Ep. #77: Tarek Alaruri, CEO & Founder, Stuut Technologies

Cash flow is oxygen, and too many teams are holding their breath waiting on portals, proofs, and “who handles this?” handoffs. We sit down with Tarek, a former TQL broker turned founder, to unpack the culture of persistence he learned on the brokerage floor and how that same grit now powers an AI platform that doesn’t just assist accounts receivable—it does the work.

We start with the reality of freight sales: real-time chaos, creative problem solving, and an all-out push to win accounts. Then we widen the lens to founder-led growth, the kind of leadership that gets teams to feel the mission and deliver through tough cycles. From there, we go deep on AR. Why does a missing lumper fee stall a giant remittance? How do portals, short-pays, and missing documents consume weeks? Tarek breaks down a task-based system that sits on your ERP, automates the repeatable steps, and routes exceptions to the right humans in sales and CS. Think instant W‑9s, dispute drafts with proof attached, and AI-powered calls that surface the exact invoice history mid-conversation.

This isn’t AI as a buzzword. It’s time-to-value measured in days, not months, with reductions in overdue invoices and DSO you can feel in your working capital. We talk hiring A-level engineers who talk to customers and ship fast, the difference between commodity selling and value selling, and how a platform partner like A16Z adds real leverage in talent, BD, and brand. We also draw a firm line on ethics: automation belongs in B2B workflows where it creates clarity and speed, not in consumer collections that cross the line.

If you want practical tactics to close your cash gap, align finance with sales, and keep customers happy while the money moves, this conversation is for you. Subscribe, share with a teammate who’s drowning in AR follow-ups, and leave a review with the next bottleneck you want us to break down.

Follow The Freight Pod and host Andrew Silver on LinkedIn.

Thanks to our sponsors:

Stuut Technologies: Your AI coworker that collects your cash automatically.

https://www.stuut.ai/

Cloneops.ai: Not just AI. Industry-born AI.

https://www.cloneops.ai/

Rapido Solutions Group: Nearshore solutions for logistics companies.

https://www.gorapido.com/

GenLogs: Freight Intelligence on every carrier, shipper, and asset via a nationwide sensor network

https://www.genlogs.io/

Transcript

Sponsor: Stute AI For AR

SPEAKER_01 0:00

Before we get started today, I want to give a quick shout out to our headline sponsor, Stute Technologies. Every week on this show, I talk to operators who are crushing it on the service side but still chasing down payments. That cash flow gap is brutal when you're trying to scale your business. That's why I wanted to tell you about Stute. Stut is the AI platform that does accounts receivable work instead of just assisting with it. Their CEO, Taric, actually came from TQL, so he gets how logistics companies operate. I've known him for years and I truly trust what he's building. What Stut does is simple. Their AI actually collects your receivables for you, not some software that just helps you chase the payments. It literally does the work. It's up and running in days, not months. As an example, Bishop Lifting is using Stut for a 35% reduction in overdue invoices, millions more in working capital, and a reduction of manual work by 50%. If you're tired of your AR eating up time and cash, check out Stute.ai. That's S T-U-U-T.ai. Tell them you heard about it on the freight pod. They'll get you collecting in days, not months, so you can focus on actually running your business. Now let's get this episode started. I'm a very special guest, our new headline sponsor, and also someone who I've been friends with for man, over a decade now. Um through the college years, Mr. Tarek Alruri. I never know how to say your last name. Did I say that right? So Tarek is a former freight broker, freight broker at heart, I believe. Uh he's got everything, all the makeup of what a great freight broker is. And uh he actually grew up at TQL, which means we're gonna spend some time talking about that as I've not had a TQL guest in the past. And now he's the CEO and founder of Stute, uh, an AI business focused on receivables, and we're gonna get into all of that stuff. But uh let's start with your origin and how you got into this wonderful freight industry. So take me back. Um, what brought you to the most fun, rewarding industry in the world?

SPEAKER_00 2:25

Sneakily biggest. I think a lot of people forget how much GDP has passed through transportation worldwide. Um appreciate you having me on. Uh grew up in Ann Arbor, that's actually how we met. Uh a lot of friends of ours overlapped. I unfortunately or fortunately went to Indiana University, didn't have the grades to get into Michigan. Uh, but here I wanted a job out of college. I was a chemistry major, funny enough. Uh you I wrestled at Indiana and you only had to take three tests a semester, so that was much better than having to do a lot of homework. When you go to school like Indiana, you want to also enjoy the campus.

SPEAKER_01 3:01

And that's funny. You and I, you and I had the same exact mindset about college. Find the classes you could do the least amount of work.

SPEAKER_00 3:08

Yeah, chemistry is great. Like if you understand it, you're in the money. It's not like you have to write a paper for 50 pages and then try to turn it in once a week. So that's why I always, you know, devoted time to math and science. But yeah, did that, then wanted a job out of college. And uh there was a recruiter actually at TQL, his name's Jamie Wright. I'll never forget this guy. He was the most persistent person in the world. Uh and the previous two summers, I had done things like trading, worked odd jobs, etc. Uh, and he was just like, hey, if you come by the office, you can make a ton of money. And I was like, I don't believe you. So sure enough, came by. He introduced me to a gentleman who went to northern Kentucky. The guy was W-2ing like well into$200,000,$300,000 a year. And I was like, all right, as a 21-year-old kid, I can definitely kick this guy's ass. Uh, so where do I sign up? And uh moved to Chicago, worked at TQL for about two years, opened an uh office for them in Atlanta, uh, and then ended up in technology. From there, I started a company called Fair Market. Uh, was there for about seven years? We helped businesses like ExxonMobil, Amazon, et cetera, get multiple quotes for things. Um, and then left in 2024, started a company called Stut, which helps with receivables. First time I found out about this problem was doing freight brokering. Uh, and then fast forward about 11 plus years later, nobody had solved it. So started this company, and here we are today with over 100 customers.

SPEAKER_01 4:33

You just did your whole story in about a minute.

SPEAKER_00 4:35

I tried to you can edit it. That's not how this podcast works.

Why Brokerage Hooked Him

SPEAKER_01 4:40

You're not off the hook that easy. We're gonna go back. We're gonna spend some time. Let's we're gonna spend what we're probably gonna do is spend meaningful time talking about kind of TQL and just your freight brokerage knowledge in general, because you weren't just a broker, you eventually were kind of a consultant on the brokerage side. And I I consider you one of the smarter people I know in the industry, so I can't believe I admitted that out loud to you, but uh, I just think there's a lot of insight uh that you have that that will be helpful for our audience, and then we're gonna spend meaningful time talking about what you're building out, stute. Um so so like when you first got into brokering, like what was it about it that you loved? Like what was what what did you see as like the real pull on on why you wanted to do it? Was it just the money or was there something else?

SPEAKER_00 5:22

No, it was the problem solving in real time. Like it's such a complex, I guess, where there's multiple nodes of decision making that you have to do. Like something as simple as like when something can pick up to when something can drop off, and all the crazy shit that can happen, excuse my French, along the way. And then how you have to problem solve it. Uh whether it's like I, you know, truck breaks down, you have to find another truck to come and transload this, and you have to like co-call a bunch of warehouses. It's the ultimate way of like trying to solve a problem that's not digital. Um, and the reason I actually left the space to get into tech was because there's so many things I saw that I was like, wow, you know, as a kid coming out of college, I thought a lot of this was more digital. But the fact that you're faxing paperwork over for like insurance claims well into the hundred thousand dollars, like this is crazy. Uh, let me learn a little bit about like how to build technology, the secret sauce there, um, and then come back or try to fix some aspect of this someday.

