Neil Patel

I hope you enjoy reading this blog post.

If you want help with your fundraising or acquisition, just book a call click here.

Shoaib Makani is the co-founder and CEO of KeepTruckin which is helping trucking companies manage their fleets and have their drivers legally log their hours. The company has raised over $200 million at a $1.4 billion valuation from investors like Index Ventures, Google Ventures, IVP, Scale Venture Partners, Greenoaks Capital, and ITOCHU Corporation. Before becoming a trucker, Shoaib Makani was a VC at Khosla Ventures and also an employee at Google.

In this episode you will learn:

  • How to survive three and a half years with no revenue
  • Why most startups fail, and how not to
  • The hardest thing you will have to do as a founder
  • Ways to resolve tough problems


For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

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The Ultimate Guide To Pitch Decks

Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400 million (see it here).

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

About Shoaib Makani:

Shoaib Makani is the founder and CEO of KeepTruckin, a mobile and web based fleet management provider. 


Before becoming a trucker, Shoaib Makani was a VC a Khosla Ventures, where he led investments in Indiegogo, Instacart, Simpler, and a number of other consumer and enterprise technology companies.


Prior to joining Khosla Ventures, Shoaib Makani was an early team member at AdMob, helping the company expand into Asia and Latin America.


Shoaib Makani is an active angel investor and advisor to startups. He can be reached at [email protected].


Connect with Shoaib Makani:


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Alejandro: Alrighty. Hello everyone and welcome to the DealMakers show. Today we’re going to be learning from the operator’s side, the investor’s side, and you name it. The guest that we have has been on every side of the table that you can think of, and I think that his experience building companies that scale is super impressive. So without further ado, I’d like to welcome our guest today. Shoaib Makani, welcome to the show.

Shoaib Makani: Thank you for having me. It’s great to be here, Alejandro.

Alejandro: So originally, you grew up in Texas. How was life there?

Shoaib Makani: Yeah. I was brought up in Texas, in Central Texas. A thoroughly rural place initially. A town called Little River-Academy. Then later, my parents moved just outside Austin to a place called Cedar Park. It was a great way to grow up. Yeah.

Alejandro: Great. Then after this, you started to develop your love for math. How did that happen?

Shoaib Makani: Yeah. For the last two years of high school, I went to the Texas Academy of Mathematics and Science. It was a two-year residential boarding school. Imagine taking the 200 nerdiest kids in all of Texas and bring them together for junior and senior year of high school. It was a great experience. I think I got to develop my interest in math and science, and also, it really deepened my appreciation for what it took to build products and companies.

Alejandro: Then from that, you landed in NYU, which resulted in transferring into LSE. What did this open up because you were used to being in Texas and Austin and then all of the sudden you find yourself in a place like New York City or London.

Shoaib Makani: Yeah. Going from thoroughly rural Texas to the middle of New York City at the age of 18 is a pretty incredible experience. I love New York, but what I realized was, I didn’t need to study finance to build a company, and in fact, one of the more holistic understandings in the world. So I ended up transferring to the London School of Economics where I studied political economy, government economics. It was a really interesting time to be in Europe. This was early, mid-2000s and Europe was adopting the euro, and there was intense debate about the impact of common monetary policy and a monetary union on a lot of very different economies. It was a great way to get an appreciation for the various economic and political models that worked in different parts of the world.

Alejandro: So thinking about political models. What did you learn about this because this is completely different from math and from finance? Obviously, it impacts, the decisions, finance, and all of that, but what did you learn about that?

Shoaib Makani: Yeah. Really gaining an appreciation for the varieties of capitalism, seeing how liberal market economies work, how coordinated marketing economies work, and why, and the institutions, and the culture that was necessary to drive success in those varied economic models. While it’s not directly applicable to building a company, I think it gives you a better appreciation for how the world works and what motivates individual actors.

Alejandro: I would assume as well when you were there, most of your classmates went into either consulting or to banking or things like that where they give you like really interesting offers, but you decided to join Google. We’re talking about 2006, so how did that happen for you?

