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“Be Thankful” The 5 Lessons I Learned Being a 20-Something Founder

I had the pleasure of interviewing Yali Saar, CEO and cofounder of Tailor Brands. As the world’s first automated branding company, Tailor…


I had the pleasure of interviewing Yali Saar, CEO and cofounder of Tailor Brands. As the world’s first automated branding company, Tailor Brands is revolutionizing the branding services industry by teaching computers how to design logos, write copy and even plan strategy. They serve over 6M businesses across the world and recently closed another $15.5M in funding.


Jean: Thank you so much for doing this with us! What is your “backstory” of how you become a founder?

Thank you for having me! I’ve had quite a diverse background, starting out as a journalist and an activist. I started doing creative work for advertising agencies and that’s where my journey into the branding world began. Eventually, I helped to found an educational branding nonprofit called Raising the Bar, which quickly grew to over 100 people and across multiple cities around the world. As the nonprofit took off, I decided to move on and with two of my closest friends and start Tailor Brands with the mission to give access to great branding services to all.

Jean: What do you think makes your company stand out? Can you share a story?

We had a handmade soap maker from South Dakota using the platform. He was really good at what he did but regardless of how hard he tried, he wasn’t growing. He had interested buyers but they wanted to see he has a financial backbone before they made an order. He went to the bank and they told them they can’t approve a loan because his business doesn’t look “real” enough. It was a completely legit business but he wasn’t able to sell it as such. Using Tailor, he started creating business cards, letterheads, a landing page and even banners for his roadshows. He got the loan, the buyers, and managed to finally grow. Good branding is a powerful weapon, and we often forget it is only available to a selected few. Tailor Brands changed that. This maker is one of 500,000 new dreams that get to turn into a reality every month with the help of Tailor Brands. Tailor Brands is the only automated branding service on the market. We are working to democratize the creative industry, giving access to these services for a fraction of the cost to anybody, whether a niche project or large business. With 6,000,000 clients and counting, our AI technology is constantly learning and improving. Just answer a few questions through our website and we will provide you with logo options to start you off using Tailor Brands. From there, we have subscription options that outline the scope of Tailor Brands machine learning to develop your brand. Not only that but we are a tech company of 60% women.

Jean: Are you working on any exciting projects now?

We have exciting new projects in store at Tailor Brands. From integrating new services into our platform to expanding globally, the team is growing and developing new unique ideas to help our customers create the best brand image that our services can possibly provide.

Jean: Do you have a favorite book that made a deep impact on your life? Can you share a story?

Count of Monte Cristo really geared a large portion of my life. Not so much for the revenge part but rather for our ability to achieve the impossible and the dangers of forgetting what’s important. As most probably know, Count of Monte Cristo tells the story of Edmond Dantes, a poor sailor that is set on the road to success only to be betrayed by his colleagues and lose everything he had. He manages to survive prison, amass a great fortune and win the love of his life again. The funny thing was that as a child I always felt that Dantes had so many chances of getting his life back sooner if he only focused on what he wanted to gain rather than what he wanted others to lose. As I grew up, I realized any road in life is usually much longer than a 10 year old could grasp but I was left with the belief that you should always focus on being the best rather than trying to beat anyone else. You are only competing with yourself, with being the best version of yourself that there is. We often tend to overlook how fortunate we are, and no grudge is worth sacrificing all that for.


Jean: What are your “5 Lessons I Learned as a Twentysomething Founder” and why? Please share a story or example for each.

1 – “Not everything that is faced can be changed, but nothing can be changed until it is faced.” ― James Baldwin

This sentence is something my mother clipped from an article and put on my table when I was around 16 and it really summarizes the way my family looks at life. I’m an undying optimist, but not unrealistic. I will happily face any problem, the fact no one solved it before doesn’t make it unsolvable. At the same breath I know my powers are limited. Sometimes it takes a different combination of people, a different timing in life, to solve something. It’s alright to fail. You can always get back and try solving it later..

2 – Try. Fail. Repeat.

This sentence serves as my father’s extension to the James Baldwin sentence. It basically means that success is not statistically measured. It’s binary. And for that reason it’s ok to fail as long as you get up and keep on going. It reminds me of every funding experience anybody ever told me about. We all get no’s, but they don’t matter when you get a yes. Don’t give up, and don’t ponder too much, we all fail, it’s more important to make sure we get back up quickly.

3 – I know nothing. And neither do you.

Working in a truly innovative field is funny because in many cases your experience doesn’t count for anything. When we were just starting out Tailor Brands we met with a very prominent CEO of a publicly traded company for advice. He sat with us and said something that sticked since; “Listen, I have a lot of experience in this and I think you should do X, but remember that I never did exactly what you are doing so you might be better off doing Y. I don’t really know and no one else will”. We tend to test a lot at Tailor Brands, campaigns, product feathers. After hundreds of tests you learn that regardless of how keen your intuitions are you don’t really know anything. If anybody in the company wants to test something, regardless of how faintly you believe in their idea, let them. They might be making a mistake, but so might you.

4 – Work like your life depends on it (And then remember it doesn’t)

When tackling impossible tasks you should always be willing to go to the extreme, work around the clock, lose yourself to anything but the task at hand. You may have to fight as if your life depends on it, but the trick is to remind yourself that it doesn’t and find the balance between crunch time and down time.

5 – Be thankful.

After all, remember that our problems are not the end of the world. Regardless of how badly we might fail, we have a chance to pick ourselves up and try again. Keeping things in perspective and remembering to thank the friends and family that have helped along the way will make you smile while you try again.

Jean: Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

There are too many for me to count 🙂 So I’ll use the platform to say I’m always open for having breakfasts and lunches. Just reach out. Food is important and so are new inspiring ideas.

— Published on June 27, 2018

Originally published at medium.com

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