Gautam Tambay is the Co-Founder & CEO at Springboard, a company that has been successful in breaking the 500-year-old education system with a new way to empower workers for the new economy. Their mission is to help a million people to find a more efficient and relevant way to learn and gain modern employment in the new world of work. The company has raised $53M from top-tier investors like Learn Capital, Costanoa Ventures, Telstra Ventures, and Blue Fog Capital.

In this episode you will learn:

• The surprising advantages of being totally transparent with your team
• Hiring on values and building your startup culture
• The evolving fundraising process
• When you should turn down investors
• His top advice for other aspiring entrepreneurs

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About Gautam Tambay

Gautam is CEO & co-founder of Springboard, a rapidly-growing workforce development company focused on digital economy skills like AI & Machine Learning, Data Science, CyberSecurity, and UX Design. Springboard has trained over 200K professionals, helping digital economy aspirants get job-ready with 1:1 mentorship from industry experts. The company also collaborates with Fortune 500 companies and startups as a training and talent partner.

Gautam spent the first decade of his career working on technology, data, and strategy at InMobi, Bain & Company, and Capital One. He holds an MBA from the Wharton School, and studied engineering at IIT Delhi.

Connect with Gautam Tambay

• LinkedIn
• Crunchbase
• Twitter

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FULL TRANSCRIPTION OF THE INTERVIEW:

Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. Today we’re really going to enjoy the guest that we have joining us on the show. We’re going to be learning about culture; we’re going to be learning about how the culture may or may not be impacted when you have different offices, and then also building and scaling. So without further ado, Gautam Tambay, welcome to the show today.

Gautam Tambay: Alejandro, thank you for having me. I’m so excited.

Alejandro: So originally born in India. You jumped from place to place quite a bit because your father was in the army, but tell us about your life growing up there.

Gautam Tambay: Yeah, thanks for asking. My dad was in the army like you said. That meant that we moved to a new city every three years. At the time, I didn’t realize how much of a boom that was going to be for me over the course of my career. What it gave me is the ability to be dropped into any new context and quickly understand what’s going on, quickly make new friends, and really adapt. That served me really well. I wouldn’t trade that upbringing for anything else.

Alejandro: Entrepreneurship and being an entrepreneur, there’s a lot there of dealing with uncertainty, but since you were moving quite a bit, and you had to make new friends every three years, I’m sure that shaped you up a little bit for being able to deal with uncertainty and uncertain moments.

Gautam Tambay: For sure. I think both uncertainly and change, which are so core to being an entrepreneur and so much about the journey. I learned to deal with those very early. The funny thing is, I don’t think I realized that I was learning that skill because when we were growing up, that was just life – every three years, you moved. There was no alternative. When you’re six years old, that’s the only life you’ve known. Only in hindsight have I been able to connect the dots and say, “That was actually something that gave me these life skills that let me adapt to new circumstances, make connections more easily, which is very valuable, and fundraising, and when hiring, and get to understand different kinds of people and understand different perspectives because we moved to different parts of the country. Culturally, India is one country, but it’s like Europe in that the north is as different from the south as Norway is from Italy. So, that helped me be able to understand different people’s contexts and motivations more easily and faster.

Alejandro: It’s interesting, too, because then you went and studied mechanical engineering. But one of the things I want to ask you is that most of the entrepreneurs that are from India originally, they all have the engineering background. Why is this? It’s unbelievable.

Gautam Tambay: You know, that’s funny you ask that. This has changed, but when I was growing up, if you were good at school, then there were two things you could do. You could either become an engineer, or you could become a doctor. If you wanted to do the crazy, risky things, you became a lawyer. That’s just the India I grew up in. It’s changed quite a bit since. Even my sister, who is seven years younger and a designer, and that’s not a profession that was even in the realm of possibility that was offered to me. So I think exposure really matters, and I think that’s all we were exposed to. It’s almost a given that if you’re academically doing well, then you end up in engineering or in medical school.

Alejandro: Let’s talk about you ending up in D.C. How do you land in D.C. all the way from India?