SPEAKER_01 6:19

And and what were what would you say were the skills that because I know you I don't know if you were president's club at TQL, but I know you did well. Um, you were a successful true freight broker. Like you weren't somebody just managing, you were someone who was actually hitting the phones, developing customers yourself. And it's not often I get to sit in front of someone who actually did the job.

TQL Persistence And Sales Muscle

SPEAKER_00 6:39

Yeah, I mean, and so great question. You get in there, I like my biggest thing is I would get in there before everybody else, and I would be the last to leave. Uh and I think when I was working at TQL, they had a really good training. Well, I would say they had a great training program where you essentially sink or swim. Well, I say great training program is it's kind of like startup world. But you're there for like two months and then you either make it or you're gone. Uh, and I love that kind of environment. It's not for everybody, but you know, I was helping underneath another broker, learned how to do it, and then just started ripping dials into larger businesses. I think one of the unlocks that I had uh comparatively was at the time that I worked there, not a lot of people had called Fortune 500 companies, which is to me was kind of a crazy thing. I don't know if it's still crazy in the freight industry, but it was like, hey, you know, XYZ giant Fortune 500 or Fortune 50 company probably moves stuff. Uh and you know, it might be somewhat regulated, somewhat not regulated, but you could probably figure out that it gets from point A to B. And uh let me help you do that. And I think really just like little things to land some of those customer accounts, like you know, calling ahead of supply chain every day for the same time for a month straight, and then sending a follow-up email until they took a meeting with you is is pretty fun. I enjoy that kind of stuff.

SPEAKER_01 8:01

It's so funny you say that because like that that's like to some extent, those are some of the things that for the longest time I was like, this is what I hate about TQL. This is what I think is wrong about sales and freight brokers. I'm like the fact that you'll call someone every day at the same time, even though they don't want you to call them anymore. You just keep calling them for a month straight until they give you a load, is like to me, I was like, that's so it's such poor etiquette. But like it worked, right? I mean, like, was there any I mean guys ever tell you like Yeah, I mean, all the time.

SPEAKER_00 8:34

Also, it's like if you're in those shoes, it's super annoying. But at some point, like, you know, I'm sure you get cold calls, uh, you know, in your career, like for sure. Whoever hits you with a good cold call, I'm like, wow, this is awesome. Some like gentleman hit me the other day for a recruiting agency, just out of the gate made me laugh. He was like, My dog died. I was like, what? Like just random guys calling me, like, okay, that's kind of weird opening, but I'll take a second to hear what you got. Uh but I think it the persistence that it teaches, because it's you know, very sink or swim mentality, at least when I work there, um, helps in a lot of aspects. Like when you're starting a business, as I'm sure a lot of your listeners have done or might even do, you have to take that same approach to a lot of other things that might not just be sales, whether it's recruiting, fundraising, you know, receivables, like getting your customers to pay you. Um, so I think it teaches a good muscle. Obviously, if you're calling a customer to sell software probably uh every single day at the same time, you know, it might be received well, might not be received well. But I mean, you know, persistence pays the bills. And, you know, I think one of the most famous tech companies, Oracle of all time, is known for their sales muscle and being one of the most aggressive sales companies. And look at where they made it.

Founder-Led Growth And Culture

SPEAKER_01 9:48

Yeah, it's it's so interesting because like there's there's two sides to every coin, right? And like I agree with you that like that the idea of learning to not take no for an answer, and that that failure is not an option, and that you're whole you're spot on. That it's not just sales. It's more what more is more important. The better way to say it is that sales is everything. Recruiting is sales, receivables is sales. Um, so many functions in any business are truly sales because it's about how can you get someone on the other side to give you what you're looking for or to give you what you need. Like when you think about receivables, you don't think of it as a sales function. It should just be like, hey, you owe me money, so pay me on the terms that we agree to. But like that's just not how the world works. Like there are other things going on in someone's business, there are other priorities they might have, and you have to do this dance to figure out how do you get their priorities to align with yours to pay you in a reasonable fashion. And then in your business, it's like, how do you leverage the right resources to do it as efficiently as possible? But we're not going to talk about that yet. So um but but I I think it's like the I've I've been on the record state and and and TQL is such a controversial and controversial, maybe not the right word. Yeah, maybe it is topic in in the freight industry. Because and and I'm in the camp that 10 years ago, if you asked me about TQL, I would have said, like, yeah, they're they represent like so much of what's wrong with the industry. Today, there are a lot of things. I look at TQL and I'm like, they are pretty dang good at what they do. And you know, I remember I'm on the record before I got fired of telling my partner as part of our hiring plan, I was like, I want us in our sales to be more like TQL. I thought we coddled people way too much, personally, like me. And and our approach was like we would make excuses for why people weren't succeeding in sales. And those excuses, I always were focused on us. It was like we didn't train them well enough. We didn't give them enough marketing material, we didn't give them enough this, we didn't give them enough that. And that's why a year in their numbers aren't good. We should give them another six months before we pull the cord. And what ends up happening in that type of environment is you just have dead weight that sits around for a lot longer than it should. And I remember telling my partner, like, listen, we only have 30 salespeople. I want to hire 75 salespeople this year just on the customer sales function. And I want it to be like a TQL environment where it's sink or swim. Like within two months, we should know if this person can cut it or not. Can you talk like that environment? Like what were some of what you felt were like the big pros of that, but also what were some of the more challenging elements of it, like some of the drawbacks?

SPEAKER_00 12:32

I think with everything, there's a positive and a negative. And so, you know, it's like anything in life, and it's not just the freight industry, it's what I learned that deals with like faint or swim mentality training, et cetera. Um, you know, if you look in tech, for instance, there's a gentleman, his name's Jason Lemkin, but he has a thing called Saster, and he writes a lot of content on like best practices for tech companies that are fast growing. And he a couple of weeks ago actually published an article about like when do you know it's time to fire an executive or somebody? And the resounding of like polling a bunch of executives was actually like when you have that gut feeling that somebody's not gonna make it, there's really never a time that they're gonna make it. Like you've never looked back on somebody parted ways with that you've had like the intonation to be like, or the like internal feeling where you're like, I just don't know if they're gonna make it. There's really never been a time in your career where they just like all of a sudden become your superstar employee like eight months later. Um, and I think a lot of that aspect, like the more I think about is like not everybody's a really good fit for the companies that they work for and the profiles of the companies. Like, I do not think I would do well in a lot of companies, but then I might excel at a company like TQL just because of the culture that I'm in. And I don't think a lot of people would work work well at Student. Uh but they might work really well at like an open AI, an anthropic, or a different type of company just based on the culture that you built. And I so to answer your question, I think, you know, there's plus and minuses with everything. I think one of the things it does is it weeds out employees who should not be there, especially if you're looking at a you know space where you're taking people that are more junior, you're trying to have them learn skills. You kind of figure out who's a self-starter pretty quickly and who's not, because they figure ways around the system uh or through the system and they're pretty successful. The other thing is, you know, it teaches that persistence. I think, you know, because of that and where the space is today, I think things are changing in terms of what you can automate, what was low-cost labor, whether it's in transportation, whether it's in other industries too. Um but I think a business like that's always going to be successful as long as it's like founder ran and there's the core DNA of the people who are like built that around it because it's gonna gravitate to people that are like that that are successful. Sorry if that's like a roundabout answer.

SPEAKER_01 14:47

No, it's not. And it brings up an interesting comment that someone else made. There's there's a CEO, I don't want to out him or say his name because I don't know if you'd want me saying this, but he he's one of the fastest growing brokers in the industry, a good friend of mine. And he basically was like, I think one of the pieces of the pie that some of these MA deals don't understand is that founder-led growth is like the key to sustained growth and brokerage. And as soon as you remove a founder, you're likely in a lot of trouble. And so I'm curious your comment just now of like as long as the founder is still running the business, like talk to me about why you think founder-led growth is important and what like a little bit more meet on kind of that concept.

