Joshua Motta On Selling His First Business To Microsoft At 15 And Now Raising $50 Million To Keep Companies Safe From Cyber Crimes

Joshua Motta is the co-founder and CEO of Coalition which protects the value of a business with Coalition’s intelligence, risk management, and insurance offerings. The company has raised over $50 million from top tier investors such as Hillhouse Capital House, Ribbit Capital, Vy Capital, Valor Equity Partners, and Greenoaks Capital to name a few.

In this episode you will learn:

The simple secret test for finding the right cofounder
The first hires Coalition made
The benefits of a small startup team
The first document was written to ensure business success
How to avoid making the wrong hires
How he turned down $20M to start a business twice
His number one piece of advice for anyone working in corporate America or considering a startup
Why Joshua created a 70-page long-form business plan for his most recent company

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About Joshua Motta:

Joshua Motta is the CEO and Co-founder of Coalition, the fastest-growing provider of cyber insurance for small to medium-sized businesses.

Having worked at the intersection of the intelligence, finance, and technology sectors at the CIA, Goldman Sachs, and most recently as an early employee and CxO of Cloudflare, Joshua Motta gained valuable insights into the minds of hackers and how — and why — they target specific organizations, as well as how organizations can most effectively manage cyber risk.

Joshua Motta founded Coalition to provide a better way to protect small and midsize businesses from breaches and cyber incidents.

Connect with Joshua Motta:

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FULL TRANSCRIPTION OF THE INTERVIEW:

Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. Today we’re going to be learning a lot about cyber insurance and the entire process of going from corporate America to doing your own thing and building something meaningful. So without further ado, let’s welcome our guest today. Joshua Motta, welcome to the show.

Joshua Motta: Thank you for having me.

Alejandro: Originally, you were born and raised in Kansas, so how was life there growing up in Kansas City?

Joshua Motta: Life was maybe a bit boring, but that gave all the more time to focus on fun things like technology.

Alejandro: Now, you’re in San Francisco. Especially for the folks that are listening in the Bay Area that are wondering, how different is Kansas to being there in the Bay Area?

Joshua Motta: Looking back, I appreciate it far more now as an adult than I did as a teenager. It’s a wonderful place to grow up and an idyllic life, but you certainly don’t have access to all the different resources you have here in a city like San Francisco, for sure.

Alejandro: You did have, at least, access to technology, and that was your outlet. Tell us about this.

Joshua Motta: Yeah. I was a lazy teenager. I’d like to say I was hardworking, but waking up at 3:00 or 4:00 in the morning to do a paper route never appealed to me. So technology was the outlet. I started as an entrepreneur. I started with the help of some family members, uncles, self-taught myself HTML, and some other programming languages. I started building websites for local retailers and local businesses. One thing led to another, and my co-founder and I found ourselves being acqui-hired and employed by Microsoft. I’m proud to say that my first job was not running a newspaper route. It was programming for Microsoft at the tender age of 15.

Alejandro: That’s amazing because you guys were powering [0:03:17] and that’s how everything started.

Joshua Motta: Yeah. It just so happened that one of our clients was featured in a Microsoft publication, that led to us being featured, and then one of the most senior Microsoft executives, Jeff Raikes, who had himself grown up in Omaha, Nebraska, not far from us, sent us an email. He took time out of his day to congratulate us on what we built, and that email ultimately led to becoming — I think at the time, I was the youngest person to have worked at Microsoft. I’m sure that record has since been shattered, but it was a really fun experience.

Alejandro: That’s amazing. You were literally 15 years old and you had your own business and your own clients and all of that stuff?

Joshua Motta: Yes. Believe it or not.

Alejandro: I’m asking you because I think at 15, I was playing PlayStation and doing the paper route that you were mentioning earlier.

Joshua Motta: Yes.

Alejandro: That’s amazing. So how was the experience of Microsoft?

Joshua Motta: It was wonderful. Jeff and everyone at Microsoft were incredibly gracious. It was a formative experience in my life and set me on a different path. Obviously, having Microsoft on your resume and being the youngest person to have worked there opened up a number of doors for me later on in life. I’m grateful for the experience. I’m grateful that Jeff took time out of his day to send a congratulatory note to someone who he didn’t know.