Gautam Tambay: Yeah, that’s a great question. One of the great things about engineering school was, I think a couple of years into it, I realized two things: 1) I didn’t actually want to be a mechanical engineer. I wasn’t very good at it, but I really liked the way of thinking that engineering taught me, like a structured way to bring down any problem. That’s what I got attracted to. Over time, I ended up doing more applied math kind of work in my engineering program. There’s a company called Capital One based in D.C, which, at the time, would hire a couple of people every year from the engineering school that I went to in Delhi, and they would bring them to Washington, D.C. to work on what I think of as applied math problems, which, at the time, was data analytics and data science. I got recruited into one of those roles on campus, which ended up then changing the trajectory of my career in terms of being exposed to the U.S. and learning a lot.

Alejandro: So, how was that experience of coming here? Was it like a culture shock?

Gautam Tambay: Yeah. It certainly was. I had spent some time before and had done a couple of internships, one in France and one in Norway. Those had been my first exposures to living outside of India. I think coming to D.C. was definitely a culture shock. I remember; I think it was my first week in D.C. walking into a bookstore, Barnes & Noble, in 2003. I think President Bush was in the White House. I remember walking into a store, and the first thing I saw was – you know that table where there are a lot of display books. There were three or four books that were jokes about George W. Bush. I’m like less than a mile from the White House, and that was mind-blowing for me to say, “Wow! Freedom of speech really is quite something.” India is relatively good at freedom of speech, but even there, I couldn’t imagine that you would be a mile from the president or the prime minister’s office and actually see books that were making fun of the prime minister.

Alejandro: Absolutely. In Spain, for example, if you talk bad about the king, back in the day, you would be put into jail. I can see what you mean with that. So here in Capital One, you lasted for a few years before you got into Bain. I know that Bain was a big breakthrough for you and the way that you perhaps broke big problems into small problems to tackle them and make something happen. Tell us about landing in Bain and then going back to India to open Bain there.

Gautam Tambay: Joining Bain was actually a pretty interesting journey for me because, at the time, Bain only hired you straight out of college or straight out of business school. There was no you worked for a couple of years, and then you enter Bain. That wasn’t a thing. So what I did was, the closest school in D.C. – actually, I lived in Richmond, Virginia at the time. The closest school to Richmond, Virginia, that Bain hired at was UVA, the University of Virginia in Charlottesville, and that was about a two-hour drive from where I was. I saw online that they have an employer information center for people who go to UVA, and I hopped in the car and drove out. I put on my best clothes, and I said, “I’ll just show up there and see what happens.” I tended the talk, even though I wasn’t a student at UVA, and at the end of it went up to the partner who gave the presentation, and I said, “I don’t go to school here, but I’m really interested. I think I have some great experience, and I would love to apply.” He said, “Sure. Email me.” Which I did, and I had no expectations of getting a response. It turns out that something about what I said to him on my resume spoke to him, and he actually ended up giving me an interview, which was great, not just from the fact that it helped me break into this new role or opportunity, but also it was great validation of the fact that you miss 100% of the shots that you don’t take. If I had just sat there and said, “Bain doesn’t hire from anywhere outside of college, and not taken that shot, I would never have gotten it. I ended up being the first person, at least from Boston, that they had hired not directly out of college for that undergraduate program.

Alejandro: This, for you, was an interesting journey with Bain. There are so many people coming out of McKenzie or Bain. Why do you think consultants make such great entrepreneurs?

Gautam Tambay: Yeah. That’s a good question. I’ve wondered about that. Is it that it’s the training that you get in consulting that makes you a better entrepreneur, or do people who are well-suited to be entrepreneurs seek out those consulting jobs early in their career? I’m not sure whether there’s causation or correlation. But I do think that there are things I learned in my two-and-a-half years at Bain that have stayed with me throughout my career. As you were saying, taking any problem, breaking that down into its components, being able to hone in on what is most important in any given situation. That’s something that consulting trains you well to do. That was really valuable.

Alejandro: After this experience with Bain, then you go to business school; you go to Wharton, and, obviously, great entrepreneurs, as well, coming from Wharton. But this was a really nice segue to moving to San Francisco. There, that was your first exposure to the startup world. I’m sure that was quite eye-opening, as well, for you.

