The Exchanges

Q You said there about their expertise with, as you said there, with consumer markets and how they could apply that to you with the enterprise perspective. What were the other pillars or core fundamentals that you looked For them from your investor base in the team of all stars that you attracted?

A Yeah, I can actually go through where literally every single investor and what we thought they brought to the table. I'll give a great example. We were able to bring on, uh, lucky enough to bring on Slack as an investor, and they're really that next generation of enterprise software. We want to make sure, uh, we had them as close partners and we're part of their ecosystem. Another great example is when we brought on SUSE, uh, They've been very, very good in terms of helping us with our long-term strategy, but also in terms of the hygiene from an institutional VC perspective. And then you look at some CEO coaches as well, and that's where we brought on angels like Elad Gill and Adrian Oon, both CEOs in their own right. Uh, they can help us from a coaching perspective and even Charlie Songhurst, who actually understood, uh, enterprise extremely well from his time at Microsoft. And so, um, the list goes on, but every person we brought on, we said, look, where does this investor fit? And how can we leverage them to help us be successful in the future?

AI assessment note: “every person we brought on, we said, look, where does this investor fit?”

Q them on the show previously. Fantastic guests. Um, but, but, and obviously, they introduced But this is a VC show, as we, as we all know. So I'd love to discuss the investment aspect now, and, and you've previously said you should build your investor team like a sports team. So I'm intrigued. What do you mean by this, and how did it affect how you manage the fundraising process?

A Yeah, that's a great question. Usually the, the feedback you get from typical VCs is that, even mentors, is that you should always choose your VC and As almost how you would choose your spouse, because you're basically going to be married, uh, to them for, for your lifetime, uh, as a company. Uh, but I had a different mentor who actually said, look, Ted, you should actually approach this differently. Don't just look at it as a spouse you would look for, but really look at it as a team you're building and think about the skill set that each VC brings to the table. A good analogy is if you were, let's, let's say women's world cup team, you wouldn't have 11, uh, hope solos running around the field. You would need forward, you would need a defender, you would need a midfielder. And so you need all these different pieces in place actually to win the game, which is really the name of the game here from a, from a startup perspective. And so when we looked at our investors, everyone that we chose had a specific purpose in helping us get to that next level. And so even just bringing up initialized again, a good example there is that we went to them because not because they were hardcore enterprise, uh, seed investors, but really because they understood consumer markets extremely well. And we wanted to apply those same growth strategies to the enterprise market, especially with Alexa's e…

AI assessment note: “everyone that we chose had a specific purpose in helping us get to that next level”

Q Now, I'd love to get started today by discussing a bit about you and how you came to found WorkRam. So what's the little brief bio on you?

A Yeah, so I'll probably start in my, in my mid-twenties, I actually, uh, founded my first startup, and it was a huge failure. Pretty much, uh, Took everything that was hot at the time, whether it be mobile, social, and local, and try to combine it all into one startup, and it failed pretty, pretty miserably. The thing I learned from that was really twofold. One was that if I wanted to go start a company again, I would definitely go learn from the best before I went and started that company. I really understood, understand how to actually build a company from scratch. And then two is actually go work on something that had true meaning and impact. They don't want to really work on what we call the first world problems are really a big pain point that we could actually go solve. And so I think from that experience, I actually packed my bags, moved up to Silicon Valley and was lucky enough to basically find box and box took me under their wing for about five years. I was able to accomplish both of those goals. One was I was able to go learn from the best from the likes of Aaron Levy and Dylan Smith and understand how to build a hyper growth business. Um, and then too, while I was there towards the end of my tenure there, I found a big problem. Um, that's kind of what led us to work ramp, a big problem around, uh, how people were developing and training their employees, especially in…

AI assessment note: “we thought the convergence, uh, of those two things allowed us to go start work ramp.”

Q them on the show previously. Fantastic guests. Um, but, but, and obviously, they introduced But this is a VC show, as we, as we all know. So I'd love to discuss the investment aspect now, and, and you've previously said you should build your investor team like a sports team. So I'm intrigued. What do you mean by this, and how did it affect how you manage the fundraising process?

