About this episode

I’d like you to meet Alina Vandenberghe, co-founder of Chili Piper and Gipsybot. (Yes, that’s right, she co-founded TWO startups.) Chili Piper is an incredibly powerful sales tool for enterprises. Her second startup, Gipsybot, is a productivity tool to help you prioritize what is important to you, not what others delegate to you.

The reason I wanted to unpack Alina’s story is multi-faceted. First, she is running two startups at the same time, and I find that to be incredibly impressive, as well as quite uncommon. Oh, and one of those startups just closed on a Series A round of funding. Secondly, she is an immigrant from Romania. Immigrant founder stories have a unique layer to them that help frame all of our perspectives. Lastly, she is royalty in the mobile development space. Now, she would never say that about herself, but when you develop one of the first apps for the “yet to be released” iPad and Steve Jobs chooses to use your app from the Apple stage as he is revealing the all-new, never before seen iPad… that is quite a remarkable accomplishment.

Alina’s Startup Story is fascinating and begins unlike any other founder we have had on the show, so let’s get started. This is Alina Vandenberghe’s startup story.

In this episode, you’ll hear

  • Alina’s early ventures (beginning around age 9!) featuring her entrepreneurial spirit and how she didn’t even realize it was entrepreneurship
  • Her frustration with the corporate world, how others recognized her skills/personality traits as perfect for a startup and encouraged her to begin that journey
  • The challenges of operating a fully distributed workforce and the benefits of being able to tap into a larger talent pool
  • How culture is managed with staff members in remote locations and the need for attendance on company calls and occasional meetings in person
  • The importance of managing mental health during the “founder’s depression” period and having a plan to avoid burnout
  • How GipsyBot was developed from a need to accurately manage priorities and goals to change the way people work so they can achieve their own goals and not just the priorities of others
  • The fact that managing two startups is possible
  • For businesses to succeed and meet future goals, a positive environment must be created for workers and clients so that customers can get the results they want and a big return on their investment

“I know how hard it is to get back up when you’ve been completely knocked down, but it is at that moment in time when big things happen.”
—Alina Vandenberghe, Chili Piper & GipsyBot

Resources from this episode

Our Sponsor Podcoin: https://www.podcoin.com - Listen to this episode to grab your special discount code
Chili Piper: https://www.chilipiper.com/
GipsyBot: https://gipsybot.com/
Alina Vandenberghe on Linkedin: https://www.linkedin.com/in/alinav/
The Startup Story on Instagram: https://www.instagram.com/thestartupstory/

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Special Guest: Alina Vandenberghe.

Episode transcript

The Startup Story - Alina Vandenberghe

Alina Vandenberghe: Hi. This is Alina Vandenberghe. I'm cofounder of Chili Piper and Gipsybot, and this is MY startup story.

James McKinney: Every wildfire began with a spark. Every superhero has an origin story. And every single startup has a moment that they point to as their beginning. And every founder has a purpose that drove them in the midst of all obstacles. That is The Startup Story.

James McKinney: Before we jump into this week's episode, I have to ask. Are you connected with us on our social media platforms? Throughout the week, we post content from our episodes as well as updates on the show. In fact, this last week we had a huge moment of celebration. We learned that The Startup Story has become one of the top 100 business podcasts in Australia and the United States. What is even more amazing is that we also learned that we're the 11th most popular business podcast in the UK. Never in a million years did I think this was our trajectory. In fact, all of those closest to me will attest to the fact that the only statement related to listener numbers that I ever voiced was that I hope we would get to 10,000 monthly listens, and wow have we blown that number out of the water.

I'm sure that there will be many more moments of celebration and powerful content to share throughout our journey, so please make sure to follow us on Facebook and Instagram @TheStartupStory and on Twitter @StartupStory_. And of course, definitely follow us on LinkedIn. Just search for The Startup Story company page. One last thing before we get into our episode. I want to thank 29Robi who left a review on iTunes that read, "Thanks for a great podcast, James. Even though I am far from an entrepreneur, I truly enjoy hearing the "pick yourself up and dust yourself off" stories of the human spirit. You are a great interviewer." Wow, thank you 29 Robi. Thank you for that incredible compliment as well as taking the time to write a review. I also love that you listen to these stories even though you're not an entrepreneur because while you may not be an entrepreneur, these stories help to expand what we start to believe is truly possible for ourselves. All of us are far more capable than we believe. If you have found any value in The Startup Story, please leave a written review on iTunes and plug your brand, URL, or social media accounts. It becomes like a mini ad and is just my way of saying thank you for taking the time to leave a review. The written reviews mean a ton for being discovered in the iTunes platform. Now, let's jump into this week's episode.

Our guest today is Alina Vandenberghe, cofounder of not one startup but two startups at the same time. Her startups are Chili Piper and Gipsybot. Chili Piper is an incredibly powerful sales tool for enterprises. Right now, if a lead visits a website they fill out a form and wait for someone to contact them. Chili Piper facilitates a handoff right then and there, and in some cases increasing the sales close rate by 61%. If you're an entrepreneur, you might want to check it out. Sales matter. Her second startup is Gipsybot and is a productivity tool to help you prioritize what is important to you, not what others delegate off to you. It's still in beta at the moment, so more to come on that one. But the reason I wanted to unpack Alina's startup story, it's multi faceted.

