Robert Sadow And Jonathan Sadow On Raising $100 Million To Reinvent How You Commute To Work

Robert Sadow and Jonathan Sadow are the cofounders of Scoop which brings commuters together in convenient carpools by partnering with their employers. The company has raised so far over $100 million from top tier investors including Activate Capital Partners, Index Ventures, G2VP, and Signia Venture Partners to name a few.

In this episode you will learn:

How they are using a carpooling marketplace to make life and business better
Their approach to raising over $100M in equity from great investors
Tips for tackling marketplace startups
The most important thing you can do as a founder

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About Robert Sadow:

Robert Sadow is co-Founder and CEO of Scoop, the largest carpooling solution in the United States, partnering with some of the world’s most forward-thinking organizations like LinkedIn, T-Mobile, and Workday to offer convenient, reliable, and safe carpooling to their workforces. Scoop addresses a key pain point for businesses and employees alike, solving for the third-largest driver of voluntary attrition: the commute.

Robert Sadow currently sits on the board of the Association of Commuter Transportation and has spoken on the topics of new and shared mobility in Fortune, Bloomberg, and at industry, academic, and investor conferences across the country.

Prior to co-founding Scoop, Robert Sadow was a strategy consultant at Bain & Company, where he specialized in customer strategy and marketing.

Robert Sadow graduated from the University of Pennsylvania’s Wharton School with a BSE in Management, Legal & Business Ethics.

About Jonathan Sadow:

Jonathan Sadow is co-founder and chief product officer of Scoop, the largest carpooling solution in the country. Scoop partners with some of the world’s most forward-thinking companies, including LinkedIn, T-Mobile, and Workday to offer convenient, enjoyable carpooling to their employees, helping commuters be happier and less stressed in their day-to-day lives.

With a rapidly-growing company headcount of more than 150 employees, Jonathan Sadow has scaled his product team at Scoop from original product wireframes to a team of 35+ engineering, product, design, and UX research professionals. Prior to co-founding Scoop, Jonathan Sadow spent years in product management and business development at Google and graduated from George Washington University in Washington, D.C. with a Bachelor of Business Administration in Finance and International Business.

Connect with Jonathan Sadow:

Connect with Robert Sadow:

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FULL TRANSCRIPTION OF THE INTERVIEW:

Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. Today we have two co-founders, two brothers, super-exciting stuff. They’re going to tell us about how to bring commuters together, and then also how to build and scale companies. So without further ado, I’d like to welcome our guests today, Jonathan Sadow and Robert Sadow. Welcome to the show.

Jonathan Sadow: Thanks so much, Alejandro.

Alejandro: Why don’t we start, guys, with Rob. You can tell us how live was growing up in Atlanta with the family there?

Robert Sadow: Life growing up in Atlanta was great. Jon and I grew up in the suburbs right outside of Atlanta. It’s actually the root of why we do this and were interested in the commute in the first place. Our first experience with commuting was high school. Our high school was 25 miles away from where we lived. We loved Atlanta but didn’t particularly love driving 250-300 miles a week back and forth to school.

Alejandro: Got it. Jon, how many siblings? Is it just the two of you, and who’s the oldest?

Jonathan Sadow: Just the two of us, and Rob is the older one. I think if there had been more children, our parents would not have known what to do with all of us.

Alejandro: I hear you. I hear that Rob went to Wharton. You went there for your undergrad. Is that right?

Robert Sadow: That’s right. I went to school at Wharton and studied business there. It was a funny experience for me. I lived on campus, three blocks from campus. Commuting went from number one on the list of things that I worried about to dead-last, but it was a great experience and great education.

Alejandro: One thing that I’ve seen, because I do guest lectures there. I’ve been doing that for seven years now with Professor Tyler Wry — is that the network is unbelievable. Why is this network so powerful?

Robert Sadow: It is a powerful network. It was incredibly helpful for us when we were starting the company. I think it’s a set of folks that are quite likeminded, and we believed a lot in supporting each other and giving back to the broader Wharton community. When Jon and I started Scoop, I reached out to a number of my friends from school who were in the investment community who had started companies and ended up being a fantastic resource for us as we thought about what it meant to get started.

