This Professional Model Turned Tech CEO Is Building The Easy Version Of Quickbooks For Freelancers

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Jessica Perez, Costa Rican born, professional model and now also fintech CEO has been building Tycoon, the job tracking app for freelancers, since the beginning of 2016.

Even with counting Victoria’s Secret and Sports Illustrated among her clients as a model, Perez struggled with the same challenges that so many freelancers face: keeping track of all her jobs, money owed her and managing her overall finances to pay the people she worked with, herself, and taxes.

Perez has been building the app without VC backing and has gotten to 16,000 downloads with no marketing budget.

We sat down for a conversation in which Perez spoke frankly about her strategy for growth, her struggles with fundraising, her experience of feeling like she was living out her dream yet felt unhappy--and more.

Below is a condensed version of our conversation.

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What made you start Tycoon?

It was maybe a little over a decade ago when I started thinking about creating something like Tycoon. I wasn't really sure at that time that it was going to end up being what it is now. But I knew that I wanted to create something that made it easy for freelancers like me to keep track of income and what payments were yet to come in.

One of the reasons that this was really important is that in the fashion industry you often have payment terms of 30 days or longer. For models, it can sometimes be up to a year where you're just sitting there waiting for a client to pay you.

What ended up happening to me is that the more I traveled and the more I worked, the more I lost track of the people who owed me money. At the end of one year, I had over one hundred thousand dollars due to me but I didn't have enough cash in my bank account to buy the Christmas gifts I wanted. I was really irritated by that not only because I felt broke when I wasn’t, but also because I felt somewhat responsible for it, for not having put more pressure on people to pay me on time.

I had my accountant teach me how to use Quickbooks but it really wasn’t user-friendly. I tried recommending it to many people in my industry and the response wasn’t great. Most people thought that I had become an accountant to be able to use it.

It became very apparent to me that something needed to exist that made it really easy for any freelancer to enter their income, put down payment terms and then be reminded of when to follow up for payment.

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You said when you first got started you didn't really know that this was going to be what is it is. Can you say more about that?

When I first started thinking about doing this I was still using physical CDs for software! So I was thinking about a CD type software. Obviously, as apps started to come out, that idea became obsolete. The other idea, which we may still do in the future, was to make this a web-based site to log into and manage from a computer. I also at one point thought about maybe starting a financial management agency where we’d use existing software and then help people better track and better manage their money as a service.

Ultimately, I felt like an app would be the easiest for people and most relevant.

When we started to build the app I was inspired by these paper booklets I used in my very early days of modeling. They were these booklets given to us by our agencies, they called them vouchers. They had fields for a client name, date, a timeframe, a total amount for the job and then a signature box.

I created a system where when I would receive a paycheck from my agency, I would go to my voucher book and check off the job that had been paid. This would help me know which payments were still outstanding.

When the modeling industry entered into the digital era, these booklets became obsolete but nothing was developed to replace them. I think if you mentioned vouchers to a model starting out today they would be like, “What the heck are you talking about?”

The idea for how to approach building the app came from me thinking about how simple and effective these little notebooks were and how to create that for these new, young models and other freelancers. What would their notebook be? That is Tycoon.

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What’s your strategy for growth?

I oscillate from thinking that I'm strategizing in a really smart, innovative way to thinking I'm doing it in the dumbest, most ignorant way that’s never going to work.

Most tech companies raise a little money, build an MVP, get their first couple hundred users and then go out and raise one to three million dollars. Then they try to take over an entire market and blow out their competition.

I didn't go out and raise a million dollars simply because I couldn't. But I thought if I keep my burn rate very low and stretch the $250,000 of private money I raised and my own savings, I could still make a product where I generate organic growth in my own growth hacky, just-a-hustler kind of way, and eventually get to those tens of thousands of people, just more slowly than if I had three million dollars.

Currently, I keep my burn rate low by not paying myself a salary, only paying for the bare minimum of what I crucially need at any given time, and by having met and motivated many wonderful people who donate their time, help, and even office space, to help me get ahead.

Last year we were able to get from 1,000 to 16,000 downloads. Currently, it'll take me a thousand of those people to pay me for the premium version of the product for me to be able to at least pay for the maintenance of the technology.

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How did you get to your first 1,000 downloads?

Perez: Getting to the first 1,000 downloads was a nightmare. It took us about a year and a half. But there are a lot of ways that you can drive growth in the beginning when you don’t have money. The first thing I ever did was show up to modeling jobs and talk to everyone I possibly could about my app and why they should download it. Recently I met a model at a birthday party who loves Tycoon and when I asked her how she had heard of it, her response was, “You told me about it at a job.” All I could think was, “that sounds about right.”