First, the fact that she's running two startups at the same time is incredibly impressive and not too common. One of those startups just closed on a Series A round of funding, as a matter of fact. Secondly, she's an immigrant from Romania, and immigrant founder stories have a unique layer to them that help frame all of our perspectives. And lastly, she is royalty in the mobile development space. Now, she would never say that about herself, but when you develop one of the first apps for the yet to be released iPad and Steve Jobs chooses to use your app from the Apple Stage as he is revealing the all new never before seen iPad, that is quite a remarkable accomplishment, and I can't believe that we get to unpack her story.

Now, Alina's startup story is fascinating and begins unlike any other founder we have ever had on the show.

Alina Vandenberghe: My childhood years were spent in communist and post communist Romania, and entrepreneurship wasn't really a think, or something that I've been exposed to whatsoever. My parents worked both in factories pretty much, and they had this perception that to do well in life, you had to be the boss of the factory, right? So they kind of steered me to the direction of being the boss. It was a notion that I hadn't fully grasped, but I really wanted to be the manager of people, in order to gain trust and respect because that's how they were brainwashed, and that's how they brainwashed me.

So I wasn't exposed to entrepreneurship whatsoever as a child. However, because their income was quite limited, I had to work to pay for my books and whatever other expenses I may have. So I started all sorts of ventures as a kid, without knowing that I was an entrepreneur.

James McKinney: What were those ventures as a kid, and how old were you when you started realizing that you could create your own money?

Alina Vandenberghe: I started teaching smaller kids English, then I started teaching smaller kids math. Then I started selling lipstick. My biggest venture was the lipstick selling business. I had like 40 reps working for me and I had to open subsidiary so that I can pay taxes, but I wasn't allowed because I was underage. So I opened a firm on a fake signature, and the person who created the company for me accepted bribes, and the bribe was a pack of cigarettes because that's what post communist Romania looked like at that time. I didn't realize it was entrepreneurship until very late.

James McKinney: One, that is amazing. I love… so how old were you in that lipstick hustling days? I just want to put a stamp on that.

Alina Vandenberghe: I started when I was 12 or 13, somewhere around there.

James McKinney: And you had reps, I love that.

Alina Vandenberghe: I had 40 reps and I also did something super strange. I decided that I will help everybody in the building, there were several apartments, that I would help everybody with paying their bills for electricity and water, and I would manage that for everybody and I would take a little commission. So I managed to pay part of our rent with me managing everybody else's bills in the building. That was much earlier. It might have been like nine.

James McKinney: This is amazing. But now looking back, obviously looking back we can see kind of the breadcrumbs of life and you can see how that was… it became very clear to you now, I'm assuming, that you look back and say, "Yeah, I was destined to be an entrepreneur." But at the time, you were just trying to make money, make ends meet to provide for family, your parents, and also books for yourself and your own necessities, right?

Alina Vandenberghe: Yeah. I had no idea what was it called, but I obviously had the instinct and the energy to do all these things, and I was doing so many things in parallel. Some of them I don't even remember probably, they weren't that important.

James McKinney: So as you progressed in age, and now you're coming to the end of your schooling, which in Romania is schooling the same as ours where around 18, you're done with it at that point?

Alina Vandenberghe: Yeah, it's similar. 18 years to finish high school.

James McKinney: So what did you think you wanted to do at the end of high school?

Alina Vandenberghe: I wanted to be the boss. That was my goal to be the boss, so I had a big sign on my bedroom door, which I shared with my sister, and it says, "The boss, do not disturb." That was my goal, and the kids at school would make fun of me because that was not really a career goal. It was just a weird thing that I was brainwashed with.

James McKinney: Oh, that is awesome. I would love for your sister to still have that sign and just one day, you found it around in the office somewhere. That would be so great.

Alina Vandenberghe: They probably have it somewhere.

James McKinney: So being that was your ambition, did you go to college? Obviously, you're here in the states now so at some point, something brought you here to the states. So what was that next step for you once you were done with high school?

Alina Vandenberghe: So my dad did something quite amazing. Looking back, it was very brave of him. He bought me a computer around the same time I was selling lipstick, and for him that was a huge deal because the price of a computer at that time was the same price of a tractor. And my grandfather was quite upset that my dad spent all this money that he could have bought him a tractor. He was really excited about getting one, and so my dad spent a lot of money on it. He didn't fully understand why he was doing it. He just felt it was the future, so he made me print a tractor, draw a tractor for my grandfather and give it to him. So that's how my foray into IT started and I followed that into college as well. I did a master's in computer science. I really, really liked it. I failed to be a good programmer, but I liked product management and that's how I came here in the US to be an intern in product management.

James McKinney: Was your master's in Romania still or at this point you're in the states?