Alejandro: Then, you did some experiences with Sprint, with Honeywell, and that led you to the University of Chicago.

Joshua Motta: Yes. I worked in a number of jobs throughout school. I wanted to stick closer to home in Kansas, where all my friends were. I was fortunate enough to enroll at the University of Chicago and also simultaneously joined the Central Intelligence Agency, which was another formative experience of my life. It exposed me to a very different side of technology and how it’s used in the CIA’s mission to protect the country.

Alejandro: What were you doing there? It’s unbelievable.

Joshua Motta: I guess this is where you typically invoke the typical phrase of if I told you, I’d have to kill you.

Alejandro: Hopefully, not.

Joshua Motta: Hopefully, not. A number of mundane things from analysis of how other countries are using information technology in a way that’s either beneficial or not to the U.S. and also working operationally on different information operations.

Alejandro: Now, you were exposed to this, and it seems quite exciting, especially coming out of school. Why did you decide to go to the financial services, which seems a little bit more boring than CIA stuff?

Joshua Motta: Yeah. It definitely sounds boring. I feel like at some level, I was a victim of my own age. I joined CIA younger than most do, and to do some of the more fun things you have to be in your mid-20s, I want to say. So as opposed to waiting around for that, I decided to go out and try another job, try another role. I ended up working for Goldman Sachs in London on the investment banking team, still focused on technology companies. But, again, it exposed me to a very different way of looking at the world, and one that was maybe more measured by risk than perhaps technical accuracy. It’s the culmination of all the things that I’ve done that have led me to where I am today.

Alejandro: Probably, the most meaningful experience — I think that all of them are meaningful, but one that really shaped you was being able to be part of Cloudflare. But before we talk about Cloudflare, I want to ask you because you did investment banking, and you also did private equity. In investment banking, you were able to see how you were able to package companies and how to make deals happen. Then, perhaps on the private equity side, maybe you were a little bit more involved into understanding all the pattern recognition of what makes some deals have good potential down the line. Can you expand more on what you learned from the investment banking experience, and then also, from the private equity experience?

Joshua Motta: Yeah. Absolutely. Like you said, it gave a very good understanding of the fundamentals of what is a good business, what’s an investment-worthy business, pattern matching to understand which are great and which are not. I’d say the other fundamental thing that it helped with is thinking about risk. At some level, whether in private equity investing or in investment banking, you’re making risk calculations all the time, maybe without realizing it. But it gave me a deeper appreciation for that risk calculation, which is at the core of what we do in cyber insurance today.

Alejandro: Could you expand on calculating risk? How do you do that as a founder?

Joshua Motta: Yeah. For sure. As a founder, running a cybersecurity company is very similar to running any type of company. You need customers. In order to get them, you need to understand and solve their problems. Whether you’re an analyst, an investment banker in private equity, fundamentally, what you’re trying to do is understand the endogenous and exogenous factors weighing on that company. You need to understand their customers. You need to understand the problems that company’s customers have and assess that company’s ability to meet them. Obviously, where those things match up, customers have significant problems, maybe sometimes, intractable problems — the other company that has found a novel way to solve them. Not only are those great investments, those are great businesses. I’ve always tried to think as an investor, even as an entrepreneur, because maybe at some level, we’re not investing our capital. We’re investing something more precious, which is our time.

Alejandro: Yeah.

Joshua Motta: Every entrepreneur has a finite amount of time. So, you better be extremely certain that you’re investing that time in the most productive way.

Alejandro: Got it. And you did a very good job at investing your time because when you gave up your role with the private equity firm, you joined a company that was just 20 employees, and now that company is right at 5.3 billion. So you definitely knew where to invest the time. Tell us about the experience with Cloudflare.

