter. Last year at this time, we had 4 people. We now have 26 people. So I think my role, what I was working on last year, is different. Now we have ideas how we're going to expand in different service offerings, but now I think my role has changed more into coaching than it has been more so in the weeds.

Do you want to give a quick overview on what ShipPlug does?

Yeah, so we work with high-volume shippers and we automate the refund process for late shipments. We check to make sure you're charged correctly, make sure that you're billed correctly based on addresses. And then if you're not, we file for a refund for that. No work needed, no cost unless we recoup money from the carrier. It gets paid directly back to the shipper. And there's no time needed on their end.

When I met Nick, I, first thing I said to him was like, I, you know, same with you. You talk to a lot of founders, you hear about a lot of businesses. And when I heard what Nick's company did, I was like, oh my God. It's like one of those light bulb moments in the first sentence. I was like, what am I missing here? This sounds too good to be true. You know what Nick said to me? He goes, to be honest, one of our challenges when we talk to businesses is they actually think it's too good to be true. They almost think it's like a scam.

Yeah, because I think there's a lot of sweepstakes offers, free offers online. So when you hear something is free and has no cost, it's a red flag for people. And a lot of shippers that ship thousands of packages a day, they don't know that that's even an option. They don't realize the shipping carriers have guarantees. And so they don't believe it because they've been in the business for 10 years, have never heard about it. It's a free service that takes no time. It's fast. Found money. And so that's, that is our biggest challenge in the sales cycle, is convincing people that, or educating them first that it's a problem, and then convincing them that it actually will work.

Here's a crazy psychology question. Have you ever tested like charging someone an upfront fee just to like, just as another method to basically say to them like, no, there is an upfront cost? Where, you know, people will like assume something's too good to be true, but if they have to put a price tag against it, they're like actually more willing to listen.

Well, at first we had to do that. So our first few customers—

Had to or just?

Yeah, our first few customers we had to because it was too expensive and we needed the cash coming in. It's a fully bootstrapped company. Yeah. So we started the company almost before the software was even made. So there was a lot of cost behind recouping refunds, right? When it wasn't automated. So at the time we made folks pay on a subscription model and pay upfront. Versus doing the found money. Got it.

Can you walk us through an example of— again, we don't need to name the brand's name, but say I'm running a brand and doing $30, $40, $50 million in revenue and I come to you guys. Walk me through how you can help and what kind of money you can save me.

So typically if a brand's doing $50 million in revenue, their shipping cost is 10% of that. So let's assume you spend $5 million in shipping. Through finding errors, billing errors, refunds for late shipments, and some of our other services, we typically save customers 3 to 5%. There's no setup. So in that case, $2.5 million.

But most people don't even know this. Like, it's not just brands, it's anyone who—

$250,000.

Yeah. Anyone who uses like FedEx, UPS.

I don't—

I think there's so many people out there that don't realize that if you buy a product on a website, let's say you buy a t-shirt from a brand and it says this will be delivered on Thursday and that package shows up to your doorstep Friday, you're not really gonna like call and complain to the brand like, oh, my package was a day late, unless it's like medication and you need it. And oftentimes brands won't even have that visibility or pay attention to it cuz like they think customer satisfaction is great, but like there is money to be made back from that package showing up late. So to your point, like education is actually one of the biggest challenges you guys have 'Cause I feel like there's a lot of people that don't even realize the amount of money that they can recoup in these instances.

So in that example, that's a quarter million dollars. I'm talking to the founder, educating them. If it took you less than 2 minutes to sign up for a quarter million dollars, imagine what your time's worth.

Yeah.

Right, if you're gonna say no to that. So that's how we position it. Once it's set, it happens automatically. There's no work needed on the brand's end. Most people don't know that we're actually getting refunds back until we bill them. And then they know, and we have a portal where they can see every shipment. Now we also can compare the carriers for shippers, right? You mentioned some of our customers have really important items, right? Think if you're an e-commerce brand that's doing direct-to-consumer healthcare and you're expecting that shipment to come in to test your blood or whatever it may be, you're going to really track that, but you also then care more about the service than the cost. Some brands buy more off of service. So our software also help aggregate all of our customers to truly see what best shipping company is out of your location.

What does the product roadmap, like the software roadmap, look like for Q3, Q4, looking into next year? What new features, updates are you adding?