Alejandro: And you also took the traditional route. I see a lot of folks going into consulting from there. How did you end up at Bain?

Robert Sadow: I think you’re right. It’s probably the second most common route coming out of Wharton. Number one being, working in finance or investment banking. I was interested in what it meant to help companies think through solving problems. It was something that was always interesting to be personally involved. Jon and I were involved in a youth group, even in high school, where a lot of the work that we did locally was helping this youth group understand how do we grow membership? How do we improve programming? In some ways, even those experiences growing up led me to feel like consulting was particularly interesting to do that and adds to the corporate at the Fortune 500 level. I moved to New York after school, worked at Bain doing consulting and a bunch of different industries. I particularly focused on financial services, retail, and telco companies.

Alejandro: There, you gained exposure to solving problems, breaking big problems into smaller problems, and tackling those smaller problems. But I believe you understood the power of adding value to customers and retaining customers. So would you mind expanding on that?

Robert Sadow: Sure. I think you’re right in that the most valuable thing that comes out of a consulting background is this idea of how do you break down problems? The fundamental unit of business in my mind is the approach to how do I take a problem, break it down into component questions, think about the work that we need to do to solve that, execute that work, and then be able to communicate to a group of folks what we should do as a result to move forward? All business is a compilation of those types of problems — the increasing complexity of being able to break it down in that way is super valuable, and I think that’s what consulting teaches you to do. The other thing it teaches you to do is move into a service mindset when it comes to customers. You think deeply about what does it mean to increase value, to partner well, to communicate effectively so that people with different types of experiences, different backgrounds, can understand your point of view, and you can quickly learn how you can support them? I think it’s incredibly valuable as an entrepreneur to come from that background because as you think about building new products or putting relationships with enterprises, a lot of what we do is try to understand their needs, break down those problems into actionable solutions that we can work through for product or a partnership perspective. It’s been invaluable for us at Scoop.

Alejandro: Got it. Then, in your case, Jon, you went at it with finance, but then you understood that was not your path, and tech was your passion. So how did this passion come knocking at your door?

Jonathan Sadow: I went to school in D.C., and similarly to Rob, was enticed by living in an urban environment, not having a car, being in one of the country’s greatest places to be, especially in your college years. I had always wanted to build things. I thought that would be real estate. So growing up, I loved the idea of building buildings, thinking about how to add value and create great things that make people’s lives better physically. Once I ended up at Google, I realized that actually in the world that we live in today, software gives you the opportunity to do that at a scale and degree that’s actually many, many times greater even than real estate. So I had that epiphany that I think a lot of folks do in this generation, which I studied financing and got to Google and said, “Oh, no. I should have studied computer science.” I quickly tried to catch up my skills there and make that an area that I wanted to pursue as a career got into product management, and the rest is history as far as Scoop goes.

Alejandro: How do you go to, let’s say, Google, and you start to transition from the business side to more like the product side? How did you manage to do that internally?

Jonathan Sadow: It’s a great question, and I’m very thankful about the fact that Google has a ton of resources and orientations toward helping people pursue new learning, new skills there. I called this person up — there’s a man at Google named Albert Twang who did the same thing and went through a transition of being on the people team into an engineering role. He built this internal course at Google, where he was teaching all kinds of people around the entire company how to write code. It was mostly people not coming from an engineering background, but he pioneered it, he built it, and he turned it into a course. When I found out about that in my first year at Google, I dove in headfirst and was able to take advantage of that, and did go from a sales world to a PD world where PD was a lot closer to product and on a startup team at Google that brought me into that part of the development area. And then, finally, over to product management. The last piece of that was good mentorship. I was lucky to join a team where [0:08:30] and Ed Blakely had both put the energy behind me to help me to learn more and get that opportunity. One of the fun stories there is both of them ended up becoming investors of Scoop when we started the company.

