The Exchanges

Q But from, from what I read about you, I mean, you did land a couple of pretty good sales jobs out of college. Like, I think for a couple of years you were working for, for a, like a luxury travel agency, and then, uh, and then you got a job with IBM selling software. Um, what, what was that like?

A You know, it took me a while to, uh, you know, there was a little bit of an adjustment, right? I spent a lot of time selling to, Consumers in the last few years, and so now I was selling to IT managers, right, to IT people, and also selling in some cases to, um, to CIOs. So I got exposed to a much more complicated and much more sophisticated sales process. Um, but I loved it. Um, I found myself not really, like, I, I enjoy the work I did, but you know, I've always been a very, very impatient person. Um, and so, You know, at the time I looked at the CEO of IBM, and he was in his sixties, and it took him all 40 years to get there, and I didn't know that I had that much time to wait. So I wanted to be in an accelerated path. And so I started looking for a much smaller, uh, software company that was growing at a much faster rate. So at the time, you know, IBM was probably growing double digits every single year. And some of the businesses that I was looking at where, you know, probably going, growing double digits every month. And so really wanted to, um, to work for, you know, a smaller company with, uh, you know, more growth opportunity.

AI assessment note: “I got exposed to a much more complicated and much more sophisticated sales process.”

Q And I guess while you were there, um, you meet, you meet like this business contact who, um, I don't know the whole story, but, but like he starts giving you ideas for how you can, like, start your own company?

A Yeah. So, He told me that he'd actually helped a number of different entrepreneurs start a number of different, um, e-commerce businesses. So he said, most people start e-commerce businesses because they want to sell something in particular. They want to sell hand sanitizers. They want to sell masks, whatever it may be. It's like, well, that's one way to start a business, but he said an interesting, a really interesting way to start a high growth e-commerce business is to instead start a business around, around keywords that have a lot of traffic that you can optimize for. So instead of starting a business to sell hand sanitizers because you want to sell hand sanitizers, what if you started a business selling light bulbs? Because it turns out that there's a lot of traffic for light bulbs and no one's really satisfying that need very well. I'm just throwing that as an idea.

AI assessment note: “start a business around, around keywords that have a lot of traffic”

Q So do you, did you start a projector company?

A I did. I never used a projector in my life, right? Well, maybe you, maybe seen a few in a different meetings, right? But I never really bought one before. I set it one up before, but the analysis, you know, seemed compelling to me. And so we started a projector business and we called it projectorspot.com. And, uh, after something like two, three months of work, we set up the website and, uh, we were ready to take orders. And I should add that the, we didn't actually go out and buy projectors and sell them on the website. We established dropship and relationships with different wholesalers. And in a space of, you know, two to three months or so, we launched the business.

AI assessment note: “I did. ... And so we started a projector business and we called it projectorspot.com.”

Q I read that it was like, 350,000 dollars or something like that. Were you nervous about taking that investment? Because you owned a hundred percent of this thing, but at the same time, you needed the money.

A Yeah, so, I was ambivalent about raising money, to be honest with you, because, you know, I felt like I started the business, you know, in the most difficult way possible, you know, really, you know, putting everything I had, risking everything I had to start the business, and so, in some ways, I felt like a step backwards to have to, you know, cede, you know, some of the Ownership. But once I met David, um, that changed, um, in the sense that, like, I felt like I was going to have a, um, when I was going to be, you know, working with a successful entrepreneur himself and not just a, a money man, right? Um, I felt like, um, I could learn a lot from, from him. And so the ambivalence I had went away once I, once I met him.

AI assessment note: “I was ambivalent about raising money, to be honest with you”

Q Right. Once you, I mean, you essentially had two back-to-back failures, not, this is a good thing, because you're going to need those in the future. You're going to need to start and fail at a couple businesses. Um, did you think, maybe I'll take a break from starting a business for a while and go back and just get a safe job?

A Yeah, so this entire time, I never quit my day job, so what I end up doing is, um, I'm still working my, you know, my day job at that time, traveling all over the country. But what I realized was that I was, I started all these different businesses, not because I was passionate about solving a problem or, and not because a problem necessarily existed. I was doing all these things because I wanted to start a business. And so I thought that I wanted to take a break. And rather than forcing a business, uh, idea, I thought that I needed to pick a problem that truly existed and I needed to pick something that I was, uh, you know, really excited and committed to being a student of it. And I decided that I would basically take a break from starting businesses until I found, until I found that idea that check all those boxes.

AI assessment note: “this entire time, I never quit my day job”

Q Did people think it was a good idea?

A No, they didn't think so. They thought it was a solved problem. I remember when I, uh, when I was leaving and I told my boss I was leaving. He's like, you're leaving for that? He felt like he'd filled me that I, you know, like he felt like I was, uh, like I got, get desperate and I, you know, and I'm pursuing, you know, scheduling. That's a solved problem. Like nobody needs that. But yeah, it was not, it was definitely not obvious. I didn't quite know how I was going to fund it. Um, but I, the decision to me was clear. And so I began to, um, put together a pitch deck and, um, Start going to different, um, events, trying to meet investors.

