Feb 26, 2024

14 Lessons Learned In 11 Years Of Business

On January 26th, 2013, I officially launched this business of mine.

Whether you’re a self-employed business owner and looking to shortcut some of my hard-earned wisdom, or just a reader of my work who is curious about peeking behind the curtain of a different aspect of my process, there will be something for you in this article.

You may have heard the statistic that 20% of businesses fail in their first year, and 50% fail in their first five years. Personally, I don’t give much attention to statistics like these, because I think they’re next to useless. Who wants to compare themselves to the bottom half of any population? (Speaking of statistics – that old 50% divorce rate myth? Total waste of brain space.)

So anyways… I made it past a decade (hooray!), with a healthy, growing business to boot.

Here are fourteen things I’ve learned over the last eleven years. I hope that one (or several) of these tips saves you time, energy, frustration, and headaches.

1. With all due respect, nobody gives a flying fuck about you – they just want to know how you can help them.

Years ago, someone hired me for a one-time coaching session so that I could audit their business and point out high-leverage next steps for them to focus on. This is quite a common occurrence, so I was happy to dig in with them.

They were a travel blogger with a pretty basic setup. Upon seeing what they had out there (and hearing how they talked about it), it quickly became apparent that this side-hustle/passion-project of theirs was almost exclusively about them and their needs.

When I asked them why they started it, they said they wanted to make ‘passive income’ and be an ‘influencer.’ Almost all of their goals were about themselves… their desire for money… their specific financial targets they had for their monthly income.

When I pressed for a deeper ‘why,’ they didn’t have much to say.

I’ll tell you what I told them…

Nobody cares about you.

If your business is just an excuse to try to trick people into paying your bills without you adding real value to their lives, that business will die a quick death. As it should.


Because if you’re primarily in it for yourself, people will know, and you’ll never make real progress.

You know why I started working as a relationship coach?

Because most of my early childhood pain was a result of relationships that were hurtful.

Because whenever I Googled common dating and relationship questions, I was inevitably infuriated by the superficiality of 95+% of what I found.

Because I personally walked the path from ‘I’m miserable and I don’t think I’ll ever be in a real, stable, healthy, reciprocal relationship’ to being in the most nourishing, loving marriage I could have ever dreamed of… and wanted to share my lessons with others.

Because, regardless of whether or not I would make a dime from it for years, I just had to do my best to make even a 1% difference in the accessible relationship advice that was out there in the world

In short, it wasn’t a trivial inkling. It was a passion I burned with. I fucking HAD to do it. There was no way that I couldn’t.

When I meet people who lead with the entitled, lazy, self-serving attitude of ‘I want this business to make me $20,000 a month as quickly as possible’ without being willing to dig in and do what it takes to become someone who is deserving of that, and then the market reflects back their lack of willingness? I have no sympathy for them.

It can’t primarily be about you. There has to be a genuine desire to serve and provide value to people in their lives, or the business will be dead in the water before you begin.

2. The big picture matters. The details also matter.

Some people are big picture visionaries, and others are more detail-oriented.

In business, both of these things matter. And you need to have a functional relationship to both sides of the spectrum.

If you focus exclusively on the big picture vision, and chronically ignore all of the details, the cracks in the foundation will destroy the whole thing.

Conversely, if you’re exclusively detail focused, and never lift your head up out of the trenches to consider the broader vision of what you’re hoping to achieve, you’ll just spin your wheels in the mud and be frustrated by the lack of traction.

Yes, you can outsource aspects of the vision and the details to others. But in my experience, you need to be able to keep your finger on the pulse of both things at the same time, so that the whole business gets to where you want to go, in a healthy and sustainable way.

3. If you lead with trust in your business dealings, you will sometimes get fucked over. Even so, it is still worth it to lead with trust.

Some people move through the world with a default-lens of ‘Is this person trying to fuck me over?’

Their global beliefs are such that they’re just waiting for people to prove their fear right, and show that they are untrustworthy.

In my experience, approaching the world from the opposite vantage point is far more productive.

Lead with trust. Lead with generosity. Lead with giving people the benefit of the doubt. Keep your heart open, while still exercising healthy discernment.

By doing so, you will win far more often than you will be taken advantage of.

What would this look like, in practical terms?

Have a generous refund policy for your products, so that people feel safe trying them out.