Shoaib Makani: The natural path at schools like LSE are even NYU is very much down that finance and banking path, and that’s something that I did consider. But recognizing that my instinct was to build a company. I knew from very early on that I wanted to be an entrepreneur. I wanted to solve problems. I very intentionally chose the technology and company path, and Google was the ideal place to be at that time. It was a company that while it had very meaningful success in its primary market search, it was ambitious in aspiring to start many other adjacent businesses. So for me, it was an ideal platform. You know, you get the security of an established business that is still growing at an incredible rate, but one that is innovating in many different areas. The specific team that I joined Google Checkout was really a startup within Google. It was trying to build a modern, universal shopping cart experience or check out experience across the web, which was a very ambitious idea at the time. It didn’t fully work in the way that it was intended, but it was a great lesson in what it takes to build a great product at scale, and then actually distribute that product to both consumers as well as businesses at scale. It was both a B2C and a B2B problem, which was a really fascinating experience to come out of college with.

Alejandro: Some of those years while you were at Google were the super-hyper-growth years as well. So what was the biggest learning or I would say the biggest takeaway from your time at Google?

Shoaib Makani: I think what I really gained an appreciation for was the importance of a clearly articulated vision that then translated into specific objectives that individuals could attach themselves to. Google is run on an OKR system, and every single team member and every team creates their objectives and key results that tie back to the company or team level goals. That is a really important process because it gives everybody purpose. I think that’s one of the things that’s really carried with me. When every individual on a team knows that the work they do matters, it results in better outcomes. 

Alejandro: From an appreciation perspective because employees love to be appreciated, or either from Google or your take on this as a whole and from a building culture perspective, how do you make sure that people are appreciated?

Shoaib Makani: I think recognizing performance and recognizing success and wins, celebrating those, the individuals, but also the team’s results are so important. There’s nothing that drives a culture more than growth. So when individuals are growing, when the team is achieving its collective objectives, you have to celebrate those moments, and you have to recognize those individuals. Growth is king.

Alejandro: I 100% agree with that. I’ve read a couple of articles recently where they said that it doesn’t matter how many ski trips or retreats you do for the team that if the metrics are not working out, people are going to end up leaving.

Shoaib Makani: Yeah, absolutely. Yeah. The best people want to grow personally and professionally. Growth can be delayed, but there always has to be the potential for growth. The things you’re working on, you have to believe that they’re going to result in an outcome, that they will change the trajectory of the business. Great people are willing to tolerate that period of investment for delayed return, but at some point, there has to be a return.

Alejandro: 100%. After the experience at Google, you made the decision to move on, and you joined AdMob. What was that transition for you like?

Shoaib Makani: I knew I wanted to gain an appreciation for what early-stage company building was like. If you think about the trajectory of my career, I started at Google, a large company, but still was innovating. Then I wanted to go to a smaller company to see what it takes to build something from scratch. At AdMob, I joined a middle-stage after the Series B, so it was already on its way, but there was still a lot of work to be done. What I got to see there was how do you take a business that’s working in one market and expand it to many markets simultaneously in parallel? So I got to be a part of the growth that we undertook internationally. I started the Latin America business for AdMob, and then also scaled the India business.

Alejandro: I see here, you went to Latin America, India, Asia Pacific. I’m sure there are some people listening to us that are thinking also about doing their international expansion, so what were some of the key learnings about doing an international expansion?

Shoaib Makani: Number one, you have to hit the right markets. You have to make sure that you understand what your current capabilities are, what your product is, and how does that fit to the market need. Let’s say the product is universal. It is relevant for all markets. Well then, you’ve got to understand what is the market opportunity, and what is your ability to capture the opportunity in any one of those geographies? What we actually did at AdMob was we sized the internet market, just sheer volume of users and traffic because we were working for an ad network. We had inventory, and we wanted to fill it. So we looked at where do we have inventory? Then what is the demand for ad inventory in those markets? Based on the expected value, really the combination of where is available inventory and what is the potential yield on that inventory in those markets? We determined what was the priority. Some of them were not obvious where there wasn’t inventory today, but there was very high demand for advertising where there was a sophisticated ecosystem of advertisers who were looking for performance or looking for an audience. So we made some forward investments and then we also prioritized those simply where we had inventory, and we knew we could monetize it purely because of the volume.

Alejandro: Got it. One of the things that happened, it’s interesting because you moved on from Google, but essentially, it goes back to Google because Google acquired AdMob for 750 million. So how was that experience?

