My 4 Year Anniversary: 10 Lessons in Real-Life Entrepreneurship

4 years ago today I registered my company The Inspirational Lifestyle Limited.

Many of us dream about going into business for ourselves, and it astonishes me to see that a mere 1,460 days ago I made it official.

Of course, it’s not quite the dreamy, lavish, easy ride we all hope for. Far from it.

For those of you interested in starting – or are currently engaged in – the entrepreneurship journey, I’d like to share what it’s really like to go into business for yourself. While I may crush your fantasy of the beachside laptop lifestyle, I hope to give you courage to move forward despite the barriers.

How It All Began

It all kicked off when I read Lifestyle Entrepreneur, written by my book publisher and long-term mentor Jesse Krieger. I remember surges of adrenaline pulsing through me as I opened my eyes to the idea of career freedom.

I had been a loyal employee since the age of 13, when I first did grueling part-time work at a shipping and distribution warehouse. Even back then I knew I hated taking orders and having someone else dictate how I spent my time. But I had bought into the global belief that you had to work for someone else until retirement.

Aged 28, after 7 years in the Department of Corrections, I was becoming increasingly frustrated with being forced to follow rules that made no sense, working a set number of hours, bureaucracy that slowed progress, and the limitations to my creativity. The potential impact I was capable of was much less than what I was being allowed to exercise.

In the background to all this, for a few years I had been actively engaged in self-development. At first, this was centred around my career, with a somewhat needy focus on progression and promotion. Then I turned my focus to my social life, with an even needier focus of getting laid. Yet, eventually this growth started improving my quality of life immensely, and I wanted to share my learning with others.

So, hyped up by Jesse’s example, I wrote my own book.

I sacrificed summer fun and a 2 week holiday to slave over my computer, cranking out the worst self-help book ever written. I completed the entire manuscript in those 2 weeks.

I sent it out to friends and family, asking for their most brutal feedback. They lovingly tore it to pieces. They wanted to see more of “me” in there. This intimidated the shit out of me, because I just wanted to hide behind exercises and instructions.

But I took their advice and rewrote it. I included my weaknesses, failures, real-life examples, and even my secret fantasies and dreams. When I sent it out for further feedback, the response was remarkably different.

LESSON #1: You must reveal the truth about yourself to connect with your ideal audience.

The Birth Of Coaching

Fast-forward through a dismally unsuccessful attempt to self-publish the book, you’ll find me at a dress-up party where I’ve grown a mustache to suit the 1950’s theme, only I end up looking like I’m on To Catch a Predator. Drunk and feeling spontaneous, I impulsively invite a friend to start coaching with me for free.

She and I agree to 6 months’ of weekly sessions, in exchange for an honest review and testimonial at the end. Through my sister-in-law I found someone else who’s keen for the same deal. I now have 2 free coaching “clients” and no idea what the fuck I’m doing. I just want to know whether coaching is a good idea, or just a delusional fantasy.

In the background, every spare minute of free time outside of my day-job is spent writing blog posts and designing a website. I spend hours at it, only to end up with an amateurish piece of crap that constantly malfunctioned.

Later, I realised that I did this to avoid investing in anything, therefore leaving myself uncommitted to creating my own business.

LESSON #2: Invest in professionals to do the work you suck at, so you can focus on what you’re good at. Starting a business is as simple as

taking a small action of doing what you love as a service or product.


Finally, I hired my own coach, Phillipe Drolet (I highly recommend him), because I wasn’t making any progress overcoming my fear of asking for payments. I had just spent almost $6,000 dollars on advertising and netted a grand total of zero clients from it. Life savings, down the toilet. (Don’t waste time with advertising until you know how to create clients through invitation and conversation).

With Phil’s help I started reaching out to people who’d read my book. By this time, it had been published far more successfully by Jesse’s company Lifestyle Entrepreneur Press, and The Legendary Life had become a #1 bestseller on Amazon.

I invited people to discuss it with me. Another friend of mine, who’d helped edit the book, met me for a beer and indicated that she’d loved the ideas in the book. I took a deep breath and offered her paid coaching. She said yes.

I almost shit myself.

LESSON #3: Your first clients will probably be people you know already. Don’t restrict who can be your client with bullshit made-up rules. Let people support you.


Next there was my friend from dancing, who wanted help overcoming an addiction to legal highs. Then there were work colleagues who wanted to overcome fear barriers to progressing their career. There was the random dude who responded to one of my Facebook posts about building social confidence.

Slowly but surely, opportunities came. I faced my fears of inviting people for coaching and asking for money, and a business started forming in front of me.

For every Yes, there were 10 No’s. I was getting battered by rejection – as I saw it at the time – yet had no time to work on these barriers.

I could clearly see that this could be a real business, but with my full time job I was running out of hours. Even after reading and implementing the concepts in 4 Hour Work Week by Tim Ferriss (I managed to get my full time job down to 25 hours/week) and basically ending my social life, I was still struggling to find time.