So we're adding a few things. We really want to lean into the found money space, right? The no-brainer, it doesn't cost us anything. So we're partnering and we're getting Amazon refunds back now where Amazon has items shipped to them. They miscount the inventory. They send out Prime orders. They get refunds back. They don't put inventory back in place. So we're working in this next quarter to really expand that space because it goes hand in hand. Almost all of our customers that are in the e-commerce space also sell on Amazon. So it's an easy upsell for us, but it's also relevant to our space. So as we go, that's how we're going to scale the business is really looking for avenues that we're already good at and that we can just quickly turn on and add value to our current customers as well.

When you were scaling from, what, 4 people to 26, I think you said, obviously You build a damn good product. And so that's going to just drive revenue up, drive more customers in the door. So you need more people to service that revenue. But as you think about expanding the team, how fast did it grow? How fast did it happen? And what were some of the learnings along the way as you scaled up headcount?

So it happened really quickly. I mean, if you think about it, that's 22 people. We're hiring 2 people a month. Now, what I've learned in that case, how integral it is to train the trainer. Right. Even you can't train 26 people. And if you can, you probably don't have them siloed enough. Like an example, I really have to count on our first developer to train our next developers. That's not my— I'm not a technical founder. So that's not my founder. So I have to first develop trust with our people early on. Right now I have that trust and they have to train. The folks below them. So it's, it's going from being day one. It's my day one. I actually had one person with me. So we had two, two people day one. We're doing everything from sales. We're working on the software, quick, anything, right? And then you grow and we grew with first salespeople. So then how do we generate more leads for them? That became our next task, right? But we're still really in the weeds with everything. Then we hired accounting folks. We hired a legal team. We hired more salespeople, partnerships, more developers. But as you scale, and if you want to continue that pace, it can't be Nick training everybody, right? You hear most CEOs, most of big corporations, or really even when you talk about more than 20 people, you typically can only effectively lead 5 people. Now, there are CEOs that lead 50. I mean, NVIDIA CEO leads 50 direct reports. Now that's not typical and that's not necessarily my leadership style. So that's, as we scale, that's been the biggest challenge is switching that fast. But then also it was good to have great people early on that were really able to train our new folks.

So you, let's, I wanna take a couple steps back. You grew up with a single mother.

I did.

How did that have an impact on your journey?

When you grow up with a single mother, or even I think just your parents in general, but in my case, my mom was the ultimate hustler, right? And she was selfless. So I think when you combine that together and you see someone that every single day was up early to not only get herself ready for work, get you ready for work, she makes sure you're on the school bus. Then I played sports. My mom worked 8 to 5 every day and still was able to manage picking me up, dropping me off, made every single game. So you see someone that gave so much to you and then you saw how hard she had to work. You try to take those values that you've seen and implement that into your life. And unfortunately, because of her, I had a lot of situations that were never afforded to her, right? And that put me in a different space than maybe that she could have ever had. And then you don't want to let those type of people down that have cared for you so much.

What kind of mix was it in terms of modeling yourself after her work ethic unconsciously or subconsciously, just because you're seeing this every day versus intentionally noticing, like, I really appreciate how much she's putting in. I appreciate how selfless she is because as a kid, sometimes you don't— you can't really make those intentional decisions, right? Was it intentional? Was it subconscious? Was it a combination of both?

I think a combination of both. I now— my mom passed away, so I now pick up on things that my— like even little habits that my mom did, and I see that in myself. So I don't intentionally do that. Now, I think sometimes intentionally I do things that my mom did well. But then one thing I picked up on from my mom is my mom had a really high EI. She knew what she was good at, and she also knew what she wasn't good at. And I've always intentionally picked that up from her. And I think that's important in life, is to know what you're good at and what you're not good at.

I realized that, like, one of the first times we met, when he's like, yeah, I hire people who are just way smarter than me, we'll have conversations like, I'm not qualified to be the person talking about this, like, talk to Paula or someone else. Yeah. He knows that, like, to level up, you have to put people around you that are better than you at certain things.

Yeah, I got that from my mom. My mom never made a lot of money, so $30,000 was the most my— and imagine raising a kid on $30,000, right? But growing up, it was— she was also big on accountability, so she would have chores, and it would always be the chores that, you know, were typically heavy lifting, right? I was a much bigger person than her. She hated washing dishes, so I was the dishwasher, right? But I think that's a lesson in leadership. And my mom was good at a lot of things. My mom never asked me to clean because her standard of clean was not— I would try my best, but I couldn't do it, right? I just, I wasn't able to get it as clean as she would want. So that was her job, right? And I think that's what I've picked up on intentionally from my mom is one of the most important things in, in business is putting people in the right position and recognizing what you're good at first. And then as you scale the company, what other people are good at.