Joshua Motta: I grew up and was one of the first users of the modern internet. The mission of Cloudflare was, from the start, build a better internet. That’s a mission that hasn’t changed to this very day. It’s something I’m proud to say that looking back, the company has done in a very meaningful way. I’ve always viewed it as: it takes as much time to achieve a large vision as it does a small vision. That’s been something else that’s been impactful for me as an entrepreneur that was very impactful for us at Cloudflare. We, literally, as a 20-person startup, believe it or not, we were out to rebuild the internet and to build a better internet. Today, I think Cloudflare’s used by — I forget the last statistics, but I think over 17 million websites, so it’s been quite impressive what they’ve achieved starting with only 20 people.

Alejandro: Wow. You were part of all that incredible growth. Right now, they have over 1,000 employees, 5.3 billion market cap. For you, from that experience, what were your biggest takeaways.

Joshua Motta: My biggest takeaways — the vision was one, big visions. None of us at Cloudflare worked any less because we were working towards a small vision. It was large. I think the other was that mission is important. Companies are groups of people who are all highly-focused and talented working towards a common objective to the extent that you have a mission to get very talented people to buy into, whether that’s building a better internet in the case of Cloudflare or solving cyber risk in the case of Coalition, it goes a long way to recruiting the groups of people you need to build incredible companies. The narrative is important. The way in which you talk about your mission, you tell your story. I found that people, whether they’re respective employees, customers, stakeholders, the general public, they’re far more apt to buy into why you do something than what. If I was to describe to you what Cloudflare did, everyone would be snoozing by the end of this podcast. The why Cloudflare’s doing it, that’s what’s powerful. Those are some of the key lessons that I took away and have incorporated into Coalition.

Alejandro: Than, as an entrepreneur, how do you find your why?

Joshua Motta: That’s unique for everyone. In my case, I guess you could say I’ve taken somewhat the renaissance approach to life: software engineer at Microsoft, CIA, investment banking. To the layperson, maybe it doesn’t appear that there’s any connection between these things, but from my perspective, the Coalition is the culmination of these things. We’re bridging the technology world, the intelligence world from a data-collection perspective and the financial services world, we offer insurance or risk-transfer mechanism by bringing all these different experiences that I’ve had together to solve a problem in a novel way. I’ve always referred to it as first-principles thinking. That was one of the other valuable takeaways. I think at Cloudflare, we were very good at not thinking by analogy, not looking at what everyone else was doing. We wanted to blaze our own path and try and tackle and do things that no one else thought was possible.

Alejandro: Obviously, your route as an entrepreneur started with a former colleague from Goldman Sachs that was trying to convince you. And the third time — the third time is a charm. So, tell us about this.

Joshua Motta: On a number of occasions, he tried to get me to leave my place of employment and join him. He offered me 20 million dollars to go set up whatever company I wanted to. Believe it or not, I told him that I didn’t have an idea, which seems crazy to me that I would have said that at the time. But I was just so busy building Cloudflare and had such respect for him I didn’t want to lose his money. The third time, he brought me the idea. He brought me the team, and I was sold. I’d always wanted to work with him. So my route to setting up the company was perhaps a bit easier — someone offering to give me money to go start something. So I’m humbled as a result of it. I think that’s been a common theme in my life. People taking an interest in paying it forward, whether it’s Jeff Raikes, at Microsoft or Alexander Tomas, who, at the time, was at DST, but is now at his own fund, VY Capital. I’ve been blessed to have people who have been willing to invest.

Alejandro: What happened next?

Joshua Motta: I left Cloudflare, and I started the company called Redacted. Redacted was a cybersecurity company that I founded with a former Chief Security Officer for Facebook, and another cybersecurity entrepreneur who had started the company called Lookout. It was inside of Redacted that we started to build the initial building blocks at Coalition. Ultimately, it didn’t work out to build Coalition inside of Redacted, so we spanned the company out in March of 2017, and here we are today as one of the larger cyber insurance providers in the U.S.

Alejandro: Very cool. That’s interesting. You guys were launching two companies under the same roof. How was that possible?

