#168: Darren Small (Oko) — Simplifying Logistics and Automating Supply Chains

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If you create a new standard, you can really access new markets

Darren Small: So I think that's really what gets me the most excited. If you create a new standard, you can really access new markets, open up new opportunities, and essentially help these trucking companies. I think specifically, our customers today really improve their margins, because now they can have a, communicated layer where they can communicate more efficiently.

Jeffrey Stern: Let's discover what people are building in the greater Cleveland community. We are telling the stories of northeast Ohio's entrepreneurs, builders, and those supporting them.

Jeffrey Stern speaks with Darren Small, co founder and CEO of Oko

Jeffrey Stern: Welcome to the Lay of the Land podcast, where we are exploring what people are building in Cleveland and throughout northeast Ohio. I am your host, Jeffrey Stern, and today I had the real pleasure of speaking with Darren Small, co founder and CEO of Oko. With over a decade of experience on Wall Street, Darren's analytical background from the world of investment banking, stocks and data, equipped him with a keen eye for efficiency and growth opportunities, which he has now applied to the world of logistics. Darren co founded Oko back in 2021 after witnessing firsthand the transformative power of streamlining logistics operations. And since then, as CEO, Darren has raised $4 million in funding for the business and assembled a team of nimble operators dedicated to revolutionizing trucking operations, delivering greater efficiency, throughout the international and middle mile supply chains with automated solutions to enable businesses to move goods more effectively. This conversation was a lot of fun. Darren is a deep thinker with a ton of insightful perspective. We cover his journey to Cleveland, how to effectively pivot his approach to leadership, and cherishing the journey and moments along the way, the implications of automation in our supply chain, and ultimately, the future of simplified logistics that Darren envisions and Okos role in shaping it.

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Darren Small: Hey, Jeffrey, it's Darren Small. Pleasure, to be here today, and thanks for the time.

It took us almost a year to get this on the calendar

Jeffrey Stern: All right, so let's dive into this. Wow. Long time, long time coming, huh? Huh? Yeah.

Darren Small: Took us a while to get here, but I'm glad we were able to connect. And, I think I was looking back at my emails this morning. It took us almost a year to get this on the calendar, but I'm glad we were able to connect and appreciate the persistence and patience to get this on the calendar.

Jeffrey Stern: Absolutely. My pleasure. And if anything, it's just built the excitement for, your story and getting to hear it and amplify it.

Oko helps logistics companies automate dispatching by turning emails into created shipments

I was thinking about where to start and I thought, a neat place to begin the conversation would just be for those unfamiliar with Oko is to ask you what the business does. From there, we'll unpack a lot, but just as a basic overview for the listening audience, what are you working on at Oko and what is Oko's role in the world at large?

Darren Small: Definitely. Thank you. So excited to be here again. I think really to dive in and just touch on what Oko does. We help logistics companies, specifically over the road transportation companies or trucking companies. We help them automate dispatching by turning emails into created shipments. So within the transportation industry, it, really survives on accurate and timely information. Most of this information comes over via email and, then these emails have PDF attachments with all the order information, where to pick up, where to drop off goods, what you're picking up, what you're dropping off times, weights, dimensions, all the information that you'll need to create a shipment. And when these emails are received, there is teams of data entry clerks that, receive these orders that need to and then need to be entered into what's called a transportation management system, a software tool that then can, help dispatch and properly route the trucks with all the information that needs to be entered on time accurately and with the complete details. So one of the big challenges that we learned in the trucking space is that the sheer volume of emails that their customers receive with not only the orders, but also updates of the shipments, where things are in transit, things that may have gone wrong, drivers asking questions, things just get missed. So a lot of orders can just get overlooked, leading to missed or abandoned shipments, incorrect shipment information which will have impacts when the driver arrives at the docks. They're trying to pick up something, but it's actually something else that they need to pick up. And there's a lot of just miscommunication that can happen. Leads to two hour conversations between dispatchers, operations, the drivers and the shippers, around how to really resolve issues. And that's really just if there's information that's even in the system. And then if people call out, there's also that operational piece. So ultimately, you know what we've created as a tool to really solve that issue by creating an AI assistant that helps trucking companies dispatch trucks faster by taking all the emails that they get from their customers, turning them into essentially data packages that we can upload into the existing software that exists. So, every shipment that comes in turns into a shipment that can be dispatched accurately on time so trucks can go to the right places at the right time.

Jeffrey Stern: I love that.

When we think about the global supply chain, freight forwarding is incredibly complex

I want to do, a little more stage setting here. When we think about the global supply chain, freight forwarding, dispatching all these logistics. I think maybe one of the explicit learnings from world events over the last few years, just given how much it affected our everyday lives, when some part of it broke down, is how important and interconnected and complex all of this has become. And so if you think about these shipping routes, these trucking routes, the whole supply chain, can you take us through what navigating that actually looks like? Ultimately, we're trying to move something from a to b. I just would love to hear a bit more about the number of steps involved from something being purchased to leaving a manufacturer to arriving at a customer's door. The kinds of companies involved in that whole freight forwarding process. What does this all actually look like?