Alina Vandenberghe: After I finished my master's, I came to the states. I had a little portfolio. I managed to get hired by a company here, Thomson Reuters. It's a media company. That's when the adventure began.

James McKinney: Awesome. So what year was this? What year did you come to the US?

Alina Vandenberghe: 2007, around there it was. Yep.

James McKinney: 2007. You land in the US. I'm going to assume it's similar to a lot of stories that come over here, where they don't have anybody here. They may or may not have already had a job that aligned with them coming here. But never the less, it was probably I'm assuming a solo journey for you?

Alina Vandenberghe: So the reason why I came into the US was because I had met my husband and he was a US citizen, so I had it a bit easier than other people who have to struggle for the visa and all of that part. I hadn't. I didn't have to go through that process. So I was lucky in that regard. When I came to the US, I was not sure what product management was. I wasn't sure what I should be focusing on. But I was really in love with the iPhone at that time. I don't know if you remember, but the iPhone did not have apps. So the concept of an app did not exist. Because when Steve Jobs wanted to have five things on it, and there wasn't such a thing as an app store. But I really fell in love with that, and felt I'm going to focus on it, this is going to be my main area of expertise.

I managed to get a little portfolio working with some startups. I did some mockups. I built some apps that were doing well, but for Android at that time because the iPhone wasn't yet open. That's how I got my first job as an intern at Thomson Reuters. That's when things got a bit interesting, because same time Steve Jobs was preparing the app store. He started doing some apps and he was also preparing the iPad for the launch was immediately after. He would send these people at big companies with he did an iPad that was encased in metal and you weren't supposed to know what's in there. It was in a hidden room with no windows, only one or two people in the company had access. The reason why they would do that is that so when they do a splashy launch, they have some apps on their devices.

So because I was the only one in the company that was doing mobile, I was chosen to work on that secret project. We launched this app that, at that time was quite amazing and revolutionary. Had some stock charts, had video on it, and the video was working really nicely. News articles and again, this was the early, early mobile days. And Steve Jobs decided, even though he did not tell us anything, he didn't say, "Hey, you did well on the app, you didn't do well," he decided to pre-install the app on the iPad, and he also showed it on the stage.

James McKinney: That's awesome.

Alina Vandenberghe: That was my breakthrough in the product management world and realizing that I do have a skill for it, and I got promoted immediately after.

James McKinney: I just want to stop for a second, because one of the things that I think as entrepreneurs we don't do really well, that's kind of celebrate some of the things in our life, but the fact that I'm talking to you, an individual who created one of the very first apps for the iPad, is unbelievable to me. That is such a cool story, and I love that I get to somehow have a connection with you on that. That is so cool.

Alina Vandenberghe: I would have not predicted what a craziness mobile would be, and how things would turn out, and what opportunity would create for so many people around the world, because so many developers these days are earning a good income from it. So many people are depending on their apps to do their jobs or to communicate with others. But at that time, it was the beginning. We were just doing it for fun. We didn't know.

James McKinney: I remember when the app development opened up and people were creating games. I'll never forget, there was a teacher who I can't remember exactly what the game was, but was a super simple game and he was making $1 million a month. It was one he sold for $1 in the app store. He was making $1 million a month on this simple game as a teacher, just because he saw that there was something there and he wanted to create and mess around with it. The early days of the app store just game changing.

Alina Vandenberghe: Yeah, and look it changed our habits. It changed everything.

James McKinney: But at this time, you're an employee with a big media company. You're getting a chance to be on the front line of mobile development. You're product was installed on one of the very first iPads and showcased from the stage by the great Steve Jobs. But you're not working for that media company now. So what was the transition? What started working within you mentally to say, "I don't know if I want to be an employee anymore." What was that next step for you?

Alina Vandenberghe: I was really a bad fit for this corporations. Looking back, I was very rough both in my social skills with others, because I was used to just working and focusing on the results as opposed to trying to understand where everybody's coming from and what everybody is trying to achieve, and what their goals were. I wasn't really used to working as a team. I wasn't ever working like that. I was more of a lone wolf. So at the beginning, I was really rough. I remember my boss would call me a bull in the china town, because I would ruffle feathers. I wouldn't really care that much about what everybody thought. I would just go and get things done.

In order to climb the corporate ladder, you have to ease some of these behaviors and get better at stakeholder management, vertically and horizontally. I got much better at that finally after years and years of working on it. So I did progress in my goal to be the boss. I started being promoted to a director, then as a vice president, then senior vice president. The more I would get fancier title and more zeroes in my salary, the less I liked going to work, to the point where I would have a knot in my stomach. I hated going to work. I didn't understand why I hated it so badly, but I just felt like I did not belong. I did not like it at all.

James McKinney: Do you think part of it was at your core, you're a creator, that's where that bull in a china shop comes from. You have the ability to create something and run at your own pace, so do you think part of that knot was that tension between having to alter who you were to the corporate environment? Because right, a big company has a set way in which things have to get done. Some things are good, some things not so much. And definitely for an entrepreneur, it can be v challenging. But do you think that knot was because of the tension of altering who you are for what needed to take place in the corporate world?