Shoaib Makani: It was pretty incredible getting to be part of a growth story, and getting to see a business scale, and then being recognized for that success. AdMob was the leader in mobile advertising, and the market was at the precipice of incredible growth, and getting to have a platform like Google to be able to realize that, scale that, and expand that was amazing. So yeah, I returned to Google and stayed for a year and got to integrate the AdMob business into the broader Google teams, which was a great experience as well.

Alejandro: You know, most acquisitions fail because of integration. Integration is a beast. My understanding is that Google has this unbelievable assembly line in order to acquire and then also to integrate the business. What does that look like? Why are they so effective like this?

Shoaib Makani: When you think about Google’s footprint, it has product engineering as well as sales and go to market in every region of the world. So just given that our business was already international, we had publishers and ad inventory in every market, and that was growing at an incredible rate. Getting to essentially access and distribute that further gained publishers through the Google sales footprint, but then also plug into the ad engine and ad demand that Google already had was incredible. It was a perfect fit in that sense, and Google, at this point, was well equipped to introduce new products into its sale’s channel. It was already selling AdWords, AdSense, YouTube, DoubleClick. So AdMob became another channel for Google advertisers to be able to reach an audience. It immediately drove an improved yield better performance for our publishers, which then continued the flywheel.

Alejandro: At this point is when you start thinking to yourself whether it makes sense to do an MBA or not. Then Khosla Ventures comes along. How were you introduced to them?

Shoaib Makani: It was absolutely random by chance. I was in Barcelona with some friends. I got introduced to a gentleman by the name of Ramy Adeeb who was on his way out. He was starting a company. He was at Khosla at the time, and he was on his way out. He was like, “Hey, you should meet the team, and so I did.” After a few weeks of conversations, I decided to join Khosla.

Alejandro: So now you’ve been used to the operator’s side to really understand how things develop and how execution looks like, especially at a hyper-growth, and then also how transactions are done when you’re really on the day-to-day. But now, what did it look like being on the other side of the table where you’re more like at a 30,000-foot view and really more involved in strategy and pattern recognition?

Shoaib Makani: I very intentionally went into Venture with the intention of starting a company. I believe that by seeing a lot of different companies and a lot of different teams, I’d gain a filter for what good opportunities look like. I think I came away with that. I think really Venture does give you a taste for businesses where growth can compound at a high rate for extended periods of time in a relatively capital-efficient way. So what you start to recognize is, what are the characteristics of those businesses that have the potential for that high growth, that high compounding growth. So what I gained was, the market has to be big either directly or through adjacent opportunities, and the adjacencies have to actually be accessible. You can’t start a company that’s going to sell windshield wipers and then say, “I’m going to build a car.” There has to be true accessibility to those adjacencies. Then my personal filter was product-driven customer acquisition advantage that incumbents can’t replicate a truly durable advantage. Or it has to be a new market that you believe can be big and that the early mover can sustain its advantage and pull ahead. So that framework and that mental model for being able to evaluate opportunities, markets, and teams really allowed me to actually apply that to the companies or the ideas that I was pursuing.

Alejandro: To this point, you said you went in it with the intention of building your own business. Was there a point in time where you said, “I’m going to do it. It’s not a matter of if, it’s a matter of when?

Shoaib Makani: Yeah. I mean, my primary responsibility, of course, was to invest in companies. I did that at various stages, but I was fairly thesis-driven in my outbound approach. I picked a few specific markets that I thought were big and where there were gaps or markets that I thought could be big and that hadn’t been filled out. So logistics happened to be one of those that I took an interest in and went deep. I went and really evaluated all the consumer on-demand companies across ridesharing, deliver, food, and made some investments there. Then I turned to the commercial side, the movement of goods for businesses and looked at the full supply chain there as well. That’s where the opportunity emerged, and I didn’t see anybody filling it. I was looking for companies that were essentially connecting supply over the road trucking. That, to me, was the big underserved opportunity, and I am a supply-first marketplace guy. I think if you can bring supply online in a disconnected, disaggregated market, demand will come. And when I looked at over-the-road trucking in North America, it was deeply disconnected and hyper-fragmented. The trucks, the drivers themselves were not online, and I didn’t see anybody attempting to connect them in a meaningful way. So that was enough for me to gain conviction that there was an opportunity here. The market was big, and I identified what I believed was a unique go to market and product-led customer acquisition advantage that could then give me access to the broader opportunity. It was a narrow entry point into a much bigger market and one that I thought we would have a fundamental advantage in executing on.