Darren Small: Yeah, it depends on what the manufacturer is making because they can be either a final manufacturer or an intermediate manufacturer. So they're going to need, regardless, they're going to need a ton of inputs that are going to come from other manufacturers. Using an example, the tube of toothpaste, you're going to get the materials that you need, the box that you need, the plastics that you need, the colors that you need, and then as a final manufacturer, you're going to assemble all those things together and then ship those out as an intermediate manufacturer. Let's just say as the one who's creating the flavor of toothpaste for the month, they're going to get all the materials together and then ultimately put that into a large container where they're going to have vendors for different colors, different materials, which can be chemicals, and then sanitation tools and all that's going to be part of their supply chain. They're going to have logistics providers that are going to move from a to b. There's a whole connectivity of orders that are going to be going through. And I think that kind of leads to where we fit in the automation space is that communication layer, because as you're starting to move goods through the supply chain, you need to communicate with your forwarders, as you mentioned, your manufacturers, your vendors, which can be the trucking companies or other forms of transportation. So all of that is that communication layer that we try to mesh together because, as I mentioned in the earlier example where you have, let's just say, shipments that need to be created or orders that need to be entered into the system, there's ultimately that human layer that sits in between, kind of really shepherds that information into the right place. but that can also be one of the main risk factors in supply chain breakdowns, supply chain disruptions, is that human factor. Especially as volume increases over time, that person can act as a form of a bottleneck that prevents shipments from moving from a to b.

HB: So what was your background and foray into this world

Jeffrey Stern: So how did you first encounter this world? Were you a user of parts of the infrastructure of it and frustrated with it? Because again, I think to most people, it's almost a useless term, supply chain, in how amorphous and obfuscated of a concept it is. And we don't really get to think about it on a day to day basis and actually realities of what it looks like. So what was your background and foray into this world? How did you come to be aware of the problem space at all and kind of the founding motivation?

Darren Small: In terms of talking about a startup? We often talk about inflection points, right, trajectories or moments, milestones that change the business in significant ways. And kind of, when I look at my life, I think that it's built on a few inflection points as well. So just would take a moment to just talk about that. Just, talk about my journey in that as well.

Jeffrey Stern: Absolutely.

Darren Small: Originally from New York City, as I said, first generation american. My parents are from Barbados, so I was born and raised. Spent the first 15 years of my life in Queens, New York, then went to join the Queens Falcons at that age, which is a, pop Warner team which was based in middle Village, New, York City. That's, also where I met Sebastian, my co founder, you know, I think that experience having met him. And then we went to boarding school together in Connecticut at a school called Pomford School. that obviously had tons of impacts going forward in the rest of our lives. So then from there I went to Middlebury College in Vermont, where I played football and ran track and field. And that was a great experience for me. Sebastian went out to Bates, and the reason I bring that up is because we beat them every year in football. So I just want to make sure that he knows that he's reminded of that. but it was great memories, both confident Middlebury and very memorable for me moving forward a little bit. Majored in econ while I was at middlebury and spent, a lot of time focused on while I was at school, living in career services. Went there and just spent a ton of time, I think, beginning my sophomore year at school, because I had a big fear of leaving school without getting a job. So I spent a ton of time in career services trying to figure out how to get an internship. Long story short, I got an internship with an investment bank. That led to spending ten years on Wall street, and then where I spent all that after leaving undergrad at Middlebury, that I landed at MUFG, where created the operational risk management department for MUFG in the Americas with, Elaine Hutchinson, who I would say is another kind of major influence in my life. She was a great mentor and friend, and she encouraged me to go to business school and ended up going to Simon Business School as a fielding fellow in the fall of 2019, which was, again, another great experience for me, being a part of a small cohort of students at Simon. That's, as I mentioned, where I started my first startup, first taste of AI. Then as part of that, that first fall when I started Simon launched, really was full swing at Twilight, our first startup. And then I actually withdrew from school that first fall to go back to move to Boston to work with my co founder at the time on Twilight. So again, this is being in the fall of 2019, which rolls into the spring of 2020, when the pandemic rolls around, and then we both ultimately decide to step away from the business at that time. And then I decided to go back to business school, work full time, go back to MUFG, also just kind of being the crazy person that I was, decided to go back to business school, which was also a really cool experience, I think being at muhe at that time, because they were going through a transition where they were selling Union bank, their retail arm. And then, yeah, really, as I wrapped that up, that's what led me to getting the job offer from Amazon, graduating from business school, the, fall of 21, there were really three places that Amazon had available at the time, which was Ruskin, Florida, kind of right outside of Tampa, somewhere in Idaho that I don't remember, and then Akron. So my wife, who I met through Sebastian. So again, another pivotal person in my life. My wife had a friend who went to school at Hathaway, Brown, here in Cleveland. So I guess the cool kids call it HB. So she went to school at HB and then my wife gently and kindly told me that we're not going to anywhere else but Cleveland. So that's when we packed up the car, moved out to Cleveland. Yeah. So we've been here for a little over two years now. And after moving to Cleveland, decided that I didn't want to work at Amazon. Committed full time to working on Oko with Sebastian. Yeah, we were accepted to our accelerator in early 22 and kind of from there the rest has been history. So Sebastian, he had worked in import export of logistics or really chemicals. so the import and export of chemicals from different countries either into the United States or he would just funnel it into other countries for manufacturing process. So for him he had really learned a lot about how documentation was really the truth of where shipments are in their lifecycle, and really just the availability of goods and how impactful that was to not only internal operations but to your vendors, which would be these logistics companies. Through his experiences of feeling the pain points of, I would say poor communication just due to all the volume of documentation that was going in and out of his organization. He really had impacts that were material to his business, because if things were out late or they were missing or the documentation was missing, there were fines and fees that would impact his business. So we started having a conversation in early 21, kind of after the pandemic where supply chain was top of mind for most people. We started really diving into that and just seeing if there was an opportunity for helping streamline communication around documentation. So we started working in chemical manufacturing, understanding kind of the pain points around what he was experiencing from his actual buyers. And then that led us into freight forwarding, where we were working with the forwarders who would be managing this documentation on behalf of their customers and then would be interacting with us customs, for example, to clear these goods through port and the communication of documentation through that and how that's another part of the lifecycle. And that data really carries along really the information, but also the clarity that everyone's looking for as part of that supply chain process. And I think that's ultimately what it comes down to. And then when we started working with freight forwarders, their vendors or trucking companies, and then one of the things that we learned is that from trucking, ah, company, their processes are very repeatable. So you get the document in, you have to dispatch the truck to provide services to your customers. So once we realize that and the power of, really the importance of dispatching these trucks on time to the right places so that you can fulfill your customers needs, the value that ends to that adds to their customers. Right. So the shippers who need these goods move from one place to another. The importance of that, the reliability of service, the customer excellence is really a key part of what makes trucking companies different from one another. Obviously delivering those goods and services on time. but you can only be as good as the information that you have. And I think that's one of the things that we've learned through the process of working, with trucking companies is that once we can get the timely and accurate information, they can respond more quickly to their customers and provide higher level of customer service. They can grow their businesses through having more automated processes and systems. And that's really how we landed in the trucking space. Going from combining my experience in financial services and building AI products to Sebastian and his background in logistics, really just working with our customers and our partners to learn more about the industry and providing these services and tools to help companies do more with less.