Alejandro: Obviously, from software development and then also product, etc., I’m sure that you learned a lot during your time at Google. Especially because you were there for almost five years. If you had to describe your three biggest takeaways from working at such an incredible company — it’s actually super hard to get into Google. What were your three biggest takeaways from working at Google?

Jonathan Sadow: The first thing, of course, that comes at you full-speed at Google is the scale — is really understanding how much impact software can have and technology can have at scale. I was working on a product where, by the time we were done over the course of about a year and a half, we had gone from one country of operations for our product to ten. So you just had this ability to bring things and bring value to users in different countries and different arenas with different needs. It’s a certain piece of skill that you get exposed to, or you get to learn from Google that helps you understand the power of that company and technology. The second is a much more specific part of management learning, which is, at Google, you have this platform of resources, and there’s so much that you can do, and you have such great talent that it makes it even more important to learn how to prioritize. So one of the best skills that I learned on my team at Google is the need for this ruthless pyritization around, we can build anything we want. We have all the talent in the world, but focusing that energy on what’s going to drive impact on people’s lives, or the users, or the customers that we’re trying to create for is key. Then the third part was something that I learned at Google, and I think you can probably learn at many other different companies as long as they have a vibrant culture. That was the importance of what it means to really understand and respect people across different capabilities and technical strengths. What I mean by that is, to build great product anywhere, but especially Google, there’s great engineering, there are great product managers, there’s marketing, there are design leaders, research leaders understanding how to get the best out of each person’s discipline and expertise, especially in a place like Google when you’re surrounded by such amazing talent is the lesson that I most took away from that environment, and we try to emulate back within Scoop. It’s building a culture that allows each person’s expertise to shine and turn into great product outcomes.

Alejandro: Very cool. Rob, you were mentioning earlier that you guys being in Atlanta, you got used to the commuting. So they say, “Ideas take time to incubate.” It’s not an overnight type of thing that all of the sudden, it sparks. It’s over time, maybe unconsciously, you’re developing that potential solution to that problem that you have been encountering, but I want to know what was that day, that conversation, that you and Jon had that sparked the acceleration of you guys being present to the fact that you could have something, and perhaps it would make sense to bring that to light? Tell us about that day.

Robert Sadow: First, it’s important to note that Jon was always more entrepreneurial of the two of us. I was the one that had to be pulled there a little bit more. Jon, I think, always knew that he wanted to start a company. I was very happy in my consulting lifestyle and work. It took me a little while to actually get to a place where I felt like it made sense to make this kind of investment and take the leap and start a company. To your point, it starts back with our experience growing up. When you grow up with a longer commute, and you’re spending 250-300 miles a week on the road, it impacts you in a lot of meaningful ways. The things that I remember in particular that I experienced and that Jon experienced were I remember being tired at the end of the day. It had a huge impact on my stress level, about was I going to be, where I was supposed to be on time. It influenced what activities I could, or I couldn’t participate in outside of school because I was spending so much time in that car. So I think that took hold for me and took hold for Jon early on. When I was in school at Penn or at Wharton, I didn’t think about the commute. I didn’t have to do it. I lived on campus or near campus. When I moved to New York, and I worked in consulting, as most consultants do, I fly out on Monday. I’m traveling for four days; I come back on Thursday evening. For me, I was particularly lucky. Most of my clients were local. I lived in New York City. I worked in the city. I could walk, or I could take the subway. I didn’t have a true commute experience at that point and time. I moved to the Bay Area about six years ago in late 2013. Candidly, the only reason I moved out to San Francisco is because Jon was living out there. I was in New York, and he was in San Francisco. The last time we lived in the same city, I was 18, and he was 15. We were in Atlanta, and I wanted to be closer to him. When I came out to San Francisco, it was this interesting experience where Jon had been commuting from San Francisco to Mountain View at Google. That was having a meaningful impact on his life, and we had talked about that quite a bit. My sister-in-law, Jon’s wife, was doing a Masters at San José State in the evenings. She was going at rush hour from San Francisco to San José to spend a couple of hours in class to go back. I was working at Bain in San Francisco, and a lot of our clients were tech companies that were based on the Peninsula in the South Bay. So consultants would drive back and forth quite often. What happened is, it was this reconnection with this experience that we had grown up with. We had this understanding of what it felt like to commute over distance, but we sat down and said, “Look. This is a problem that’s worth solving. If you can actually figure out a different way to help people get back and forth and not have to drive alone over longer distances, the quality of life improvement, you can unlock, the impact is meaningful. That’s what started us down the path was belief that this was a huge problem that needed solving. That’s when we started to tinker and think about different solutions and approaches for how you might be able to do that.