Sponsor: Rapido Nearshore Talent

SPEAKER_00 15:34

Yeah, I guess to give you a direct example in tech, you're essentially building a product from scratch and you're getting customers early on to believe that you can solve a problem for them and the magnitude of the problem. Uh and you know, even if it's a company the size of Databricks, ServiceNow, et cetera, like somebody still wants to talk to the founder. And some of the companies that sold early on still want to call like a TQL example. Like, you know, one of their biggest customers probably wants to talk to Ken Oaks on the phone at least once a year. And so when you remove that, you're also, you know, changing the DNA or changing the company. And so, you know, I'm a big try to lead by example. Like I still make cold calls here, I still actively close deals, I chip some things in coding every now and then. Like, you know, try to lead from the front is something I believe in because it's like, you know, having worked at TQL, everybody kind of led through the front and you kind of worked with people that fit the same mentality. And then I've worked places where they don't lead from the front, and you have people telling you what to do, and that's like the worst thing ever, at least for me. Uh, and so, you know, huge believer in that. And so I think if you're kind of cutting that out or trying to change the culture, you're gonna have a lot of employees who believe in that philosophy. And I and it's pretty much true for other verticals than transportation, software, AI, et cetera. Like you see everywhere, you know, like Lou Lemon, founder, highly uh a character and probably not saying the best things and you know, might not be the best leader for some people, but he's trying to get back involved in the business because he sees the space in the future that he's trying to get involved in right now. And he's waging, like, I think a proxy fight for it. But you see founders come back to some of these businesses and the DNA is strong and the team believes in them and they believe in what they started. And so I, you know, I think it's really damaging when that happens.

Making Teams Feel And Perform

SPEAKER_01 17:21

Okay, let's take a quick time out and give a shout out to one of our sponsors, Rapido Solutions Group. Rapido connects logistics and supply chain organizations in North America with the best near shore talent to scale efficiently and deliver superior customer service. Rapido works with businesses from all sides of the logistics industry, which includes brokers, carriers, and logistics software companies. Rapido builds out teams with roles across customer and carrier sales and support, back office administration, and technology services. The team at Rapido knows logistics and people. It's what sets them apart. Rapido is driven by an inside knowledge of how to recruit, hire, and train within the industry and a passion to build better solutions for success. The team is led by CEO Danny Frisco and COO Roberto Icaza, two guys I've worked with from my earliest days in the industry at Coyote. I have a long history with them and I trust them. I've even been a customer of theirs in Molo, and let me tell you, they made our business better. In the current market where everyone's trying to do more with less and save money, solutions like Rappido are a great place to start. To learn more, check them out at goropido.com. That's gorapido.com. Now, let's get back to the show. Yeah, I agree with everything you said. The other thing that I'll add is I feel like, and I just was thinking about this yesterday, and I think it relates, is part of the founder's job or part of the founding team's job is to make the employees feel something. Like feel something that gets them inspired, motivated to like show up and do the job. And it's it's not like in the hand, it's not in the job description of a founder, but like it is your job to make them feel. And I feel like if you're doing a good job as a founder over time, that permeates throughout the business, and others can step up and take on that role and also help people feel. Like, because as you grow from one to 20 to 50 to 100 to 500 employees, by the time you're at 500 employees, it can't just be one person who's who's gives makes you feel something when you show up to work every day. There have to be 50 or so who are like fully bought in and they they learn from the first person, you know, leading from the front. But I feel like the challenge is when you remove a founder, oftentimes it kills a little bit of that because you're not you don't have someone showing up every day who feels responsible, who's responsible for making people feel connected to the business, feel motivated and inspired to like. Like live out the values of the business. And if that kind of spark goes away, if that you know flame goes out, eventually it goes out for everyone. And that's why you see, I feel like a lot of times these businesses, when the founders leave over time, they just start to stagnate. And once they stagnate, top people start to leave, and then eventually you're just left with kind of what you hope is I don't know what you're hoping for, but it it's not great. I don't know if that makes sense what I'm talking about.

Frank Slootman And Execution

SPEAKER_00 20:27

I will caveat that. Have you read Amp It Up by Frank Slootman? That's an unbelievable book. So he came into Snowflake after uh it was incubated in the Bay Area. Uh, but he essentially built the business to who it is or what they are today. He left recently. But his whole book, it's about 250, 300 pages. It's great. It's just like there's no time like the present to have that conversation to do it. We need to operate on like maniacal focus and maniacal urgency. He wasn't a founder of the business, but he made the business to who it is. And a lot of the people who like came to work at Snowflake are huge Frank Slootman fans and they wouldn't work for anyone else. So I think there are exceptions to the rule. But to your point, like people are bel people are joining a company because they want to believe in the mission, the core values, and like what the outcome is that the team's all aligned on. And you know, I think right now it's maybe trending differently, but if we look at the last like 10 to 20 years of hiring, it was definitely an employer, employee market versus an employer market. And so, you know, as a founder, you owe it to the people that are putting years aside to your life that, like, hey, you're gonna try to deliver on this mission and I'm gonna give it everything I have. Because a lot of people that join you early on, they can work anywhere they want. They don't have to work at, you know, Stut, Fair Market, you know, Molo, anywhere like that. Like these are smart people. And so you owe it to them more than they owe it to you. And so 100%. One of the things you have to do is you have to deliver on that. And so, you know, to your point, though, when some of these companies rip out founders or the founders goes to Hawaii and then lives their best life on a goat farm, they lose that bit of the culture.

SPEAKER_01 22:10

Yeah. And I agree wholeheartedly. I mean, I I feel like I remember that. I think that was one of the things I felt like we did really well early, and at least early, was like we felt so responsible for the well-being of our employees that it was like it was like a real feeling every day of like we have to give these people the best possible experience or they will go somewhere else. And I'm curious what you're seeing in the market today, because you know, five years ago, it was definitely a fully an employee market. Now all you hear about our layoffs um largely. And I'm curious, like, has that has there been a shift? Are we it are we back into more of an employer's market that you're seeing?

SPEAKER_00 22:52

Uh to answer your question, it's a great, great, great question. I think it's bifurcated. Um, there's always a place for the best sales reps and the best engineers, no matter what you do. Like the 10x sales reps and the 10x engineers. One of the biggest misconceptions I always see is when people have like layoff lists or they were at another company. It's like, if they were so good, why are they leaving? Usually there's one of two reasons. One, they were probably not a fit for that culture. They might be kind of a wild card. I think everybody knows someone. I might be one of those people at some point in my life. Uh, or the other one is just, hey, you know, this person's looking for a change of scene. So usually if you can get one of those 10x people, it's great. Um, you know, and then on our side, we either see this entry-level sales role right now, which is if you look at like our entry-level sales team at Stute today, we have two people that went to Harvard, one went to Michigan, one went to Bowdoin, which is pretty crazy. And they stumbled into sales just because there's really not anything out there. And so I would say I think on that aspect, on the non-engineering side, it's pretty hard. Um, but that being said, you know, our more junior engineers, uh, you know, we get in very competitive situations if they're leaving like top schools like Cal.

Sponsor: Genlogs Intelligence

SPEAKER_01 24:13

Or is that is there not like a fear? Because that actually reminds me of something that my stepmom, Marianne, who who led Coyote's hiring efforts for I don't know, the entirety of the business while she was there. In 2008, we were coming out of that recession or 2009, and I remember she told me she was getting a bunch of finance people applying to work at Coyote because they couldn't find anything else. Like these finance undergrads applying to be freight brokers. And she's like, I never wanted to hire any of them because I just knew I'd have them for a year or two, and then as soon as the market turned, they'd be gone uh off to whatever finance job they could get. I'm curious, like, you know, you've got these Harvard and then you know, even better school Michigan and Bowdoin. Um but like is does that fear exist there where it's like, all right, these guys are gonna put in time until they find something better and then they're off to the races, they're out of here.