You went from manufacturing to logistics over this middle mile

Jeffrey Stern: Trey and I imagine as you ultimately landed on trucking, as you traversed the set of organizations that you were working with prior, I mean, I imagine you must have uncovered a lot of problems, along the way. What, what was it about trucking in particular that felt most compelling? That, you know, this is the direction that we're going to take this amongst the whole set of real challenges that kind of plague the overall system.

Darren Small: You know, looking back, as I mentioned, we went from manufacturing to logistics over this middle mile. Logistics is kind of what is called over the ocean. And then trucking's a big industry, but I'm just going to call it the final mile industry. Yeah. So when we start with the first mile in the, in the manufacturing space, they have tools which ERP, the enterprise resource planning tools, which is their single pane of glass to the organization. When you talk to manufacturers, they have tons of different processes, even within the same industry about how they do things. so there's a lot of customized tools that exist in the market. I think the big ones, like SAP and Oracle have tons of modules within them. So to really sit and play in that space, you have to meet the customer where they're at. So that's the expectation of that industry, is to have tools that will meet business needs where the businesses are. So I think that's really one of the things that we learned is that in order to grow in that industry, we're going to have to be very flexible and very customizable for our customer and customer base. And that was in a direction that we wanted to go in. Particularly, I think some things can be true for the middle mile segment as well. So, that over the ocean freight forwarding, even to some degree, I would say the air freight industry is the same way, maybe less so than the ocean industry, but I think there's still a lot of customization there. Even the way that organizations run their processes is very different. But when you get to that final mile space, that trucking space, it's a very repeatable process where it's consistent, it's supposed to run in a particular way. And then that allowed us to deploy or really work with our customers to share one product that would serve their needs in the same way. And we didn't have to do much customization to our product. We met this, met our customers exactly where we, where they were every single time. And that, I think, for me was really exciting because it just opened my eyes to the opportunities that were there in the trucking space. I think just really starting with something simple such as dispatching, we've now expanded into other opportunities of confirming what was actually on the trucks when the trucks leave warehouses, to helping with some payables information that comes in via email. So I think just really starting with the dispatching, which was a repeatable process for each trucking company, we got to get the trucks on the road to pick up the goods. And then I think really just learning from our customers that there are other opportunities that were, again, similar to each trucking company was one of the big things. And I think we remove a lot of the international aspects of it. Again, going back to that middle mile segment, which is going to be dealing with customs in different countries, different, ah, ways of just communicating, I think, generally. But in the US, over the road trucking is fairly uniform. So I think that's what makes the opportunity pretty interesting.