I went back to Phil, and – with my heart pounding – I asked him: “How do I switch to full time?”

LESSON #4: You can’t do something well if your energy and attention is spread all over the place. Focus and commitment is required for massive growth; which means brutally sacrificing lesser priorities.


Phil told me: “You’ll never be 100% ready. The best you can hope for is feeling 80%.”

Holy shit, I thought, I do feel about 80% ready. For a few weeks I floated in a daze, trying to comprehend that I was actually considering leaving the safety of a guaranteed paycheck to go out into the unforgiving wild.

I was wracked with doubt about my skill, guilt about deserting my work colleagues, and fear of being mocked by my friends.

It turns out these fears were justified, in that I did lack skill, my work colleagues did suffer without me, and my friends did second-guess me doing this. But, it also turns out, none of that stuff mattered. It was a necessary price I had to pay for increased freedom.

Finally, I sucked up my courage and handed in my notice at work. I impulsively announced to everyone on Facebook that I was doing it, fully committing to a genuine attempt at entrepreneurship. I felt like I was trapped in the body of a reckless lunatic and being unwillingly dragged into a suicide-mission.

I was living someone else’s life.

LESSON #5: You will face massive resistance to making big moves. Notice how that resistance comes from people who a) have no experience or knowledge on the subject and b) have their own agenda for holding you back.


At first, it went kind of well. I had now signed up to a coach-training program with Jacob Sokol (again, highly recommended) and was growing my client base. People were starting to take me seriously and some money was starting to come in. I had lifestyle freedom; I got up when I wanted and had a whole bunch of free time.

It never occurred to me that I might need to manage my finances differently, so I kept on spending like usual.

Suddenly, the calls dried up. The bank account dwindled. My calendar started looking rather barren. The first fluttery feelings of panic started to disturb my blissful freedom, and I began to wonder what the fuck was going on. I thought I had been doing everything “right” and it was all supposed to be uphill from here.

I started getting desperate. My neediness for money infected my work like Ebola. I was scaring people away without knowing why, and my stress levels grew with my work hours. I was now working 80-plus hours per week while my income decreased steadily. Despite all of this, my spending remained the same as when I was a full-time employee.

Inevitably, I hit zero.

I didn’t know where my rent was going to come from. I was depressed, stressed to the max, and feeling utterly helpless. I was searching for part-time work while hating myself for even considering it.

Eventually, I swallowed my pride, hung my head low, and went to my parents for a loan.

LESSON #6: Entrepreneur money fluctuates wildly at first, and you’ll have no idea what “works” and what doesn’t. Live lean – necessities only. Be prepared to borrow; most businesses suck for their first few years.


Over the next couple of years, my stress-levels, enjoyment of life, and money fluctuated erratically. One month I would be loving it; focused, having a great impact, working with people I loved, totally living by what I preached, and living large on big paychecks. The next month I’d be searching frantically for quick-fix money solutions, banging my head against the wall with poor-fit clients, scatter-brained, hypocritical, and procrastinating.

I eventually relented to fear and took up part-time work with Corrections again. Immediately, I was faced with my old issues: no time, no freedom, and restricted creativity.

My values were screaming at me: This ain’t right!

What I didn’t realize was that I had been avoiding something important. These fluctuations weren’t random, but in fact a totally predictable consequence of my behaviour.

You see, there’s only one thing that grows a business: Building relationships.

Social media posting, blogging, creating business cards, advertising, website design – these things are all just distractions from what creates a successful business. They help to some extent – dependent on the type of business – but they have 1/10th the impact of inviting potential clients to have real-life conversations (and to a lesser extent, talking with influencers and partners).

But, of course, this part of the job is the most psychologically challenging – that’s why so many wannabe entrepreneurs avoid it and their businesses suffer.

It meant facing fears about my worthiness, battling through my neediness, having to listen to my mind repeat the “I’m not good enough story,” and feeling repetitively abandoned through rejection. It meant hearing the words “No thanks” over and over again. It meant spending dozens of hours with people who will never contribute anything of value to my business, simply to learn a lesson about who I shouldn’t focus on.

LESSON #7: Focus 90% of your time and energy on having conversations with quality people. Aim to serve them in any way you can, with no intention of trying to get something from them. Inviting them to become a client is one powerful way of serving them.


I never lost the passion.

Despite the tough months and the intimidating growth of my debt (to almost $100K), I loved my work. The look on someone’s face when they have an insight – a new perspective of reality – that you just know will improve their life forever, is indescribably rewarding.

I decided that I was willing to end up homeless for this cause. I committed to die trying. I had found my calling.

Nothing was going to stop me.

LESSON #8: Create a business that you would continue doing for free even if you suddenly became a billionaire. Make it something you feel you must do to have meaning in your life. Money cannot be the primary purpose.

About 2 years into this journey, I met Mike Wells.