Why Startups: Fair Market Story

SPEAKER_00 25:12

Sorry to hop in there. You know? No, you're good. Like one of the guys he's followed me for two of the companies, like Fair Market in here. Uh his name's Mike Metcalf. Like, he sold Cutco for a while and then he just got into software sales. Uh, but he loves sales versus you know, someone who might have an academic pedigree or might be in finance, like they might actually love that career change and love sales. Also, you might get people who want to be in sales and graduate, like some of these sales schools, like University of Tennessee or whatever, and then they get into sales and they realize they hate it. Like sales isn't for everyone. I'd say probably like you know, one out of 10 people make it to a high level.

SPEAKER_01 25:50

Yeah. How do you feel like sales selling software is different than selling freight? Great question.

SPEAKER_00 25:56

It's um it's not a commodity. So the biggest thing is you have to you have to figure out what a customer is trying to solve from a value perspective and a business outcome perspective, and then you have to align it versus when you're selling a commodity like um commercial real estate, freight, you know, something like storage, GPUs, stuff like that. You're selling more like how am I different, how am I better, and more relationship selling versus, you know, it's one of the things that both like the last three companies I've worked with in the tech space or worked for is you have to find someone who has budget, you have to align, you have to put together like a very good, comprehensive, this is how we're gonna help, this is the business impact, here's the metrics we're gonna track. If you're selling to the enterprise, here's like the hundred plus fucking people that like sign off on this and see value. Um, versus, you know, freight, you can just make a call to a transportation director on a right day, and he might send you a load from a company like Target.

SPEAKER_01 26:55

Yeah, I mean, how hard was that for you personally? Going from the world of like, I'm just gonna bang on the phone until someone gives me a load and I got to get a load in the next two weeks, to now it's like it's expected this is gonna take at least three months to get the 10 decision makers all to even look at my proposal to maybe have a chance to sign this deal. Like, what was that for you personally like to kind of navigate?

SPEAKER_00 27:17

It was definitely a learning adjustment. I had great managers and great people I worked with who like, you know, I wouldn't say I'm the easiest person to work with sometimes and the smartest person. And so they, you know, helped bash it over the head. But I can remember my first manager, his name was his name's Grant, but he was hilarious. And he, I mean, he helped a lot. It was just like, hey, dude, you're not selling like something that somebody can just pick up the phone and buy today, right? We need to solve a problem for this customer. Uh, and so, you know, I was very fortunate to work at a company. We got bought by IBM, but I learned a lot. Like, you know, there's pluses and minuses, like I said, of everything. And like, you know, as easy as it is to call, say, that transportation director at Target and maybe get a load, it's also equal and as competitive to get in the door or lose that business. You know, where like being in tech, it might be harder to win a deal, but making sure that you deliver on that, there's a lot of different components that are outside of your control that you don't have in freight.

SPEAKER_01 28:11

And that's gotta be hard because in freight, like, yes, there are certain things that will be outside of your control, but most problems as a freight broker, like if you're the salesperson managing your account, you can solve most problems if you're willing to put in the time and effort. Like truck falls off your load. Maybe in you know, in TQL world, you might have booked that load yourself. In in the Molo world, there was a carrier up who did it. But even if it's seven o'clock at night, if I want to solve this problem for my customer, I can go find a truck myself, even if it's not my primary job responsibility. But in in in the software world, like you know, if if if you agree to something and then you realize like this product hasn't shipped yet or this part has like you're not there yet, like there's only so much you can do. In fact, it's maybe nothing. Like, what is that like vaporware?

The AR Problem Worth Solving

SPEAKER_00 29:01

There's a lot of famous there's a lot of famous tech companies that have, if you search online, that have built vaporware and massive businesses on vaporware. Um but I think you know, one of the reasons I like my entrepreneurial journey started was because I wanted to manage more of the full life cycle and being able to like help deliver. And you know, to your point, when you're in sales for a tech company, you don't have control over that. You want to like learn how that you can actually have control, how you can code, how you can work with a team, how you can build product, etc. Um, so that part is challenging. I do think, you know, one of the one of the biggest things that I've seen as like an indicator of success is how quick people are willing to like learn the use case and sell exactly what you're supposed to sell in tech. Like, what is the exact business case that everyone else is selling, and how do I do that per a playbook? Where I think, you know, transportation or more of like a commodity sell is like how do I go outside the box a little bit and think creatively. Um, and so you know, I think that's one of the nuances is like how do you learn the basics blocking and tackling in a value-based selling, and then how do you go from there? It's a little bit challenging. Um, and then there to your point, there's a lot of stuff outside of your control, the bigger businesses get. Like, if you're selling for Microsoft, like, you know, you're probably nothing's in your control there.

SPEAKER_01 30:19

Yeah, that makes sense. So I wanted to spend a couple minutes talking about just like the career of being a freight broker before we move off of the freight broker concept. So, like again, because you you spent a couple years after your TQL time, you actually consulted for a broker, right? Yeah, when I was like you helped them.

SPEAKER_00 30:42

I was starting fair market and I uh needed to pay some bills. So I was helping one of my friends just.

How Stute Works With Your ERP

SPEAKER_01 30:48

So that was that OTR transportation. And so I'm I'm curious, like from your perspective, like what are some of the most important elements? Like when you're when you're thinking about if you were if someone came to you and was like, hey, I'm gonna start a freight brokerage tomorrow, give me like the top pieces of advice you would give for for how I could be successful. What are the from a system standpoint, not like what companies should I partner with, but like organizationally, what am I looking for in terms of people? What what what kind of structure should I create for the business? What's most important for me to get going? How would you answer that?

SPEAKER_00 31:22

Uh so there's a couple things, right? I think your first question is like, what would you use from a people perspective, which I think we spent some time talking about? I'd say like number one on people, it's like, you know, Bear Stearns. I don't know if you've ever seen this floating around. It's like, give me poor, smart, determined. Like that is a great profile. Somebody who's hungry, somebody who's sharp, don't really care about their pedigree, throw that out of the window, but somebody who's just determined to make it in life. Take that person anytime, despite age, any like, you know, you can find somebody straight out of college, somebody who's never gone to college, somebody who's like wants to transition careers, uh, just that kind of profile is just amazing.

SPEAKER_01 32:01

Um Yeah, Ted Alling actually used this very similar analogy where he said, I want people with a PhD, poor, hungry driven.

unknown 32:09

Right.

SPEAKER_01 32:09

So it's gotta be the same concept.

Tasks, Exceptions, And Automation

SPEAKER_00 32:11

And then I think one of the things that you know I is consistently evolving is just the technology stack that I don't think a lot of companies understand that they can leverage. And when you're you know, a company of our size, we're about 50 people now, uh, you have to get the most out of what you got. And so trying to automate as much as they can, like, you know, not to plug a tech, but even on the HR payroll side, like the some of the stuff that's out there now, whether it's like deal, rippling, etc., tools, like you can just one click onboard an employee or you can one click pay pay like 50 people in one badge. Uh, you know, rewind the clock 10 years ago was not the case. And so whenever you can figure out like what are some roles I can push off, or what are some areas of leverage that I can help with, you know, and I think there's always like the sexy buzzwords of AI, AI. But if we break it down from like, okay, on the marketing side, there's probably some tools that can create content for me. There's some things that can do, like, you know, brand recognition, whether it's like podcast design, et cetera. So can I use some of that stuff at a much lower cost than like hiring a third party? And then on like the demand gen side, hey, there's like we're using a tool called Nooks, but you can parallel call like eight people at once from a local phone number. So like I can cold call you and it can call you from a local Chicago area code. And I can knock out eight of those at a time. So like that's and is it you it's you or it's a bot? No, it's me. It'll just all of a sudden connect and it's me. Because like you don't want to cold call through the bot.