A Yeah, that's a great question. Usually the, the feedback you get from typical VCs is that, even mentors, is that you should always choose your VC and As almost how you would choose your spouse, because you're basically going to be married, uh, to them for, for your lifetime, uh, as a company. Uh, but I had a different mentor who actually said, look, Ted, you should actually approach this differently. Don't just look at it as a spouse you would look for, but really look at it as a team you're building and think about the skill set that each VC brings to the table. A good analogy is if you were, let's, let's say women's world cup team, you wouldn't have 11, uh, hope solos running around the field. You would need forward, you would need a defender, you would need a midfielder. And so you need all these different pieces in place actually to win the game, which is really the name of the game here from a, from a startup perspective. And so when we looked at our investors, everyone that we chose had a specific purpose in helping us get to that next level. And so even just bringing up initialized again, a good example there is that we went to them because not because they were hardcore enterprise, uh, seed investors, but really because they understood consumer markets extremely well. And we wanted to apply those same growth strategies to the enterprise market, especially with Alexa's e…

AI assessment note: “everyone that we chose had a specific purpose in helping us get to that next level.”

Q You said there about their expertise with, as you said there, with consumer markets and how they could apply that to you with the enterprise perspective. What were the other pillars or core fundamentals that you looked For them from your investor base in the team of all stars that you attracted?

A Yeah, I can actually go through where literally every single investor and what we thought they brought to the table. I'll give a great example. We were able to bring on, uh, lucky enough to bring on Slack as an investor, and they're really that next generation of enterprise software. We want to make sure, uh, we had them as close partners and we're part of their ecosystem. Another great example is when we brought on SUSE, uh, They've been very, very good in terms of helping us with our long-term strategy, but also in terms of the hygiene from an institutional VC perspective. And then you look at some CEO coaches as well, and that's where we brought on angels like Elad Gill and Adrian Oon, both CEOs in their own right. Uh, they can help us from a coaching perspective and even Charlie Songhurst, who actually understood, uh, enterprise extremely well from his time at Microsoft. And so, um, the list goes on, but every person we brought on, we said, look, where does this investor fit? And how can we leverage them to help us be successful in the future?

AI assessment note: “I can actually go through where literally every single investor and what we thought”

Q Now, I'd love to get started today by discussing a bit about you and how you came to found WorkRam. So what's the little brief bio on you?

A Yeah, so I'll probably start in my, in my mid-twenties, I actually, uh, founded my first startup, and it was a huge failure. Pretty much, uh, Took everything that was hot at the time, whether it be mobile, social, and local, and try to combine it all into one startup, and it failed pretty, pretty miserably. The thing I learned from that was really twofold. One was that if I wanted to go start a company again, I would definitely go learn from the best before I went and started that company. I really understood, understand how to actually build a company from scratch. And then two is actually go work on something that had true meaning and impact. They don't want to really work on what we call the first world problems are really a big pain point that we could actually go solve. And so I think from that experience, I actually packed my bags, moved up to Silicon Valley and was lucky enough to basically find box and box took me under their wing for about five years. I was able to accomplish both of those goals. One was I was able to go learn from the best from the likes of Aaron Levy and Dylan Smith and understand how to build a hyper growth business. Um, and then too, while I was there towards the end of my tenure there, I found a big problem. Um, that's kind of what led us to work ramp, a big problem around, uh, how people were developing and training their employees, especially in…

AI assessment note: “that's kind of what led us to work ramp, a big problem around”

Q How do you, how do you view competition? Do you view it in the way that row your own race and focus on your own boat and, and you'll get to your goal? Or do you think it's very important to have an overview of the competitive market and who's coming and who's Potentially, uh, usurping your number one position.

A I would say healthy balance of the two. I think if you look at really wanting to innovate on the markets, you don't really pay attention too much to your competition. And that's kind of back to that product market fit question where you really want to make bets that none of your competitors are even thinking about. And so I think if you can make sure you keep an eye on growth markets and not worry too much about the competition when looking at those bets, That's extremely helpful. But then from an execution standpoint, you want to notice how you actually can actually beat A day, hand-to-hand combat, and you want to keep track of them then, but I think, uh, from a macro standpoint, you really want to kind of paint your own, uh, vision and go down your own path with respect to your competitors.

