5 Lessons for Aspiring Entrepreneurs

Posted on June 26, 2013 by Jesse Schiller | 10 comments

We’ve been heading down this entrepreneurship track for a little over 3 years. In that time, we’ve learnt more than I could possibly quantify. It has changed our lives in every possible way, almost unequivocally for the better. But along the journey, we’ve learnt a lot of hard lessons, many of which cost a lot of money.

For all those with aspirations to transition your dreams to reality, and those that are already on the path, here is a list of the top 5 lessons we’ve learnt along the way that are integral to growing a healthy, strong and successful business.

LESSON ONE: Simple is Hard Enough

KOOSHOO was still just a flicker in our eyes when we met Damien, the founder of Native Shoes, a game-changing shoe company (think Crocs, but cool) based out of Vancouver. At the time of our meeting, Native was early in a remarkable trajectory towards worldwide acclaim.

Damien agreed to meet with us thanks to a mutual friend to field some questions about what it takes to start a successful brand. We met in their “offices”, a 70’s era split level home in a residential neighborhood of West Vancouver where the bedrooms act as offices, and the main meeting area was a living room replete with 70’s furniture.

We covered a great deal in that meeting though one piece of advice came up over and over again as we discussed everything from financial planning to sourcing to product development: SIMPLE IS HARD ENOUGH.

We didn’t know it then but over the years since that meeting, “simple is hard enough” has become a go-to mantra anytime we get to a fork in the road.

This may come as a surprise to some, but we began this entrepreneurial journey with the idea of making beautiful hand-made sustainable shoes. We dedicated a year and a half of our lives to that dream, traveling to Peru, finding the most incredible 3rd generation Peruvian-Italian shoe-making family and even had samples developed. The process and the shoes were incredible; however, the sourcing and distribution had become anything but simple.

Peru Moda with sustainable accessories company KOOSHOO

As we deliberated on the precipice of full and total commitment to shoes, the mantra of “simple is hard enough” kept coming back to us. After a few weeks of soul-searching, the answer became clear: shoes, at this stage, were not for us. It was at that moment that we made a commitment to developing our other project of beautifully-made sustainable accessories, promising that one-day with the backing of industry-experience and money, we would return to our shoe dreams.

As it turned out, sustainable one-size-fits-all accessories were indeed hard enough. Designing headbands that are high performance, unique, stylish and versatile was an incredibly intricate process, involving multiple rounds of prototypes and testing. The ENSO, HU and AUREA headbands that people are loving today are in fact the 3 finalists amongst a dozen different prototypes.

Then there were the matters of sourcing organic textiles, finding local suppliers who operate with a conscience, researching recycled and biodegradable packaging options and developing a supply chain with a minimal environmental impact. In other words, though the products appear simple, a vast amount of research, energy and love was invested to make these incredibly good-for-you and good-for-the-planet products a reality.

Today, whenever we look at a new product concept, our first thought is to recall our mantra of “simple is hard enough”. Not only does the mantra help cut away the unnecessary fat, it also implores intelligent design and cuts cost. I know for certain that those simple words have helped us save a tremendous amount of money.


LESSON TWO: Don’t Fall for the Sexy Trap

Make no mistake, no matter what your venture is, you’re going to be tempted by the Sexy.

We all have our ideals of how we’d like to grow our businesses and what that growth is going to look like. A tradeshow in Bali that just feels so right; a sourcing trip to Turkey because you have a good lead; a new piece of equipment that will free up more time... Whatever the business, temptations and dreams are universal to entrepreneurs.

By no means is this lesson a warning against following those dreams. The reason you’re building your business in the first place is surely to follow a dream. Rather, this lesson is a reminder that dreams need balance too. Following blindly or being single-mindedly-focused is not only risky and expensive, it also takes our attention (one of our most valuable resources when starting up) from other solutions that may make more sense.

For example, we had a dream of travelling throughout North America this summer to attend all of the Wanderlust Yoga Festivals as vendors. In theory, it sounds amazing. Beautiful locations, incredible yoga teachers, our target market in abundance and a road trip to boot. In other words, the trip received a Gold Star on the Sexy scale.

Then we got into the details.

First, we began with the facts. Each event costs $2500 to $3500 just to set up a booth. That is before booth materials, electricity, sample stock, staff, transportation, accommodation, food.... Before long, each event was looking more conservatively like $6000, or $24,000 for a summer of 4 events. That’s a lot of headbands.