Alejandro: Got it. Jon, the next question I want to ask you here is — now, you’re the product guy, the entrepreneur mind-fit, and after those conversations with Rob, perhaps you started to think about what color that idea or that problem would have on the canvas. I’m sure that as you guys started brainstorming, things started to become a little bit clearer, it crystallized a moment that this is something that you wanted to go after, and very nice, stable jobs with nice paychecks that you got at Bain and Google. So how was that say that you decided, “Let’s do it”?

Jonathan Sadow: Much in the same way we run the business today, Rob and I have a pragmatic and methodical approach to the way we think about problem-solving. Even in the way you can hear Rob talk about how we thought about our own experiences and how we became reconnected with this problem that we had experienced in high school. It wasn’t a seminal moment. It wasn’t one thing that happened where we said, “Okay. This is real.” It was this well-structured plan where it started, if you think about it, from April 2014 to December of 2014. There was a moment in April right around when we were having all these conversations about the commute. We ran a survey asking people about their personal and professional frustrations. I remember we got the results for the survey. The only thing that was in the top five of both surveys was traffic. That was this spark that got us back to talking around, “Wait a second. We know that. We have felt that. We’ve seen that in our daily lives.” That kicked off where we started to think about, “Who are the stakeholders? What do the businesses feel about this? How does this affect companies, and why haven’t people been able to adapt their lifestyles to carpooling? Or, rather, why hasn’t carpooling been able to adapt people’s lifestyles? It was one step after another, where we had our first conversation with a prospective customer, and we had them lay out the case for why this was something they desperately needed for their employees. Then we started doing some survey work with that customer, and we started building the pilot app. We ran the pilot in the fall of 2014. Once we found the pilot that we did with our partner, that week, one to three to four, there was progressive usage. People were excited. People were feeling better, happier, and enjoying this. We had that moment where we said, “There’s enough here. We feel like we’re in the world today that can solve this problem once and for all.” That’s what gave us that final push to jump off the cliff so to speak, and go and dive into starting the company.

Alejandro: Very cool. Rob, was it the two of you guys giving the notice at the same time, or maybe one and then the other? How was that?

Robert Sadow: We gave notice at roughly the same time. Jon and I first started thinking about the specifics of Scoop and how we might approach it and do due diligence on the idea about nine months before we gave notice. So we did a lot of work and thinking beforehand to prepare ourselves. Then January 2015, we both left our jobs within a whole week of each other.

Alejandro: Then what happens next, Rob?

Robert Sadow: The first thing that we focused on from an approach perspective, and in some ways this ties back to my own experience at Bain was, what do we believe that we need to prove to say it makes sense to go out and focus our time in a dedicated way, raise capital, build a team, and try to solve this problem? What we spent the time in advance of leaving our jobs doing was trying to validate our understanding and how we thought about the opportunity. So a lot of work on what’s the size of the market? How do people experience their commute today? What are the alternatives? Why aren’t people using those alternatives? What’s the business model? By the time we left in January 2015, we felt like we had a strong perspective on the key questions that we needed to address in building a company. The first thing we did, even a few months before that was, we started to have conversations with prospective investors. Most of those conversations came from people that were in our network or friends of friends as we tried to get feedback and sharpen our point of view. By the time we left in January, we had built a number of those relationships and immediately went into conversations around capitalizing the business we started to build.