I think a big part of that too, also taking kind of from your parents' lessons or your mom's lesson there of modeling to your team, especially once you've hit a certain point, the behavior in which you want to inspire them or that you want instilled in the culture. Growing up, my dad was Italian immigrant, and to this day he works like he just goes in the office Saturday, Sunday, gets back late every night. And he's not trying to do that intentionally for me or anything. It's just how he was raised. And that's kind of what I expected too. That's why you work weekends. That's why we all work weekends, just because like that's kind of what you do. And so now our team is now like 24, 25 people as well. And I used to try to kind of hide that of like, I don't want to show people and demonstrate they should be working long hours. But over time, I think getting more comfortable with like, if that's your leadership style and kind of modeling that behavior that you want the culture to be.

Whether you have to show what good looks like. Now that, that's not our culture because I believe people work on the weekends for different reasons. The reason I typically put in more hours than most is because I have a lot of self-confidence, believe it or not. But I also have a feeling that a lot of the reason I'm successful is because I'm willing to put in the work. There's different levels of talent, right? I don't know if you've ever heard of the book Grit by Angela Duckworth.

Yeah.

In the book, she quotes Will Smith. His talent, he's not a great, he says he's not a great actor, but his talent is he can do the play over and over and over and over until that scene is perfect. Right. So he says, if we're going to get on a treadmill and it's going to be you against I, there's two options. You're either going to beat me and I'm going to die, or I'm going to win because he's going to do it over and over and over and keep getting better and better until that scene's perfect. And I think if you have some type of insecurity about yourself, you're willing to work harder and put in the time. That's why I work on the weekends. That's why I work tomorrow. But I don't expect our team to do it because we have a lot of people on our team that are much more effective than I am in managing their time. So I don't think just because I work on the weekends, I don't think our team has a feeling that that's what's expected. But I do think the team has a feeling that we all need to work exceptionally hard and that they have the ability to work when they want. A lot of people will work on the weekends and a lot of people will take off on the weekends and some people will work on the 4th of July, but they won't work on Christmas. Some people work on Christmas, but on the 4th of July, our culture is, is you need to work as hard as you can to get the job done or as hard as needed to get the job done. Now, for me, I need to work harder because I don't feel I'm as talented as everybody.

Yeah, I think building a culture predicated on results and not time spent is really important. I think for us, especially in a remote world, I'm like, I don't— I can't micromanage you. I don't know what you're doing. Like, you live in other parts of the world. The only thing I can judge is like, did you get your job done or not? I'm not going to ask you if it took you 2 hours or 8 hours, so long as you get it done. And I think that stems back to this idea of using trust as like a main driver when you're building culture, especially remote.

Well, I also think it's also about showing what good looks like. So being a startup founder at first, you both were in the weeds day one. So if someone wants to ask me how to sell our deal or how to sell our, our software, well, I know how to position it because I've done it. If someone wants to ask me about partnerships, well, I've done it. If someone wants to ask me about the software, well, I've done it, right? So I, I do know a lot about it because I was in the weeds, right? And so as, as the founder grows and we're kind of talking about here, that's when I think things need to start to change. And that's when you help develop people and you should know how much time things take, right? Because now I have to hold you accountable. Because I think a lot of times, you know, I'm a big Netflix guy. I love Reed Hastings and I've had this conversation. Every single company, Platter, Shipplug, We all try to hire the best people. Where I found that companies sometimes struggle is firing people that aren't giving it their, their best. And I also think companies struggle with having KPIs early on, right? And what do I expect? What is your job? Because everybody's job changes in a startup. One day you're the partnerships person, next day you're doing trade shows or whatever it may be, right? Because in, in the realm of things in, in a startup, it's so fast and changing. But I think a lot of times startup find— founders forget how to hold people accountable, especially if you hire your friends.

As you're holding people accountable, let's say I'm— you hire me to do partnerships and BD.

Yeah.

And we both either explicitly or, or, you know, we kind of just decided on the side and we had a mutual understanding that I was gonna drive more business and I'm doing okay, but maybe you come in and say, hey, we actually have to like put you on quota. Not in a bad way, just like so we make sure this is explicit. And I'm consistently missing quota. How do you approach that conversation? Is it, hey, let's workshop this together? Is it, hey, you are autonomous, I trust you, but you do need to hit this quota? How do you workshop that together?

