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10 Questions with John Machacek: Tailorie

John Machacek, Chief Innovation Officer for the Greater Fargo Moorhead Economic Development Corporation, has worked with countless startups throughout our community over the past nine years. He knows their ups, and their downs, but most of all, he knows the questions to ask them. Here are John Machacek’s 10 questions for Brianne Osowski, Founder & CEO of Tailorie.

1. Will you please tell us your Tailorie elevator pitch?

You can think of Tailorie like a dating app for brands and consumers. Tailorie matches you with brands that align with your interests, and if the match is mutual, instead of a first date, you may be selected to receive a gifted product from the brand. Within the Tailorie app, you’ll also find an authentic community of consumers sharing recommendations for their favorite products and brands.

2. How did the concept for Tailorie come about for you?

There were a series of “aha!” moments I had while I was running my retail store Curious. Individually, they weren’t significant, but when I put them all together, Tailorie was born.

Knowing the story behind the brand, which I most often learned when meeting the brands at the market, makes it much easier to sell the product. In addition, I began to see the desire for connection within consumerism.

When I sourced new brands for my store, I was amazed by the number of brands I was exposed to—most of which I hadn’t heard of before—and as a retail buyer, it was my job to discover brands. I had tools to discover brands that consumers don’t: wholesale markets, direct catalog mailings, industry newsletters, email solicitations, brand reps, browsing other shops across the country, samples, etc. Not once did I discover a new brand through a social media ad. So, I began to ask myself why this was the case.

During this time, I had recently relocated back to the Midwest from New York. The ads I saw baffled me, so I dug into my data profiles on Google and Meta, and the picture that my data painted of me did not align with who I was, which was pre-iOS 14. So, I began to ask myself, how could consumers lend their voices to their data?

I was burning out on the constant battle called social media marketing. As a small business owner, the task fell on my lap, and the rhetoric around the subject was… “post daily, be consistent, three times a day is best, post across multiple platforms” – which translated “to do more things, be more places, etc.”

As I faced these issues and started asking myself questions, the idea for Tailorie became clear.

03. You have a two-sided marketplace in that your customers are the companies selling their products, but your main users are the consumers. What approach have you used to engage with both sides of this market?

From the beginning, we set out to build an environment that created value for our brand partners and community members. Doing so meant we needed to solve two different problems, one for each side.

We began on the brand side of the equation. I had personally experienced the struggles of reaching consumers digitally to increase awareness and connect with an audience. Therefore, I knew their pain points and could speak to them from a perspective they understood and felt. These initial conversations helped validate that the problem wasn’t just one I had, but thousands of other emerging brands also had. They were ready for and open to an alternative solution. We then moved to the consumer side; this was a bit more difficult, mainly because the problem we ultimately solved was one that is felt and not typically verbalized. Therefore, we dug deep into fundamental human needs and consumer psychology to understand and validate the problem.

That’s a long way of saying this is how we landed on Canvas Crates, which is the feature in the app that allows us to deliver equal value on both sides of the equation.

What is Tailorie?

Tailorie is an app designed to give authentic brand and product recommendations that are tailored to the individual user.

04. I’ve been using your app since the beta stage, and can definitely see the two-sided engagement as well, with not only having companies share information about their products, but so much of it is users posting videos and pics evangelizing products. The new Canvas Crates feature is really cool where you may get matched with a new product, based on your interests, and you have the opportunity to have the product shipped for free to test it out. At first, I thought, this is too good to be true. Have you experienced that surprise with other users too, wondering, what’s the catch?

Yes! We are asked that question often. In an era of extraction, as I like to call it, society, as a whole, struggles with trust. When you think about digital advertising as an industry, the goal is to gain something from the consumer whether that be their attention, time, data, or dollars—but what does the consumer receive in return? At Tailorie, we believe that consumers’ attention in any form is a privilege, not a right. It’s why we are an ad-free platform. Instead of selling the eyeballs of our community in exchange for ad dollars, we do something entirely different. We require our brand partners to “pay” their Tailorie membership fee by investing products in the community. For a brand to be introduced to the Tailorie community, we require them to lead with value in exchange for consumer attention. Thus, for consumers, this initially feels like an incredibly foreign experience. If a brand gives me something for free, there must be a catch. Instead of a catch, we instead offer a reminder—your attention and purchasing power are not free commodities. It’s something of incredible value, and at Tailorie, we not only recognize that, we honor it.

05. Speaking of beta versions, from being a beta user of it myself, some things I noticed were that: you care a lot about the design and aesthetics, as it looks great and I could see the continual enhancements; you used TestFlight for the testing platform; and you were in beta for a fair amount of time. Can you share any of your strategies or process for readers who may be curious about app testing and launches?