Alejandro: Got it. Then talking about putting the product together, Jon, I know that you guys had an interesting story early on with a pilot that you were putting together for Workday. What happened with those algorithms?

Jonathan Sadow: Yeah. This is one of those stories that I now tell and can smile and laugh through it, but for a while, we had a bit of PTSD to be able to tell that story. But this is the first really true, “Oh, my gosh moment” that happened for us. The night about the pilot I was referencing before was October 2014. I had been trying to hack together this algorithm for months, and that’s certainly not my expertise. So it was duck taped and glued, to say the least. We get to the first night, and we’re waiting to see if people are scheduling carpools, and are they interested? And all the sudden, the requests are coming in, and people are excited. The deadline for a matching happens, and I’m ready to run the algorithm, and it basically just dies on me. Nothing works at all. We’ve made no matches. So Rob and I are freaking out. We’re really nervous. The whole thing is going to blow up. Should we push it back? Should we cancel it? Maybe this isn’t going to happen. Actually, it was my wife who came to the rescue as she tended to do. She came in and said, “Guys, you need to settle down. Let’s figure this out.” I remember she grabbed a whiteboard marker. She goes to this whiteboard that we had in the room that we’re working in. She goes, “Let’s write everybody down.” We started using Google maps to look everybody’s addresses up and try to find ways to match them together in carpools. It was a really good lesson in what it means to have grit, resilience. Frankly, it was just one of a hundred ups and downs that we were going to have. It taught us a lot about what it would mean to build the product next spring after we had raised some money, and as we started to hire, and what it needed to look like for us to feel comfortable building an MVP now that we really were a company that was going to be able to thrive and be really successful.

Alejandro: Very cool. Well, hopefully, Jon, you invited your wife to a nice date night to say thank you for that. Rob, let me ask you here. What ended up being the business model. The consulting guy. Come on. Tell us what ended up being the business model?

Robert Sadow: Sure. The business model ended up being Scoop partners with companies. We predominantly focus on large employers. We also work with some smaller employers to bring Scoop to their employee base. What we realized quickly was there was a real need at the enterprise level beyond even the experience that employees were having on a daily basis. The few things that popped up were, number one, as real estate was getting more expensive, we saw a number of employers starting to put more people in per square foot in their space. As a result, higher density, no parking to support that level of density when those buildings were originally constructed. So employers were struggling to figure out how do they enable people to get back and forth to work if there isn’t enough parking using vehicle trips? The second was, employers were struggling with commute impact as commutes were getting longer, and areas were getting more congested. So recruiting, retention, and employee engagements were increasingly impacted by experience, and we could deliver a materially better experience than people had driving them. The third was around sustainability, and the importance of sustainability, and reducing carbon footprint. Scoop is a carpooling solution that can make it possible for people to share trips, and as a result, reduce their footprint. So the business model, as a result, became we sell Scoop as a solution to enterprises to improve quality of life for their employees. So employers pay us. That’s where our revenue comes from. By improving quality of life for employees, we can generate better returns on the real estate, giving capital to sustainability investments of our customers.

Alejandro: How did you go about fundraising?

Robert Sadow: We went about fundraising largely through network. The initial folks that we spoke with — you know, I had mentioned we started to have conversations a few months before we left our respected jobs. After we left in January 2015, we immediately put together presentation materials on how we thought about the market, the opportunity, how the business model would work. We put together a product demo based on some of the work that Jon had done in the pilot to understand how we had thought about what the core experience would be. We had a number of conversations over about a three or four-week period. One of the things we learned very quickly was — and this is true not just in seed fundraising, but I think throughout our fundraising is the way you orchestrate that process and making sure it happens on a contained timeline and everyone moves at the same time is really important. So we set a clear starting point to when we were fundraising, a clear ending point. We raised that round. It concluded in March of 2015, and we were able to shift focus toward recruiting and building.

Alejandro: How much capital have you guys raised to date?

Robert Sadow: We’ve raised a little over 100 million in capital.