Alina Vandenberghe: There were several reasons, but I think the biggest problem for me was that I would think through what could have been done, and the timeline where that something could have been achieved, and it would just take so long before I would get the budget approved. Or it would take so much time to get everybody on board, and so many meetings, after meeting, after meeting. So much red tape. I remember at some point, I had like five project managers on my particular project and zero work done, just because there was a department that was in charge of putting project managers on my project. It was insane, insane. I had such a hard time with moving so slow.

James McKinney: So what was the actual catalyst for you to say, "All right, I'm done with this."

Alina Vandenberghe: It was mainly my husband who kept nudging me, and he's been nudging and nudging and nudging. Alina, you're much better as an entrepreneur. You'd be so much happier. You'd be moving at a much faster pace. And also, I would get that from my managers all the time. Alina, you'd be much better suited in a startup, not in the corporate world. So eventually, after hearing it from so many people and from so many directions, I said, "I'll give it a shot, why not?"

James McKinney: And what year was that?

Alina Vandenberghe: Three years and a half ago, so quite recent.

James McKinney: So 2015, middle of 2015. So in the middle of 2015, probably toward the end of 2015, did you leave with an idea? What was that first step for you as you entered the entrepreneurial world?

Alina Vandenberghe: At some point in my corporate adventure, I got very close to enterprise tools, so to Oracle, to SAP, to Sales Force. I would see that in these enterprise tools, product talent is more scarce because when someone's very talented to doing a product, they tend to gravitate towards consumer products. It's much easier to understand, it's much easier to get closer to what the consumer wants versus what an enterprise would want. So as a result, many of these enterprise tools are especially SAP as well, they feel very antiquated and very rough. When you go to work and you have to redo something for work, it feels like you just don't want to touch it, something is going to break.

James McKinney: Super clunky.

Alina Vandenberghe: Super clunky, something's going to break. It's even the case with Sales Force, and Sales Force is more… it got prettier. I don't know if you're familiar`` with Lightening interface. It got better, but still not designed to work the way people work. It's designed to be like a data entry of stuff that you have to chase where you're supposed to input things. You click on something then something else happens that you didn't expect. So the user experience and the behavior is not right. So I was frustrated with that and I was in charge of doing some internal projects to fix some of the things for our internal users, and at the same time my husband decided to start his company to help sales people achieve their goals. That website the triggering point. I had the frustration, my husband was trying to solve for it, and I said, "Okay, I'll help."

James McKinney: So was that first solution Chili Piper?

Alina Vandenberghe: Mm-hmm.

James McKinney: Awesome. So that brings us to Chili Piper.

James McKinney: Hey, everybody. I really do hope you love The Startup Story. Did you know that you can actually get paid just for listening to each episode we release? I know it sounds insane, but it's true. There's a free new app called Podcoin and it literally pays you to listen to podcasts. Here's how it works. You listen to podcasts and you earn Podcoin while you listen. Then you turn that podcoin in for gift cards to places like Amazon or Starbucks. Or if you're feeling even more generous, you can donate that podcoin to charity. The more you listen, the more you earn.

So here's what you do. You download the app right now on iPhone or Android and I have a special code for you. Simply use our code "startupstory", one word, "startupstory" and you'll get 300 podcoin just for signing up. And if you listen to enough of The Startup Story within the app, you can get a cappuccino at Starbucks or an Amazon gift card on us, just for listening to me. So go ahead and start listening to The Startup Story on Podcoin and sign up with the code "startupstory." I swear, it'll change the way you listen to podcasts.

Now, let's jump back into our episode.

James McKinney: So Chili Piper, you start working on that in 2016 if we were to timestamp that?

Alina Vandenberghe: Mm-hmm.

James McKinney: Can we unpack for our listeners what Chili Piper is?

Alina Vandenberghe: So we have several products, but the main reason why people come to our website and the reason why they buy our product is because we help a lot with inbound conversion. So when somebody comes to your website and you're a B to B company, you typically have a little button that says, "Contact us now," or, "Talk to our sales team." When you click on that button, you have to fill out a form and then you see, "Thank you, somebody will contact you soon." Now, the problem with that process is that entrepreneurs and CMOs and marketers spend so much time to acquire that traffic to click on that button, and to fill out that form, but they lose those prospects by the time somebody in the sales team contacts them. They lose 70% or sometimes even more of that particular traffic.

What our software does, you insert a little snippet on that form and based on the information that's filled out in the form and some other real time data augmentation, we qualify the products to see if they're not a student, not somebody that's going to waste their time or not going to be a good fit. If they're qualified, we route them to the correct person that should be talking to them based on some rules. Whether it's somebody that already owns that account, an account manager, or a particular team in a specific region, or somebody who matches the size of the company, and we can go round robin in all sorts of directions so that you can talk to them in real time.

James McKinney: Is it a direct hand off?

Alina Vandenberghe: Yep.

James McKinney: Is it an online chat window? Is the handoff done straight phone to phone, like a Twilio? What does that handoff look like?

