Chat with an Expert: How to Start Your Own Business – Tips, Insights, and Advice

Interview with Yali Saar, Tailor Brands Co-Founder and CEO

Q. Did you always want to start your own business, or were you not interested in entrepreneurship until you thought of the idea for Tailor?

A. I always had a thing for starting my own projects, but it was never about the need to start my own business as much as it was about ideas that I really wanted to bring to life.

Before Tailor, I started a movement – Raising the Bar – for rebranding education and making it more accessible, and it is still active in the US and Australia today. And before that, I directed music videos and threw parties – but all of these things really started from ideas that I thought were great and wanted to bring to fruition.

With Tailor, however, it was a little bit different; Nadav, Tom and I didn’t really think of Tailor when we first started out.

I think the bottom line for me is not to start something because you want to run a business. Start something because you believe in the idea or the people that you are working with.

You’ll have times that you’ll succeed and times you’ll fail, but in the end, what matters is that you keep pushing – and that’s why you really have to believe in what you’re doing.

Q. How do you write a business plan, and how do you develop a business model?

A. This is a question I asked myself when I first started Tailor, and I actually googled it!

I was so bad at it, at first, that one of our earliest investors had to revise it for me when I first tried to raise money. He told me my plan was so conservative that it “almost seemed like I didn’t want him to invest,” and that I had to show the potential of the product. I was very lucky that he identified the fact that I was just trying to be responsible and sincere, and that he taught me how to package it in a way that also showed the benefits.

I think I got better at it over the years, and I broke it down into a formula that basically has four stages:

  1. User Economics.
  2. User Funnel.
  3. Market Opportunity.
  4. Fact Check – Don’t sell something you don’t believe in, and don’t hope for miracles when it comes to cash flow.

Q. How do you choose the right business name and brand?

A. I have to say that I’m pretty agnostic about naming conventions. I’ve seen terrible names that make great brands and vice versa, but the best strategy to use is to find something memorable.

Memorable names can come in two forms: Catchy names (like Casper, Boeing), or names that capture the essence of what you’re creating. That makes it easier for the mind to store them.

For example, an i”Phone” is obviously a phone; Urban Outfitters is obviously a clothing company. You want to make it easy for a customer to remember you and catalog you in their brain, so your name will be the first to pop when they look for that commodity.

Branding has two main goals: It has to be aesthetic, and it has to suit your brand – but aesthetics are the key factor here. Good branding is branding that helps your customer identify you quickly. It doesn’t have to be super unique.

Dior, Vogue, Harper’s Bazaar are all great brands, and they all use one very similar typeface – yet we can easily identify the fact that they are fashion brands. Branding is really about patterns.

Q. I have a full business plan – now what? How do I start looking for investments?

A. It really depends on you.

The best advice I ever got was that I have to make the right connections with people that can invest, and that proved very true. Investors see hundreds of ideas, and when it comes to seed-stage ideas, they’re really making their bet on a team rather than an idea and a business plan. So if you know an investor, or you can have someone he/she knows vouch for you, that is probably the best way.

However, this wasn’t the case for us. I didn’t come from a tech background, and I literally didn’t know anyone in the space. So I had to cold email people. I wouldn’t say it was necessarily the best approach, but it worked for us.

You have to remember that you’ll be getting a lot of no’s. And that doesn’t mean that your idea is bad. It just means that it might not be fully baked yet, and there are many good ideas out there.

It’s very important to not give up, as at the end of the day, it’s a binary game and not a statistical one: You only need to get one yes. And, although the human tendency is to look at everyone else’s lives through rose-colored glasses, don’t think that the process is any easier for anyone else.

Q. How do you adjust your business to the rapid changes in times and in the market?

A. You always have to re-examine yourself and never be afraid to pivot. When we started Tailor Brands, no one was really thinking about creating automated logos. We were the first ones to use machine learning and AI for that purpose, and the market was pretty dominated by crowdsourced sites.

Today, Tailor dominates roughly 30% of the market and is the fastest-growing platform of its kind. Nowadays, the idea of buying machine-generated logos doesn’t seem far off, and we are currently focusing on being able to do the same thing with branding in general, so we can really democratize the space.

I wake up every morning and ask myself again and again whether or not the decisions I’m making are the right ones. But in the end of the day, you have to focus on what you believe in and continue down that path. Follow your vision. Don’t be blind to the market, but don’t copy, either – some people might be faster or slower, but no one can envision exactly what you have in mind.

Q. What are a few common mistakes you see new entrepreneurs make? Which business-related books would you recommend?

A. I see myself making mistakes all the time – and it’s all right to make mistakes, as long as you learn how to do better the next time.

We all like to showcase success; it makes sense when you need to talk to clients and investors. But no matter how hard you sell, you can’t fake it. You have to focus on what really matters, which is the business itself, and ensuring that the product you’re selling creates value.

Don’t be arrogant and don’t be blind. No matter what you’ve done so far in your life, you always learn from everyone around you.

I think that in terms of books, the ones that inspired me the most are Martin Lindstrom’s “Buyology” and “Brandwashed.”

Q. Let’s talk about the beginning of your journey. How much money did you start out with?  

A. It was really hard. Tom, Nadav and I each put down $25,000 – which was our savings at the time – to launch Tailor, and that’s what we started with – $75,000. It was basically to set up the servers and start doing marketing and get us to the point of the first investment.

Q. How did you decide how much money you needed in each area?

A. When you go to an investor or a bank, you need to understand how much money you actually NEED, and it depends on your business plan.

But when you’re starting out, you have to understand how much you can put in the business, and again, you have to be realistic with yourself. You don’t want to put yourself in a position where, if you lose all that money, you will go under. Because, in the end of the day, half of us fail.

The strength is allowing yourself the opportunity to be able to move forward and start again, so it’s important not to waste everything. TRY, FAIL, REPEAT.

Q. How do I sell my idea to people without sounding like a desperate salesman?

A. You don’t!

You have to believe in what you’re selling. When you try to sell something, you’re basically negotiating a trade with the person who is buying from you. You offer them X, in exchange for their Y – so you need to set your own rules of engagement. Don’t be afraid to walk out of the conversation.

Set the boundary, and say to yourself: If the person is willing to do X, Y, and Z, I’m willing to sell my part and make the trade. The best way to get someone to say yes after they’ve already said no is to be willing to walk away from the table.

Don’t be desperate, and it’ll work – you have to convince people that you have something really worthwhile to offer them. If you’re willing to walk away, then the investor may think they made a mistake.

Q. What keeps you going, given the challenges? How do you choose the right partners to support your business? How do you choose the right employees?

A. The second and third questions answer the first.

The thing that keeps me going are the people around me. If you choose the right people to surround yourself with, those can be your team members – and you want to keep succeeding, not just for yourself, but also for their sakes.  

How to choose the right partners is all about finding people that you believe you want to spend the majority of your time with. It won’t always be the BEST people in that specific moment for what they do – but if you believe they’ll be the best in a week, in two weeks, and you’re willing to walk that journey with them, then you have a much better chance of actually completing that journey.

Over to You

Are you ready to start your business yet?

If you haven’t seen it already, we recommend heading over to the video now and watching the full interview to catch all the helpful tips and inspiring anecdotes that weren’t covered in the recap.

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