Alejandro: Very nice. Obviously, great folks. I see Index, BMW, Workday. So thank God that they were not super upset with the pilot. So I see that they invested. That’s awesome. Jon, I want to ask you here. Marketplaces are a beast, and you got the supply, you got the demand, you got retention rates, which is what investors are going to be looking at, and that’s why you needed to do a good job to make sure that Rob was able to present this. What has been, from building a marketplace perspective, your biggest lesson to date?

Jonathan Sadow: For us, the biggest lesson is actually very specific to Scoop. We were fortunate that as Scoop was growing up, and over the last few years, we were in the wake of a lot of successful marketplaces and some unsuccessful marketplaces. So there are a lot of best practices and a lot of the metrics in the way we think about growth, the way we talk about authorization. We’ve learned a lot of that from watching others who were a step ahead of us in terms of their chronology. For Scoop, the most interesting lesson for us on the marketplace side is actually how much commuting is in an amalgam or an aggregation of really different marketplaces. I remember when we first started, one of our earliest routes — so much of what we do is about commute corridors. Each corridor is very different, whether you’re coming from a certain origin to a certain destination. Even the same destination can look very different if you’re coming from the East Bay down to the South Bay, or you’re coming from San Francisco down to the South Bay. We realized that you have to understand the marketing and each geography, and in fact, the supply constraints in a certain geography, they look different place to place. What I mean by that is, we have this route that when you’re going to work, it was actually against traffic, and the carpool way was on the way back. We found, “Hey, we expected to have a lot more riders than drivers.” But in that first piece of that first route, we had much more driver demand because they said, “I don’t have a lot of traffic. I can use the carpooling. So if I can earn or reimburse a couple of dollars on my way to work, that sounds like a great deal.” It was us having to understand how do we break down each individual market and understand both sides of the marketplace, the incentives, the pricing, the dynamics of matching, and realize that you can’t just do that one time and apply it to all the different markets. You have to understand the nuance on a geographic and on an employer basis.

Alejandro: So, in order to find that liquidity, Jon, did you guys — the problem here is that you want to make sure that when someone is going in, they find what they’re looking for in a short period of time. The problem is that if they pull out the service, and they don’t find anyone, then that’s problematic because that’s going to also affect the retention. So how did you go about building that liquidity?

Sadow: The key to the liquidity equation for us is how we think about partnering and becoming part of the experience for employers at a given customer. At the end of the day, if you look at the reason we commute, it is because we are all going to work at a certain company. And if you look at where companies are distributed, and you even think about zoning. Companies are concentrated. We build big office parks. We build big buildings, and we’re generally finding that people are going to these much more constrained geographic areas on the work side, but on the home side, they’re very spread out. So for liquidity purposes, the biggest push for us has always been about the business model. It’s always been about how do we marry the value that we’re giving to our customers with also their employees because it allows us to have this concentration on one side of the market. Then once you’re partnering and you’re going deep into that customer, how do you think about the different built-in dynamics that might drive toward driving or drive toward riding, and how do you understand those quarterly mechanics?

Alejandro: Got it. Rob, you had the consulting experience. You had worked with a lot of teams, so you had a very good understanding of the good, the bad, and the ugly when it came to culture. Then also about bringing on people. But I think that culture really starts with you guys, with the founders and how that’s engraining in the building blocks of that culture for the business. I understand, as well, that doing a business with a sibling, or with a family member, or with your husband or wife, is a real tough one. So how did you guys go about respecting each other and understanding how to embrace that communication between the two of you?