SPEAKER_01 33:44

You dial what happens if you dial eight and eight answer?

SPEAKER_00 33:47

Uh yeah, I mean, that is a problem. You got to be quick with like hanging it up, and you can't like multitask when you're on this thing, but it's great.

SPEAKER_01 33:54

Um efficient.

SPEAKER_00 33:57

Yeah, I mean, there's things like that, and then there's some of these like AR SDR tools that like will write emails based on LinkedIn profiles, show you selling indicators. So I guess my whole point there is like a lot of this demand gen, marketing stack, a lot of that's automated. But then I think you know, from a brokerage perspective, you know, the whole concept that, and this applies to accounts receivable, which we do, it's like AI is taking your job. I think that's I think that's very ignorant. Because at the end of the day, both brokerage accounts receivable, they're customer-facing functions. And there's nothing worse than when your flight gets delayed and you have to call like Delta, et cetera, and then you're waiting online for 40 minutes and then you get a robot, like that just makes you want to throw your phone through the wall. And so, you know, there's nothing better than just like an old human. So as long as you can put the human in the capacity to be able to do more for your clients and then automate around that. I think right now versus where it was even five years ago, there's been a lot of different developments.

SPEAKER_01 34:59

And how do you even think about like deter like creating the right structure to evaluate where to plug in automation technology or AI? Because I mean, it's gotta be hundreds of solutions being thrown at you in every realm of the business. And like, you know, as a founder, you're now doing this. I'm sure you've got some some of the stuff you're building yourself, but I'm sure there's plenty of opportunities in your business. Like you mentioned, company like Nooks. Like, how are you evaluating whether to work with Nooks versus one of Nooks' hundred competitors that all have slight variations to how they execute and perform the tasks that you're looking for? Like, how do you think about just approaching that as a founder or as a CEO leading a business?

Who Owns Customer Conversations

SPEAKER_00 35:46

There's a great question. I and this is a probably a silly answer, but I defer to the team. Like, I'm not gonna tell them what to buy. I'll give you a great example. I don't know. I'll give you a great example. Like uh some of our newer salespeople are like obsessed with this company and they reached out to us cold. If you look at the market, it's like an AI SDR. So it acts like an SDR, just like an entry-level sales cold caller, email, or person. Uh, but it's an AI tool. If you look at the market, like our investor, Andreasen Horowitz, has invested in one, and then there's a couple others that I would say are like category leaders, but our team absolutely love this one that cold outreached. And so, you know, I'm just like, all right, go ahead and use it. And let's see if we can get some results. And then if you don't like it, then we'll try something else. So, you know, I think the whole the whole world where you have to do like a six-month implementation, they promise you, that's not modern software. And if somebody's selling you than that, that's not something you should be using. And also, if you're the CEO that's trying to dictate what your tech roadmap should be, then you probably need to look yourself in the mirror and let your team run. Okay. That's my answer.

SPEAKER_01 36:55

Well, last question on brokerage before we move um move topics. Like burnout is still an issue in freight. And I'm certain it was probably a uh a common issue at a company like TQL where you know it was expected that you were always on the always on the clock and available. Is there how do you think about burnout? Like if you if again, if you're in this advising role for someone starting a brokerage and and they ask you, like, how do I navigate burnout? How do you how do you answer that?

SPEAKER_00 37:30

I feel so fortunate that I was able to work at TQL and I like really enjoyed being on the phone 24-7 looking back. That's just me. I loved it. Uh, maybe I'm like sick in the head. I've always thought it was hilarious that like you'd be out at dinner and then you're like on your phone trying to haggle something. Like I personally loved it. I think from our business in tech, burnout's very real on the engineering side. Because you know, you're trying to push, you're trying to push, there's always something new. Um, and so you know, freight never stops. Obviously, like selling software probably never stops, but less so. Um, we try to be really cognizant about like giving people time off where they need it, but we don't go out of our way to like and I actually I think this isn't one of the detriments that I like I want to work on personally this upcoming year is like we have unlimited vacation, but what happens is some people just like don't take it. And so I think we have to start giving people like vacation days. We're all going to Costa Rica as a company next week to like unwind for three to four days. All 50 of you. Yeah, because we had a great we had a great year. Um, and so like we're not doing any work. Some of the team was trying to propose like working sessions. I was like, no, we're like, we're gonna go surfing, drink some beers, have a good day. Like, we're not doing that. Like, let's disconnect for a little bit, and then when we get back, let's run after. And so, you know, I think as a leader, you need to be cognizant of that. And as a founder, it's really tough because you know, this is your business, this is your baby, even as a broker, too, this is like what you want to build. Um, but people also have lives and get burnt out very quickly. I don't think there's a, you know, people have been complaining about this for years across verticals and different industries. So I don't think there's a there's a good answer yet.

SPEAKER_01 39:12

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Competing In A Crowded AI Space

SPEAKER_00 40:40

Yeah, I was very fortunate to meet uh a gentleman, Kevin, who I started the last business with. We were working together. I went from TQL to a uh company called Turbonomic, as a bang capital-backed cloud infrastructure provider. Um very complicated. I would not highly recommend that if you're trying to go from freight brokerage to a very complicated technical sale. Um, but we learned a lot of things at the business on like how to build, how to scale a tech company. And then we also saw this resounding problem that no two companies were paying the same price. And so it was kind of like right place, right time. We had a new sales leader coming in, writing was on the wall, we were both gonna get fired. So we're like, hey, let's start this company uh and try to solve this problem. No two companies pay the same price. And at first, we tried to build like a glassdoor.com that would show you software pricing. Uh, and nobody wanted to buy this. And then so we just started cold calling a bunch of people, found uh the Mass Bay Transit Authority, so the subway system, and they were like, hey, you know, we have this problem, we need like a bidding tool. We'll pay you several, you know, six figures for it. We're like, all right, great. So we built it and then called a bunch of other people, and they're like, hey, we could use this too, and the rest is history.

SPEAKER_01 41:55

And you were at that business for six years? How long?

SPEAKER_00 42:00

So started a new company in the beginning of 2024, also got married and had a kid.

SPEAKER_01 42:06

Congrats. Um, six years, the company was doing well, and you had the I guess guts to say, like, I'm out, I want to go build something else. Like, what was the poll? Like, why why stute, why, why, why'd you make that decision?

SPEAKER_00 42:26

Yeah, so there's two sides of the world. One is like I need to save money, which I'm sure a lot of your audience gets. The other side is I want to make money, which I'm sure a lot of your audience gets. I was on the I want to save money. So, like, how do we help get quotes? The other side I've never been on in my career is like, how do I help a business generate more revenue? And for my time at TQL, my time at you know, fair market, and even before that, for like 40 years, accounts receivable has been this really messy space. You have like older software providers out there that have had like billion-dollar outcomes. There's a couple that are public, but like no true category winner. And then every single person I know complains about it. We sold all this stuff, we need to get paid. Uh, and so you know, at Fair Market we had like three people, four people doing it. Um, and I was just like, hey, this is a highly fragmented space where everybody hates the tools, and like I'm sure there's a better way to do it, and so that's why we started Stu.

Engineering Talent That Ships

SPEAKER_01 43:28

Yeah, I mean it was the least interesting part of the business to me. And and I, you know, I I I'm not I don't say that for no reason. I I think I think I'm I think we're all different, yeah. You know, not all entrepreneurs are the same, but sales-minded entrepreneurs, I feel like there's a lot of glory in the sale. Right? There's there's a lot of fun in the sale. You celebrate the sale, but the sale is not worth anything if there's not a payment that comes through, whether it's in 15 days or 30 days or 45 or 60. And that part's just not fun. Like, I mean, that was the least fun part of the business, but it's it's maybe the most important because like the sales numbers don't mean anything if if the the corresponding um receivables don't come in. So um, why like why did you feel like you were even qualified to uh approach this problem? I mean, is is this like you don't have any expertise in it? I mean, I guess you've worked in in sales, certainly, but why were you the guy?