Alejandro: What was the triggering event for you to tell the Khosla guys, “Hey, I’m going to pursue this, and I’m going to go at it?”

Shoaib Makani: You know, you study the market, you research, you start socializing with others. Once I had the foundation of a team that I thought would be necessary to go and realize it, I personally had the conviction that we would be creating value. I didn’t know if it was going to work, but I thought that it was possible and highly likely that our narrow entry point – and I can elaborate on this. We thought we could build a relationship with drivers by solving a very specific problem around compliance that they faced and that drivers would self-adapt our product. Once I had that confidence, I knew that there was going to be some value that we create, and then it would be a matter of how did we expand and extrapolate from there? So once we had that early conviction, and I believed I could raise funds and money, that was enough for me to say, “All right. This is it.”

Alejandro: And what made you believe you could raise money?

Shoaib Makani: One of the benefits of working in Venture is you do build a network. You start to meet investors who are looking for early-stage opportunities, and then you also really do gain an understanding of what it takes to attract capital, and how to tell a story. It has to be a credible story. But I thought I had all of that: a big market, a unique entry point, and a good team. 

Alejandro: I really love that, Shoaib when you say about the story, and I tend to agree with you that storytelling is everything, especially as an entrepreneur because that’s how you onboard investors. That’s how you onboard customers, partners, and even talent, your most important key people. So what does, and especially with what you have learned with Khosla Ventures, what does storytelling at its best look like?

Shoaib Makani: I think you have to start with a view of what the world can be. You have to have a vision, and it has to be compelling. Investors and venture investors aren’t looking for 3x, 5x returns, especially not in the early stages. They’re looking for the 100x. So you have to either describe the market that is already big that you can take a piece of, an outside piece of, or one that is emergent and that you have the unique opportunity to actually expand. So it has to start with that vision of what the world can be or will be, but then you have to be able to say and credibly present the path to get there. And no big company has started overnight. Every company that got big started with a fairly narrow entry. So I think what you have to be able to tell is, there’s this big vision, and the way I’m actually going about this – my Step One gets me in the door and gives me the potential to realize the vision. That step one has to be believable and practical, and you have to be the right individual or the right team to be able to actually derisk that one. So I think being able to tell that story, and how you’re the right fit for the Step One and for the extrapolation, realizing the potential, that’s what compels investors.

Read More: Charlie Bachtell On Building A $600 Million Cannabis Business With 1,800 Employees

Alejandro: I guess putting this into perspective, how did you use – obviously, you had the idea. You were looking at the market, and you saw it from all different aspects. You invested in companies like Instacart, Indiegogo, Everlane. You really understood what you were about to get into. So how were you able to first and foremost identify your members of the founding team, and how did you convince them to join you?

Shoaib Makani: I’ll start with Obaid. Obaid Khan, my co-founder, and head of operations, he actually was on a very different path. He was thinking about going to law school. He had been working in policy in D. C. I actually, very early on, was like, “This is an interesting market, Trucking Logistics. I think I have an angle here. I want you to help me validate it.” I had the good fortune of finding him when he didn’t have a job. So he actually just ran with it. He started hanging out at truck stops, calling up brokers and carriers, and just really validated the hypothesis. It was great to have someone who could do that fulltime because I couldn’t at the time. He really ran with it and gave me and us the confidence that there was something here. Then my co-founding CTO, Ryan Johns, I knew him socially. He was a good friend, and he had been trying to build a company. I had talked to him as an investor to potentially say, “What are you working on? Could we potentially fund it?” He ended up not moving forward with the project he was working on at the time. When I zeroed in on, “Hey, this is the right opportunity.” I went to him and said, “Is this something that you would be interested in collaborating on?” It was really the good fortune of finding both Obaid and Ryan at the right time for them individually, but them also being the perfect complements and the right founding team that was, I’d say really complementary but also super cohesive. We got along. We were incredibly patient with each other, and we believed in each other in a way that is absolutely necessary if you’re going to embark on a multi-year journey to solve a really hard problem.

Alejandro: Of course, and what were the early days like?