Joshua Motta: It wasn’t, I think, is the short answer. Looking back, things always seem like they’re smooth, and they happen easily. This is one of those cases where they did not. It was very clear that one of my co-founders had a very different vision as to how to build the company than I did. At the end of the day, it blew up. We found it very difficult to work with one another. It ultimately impacted the entire team. I may be overstating it, but that was certainly some of the lowest lows in my life, personally and professionally, in terms of working it out. I think I had conviction for the idea. I was blessed to, again, have a bunch of people who had far more wisdom than I do, who helped see us through that situation. Our investors were also very supportive of us splitting the companies into two. Ultimately, it manifested itself and me leaving the company with a handful of other individuals who were focusing on the cyber insurance idea. The same lead investor who took me out of Cloudflare to fund me at Redacted did perhaps the crazy thing and decided to do it again with Coalition and give me even more money to go start yet another company, even working through the difficulties I was having with the other co-founder. Perseverance paid off. There is a point in time when I just didn’t know if I had the will to go out and start another company. That was maybe the first major setback for me career-wise, and I definitely can’t say I was terribly prepared to take it, especially after having, whether it’s a run of luck or otherwise. In my previous endeavors, this is the first hardship or adverse event I had run into. As an entrepreneur, you have to keep your optimism, keep your conviction for what you believe in. I was fortunate the other employees at Redacted, who started with this idea, believed in me and were also willing to leave into the unknown to start Coalition.

Alejandro: I’m sure that for you, this was quite an emotional rollercoaster. From this experience, I’m sure that when you have these types of disagreements, I think that you need to take communication to a whole other level to find a path forward. How did you do that in your case?

Joshua Motta: Yeah. I’m not going to say that we did it necessarily well. Anytime you have lawyers involved in your communication, you’re probably going down the wrong path. That was the path that we were on, but I think in terms of guiding those who I was leading inside of Redacted to leave the company with me and start it, again, it came back to having a clear sense of purpose of what we wanted to accomplish, what we wanted to do, why we were doing it. In my particular case, I had spent almost my entire life at the intersection of technology and mathematics. I had gotten to see, by virtue of being at CIA, a lot of the horrible things that other countries were doing to the U.S., and not the U.S. government, as everyone expected with warfare, but American companies. Ironically, after having all these experiences, I felt like we could do more to help American companies withstand technological risks, cyber-attacks, things of this nature as an insurance company than we ever could have, working inside a three-letter agency. So, perseverance and belief, and trying to solve a problem in a novel way, those were the keys to surviving that and guiding everyone else along with me.

Alejandro: And, you know, believe it or not, over 65% of companies fail because of co-founder issues. So, I think you were very lucky to be able to pull it together and continue. For the folks that are listening, that maybe are thinking about joining a co-founder or bringing a co-founder aboard, what would you tell them?

Joshua Motta: Bringing a co-founder on board, it’s like getting married. It is a marriage. In fact, you will spend more time with that person than you will your own spouse. That’s, in many respects, been my experience. Some of the conversations you’re having on a daily basis are far more difficult because you’re constantly in a place of stress. The way I’ve looked at hiring a co-founder is that the best co-founders will make your highs twice as high and your lows, half as low. If you found yourself in a relationship with a co-founder where that’s not happening, where you can’t share the highs with them, they don’t augment it or multiple it, and where sharing the lows with them makes things twice as bad if not half as bad, that’s a sign that there are problems that need to be addressed. That’s always been my litmus test from then on as to how I choose co-founders.

Alejandro: I have to tell you that is super profound. Your highs twice as high and your lows half the lows. I think it’s totally accurate and I love that. Joshua, let’s talk about Coalition. Here you go. You finally go into the unknown with this group of colleagues from the previous company. Now, they’re joining you. What happens next? Here you guys are. What’s the future? How did you go into that unknown?