SPEAKER_00 44:38

Um that's a great question. I don't think you're the guy for anything in life or the gal for anything in life until you start down a path and you become very determined. Uh this problem drove me crazy, personally, having done it. You know, my theory, and I I think I saw this firsthand a little bit at CQL was that you have these bigger businesses that act as nodes, and then they have all these like subcomponents of these nodes in a network. And you know, the bigger companies, like let's just take Walmart. It's not like Walmart's not going to pay you. The reason Walmart's probably withholding the payment is because in the transportation space you might have forgot a lumper fee, truck might have been late. So you might have like a$20 million payment from Walmart that's held up because you forgot to subtract$150. That happens in software, that happens in medical devices, it happens in pretty much every industry. That a lot of these technical issues are the reasons that payments are held up from business to business sales. And so, you know, you look at what AI is really good at, it's being able to extrapolate a lot of data, make a statistical guess, and put it right in front of you. It's a great application for accounts receivable. Uh, and so that's why we started the business. And so, what our customers see today is a 40% reduction in overdue invoices in the first six months of using the tool.

SPEAKER_01 45:55

How does that happen? Like what it like walk me through that.

Funding And The A16Z Edge

SPEAKER_00 45:58

Yes, we deploy on top of your ERP system, which sounds crazy, but it's just essentially like your financial system. So it could be QuickBooks, NetSuite, SAP. Usually, if it's digital, it's up and running right away. If it's an older system, so some of our customers, like Honeywell, Perkin Elmer, they might have an older system. We'll just sync files to and from, and we can get that up and running in about three days or less. And then we sit on top of your bank accounts and then your customer success system. So we essentially see everything post-sales. And our goal at Stute is not to just be like an accounts receivable company forever. It's really to handle, help companies handle everything post-sales, to your point. You love the glory, you love selling, but you might have forgotten this invoice, you might have forgotten to subtract this, you have to submit it into this portal of theirs. We can help automate that whole process. So we hook on top of those systems, we see your invoices, we take in all your business rules, and then we start just automating a lot of the manual things. So, to give you a great example, uh, in the Molo days, you sent one of your customers, hey, here's your account statement, your past due. You just moved offices, the customer replies, hey, can you send me a new updated W9? Historically, somebody in your finance team would need to respond with the W9 and then be like, Hey, when do we accept, when do we expect to be paid? You have net 30-day terms. We can automate that whole process today without a human being touching it. And for the Molo side, the person in your finance team doesn't want to have to set out that W9. They don't want to have to remember that. Like you're also probably tasking with FPA, travel entertainment, like a bunch of other things fall under their purview than just like collecting bills.

SPEAKER_01 47:37

I'm curious, is this because there's a number of ways to skin this cat? And some solutions might be your existing AR team at Molo or whatever at TQL still does what they do, but now they have the student technology that is supporting them, and but they're still responsible for all the actions of the technology and they kind of watch over it. Another solution would be kind of like an end-to-end where Stutes owning the AR, and Stut's technology is being supported by a student employee who is handling everything related to the AR function. Like, which of those is more aligned to kind of what the solution is?

SPEAKER_00 48:20

We do the first part, but we also power companies like GenPack, which are big business process outsourcers, that do the third, the second part you mentioned for the latter. Um, what we what we do is like think about it this way 20% ish of your revenue probably makes up 80% of the work. And the difference is like software historically for the last 40 years tried to sell you more seats, more users, more, et cetera. What we're doing is we're actually doing the work. So, you know, we're helping understand the context of the human being at Molo, et cetera, that would do the actual work. We're handling the reach out, the payment matching, disputes. If a customer says, hey, they want to short pay you. We help handle that. And then we give you context between sales, customer success, finance, your executive team, and then even in finance, between like cash application, deductions, disputes, payments, and collections. Um, so you essentially have like an AI digital coworker, and you can ratchet up the automation and then ratchet down the automation.

SPEAKER_01 49:20

So that a that's what I was gonna ask. So there's like an AI agent coworker who is kind of sitting, you know, there's they're slacking or teams messaging between me and you know, I'm the sales guy, and and Joe is the the uh the AR rep, and you know, they're they're messaging between the the us two and and themselves about like, hey, this just came in as uh it's being shorted$150 because of a lumber. They're not paying it because of a lumber. Like, do you approve us removing this lumper? Like the the the exceptions they come in and and kind of inform you, and then you tell them what to do.

Proving Value And Retention

SPEAKER_00 49:56

I'll give you a direct example if that would help. So we have a customer, they're called starter up, they do bus bookings, companies based in Atlanta. Um, so it's let's say it's relatively transportation. They went live in two days, they were sitting on top of Net Suite. Um, really, what's them? They have a team of like five people in accounts receivable. They deploy Stute. We have this structure called tasks. So we take in all their business workflow, and then they can say, Hey, do I want to automate this task? Which would be like a W9 sending back, or your example of the lumper. Hey, this customer's saying it's a$250 lumper versus$150. We've identified the documentation to actually say you're correct. We wrote this email for you automatically with the documentation attached. Do you want to press send? Or that task would be to press send. So, you know, their team would click send, send, send. After a couple times of doing it, they'll get prompts that will say, hey, do you want to automate this in the future? So within like a week, two weeks, the users in finance aren't actually handling things, they're just handling the exceptions. So back to my original point like if your customer's frustrated on a dispute, like say they were really hot and bothered on that lumper fee, and it's like, you know, they're you're gonna lose them as a customer, that should be handled by your customer success account management team. It shouldn't be handled by finance. And so we want to flag those for you automatically and let a human do that versus technology.

SPEAKER_01 51:17

I feel like that's a mistake companies make is letting finance talk to the customer about like real issues versus letting customer success or sales who owns a real relationship, like handle that. And I'm just speaking, and speaking from my own experience of like just I think I think it's not prioritized enough navigating, at least in the brokerage world, some of these finance issues that come up. And just thinking it's a one-off thing that you're like, just let the, you know, let a let AR handle it with the with the customer. Um and and I just I don't know. This is not kind of too the astute solution, it's more just my my anecdotal thought about it.

Hardest Parts And New Problems

SPEAKER_00 52:00

So the pushback a little bit on that and like defend finance and take the counterpoint, you know, they don't have a lot of context in what we're doing or what your team's doing. And so the lack of like you have, you know, take it a step further, like your sales team or customer success team is definitely putting not putting all their notes in their CRM or sales system. Like we we can we can rest assured that that's definitely not happening unless you're reporting all the costs. 100%. Um, and so what happens is you now have a person in finance where like receivables probably isn't the first thing on their laundry list to do that day, or it might be. But now they're supposed to go in and like try to remediate this issue with zero context. It's definitely like a step for failure uh a lot of times. And I agree with you, like customer success should be in the loop or handling most of these issues versus just past to finance. Um, a lot of teams keep like receivables and finance just because it's like a compliance issue. But I think you know, one of the things we try to help customers with is this coordination between sales, customer success, and finance, where you know, we can even act or these emails and calls, we use AI calling as well, can come from the CS team. And it sounds just like a CS person. So, you know, to your point, like there is this world here, it's just an unfortunate situation because they have a lack of context, a lack of data. And then you're just like, hey, can you go get this bill for me? Because you don't really know what like a freight broker is promising a customer on the other end.