Shoaib Makani: They were a grind. We got started in June 2013 in earnest and recruited about five other people to our founding team. There are eight founding team members, seven of which are still at the company six years later. We really set a very specific and clear vision of what we wanted to do, and we didn’t get distracted. It was actually pretty uncomfortable because we didn’t generate revenue for the first three-and-a-half years of the company. We took the view that we wanted to connect supply. We wanted to connect drivers. The way we were going to do that was through this compliance requirement. So just to elaborate on that a little bit more, if you drive long-haul in North America, you have to keep a record of what you’ve done. There are rules that dictate how many hours you can drive consecutively in a day or in a week, and drivers have to create a log form. It’s essentially a 24-hour grid. There’s a page for each day, and they have to document when they’re on duty, off duty, and driving. This paper-based workflow was the standard at that time. That was what we were solving. We thought if we can go and create a better experience for logs and translate that paper experience into a mobile application, our bet was that drivers would self-adapt it, and they’d tell each other about it, and they’d actually bring us into their companies. And we gave it away. I’d seen bottoms-up adoption work in the enterprise as an investor, Expensify, Dropbox, Yammer, and I believed it could work here as well. We stayed super-focused on that specific problem building a free service for drivers and a complementary web application for fleet managers and safety managers to be able to view their driver’s logs, communicate with their drivers, and digitize these otherwise paper-based workflows. We took the long view. We thought, “We will monetize this, but right now, we want to put nothing in the way of adoption.” So we gave it away and got hundreds and thousands of drivers using it the first few years, which gave us the confidence that we were building value even though we weren’t generating revenue. We weren’t capturing much value, but we were definitely creating it. I’ll say, we got to hundreds and thousands of drivers using the free application, but it took time. For the first year, we’re talking about a few thousand, but we saw that our users loved it. Even though the numbers weren’t there, the anecdotal and the qualitative data was very clear that there was something here. We stayed focused on it and didn’t let any of these distractions depart from our vision. 

Alejandro: You know, it’s very interesting that you touch on this point because now we probably have listeners that are joining from all over the world. The mentality and the mindset on how you build a business, or how you invest in businesses I think is probably different from the U.S. than what you would see, let’s say in a place like Europe or Latin America where it’s a little bit more revenue-geared. So how did you develop this mindset starting from Khosla on growth versus profit as you were thinking about building the business?

Shoaib Makani: Yeah. Look, you have to have the potential for profit ultimately. I mean, that’s what businesses thrive on: compounded revenue growth and eventually earnings. So we weren’t building this with no sight toward monetization. We believed that this audience was highly valuable and that we were very close to revenue when we were ready for it, and when our customers and users were ready for it. We architected the company to be able to survive that period of no revenue. I raised a fairly sizeable seed round, and we kept the team incredibly lean. We didn’t really raise our A for another three years after that. So we made sure that the decisions we made and the money we spent aligned with our revenue plan and our growth goals. But ultimately, yeah. You have to make money. That’s where we knew that we had an upsell, that we would generate revenue from our audience, and then recruited the team. We actually had to build hardware because we’re a hardware-enabled SaaS company. We had to build a team and competency and hardware to be able to then drive revenue growth, but in the meantime, continue to expand our install base, our userbase, and demonstrate it to investors that the value was there – that the potential to capture value was clear.

Alejandro: Got it. So for the people that are listening, just so they really get a grasp on it, what essentially became the business model of KeepTruckin?