Alina Vandenberghe: Depends on the companies. Some prefer to just schedule a meeting directly with a person that you're supposed to talk to, and that obviously happens at offline hours. If somebody comes in the weekend, you just say, "Hey, I'm going to talk Monday at 10 a.m. with Joe Black who handles my account." But many companies set up either a call, so a direct call and you connect real time if the rep is available. If not, we do a round robin on some other rules, or can be even a Zoom video.

James McKinney: Now, when you were solving for this in the early days, I'm assuming you were both product design, development, you were doing everything I'm assuming, right?

Alina Vandenberghe: Yes, sales, on boarding, you name it, support.

James McKinney: Everything, yeah. So self funded from the beginning?

Alina Vandenberghe: We had money from our own pocket, about $100,000.

James McKinney: And then obviously seed and Series A. I think I read somewhere actually that your Series A closed a year ago or something like that.

Alina Vandenberghe: Mm-hmm. It's very recent, yeah.

James McKinney: Very recent, and people can find that online. At the time you're creating it, there's already some big players in similar technology. What I find interesting about yours is the handoff piece of it. And one of the things I like to ask entrepreneurs as they enter spaces where there are big players, was there any piece of it as you were developing and growing this, thinking, "I can't pull this off," or were you 100% confident from day one?

Alina Vandenberghe: I stumbled across this problem because a company had asked us to solve it for them. In a different way, they wanted to do this handoff in-between teams, so when the sales guy would close an account, they just wanted to handoff to customer success, and do it real time so that they don't have to say, "Hey, somebody from our team will contact you to onboard you," they would just do it on the call and says, "Tommy will do it for you." When there's hundreds and hundreds of reps, the rules get very complicated. You don't want to lose that momentum, especially for lower ACVs [24:08]. You want to make sure that the volume of deals happens fast. We looked and we looked, because we wanted to help them for a solution, and there wasn't any. You could hack it. You could do Excel spreadsheets, you could try to put some Calendly link together and try to do some rules, but it was just very complicated and it would just take too long for them to do that on the spot. To this day, there's no solution which kind of puzzling that there isn't, but there isn't. Again, there are hacks and ways in which you can try to do it, but there's nothing native. So I did not feel that it's impossible, no.

James McKinney: Okay, okay. How big is the Chili Piper team now?

Alina Vandenberghe: We are 28 and we are fully remote.

James McKinney: All fully distributed, everyone is in a different location?

Alina Vandenberghe: Well, with the exception of me and my cofounder, we're in the same location. There's some other… there are two others that are in the same city, but yeah.

James McKinney: Chili Piper has grown to 28 in a reasonable fast period of time, and fully distributed obviously has its own challenges as well. But when you think back to the first let's say 18 months of Chili Piper, what were some of the significant challenges that you had to face in developing the product, getting it to market, scaling the team?

Alina Vandenberghe: It was really, really hard. I remember working from the time I would wake up until the time I would go to sleep, and I would sleep very little hours. I would not take weekends off. I would not break to do anything. I'm lucky because I do intermittent fasting so I don't need to eat that frequent, but I could feel like I wish I could have somebody who would do this that I would not have to stay such long hours. So that was one.

The second was the uncertainty that we would be able to sustain our bootstrap approach. At any point in time, you don't know if things are going to close or not close, and cash is going to come through or not. So we had some very tough decisions to make. So for instance, something that nobody expected is that we would offer no discount whatsoever. In SASS, that's never heard of and we put this real big on our website. Some people were put off by it, but 99.99% they would just pay the full price and that would be the end of it.

Another weird rule that we had to put in place from the beginning was that you could not use the service until we saw the cash in our bank account, so the promise of sending us money did not count. It was the money in the bank account that would get your work started. So we were a bit rough in that way, but it served us well at the beginning and we had to do it to function properly.

James McKinney: That is awesome. What are the challenges you encounter with having a fully distributed workforce? There's a few founders I've met… Actually, I'll be honest of the 35 founders I've interviewed for The Startup Story, I think one company has a fully distributed workforce. What is the greatest challenge in operating a fully distributed workforce?

Alina Vandenberghe: We did it on purpose. There are two reasons for it. One is because I love travelling and so does my cofounder. We love to be working from anywhere and be able to enjoy what we're doing. Second is because we found that being restricted by geopgraphy to finding talent doesn't feel quite right. You can find amazing talent everywhere in the world, and it just doesn't make sense to be restricted by geographical boundaries.

It forces us to be very, very precise whenever we do something. Everything has to be documented well for the developers to start working, for the product to be designed, for the support materials, for sales people. So everything has to be vv well documented and very well, from an operational stand point of view, everything has to flow correctly. As a result, we employee a lot of tools for that. We have tools for onboarding, tools for training, tools for managing various parts of our business. It takes some effort beforehand, so you do have to spend time to figure out how this process works. But in the long-term, I think it serves us well.

James McKinney: How do you manage culture in a distributed workforce? Because as we're talking, I'm thinking to myself, man, like part, not all of it, but part of what companies think when they think of culture, they think work environment, the water cooler talk. If you're Google, the fully catered lunches. Everyone has a different definition of what culture is, but how do you manage culture in a fully distributed workforce?

