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Josh Kercher of Josh Kercher Bespoke.

The Begin Anyway Series focuses on people who have taken this journey and found success. Most of these people are nowhere near their ultimate destinations. What they have in common is that they have each made a conscious effort to improve their lives by starting over and pursuing a totally different path. We each have a unique journey, vision, and destination; but we all share the desire for a more fulfilling life.

Today we chat with Josh Kercher, founder of Josh Kercher Bespoke.

The idea of ‘Begin Anyway’ has been a motivator for me throughout my professional journey — and my life. Do you have a motto or daily intention that has been inspirational to you?


The reality that we have a very finite time on earth here and that it can end at any moment is an incredibly motivating thing. Especially, if you sit back and really think through the implications of that.

I’ve always wanted to leave my mark on the world and I can’t sit still if I know I haven’t done everything I can to make that happen.

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The beginning sketches of a one-of-a-kind design.

Tell us about your company, Kercher. What do you offer your clients?

The quick answer is that I’m a fashion designer but I really like to think of myself and our company as a storyteller.

We’ve setup the framework of our company in a way that, for some of our products, such as bespoke suiting, we bring our clients into our showroom for a collaborative approach to designing something that will have a very specific use in their lives. In my opinion, one of the most powerful things you can do is understanding how to dress for the room and use style to tell your story.

As we’ve grown and come to understand who we are and our community, we’ve continued to build our offerings based on that understanding.

What started with a singular focus on precise tailoring has turned into designing for the rest of our customers lives. In the next year you’ll see the release of our first full collections including leather jackets, tee shirts, hoodies, denim, outerwear and a few accessories.

As we’ve grown and been able to move into nicer locations we’ve also started to collaborate more with our community and friends and to help as a platform for what we see current culture to be. Our new showroom in Chicago will play host to art installations, small intimate concerts, panel discussions on business and life and the HQ for our new podcast launching soon.

Ultimately, we see our customer as someone who has come into their own and found a way to make a great living with what they do but who understands that the essence of life is continuing to grow. That getting better isn’t filling a bucket, it’s like lighting a flame that burns for eternity. It never ends.

They are well traveled and accepting of all cultures, they appreciate quality over quantity.

It’s that person in the room that you can’t wait to have a conversation with.

Before starting Kercher, and even before pursuing a fashion career what was your career focus? What inspired you to move to Chicago to follow your passion?

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A fashionable work in progress.

Being in the BUSINESS of fashion was never actually on the radar.

I came from a very small town in Michigan where no one does that sort of thing or even talks about it, you know? In fact, I wasn’t sure what I was going to do. I wasn’t the best student coming out of high school so I couldn’t get into the colleges that a few friends were attending but instead I signed up at a local community college to take general education classes and “round out” my knowledge.

That lasted all of 2 months.

I had probably 2 years, after that, of pretending I knew how to make money and knew how to control my life when in reality I was just racking up debt, getting into trouble and partying with my other friends that didn’t go to school.

I probably held close to 15 jobs in those 2 years. Seriously.

Eventually, I snapped out of that stage around 20 or so and found a job in the auto industry which is where I had my first run-in with what it’s like to dress for the room.

The first guy to stick his neck out for me and give me a chance ran a Toyota/Lexus dealership back in Michigan and said he thought I had something but that I looked like shit and needed to clean myself up for the gig. I did it immediately. I mean, literally, I ran to the mall to get a haircut and bought what I thought were dress clothes and came back in 90 minutes and asked, “How’s this?”

He loved me.

Long story short is that what happened to me when I started to dress well changed everything. In my head I was a punk kid who skipped school and couldn’t figure anything out, yet people with wealth, money, families and real lives were coming into this dealership and listening to what I had to say. I saw that clothing alone had the opportunity to change people’s perception of me which, in turn, changed my perception of what I was capable of.

I stayed in that career for quite a few years before getting the itch to jump into real estate after meeting a few very successful agents. I got my license, saved up a little dough and actually started buying and renovating properties with my wife, Holly.

It was after 2 years of doing real estate in Michigan that I felt like I had the confidence to branch out and do something a little bigger. It was then that I decided I wanted to get into clothing design and Chicago was the closest city I could run away to and pretend to be a big boy. So, I did.

That’s quite a journey — a huge testament to where hardwork and commitment to yourself can take you. So after a lot of “grunt work,” you took a leap of faith and ventured out on your own, with much success at that! What were the steps leading up to your #BeginAnyway experience and when did you know that it was time to take that leap?

Actually the thing about my entry into fashion that I still find very interesting and relevant for would-be entrepreneurs is that I started as an owner from the beginning. I truly did not know any other way to do it.

As we discussed earlier, I skipped college which is where they train you to think you always should work for someone else to learn the craft or work your way up, etc. Well, I missed that class altogether so I knew nothing other than simply putting it all on the line and going for it.

Side note: remember this was back when it still WASN’T cool to be an entrepreneur. Family and friends still gave you the side eye for wasting your life away. Oh well.

I’ve always had a “what’s the worst that could happen” type of thought process about this stuff and never really feared what would happen if it didn’t work. I think that has played a major role in any success we’ve had so far. Take the leap. Begin anyway, right?