Shoaib Makani: What we do is, we essentially sell hardware-enabled premium services. We go in, and drivers use our free application. Fleet managers use our web application to manage compliance, to communicate with their drivers, and track their location. Then we have hardware that we designed and developed that brings the truck online; brings the vehicle online. So you install our hardware into the diagnostic interface of the vehicle, and it’s a Linux-embedded computer that attaches to the vehicle, and it records all the data off the vehicle network like how is this vehicle operating? How fast is it going? Is it safe to operate? Then we’ve got a number of sensors in the device itself which help us understand what the environment of that vehicle is. So that enables premium telematics offerings, premium compliance offerings for our customers. More recently, we’ve introduced a dashcam, so you can connect a video camera into our vehicle gateway to get real-time critical event video. You can recall video and say what happened two days ago at this stop. If there’s an accident, you know exactly what took place. Here in the next month or so, we’re going to be introducing our Acid gateway, which is essentially a device that lets you monitor any asset, any type of equipment whether it’s a trailer, or construction equipment, or anything that you own and operate. So what we’ve expanded into is an IoT sensor platform for commercial vehicles and commercial equipment so that you as a company, as an operator, as a safety manager, as a fleet manager know exactly what’s happening with your drivers, your vehicles, and your assets no matter where they operate. We started in trucking because that was our entry point. But today, we service all types of commercial vehicle fleets. But importantly, we’re a hardware-enabled SaaS business for commercial vehicles by we’re also building a freight-marketplace that allows anyone to access our network of trucks because we have more for-hire connected trucks in North America than anyone. It’s a unique combination of a SaaS business, but a marketplace business, which you don’t see too often.

Alejandro: Very cool. And for this, how much capital have you guys raised to date?

Shoaib Makani: We’ve raised around 230 million dollars of capital.

Alejandro: Very cool. And also, I heard that you guys passed the billion-dollar valuation. So that’s pretty amazing. I wanted to ask you here when you went at it, and obviously, you guys raised money fairly quickly. You started the business, and then it seems that the first year you just got the round right away, but when you were thinking about the fundraising process – I mean, I always tell founders that they need to think about not the round that they’re raising today, but the round that they’re going to raise at a later date because the way that they raise now is going to impact the next round. So before you were raising your first round, did you already like model out like the different rounds were like the potential financing milestones that you were going to have to encounter down the line?

Shoaib Makani: Yeah. You definitely have to anticipate your capital requirements, and that informs your hiring, your revenue goals, how you actually make bets. But you can’t overengineer it. These things are very fluid. It’s almost impossible to project exactly where you’re going to be in a year or two years. Entrepreneurship is not a straight line.

Alejandro: Yeah.

Shoaib Makani: But it is important to plant, and then to make investments against that plant. But also, be able to adjust course either when things are working better than you expected or less well than you expected. We had to do that along the way. There were times when we were behind plan, and we actually had to reduce the team size and extend our runway. Difficult decisions, but ones that you have to make to give yourself a chance because most companies don’t lose to others. It’s not that they get beaten by competitors. They generally lose to themselves. Either they run out of money, they don’t build the right things, or they just don’t give themselves enough time to realize the vision or for the market to come around. So being able to plan ahead and anticipate your capital requirements is important, but also, I think more important is having the ability to understand where you are in real-time, in the moment, and where you need to get to that next milestone, and then being able to adjust course and either add resource or remove resource to be able to give yourself a shot.

Alejandro: You know, it’s interesting what you just mentioned that you guys have to scale down a little bit the team. Some of the best founders that I’ve met are those that are able to also make the difficult decisions during difficult moments. So, for example, from your own experience, it’s really tough to really detach yourself emotionally when you go through a moment like that. So how do you do it to really become effective?

Shoaib Makani: I’d say it’s easily the hardest decision you’ll ever make as an entrepreneur is to let people go. But what you have to rationalize is, “I’m doing this so that everyone else has a chance; so that we have a chance. If we have a chance, and we believe that we’re building something of value, we’ll actually grow out of this. In fact, in our case, we had to reduce our cost, extend our runway. This was early on, and once we broke through because we actually knew that this market was going to come around and that we were creating value, we ended up hiring back multiple people that we had let go, and they wanted to come back because we did it in the right way.

Alejandro: I 100% agree with you that during those times, it is what it is, and it’s either you make the decision, or the entire boat is going to sink. You need to cover the holes, but I think that it’s all about the delivery of the message; not the message itself. If the delivery has integrity and transparency, people are not going to have any type of thing against you or the business because their memory is going to be a positive one. 

Shoaib Makani: Yeah. I absolutely agree, and I always say, “It’s not just about the what. It’s the why.” That applies to every communication. When you give people an understanding of why you’re making the decisions you are, why we’re doing the things we are, both positive and negative, the context then helps them understand their place, and why their word matters, and why these decisions are being made, and it results in absolutely better outcomes.