Oko focuses on helping trucking companies automate the data entry process

Jeffrey Stern: So you mentioned, the simplicity of the problem at the onset, and kind of a refinement of the focus towards something that you could build that is generally extensible and required less customization. But at the same time, from the outside, it feels like a really big, complex, fragmented space all the same. So how do you attack the first build, first product, the first customer? What is the process of actually getting started look like in Oko's journey?

Darren Small: Yeah, I think the problem, at first glance sounds simple, because, once we can get the shipment into the system, we can go pick up our goods. But like I mentioned, there's all those complexity about the details that need to be accurate in the shipment, along with the information, and then taking the steps to even provide more value to the shipment as it goes through its journey, which is what we're doing for our customers today. For example, the documents that are sent over via email, those are typically attached to the shipment digitally. So that, let's just say when a driver arrives at the dock, he could read the information, have it signed off as his proof of delivery, and then that can go on to support the accounts payable team, resolve any discrepancies that the driver may have at the dock when he gets there with the shipper, make sure he has the right equipment for when he needs to make his, actual pickup or delivery. So all of those different knock on effects that I would say would be part of that initial data entry are some of the workflows that we support downstream with our customers today. But when we first got it started with our customers, we started working with just the data entry, getting the information into the system to prove that we could do exactly what we said we're going to do. And then once we built that confidence with our customers, then they started to ask for the next thing within our workflow, which we're uploading the document, sending confirmation, emails that it's been entered. So typically, you know, acknowledged or entered is something that our customers would send back to, their customers just to let them know that they've received the information and they will be making this the pickup or drop off. So now that's something that we do for our customers. So the roadmap continues to be built out by our collaboration with our customers. I think that's really the most exciting part about it, is that they help us, you know, build what they need to streamline their workflows, make their lives better so that they can, again, work better with their customers, understand how to provide better service, grow their businesses. So that's really how we've, you know, we got started with, just starting with the simplest thing, which was solving the problem they face every day as they get emails that come over, entering it and to enter it into their TMS system, so that they can, they can take their next steps from there.

Jeffrey Stern: And did you find in addressing this specific problem that more of the challenge is combating the way that they have done things historically, or is more of the challenge coming from competition that has also, identified this problem that's working to address it in a similar way.

Darren Small: Yeah, I think the first thing, I think we have a really unique way about how we solve the problem in terms of getting the data entry, and we don't have a front end as a product, so there's nothing that our customers actually see. we work directly through email, we capture all the PDF documents and automate the data entry into systems. So that helps teams be more focused on the existing process that they have in place today. There's not another technology that they need to learn how to use. No drag and drop. everything just happens in the back end. So I think the way that we have thought about attacking the problem is pretty unique. one of the things that we have learned, I think, as we've gone through this process is that people are very skeptical of technology, and AI in particular. So I think that's been one of the big challenges that we've had to overcome. But I think once we get over that hurdle, typically through a few trials, once we have about a week or two with a customer, for them to see the automated experience and to just understand what the workflow would look like, we can usually overcome that hurdle and get customers to really enjoy using our product and expand it to, really the rest of their organization and all their sub customers or customers that they don't have automated connections with.

You've brought on some outside capital to help you realize your vision

Jeffrey Stern: So along the way, you've brought on some outside capital to help you in, the realization of the vision that you have. Tell us a little bit about that whole journey, what that longer term vision looks like that you've painted from the perspective of investors and ultimately the impact that you'd like to have.