A long-term, trusted client of yours asks for some flexibility on their payment terms because they’re going through a tough season? Go for it! Figure something out that can work for both of you.

Want to try out a new contractor that a friend has recommended to you and see if they can bring new value to your business? Don’t waste too much time in the vetting period. Dive in!

According to my worldview (that I have tested across millions of data points), people are inherently good. Sure, there are some bad apples. But they are the exception – not the rule.

So, lead with trust. You’ll go faster further, and you’ll have a better time throughout the whole journey.

4. Business is a never-ending merry-go-round of focusing on product, marketing, and relationships – and if you ignore one for too long, it will take you out of the game.

The three most important things that business owners need to continually focus on (and bounce between) are product, marketing, and relationships.

Inevitably, each business owner will naturally be strongest in one of them.

Once you’ve identified which of the three you’re the strongest in, you should exploit that strength by doubling down on it.

AND… if you notice that one of the three is decidedly not your strong suit, you should put energy into ensuring that it isn’t such a glaring weakness that it takes your business out altogether.

For example, a product focused owner might have an amazing, life-changing product or service… but if they put zero effort into marketing it, no one will ever know about it and it’ll never be purchased.

In another example, a more marketing focused owner might be a natural born salesperson… but if their product is shit, then every person who buys it will just opt-out and then disappear.

So, identify which of the three is your strong suit… double down on it by making it an ongoing focus… and then also make sure you’re functional in all three, so that there isn’t a huge, glaring blindspot in your business.

5. If you’re a new business, you should probably spend at least half of your time on marketing.

Little baby J. Gray doing a radio interview in 2013! Adorable.

Now, an important caveat here…

I know that the majority of business owners that follow my work are in some iteration of the personal brand/coach/creator/service provider/online personality space, so this advice is largely to them. If you’re a SaaS (software as a service) owner then this wouldn’t apply as much to you and you might be better served putting the majority of your attention on product up front.

If you have a newer business (less than 3 years old), it would serve you to spend the majority of your time on marketing and advertising.

In other words, getting people to know about you/your product/your service.

If you’re new to the scene and nobody knows or trusts you, then building up goodwill via content creation (or other forms of mass-scale value creation) would be the place to direct the lion’s share of your focus.

This is one of the biggest mistakes that I see new business owners make. They truly believe that ‘if you build it, they will come,’ as if people will just magically smell the essence of your brand new product or service wafting in the air, and then follow their nose straight to your door, where they will find you and force money into your pocket.

In reality, marketing and advertising are an on-going business necessity.

Regardless of what you think of them as companies, Apple, Amazon, and Coca-Cola (and dozens of other companies) literally spend billions of dollars per year on advertising. Do you think they might know something about being lasting brands with good customer retention? Hmm? Perhaps we can take a lesson out of their playbooks and act similarly.

Now, I’m not saying that you need to necessarily spend money on advertising. In fact, there has never been a better time in human history for free or extremely low-cost advertising channels. But whether you invest time/energy/attention or money on your advertising efforts (or both), it is a vital aspect of business that many new business owners severely neglect – especially new business owners.

6. If 90% of your marketing assets aren’t deemed a total failure, you’re not working boldly enough.

Along with the above point, it’s important to note that on the path to finding your most successful marketing assets, there will be hundreds (if not thousands) of failures.

And if there aren’t? If everything you’re putting out is a screaming success, you’re either in denial, a liar, or not swinging for the fences and taking big enough creative risks.

7. It’s true, business is a marathon. Prioritize your self-care accordingly.

Some people say ‘Business isn’t a sprint, it’s a marathon.’ In some ways, sure. But in other ways, it’s also both.

I think it’s most accurate to say that it is contextually a marathon, but there are also short bursts that you need to sprint. And with all of this energy expenditure, it is absolutely imperative that you treat yourself extremely well.

A former mentor of mine used to say, ‘You can’t treat yourself like a workhorse and expect thoroughbred results.’

A lot of you will be required for the path that you have taken on.

If you chronically neglect your sleep, nutrition, hobbies, relationships, or the things that bring you joy, the marathon has no chance of being sustainable.

Does that mean that you need to have a multi-hour morning routine so that you can get in the zone before doing any high leverage work? No, it definitely does not mean that.