AI assessment note: “I would say healthy balance of the two.”

Q Now, you teed me up so nicely there with the learning from the best from Aaron and Dylan, but I'd love to ask them, with the incredible journey that you experienced with Box in their kind of period of hyper-growth, What were the big takeaways from you in seeing this, this real rocket ship growth of box?

A Yeah, that's, that's a great question. I would probably frame it in two ways, right? Or, or two big lessons I learned. Um, I would say first in observing Aaron, I was able to see a leader actually almost will an entire market into place. Um, he basically came into a old stodgy, uh, market of enterprise, uh, Content management and basically will it into being a hot, sexy space that a lot of people paid attention to. He's even able to almost take a class of decision makers, which was the CIOs at the time and make them really set of a set of sexy buyers. And so that was really interesting to see how he did that both from a marketing and branding perspective kind of leads into the second point too, of, of kind of what I learned from my experience there is that not just from willing that market to place What box did a really, really good job of kind of understated is execution. And when you think about box, it gets a lot of flack for how much money they had spent. Um, especially when they're going public, how much they were spending on customer acquisition. Uh, but they knew that in order to execute in that market, they had to spend heavily. They had to be the number one brand in the enterprise market. And it was so important to make sure that they capitalize on that brand and executed from a go to market perspective. So one of the biggest strengths of Box that not a lot of people k…

AI assessment note: “two big lessons I learned. Um, I would say first in observing Aaron”

Q I do want to revert back though to the, to the bull puck eyes, um, suggestion, because obviously your learnings from YC are immensely interesting to me. So what were the big learnings for you from YC? Um, And the interaction with the mentors that, that shaped your attitude to now the operational side of work ramp.

A I would say YC taught you really, really three big things. I would say, um, I would say the first is having the office hours and in those office hours, you learn so much about how to actually run a business. So, and so during the program, you basically get to set up office hours with any of the successful partners or part-time partners. And you really get picked their brains on all assets of the business. And so I learned a ton during that time, anything from how to hire, um, how to build the product to how to actually land customers. Uh, so that was extremely beneficial for us when we went through the program. Uh, I would say too, is really having that pure network during YCU was extremely helpful in terms of actually building up the level of competition that you have to actually drive you to that next level. If you look at baseball teams, for example, the teams that are usually the best are the ones that have multiple aces on their starting lineup from a pitching standpoint. It's almost like that in YC where you look at other companies and they help drive you to, you drive each other to that next level of success.

AI assessment note: “YC taught you really, really three big things. I would say, um, I would say the first”

Q Now, you teed me up so nicely there with the learning from the best from Aaron and Dylan, but I'd love to ask them, with the incredible journey that you experienced with Box in their kind of period of hyper-growth, What were the big takeaways from you in seeing this, this real rocket ship growth of box?

A Yeah, that's, that's a great question. I would probably frame it in two ways, right? Or, or two big lessons I learned. Um, I would say first in observing Aaron, I was able to see a leader actually almost will an entire market into place. Um, he basically came into a old stodgy, uh, market of enterprise, uh, Content management and basically will it into being a hot, sexy space that a lot of people paid attention to. He's even able to almost take a class of decision makers, which was the CIOs at the time and make them really set of a set of sexy buyers. And so that was really interesting to see how he did that both from a marketing and branding perspective kind of leads into the second point too, of, of kind of what I learned from my experience there is that not just from willing that market to place What box did a really, really good job of kind of understated is execution. And when you think about box, it gets a lot of flack for how much money they had spent. Um, especially when they're going public, how much they were spending on customer acquisition. Uh, but they knew that in order to execute in that market, they had to spend heavily. They had to be the number one brand in the enterprise market. And it was so important to make sure that they capitalize on that brand and executed from a go to market perspective. So one of the biggest strengths of Box that not a lot of people k…

AI assessment note: “two big lessons I learned. Um, I would say first in observing Aaron”

Q Okay. Super interesting. You mentioned product markets. Fit there. In discussing VC selection, as many VCs fundamentally look for the hailed product market fit. How do you view product market fit? I had Justin Kahn from YC on the show. He said it was when you have 10 unaffiliated customers purchase your goods. What's your take on when you reach product market fit? How do you know?

