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“Developing an Eagle Eye Perspective” The 5 Lessons I Learned Being a 20-Something Founder

I had the pleasure of interviewing Syed Obaid. Syed is the CEO and Co-Founder of The Jacket Maker, a one-of-a-kind startup, combining…


I had the pleasure of interviewing Syed Obaid. Syed is the CEO and Co-Founder of The Jacket Maker, a one-of-a-kind startup, combining old-world bespoke tailoring with e-commerce to make finest quality custom & ready-to-wear leather jackets.

Aiming to simplify personalization in fashion industry, The Jacket Maker has received over 20,000 custom order requests and served over 10,000 customers in more than 50 countries across the globe.

Their idea is based on the belief that everyone should own a jacket that they truly desire, with the design they want, color they prefer, and details they love.


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

Right after graduating, I started my career with Rocket Internet, one of world’s biggest e-commerce incubators.

In my four years at Rocket, where I spent most of my time in online marketing, I explored the true potential of e-commerce.

At the same time, I had keen interest in other departments and I always had ideas as to how we could improve customer support, bring innovation in sourcing and more.

Obviously, I couldn’t have those directed and implemented so I decided to give the ideas in my head a chance and this is where The Jacket Maker was born.

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

There is something amazing about wearing a product that is specially made for you, and just for you.

The fact that, what we do enables people to discover and express themselves in terms of what they wear.

We have heard about custom shirts and suiting, but we are one-of-a-kind initiative catering to leather outerwear category.

Jean: Are you working on any exciting projects now?

We are creating an online tool through which people would be able to create their own designs for leather jackets. This would automate the existing design consultancy part that we already have.

At the same time, we still want to keep the personalized human support process so we don’t lose the bespoke essence. There would be a final review by one of our design consultants before the order is processed.

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

“Delivering happiness” by Tony Hsieh has made an enormous impact on how I approach business. It taught me not to get too focused on technicalities and focus on the basics of creating value.

It taught me that e-commerce is just another point of sale; the main principles of business and marketing remains the same. You have to be obsessed with creating value for the customers and it remains constant for both brick and mortar and e-commerce.


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

1- Difference in roadmap for VC Funded Company Vs Bootstrap Business

Before The Jacket Maker, I was the Channel Marketing Manager at a VC funded company. We achieved exponential growth by primarily using paid marketing with a huge budget.

I developed this bias that the best way to growth for an e-commerce business is through paid marketing. I implemented the same thinking at The Jacket Maker and didn’t focus on other marketing channels to an extent I should have.

What I learned is that the growth paths of a VC funded company and the business you are trying to bootstrap are very different. My advice to entrepreneurs is to leave your biases of your past jobs and experiences when you are starting an entrepreneurial journey.

2- Developing an Eagle Eye Perspective

When I started, there were some months when I was working day and night only to crack marketing campaigns.

Other months, I was only obsessed with improving User Interface of the website and in the process I would compromise on some very critical points that deserved more attention.

It took me some years to sketch a clear broader view of the critical points that dictates the success of our business. They are:

A. Great Story: This is the starting point, everything else follows. You have to come up with a compelling story, as to why people would care about you and your product offering.

B. Great Products: Based on your story, you have to create great products. What are great products? Which are totally in sync with your philosophy and provide exceptional value.

C. Great Content: Even if you have a great story and great products, how do you communicate that to your target audience? You would need to create great content that promotes your brand. When I say content, I’m referring to everything audio, visual, textual. Anything you are using to communicate to your customers.

D. Great Coverage: You have a great story, products that provide value and content to market your product, but how do you get people to see your products. The integral point to understand here is that coverage comes at a cost.

After sketching this broader view, I could see that marketing campaigns falls within “Great Coverage” and if we are not creating enough “Great Content” the problem lies in preceding step. This helps to achieve balance in the defining points of your business but also help you to pin point where you need to invest your resources.

3- Importance of Managing Cashflow

Managing cashflow is as important as any of your other strategic objectives. Simply put, if you run out of cash, you can’t operate to achieve any of your strategic objectives.

4- Getting multiple things right

Before starting, I understood e-commerce and digital marketing inside out. What I realized later is that it is not skills in e-commerce alone that comprise the recipe of a successful online business.

There are multiple things you need to get absolutely right in parallel to be successful, which in our case, are the four-point critical points I shared above.

5- Response to Crisis

In the world of startup, no matter how thoroughly you plan and how vigilantly you execute, there will be things going wrong. Developing the skill to respond to crisis, becomes as important as mapping your roadmap. It would have really helped me if somebody had told me to always have contingent plans ready.

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. 🙂

I would love to meet Roger Federer and exchange thoughts about what keeps him going. Why I’d like to meet him? — ’cause he’s the greatest!

— Published on June 27, 2018

Originally published at medium.com

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