So I'm a big believer in being in the game with our team, especially if you're struggling. So I always approach it with, how can I help? Now, the first question I'm going to ask always is, what's your plan? Because no one ever plans to fail, right? Everyone has a plan, right? You don't plan to fail. So I want to understand that the person has the plan. Typically, there is where you can find, just in those conversations, You can find that's probably the issue, right? You don't have a great strategy. So then maybe we talk about the strategy. Now I'll start spending more time with someone. So I make sure that that plan is what they're really doing that they say. Then if that, if I don't start to see progress and when I say progress, I mean results, right? How do we measure the results? We'll really start managing to those results. So how many wins are we getting? How many customers are we finding? How many new deals are we actually signing? Because I think sometimes what I've learned in leadership is that if you have some expectations of people, a lot of times people have expectations, but they forget to tell them, right? If I would say to my sales folks, just go out and sign as many deals as you can. Well, what's your expectation is different than yours, which is different than mine. So No one really knows what they should be doing. Now, I think if you understand the plan, you've already done the job, you should have some type of idea of what a good salesperson would should sell. So then you've worked on their plan and if it doesn't happen and you look at everybody else is knocking it out of the park except for one person, well, you know, maybe your goals are right. Right. Sometimes you can set goals that are so unrealistic that people can't hit them. But you know your goals are right because 1 out of 6 people aren't hitting them. Well, now I'm going to start managing by the numbers. But through that whole time, you have to have the expectation that you're trying to help them. But you can't let in sales and tech in any form of your business, someone sit there and not give it their best, not want to get better. And some people just can't do the job. They're in the wrong job. And so then you have to help them find other things to do.

I want to go back to when you started this company. Like, what was the experience leading up to actually starting it? And like, when did you know that you wanted to be a founder?

I was always very interested in starting my own business. I would say out of college, I thought, oh man, I'd love to start my own company, but I didn't have any good ideas. So I went to work for an accounting firm and that's as far from starting your own business as really you can get from day one. So I worked at KPMG and I wasn't in the right job. I was not meant to be an auditor, especially day one being an auditor. And my college roommate was working at FedEx at the time and said, you'd love the job. We talk to business owners all day and your accounting background, you can really help quantify shipping savings. You can help understand the supply chain. I think you'd be great at the job. And I've always liked to talk to people. So, and I've always liked to talk about business, which is my true passion is having conversations about your business, about our business, about other people's business. And so when I joined that job, that was exactly what that was. And that was over the phone sales. And I had a ton of success right away. We had something called the Big East leaderboard. My first 6 months, you weren't eligible for it. The very first day, I was number 1 in the Big East on the leaderboard. It's a variety of sales activities that they judge you on. So I won that. And once I got a taste of winning, I started moving around the country for promotions. And that's when I really got I knew I was going to be a founder and it took me 12 years, 10 years actually to act upon it once I moved out of Pittsburgh. But all of our customers, we sold mostly in what FedEx considers a small to medium-sized space. So think $50 million in shipping and under. So even billion-dollar brands, they consider small to medium-sized. But when you really get into that $50, $100 million brand, there's still, you're still talking to the founder. So every single day I'm meeting with 5 different founders. Imagine a young 25-year-old kid who didn't have any good ideas, but was really ambitious. You start meeting with those type of people every day as your job. You hear about the struggles, the good times, businesses go out of business. And that trained me on, what type of CEO I wanted to be. I didn't really have still a great idea at first, but it gave me so many different ideas and perspectives, not only about business, but how to lead them. And so I continued to move around 6 times for FedEx, dealing with a large variety of customers. And again, always meeting with the founder. And then what happened is in different sales roles that I moved, my old customers would call me and ask for FedEx help. Right? My bill's off. I have a damage package. What should I do? And that's when I realized what my business idea was. We could really help something that became convoluted, something that became hard to manage. We could help that for the founders. And I now know that every founder needs help with that, that is in the business of movement of goods. So I knew from day one I always wanted to be a founder. I didn't have any good ideas. My job gave me so many different ideas, but I found something that I was good at, and that's when I knew it was time.

There's a lot of flavors to sales. You sell differently than I do, than Ben does.

Yeah.

And some it's more personal, some you're running a script. Again, it depends what type of product or service that you're selling. But how has your kind of style and flavor of sales evolved over the years?

So when you're selling FedEx, you're selling something that's needed and you're selling a huge brand, right? You're calling and you're saying, I'm with FedEx. Well, that's much different than I'm calling with Shipplug. People don't need us, essentially. If, if you don't use our service, you're still delivering your shoe, your shirt, to the end consumer and people don't recognize us. So over time, my strategy had to change, right? How we have to be much better at marketing, right? I'm now a marketer as much as I am a sales guy. So we had to make sure that our brand was relevant, our brand was on point. And that changed because when you're working for a Fortune 50 company, everything's already set up in the sales cycle. You have the presentations, you have the literature, you have the agreements. So in my career, going from a big-time company where everything was set up, I had to change that. And then at FedEx, it was definitely more relationship-driven, where coming to a business where we're having to sell customers that we don't know, we really had to open up cold outreach, right? So now we're building sales teams to quote unquote, smile and dial, where that was not what was taught at FedEx.