Alina Vandenberghe: In a couple of ways. One of them of course is GIFs on Slack, so a lot of GIFS.

James McKinney: Oh, GIFs are the best. That's my love language.

Alina Vandenberghe: So that's one. We also do a lot of Zoom calls, so that keeps us face to face and working together. Always on time on every Zoom call, so everybody knows to show up and then be present. We also have in person meetings maybe once a year, twice a year depending on if they meet our calls or not. Those in person meetings are very unique because they're in places of the world where most of our team members would have not been targeting. We've been to India, we've been to Paris, now we're going to Ibiza. You have some of these people, for instance, even in US who don't even have a passport and they have to get their passports to come and meet the team, and explore different cultures and work together. It creates a beautiful, unifying experience in that you get citizens of the world kind of meeting together and speaking a common language. It's beautiful.

James McKinney: So just as a side bar for all our listeners, I'm sure for those that are a want-repreneurs that are working the 9 to 5 and may have a book full of dreams on entrepreneurial endeavors they want to launch, but they're just not quite sure if they're ready to leave employment yet, Chili Piper is hiring so make sure you go to their site because I'm sure this culture and this distributed workforce sounds super appealing to a lot of people. So make sure you check that out.

But Chili Piper is not your only startup right now, and this will lead to a secondary question. Before we jump into Gipsybot, which is your second startup, one of the things you talked about in the early days of Chili Piper is you wished you had more resources so you weren't working from sun up to sundown. A couple episodes ago, one of the things that one of the episodes that I focused on as I deviated from our founder interviews, we talked about founder depression. Really, it's a topic that doesn't get talked about a lot. But what I've noticed across all, or many of my founder interviews, is just the idea of mental health and how we burrow into this hustle mindset. How did you manage mental health during that period of time? Because that is a very challenging period for an entrepreneur to ensure everything gets done and things keep moving forward, but at the same time you can go crazy and find yourself depressed without even knowing that you have depression. That's where that founder's depression comes in. how did you manage mental health for yourself during that period?

Alina Vandenberghe: I was lucky. I did not get any of that. I did get some burnout at points in time, in that when your servers crash, your biggest client complains and your cash is the way it is, I feel like hiding under a blanket like an ostrich, not come out until everything is solved. I remember we had a period of time for maybe a week or so where our reminders were not sending the way they were supposed to be sending. I felt like this can't be happening, what can I do to get out of it? I did feel like I had some periods where I'd feel the burn out and I just wanted to hide so that nobody emails me, nobody calls me, because it was all my direct number. But those times have long been gone now. We have engineers after engineers that can monitor the servers, and we have 99.9 times so I don't have to sleep with bad dreams or anything. I can even have the luxury to take Saturdays off, which I now do.

I do abide by some very important things that keep me calm. One of them obviously is meditation. I stick to meditating at least 15 minutes if I get the chance a day. If I have the luxury, 30. Since I had a baby that became less. I also do… I take long baths with salt and I take longer walks in nature, so I do take care of that.

James McKinney: Awesome. So now Gipsybot, so now you've added more to your plate which can create its own challenges. But tell us a little bit about Gipsybot as your second startup, that is running concurrently to Chili Piper. So you're still involved in Chili Piper, correct?

Alina Vandenberghe: Mm-hmm.

James McKinney: So tell us about Gipsybot, because then I have questions about how do you manage two startups, but let's just talk about what is Gipsybot?

Alina Vandenberghe: Gipsybot came through a problem that I had at Chili Piper which was managing my priorities correctly. We tried to use Trello to put everybody on the same platform and Asana as well, which stored all my tasks in there, all the team tasks. I also tried to-do lists, I also tried a million other ways to manage my time. A couple of things would happen. People would only look at Trello or Asana to update it once a week when they would remember we had a team meeting or something that needed to be updated, so it would be a stale system of things that I had to do from others, or others had to do for me. Then I had my own personal to do list, which included things like pay bills or whatever other personal things I may have to do. It was not easy to focus. It was not easy to manage the things that I wanted to do, so I decided to start Gipsybot to solve problems for my productivity goals. I envisioned a solution and I said I have to build it, I have to do it. So that's where the little bot was born.

James McKinney: The little bot, I love that. It's so endearing. But so did you create Gipsybot to solve your own problem, or did you immediately say this is probably something that the marketplace needs as well?

Alina Vandenberghe: I asked around and a lot of people had similar issues. One of the main ones was that they would often forget to do things that others asked them to do, or the opposite, they would ask others and those others would forget to deliver on them so they had to do a lot of follow ups. That was one recurring thing that I heard. Another one was I check my email before I do any other things that I'm supposed to do, so essentially my inbox becomes everybody's to do list for me and my priorities are lost. Same with Slack. So we need some sort of attention manager of some kind.

James McKinney: So how long has Gipsybot been in existence?

Alina Vandenberghe: About a year.