Gautam Tambay: Yeah, absolutely. When I was in business school – and it is sort of funny. I thought I was going to go to business school to learn entrepreneurship and actually become an entrepreneur. I now routinely advise people that if what they really want to do is something entrepreneurial, then they should skip grad school because they frame the problem as they have two years and $150,000 to invest in your entrepreneurial career. Is business school your best investment? Nobody framed it like that to me. In hindsight, again, I feel very fortunate for having had the learnings and the friends that I made at business school, but I think there was no better training for entrepreneurship than just joining a startup. So coming out of my business school class in 2010, it was the unusual thing to do. I had done my internship in private equity. Most of my classmates were going to Wall Street or consulting jobs. So they thought I was a little crazy to come join a no-name startup in San Francisco. There were only a handful of people in my class who did something like that. I think coming to Silicon Valley just completely changed my perspective on entrepreneurship and gave me a lot that I have now used in my career.
Alejandro: Here, while you were in InMobi, the mobile advertising company, it literally went from 80 people to hundreds. This was an opportunity for you to really see a company growing so quickly, but then, as well, to see what goes well and what goes poorly. What were some of the lessons that you took away from the experience here?

Gautam Tambay: I think a couple of things that I learned from the founder, Naveen Tewari, and CEO of InMobi that did he did really well – first, I had applied to a business development job at this mobile advertising startup coming out of business school. I had never worked at a tech company, and I had never worked in business development, and I had never worked for a startup. Naveen had the foresight to say, “I’m going to take a bet on this person.” He didn’t have to. He could have found more traditional candidates for the role, but I think that was really empowering for me. Then, it goes further than that. I think Naveen was the master of and still is in hiring great people, and then empowering them, and letting go. An example of this was about nine months into my time at InMobi; we had an opportunity to acquire this company, which was super interesting and could be very strategic for us. I think the whole company at the time was maybe 150 people. Naveen said, “Why don’t you come along with me to this company. We have this conversation with the founder of this company to be acquired.” It turns out they’re also being wooed by Google and by Apple to be acquired by them.

Alejandro: Wow!

Gautam Tambay: This is at a time when InMobi had raised maybe a total of like 20 million dollars, and we didn’t have a lot of money in the bank. We walked out of that meeting. The meeting had started at 6:00 pm. We left the company’s offices at around 11:00 pm, and then Naveen and I went to a coffee shop in San Francisco, and literally on the back of a napkin, and says, “Gautam, you’re going to run this deal and make this happen.” I’m like, “Are you kidding me, Naveen? I have never run an acquisition; I have never done anything of this sort. This is critical to the company. You’re going up against Google and Apple. Do you really want me to do this?” Then Naveen said something that’s always stuck with me. He said, “Listen. I’ve never done an acquisition either, so one of us is going to have to learn it and spend 50, 60, 70 hours a week getting up-to-speed and making this happen – better you than me because then it lets me focus on other things.” First of all, it was mind-blowing that that’s how he thought. Then, in hindsight, two things: one was so empowering for me. I’ve never worked harder. That was the next eight weeks. This was my life. It was a big, big opportunity, so I was like, “I’m not going to let him down.” The second thing was like Naveen said, it actually enabled him and empowered him to do other things. The story ends well. We won that deal with an all-startup acquisition against Google’s and Apple’s cash offers. Then the startup acquisition ended up being definitive to InMobi’s journey. So, hire great people, and empower them, and let them run with big things, and step away, and have the courage to do that as a founder. That’s something Naveen did really well. In terms of things that could have been better, I think that as they went through that hypergrowth phase in raising 200 million dollars and expanding the team from 100 to 800, I think a lot of things broke down in corporate communication, alignment, culture, which over time, we had to go back and fix that, but I think there were things we could have done better from the beginning in setting those things up for success. That’s something now that we take very seriously at Springboard as we are going through that phase of hypergrowth.

Alejandro: So, let’s talk about that. What made you make the switch and say, “I’m going to do it myself and take the leap of faith, and I’m going to make it happen on my own.”?

Gautam Tambay: Yeah. I loved how much I was learning at InMobi – hypergrowth, really good people to work with. One thing that I didn’t care much about personally was the industry we were in. Mobile advertising didn’t get me out of bed. So I was like, “If I’m going to leave and do something of my own,” which is an itch that I had always had – in fact, I was very open about that with the InMobi founders when I joined them is that I have this itch to do something on my own. I was like, “If I’m going to do something, then it has to be something I care deeply about to be able to wake up and do this for the next ten years or more even if all the chips are down.” I was like, “What problems do I care deeply about.” I had grown up in a family of educators. Three of my grandparents were teachers. Both of my parents have been teachers. My mother was a school teacher, and my dad is a retired army officer, but he now teaches at the University. So, education runs in the family. Then around that time, I saw my sister. She was an illustrator. She applied to go to grad school to learn UX design, and then decided that she couldn’t bring herself to pay a $100,000 loan, and decided not to go to the schools that she got into. That was similar for me in realizing like, “Wow! There’s got to be a better way in this day and age to help people get the skills they want to get to the careers they want. That’s what got me into the education space. I met my co-founder along the way, and she had a very different motivation but strong reasons to want to do something in education. We had lots of common friends and started working on some ideas together. That’s how we got started.