We explored my work and got excited about the idea of bringing groups of people together to discuss the principles and philosophy we believed in. We could clearly

see a gap: self-development enthusiasts had no-one to talk about it with.

Brojo was born.

When Brojo formed, I saw the power of a community. I felt the raw thrill of bringing together people and leading them towards supporting each other

to grow. Mike and I both volunteered hundreds of hours of our lives to creating, facilitating and growing this community (Brojo does not make a profit). Neither of us have ever found something this fulfilling before.

Every week, I trekked to bars around Auckland to run group sessions. Sometimes no-one else would show up, and I’d end up having a quiet beer and reflection, or maybe just coach 1 guy. I showed up no matter what.

LESSON #9: Make it bigger than yourself. Bring in partners and create a tribe. Have an impact through many that you could never hope to have by yourself. Let go of control, to allow growth. Keep showing up until it works.


After moving to the Czech Republic, my cost of living has reduced and I’m finally in a space where my business is financially stable (though I’m always prepared for this to suddenly change). For the first time, I finally realized my dream of working while I travel. My girlfriend and I just returned from a relaxing trip in Spain where I spent my mornings coaching and my afternoons frolicking poolside or at the beach.

Ironically, what finally stilled the fiscal fluctuations was letting go of my emotional attachment to money.

When I finally made a commitment to focus on serving people strongly – with money dropping to a distant 6th or 7th place in the hierarchy – things started to change. It clearly saw what I needed to focus on each day, and seeds I planted long ago started to bear fruit.

Once my audience realised that contact with me generally made life better for them, the contact increased. Naturally, a small percentage of this contact lead to paying clients, but this factor is of little concern to me.

Through my clients, Brojo community, and feedback from readers of my latest book Nothing to Lose, I am becoming a vehicle for a wealth of knowledge I could never have hoped to achieve on my own. I am beyond privileged to learn from those I serve; it seems paradoxical that I am paid to do this work, as I feel like I receive more from it than any individual client.


LESSON #10: Focus on helping the people you love to solve a problem you hate. Charge for this service and money will come, but keep focused on the service first.


As the influence and learning comes to me from my audience, I feel myself inching more toward the philosophical realm.

I am drawn more to the author side of my work (I have two more books on the way as well as a brief philosophical novella), as I want to share the combined wisdom of everyone I work with.

Brojo University is starting to take form. We are looking to bring the Brojo experience to as many people across the world as possible, and make living with integrity realistic, practical and achievable. Watch this space.


Make no mistake; I have suffered to get here, and will continue to.

Money will always fluctuate. As my profile grows, more haters come out of the woodwork to criticize and belittle me, and I still feel the sting of this negativity. Also, I now face the question of how to have an even greater impact and reach, so that those who cannot work directly with me or Brojo can still benefit from what we’ve discovered.

Some of you have been supporting me for a long time now.

Sometimes it’s sharing with me how something I’ve written or done has improved your life. Sometimes it’s providing opinions that challenge my work and force me to smarten up. Sometimes it’s buying my products and services. Sometimes it’s just even a brief “Keep at it, old boy.”

It all helps. Believe me, as much as I’d like to claim I would have gotten through everything without support, it would be a lie. Your support is an invisible hand on my back, pushing me forward.

Entrepreneurship is fucking hard. End of story.

While it’s more psychologically miserable to work a day-job for some company who ultimately gives zero fucks about your life, it’s still emotionally easier to be an employee than it is to be working for yourself.

Don’t start a business to make life easier; start a business to make life more meaningful.

Thank you all for helping me get through the seemingly impossible barriers, and I hope to repay you simply by continuing the never-ending mission.

4 Responses

  1. Dan, thank you for your brutally honest description of what it takes to be an entrepreneur. I applaud your determination to stick with it through the ups and downs and your truthful advice to focus on the service being provided to our clients rather than on the money. It surely will increase the more we are of service. I look forward to seeing how the Brojo community will emerge and grow on a global scale. Well done and keep up the great work.

  2. Great story Dan, I was trying to fit in where we met up in the time line. I think I have a pretty good idea. I remember saying that I would enjoy watching you grow but really had no idea how tough it was. You hid it well.

    I’ve taken on my own entrepreneurship ventures over the years and although nothing really took off, it did teach me a lot about myself and how to leverage my strengths in my exiting job. Also similar to you, it exposed my weaknesses.

    I admire your vulnerability, tenacity, courage. I appreciate you.


  3. It is very inspiring to read this post. Thank you for sharing your journey and of course your knowledge and wisdom of self development. I am reading your second book “Nothing to lose now” now.

  4. Hey Dan,

    It’s great to read about your progress! I’m super proud of you for the growth, progress and dedication you’ve shown over the past few years.

    May the next few years be even more fruitful and fulfilling.

    PS Love that- “Don’t start a business to make life easier; start a business to make life more meaningful.”

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