Robert Sadow: Well, 80% of the time, it’s great. I’d say about 20% of the time, it’s taken a lot of iteration for us to understand our respective roles and how do we work together, and frankly, it’s changed a lot from the first days to where we are today. Maybe to take a step back, Jon talked a little bit about his experience at Google, from a people perspective. If you think about consulting and Bain and my background, at the end of the day at a consulting firm, your biggest product offering is actually your people. It’s the team that you put together to partner with a customer, how you build those relationships to deliver value. That’s what creates a lot of differentiation for a Bain versus a McKinsey, for example. So, as a result, those companies are built understanding that the only way to succeed long-term is to be able to attract and retain fantastic talent, and there’s a tremendous amount of investment there. When Jon and I started Scoop, immediately, I took that experience and Jon took his experience and said, “We’re going to build in an organization where we understand that our people are our greatest asset.” Every time we’ve interviewed and I’ve told candidates this and team members since the beginning, every time we hire someone, it’s fantastic. I think about it as a meaningful win in the direction of what we’re trying to accomplish for the company. So that became the foundation of how we thought about building culture and building people was being very people-centric and understanding that ultimately if Scoop is a success or failure is largely going to be driven by the team that we’re able to put together. In terms of Jon and I working together, specifically, one of the things that’s different about startups and building companies than what people read in the press is what that experience actually feels like day-to-day. If you look at the news or you read TechCrunch, for example, you might see, “Company raises seed financing; raises A; raises B; raises C; sells for a big sum of money.” You look at it, and you say, “Okay, why doesn’t everybody do that. That seems like the greatest business model or way to be successful ever. But in reality, you have great days, and you have terrible days; you have quarters that go very well, and you have quarters that are really challenging. At the end of the day, what makes it worthwhile to build a company is, 1) deep belief that what you’re doing is important. That solving this problem, the impact on the world matters. 2) The people you do it with are the people you want to go spend that time with. You want to be working hard because you share that passion and belief in what you’re trying to accomplish. For Jon and I as co-founders, Jon, I trust implicitly. I know at the end of the day he’ll always have my back; I’ll always have his, that we care about this both deeply, and together we know that we can be successful. Having that trust in a co-founder to use the foundation and build team around, for us has been incredibly valuable, and it’s something that I think adds a lot of strength to the company over time.

Alejandro: Yeah, absolutely. Jon, and feel free to expand on that.

Jonathan Sadow: Rob captured a lot of it in a great way. I think that we were lucky that one of our first investors, over at Signia, who has now gone and started his own venture really, really pushed us to invest our energy and culture and having a point of view on the culture and the type of team we wanted to build in the beginning. I remember, and I don’t think I’ve admitted this to him before, but I remember in May of 2015, we had five people in the company, and we hadn’t even built our product yet. He was like, you guys need to start thinking about your culture and your values, and what it means to get your team in a room and say, “Who do we want to be?” I remember thinking, “Wow. It’s so early. Why do we need to invest in culture? There are five of us.” We were just trying to figure this out, but it was foundational. It was foundational for us to realize that prioritizing the company that we are building, how we want to operate, who we want to be, what’s going to motivate us is, in many ways, the most important thing to do as a founder. Because what you’re betting on is that you can find great people who can take on each challenge, can learn as fast as you can, can push the company, and the vision that you have for it. We’ve been lucky that we’ve had that as part of our DNA from the beginning. And, as Rob said, understood that investing in great people is investing in the outcome of the business. Those are harmonious. It’s not a means to an end. It really is the end in a certain way to build a great team and a great culture.

Alejandro: For sure. It’s all about people. It’s all about people. So, Rob, for the folks that are listening, perhaps for them to get a sense of how big you guys are, and maybe there’s something you can share in terms of employees or any other metrics that you think could be interesting to hear.

Robert Sadow: Scoop is about a little over four years old now. We launched for the first time in August 2015. We’re about 150 team members now, mostly in San Francisco, but also distributed in other markets that we’re investing in to grow Scoop. I’m proud of the impact that we’ve had. Since our launch, our community has taken more than 8 million carpool trips. We’re proud of the set of employers and customers being able to work with to make that happen. I think that gives you a little bit of a sense of the scale and the team sizing.