A I think product market fits this vague term that almost everybody uses in a different context, but I'll give a good story. I remember When we were leaving YC, Paul Buchite sat the entire batch down, so all hundred companies or so, and he told us on our last day, he said, look, none of you guys are at product market fit, and we were looking around the room, and it was, we had some very successful companies there, and I don't think he was saying that to be mean-spirited, but what he was really saying was that, look, don't be satisfied with wherever you're at. Always look for that next area of growth, and so I want to answer that question, Harrius, as saying, I think there's always varying degrees of product market fit, Um, and you need to always look at more areas you can grow into. If you look at like an Amazon, for example, they're never happy with where they're at. That's why they put huge investments in Alexa over these holidays. Or you look at Airbnb, where they're rolling out their new flight booking service, or Uber, who's investing heavily into Uber Eats. All of these companies, you would say, have great product market fit, but they're always looking for And so, I think for us, I think we look at product market fit as that, hey, we're growing revenue pretty well. We're growing our customer acquisition at a steady pace, but we're always looking for that next level of growt…

AI assessment note: “I think there's always varying degrees of product market fit”

Q I do want to revert back though to the, to the bull puck eyes, um, suggestion, because obviously your learnings from YC are immensely interesting to me. So what were the big learnings for you from YC? Um, And the interaction with the mentors that, that shaped your attitude to now the operational side of work ramp.

A I would say YC taught you really, really three big things. I would say, um, I would say the first is having the office hours and in those office hours, you learn so much about how to actually run a business. So, and so during the program, you basically get to set up office hours with any of the successful partners or part-time partners. And you really get picked their brains on all assets of the business. And so I learned a ton during that time, anything from how to hire, um, how to build the product to how to actually land customers. Uh, so that was extremely beneficial for us when we went through the program. Uh, I would say too, is really having that pure network during YCU was extremely helpful in terms of actually building up the level of competition that you have to actually drive you to that next level. If you look at baseball teams, for example, the teams that are usually the best are the ones that have multiple aces on their starting lineup from a pitching standpoint. It's almost like that in YC where you look at other companies and they help drive you to, you drive each other to that next level of success.

AI assessment note: “YC taught you really, really three big things. I would say, the first is”

Q to be a VC, just a VC, VC, VC. Now I'm, you know, the world's youngest VC, and all I want is my first deal. That's not enough. That's, you know, there's always the next step. Do you as the founder of WorkRamp ever sit back and appreciate what you've done, the product you've built, the funding that you've achieved? Do you ever sit back and appreciate what you've done?

A Yeah, you, you do. I'll bring up a, I'll bring up a good story actually about Aaron Levy. I remember, and I'll bring this back to my own personal experience. I remember every time we close a monster quarter and didn't think we could go any higher that literally that same morning at one AM right after the quarter. And he would send out an email to the entire company saying, Hey, great quarter, but here's all the things we need to do over the next three to six months. And so he would dedicate maybe a month to celebrating it and then really look Forward, uh, to what was up next. And I remember even when we went public, he put posters around the office, uh, talking about companies that were built for the longterm, like Apple and IBM and Microsoft. And so I think it is to answer your question. I think it's important to reflect back on how you've done like a great example, since we just crossed the new year's mark, uh, we looked back on our year and said, Hey, this was a really successful year. We actually hit all of the goals we had set out to do during the year. Um, but I think it's really important to always push yourself into what you want to do next and do that pretty quickly because you're, you're really, uh, only as, as good as what you're about to do in that next quarter or that next year. And so I think it's really important to, yes, take a second to pause and reflect, but t…

AI assessment note: “Yeah, you, you do... I think it's important to reflect back on how you've done”

Q I'm super intrigued. You mentioned brand building there a lot, and with regards to enterprise, it's often a slightly mysterious world, the brand building of enterprise companies. So I'm intrigued how How do you think that kind of builds itself and the core fundamentals to building a successful enterprise brand?