Alejandro: Going back to the fundraising. You guys have onboarded amazing investors. Obviously, Index Ventures, Google Ventures, Institutional Venture Partners, Scale Venture Partners – really, really great investors. For you being an insider, someone that really knows the dynamics and the people, and more importantly, the quality of people because I find that at the end of the day, it’s all a matter of really having an understanding on how people are going to behave when you’re on the other side of mountain because people can be very nasty and very ugly during those times rather than on the good times when you’re dating, and everything is beautiful, and everyone is happy. But from your perspective, what was the absolute must that you required of people in order for them to become investors in Keep Truckin?

Shoaib Makani: You know, I had the experience of seeing what different types of investors look like and how they behaved, having been a VC, and having been on boards. So I knew the profiles and the behaviors that were desirable – the type of people who I wanted to work with. So when you have the ability to choose your investors, when you have multiple options, you’re always going to gravitate to those who align with your own philosophy. What I look for are investors who believe in your vision. It can’t be that they believe in some augmented version of your vision or their own, and they want you to realize theirs. They have to believe in your vision. They have to defer to the founders. It is so important that you work with investors who believe in you and realize and recognize that you’re the one that’s day-to-day in the business and that you’re the one that ultimately has to live with the decisions. So I absolutely believe investors should be deferential toward founding teams and management teams in general. So that’s a really important quality. But then also, investors who push and encourage us to be our best. Don’t let us tolerate mistakes or let mistakes persist. So I think it’s the right balance in belief in the vision and deference to that team, but also candid feedback delivered in a way that helps you understand what the alternative looks like – what other companies do, bringing that broader context I think makes the entrepreneur better because we’re really narrowly focused on our business. We’re heads-down, and it is helpful to gain that broader context. A great investor actually can help deliver that in a very productive way.

Alejandro: Yeah, absolutely. So for the folks that are listening to really get an understanding on the scale of what you guys are doing today, how big is the operation of Keep Truckin?

Shoaib Makani: We’re about 1,200 people globally and distributed across multiple geographies. On our R&D side, we’re about 200 engineers across hardware and software. We have a very substantial go to market footprint because we sell to small companies, small businesses and fleets, so we have many hundreds of sales reps and support reps, and then a significant operations team to tool the business and make sure it can run at scale.

Alejandro: Very cool. One question that I typically ask the guests that I have on the show is if you had the opportunity to go back in time and have a chat with your younger self before, let’s say, starting Keep Trackin, and you were able to tell yourself one piece of business advice, what would that be and why?

Shoaib Makani: That’s a good one. I think if I were to start another company today, I would make talent acquisition, recruiting a part of the founding team. It sounds crazy, but the biggest constraint on our business has been the ability to recruit great people because once you have product/market fit, a distribution advantage, and a very large market, the only thing that really conditions your potential is great people to execute. That applies across product engineering, sales, ops, marketing. So really being able to attract – and not even attract, but go and pursue great talent efficiently really was a limiting factor for us, and I wish I had solved it sooner. 

Alejandro: So would that, as you were saying just to follow-up on this building – bringing some money to the founding team that could help on this front, would it be someone that has a background in a [47:15] or someone that has a really super, big network to tap from, or what would that look like just out of curiosity.

Shoaib Makani: Generally, it’s like you run out of network-driven recruiting fairly quickly. Referrals are obviously a matter at scale. More than half are hires, I believe, are referrals at this point. But no, it’s just someone whose only job it is to identify what our gaps are – we know what our gaps are. We know what the biggest problems in the business are from a resourcing perspective. But someone who can then go and make it their only and sole focus to go and fill those gaps because when you’re 8, 10, 12 people, everyone is consumed in their specific problem, and they don’t have time or energy to go and solve other problems to fill other gaps. That’s where having someone whose fulltime job it is to do that early just lets you grow faster and get better people. That’s something that I think we were late on. I think, again, as soon as you have that confidence that this is going to work, it’s absolutely important to double down.

Alejandro: Got it. That’s very powerful by the way. So for the folks that are listening, what is the best way for them to reach out and say hi?

Shoaib Makani: I’m happy to connect with anyone who’s interested in learning about what we do or interested in entrepreneurship in general. They can reach me on LinkedIn or on Twitter @smakani.

Alejandro: Amazing. Well, Shoeib, thank you so much for being on the DealMakers show today.

Shoaib Makani: Thank you so much for having me, Alejandro.


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Neil Patel

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