Alejandro: Tell us about the early days. What were some of the early days like?

Gautam Tambay: Tough. I think the first couple of years, and I’d say until we had product/market fit, were challenging. There’s this phase in a startup’s journey, which is existential, where you don’t know if you’re doing something that’s going to have value. You’re spending a lot of time and energy in this, and everything is, at the time, unclear. That’s also when people are questioning you the most. My father-in-law who is a man I really love, and I know he cares about me. He would ask me, “When are you going to get a real job?” He’s doing it out of caring, but that’s not how it sounded to me at the time. I think that’s when people are questioning you, and I think that existential phase was tough. I think the thing that helped is just having a group of people around me: my co-founder and our early team members who were just having a good time together. I think there are going to be ups and downs, but there’s this small group of people who are just going to battle with every day, and as long as you’re enjoying it, and enjoying every day, that is, at least for me, what helped carry me.

Alejandro: Absolutely. What ended up being the business model for Springboard for the people that are listening to get it?

Gautam Tambay: Yeah. That’s a great question. Today, we enable people to transition careers through intensive online programs into what we call new economy careers. For example, if you want to become a data scientist, you want to become a designer; if you want to become a software engineer, if you can take a Springboard program, that’s going to be nine-months long. It’s completely online. It’s very intensive, and every single student gets paired with a mentor from the industry who works with them one-on-one every week on a video call. What we do that’s unique is we say, “At the end of the program, we guarantee that you will get a new job in the field that you’re looking for, or we’ll refund you entire tuition. We’ve had thousands of people come through our programs. We’ve had to issue less than a couple of dozen job-guaranteed students.

Alejandro: Very cool. I know that for you and for your co-founder, there was an event that certainly saved the company, and it was that moment where your team members pulled you out and said, “Hey, guys. This is what we’re seeing.” And that was a big breakpoint for you guys, so tell us about this.

Gautam Tambay: Yeah. Thank you for asking that. This is 2016. The team was about 15 people at the time. I think maybe 16, and we had not raised a lot of money. I think we had raised a small angel round; maybe we had raised a million to a million-and-a-half dollars to date. We hit a point where revenue was declining, and at the same time, we had three or four months of runway remaining. That’s one of the hardest things that you can have is you see that you’re going to basically – for my co-founder and me, it was like this was our dream, and we could see it in front of us going to nothing, and we’d be letting down everyone. We’d be letting down our investors, our customers, our team, and that was a really scary moment. Our instinct, at that time, at least mine, was to go into a shell, like pull the blanket or covers over you and not come out. The last thing I wanted to do. So my co-founder and I were extremely stressed about this. Obviously, this was eating us up because when your revenue is declining and you’re running out of money, that’s the worst time to try and raise outside capital. One evening or afternoon, three of our early team members, Monique, Phil, and Roger, said to my cofounder and me, “We want to take you out for dinner.” We said, “Okay. Sure.” They took us out for dinner, and they said, “Guys, what’s going on? The numbers aren’t looking good?” We said, “Yeah, we know that.” They said, “Well, so why are you not stressed about it?” We said, “We are really stressed, and we’re not sleeping.” They’re like, “Okay. Why are you not involving us? How much runway do we have?” At that point, they asked me point-blank, and I’m not going to lie. I said, “Three or four months.” They’re like, “Well, why are you not involving us? What have you done so far?” We said, “Well if we thought that if we told you all of this, you would leave, and that would make things worse.” At that point, they said something, which has always stayed with me. They said, “If that’s what we wanted to do, we would have joined Google. We didn’t join this company to leave when things are bad. We joined because we want to be part of a story and build something. That’s why we are here, so you have to involve us.” It’s like I can remember this moment very visually where I was sitting during this conversation because it really has been one of the biggest leadership lessons in my career is that if you hire the right people, which thankfully, we had, then when you have a problem, and you have bad news, you wanted to [23:56]. My job as a leader was to be a **** umbrella, to protect everybody from bad things, and what I realized is, if I didn’t do that, and I let the bad news flow, I’m going to have 16 people working on the problem instead of two people. So, the next day, we talked to the whole company; we were very transparent and said, “This is what’s going on. We need to turn this around. We had a plan here, which was every single person, no matter what your job, you can be an engineer or you can be a customer support person. Everyone is going to work on a revenue project.” We had a plan to get us to break even in five months. When [24:35] and I said, “We’re going to go to every investor who in the past we’ve said no to, or they’ve said no to us, and we’re going to say, “Get any amount of capital that we can to extend the runway a little bit. Of course, we’re here to still tell the story, so, obviously, you know the story ended well. In four months, we got to break even, and we were able to raise a million-and-a-half dollars, which was a lot for us at the time. We went from a background of our money to the scale where we would break even and even have money in the bank. I was just the engineer, and the company wouldn’t even exist today if we hadn’t had that come-to-Jesus moment with our team saying, “You need to involve us.”