A Yeah. So it's, it's funny. A lot of people, especially in startup world, think that if you have the best product, your, your company will win. And I think in the enterprise realm, that's not always true. I think the companies that actually have both a good product, but even more important, the best brand will win. If you look at Salesforce.com and Uh, they don't have the best product in the world, but they have the best brand. If you look at NetSuite, if you look at success factors, if you look at concur, no one's ever said, Hey, those are the best products on the market, best of breed. But what they all have is a well-trusted brand for the market. And so I think for us, we, we look at that as being a critical part of both your moat against competitors, but also in order to actually get, gain customers trust to actually use your products. And so, we focus a lot on that, especially with our VCs as well. Um, I know Gary Tan and Alexis Ohanian from our investors at Initialize, they've been very, very good in helping us build our brand. They brought on Kim Mai Cutler onto their team from TechCrunch, and she's been extremely helpful in actually coaching us through how to build a great enterprise brand.

AI assessment note: “coaching us through how to build a great enterprise brand.”

Q to be a VC, just a VC, VC, VC. Now I'm, you know, the world's youngest VC, and all I want is my first deal. That's not enough. That's, you know, there's always the next step. Do you as the founder of WorkRamp ever sit back and appreciate what you've done, the product you've built, the funding that you've achieved? Do you ever sit back and appreciate what you've done?

A Yeah, you, you do. I'll bring up a, I'll bring up a good story actually about Aaron Levy. I remember, and I'll bring this back to my own personal experience. I remember every time we close a monster quarter and didn't think we could go any higher that literally that same morning at one AM right after the quarter. And he would send out an email to the entire company saying, Hey, great quarter, but here's all the things we need to do over the next three to six months. And so he would dedicate maybe a month to celebrating it and then really look Forward, uh, to what was up next. And I remember even when we went public, he put posters around the office, uh, talking about companies that were built for the longterm, like Apple and IBM and Microsoft. And so I think it is to answer your question. I think it's important to reflect back on how you've done like a great example, since we just crossed the new year's mark, uh, we looked back on our year and said, Hey, this was a really successful year. We actually hit all of the goals we had set out to do during the year. Um, but I think it's really important to always push yourself into what you want to do next and do that pretty quickly because you're, you're really, uh, only as, as good as what you're about to do in that next quarter or that next year. And so I think it's really important to, yes, take a second to pause and reflect, but t…

AI assessment note: “yes, take a second to pause and reflect, but then look at what's up next”

Q a quick fire, and it reverts back to the VC selection element, uh, and, and in particular, how VCs, uh, use founders, uh, and so, if we break this up into short-term and long-term, I'd love to hear how you view the short-term versus the long-term value out of invest Investors and how you look to really leverage their abilities and get the most out of having them on board?

A Yeah, that's a great question, Harry. I would say when you look at, especially seed investors, I think by definition, all seed investors should be long-term investors, and they will all probably say that, um, uh, especially because they're going to be the first money in, uh, but what we realized during that process is that some definitely were not long-term focused. You can tell that even with small things like how they do due diligence, you see the ones that are focusing It's extremely on the, just the small metrics early on, like LTV or, or customer acquisition costs. They're not really looking at the long game. And so you really want to just make sure you avoid the investors that aren't actually long-term focused. And then when you find a really good investor, I'll give you a good example, like, like Asusa ventures, they're extremely good, both from a long-term perspective and short-term perspective, long-term perspective. A good story there is, is one of their partners, Leo, who I believe, you know,

AI assessment note: “some definitely were not long-term focused. You can tell that even with small things”

Q Okay. Super interesting. You mentioned product markets. Fit there. In discussing VC selection, as many VCs fundamentally look for the hailed product market fit. How do you view product market fit? I had Justin Kahn from YC on the show. He said it was when you have 10 unaffiliated customers purchase your goods. What's your take on when you reach product market fit? How do you know?

