Case Study #2: From 0 to 7 Figures in 5 Months - The Try it on AI Story

Key Highlights:

• Shift from clothing to headshots, based on user feedback
• Quick product validation and customer acquisition
• Significant growth from organic, viral content
• Built an efficient, globally distributed team
• Chose quick, informed decisions instead of extensive research
• Provided outstanding customer support and engaged strategically

Here’s our latest Try it on AI interview story, insights from founders Nathan & Adriana.

Hello! Tell us who you are and what’s your backstory.

My life has been a windy road led by my curiosity and strong external forces.  I grew up in Lima, Peru, where I bounced around a lot of schools, often from different social classes.  As an extrovert myself, this cultivated in me an appreciation and skill for understanding other people at a deeper level - putting myself in their shoes and trying to truly connect.  When I was 13, my parents decided to live the American dream and move to the US, where we settled in suburban Colorado. My high school was quite mediocre. No computer science classes and no students attending Ivy League schools other than a few football players. But math and science came easy and because I didn’t speak English well and lived in a homogeneously white American suburbia, I spent the majority of my time voraciously reading about all kinds of science in magazines and the internet.  This led me to attend MIT, where I first studied biology in hopes of someday earning a Nobel Prize. Two years in and I just didn’t feel like I was getting smarter.  Sure, I was learning how our biology works, but I wasn’t learning how to better problem solve - something I could observe in my math and computer science friends.  So I threw away all my life’s plans - incredibly scary to an OCD individual, and switched to computer science, getting a Master's along the way.  Seven internships in six different countries later, I got my first job as a financial quant in Hong Kong, where I worked for three years.  The job was very challenging yet deeply enriching as I got to work with some of the brightest minds I know. 

Now about me as a founder.  I never explicitly visualized myself being a founder, but I did love experimenting and tinkering with technology, often led by my own desire to fix problems I observed around the world.  It’s often the case with good students, however, that perfectionism inhibits their ability to complete their ideas and put them out there for fear of judgment - for fear of disappointing others.  When I met Adriana, I was fascinated by the way she got stuff done AND shamelessly promoted her work. Within two weeks of meeting, I told her an idea for a dropshipping product, and the next day she found the manufacturer, created a website, and ran some ads!  It’s been almost four years and we have been building stuff together since then. I still get a funny feeling in my stomach when I put myself out there, but she’s empowered me to overcome that and try to share more of my ideas with the world.

Fun fact is that, two years ago, before we started Try it on, the Hong Kong COVID lockdowns were taking a toll on my mental health so we quit our jobs and have been traveling the world while working on random projects ever since! We do miss Hong Kong, though, so we may go back soon.

‍Can you give us your 1-3 sentence elevator pitch?

Try it On is an AI photography studio, helping companies and individuals generate studio-quality images. Our software saves people countless hours and thousands of dollars, making it an excellent alternative to traditional photoshoots.  

Our key differentiator is in the quality of our portraits and the creative flexibility our platform offers, making Try it on AI a go-to solution for people who need lots of content for themselves, their teams, or even clients.

What was the moment or situation that sparked the idea for your business?‍

I’ve been studying and applying AI since my college days, so when Stable Diffusion 2.0 came out in November of 2022, I had an almost anxious feeling to stop everything I was doing and work with the technology fully - I truly couldn’t stop thinking about its potential.

So, I convinced Adriana (Adi), my co-founder and life partner, to enter an AI hackathon with me in December.  Since Adi used to be a professional photographer, we built a Chrome extension that allowed people to try on clothes they saw online. Unfortunately, however, the fidelity of the clothes wasn’t yet good enough for companies to pay for this service, but we noticed the facial features were coming out very well!  So we posted some results in a Facebook group and within a week we had 10 people pay us to generate images of them. ‍

How did you test and refine your initial product idea, and were there any significant pivots or changes in direction based on initial feedback or market response?‍

The largest pivot was certainly out of clothing try-ons and into headshots.  It happened rather organically, and because our team was still only Adi and myself, we decided within a couple of minutes. The only negative is that we made our company’s name a momentarily slight misnomer!  However, we’re firm believers that the try-on technology will get there this year, and we’re positioning ourselves as well as we can to capture that technological shift.