Darren Small: Before moving to Cleveland, I was offered a job with Amazon to, manage a fulfillment center in Akron. So very shortly after moving to Cleveland, I actually turned down that job and decided to work on oko full time with my co founder Sebastian. And after deciding to do that, we applied to an accelerator in New York City called Era. So, we were accepted into that. While we were part of era, we were just our first round of capital with Brooklyn Brid Ventures, one of the founders of ACV auctions. And obviously era that was early 20, two. And then after moving to Cleveland and raising our next round of capital, later that year with Harlem Capital Jumpstart, great partner who was a part of that round, we were able to secure some more capital to really help us continue to grow within the industry. And, I'm really excited to have our capital partners on board because they have been really instrumental in terms of making connections and helping us get the resources we need to grow. Our team is still pretty small, but lean and mighty, I think is really the best way I would describe. And one of the ways that we're looking to continue to grow into the industry is taking the information that we get and the connectivity we get between our customers and looking to help them grow their businesses through that. so there's a few avenues that we're looking to run some tests, I think, over the next year or two to really understand what the next avenue could be for our customers. But some of the things that I get excited about are creating marketplaces between carriers and brokers. That's something that we've heard from a few customers that, that could be interesting. Looking to see if we could help the data that we get from our customers be more valuable about how to optimize their business. Which lanes, which routes are the most important. But I think ultimately the route where I see us going and the thing that gets me the most excited is creating a new layer of information, a new way to communicate within supply chain management. So right now, as I mentioned, we automate all the non automated connections. So really any data that comes over via email. But, some customers do. There's an industry standard called EDI and that's electronic data interchange. And that's an old school version of API, which exists in a few other industries such as healthcare. What we found out is that customers actually find more value in our products because we can get the, information into the system faster than an EDI, an automated connection can. So they're actually looking for our product to replace some of the existing EDI connections that they have today, which really creates a big opportunity for us to really create a new standard in the industry for how things are communicated across supply chain partners. I think those are some of the things that I really start to think about is how can we create a new standard that makes it easier for folks to communicate information across supply chain, reduces friction in the supply chain as people are looking to communicate. And I think that has tons of opportunities, not only domestically, but when we talk a little bit about the freight forwarding industry, there are so many layers of communication and overlap within supply chain that if you create a new standard, you can really access new markets, open up new opportunities and essentially help these trucking companies. I think specifically our customers today really improve their margins because now they can have a communicated layer where they can communicate more efficiently and then that allows us, not only as a company, but I think as a broader society, to have the opportunity to create new industries that were in existence before. I think there's been a big focus on a lot of other aspects, our society, that need to be kind of addressed. I think climate change is something that people are taking more of an investment into. Electronic vehicles, I think even flight is becoming something that people are starting to look at a little bit more through space technology and other forms of technology, and then we can help just reduce a lot of those costs as we just drive efficiency through the supply chain management process, which can help bring these new industries to market. So I think starting with something very, very simple, which is making communication more efficient, the same way that email does, as opposed to sending letters to each other, creating a new layer of communication where we have people drive communication more efficiently, just makes the world a better place. So generally, I believe the same thing, and I think that's what gets me really excited, is how can we transform communication so that we can then transform the world? Because I think that's really where I see the opportunity.

Jeffrey Stern: In Oko, what is the path to get there? If you work back from that imagined future, what are the things coming up that you're most excited about, most nervous about? Or maybe another way of phrasing it is, if Oko is not where you would like it to be in 1015 years, what are the things that have stumped you along the way?

Darren Small: The path to getting there and where I see how we can get there is, even with our small cohort of customers that we have today, we can see that there's already overlap, that they do business with each other, they have connectivity with each other. So I think there's very, easy ways for us to build the route to having that connection and that communication be more automated, even with the people that you already have around you in your ecosystem. Some of the challenges, I think, as I mentioned before, I think it's just that hesitancy to technology is one of the big things. So there would need to be a shift in terms of how logistics companies and their overall network looks at technology as an enabling system that will allow them to do more with their business. And I think that's the big thing that we have to really do. I think, as an industry, specifically in logistics, is to just understand how technology can benefit everyone that's involved in it. But I think that's going to be coming through the proof in the pudding. I think that's what everyone's going to be looking for is to see that, we can start with our value proposition of getting the data into place at the right time, faster and more accurately than anyone can do it. And then I think just getting more buy in from some of the larger players in the industry who we already support their customers through data entry, and then bringing them together with our ecosystems is really how we get there. So I think it's just building a community of people who believe that they're just kind of what I laid out before, that the world could be better. Just that, if we communicate more efficiently. And I think as long as we continue to build our ecosystem and our community, I think we'll definitely be able to achieve, everything that we set out. And even more because, as I said earlier, our customers have been teaching us, and the ones that we work with in the industry have been teaching us what are some of the big problems and pain points and how we can solve them, and then we just collaborate and create that roadmap together. And I think that, yeah, the more that we collaborate with others, the better off we'll all be.

Oklahoma is exploring ways to help trucking companies automate repetitive tasks

Jeffrey Stern: And at the same time, though, I'm sure you can sympathize with the fear, the aversion to full technological adoption, because in trucking specifically, I imagine they're getting this automation and AI narrative, not just from maybe the tooling and infrastructure side, but from autonomous driving and really just across the board things that will be automated in this pursuit of doing more with less. What strategies have you explored to work through that? I think very real apprehension about some of the implications of what it actually means to be more efficient and doing more with less.