Alejandro: That’s amazing. For an operation like this, you’ve raised a little bit of money. How much capital have you guys raised to date?

Gautam Tambay: We’ve raised 53 million dollars to date.

Alejandro: I believe that during one of those fundraising rodeos is the very first time when you and your co-founder had the voice raised against one another. So, what happened there?

Gautam Tambay: Yeah. I just told you the story of when we turned things around, and the reason we were in that place of not having capital and possibly running out of money was because six months before that, we had tried to raise a Series A round. It was a grueling process. One of the things about fundraising is, you get good at one type of fundraising, and then the goalpost changes. After a couple of years, I got good at raising seed rounds. The Series A process is a totally different process. We had gone through this extensive six-week process, and I was the one doing most of the fundraising conversations. At the end of that six-week process, which was grueling, we had one term sheet. It was a top-tier Silicon Valley investor, somebody who everybody knows, and the catch was, it was what was called crushed deal, which means that wanted to give us half the money immediately, and they wanted to have the option to give us the other half of the money a year from then but completely at their option but at the same valuation, which is basically like wanting to have your cake and eat it too. Everyone we talked to, every advisor said, “Don’t take the deal. This is not entrepreneur-friendly. This is bad-fair business – the signaling risk.” Basically, if things are going well, they’re putting the same amount of money, the second crunch at the same valuation, which is not good for you. Things are not going well. They were not putting the second crunch, which sends a really bad signal to anyone else. Common sense, as well as all advice, said that this was not a good idea. But I, at the time, was like, “This is the only deal with have, and I have worked so hard for six weeks to get this that I think we should take it.” My co-founder was steadfast, and, of course, the good thing was that she had distance. I was emotionally embroiled because I was the one fundraising, and I was the one facing rejection. She had the distance to say, “You know? I don’t think we should do this. We should walk away from it, or we should hold a hard line, push back, and tell them what we want, and if they don’t give it to us, we walk away. I remember a conversation in her living room where we were having this argument, and I hadn’t slept much the night before. Virtually, we were close to screaming at each other. Thankfully, I listened to her, and that was the right thing to do that we walked away from it. But in the moment, it was one of the hardest things I’ve done. And, of course, six months later, we ended up faced with possibly running out of money, which made it even harder. But now that I have five years of hindsight from it, and so it was totally the right thing to do.

Alejandro: In this case, this is very interesting that you point this out because typically, the best deals are accomplished when you are completely unattached to the outcome.

Gautam Tambay: Totally. I think that’s such a great point. I think that you want to be dispassionate, and I think in the moment, I was tired, I was emotional, I was exhausted. One of the many, many great things about working with a co-founder, and especially for me having worked with my co-founder is, when one of you is in the thick of something, the other person has the ability to be dispassionate and to have distance. In those moments, listening to the other person is what helps you – this person has the exact same incentives as you but has more distance from the situation, so listening to the other person almost always is what leads to the better outcome.

Alejandro: That’s a very good point. There’s one thing here that you had to encounter, which everyone that is listening right now to this episode is also going to encounter or has encountered in their own journey of building and scaling, and that is, unfortunately, letting a person go. This case, for you, was an executive, so how was that experience for you?