SPEAKER_01 53:24

I a hundred percent agree with you. Yeah, I in no way was they trying to say it was like because of an issue with the finance people, it's just a structural issue where like the broker is so focused on their brokering and you know they just send the remnants of the situation to finance and like figure it out versus hey, this is the situation, like we need to do XYZ to get paid fully, and I didn't give you all of that. So, like I think where you run into a problem is where finance goes in with with minimal or no context and is like, hey, you owe us this money, pay us. And they're like, No, you guys screwed it up, and they're like, No, we didn't. And it's like, well, you don't even know because you're not actually you weren't engaged on the front end of the deal and and all of that.

Ideal Customers And Ethics

SPEAKER_00 54:05

So yeah, the bigger problem too is with the these companies that are massive essentially act like countries at this point. You have you know payment gateways, you can't even get a hold of anyone live in real time. Um, one thing we do is one of our customers slash partners, Zoom info, we have like their access to their whole third-party database. So we can find you the right person to like reach out to or have a conversation with. But you know, even for us and like my career, some of our customers, like your person you might be working with isn't the right person responsible at Fortune 100 finance department. And so that person that you're asking has no idea. And they might not even be in the same physical location as the person you work with. So yeah, it's it gets this huge issue, and it's a really good fit for AI. Um, like for example, we have this Fortune 100 medical device company. And if you're to call them today and say, hey, you know, you call their 1-800 number, you call a human being in one of their shared service centers, somebody would have to pick up the call and say, you know, I don't know any questions about invoice one, two, three, four, give me a few to research it, et cetera. Instead, now with AI, we can answer that question instantaneously, pull the information up, take the first pass, and then pass it off to a human being.

SPEAKER_01 55:19

That's such an interesting partnership. Just like not your traditional cus, like ZoomInfo as a customer is is is awesome because like, yeah, you're just getting a great customer in a big company like Zoom Info, but you could go a step further and develop a partnership where you can now leverage their core business to make your business even better. Like, aside from just doing their accounts receivable for them, you you now can arguably have a better product than some of your competitors because of a relationship you have directly with them. Because one of the questions I was gonna ask was like anyone dabbling in AI, whether it's for AR or for any other function in a business, is is becoming part of a very crowded space. Right? Like this is where all venture money is going. Um, you've got a great backer, and we should talk about that a little bit. But like, how do you differentiate in a space that is like quickly becoming very crowded?

Freight’s Next Chapter And Close

SPEAKER_00 56:23

That's a great question. Uh anything with alpha gets quickly eroded, I think famously, just capitalism and feminists. It really differentiates on the product you build, which comes down to the people you hire and the people that join the mission of your company. And so, you know, we are an engineering company that's trying to tackle everything post-sales, especially accounts receivable. Um, and because of that, you know, we try to hire and pay top dollar for the best engineers, and we try to solve these problems thinking about it from first principles with like how AI can help. I think if I'm not mistaken, we're the only tool in accounts receivable that and or one of them in back office finance that uses like AI calling. Um, but audio is like a very underserved experience. You know, it's a customer experience, it's a very underserved experience for a lot of these larger companies or even smaller companies. If you call a company today, you know, you're taking time out of somebody's fine out of finance person to like handle a call, triage an issue, even look up the documentation. It's a great example where AI can just be like, hey, Susie called, wants to talk to you. Here's the invoice pulled up on your screen. That's great. So it really comes down to like the product we build and the team we build to deliver on that product. And I agree with you, it's super competitive, but everything with alpha becomes competitive. So you're either going to win it or you're gonna lose. And uh, you know, our mission is not to lose here. The thing that like I think differentiates us is the time to value. Uh, like our customers within you know, 3.5 days are live, and then you know, they're reducing 40% of their overdue invoices in the first six months. And so when you have a company like Perkin Elmer, big medical device company out of the Boston area, you know, they were able to use that$350 million that they reclaimed to buy two new businesses. And so things like that is like how we differentiate ourselves versus the competitor. Because to your point, there's a ton of AI solutions that look just like the old software solutions that just have venture dollars. And that's not what we're trying to build.

SPEAKER_01 58:23

There's a lot there. That's a great answer. I'm just trying to think of where to go next. So you started with the the piece on talent, and engineering talent seems to be like the most crucial piece, which I haven't spoken about engineering talent, I don't think, on the show before. So I do want to talk about that just for a second. Like, what does the best engineering talent look like? I mean, how do you find how do you like, especially as someone who doesn't have an engineering background, how when you're sitting in the room debating, like, do I hire this person as a founding engineer or as one of my first five, 10 engineers, like how do you know this person's the a 10X versus someone else, or that this person's an A versus a C player? I mean, what what does that look like to you?

SPEAKER_00 59:03

For ownership and agency. It's the same as sales or the same as any other function. It's somebody who's willing to just talk to a customer, build something, or get something out the door very quickly, um, and like not overcomplicate things, that is a very rare skill to find. And somebody who can just own something from start to finish and is like not afraid to talk to a customer, I would say is the definition of like an A plus engineer. And they're very hard to find. But if you when you can find those people, it's like worth the weight in gold. Because usually what happens in software development or as at least some of these companies is you have this function called product management. And if I'm mansplaining, you know, tell me to shut up.

SPEAKER_01 59:45

But essentially they talk to No, it's good for I always I always prefer the easiest, the the most basic layman's explanation because who knows who's listening. So, like the simpler you can make it, the better.

SPEAKER_00 59:54

A lot of companies have like a product function where you'll have people that aren't quite engineers that go out and talk to customers. And they get deliverables, what they want to hear. And a lot of these product people don't have any engineering background. So they might design something, sketch something up, and then they ask engineers to build it. I think especially early on, later when you get bigger, you need some of that function. But early on, you want to have as close to contact to a customer and trying to solve the business problem they're they're looking to solve with the engineers as possible. And so, you know, having someone who can have the conversation with a customer and then start mentally being like, okay, we can automate this workflow by doing X, Y, and Z. We can use AI to do X, Y, and Z. And this is like the first version in a very quick timeframe. That's ultimately what you're looking for. It gets very complicated because I think a lot of people in tech think they're a lot smarter than they are.

SPEAKER_01 1:00:55

So when you started the business, did you guys have funding or how did you go about getting started?

SPEAKER_00 1:01:00

Um, so yeah, we started the business with zero funding. Uh, this is the second company that I've started. So, you know, fortunately have some of a track record, so it makes it a little bit easier, but it's never easy. Um, I was actually gonna bootstrap the company, but had a difficult time recruiting engineers uh without like a brand name investor. So we raised a seed round in the spring of 2024 led by Coastal Ventures, uh Active in Capital, and then some smaller seed funds. Um and then we raised a Series A this well last year's summer from A16Z or Andreasen Horowitz and the rest of our VCs participated in it.

SPEAKER_01 1:01:41

You did that last summer, but it was just announced, right? Yeah.

SPEAKER_00 1:01:44

There's always like a lag. What's the there's like it takes like a month to close around, and then there's usually a lag based on we wanted to change our website, our branding, things like that, and polish things up and then announce it.

SPEAKER_01 1:01:56

Getting a name like that behind you, how has that like changed things for the business? Like what has anything positive come out of that?