Second, we went to our gut instinct. Does this feel right? Is this the best use of $24,000? Is this the best use of our summer time? What if we applied that money and time elsewhere – perhaps in more guerilla-marketing initiatives or simply dedicating it to customer service?

In the end, we said no to the Sexy travel in this case, opting instead to invest in the foundations of our business: a new website (coming soon), new products (coming soon) and a rockin’ video-shoot (also coming soon). These initiatives ended up being super sexy in and of themselves.

Believe me, when you work as hard as you do as an entrepreneur – often from first thing in the morning to late at night (what’s a weekend?) – then a sexy dream, particularly one that gets you out of your typical habitat, can absolutely captivate the mind.

So what’s our point? Simple, if:

  1. You combine wisdom of your instincts with the facts/costs of the endeavor and it looks and feels right, then launch yourself headfirst into the Sexy.
  2. You can’t rationalize it from a financial standpoint, or equally important, from your gut’s perspective, then take some time to get creative about other ways to bring the Sexy without falling for the trap.

Guaranteed, just by applying these filters, new opportunities you hadn’t thought of will present themselves.

LESSON 3: Celebrate Your Successes

Being an entrepreneur can feel a lot like a hamster on a clear, plastic wheel positioned right in front of a delicious looking carrot. No matter how far you run, how much you accomplish or how much money you make, that carrot will always be just out of reach. 

Of course, the metaphor applies just as well to life in general.

It’s the old “once I get to so-and-so goal, I’ll be happy” mind-trick. And inevitably, when you get to that goal, you’ll somehow rationalize that your happiness is actually contingent on getting to that other goal that’s just a little further ahead.

The solution to the quandary: when you get to those little goals along the way, make a point to step off the hamster wheel for a night (or more) and go celebrate. Go out for a nice dinner, spend some time out playing in nature, treat yourself with something special.

Organic elastic headbands - the only ones of their kind made in North America

Take some time to come back to the reason that you’re travelling down this path in the first place. Take some time to look back and appreciate just how much you’ve accomplished. Really stop for a moment and remember that this is your life – your ONE AND ONLY life – and experience that deep gratitude towards yourself for your commitment and drive.

Steve Jobs once gave a commencement address at Stanford shortly after being diagnosed with cancer. It’s one of the most inspiring speeches of its kind that I’ve heard.

In the speech he tells a story of how each morning of his life he goes to the mirror and asks himself: “Is this what I want to be doing with my life”. If the answer was ever “no” too many days in a row, he would make a change.

Try viewing your incremental goals this way. They are wonderful opportunities for celebration, reflection and realignment.


LESSON 4: Manage Your Cash Flow

You may have heard that about 90% of businesses fail in their first 5 years. This is one of the most infamous, well-cited facts of entrepreneurship. But we all believe we’re not like the others, that we will succeed where others failed.

If we didn’t believe that, we wouldn’t begin down the path in the first place. It’s likely a big reason that most choose not to be entrepreneurs.  

So what happens to all those businesses that don’t make it? No question there is a plethora of reasons, though none as common as under-capitalization. In other words: running out of cash.

Now that I’m here fully committed, both mentally and financially, to living our dream with KOOSHOO, I understand the cash-flow truth better than ever.

The other day I was speaking with a good friend – a chartered accountant by training - that is running the most awesome online shoe business on the internet (in my opinion). The subject of cash-flow came up and he relayed to me a story that I think encapsulates the challenge perfectly.

 A few months ago a blog with more than a hundred-thousand on their mailing list and a similar amount of social media follows wrote a small piece about our friend’s incredible hand-made shoes. The simple article translated to $22,000 in sales by the end of the month.

Feeling cash rich like never before, our friends began theorizing on how they could apply the money. Ideas like paying down student loans, investing in needed new equipment, or even just a little fun-money were all floated.

The next month they did a bit of sexy-travel, going to tradeshows in London and New York City, though otherwise, continued with business as usual.  Within 2 months the $22,000 had been spent and they were right back at even. No student debts paid; no new equipment. Just like that, the influx of cash was gone.

This isn’t to say the money wasn’t wisely spent; rather it’s a point of just how quick a young business can transition from cash rich to cash poor. They managed well and are stronger than ever though without proper budgeting, it’s easy to see how quickly things can turn for the worse.

We’ve experienced something very similar ourselves.