But it does mean that (until the day that we all become full-cyborg) you are a fleshy human mammal who needs to tend to the basic biological needs of your meat suit in order to not burn out.

8. If you don’t love the work you’re doing, you’re dead before you begin.

Apple founder Steve Jobs once said, “The only way to do great work is to love what you do.” I couldn’t agree more.

There will be thousands of obstacles and reasons you could quit along your path. But if you love what you do, you’ll overcome them all with ease, grace, and grit.

One of the best questions I was asked a couple of years ago was, ‘How would you set up your business if you knew that you were never going to change?’

It’s such a powerful question because it forces you to acknowledge the parts of you that don’t change. Especially the things for which you have the most passion, energy, and natural (or cultivated) talent.

It’s an important thing to audit. What were your skills, strengths, and interests when you were very young… and how have those things carried into your life today?

I don’t agree with the ‘find work you love and you’ll never work a day in your life,’ because every job has some percentage of bullshit attached to it. It’s not a black-and-white matter so much as it is a matter of degree. To what degree are you regularly engaging in tasks that are well within your zone of genius? If your job feels like it’s 90% bullshit, then that ratio would be something to look at. But if there’s only 10% bullshit to your 90% aligned, effortless, nourishing action, then you’re in a good spot.

9. Only you know whether you’re honestly doing your best, or just pretending.

When you’re self-employed (especially if you’ve previously had a normal/9-5/corporate job) you’ll quickly realize that, if you allow yourself, it is very easy to phone it in and not actually put forth your best effort.

Why is that? It’s because when you’re the boss, there’s no one to answer to. With the minimized accountability structure (who do you answer to? Just you? Ahhhh, we can let this one slide) there’s far greater flexibility to just do next to nothing, but still appear to others as if you’re showing up.

This is where the power of discipline comes in.

The difference between you having a business that generates you over a million dollars in profit per year and a business that hobbles along for a few months and then dies a merciful death will ultimately come down to your habits, routines, and the standards that you set for yourself.

The profoundly unsexy truth of entrepreneurship is that…

– It matters what time you go to bed

– It matters what you consume (nutritionally, informationally, who you go to for advice, etc.)

– It matters how often you prioritize high-leverage, non-urgent work that advances your business (as opposed to just allowing yourself to lazily drown in busy-work and calling it a day)

And yet, even with this awareness, most people will rest on their laurels, and do next to nothing to create forward momentum.

The shift comes when you move from a place of needing to do it so that others don’t judge you… to doing it because you simply want to be the kind of person who shows up and does what needs to be done, to be in alignment with your own values.

That’s right. It’s not just a behavioural shift. It is an identity level shift.

At the (literal) end of the day, only you know whether you actually did what needed to be done… or if you just engaged in a frantic, reactive set of behaviours that you can pretend were important. My two cents? Prioritize the former.

10. Entrepreneurship is one of the greatest mirrors, and you will constantly be shown where you are not currently free.

From where I currently stand, three of the greatest perpetual mirrors that basically force you to grow are 1) marriage, 2) being a parent, and 3) being self-employed/an entrepreneur. The people that I know who simultaneously engage in all three and are proactively open to the lessons that they provide are all wonderful people.

Entrepreneurship is such a mirror because you basically create a larger organism out of your own strengths and weaknesses.

Just as Kahlil Gibran wrote that, ‘The home is the larger body,’ I say, ‘The business is the larger psyche.’

It is a projection of your own inner world. And it takes on the strengths and attendant weaknesses of the person whose brain child it was (you!).

Just like in marriage or parenting, if someone is committed to blocking out all of the external lessons being offered to them, they can stay stuck in blame and denial for decades.

At all sizes of business, the owner’s mindset needs to be optimized. Beliefs need to be busted and layers of identity need to shift so that they can breakthrough to the next level in their business/personal growth.

If someone has the identity of, ‘I just hate being seen, so I don’t really advertise,’ well then… that’s going to be an issue for people finding out about you, isn’t it?

Or, if you tell yourself that, ‘The product is fine… people are just so picky in this industry’ while your core offering has a 60% refund rate, that would also be an issue that lives and dies in the mind of the person holding onto that belief.

Tactical workarounds have their place… but 9 times out of 10, to get to the next level of growth, the solution is actually a mindset shift that is needed in the belief systems of the owner.