Darren Small: Yeah. Today our goal is not to replace your entire staff. you know, I think that's one of the real and present fears that people have. We're really here to help your team do more, help them to be more efficient. I think one of the things that we have heard for folks that are in the data entry team, they have to come in, overnight shifts, they have to work on holidays. There's things that get in the way of us enjoying, I would say, a normal, relatively healthy lifestyle. So we want to just be that tool that can help support your team through that, through just kind of a normal operations and make sure that they're driving efficiency through their processes. And, you know, as you can see, that efficiency, then you can grow and focus your team to do more in different areas. and then particularly when I look at, you know, folks in data entry, that's not necessarily a career that has a lot of mobility in terms of growth and, and what you can do next. So, I think that's one of the areas where I do feel like the benefits that Oklahoma provides help people to transition into other roles, such as customer support, because they've done the data entry and now they can move into a customer support role. We've seen some of our, customers do that with some of their data entry folks. So now that people do have an opportunity and a path to move forward in their career, because they've built the relationships with the customers, they understand the business, and now they can move into something, more fulfilling and more interactive with the rest of the industry. And then that really creates the path forward, for growth, for people who are coming into the industry. So, traditionally, when we looked at data entry, that was a very stagnant role, but now we're starting to see in very early cases that they're recreating now path to mobility, because they're learning alongside, let's just say, an automated assistant that's going to help them understand what needs to be, where and why. And that gets me very excited. And then talking to the broader market itself and looking at other things that are happening in the industry, I think there are kind of paths towards AI, really. I think supporting people rather than replacing people on the autonomous trucking piece. I'm interested to see how that plays out. but I think we will ultimately still need some form of human interaction to get things, especially in the medium and short term. And the long term, I'm interested to see how that plays out, but I think over the next ten to 20 years, we're still going to need some human interaction to get things, to the places where they need to be until the product can really be refined to a place where it's truly hands off. And I think that again, that also creates pathways for folks to move into different, roles. I'm not sure what that would look like, sitting in the cab of a truck, but I think that that still, leaves opportunity for folks to have mobility, in different areas.

Jeffrey Stern: Yeah, no, I mean, it all resonates. I certainly share the belief that some highly repetitive tasks should be automated because it unlocks our time to focus on more creative, fulfilling kinds of work. And often those kinds of roles are not, while simultaneously they don't offer, I think, the career path necessarily, they also aren't attracting a lot of people into them in the first place. So, there's not like a new generation of data entry people. If I draw the analogy to some of the work that we've done in the healthcare space, ah, around, I think, a similarly repetitive and, automatable task around validating data entry information for credentialing purposes.

Darren Small: Exactly, yeah. And I think that's one of the big things of you mentioned attracting new entrants into the workforce, new people into the industry. That's one of the main challenges that we hear, as we go to conferences and talk to our customers. Getting great talent to come into the industry is extremely hard because there's a lot of other options today. And when you look at a 20, some odd kid, that wants to come out of school, logistics may not be something that they've even heard about, which makes it kind of an unattractive industry. They feel a lot of the things that we talk about, that there's no mobility because no one can really take them through what the trajectory or career path would look like. And I think the more that you even put technology into those industries and highlight them, people can start to get more visibility as to why logistics, shipping would, be an industry that you would want to pursue. So I think it is important to have technology in those spaces, not only from an operational efficiency perspective, but I think from an industry growth perspective as well.

Oko is your second time around in the entrepreneurial journey

Jeffrey Stern: Speaking of career opportunities, you had mentioned that Oko is your second time around in the entrepreneurial journey. And I'm curious, as you've made serious progress in Oko's journey and in reflecting on both experiences, what, if anything, you're doing differently the second time around, than the first time. And some of just, the reflections on getting back into trying to build something from scratch relative to a more set in stone career path.

Darren Small: I think coming around second time, I think there's a saying you have to be flexible but rigid. I think that definitely resonates, going through the journey and having made a few pivots along the way to get to where we are today. But I think one of the big things that really resonates with me is not hesitating on making decisions. I think there's a yoda has a saying, do or do not do, there is no try. I think that really resonates with me as I look at the journey through Oko and then through my previous startup experience. Wasting time is just the enemy of fulfillment. So, for example, I think having worked with, building a startup, you have employees that you need to hire and people that need to perform and sit in specific roles and unfortunately, from sometimes it just may not work out for different reasons. and I think that when you spend a lot of time debating the issues or really not even taking the steps to address it, which can be identifying the issue, working with employee, figuring out a path forward. And again, the theme of communication is sometimes it can just be a, misalignment of communication. The expectations can just be in different places. And I think if you don't take the steps to address items, especially on the employee side, I think that can be very, very difficult for a company, especially an early stage company, to grow and grow efficiently. So you want to get everyone rolling in the same direction as quickly as possible. And if for whatever reason, you can't all just be aligned, I think you just have to for respect of each other's time, I think more than anything to just take, the time to step away and just reevaluate, the options there. But I think really not hesitating to make decisions and being intentional about the decisions you make, I think is really important. for anyone, I think for early stage founder, I think it's definitely critical, but I think for anyone in their personal lives, I think I'd start to adopt some of those same rules in my life as well. Let's attack it, and let's attack it with intensity.

What motivates you? Learning, solving problems is what motivates me

Jeffrey Stern: What motivates you?

Darren Small: Yeah, learning, I think learning something new really motivates me. challenges, I think, are part of that learning process is presenting myself with new challenges and seeing what are the tools that can be used to solve them. I think, an early stage company is kind of the best way to continually challenge yourself because you're constantly faced with problems. and then also for me, going into an industry that, is brand new to me, there's a lot of learning that I get from my customers. A lot of that I get with our partners. So two of our great partners is crown data system and, Turbo. Crown sits in the air cartage space, and turbo works with brokers and three pls to help them manage their processes through a ticketing system. So I think there's a lot of different things that I can learn from, you know, different folks within the industry, and then all that's used to unlock different milestones and next steps. Understanding how to solve customers problems through technology, I think is also really interesting for me, how to work with our vendors to get them to be more sticky for their customers, provide better service for their customers, and then again, creating that ecosystem and that community where we're all helping each other to win, I think, is what really excites me. But solving those immediate challenges that our customers face is what really motivates me.