Joshua Motta: Yeah. I think we saw a problem, a very large problem that we were all passionate about addressing. If you take a step back, which is always useful when you’re thinking about setting up a company, and you ask yourself, “What’s going on in the world?” I saw a graphic in The Economist magazine. It was a geological timeline of the earth, 4,500 million years old. There’s the small red dot on the bottom right that says, “You are here.” It was thought-provoking. It was like our species hasn’t existed for a terribly long time. But if you think about it, the story of our species is one of technological creation and adoption. The reasons for that are pretty obvious. Like, the productivity benefits of technology are massive, you get them immediately, and as a result, the evolution of technology has been staggering. It took 68 years for 50 million people to fly in an airplane and only three days for 50 million people to download Pokémon GO. Now, they’re flying around in airplanes, capturing Pokémon, so it’s full poetic justice. But while that was amazing, what we also realized is that with all the benefits of technology come these new risks. There’s not a company in the U.S. today, no matter what sector of the economy, it isn’t dependent upon a working computer, a working internet connection, and access to their data. If you take any one of those away, much less all of them, it can be existential. It can be company-ending even if you’re not a tech company. As we’re seeing this epidemic of ransomware, it’s been devastating, particularly to small-medium businesses that don’t have the resources to react or survive it. That was the genesis of Coalition. We wanted to solve cyber risk. However, solving cyber risk for us wasn’t like it was at these cybersecurity companies, which is like solving security failures. We knew that no matter how much technology you invest, how much money you spend, bad things are going to happen to good companies. That’s because solving a technology problem with more technology doesn’t make any sense. It’s circular. We didn’t view cybersecurity as a technology problem we viewed it as a risk management problem.

Alejandro: Joshua, how were you guys making money with this? With this problem that you guys were able to see, cyber risk and all of this, how were you monetizing? What ended up being the business model?

Joshua Motta: The irony is it’s difficult to make money selling cybersecurity, especially to small businesses because most of them don’t think they have the issue. Choosing between spending a dollar growing their company and a dollar in cybersecurity, no one’s been successful. That’s where it’s like the epiphany was: let’s sell an insurance product. Let’s pool this risk across the tens of millions of companies, small businesses in the United States. Let’s charge any individual one relatively small amount of money, and let’s make it affordable. Insurance is something that businesses are used to purchasing, and in many cases, they have to purchase. So, let’s monetize that way. Let’s monetize by selling the insurance product, and in doing so, create literally a coalition of businesses that share the same risk, pool together the insurance premium, the capital that they give us, and use that to then build the software, build the technology, give them the data they need for free to protect their companies. Then the beauty of it, as well, is that our incentives are aligned with theirs. We have an active incentive to try and give them technology that helps them prevent loses because the lower the loses they suffer, the more profitable and more competitive is the insurance.

Alejandro: Very cool. So how do you guys go about raising the money? You guys have raised quite a bit. How much have you raised so far?

Joshua Motta: We’ve raised 45 million so far.

Alejandro: Okay. Very cool. Can you tell us about the financing and how do you go about it? This seems to be quite innovative, so maybe something that investors were not as used to seeing, so what were the typical concerns and what were the typical expectations that you were seeing?

Joshua Motta: The concerns were, how is a startup going to sell insurance? Normally, insurance companies are worth tens or hundreds of billions of dollars. They’ve been around since 1792 or 1831. Why is anyone going to trust Coalition to provide insurance? The typical questions there: how are we going to get access to customers? Commercial insurance is entirely sold by insurance brokers, and of course, those relationships are all owned by these big incumbent insurance companies. Our answer was, one, that we weren’t going to fight the system, we were going to join it. We actually partnered with a number of insurance companies founded in the 1700s and 1800s. We worked with Swiss Re and Lloyd’s of London and a number of other insurers that give us the credibility and the financial backing to take risks and for companies to trust us. All the while, the company’s getting the benefit of our innovative way of underwriting of all these technologies that we’re building, as I mentioned. That was one. The other was that in doing so, by combining insurance with the technology side of the equation, helping companies prevent risks, we also provide all the instep response services when companies do have an instance to mitigate them. We effectively built a product that had never existed before. Normally, insurance is just there for after something bad happens. Coalition had built something that helps you before, to prevent the loss and during, to help you contain it or put the fire out because there isn’t a 911 if you’re a victim of cybercrime. We are that 911 for our customers. And then the insurance product. When we took that to insurance brokers, we knew that if we came to them and said, “This product is 10% better than what these big insurance companies are giving you,” they would have laughed us out the door. We had to show them that it was ten times better and that it was solving a critical customer-need, and also solving their needs. We made it much easier for them to place cyber insurance. That’s a process that used to take two weeks; we took it down to two minutes. So now, the broker was far more productive selling our product than anyone else’s. I think those were some of the keys to success and what we ultimately had to prove to investors.