Plus, even before I made the full leap I actually had reached out to a few companies that I thought were cool at the time and submitted my resume for positions. At this point I had a track record of making money, of making bosses happy and of increasing responsibilities within an organization and I thought well let’s just get a few job offers to make sure I’m sure…


These fucking guys would ace me through the first step or two like a golden child only to have a secretary or gatekeeper then shut the whole thing down because “we noticed that you don’t have a degree and unfortunately that is just a hard requirement for us.”

Are you kidding me? I had met a bunch of recent college grads by this time and almost all of them were idiots. I mean, that’s what I thought to myself in the heat of the moment anyways. I was beside myself.

So there I was, left with no alternative. Win by myself or perish.

The big thing I want people to understand, however, is that none of this happened by accident or overnight.

The first thing that had to happen with me was to first believe in myself. Once that clicks the rest can start to fall into place like dominoes.

The slow 7 or 8 year hustle after that is where you usually lose most people that think they want to be entrepreneurs. Living in basements, not having money for food, going into debt, straining relationships, lawsuits, missing out on social activities. You think you want this but do you really? I think that’s the question not being asked enough.

But if you do. Get started!

Were there any role models, fashion industry leaders or influencers that you followed closely along the way? If so, how did you learn from them?

Not any one from the fashion industry.

Honestly, I’ve been an avid reader for a long time and so pointing to only one or two people is hard for me.

I’m dumbfounded by how many people do not read though. It’s, literally, the best deal out there. Someone’s life work was condensed into a few chapters for you to learn from. It’s incredible!

I’ve always found ways to learn from the people in my life, good and bad. I’ve seen the affects of not believing in yourself or not going after something you’ve wanted and told myself that I would never fall victim to that.

I’ve had a friend pass away from a drug overdose at a very young age and quite a few other friends all but lose their way from drugs so I always said to myself that will never be me.

I’ve had people close to me pay a lot of lip service to the goals they had in life but never actually take any action and I’ve seen over the years the toll that takes on someone.

You can learn just as much, if not more, from the things that don’t go right in life than you can from the things that do.

The mindset of an entrepreneur — believing in yourself when almost no one else does — that positive way of thinking is huge. In my personal ‘Begin Anyway’ experience, changing my mindset and attitude, was vital. Tell me more about how you set your intentions and visualized what you wanted each day on your professional journey. How did this help guide you?

I learned very quickly that a genuine, unwavering belief in yourself far outweighs simply having goals.

Certainly, they go together but you see a lot of people who read that they need to set goals for themselves only to fizzle out a month, week or even day later. They skip the first step of initially believing the idea that they truly can do what they want to do.

There is so much self-doubt and pessimism in the world today, it’s terrible. I know that I will have bad days and I let them come, I embrace them, give them their moment and then they are done.

The other thing I set myself up for is to take massive action and to try to stay as uncomfortable as possible. All of my biggest advances in life were directly on the other side of an uncomfortable action. Unwavering belief combined with massive action is a tried and true recipe.

Also, for what it’s worth, I think people expect too much of the people around them. They want someone else to do the work and being let down is a crushing blow to take. If you don’t expect anything from anyone it’s, impossible to be let down. I mean that in a sense of not making your success or happiness in life predicated on the actions of someone else. It’s your life, do the work.

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Josh Kercher

You are clearly an esteemed entrepreneur who has built significant opportunities for yourself, and I know how much hard work that takes. What advice do you have for other people who might feel overwhelmed by the pressure of Beginning Anyway? In other words, what do you wish you’d known before you took that leap?

First of all, understand that perfect is the enemy of great. You have to just start. That’s SO important to know from the beginning. Otherwise, I think there is one huge thing that took me a very, very long time to learn and appreciate:

To show gratitude.

If you are anything like me, it’s very easy, once you have a little bit of success, to want to keep the pedal to the floor and think to yourself “this is nothing”, and want to keep going. That singular focus can be poison though. You have to make sacrifices and do the work, yes, but you have to find balance in what you are doing and appreciate the things that are happening in your life at that moment.

When you come from humble beginnings, sometimes it’s easy to forget just how far you’ve come. And when you are in a growth stage of your business, it’s easy to not give your family or true friends the love and attention they deserve.

So my advice would be to keep your circle close and show them the affection they deserve. After all, they’ve been with you through the entire journey.

Also, appreciate all of the little wins and progress you are making along the way. Don’t live for tomorrow; live right now. Appreciate every customer that you have that says “yes” to doing business with you because they could’ve said ‘yes’ to a hundred other people and they chose you.

Thank you, Josh. This is great insight and you definitely hit on a few points that really resonate with me. Last question, Who is one person that you would like to have a cocktail with, get to know, and gain inspiration from? And, equally important, what are you drinking?

You know I’m a big believer in answering questions like this with someone that you look up to in your life that is still alive today. The reason is because I think you are creating for yourself an opportunity to actually make it happen. You wouldn’t even believe the list of names that I’ve connected with over the past 10 years out of simply willing and wanting it to happen. People that were so far out of my league it was insane.

With that in mind, I’d love to sit down and have a conversation with Tony Robbins. The level of passion he has maintained for so many years and the amount of people that he has touched with what he does is astounding and incredibly inspirational.

I think being around someone that is consistently executing at such a high level would be an incredible insight into just how hard you could still be working, haha.

My small town roots will always get the best of me as it relates back to choosing a drink. I’m a beer guy so you’d very likely see me keeping it simple.

A huge thank you to Josh for sharing his Begin Anyway story with us. Be sure to check out Josh Kercher Bespoke and all that they do!

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