SPEAKER_00 1:02:06

Uh yeah, they're a phenomenal investor. It's I mean, one of the things is it's a founder-led fund. Pretty much all of our backers are founder-led funds. So like every single person at the business has agency. Um, whether it's Coastal Ventures, whether it's Activen or A16Z, like everybody that's working at those funds like feels dedicated to help the founders. A16Z specifically, it's almost ran like a business. And so, you know, they have a business to what do you mean it's almost ran like a business? I mean, it's pretty much they have to be. Of course it's run like a business. Okay. It's well, I mean, some of the VC funds. Just explain it. Sorry. I don't like my crap. I just explained it. Sorry. Some VC funds are literally like three people in a room managing like 50, 500 million dollars, and they'll just like make a decision. Versus a fund like A16Z is they'll have like a team of people dedicated to business development. So their whole thing is to go out and reach out to companies and put you in front of companies. They have a whole team of people for talent to just like find out who's on the market, help you recruit roles, help you build things. They have like a whole team dedicated to marketing. Like, what's your brand decisions? We have people for that. We have people for like if you want to start a podcast, if you have if you wanted to, you know, build a marketing demand gen funnel, we have like a team of people to help you with that. So it's uh it's operated more of like an organization than there are VCs out there, and there are a lot of them that are just like people sitting into a room pontificating about what the future is gonna be. Um, for me personally, I find it more helpful to align with like a team versus a person in a room.

SPEAKER_01 1:03:44

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SPEAKER_00 1:05:32

Um not not the best when you just have people in a room trying to be like, hey, you got to hit your sales number. Like, okay, great. Yeah, I'm gonna get right on that.

SPEAKER_01 1:05:42

Yeah, thank you. Appreciate your cash. Leave me alone now. Um, so when did you first feel like this was gonna work? You know, like what was there a moment where you're like, I think this, I think this thing has legs?

SPEAKER_00 1:05:55

It's a great question. I I don't think you ever yeah, I think one of the problems you always have like imposter syndrome where you never think it's gonna work.

SPEAKER_01 1:06:03

Yeah.

SPEAKER_00 1:06:03

Um, we haven't lost a customer to date, which is awesome. We have seen the vast majority of our customers find immediate value. Like, you know, our statistics within the first six months, but I'm talking like the first month, most customers have reduced their DSO by a couple days. Um but uh you know, for us, the job's just getting started and we have a lot more to build. And to your point, it's like a very competitive space. So if we're not every single day wake working up and being like, how do we best service our customers? How do we build better product? How do we rethink what we're doing and make it better for our clients? Then like, yeah, somebody's gonna beat us and catch up to us. So, you know, I think we have legs, I think we're doing pretty well, but you know, there's a lot we can improve on both internally and externally that we're always looking to better.

SPEAKER_01 1:06:51

What's been the hardest part of building the business so far?

SPEAKER_00 1:06:56

I mean, there's always crazy stuff. Uh I think one of the hardest parts has been obviously like recruiting great people is challenging and you always have a lag. So when you need somebody in the seat, you know, whether it's customer success, engineer, you're really waiting like three months, six months before you get somebody. That's always hard. Um I think your problem is always different each week. I mean, these past three weeks, if you ask me what's the hardest part, commercial real estate in Manhattan. It's it's just the most like antiquated, dysfunctional industry of all time with everybody lying to you. Uh, if you ask me in like two weeks from now, it might be something completely different.

SPEAKER_01 1:07:35

That's one of the best parts of building a business, though, of like being in that captain's seat is like every week there's a new problem that's staring you in the face that you don't know how to solve that you gotta figure out. At least that's my perspective.

SPEAKER_00 1:07:47

I like it. I also love seeing other people tackle the problems and solve the problems without you being involved. That's that's what gets me out of bed. And it's kind of cool because you didn't solve the problem. You're like, hell yeah, this is great. What a great day to be alive.

SPEAKER_01 1:08:03

Do you feel like this business is is gonna be specific to certain types of industries, or it's it's it can any business that has AR is is geared up for this to be a successful solution?

SPEAKER_00 1:08:16

Great question. Right now we're started with more uh I'd say like flyover state types of businesses. So think manufacturing, distributors, transportation, freight, businesses that are like margin specific. Um we have a lot of companies that are owned by private equity. And you know, we try to once we get into one PE fund, we usually spread like wildfire and get a lot of referrals. Um you know, I don't think we'll get into the B2C side, so like consumer collections at any point soon. Ethically, I have a pretty big problem around like collections for healthcare. Um and but you know, I think the space alone, if you're looking at it, accounts receivable software is about probably like a five billion dollar, seven billion dollar market. Then if you add the human component in it, you're looking at a$200 billion mark, like$200 billion dam. So there's a lot of opportunity in just the segments we're going after, which are you know businesses that drive the country.

SPEAKER_01 1:09:15

Yeah, I like the way you're thinking about that. And I like that kind of ethical thought you have on the healthcare thing. I agree with that.

SPEAKER_00 1:09:22

Um just when I signed up in life to get AI to start spamming somebody's dying grandmother.

SPEAKER_01 1:09:28

Yeah, no, I'm I'm I'm with you. I'm out on that.

SPEAKER_00 1:09:31

Somebody's doing it. Shout out to them.

SPEAKER_01 1:09:34

Yeah. Screw them. Sorry. Um very interesting stuff, man. I mean it's a cool, it's cool to see your personal growth. Just because I knew you in college, and I won't go into what that was like. Uh, but I feel like you and I are similar people, and um, I don't think either of us does well with a boss. So I think it makes sense that you're in the role you're in, and um it's just you've grown up a lot.

SPEAKER_00 1:10:01

Yeah, happy to happy to see you crushing it as well. I think part of the fun part about life is the nuances that you're never stuck in one role. You can always learn more, you can always better yourself, you can always do something in like who you were yesterdays and who you are tomorrow.

SPEAKER_01 1:10:16

I think that's a great point because I feel like people do feel stuck in the freight industry sometimes. Like you it it's it's it's often been said like once you get in, you'll never get out. And and you you you got out. Not in the I mean, you're still selling to freight brokers today, but um, you're not you know grinding out phone calls to shippers trying to like you know get some loads. You're you're you've like really evolved kind of your your knowledge base and and kind of the work you're doing into just a totally different and and different level.

SPEAKER_00 1:10:49

My nine gets beefed up, so maybe I can get back into it after 11 years. Uh but no, you I think it's a great business. I mean, you had a two trillion dollar business, and like I mean, it is still dysfunctional. You see, and I think the good part for a lot of your listeners and you, if you ever decide to get back into it, is like you got all this tech shenanigans now flushed out, which is great because you had a lot of the people that are like, hey, I kind of know the space, I'm gonna solve this whole space with like a digital marketplace. Like, yeah, that's not working. Uh, and so now you have like the real opportunity for people that want to build something iconic and like solve problems for customers. They have legs to run. And so that's you know, I I I think it's a really exciting time to build. And, you know, America's manufacturing and onshoring, near shoring is just starting to kick off. And so, like, there's not a better time to be in transportation right now.

SPEAKER_01 1:11:46

I agree. I don't know if I got anything else for you. I think I'm happy with where we are.

SPEAKER_00 1:11:52

I appreciate you having me on. Big shout out to the Bears. I hope you guys beat the Packers.

SPEAKER_01 1:11:57

I do too. Uh and I'll because you said that I'll release this episode before that game. That was a good kick in the butt because otherwise it'll be late.

SPEAKER_00 1:12:06

You guys got it though.

SPEAKER_01 1:12:09

I I hope so. And and I have to be honest for my listeners, I'm hoping your Indiana Hoosiers lose to the Oregon ducks this this Friday. I'm sorry. It's not for you. Let's ask your listeners.

SPEAKER_00 1:12:23

I give you a compliment and then you just shot me out of my knees, man.

SPEAKER_01 1:12:28

It's not a you thing. It's it's another IU friend of mine who I just can't stand his IU persona. I like him as a person. I can't stand the IU persona. And Coach Sig, you know, as brilliant of a man as he is, his arrogance is a lot for me. And people probably say that about me, but uh, not the brilliant part, just the arrogant part. Um, brother. Thank you so much for having me on.

SPEAKER_00 1:12:53

Appreciate it as always.

SPEAKER_01 1:12:56

And uh to our listeners, we'll see you next week.