Alejandro: Got it. This next question will be for the two of you. This is typically a question that I ask the guests that come on the show. Now, looking back and knowing what you guys know now because it’s been an incredible journey for the two of you and also for the team. If you had the opportunity to go back in time and speak to your younger selves, to that younger Rob that was in Bain, or to that younger Jon that was in Google, and right before the moment you were to give your notice and launch your own business, what would be that piece of business advice that you would give to your younger self before launching a business and why? Let’s start with you, Jon, and then Rob, feel free to jump in as well.

Jonathan Sadow: It’s an excellent question. We’ve had this asked in different formats, but it’s a really thoughtful way of positioning it. I have a feeling my answer might be similar to Rob’s. So, Rob, I’m sorry if I’m going to steal yours, but the biggest thing I wish I could tell myself before we launched is to understand just how up and down the experience of starting a company really is. It’s been interesting for me where this has crystallized for me as a founder is actually — since we started Scoop, I’ve also become a parent, so I’m a father of two. One of the things my wife and I talk about a lot is that — and we tell our friends that are just having kids, is that nothing lasts too long, whether it’s good or bad. What I mean by that is, when you have kids there are weeks when kids are going through changes and growth, and you’re wondering when it’s going to end, and then there are weeks when your kids are awesome and easy and listening, and you say, “Oh, this is great.” And then before you know it, it’s gone. You have to learn to love all those pieces of it and understand that nothing really lasts that long. Building a company is very similar. There are great highs, and there are really significant lows, and you have to understand that the emotional up and down will get the best of you if you don’t see the forest for the trees. Honestly, a lot of that has to do with the conversation we just had about culture and team and understanding that over time, your north star becomes about the people you’re working with and the vision that you’re trying to accomplish. Nothing great last that long before the next challenge, and no challenge lasts so long before the next great win. Having that perspective, going into would have been great, and I would hesitate, I guess, that it’s one of the reasons why second and third-time founders have so much success disproportionally. It’s because they’ve understood what the amplitude of the emotional curve looks like. It’s a really big advantage once you’ve settled into that as a founder and for me as a parent.

Alejandro: Yeah. Makes total sense. And Rob, what about for you?

Robert Sadow: For me, the biggest learning and what I would tell myself if I went back is, the perceived risk in stepping away from a larger and more stable type of job or employment and going to a startup is nowhere near as big when you’re on the other side of it. I remember that year where Jon and I were talking about doing something in an entrepreneurial perspective and building Scoop before we left our jobs. I agonized over that, candidly. It was really difficult for me because I was doing really well in my job and my career, and what if it doesn’t go well, and what if we can’t accomplish what we want to? How does that impact my career, my wife, my financial situation? When you’re sitting from the vantage point of that level of security financially employment-wise, it can be really daunting. But, frankly, as soon as we jumped over to the other side, and we were building Scoop, and you’re in it, and you feel the energy that creates and the rush from building a team and hiring and getting to work with great people. And when you start to hear feedback from commuters on how Scoop changes their life on a daily basis, and the relationships that they’ve built, and what your energy and timed investment has created for them, it totally changes your perspective, and you recognize quickly what the impact is, and why you take risks, and why others have taken risk for you. So if I were to go back, I’d say, “Look. It’s never as daunting, it’s never as challenging on the other side as you thought it was going to be before you dove in.” And I hope others that are thinking about that, who may be saying, “I’ve got something I’m passionate about, but I’m nervous what that does to my life,” that they go ahead and lean into that because that’s where a lot of great innovation in the world and solutions to problems we face come from.

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

Robert Sadow: You can reach us if you’re interested to learn more about Scoop or the company you can find more information on our website at www.takescoop.com. You can also email us at in**@ta*******.com if you’d like to follow up.

Alejandro: Fantastic and any social media activity?

Jonathan Sadow: You can follow us at Twitter @takescoop. That’s the way to keep track of what the company’s up to.

Alejandro: All right. Fantastic. Well, now that Thanksgiving is coming up, hopefully, you guys can leave Scoop a little bit for a dinner while eating a turkey. In any case, it has been an honor, guys, to have you on the show. Thank you so, so much.

Jonathan Sadow: Thanks, Alejandro.

Robert Sadow: Thanks for having us.

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