James McKinney: So Gipsybot is still, really Chili Piper and Gipsybot are both in a startup stage, right? So Chili Piper, you're still out there, meeting with investors, raising money. Gipsybot, you may or may not have to get to that point depending on how that grows, it's still really new. How do you manage two startups? People are going to be listening right now thinking, "Oh my gosh, I can't even imagine managing two startups." How do you do it?

Alina Vandenberghe: I think part of it is because I'm a sad person and I have no hobbies. I'm kidding. You know, I don't like shopping. I don't like cooking. I don't like any of that. I really enjoy designing product and I do it out of pleasure. It does not feel like work, and as a result it does not feel like a burden.

James McKinney: That is amazing. So let me ask this question, and it is coming a little bit out of left field, but I ask it from the stand point of the non American born founders that I've had on the show. Do you find there to be a difference in the work ethic of American employees or founders, whatever category you want to put into, versus immigrant workers?

Alina Vandenberghe: Yes and no. I observe exceptions in both camps.

James McKinney: Of course, of course.

Alina Vandenberghe: I see that a lot of Americans, they have a lot of grit and a lot of energy to work very, very long hours and do everything that it takes to get things done. The opposite, and I observe immigrants who'd rather have their own free time and not be bothered by working really hard. Obviously, depends on the personality and their nature and their nurture. But obviously, if you're an immigrant you typically are the type of person who left their country, who wants to create probably something better or different futures, so as a result you are more likely to fit the personality of someone who wants to put more hours to achieve that goal.

James McKinney: That is, and I would affirm that sentiment because that is what I've noticed from the immigrant founders that I've had a chance to interview, is just they come here with a perspective of opportunity that I think if you're born and raised here, you don't fully appreciate it.

Alina Vandenberghe: Yeah, but again it really depends on how people have been brought up. Sometimes, just nature and nature is a strange beast.

James McKinney: Yep. So you have Gipsybot, you have Chili Piper. They're both fairly new. What do you see, and let's… which one would you like to talk about more? Want to talk about Chili Piper more or Gipsybot more, because Gipsybot's still in beta, so which one would you like to unpack a little bit more?

Alina Vandenberghe: Well, I'm very attached to both because they're both my babies, and I think they both deserve equal attention. It's like picking favorites between your kids. I think it's hard to even admit that you have a favorite. Chili Piper is more mature. It has many clients, very well known companies and we have processes and operations in place, so from a sharing experience on Chili Piper, that's a bit more mature. On Gipsybot, we're still in the early days.

James McKinney: Where do you see Chili Piper in three years? If we had this recording three years from now, did a "where are they now" episode, and then speak as though it's real right now, where would Chili Piper be in three years?

Alina Vandenberghe: The first thing that I think about is making sure that we create the kind of environment for both our client and for our employees that brings happiness, but not in the happiness of yippee, yay happiness, but more in achieving the results that both parties expect. So for instance, employees mainly come to us because they happen to travel and work from wherever they want, but also they know that they're going to work with A players, and they're going to be challenged mentally. It's really hard to do the kind of products we do. It's interesting. We had to let go, for instance, people that were not A+ but they were A, and it was a really hard conversation to have. You're good, but you're just not making the standards. And as a result, it has created a very interesting environment where if you want to be challenged, you're going to be challenged.

I personally like that and I hope that we can attract the right kind of talent and create the right kind of culture that can make it fun to work. To you know, you wake up in the morning and you don't say, "Oh, I have to do this," it's more, "What am I going to get done today? What can I achieve?" So that's very important for me. The other thing that's important is that we continue to make our customers get this big returns on their investment. In some cases, we bring people six figure improvement in their pipelines. It's very pleasant to feel that you're contributing to their well being. Obviously, the third is making sure that we grow in terms of revenue and get to the point where we can be ready for potentially why not and [inaudible 39:45].

James McKinney: Is part of the culture of Chili Piper to celebrate the wins of the clients as well?

Alina Vandenberghe: That's our main focus. We have a big dashboard in which we observe whether a company is in green or in red or in yellow, and that's the thing that we focus on the most.

James McKinney: That's awesome. So where do you see Gipsybot in three years?

Alina Vandenberghe: With Gipsybot, I really feel that we're getting close to nailing the solution for the time management and attention management. I really hope that we can change the way people work and getting them to achieve their own goals, as opposed to what everybody else asks them to achieve. And get teams productive, so I hope we can get as many teams on it as possible and get as many people productive as possible.

James McKinney: That is awesome. So as our time comes to an end, I want to make sure I ask these questions because these are my favorite questions of our time together, and it's one I ask every founder. The first question is about gratitude. I believe that if we lose sight of all the people that poured into us along our journey, we'll begin to think we got to where we are today by ourselves, and that will isolate ourselves and inevitably lead to our failure. So when you look back at all the people that poured into your journey, who do you look back at with such immense gratitude for what their contribute was to where you are today?

Alina Vandenberghe: So gratitude is a big thing for me. Every night, I have a notebook and I remind myself to feel grateful for at least three things that have happened through the day, and I note them down. If I don't note them down, at least I'm mindful of them. It does change our mindset and allows us to focus on the positive and not on the other things.