Right.

It was more relationship driven. The customers would come to you. People just called FedEx. Now we have to find business and sales through partnerships, through marketing. That all had to change. So that's how my evolution in my sales process has changed, where I've had to almost be an order taker at FedEx and be very responsive, help with customer service. To now being more marketing and sales driven.

So you said it, it took you over a decade to finally pull the bandaid off.

Yeah.

And go for it. What was that turning pro moment for you?

I love to win and I love to try new things. And we want our team, my team is a manager. I want a lot of FedEx, multiple Presidents Clubs, 5 stars. Which that's top awards. But what I realized is that my need to try something new, I, I moved to 5 different cities for FedEx and it was in 12 years and 6 different moves. So you're talking every 2 years getting into a different job. I saw my runway at FedEx in this current role, it was going to be another 20 years. So my urge to get to the next thing, to keep winning, to keep getting promoted, I knew wasn't gonna happen as fast as I wanted it to. And that's what's great about a startup. Every day it's something new. So you start day one, it's something new. Today it's something new. Where that ability, that desire to learn, that's when I knew. When I knew that I was not gonna keep changing jobs and keep getting promoted, every 2 years, I knew that I couldn't just stay stagnant because I'm a big believer if you're not growing and learning, you're dying. So that's when I knew I had to change my job.

And another thing too, which I totally admire, is your ability to bootstrap this business to where you've gotten to. I think a lot in the startup environment in today's world, a lot of founders get glorified based on how much money they've raised, who they've raised it from, and like what news publication gave them a headline to announce it. Were there any moments in your journey where you thought about raising money, or were you dead set from day one that if you can do it on your own, you don't really care what other people are saying to you?

Well, I've, I have thought about it. We, luckily, we were profitable very early on, which helped save the company. We started in what was the worst time to start a company, where FedEx, UPS, all the carriers, they just had no capacity, so they weren't budging on refunds, they weren't budging on claims. But then it slowly switched in the pendulum. So being able to make it in the worst time has now made these times easier. So I've never really considered raising money. Now I will say, I have conversations with our team internally. It can make things easier, but it also can make things harder. At first, if you're bootstrapped, you're working as hard as you can. It's your life savings. I took my life savings into Shipplug. So it's a whole different level of commitment. It's a whole different level of hustle. You have to make it work. Now having that, my co-founder, I always talk about it with her, having that no plan B mentality at first, we would always talk about, what are you gonna do if it, doesn't work out. There wasn't that option. There's no plan B. She's in California waking up at 5 AM. I'm in Florida waking up at 5 AM. We're both going to bed at 8, 9 o'clock at night our time. And that level of hustle, knowing that we didn't have hundreds of thousands, millions of dollars in the bank, we had to make it work. And so that is why we made it work. Is because we had to. Now, I think you can raise money and still have that same mentality. I don't think that's impossible, but I think it's a lot harder to have it. You have the ability though to scale so much faster when you have so much more money to spend. It's easy then to hire better talent. But at the end of the day, business is made to change people's lives, to add value. And I think in either direction you can make it work.

As you've made marketing partnerships, BD sales moves to build the ShipPlug brand, become more relevant, not only to drive new leads but to close deals faster, how much of that is endurance in itself? We're also a bootstrap company, and every time there's like a sale doesn't go through or something's hard, my message to the team and everyone. It's like, we just got to stay in the game. And that's a huge part of it is just sticking around.

Oh, absolutely. So the people that are most successful are the people that can lose the most, right? You're a bootstrapped entrepreneur. You're the ultimate gambler. If you gamble, it just takes one time. Mark Cuban says it all the time. It just takes one time to find the right spouse, to find the right business. It just takes once. Now what I've changed in my mentality is I'm really focused on my success day to day. And what I mean by that is I can control my time. So being a founder, you can control where you're at, what you do. Now I judge my success on if every single day I am as productive and I have the most time booked for my ROI, right? Where's my time spent? How can I get that, that ROI out there? So that's what I try to judge our success on. And then when you focus on the day-to-day, it's easy to get through the times where you don't make that big sale. You don't, because you trust the process. You have this belief that your process is going to work. And you continue if you miss out on the sale, if you lose a big vendor, if someone raises your price, if you get mischarged, if anything goes wrong, you have this belief in your plan. And by sticking to the plan, you're gonna lose, lose, lose, lose, big win. Lose, lose, lose, lose, big win. But that big win and that ability to go through the losses, for me, comes by sticking to that day-to-day plan. And as long as I have a good day today, I know we'll ultimately be successful because I believe in our team first and I believe in our product as well.