11. Day to day, you can feel like a winner or a loser. But if you widen your time horizon, you will see the broader trend through the years.

I’ll tell you something that my dad (who was also an entrepreneur) once said to me, that has really stuck with me.

Just like most issues in life, if the frame that we’re viewing them through is too zoomed in, we suffer unnecessarily.

But when we zoom out and look at it on a broader time horizon, things feel a lot better and become more workable.

For example, many business owners have come to me and informed me that the volatility of their business (making thousands one day, but then zero the next) stresses them out. But when I have them only ever look at their financial reporting on a monthly or even quarterly view, they feel a lot better about where they’re actually at.

It’s important to note that risk and volatility are two different things. There will be ups and downs when you zoom in on a day-to-day or week-to-week basis. But volatility does not inherently equal risk.

So if you find yourself obsessing over the micro-fluctuations of your income or businesses growth, take a longer view.

Are you in a better position than you were five years ago? Great! Keep it up.

12. Of course it’s hard. That’s the point.

If building a 6- or 7-figure-per-year business were easy, everyone would do it.

If you are confused by why your business isn’t scaling up immediately while putting in the level of effort that only an older version of you is capable of putting forth… why? Make it make sense.

I worked with one man a couple years ago who told me he was dead-set on building a seven-figure-a-year (million+ dollar) personal brand business, no matter what it took.

When I told him what it took, he put forth about 8% of an effort for a few months, and then quit.

So again, when people throw around statistics like ‘1 in 5 businesses fail within the first year,’ please know that these statistics are truly next to useless, because most people’s psychological laziness is truly astounding.

The determination and perseverance of most people barely exists. If you show up with any honest degree of effort and consistency, and you’re actually in it for the long haul, you can’t lose.

Most people ‘lose’ simply because they take themselves out of the arena four minutes into the game.

13. You cannot be a life-changing presence to some without being despised by others.

At this point in my career, most days (through some form of communication) someone tells me some version of ‘You’re amazing/You saved my marriage/I just got engaged because of your awesome work’… and another person tells me some version of ‘You suck/Fuck you/You’re a terrible writer/You’re a fraud.’

And you know what? I don’t take either side all that seriously.

Yes, I may have helped some people, but they also used the tools that I provided them and deployed the courage to get there.

Yes, I might be an imperfect person and absolutely have typos and grammatical errors in my writing. And? That’s fine by me.

So again, the highs and lows in the feedback you get will often allow you to self-reflect and grow in some way. And, as the saying goes, ‘If you live for the cheers you’ll die by the boos.’ Let both sides of the data wash over you, but don’t take any of it too seriously.

If you are to have any kind of real impact with your work, just know that it is inevitable that there will be more people who hate/judge/resent/think very little of your work, compared to the size of the crowd who adore and deeply benefit from your work.

14. People want a clean, linear set of instructions to follow… when in reality, success is the result of messy, simultaneous action.

The amateur wants a clean, linear, A-B-C set of steps to follow.

The professional knows that success comes from messy, concurrent action.

So the next time you catch yourself wanting things to be way more cut-and-dry, notice it, and drop it.

There are absolutely seasons when you’re more growth-focused than profit-focused. There are also seasons where you’ll be more profit focused than growth focused. But that doesn’t mean that you can let either one be completely neglected when it isn’t that particular priority’s season.

There will always be some level of ball-juggling in entrepreneurship. All good. The sooner you accept it, the better off you’ll be.

Marathon, Not A Sprint

I hope that you enjoyed this piece, and that you learned something from it. Or that it clarified or confirmed something for you.

Since I’ve been working with more business owners and people around their money mindset in general, I recently added a new course and monthly coaching call to my community, The Circle.

When you’re a member, you get access to my ten-module Relationship to Money course, and you also get access to a monthly group coaching call on the topics of career, money, wealth attraction, and self-employment on the last Saturday of each month.

You can find out more about that by clicking here.

Wishing you all the best in the coming months.

Dedicated to your success,


Ps. If you enjoyed this article, you will also love checking out:

The Circle, where I offer monthly group coaching calls on all things money and entrepreneurship

How I Built Up A Six-Figure Blog In Two Years

How To Make A Full-Time Income From Blogging (A Complete Guide)

Find Your Unique Gift And Fulfill Your Dreams (90 minute audio interview I did with my good friend Ben)



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