When building Tailorie, I spent much time thinking about how I wanted users to feel when interacting with the platform. I leaned into design and aesthetics because they are phenomenal tools to use when the desired outcome is to create a feeling for users within the experience. What can I say, art moves people.

Our strategy with beta was to open the platform to a few thousand brands and consumers while we were still building, iterating, and trying to determine what would lead us to product-market fit so that we could make data-driven decisions to fine-tune the product. Beta was important because it allowed us to see how consumers were using the platform, where they were spending their time, what friction points were driving them to disengage, etc. Understanding the problem you are solving is one thing; creating a solution that delivers the desired outcomes is an entirely different story, primarily when the solution’s success is hinged upon active participation and engagement from two audiences in a community setting. Although the theory checked out, there was no way to honestly know if the product we built would deliver a viable solution until we allowed people to use the product. Once they began using the product, we made continuous iterations and pivots until we landed where the key performance indicators demonstrated that the solution was viable.

Through this process, we did a few things right. As a result, Tailorie ranks in the top 20% of all Social Media apps in the Apple app store for user retention and ranks in the highest tier of apps for total download volume.

06. Since we’re talking technical stuff, will you please tell me about your experience being a non-technical founder?

If you want to start a tech company and you are not technical, do not Google non-technical tech founders. It nearly convinced me that I had no business starting a tech company. Even though I ignored the advice, I felt like I was wearing some forbidden badge in the early days.

My perspective has now changed significantly. I founded Tailorie because I conceptualized a solution to a problem that I knew intimately. The solution to the problem happens to be delivered through a technical vehicle. Think about it this way: do we expect fashion designers to know how to manufacture the fabrics they use in their designs? Do we expect a builder to build us a house without any specifications? I now see tech in the same way. I may not write the code that brings Tailorie to life on your phone, but I do write the logic and functional requirements upon which all the technology is built.

The most helpful thing one can do is be okay and open with what you don’t know. When I started this journey, I didn’t know much about what was required to build a tech product, but I made it a priority to learn along the way. A simple way to start was by attending the daily engineering meetings. It exposed me to the technical language they spoke, the way they thought, and how that would ultimately deliver our solution to the world.

We need to normalize the notion that one must not be technical to start a tech company

07. You’re obviously doing something right as you communicate the company vision and capabilities, as you’ve developed a beautiful app, you continue to gain traction in that two-sided market we talked about, and you have been successful in raising funds. What have you learned about effectively pitching your company?

Why, thank you!

Focus on the why and the who—don’t get caught in the weeds of the what and the how.

The why moved me to jump off a cliff and start this company. The why inspires me to charge ahead when the company’s challenges feel impossible. The why forces me to focus on the problem we are solving and thus reminds me to pivot if something isn’t working.

It’s easy to get caught up in the WHAT and the HOW when pitching. That whole non-technical technical founder thing got me so caught up in the what and how—as a mechanism to overcompensate for my non-existent tech background—that in my first few pitches, I failed to focus on the why. Let’s say those pitches didn’t go as well. We see it all the time in advertising too. Ads so often tell you WHAT the benefits or solution is and HOW the product is different… and we quickly forget what we were just told. We rarely hear the WHY or the story of the WHO behind the product, but those are the points that are important in both pitching and advertising because they are the two things we, as people, can relate to, connect with, or believe in.

Humans are wired for connection, so I advise sharing stories that people can connect to.

Finally, for me, authenticity was key. I refused to show up as anything other than my truest, most imperfect self.

08. What have been some of the biggest surprises for you in the process?

How much I enjoy system architecture and backend development. Who would have known? It’s both creative and systematic; thus, it speaks to both my brain’s creative and logical parts. If I had known this earlier, I might have pursued a different degree and career!

Startups give you the opportunity to learn as fast as you can swim. I have an insatiable desire for knowledge and am grateful to be in such an environment. I’ve also learned that the environment is not for everyone, which is okay, too.

09. If you could go back in time to Brianne from several years ago, what hindsight advice would you give yourself?

The only answers you truly need are those that live deep inside you. Spend more time there.

10. Lastly, what can we do as a community to help Tailorie succeed?

If you haven’t already, download the Tailorie app and give us a try. If you love it, we’d be grateful if you’d help us spread the word by sharing Tailorie with your networks. If you don’t love it, email us, and let us know why. Our goal is to grow in all ways continually, and those are two ways to help us do so.

Tiktok: @tailorie
Instagram: @tailorie
Facebook: /tailorieapp
Twitter: @tailorieapp

Written by John Machacek

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