Building a great team is extremely difficult in the startup industry

Jeffrey Stern: What have been the hardest earned lessons along the way?

Darren Small: Yeah, I think it talked a little bit about that decision making piece and the employee piece. I think that's, that for me really resonates. I think, building a great team is extremely difficult. And then, that's what's in the startup industry defined as a non technical founder, trying to build a technical team, without necessarily having the resources and finding great people that you can lean on for advice, mentorship and, to really fill the gaps that you don't have in your skillset. I think that's been one of the biggest challenges, but it's also been one of the greatest opportunities because you get to meet a lot of great people along the way and you get to learn a lot, again, just get to learn a lot from people, who are more experienced in areas that I'm not. so I think for me that's really, really one of the things that I've learned. And the hardest lesson, I guess the hardest learned lesson there is that you can't do everything, and it takes a community and it takes a group of people around you who are all excited and motivated by the same things to win.

Moving from New York City to Cleveland has been great for oka

Jeffrey Stern: How has it been building in Cleveland?

Darren Small: It's been great. I mean, I think moving from New York City to Cleveland for me has been one of the best things that I would say. I think it's been really great for me to be here and to be in a space where I can be totally focused and invested on building oka, but also be surrounded with a community that has the same passion and intensity for startups that I would say could rival almost any city. And I think that's how we got connected as startup founders. And I think that building an ecosystem and community where people are focused on doing the same things has been extremely helpful because you can have the resources to just have those conversations. I think those casual conversations about what you're facing as a founder, walking through the journey, understanding how to get a different perspective on things and to look at things differently, has been really important and great for me. having one of my investors locally, Jumpstart, I think, has also been great. They've been a great resource in getting us plugged into folks that we can have conversations with, in the supply chain industry and then also in the venture capital space as well. I think that's been really important to have a partner who can sit on both sides of the fence and then provide value in that space as well. So I think that's also been really important. I think being in a new city also provides just something new for me. I think logistics, is a great hub here in Cleveland. We're connecting with a few companies that are local here. So I think that's also been a great opportunity for us to grow, as a company as well.

Jeffrey Stern: Yeah, that's awesome.

What have we not talked about that you care a lot about in the world

What have we not talked about that you care a lot about in the world? Or if learning is the motivator, what do you spend a lot of your time trying to learn about right now?

Darren Small: The two things that I'm focused on learning right now is, machine learning how to design amazing machine learning products, because I think that that term right now is kind of overused in the industry. and, not m sure it's providing the value that customers are expecting from it. So I think how do we build amazing products for our customers given, the workflow that we're in? I think that's one. But I think the second thing that I do spend a lot of time on is how to be a great leader at an organization. I think as we grow and we hit different milestones, what are the different tools, what are the different ways that I need to interact with my team, becoming more self aware. So I think there's a lot of personal growth that I spend a lot of time on right now, trying to understand ways to get the most out of my team, and so that we can just deliver great things to our customers. So I think that's, I spent a lot of time, working on just being a better leader for my company, my organization.

Can AI help people perform tasks without disrupting existing workflows

Jeffrey Stern: What are some of the threads that you're pulling on from the AI product perspective, what do you feel is the role of machine learning AI in application? What are the implications of this from your perspective?

Darren Small: I think the way I see AI right now is that, as a broad term, I would call it an assistant. I think the great, the key, the hallmark example right now is chat GTP OpenAI. You can go in there and it will assist you in finding a recipe, drafting a cover letter. It will help you start these processes, not necessarily finish it. So I think AI today is an assistant that can help you perform tasks. Where I see the next iteration or where AI is going to really provide its most value is really providing automation, taking that assistance to the next level, providing automation of tasks. Can you do things for me that I no longer want to do. I think looking at what we talk about today is that automated data entry, but then the workflow extends beyond that. We talked about autonomous driving. That's part of a workflow. It's just things are where is AI going to have its next kind of evolution in society, I think is what's going to really differentiate companies, who are going to exist today versus companies who are going to exist tomorrow. Can you take that next step to really help people perform tasks, be ten x better than they are today without really disrupting their, workflows? And I think that's a big thing that I've learned throughout working with technologies, you cannot disrupt existing workflows. You have to be enabling to the workflows that exist today, helping people do more, helping people be better, helping people be more creative. And I think those are a lot of the threads that we're starting to see in AI as we look across mid journey and some of the generative AI tools that are helping people create content. it's just like now, how can we take that content and then do more with it? I think starting to think about how we can embed it more into daily life is really going to be the next iteration of AI. If we can't take it there, I think it'll start to lose some of its appeal. Similar to blockchain, I think there was a lot of conversation around that, but it never really was able to embed itself into daily life. And I feel like AI, has that same existential threat where it's going to be a conversation for a while and there may be some players, but ultimately it will just be kind of a side conversation for some folks as opposed to really adhering in places in.