The second big pivot was in the curation of the images. At first, we would manually curate every single image to ensure they looked excellent. This proved very unscalable, and thankfully, before the TikTok rush, we started giving people 100 images instead of 25 so they could pick and choose for themselves.

What specific strategies or decisions significantly contributed to the growth and scaling of your business?‍

Having a “Tiktok moment” has been one of the most exhilarating experiences of my life. That viral moment catapulted us into prestigious media publications, which made us rank very highly on search engines.

Can you share some major challenges and how you tackled them?‍

This is my second company with Adi and things have gone very smoothly. We are quick to act and we know where each others’ strengths lie, so we’re good at delegating decision-making when appropriate.  Disagree and commit, as Bezos says.  

On my side, starting and scaling the tech infrastructure was quite a challenge as I’d never done proper software engineering before, barring one software engineering class - the other classes I took were more theoretical. Before Try it on, I’d only ever coded with Python on jupyter notebooks!  But, I knew our first company failed because we outsourced almost all of the software development, so this time around I vowed I would build it all myself.  

So, I joined a dozen or so Slack channels filled with programmers and posted questions there, which helped me navigate this technical journey. Also, shout out to the Modal team on Slack and Supabase’s customer support team on Discord, who helped me with so much more than just using their tech!  Lastly, this would have been nearly impossible without ChatGPT.

‍How did you really get to know your customers and market?‍

I put down my personal email at almost every point of contact we have with customers, and trust me, when they’re dissatisfied they yearn for that email address they can vent to. This has helped us establish quite a few good relationships with customers - customers I still bounce ideas with to this day!

‍What's the story behind your brand and marketing approach?‍

Our brand, and very much our product, was built by focusing on premium quality, convenience, affordability and often overlooked by competitors, usability. We stayed away from using keywords like “innovation” or looking like every other AI startup with a dark and neon-like design. Our early customers were business coaches and healthcare professionals who valued a brand that speaks their language. 

In terms of marketing, we put a lot of energy into ensuring the first 1,000 customers were extremely happy with their results. We hand-held them through the process and helped them understand how our AI works, which resulted in a tonne of organic honest reviews that ultimately led to a viral #AIHeadshots trend across TikTok, IG, and LinkedIn.

Showcasing real success stories from thousands of individuals and media, like WSJ, was the most successful tactic that helped us solidify early on our position as a serious startup with big ambitions. 

Marketing towards businesses from the very start equally helped position ourselves as a market leader within the GenAI space. Our content focuses on communicating benefits to businesses, especially remote teams, and it worked so well that within the first year, we had over 1,000 businesses use our platform ultimately we even worked with one global consultancy on a standalone Teams product that we recently launched. 

In terms of unique strategies, we had three that worked well: 1) found one new cheap channel for acquisition, very handy when the competition was going crazy on our brand keyword on Google; 2) listened to our customers and curated portrait style drops that we knew they’d love.

‍How did you attract and secure your first customers?

‍Fully organic, all from Facebook groups. We posted in about 20 groups until we found the group that really loved it, which ended up being coaches and small business owners. 

‍What's been your approach to product development?

‍Since the very beginning, all of my messages with clients have been extremely personal, trying to understand their intention with using our product.  Because of this, I personally receive a thoughtfully filled-out feedback form at least once a day!  I often reply to these customers within a couple of hours, suggesting ways we can address their concerns. Involving our clients in the product development process is not only crucial in earning trust but also super fun for the clients! Who doesn’t love ideation? 

Once this exchange happens, I often prioritize this change and respond back to the user within a couple more hours once the feature is launched, thanking them for their involvement in our product design process.

‍How have you navigated the financial aspects of your business?

We were profitable within a month and got to 7 figures in revenue within five. 

While we’ve thought about fundraising from VCs, we do enjoy the freedom to take whatever course of action we like, building Try it on with a remote team while traveling the world. Of course, we had to offset the losses we incurred in our previous start-up (almost all of my savings!), so it wasn’t always rainbows.

PS: during my first job I did live quite frugally, saving about 80% of my paycheck each month preparing for a potential day I have to survive on my savings.

‍What future do you envision for your company?