But if you don’t have access to your target audience (which by the way, makes everything that much more difficult) the way to drive growth is to do it with the product itself. Create a good product that people both need and want to share. If they don’t see the use for it right away, they never will. Another way is to provide them with an easy way within the product itself to share it with other people.

Developing a unique voice for the brand I feel has also made people want to stand behind our brand. There is no Oz behind the curtain, so to speak, when it comes to tech products. Who are the people behind the tech? I think this in particular is something that a lot of tech people don’t invest enough time in thinking about. People are driven to support brands, not just products. Our branding has been strong from the get-go because I had a very clear vision for it from the start.

We also threw events and created a newsletter with a quirky voice to impart a sense of community. People who know me well know I don’t take myself too seriously. With the topic of finance, I think it's especially important to not have a serious tone in messaging because of the snoozefest and intimidating quality of it. There’s a big difference between being serious and professional, the latter being important because it yields trust and that’s highly important in the world of finance. You can still be professional and have a fun tone and voice in your messaging.

Another thing that we did to help with growth was to create partnerships. We cross blogged with a lot of partners, mainly companies we had identified as having our same target audience but having a different ‘sell’ than us. I met a lot of people face to face who liked me and wanted to help me. I never turned down a meeting with a potential partner, whether they had less users than us or whether they were so ahead of us that I thought I might not have something to offer them. I learned how to leverage both groups appropriately and create value propositions for each. For example, some companies who had less users had raised more money than us, so we got them to pay for the prize of a sweepstakes while I brought in a partner with a much larger following to team up with us. The partner with the larger following was interested in reaching our specific community so we all got something out of it.

Once our numbers grew to 1,000, they grew from that to 5,000 pretty quickly. I’m guessing because once you reach thousands, organic growth becomes much more significant.

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You said you were unable to successfully fundraise. Would you say more about that?

Other than not being a white man from an Ivy League college and not having an MBA, I am also not a technical founder and I don’t have a co-founder. Not having a co-founder drew a lot of questions from investors about my ability to build this. It’s not like I didn’t try to find a co-founder. It was just that when I realized I that I really needed one for fundraising, I already had an MVP of the product for close to a year. It’s really hard for someone to look at something that has already kind of taken off in its own little way and feel like they can come in and put their own equal amount of input into it.

I would tell investors “if I have money I will be able to find a good technical partner. But I need to be able to pay them. The people I have met are asking for paychecks.” And then investors would tell me, "well, find the technical founder first and then we'll give you the money." It was a catch twenty-two: I needed the technical co-founder to raise money but I needed the money to get the technical co-founder.

There was that, and there were a lot of mansplanations too. I’d meet with investors who had never freelanced a day in their lives who’d sit there and explain to me what “the issue really was” for the freelance audience. But there was only one of us at the table who had been a freelancer for 15 years and whose friends were freelancers, and that was me.

Then there were the times I’d get asked by investors to do a follow-up meeting and realize that I was inadvertently on a date with them.

It honestly became such a disheartening experience for me.

I decided to stick with finding smaller batches of private and friends and family money, use my own savings, really focus on the product and build more slowly than I would if I had a bigger amount of outside capital.  

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What's one of the biggest personal growth lessons you learned since starting Tycoon?

At the end of last year I took a one month break and went to Thailand to literally Eat Pray Love it for a month. I needed to step away from Tycoon to gain some perspective about what it was that I was doing and what I thought I needed to do next.

One of the first things that I talked about in a group self-development class was how I was trying to figure out how it was that I had reached a point in my life where I was doing exactly what I wanted to be doing, yet I felt miserable doing it.

I think a lot of the time founders, we have this issue of being scared to fail, being scared to succeed, being scared to stagnate, being scared to grow. And that’s where I was at.

I realized there had been so much fear attached to everything that I was doing and so many of the choices I made. I had either let fear lead me into something or I didn’t do something because I was feeling too much fear. Fear had been the leader of my thought process.

I thought, “If I lead this company with a fearless point of view, what will I come up with?”

Instead of focusing on things like growth, I’ve realized I need to focus on my own happiness. I need to think about what it is that I want to be able to do with Tycoon. What positive change can I help make with our company? Ultimately, I think the best thing for Tycoon will come from that.

 

This article was originally published on Forbes.com

 
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