A I think product market fits this vague term that almost everybody uses in a different context, but I'll give a good story. I remember When we were leaving YC, Paul Buchite sat the entire batch down, so all hundred companies or so, and he told us on our last day, he said, look, none of you guys are at product market fit, and we were looking around the room, and it was, we had some very successful companies there, and I don't think he was saying that to be mean-spirited, but what he was really saying was that, look, don't be satisfied with wherever you're at. Always look for that next area of growth, and so I want to answer that question, Harrius, as saying, I think there's always varying degrees of product market fit, Um, and you need to always look at more areas you can grow into. If you look at like an Amazon, for example, they're never happy with where they're at. That's why they put huge investments in Alexa over these holidays. Or you look at Airbnb, where they're rolling out their new flight booking service, or Uber, who's investing heavily into Uber Eats. All of these companies, you would say, have great product market fit, but they're always looking for And so, I think for us, I think we look at product market fit as that, hey, we're growing revenue pretty well. We're growing our customer acquisition at a steady pace, but we're always looking for that next level of growt…

AI assessment note: “we look at product market fit as that, hey, we're growing revenue pretty well.”

Q a quick fire, and it reverts back to the VC selection element, uh, and, and in particular, how VCs, uh, use founders, uh, and so, if we break this up into short-term and long-term, I'd love to hear how you view the short-term versus the long-term value out of invest Investors and how you look to really leverage their abilities and get the most out of having them on board?

A Yeah, that's a great question, Harry. I would say when you look at, especially seed investors, I think by definition, all seed investors should be long-term investors, and they will all probably say that, um, uh, especially because they're going to be the first money in, uh, but what we realized during that process is that some definitely were not long-term focused. You can tell that even with small things like how they do due diligence, you see the ones that are focusing It's extremely on the, just the small metrics early on, like LTV or, or customer acquisition costs. They're not really looking at the long game. And so you really want to just make sure you avoid the investors that aren't actually long-term focused. And then when you find a really good investor, I'll give you a good example, like, like Asusa ventures, they're extremely good, both from a long-term perspective and short-term perspective, long-term perspective. A good story there is, is one of their partners, Leo, who I believe, you know,

AI assessment note: “what we realized during that process is that some definitely were not long-term focused”

Q I'm super intrigued. You mentioned brand building there a lot, and with regards to enterprise, it's often a slightly mysterious world, the brand building of enterprise companies. So I'm intrigued how How do you think that kind of builds itself and the core fundamentals to building a successful enterprise brand?

A Yeah. So it's, it's funny. A lot of people, especially in startup world, think that if you have the best product, your, your company will win. And I think in the enterprise realm, that's not always true. I think the companies that actually have both a good product, but even more important, the best brand will win. If you look at Salesforce.com and Uh, they don't have the best product in the world, but they have the best brand. If you look at NetSuite, if you look at success factors, if you look at concur, no one's ever said, Hey, those are the best products on the market, best of breed. But what they all have is a well-trusted brand for the market. And so I think for us, we, we look at that as being a critical part of both your moat against competitors, but also in order to actually get, gain customers trust to actually use your products. And so, we focus a lot on that, especially with our VCs as well. Um, I know Gary Tan and Alexis Ohanian from our investors at Initialize, they've been very, very good in helping us build our brand. They brought on Kim Mai Cutler onto their team from TechCrunch, and she's been extremely helpful in actually coaching us through how to build a great enterprise brand.

AI assessment note: “extremely helpful in actually coaching us through how to build a great enterprise brand.”

Q And then let's finish on the next five years for you and for work ramp. What have we got in store? Yeah.

A So we didn't talk too much about work ramp, but just at a, at a really high level, I think in the next five years, if you look at how Google tried to organize the world's information, mostly from a consumer perspective, uh, I think our goal is to organize all the knowledge, uh, within enterprises, and so, uh, we have different ways we want to actually achieve that goal, and our first way to start that is really with helping people train and develop within organizations, and so I think in the next five years, if we can get to a point to where we're actually, uh, starting to execute on that mission, that'd be a really good spot, uh, for us to be in.

AI assessment note: “I think our goal is to organize all the knowledge, uh, within enterprises”