‍We have LOTS of visions for our company as Adi and I are constantly thinking of directions where this could go. We’re also keenly aware of the pace at which AI is advancing, and how we should position ourselves to take advantage of whatever innovation comes in our direction.

One of my favorite visions is to come back full circle into a social experience where you get to try on clothes virtually and post them for your friends to help you shop. Simultaneously, brands will send you catalogs of their new collections with you in them. This will extend beyond fashion - at some point in the future, most companies will help customers visualize themselves acquiring their products, helping them elicit a more emotional response and affiliation to said product. This will make the internet more personalized, social, and more importantly, a lot more fun!

‍Is your team growing? Tell us about the roles you’re looking to fill.

‍We’re not growing at the moment as we’re quite quick and agile as a team of 5, and there’s lots we are working on to improve our efficiency to reach an optimal working state. Once we get there, we may bring a few people on board.   Now, to be frank, the most important characteristic of a potential team member is passion. Passion for their craft, for what we’re building, and for propelling the team forward.  Passion that inspires us to push ourselves to an even higher standard, while educating us and almost convincing us that we should be paying more attention to their passion.   With this, it’s almost a tautology to say that they should be skilled, as skill comes with passion.

‍Where can curious minds find more information about your business?

‍Our site is www.tryitonai.com. You can find me at @ranicket on Twitter, and Adriana at @adriana_lica too. Sadly, I love to write but haven’t had much time to do it recently, so landmanlounge.com is currently out of service.

‍Do you have any reflections or insights you’d like to share with our community?

‍Ah, this one’s tricky because I’m at risk of spitting platitudes, but there’s always someone out there who needs to hear them again so here they go:

• Follow your curiosity and don’t get good or become an expert in something you don’t like doing, or you will likely keep doing that.  Imagine yourself in a panel talking about something you don’t care much about, only because it was a good opportunity at the time and you chased it. 
• The sooner you find good people to work with, the more fun (and easier!) building becomes. Lone wolf stories are the outliers.
• AI has made it extremely easy for people to learn how to overcome almost any obstacle. Put in the time and the results will follow.
• Don’t fall for the Twitter narrative. A lot of people lie, or tell half-truths, just to get clout.  They say things with such conviction that it seems true, which makes you feel bad about yourself.  One of our competitors once posted a chart that showed them at the top of Similarweb traffic for our category. We spent A LOT of money on ads, surpassing that competitor on Similarweb traffic, but we only grew our sales by slightly less than 5% as that traffic didn’t have high intent. So, don’t listen to self-aggrandizing Twitter posts. Just focus on solving your customers’ problems.
• Unless you’re looking to raise capital, never give stuff away for free in hopes of getting revenue in the future. People have lived in a world subsidized by VC money for too long, but don’t listen to them. If your product is valuable enough, they will pay for it. Conversely, if it’s a cute and catchy demo but serves no real purpose other than fun, you may have to find another way to earn revenue, like ads, and you better find that revenue fast.
• You can work with your partner. I love working with mine!
• To wrap it up, the most powerful bit of thought I always tell myself comes from other people giving you advice. 

When you read or take advice, always consider two following:

• What is the person implicitly optimizing for? What is their intended outcome in the grand scheme of things? What is their life’s utility function and does it align with yours? Oftentimes someone will tell you to do something a certain way, but they don’t realize that the outcome you have in mind is different than the outcome they have in mind. 
• Never take advice at face value. What works for one person may not work for another person. I see too many people take advice like it’s a prescription just because something worked for the advice giver.  The problem is the advice-giver doesn’t realize their sample size is tiny and their advice may not travel well. Life is about trying things out until you find out what truly works for you, and then doing that thing until it doesn’t work for you anymore. Then, rinse and repeat. 

We'd love to see your journey in pictures and videos.

Dec 16: we started building and tinkering in the AI space.

Dec ‘22: Our MVP was focused on trying on fashion outfits, hence Try it on! 

Jan ‘23: One of the first few AI Headshots customers! 

 Feb ‘23: huge hit within a large healthcare community, our first viral peak. We had to hire 4 freelancers in Mexico City to help us manually curate headshots, as we weren’t yet fully automated!

Mar ‘23: second viral peak (big one) blowing up across US, CA & UK - servers crashing!

May ‘23: WSJ hosts a live AI Photobooth and people love their results.