My co-founder always said to me, like with the sales, he's like, you got to chase the nos in order to get to the yeses.

It's a numbers game. It's a hustle game.

It's literally, it's an, if you have a product that some people want, there's obviously others out there who can also use it, which then to your point makes it a numbers game.

Yeah. And especially I think in our space where our market is almost every single business, which is bananas, needs a new product. Right. So, but if you think about that, then I think when you do fail as a business, let's just keep it in sales. Why didn't we get this sale? We think we have a product that no one could say no to. So let's say 15% of the people say no. Why is that, right? And then can I take my day-to-day process and, and fix that even if it's 5%? Okay, now I'm up to, I'm up to 90% of the people buy. When can I get it to 100% of the people? The offer is so good no one would turn it down. When, when can I get to that? How can I improve my day-to-day process to not only win more sales myself, but to coach the team to win more sales. How can we get that day-to-day process so good? And it's by listening to the nos. I love when people say no and I want to hear why. And when I've changed this about myself, when we turn people down, I always now give them a reason why, because that's what I want from our team. I want to know why someone would say no to a free product that doesn't take any time and only gets you found money? I would love to know why, and then we can change our sales process.

Very tactically, when do you ask that question? Because sometimes maybe if I'm trying to close a deal and they don't get back to me for a month and I bug them and they say, you know what, like, the time is just not right— that's not like an actual reason. Will you say, hey, can we cop on a quick call? I genuinely—

so at first here, I'll send you a pair of branded AirPods. We do that.

Yeah, we'll send— we'll send AirPods. No, so at first, being a startup, and this is how my sales process has actually changed, I would ask a lot of questions early on because, I mean, if you read the book $100 Million Leads, right, you probably, if you're thinking about starting a company, you could go through your LinkedIn. I have 50 people that might be interested in this. Well, before I start the, the company or before I start working on the product, let's ask them about it. Right. We're personal friends. Let's ask them, what would you do? What would you want? Right. So now you're asking feedback from the first sales call. Okay. Now we, we kind of make the software work a little bit. Now I'm going to call those same people back and hopefully they still want to take a call with me. Most of them will because they care. Okay. Well, we've made this. What do you think about it now? Right. Can we get feedback about it? Okay. Now, We're ready to, we have our minimum viable product. Well, are any of you willing to test it out? Hopefully, because you've given us so much feedback about not only the product, about our sales cycle along the way. So now I have someone trying it out, right? Then once I'm presenting my next sales pitch, I'm going to ask it very early on, but I'm also going to ask for the business much sooner. So I'll typically in our business, we will ask for the business on the first call. If we know that you are not getting refunds from FedEx, UPS, or DHL and you're eligible for them, why are you not doing that? Okay. Whatever reason it may be, we do it for free unless you get paid a refund back. There's no cost. There's no time. And then if they say no, we'll continue to ask on that same call why. Right? Because now the product's built out. We, We know our value proposition. We know what we're good at. So I'll ask for it on the first call if someone gives us a reason. We do get though very few reasons that customers say no. It's typically that they don't think that they will get refunds and we can't do a good enough job of convincing them just to let them try it. That's really the only reason why.

I think that strategy is so underrated in terms of like You said with LinkedIn, but go talk to the people you want to make your future customers to help you form the first version of the product. Have you heard the BarkBox story?

No.

Do you know BarkBox? The subscription? So I have a good friend who was like an early employee there and was telling me this a couple of years ago. They literally went to a dog park and they were like interviewing dog owners, just like asking them, what are you missing? What are you looking for? You know, went back to the drawing board, a few iterations, and then they're like, talking to them about this idea. If we send you products every month, like, would you buy this and use it for your dog? And then went back to the park and asked again. And then when someone would say yes, they'd be like, great, and like pull out a Stripe machine, like, put your money where your mouth is. And they got like their first 1,000 customers before they actually like built, like actually built anything.

They got people to actually pay.

Yeah, like a preorder before they actually had like a product.

Wow.

I had no idea. Yeah.

So it was like they already built their first initial customer base knowing what the product was going to be. And now it's like, okay, if I found my first 100 or 1,000 people that are willing to put money against this, like, now I got to figure out how to tell everyone about this, right? Um, I think one of the things that you do very well that a lot of founders can learn from is just simplifying complicated problems. Like, find someone who wants something and see what they're willing to pay for it, and then give them that thing for that much money. Sounds crazy to say that, but like, most of my successful founder friends are those that can take very complicated problems and make it sound like something that a 6-year-old can understand.