Alejandro: In this case, you guys have been growing quite a bit, as well, the team. In the past year, according to LinkedIn, you guys have grown the team by 161%. So, not bad at all. For building a company of this nature, what were the most immediate hires that you needed to make this work?

Joshua Motta: It’s a bit more of a motley crew than you might have in your typical startup. Normally, the critical people are, you need software engineers. Oftentimes, the founder of founders are the product people. They’re the visionaries. They’re guiding what’s built. That was no different from us. Many of the first hires were software engineers to help us build our insurance platform, but we also needed people with insurance experience. We needed people that could go and present incredibly to the Swiss Re’s and Lloyd’s of London of the world and convince them that they should extend their balance sheet and their capital to us. We are effectively choosing which companies get insured, and they’re the ones taking on the risk. That involved a team effort, and it was at that focal point where people from the insurance industry, technology industry, and the intelligence community, all coming together to solve this problem, we were able to show these insurance companies that we truly had a novel way in which to assess the cyber risk companies and that we could build an unparalleled cyber insurance product, which they were all thrilled to do.

Alejandro: I’m wondering because now the world that we live in is changing rapidly, and you were eluding to it before. This cyber risk that people are not accounting for before, how this is going to be increasing over time because I think many people say that the next war is not going to be with people with guns, it’s going to be with people with cyber stuff. So how do you see this happening?

Joshua Motta: I agree. I think that cyber risk or technological risk, more broadly, is now the most pervasive risk facing our society, maybe a close second to climate change, which probably impacts everyone, as well. The thing is that the severity is also growing. So not only is it pervasive but when technology fails or when technology is used in a negative way, whether it’s warfare or whether it’s compromising someone’s privacy or disinformation, election-meddling, the severity is growing. The dependency on society and technology is also growing. It’s a recipe for a significant challenge, facing not just business operationally, but facing our society at large. How do we harness technology for all the positives, and how do we mitigate the negatives? Sadly, I don’t think we have an answer. Our answer is to try and price for them and try and help people survive them by pooling risks together.

Alejandro: In this case, now, you’ve gone from early-stage to growth stage. What does that shift look like?

Joshua Motta: It feels like a blur. As you mentioned, we started with four employees. We now have over 80. That’s happened in the span of two years. It’s remarkably quick. So, I’d say, one of the most difficult things is keeping a coherent culture, keeping a coherent mission because by definition, if you’re more than doubling the size of your workforce, half of them have been there for less than a year if you’re doubling in any given year. So we’ve tried to be very deliberate as to how we expand, but I’d say the core change in going from the early-stage to growth is trying to maintain the efficiency we had. A lot of people think that a greater number of employees is better. It’s remarkable what we did with the first seven employees we hired. With seven employees, we built the entire core of what exists today, and I would say that adding 70 more, it has not allowed us to expand our productivity linearly, that’s for sure. So focusing on that core cohesion of the team’s culture, of the mission, making sure we’re all driving toward the same things, and holding one another accountable to each other, that’s become far more important and far more challenging as a growth company than it ever was as a startup.

Alejandro: When I think about culture, and when you’re at a growth stage, culture is everything. Growth, early, whatever that is, culture is always everything.

Joshua Motta: Yes.

Alejandro: When I heard you speaking and especially where you’re coming from and where you’re heading, there’s one word that keeps coming to mind, and that is alignment. How did you get that alignment of everyone? When you were talking about the core, to me, it was alignment, it was what was coming out, and I’m sure that has been able to be translated from those seven people, for them to influence or to inject that excitement, as well, on the other 80 or whatever that is. So how do you go about that alignment?