Gautam Tambay: Yeah. Thanks for asking. One of the things I’ve learned is by the time you realize that somebody on your team is not performing or is not able to do what is most important for the organization, odds are that everybody else already knows and has already figured it out, and often, you realize that the last. Usually, their peers and their director are the ones to first figure it out. So, I had this thing of like, “Wow. I have this person on my team. I don’t think they are quite the right fit. Not because they’re not competent. In fact, the very fact that we hired them meant they were very, very competent, but they were not the right fit for this job at this time. One of the fears you have is like, “What is it going to do to team morale? Odds are that if you’re having that conversation in your head, the emotional response of the team when you actually make that decision is likely going to be relief because they’ve already figured this out. Often, the emotional response for the person also – there will be some anger and some denial, but eventually, when they go home and think about it, it’s also often relief because they know, also, that they’re not the right fit for the job. But doing it for the first time, especially with a senior person, for me, was not easy because it felt like I was letting them down, partly because especially when in an executive role, when somebody fails, it’s as least as much on me for either having made the wrong hire or not onboarding somebody successfully. I think part of it was me coming to terms with the fact that I had failed in hiding and onboarding the right person.

Alejandro: Yeah, and one of the things, too, that happens when you’re at this point, and maybe it has happened to you. At least, it happened to me is that you tried to reorganize things. You tried to put that employee on another role, and it becomes a toxic type of environment that you’re creating.

Gautam Tambay: Totally, and thankfully, I was very fortunate to have good advice. While I was like, “Maybe we can move the person to an advisory role,” I had good advice. I have a board member who’s been an entrepreneur twice, and he’s great at giving tactical advice. I had a couple of other advisors and other CEOs that I could call and talk through this. Thankfully, we took the clean way out, and that really helped. It is the kind thing to do to relieve them and let them find what is great for them and what they’re going to be great at. It doesn’t feel like that in the moment, but you’re actually doing the right thing.

Alejandro: Absolutely.

Gautam Tambay: For what it’s worth, this person is thriving in their other role. It’s not surprising. I think they’re super competent and a really accomplished person, just not the right fit for the job. One of the lessons for me was, which I think Ben Horowitz talks a lot about in his writing, is especially when hiring executives, don’t hire in a single casting. You want to hire the sales leader who is right for your company at your stage, not this incredible sales leader who built the sales function at Facebook. That’s probably not the right person for you. One of the things we’ve done since then is every time we open a new exec rec, we’re just hiring a CFO, so I did this last night, is we rank order all the – we make a list of all the possible skillsets you might want, all the experiences you might want in a person, and as a group, the candidates, which four or five of these are a must-haves for the next 18 months. Then, everything else is not important. When you go through that exercise, it’s very clarifying. If I had done that exercise when I hired the executive a few years ago, I don’t think we would have hired that person.

Alejandro: That’s interesting. I also know that part of hiring, too, for you that values are very important. How do you think about values when you’re hiring people?

Gautam Tambay: That’s a great question. One of the things early on that people would say is, “Is somebody a culture fit?” Over time, I realized that what culture boils down to, it’s not about ping pong tables; it’s not about happy hours. We do all those things, but it really boils down to what behaviors as a group are we going to reward and incentivize, and what behaviors will we not stand for and penalize? That’s ultimately what becomes your culture is what you do. If you think about what behaviors you reward and what behaviors you don’t stand for, that’s basically your values. Culture is synonymous with value. Now, when hiring, somebody says – it doesn’t happen anymore because we’ve institutionalized the company, but earlier on, when people would say, “I think this is not a culture fit.” The question I would ask them during the interview debrief would be, “Which of our seven values is this person not aligned with?” Because otherwise, you’re just saying that this person doesn’t look like me, or I don’t relate to them because my life experience is different than theirs. Let’s talk about are there values in this? I think one of the ways we realized that early-on was when we were a small team – I think we were 20 people or so, we had a team in San Francisco and a team in Bangalore from the get-go. From day one, we had two offices, and we would bring these teams together for an offsite in some other part of the world. I remember this was in Thailand. Going into this offsite, I remember being very stressed because there were eight or nine people in that staff, and there are eight or nine people in Bangalore, and we’re going to get to this offsite, and then the Bangalore engineers are going to be totally differently culturally from the SF business product and ops teams, and we’re going to have to force people to interact, and it’s going to be really awkward. Our offsite began on Sunday. I got there Monday morning because I was coming from a wedding, and what was mind-blowing for me was that people had chosen – at the time, the company was small, so we got an Airbnb, and there were no assigned rooms. People had chosen to room with each other across offices. By the time lunch came around, people were breaking into small groups, just organically, that were mixed groups. We didn’t have to do anything to force them to interact. That was surprising to me. But then, my co-founder and I were talking about this, and we were like, “Wow! This is great. Why is this happening? We must have done something right.” In that moment, we realized – this was before we had formalized our values or institutionalized any of the things that we have in the company today. We realized what was happening was, we were hiring for the same set of values, so even though you would expect that somebody who is an engineer in Bangalore would be very different from an ops person in SF, we were looking for the same things, which were: open, honest communication, and the ability to take ownership. We were looking for people who were mission-driven for the company, and we were looking for people who were really excited about learning and were intellectually curious. When you hire for the same values, people get along easily.