Well, I think that's in any business what you want to do is simplify your solution so it's easy to understand. Now we get pitched ideas from businesses trying to get us to invest in them, right? And if I can't understand your business and how you make money relatively quickly, like within the first few minutes, I'm probably not interested. But I also think if then your customers aren't. Right? If your customers can't identify what value you bring, especially now, maybe if I'm talking to someone that has never thought about shipping a product, they would have no interest, but that's very few people far in between. But like in your business, you can bring the value and people would understand your pitch with the Shopify app within 5 minutes. If you've ever used Shopify, if you're pitching to my grandmother who's never used it, maybe not. But if you, right? But if you get to the right person, and even if you're not at the right person, anybody that has any experience and knows something about Shopify understands your business model. It's easy to explain. It's easy to understand. That's why it's easy to sell. That's why investors want to give you money because it's easy to understand. And I think that's sometimes people try to find solutions to problems that aren't really there.

What about DJ Khaled? What's the significance of DJ Khaled to the ShipPlug team?

Well, we're a Miami company and his slogan, another one, became our company slogan. Because what happened early on, this was probably like month 4 or 5, we had 2 salespeople and we were competitive folks. And he would get a win and he would send an email, say, oh, I got another one. And then I would send one, oh, I got another one. And then, and then we would just start including pictures of DJ Khaled saying it. And so now every win we get, we send out, uh, DJ Khaled with hashtag another one.

Wow.

And so that's become our company's slogan.

You should, you should contact DJ Khaled, tell him your bootstrapped, and be like, we only have room for one investor in this company, and it's you if you want it. And you're another one. Yeah, that would be— talk about a PR story.

There you go.

That might get you more customers than what you have now.

Yeah, I gotta reach out. I mean, he's in Miami, he's everywhere.

I'm sure, I'm sure we could sit here for 15 minutes and I, I think in under 5 to 10 calls I could probably get to someone who knows DJ Khaled.

We actually have, have— I'm sure you have a connection that we're about to get to DJ.

Yeah, I'm sure. Yeah, it's like in real life. Yeah, as opposed to what, the fake version?

I don't know, I don't know if it's in the ether of email threads.

Yeah, we have, you know, you're what, 6 degrees of separation away from everybody. I mean, we live in Miami. We have lots of customers. We have customers that he has sponsored.

So got it.

Yeah.

The thing, the thing that you were mentioning about simplifying your core message resonates so strongly because when it was like 3 or 4 months ago, I think you told me about Shiplog separately. We were hanging out here after an episode. And he explained it in like 2 sentences. I was like, that— yeah, let me talk to him. That makes a ton of sense. I think that was the shortest— it wasn't even a pitch. It was just like, this is what they do. And it was— I think I just finished Hormozy's second book, and it was the classic, like, no-brainer offer, like a home run offer.

Yeah.

And it was funny. It reminded me of— I started in venture right out of college. I did like 3 years investing in brands and some commerce infrastructure and SaaS tools. And as a kid out of college, I had no idea what I was doing. And so a founder would come pitch. And I would dance around all the questions of like, how do you actually make money? And now hop on the call. Like, if I just met Ben, usually the first question is just like, how do you guys make money? I feel like my questions have gotten dumber, but also simpler in a way too, which means they actually got smarter.

If you ask any successful person, very fair.

But 22-year-old Adrian was trying to ask all these technical questions. Now it's just like, what do you guys do?

Right? Because I think, you know, growing up, you hear about all these success stories of these companies going public that don't make money, but then you also hear of the dot-com boom, right, where all these companies, they don't make money, right? That's, that's a point of a business. And I think if, if you can't explain how you make money, your value proposition to the customer is also cloudy, and they, they don't understand what they could use you for.

But what blows my mind is how many founders are currently sitting on yachts in Miami who like sold secondaries or had these big paydays who never actually made a dollar with their business.

Well, they exist, right?

No, far and few between. And of course there's market corrections, and today that's not what people are looking for. But that concept seems so like trivial and basic of like, well, does your product make money or does your business make money? If not, is it really a business? And the— I guess the answer is yes in some instances. But now I think the market is—

I mean, you could be a business that doesn't make money as long as you're a loss leader for something else that's super profitable. Yeah, that's the only way those work. Yeah, there's always a catch, but there's not really a business long term that's going to get passed around private equity deal after private equity deal. It's going to keep being a loser.

Wasn't—

didn't it take Uber, what, like 14 years or something, and then they hit profitability?