I have been very, very, very lucky to have had a dad who had invested the essence of my work right now, which is the computer. My mom was very loving and nurturing, and she always supported me in my dream to be the boss. My sister, she's always been cheering me on from the sidelines. My husband has been my biggest advocate to quit my corporate adventure, so I'm really surrounded by very loving people and I would not be here without them.

James McKinney: That's absolutely right, and I love that. So the last question that I ask, we've been talking to tens of thousands of entrepreneurs, just kind of unpacking your story. One of the things that I love about The Startup Story is I really view it as a digital mentor. So while we've been talking to tens of thousands, right now I'd like you to talk to one entrepreneur. Whatever that vision may be, whether they're an existing entrepreneur who's struggling to get traction and about to call it quits. Maybe it's the entrepreneur who just started and is wanting to hide like an ostrich in the corner, and put themselves on a time out and avoid the world. Or maybe it's the entrepreneur who has been punched in the gut time and time again, and about ready to call it quits. Whoever that is, I would like you to just kind of offer up some words of encouragement and direction and guidance to that singular entrepreneur. What would you say to them?

Alina Vandenberghe: It's hard to get to that point where you've been taken down and you feel that you can't get up anymore. I've been there, so I know how it feels. You feel it in your bones, in your stomach, and every piece body that you have. It's at that moment in time where big things happen. It's either that you realize that you are not meant for it and you should be focusing on maybe helping somebody else achieve their goal, or it's either that a bigger opportunity lies just around the corner, or a completely different thing that can change everything. It's in those hard moments that the big breakthrough comes through.

James McKinney: Hearing stories like Alina's makes me wish that you and I were sitting together when we were listening. I would love to get your key takeaways from her story. It's such a multi dimensional one. For me personally, the takeaway was the perspective she shared on two main points. The first was the perspective she shared about the amount of work that goes into running two startups. At first glance, that just sounds crazy. In fact, she even jokes about how nuts that sounds. But then she shines a light on the fact that we all naturally drift towards things that are a joy for us. For some of us, it's sports, physical activity and maybe even volunteering and serving somewhere. All those things are good and we should be intentional about making time for those things, but they're not necessarily an innate part of who we are.

I always drift towards people. I am energized by being around people, either a group or one on one. It requires zero mental effort to make time for people. For Alina, she loves product development and that is why she's able to operate two startups. It is natural for her to drift towards all that is required to work on her two products. It's not crazy or unbalanced, it's authentic to who she is. In fact, she's incredibly balanced because she's intentional about travel and family. What a great perspective for all of us.

The second takeaway for me was about the value that the really hard times bring for us. She shared at the end of her story that it is in the moments you have been completely knocked down where big things happen, if we stay aware of the moment. If we succumb to the overwhelming nature of the moment and simply curl in a ball, we'll miss out on an incredibly opportunity to learn from that moment. Every little moment reveals a big opportunity. I would love to hear your thoughts on Alina's story, so please comment on any of our posts about this episode on Facebook or Instagram. Even send me a DM about your thoughts. But if you're an overachiever, leave your takeaways in a written review on iTunes. Oh dang, who are my overachievers out there?

Well, I hope you found value in Alina's startup story. And if you've been around The Startup Story for any length of time, then you know how much emphasis I put on the idea that entrepreneurs support other entrepreneurs. So if you have found any value in Alina's startup story, please help give her your input on Gipsybot. It's still in beta and she's looking for feedback, so you can visit gipsybot.com. Once you submit your email, she'll send you a quick survey and based on your answers, she may connect with you directly to get more insight. So let's show up for Alina in a huge way and visit gipsybot.com to provide some input on her newest product. Entrepreneurs support other entrepreneurs, so let's make sure to show up for Alina Vandenberghe in a major way.

And now for my personal ask. The Startup Story community has been so incredible about sharing our podcast with others, but we have more stories to tell and more people to reach. We too are a startup and word of mouth is everything, so please follow us on Facebook and Instagram @TheStartupStory or on Twitter @StartupStory_. If you're on LinkedIn, please search for The Startup Story and follow our company page. LinkedIn is a really powerful way to raise awareness of the show. But the most impactful way you can help us grow our audience is to leave a review on Apple Podcast. Or if you listen to the show via Spotify, then please simply share the podcast directly from your Spotify app or wherever you listen to the show.

These simple actions can make a huge impact in getting these amazing founder stories out to the masses. And please make sure to tag or mention The Startup Story when you do share so that we can connect with you and say thank you directly. I'm so incredibly appreciative of the fact that you listen to the show each and every week, and I look forward to sharing these amazing stories with you every Tuesday with hopes of encouraging and inspiring you to start your story.

If you like this podcast and are thinking of creating your own, consider talking to my producer Danny Ozment. He helps thought leaders, influencers, executives, and authors create, launch, and produce podcasts that grow their business and make a real impact in this world. You can contact him today at emeraldcitypro.com/startupstory.

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September 17 2019
Alina Vandenberghe, founder of Chili Piper & GipsyBot

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