Alejandro: Absolutely. How many people do you have now, Gautam?

Gautam Tambay: Two hundred.

Alejandro: Wow. That’s quite a number. Imagine that you go to sleep tonight, and you wake up five years later – insane snooze. You wake up in a world where the vision of Springboard is fully realized. What does that world look like?

Gautam Tambay: First of all, when you find that five years, make sure and send them to me.
[Laughter]

Alejandro: Yeah.

Gautam Tambay: Sometimes, I have trouble sleeping for more than six or seven hours. That’s a great question. For generations, we’ve been in a world where people had one job or two jobs throughout their career. My dad has one job in his career. Most people in our generation, they’ve had a couple of jobs in their careers. The average millennial is going to have 15 jobs in their career. It’s a fundamentally different world than we have ever lived in before. While the economy and work have completely changed, education is still stuck in the same place it was 500 years ago. That creates a massive opportunity for change. We believe that this current generation will, instead of consuming all of their education upfront until their mid-20s, instead, they’ll go back to transformational learning every few years, every five to seven years. So instead of spending $150,000 on a Master’s Degree when you are 25, you’ll spend maybe $10,000 six times in your career every five years. If you’re going to do that, you have to do it from anywhere in the world from the comfort of your couch in your pajamas, but still be able to have the transformational career change that you want. So we set for ourselves a goal at the start of this year that by the end of 2030, so in ten years, we want to transform one million lives, which is to put a million people into careers they love through our intensive online programs, which means that by that point, you’re going to be going home for Christmas, and your cousins will have taken a Springboard program. Or you’ll be hiking in a new country when that’s possible again, and you’ll see people in a Springboard sweatshirt because they’re graduates of the program, and you’ll see Springboard alumni in top places in the world, in powerful leadership positions and hiring back from the program. I think transforming lives, that’s what we do, and we want to transform lots of people’s lives because when you do that, you change not just their life, but that of their community and the people around them.

Alejandro: That’s amazing. One of the questions that I typically ask the guests that come on the show is if you had that opportunity to go back in time, Gautam, and have a chat with your younger self, maybe that younger self that in 2013 was about to launch Springboard. Now, knowing what you know, if you could go back in time and give yourself one piece of business advice before launching a business, what would that be and why?

Gautam Tambay: That’s a great question. I’ll give you two. One is, start early and take the plunge. Life is too short to be doing things that you’re not fully committed to. This is the advice I would give to maybe going back to 2005, where I would say, “Take the plunge and start a company earlier. You keep telling yourself that you want to learn things before you start a company.” To [41:08], the advice I would give is, most importantly, don’t get stalled by decisions. There are times when you are facing a challenging decision, and what ends up happening is you get stalled and stuck and don’t make any decision instead of stay in this limbo. That’s the worst thing you can do for a business or the worst thing you can do for even people around you. So it’s better to make a wrong decision than to make no decision. I feel that’s something that, in the first few years of the company, I learned the hard way. It’s like climbing a mountain. The worst thing you can do is stay still because you’ll freeze to death. It’s better to go in the wrong direction because then you can get some information and you can come back. So, just keep learning and getting information, and every time you make a decision, it leads to learning.

Alejandro: Absolutely. 100%, Gautam. For the people that are listening, what is the best way for them to reach out and say hi?

Gautam Tambay: Springboard.com is our website. I am [email protected]. I’m always happy to hear from other entrepreneurs, founders, people who want to go down this journey. I had a lot of help in getting this far. I can never pay it back; I can only pay it forward.

Alejandro: Amazing. Very, very profound. Gautam, thank you so much for being on the DealMakers show today.

Gautam Tambay: Alejandro, thank you for having me. This was a fantastic opportunity, and I’m excited to see what people have to say about this.

* * *
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