Joshua Motta: I think so much of it is writing it down. That sounds a little odd, and perhaps it’s a result of some of the negative experiences I had or challenges I’ve had, but the first document we ever wrote at Coalition was the Culture document. It was a list of the cultural ideals that were important to us that we wanted to promote as values across the company and things that we thought were critical to being successful in a small company that’s growing quickly with the world changing quickly on the outside. Those were cultural traits like humility, authenticity, as I’ve mentioned before, like refusing to follow what others are doing. Blazing our own path and staying authentic to our vision — first principle’s thinking. Not hiring a-holes and I apologize if this is a PG-13 rating broadcast.

Alejandro: No worries.

Joshua Motta: There’s no surer way to kill morality and to lose people than to do that. So writing things down is another way of saying, “Be deliberate.” We had to be very deliberate about everything. The culture doc was written even before the business plan was written. We also wrote a business plan. For a lot of people, that’s in slide format. You see, the Business Insider sharing whatever slide deck got someone some massive funding round. For us, it was a 70-page business plan. It was long-form. We wrote it out. We documented it. It comes down to being deliberate, writing things down, and it is surprising how many entrepreneurs and how many companies don’t do that or skip that step because it just seems unnecessary. It takes too much time. We’re moving fast and breaking things. For us, slowing down to do those things I think has helped us considerably in this growth stage, and we are now moving much faster than we otherwise would have had we not been deliberate from the start. Those are the lessons learned in previous startups, where we made all those mistakes.

Alejandro: And I definitely like the a-hole lesson and principle there as part of the culture. But I’m wondering, because the thing is, when you get one of those a-holes, they’re like a cancer. They can destroy what you’ve worked so hard to create. So how do you sniff out those a-holes in interviews?

Joshua Motta: We share the Culture document with everyone. It’s setting expectations at some level. Like, “This is how we operate.” I think a lot of it, too, is setting the appropriate incentives. There’s a lot of pressure, especially with these superstars and people who think highly of themselves, they’re always wanting to bend the rules, to do things differently, etc. We’ve made it a practice to where you have to be willing to give up something to join Coalition. You’re not going to make as much money as you did in your former role at Facebook or Netflix or some large insurance company. You’re going to have to make a sacrifice. We call it an IQ test. It’s maybe not truly an IQ test. I don’t think that the people that don’t join us are stupid, by any means. It’s an IQ test for: do you fit with our company? We try and deliberately in the interviewing process and throughout every engagement we have, even down to the offer letter, we try and put people in a position to where you have to want to be here. You have to be passionate about the mission because if all you’re looking to do is be a mercenary and maximize your own personal gain, this is by far not going to be the best offer you get, and not going to be the best place for you. We have deliberately tried to make a Coalition a horrible place to work if you happen to fit those traits.

Alejandro: Got it. Very cool. One of the questions that I typically ask the guests that we have on the show — now, you have quite a bit of experience. All these companies, all this time that you’ve been building and scaling, and all this money, as well, that you’ve raised, my question here would be: if you had the opportunity to go back in time and have a chat with that younger Joshua, that younger Joshua that was about to launch the second company, not when you were a teenager because teenagers don’t really listen. Maybe when you were a bit more mature, what would be that one piece of business advice, knowing what you know now that you would give to your younger self before launching a business and why?

Joshua Motta: For me, my biggest regrets are always around not taking enough risks and not doing so earlier. Knowing what I know now, I would have told myself to do that. Setting up my own company, whether it was as a teenager or more recently, it’s been the most enriching life experience for me. It’s allowed me to learn new things, to grow as an individual, even outside of a business context, and it’s something I wish I had done much earlier. Particularly for those who are debating going down the path of investment banking or private equity or management consulting or any other wonderful career path for highly-skilled and smart people, I wish I had gotten out of that much sooner. So, that’s what I would have told the old Joshua who would skip that and go straight to building companies, and don’t fear it. Don’t fear the risk. Just persevere.

Alejandro: That’s it! Joshua, for the people that are listening, what is the best way for them to reach out and say hi?

Joshua Motta: I’m on Twitter: @joshuamotta. My email is jo****@co**********.com . I probably shouldn’t give out my mobile number, but if you want it, you can tweet me or email me.

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

Joshua Motta: I’m glad to be here. Thank you for having me.

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