Cash really is king, whether you like it or not. Treat it that way by remembering:

  1. Simple is hard enough. Don’t overcomplicate – it’s expensive.
  2. Beware of Sexy-traps – they’re also expensive.
  3. Cost out your expenses BEFORE you incur them. What can be trimmed to free up that ever-valuable cash? How can that cash be better used? Know your options before you put down your money.  There is almost always a creative way of getting more for your hard earned dollar.

LESSON 5: Love What You Do

KOOSHOO literally means feeling good in Norfolk, the language of the small tropical Island on which Rachel was born and raised. It’s the perfect name for our company, if you ask us, as it’s a constant reminder why we do what we do. In other words, we ensure that everything we do makes us feel good.

Customer service by KOOSHOO

The three of us writing 650 personal thank you cards for the wonderful Kooshoo customers to be! A great exercise in gratitude! 

Much like Steve Jobs’ mirror analogy above, every decision we make goes through a “does this feel good” filter. If it doesn’t for too many days in a row, we make changes. 

Before starting KOOSHOO I read all the books about working smarter, not harder – the 4 Hour Workweek being a great example. I thought I had it figured out. I thought we’d be different than our other friends that worked all the time. Turns out, that book (and all the others) indeed helped to free up time; however, what they generally gloss over is that the time freed is almost inevitably reinvested back into the business in other places.

So how on earth can you rationalize and sustain this type of commitment? In my opinion there is only one way: LOVE WHAT YOU DO.

Only if you absolutely love what you do and believe in your heart of hearts that it’s the right thing will you be able to live your life to the fullest while building your dream business.


We sincerely hope these 5 lessons will help you towards your dreams. Whenever we speak with new entrepreneurs these 5 points continually come up. It’s the wisdom we’ve gained in our 3 years so far and hope sincerely that it can help serve you in your journey.

If you have any questions or comments we’d love to hear them. It’d be wonderful if this could begin a dialogue. Please either comment below or write to me personally at jesse@kooshoo.com.

Also, if this resonated with you, we’d deeply appreciate you sharing it with others via Facebook, Twitter, Email, Blog...

Lastly, we’d also appreciate hearing your lessons. After all, the 6th lesson is ensuring that you surround yourself with others of like-mind. Entrepreneurs, optimists and those your really trust are invaluable to all of our successes. Together we help uplift and create real positive change in our world.

As Margaret Mead put it:

Never doubt that a small group of thoughtful, committed citizens can change the world; indeed, it’s the only thing that ever has.”


Previous Next


  • Dolly

    Love, love, love your new website and blog. Especially enjoyed 5 Impt Lessons…
    Thinking of starting a business and those were really great tips!
    Keep shining your beautiful selves!


    Dear Jana, Greg, Erin, Sam, Arden, Max and Eden,

    Thank you for your kind comments and sharing your valuable insight. Very much appreciated. We’ll soon be changing blog platforms which will allow us to respond to you on an individual basis. Exctied to share that with you.

    Greg: absolutely agree on your cash flow point. Routine is a brilliant way to ensure those “surprise costs” aren’t actually a surprise.

    Sam: Thanks for your comment. Fluidity is so key. Though we’re always trying to plan our next steps (and I think that’s important) our young business has moved in ways we could never have anticipated. We’ve learnt to leave ourselves open to those unexpected changes as they often bring the most rewarding results.

  • Eden

    Brilliant article – thank you for the reminders!

  • Max

    Digging this article Jesse and Rachel! Thanks for the inspiration :D

  • Max

    Digging this article Jesse and Rachel! Thanks for the inspiration :D

  • Arden

    You make me want to start my own business! Inspiring words brother.

  • Sam Baxter

    Fabulous article! As a new salon owner, what I would love to add is a note on planning. Though planning ahead is great, it’s also important to adapt to whatever situations arise. Early on I felt disappointed with little things that didn’t work out as planned, but now with a more fluid look at the future it has allowed me to tackle challenges as they come, and be more open to new directions :)

  • erin

    Can I give an EFFFFFFFFF YES!!! to this blog post times 1,000,000? Spot on with every point and I was dying over the discussion of Sexy with a capital ‘S’!

  • Greg

    The lesson about cash flow us a critical one. No one likes doing their accounting, but ignoring it makes it far worse, and far more likely you’ll forget something important. An “unexpected” tax bill should never be unexpected, since its based on a percentage of your income and/or profits- you should know these.

    I do my accounts weekly. But whatever works for you, put it in your diary and stick to it.

  • Jana

    So proud, so inspired. Way to go you guys! I LOVE KOOSHOO!!!


Leave a reply

This blog is moderated, your comment will need to be approved before it is shown.

Scroll to top