The 14—

I think, I think so.

I think though that's a little different when you're talking about a scale of an Uber.

No, no, of course, of course. And I think that was a different game, but I'm just—

conceptually, path to growth.

Totally.

And then I think what they've done, and you know this because you're Uber customers, they've slowly raised the price to where now they're able to be profitable. They use their network for other things other than picking people up.

Totally.

Food delivery. They're getting into packaging now. They're really using their technology even in our space, right? I'm in supply chain to move, connect trucks with people that need freight move. They have Uber Freight, right? They're now using their technology But I think it, it, when you're starting a huge tech company that has no real, like, their gross margin is through the roof. So when you have that high gross margin, fast-growing company, they can lose for a long time because the investor can clearly see a path to profitability. And then you're making the market so much bigger where now Uber is a cash machine.

You've talked about Netflix, you've talked about Nvidia, talked about DJ Khaled, but what larger tech companies do you really look up to, or maybe the founders that you really look up to?

Well, then, A, number one is Reed Hastings from Netflix. I believe in his culture deck. If this guy started two companies, one's pure software, he helps make software for coding to make it easy to develop software. And then Netflix. So the guy's a winner and he, he's not in those spaces. He's not really. He is somewhat a developer. He's not a movie guy. And he led the biggest movie company in the world. But it's all about having the best people. And his culture deck is famous. I try to model a lot of the things I do off of him. Now, I also think, and he says this a lot, You can have people that you somewhat want to be like, but I can't just be like Reed. I have to be like Nick. Now, a lot of things that Netflix does, and I look up to Reed Hastings, is accountability. We're really big on accountability, but also freedom. We don't have vacation days. You can, if you want to take off this afternoon, you're fine. If you want to work on Sundays, You're fine. So a lot of those things align. We, we have the fundamental belief though that the biggest thing that we took away from Netflix is we're not a family at Shitplug. We're, we're not. We're a professional sports team. People come to Shitplug to make a lot of money, right? And I'm a big believer in paying top of market, if not more. But I'm also a big believer in accountability, right? We're, we're in New York right now. So people want to come and play for the Yankees. But why? Well, they pay the most money.

Yeah.

But people know that the Yankees also, because of that, they have a lot of people that want to come work there. Right. But you don't hear anybody saying, man, I wish I wasn't a Yankee. Because I think when you surround yourself with very talented people and everybody's an A player, it makes you better, it makes them better. But that also comes with high sense of accountability. You have to be willing to fire people.

Wouldn't that be your B+? Even that B+ or A- player, kind of like on the 89, 90% range, slips in the minute that you sense that maybe Like, is there a process for let's workshop this together, let's do a PIP, or immediately?

You also need to look at the person, right? An example, I have someone that I started the company with. She dealt when my mom died. I promise you I wasn't the same worker for that period of time when my mom died. People go through situations where they just, even if it's not anyone else in their life that's affecting their situation, sometimes people just get in a slump. So I don't think we're not in the business of just firing people the second they have a bad day, right? That's not because you, you have to care about your people. No one wants to work hard for anybody that doesn't care about them. No one cares what you know until they know you care. And if they genuinely feel that you care about them, right, they want to be held accountable. So what we look for is trends, right? This can't go on for a year. Right, you can't have a bad day for a year. So some of it is measuring stats, being in the game under, you know, I have, I talk to folks that work for us almost every day. So I kind of know what's going on with that sense of feeling. But once I figure out that I care more about the job, your job than you do, like I care more about Ben doing a good job than Ben cares. Well, I know Ben has to go at that point, but it's never just in, in the moment. Now, if you do something totally outlandish in the moment, yeah, we gotta let you go. If you do something unethical, you falsify, you lie, we let you go in the moment. But if you have a bad day, that's not instant termination, but it's because we always care about our people. Everyone that's ever worked at ShitPlug, I care about them so much. I'm so enamored with them making a ton of money. I want them to make a ton of money so they can be happy with their family, so they can live the life that they want to live. But the second I want it more than you, uh, you're gone.

If ShitPlug fails, what's the reason?

It would ultimately be because of myself. Right. I'm the founder. I take— I hire everybody. I coach everybody. I make a lot of bad decisions. So if ShipPlug fails, it's because of me.

This was awesome. I can't thank you enough for supporting the pod. Do you want to just look at this camera on the left and let everyone know where they can find you and what you're working on?

You can find us at ShipPlug.com. For anybody that ships, we can get you refunds for everything that you're due.

Hell yeah. Thanks for coming on, man.

All right, thanks for having me.

That's the pod.