AI assessment note: “No, they didn't think so. They thought it was a solved problem.”

Q So you graduated from college, and, and when you did, did you have a, like, a ton of job offers?

A No, far from it. I think one of the things I've learned, you know, myself, you know, many, many years after, is I think being the child of immigrants, I think maybe hurt my understanding of how to, how to be successful in the business world in America. And so I didn't do some of the things that my peers were doing, like internships, I didn't do those things. In hindsight, I should have done those things, and you know, my parents would have known to, I mean, I, you know, they would have probably pushed me to do that if they were from here, but they didn't, my mom didn't know that herself. Not to put the blame on her, but I think there's, I am probably more savvy about how those things work today.

AI assessment note: “No, far from it.”

Q What was it that you thought you needed?

A Yeah. So a few things I thought I needed at the time. So one, there were a lot of products on the market that were really, um, tailored to brick and mortar businesses. They do a lot of appointments, right? So if you are a salon and you do a hundred appointments a day, there's a lot of great software for you, right? If you are an enterprise software sales rep that really does maybe, you know, five external meetings a day or three or four, there were no really good options for you. The other thing I noticed was that, you know, as a salesperson, one of the things I knew, um, very well was that just because you want to meet with somebody, it doesn't mean they want to meet with you. Right. And so I thought a lot of the products that existed in the market really spent a lot of time designing for the users of the software and not so much the recipients of the invitation. And so I thought that if this would gain mass adoption, you really needed to build for both For all participants, you needed to make it a great experience for every, um, for all the users of the product, whether they were your own registered users or the people who were receiving invitations from your registered users. Those are some of the things that I, uh, that I noticed.

AI assessment note: “a few things I thought I needed at the time. So one, there were”

Q So by the fall, around September of 2013, the first version of this product is available, but you had spent all your money on developing it, so how were you going to, I don't know, pay for the servers and pay for, I mean, get, get the word out about it? I mean, how, because you had no money left, right?

A Yeah, so I got, I know, help along the way, um, through Railsware actually, so a few things happened. Um, As Railsware was building the product, they got connected to another potential client, a software company in San Francisco that's gone on and done really well. It's a multi hundred million dollar business now. And that company was looking to engage them to do some work for them. And so Railsware was, uh, was like, hey, let's show you this product that we're building. Right? So they show them Calendly. And at the time Calendly is not quite, it's in a, it's not quite ready to be in a public beta, but what, what ends up happening is they love the product. And so somebody from their, from their customer success team signs up for the product and starts using it to schedule onboarding calls with their customers, which those customers happen to be, um, K to K through 12 schools. So a customer success person from this company in San Francisco starts scheduling Onboarding calls with, uh, you know, K through to all schools.

AI assessment note: “starts using it to schedule onboarding calls with their customers”

Q All in, all in Atlanta, the Atlanta area?

A All in the Southeast. So a few people in Atlanta, a few people in the Southeast. I had, you know, um, a guy from a, a pretty big firm. Not only did he, you know, so I, I mean, I'll tell you, I had a very, what I thought was a very condescending kind of experience. So at the time I was actually in Kiev and Right. So I'd flown to Kiev to work with Railsware, and I stayed up till two a.m. to meet with this person, and then he stands me up. Right. So just a lot of, like, a lot of experiences like that that were just, you know, it's one thing to not invest, but it's another thing to, to kind of treat people like that. Yeah. How much is that? It's just the arrogance of, you know, somebody who thinks they're an important VC versus race. I know, who knows, but I mean, I do know that, uh, Many other entrepreneurs who didn't have as much, who hadn't made as much progress, had more offers than I did.

AI assessment note: “All in the Southeast. So a few people in Atlanta, a few people in the”

Q So this is like B to B stuff, right?

A Yeah. And so I really enjoyed working for the company, but while I was at the company, part of the onboarding process is you get a chance to To meet with the founders, and you know, they, they tell the story, the company's founding story, and that story just really opened up my eyes. Why? You know, it was the first time I heard about the founding story of, uh, of a company, of a successful company, because before then, I thought that most people who started, you know, very successful companies, they just hit the ground running on day one. They knew exactly what product they want to deliver to the market. Customers receive it, accept it, they break their backs, they pay them money. But what I learned from this founder was, It took them eight years to really, uh, get to product market fit as we call it today. And the idea pivoted many, many, many different times. Um, and the reason that that business, uh, became successful was had more to do with their ability to learn from their customers, their, their own resilience. So from that point on, I think it made me realize that, you know, entrepreneurship was way more attainable than I thought it was before that. So I thought I had to be You know, I just, yeah, it's just the story made me realize that I didn't have to have all the answers, but if I saw something that I thought needed to be changed, I just needed to take action and, um…

AI assessment note: “Yeah. And so I really enjoyed working for the company”