How do you work on improving leadership? How do you solicit feedback

Jeffrey Stern: Life and being more enabling on the leadership front. How do you work on that? how do you solicit feedback? Do you have mentors that you work with, aspire to? How do you kind of actively work to improve leadership?

Darren Small: Yeah, I have a coach. I should read more, but I listen to a lot of podcasts. I don't read as much, but I listen to a lot of podcasts. And then, I think my wife is definitely a great resource to get some feedback on some things. So I think you definitely need to have a community or someone that you can trust that you can just have some conversation with, honest conversations with, and then, experimentation, taking all the feedback that you get from people. So with my coach, I will focus on some actionable development skills that I could use, different tactics and approach to solving, whether they're just day to day problems or really challenging and difficult conversations. How do we approach that? Taking some of the feedback that I get from, or some of the things that I hear in podcasts and trying to translate that into. What does this actually mean in a day to day scenario, then using that as kind of a feedback loop, and then obviously looking at my wife and some of that conversation as well, and taking all that information and then coming up with an action plan. I know a lot of times this may seem like a little bit, hokey or kind of scripted, but I think when you can really think, if you can think about how to approach a problem, then layer your authentic self on top of it, it can come across as who you genuinely are. I think that when you can take a process having this, I would say group or community, a resource, pool that you can lean on and then start to test things, you can then get feedback from people. You need to be very open and honest with your team, open, honest with yourself as well. I think sometimes, you know, when you ask for feedback and people give it to you, you have to listen to it, and take that. So I think it's a two way street. When you're lurking on leadership, it's not just us, it's just you trying to be more whatever you envision a leader to be. It's also a lot more of listening to what people envision leadership to be and then having a conversation about, you know, where we're going. I think ultimately, leadership has to be, we are leading in a direction, so if we're leading in a direction, how do we collaborate together and make sure that we are achieving an outcome? I think that's ultimately what leadership is really going to be focused on, rather than people always say, it's not personal, it's business, but I think understanding that there is a personal aspect to it, but then making sure that it's always aligned to the outcome, and we are trying to achieve this together, and we're enrolling each other so that we can be successful in achieving that outcome. So I think it's kind of weaving all of those things together, because nothing is, static. Everything's fluid. People change, situations change, and we all have to adapt to that. So I think having a group and community of people that you can lean on, resources that you can lean on, and then a great team that you can just get feedback from and work on different things with, allows you to kind of just grow as a leader. So I think those using that is kind of my, my analogy, I guess that's, that's how I work on it.

What are the hidden gems about Cleveland that other people should know about

Jeffrey Stern: As we work to bookend the conversation here. You know, in your, in your two years of time here, what are the hidden gems? You know, what have you discovered about Cleveland that other people should know about that maybe they don't?

Darren Small: Yeah. You know, I think living downtown for the first two years, east force was great. Spent a ton of time there. I think they have great restaurants up and down east, forests. I think the small business scene here is pretty cool, too. There's a lot of, you know, going to restaurants and stores that aren't all big boxes is refreshing. but I think my favorite part of Cleveland are the metro parks. I m think that is an underrated gem. Maybe it just feels underrated to me because I feel like no one talks about it. But I love the metro parks. you know, they have, like, over 20,000 acres of trails, nature space, waterfront, views. and I appreciate that, obviously, coming from the city, New York City, I did spend a lot of time wilderness camping growing up, so I do appreciate, I do have a kind of a soft spot for nature. and then kind of comparing it to the New York City park system. It's just like, it's small compared to what Cleveland has here. So Cleveland has like, a very extensive network. New York City is half the size. But, you know, I really appreciate just getting the opportunity, when the weather's nice, to go outside and really spend some time hitting the trails and just, you know, reconnecting, and spending some time outdoors. So I think the metro parks, for me, that's the win.

Jeffrey Stern: Yeah, that certainly resonates. They are, they are pretty incredible. Well, Darren, I just want to thank you, you know, for, for coming on, sharing your story. I know, again, a long time coming here, so I'm glad we got to make it happen. So thank you.

Darren Small: Thank you. Appreciate it.

Jeffrey Stern: Jeffrey, if folks had anything they wanted to follow up with you about what would be the, the best way for them to do so.

Darren Small: Yeah, you know, I think on LinkedIn, that's definitely the best place to connect with me. You can feel free to shoot me a LinkedIn connection. I'm definitely fairly active in looking at that. So, Darren a small is, my online name, so you can find me there on LinkedIn. I think that's definitely the best place to connect with me. So appreciate it, and thanks for the time, and really, thanks for everyone for listening in. Perfect.

Jeffrey Stern: That's all for this week.