Winning Ugly

Winning Ugly

I’m exhausted from staying up late the last couple nights getting stuff done.

This is called WINNING UGLY– where you win, but not gracefully.

I’ve found that entrepreneurship, as portrayed on social media, is not glamorous.

It’s WINNING UGLY– those mundane moments where you’re grinding out documents, dealing with unhappy customers, being frustrated by employees who do shoddy work.

I’ve been coached by billionaires and CEOs– who I had thought were god-like, perfect people.

But when I got to know them, I heard about their failures and how they dealt with things that went wrong.

And their perseverance for years until finally, the compounding effects of their effort began to multiply.

WINNING UGLY is about relentlessly focusing on getting the result, over and over, not about how you look in the process.


Remember I told you this was coming

The next wave of millionaires and billionaires are coming from the health sector.

Baby boomers are getting older– leading to chronic health problems that traditional medicine (pills and surgery) doesn’t have an answer to.

Growth-minded entrepreneurs and mid-career professionals are overworked and stressed out– facing problems that cannot be solved by more coffee and working harder.

We all want to have whiter teeth, feel better, look better, make more money, provide for our families, and achieve “success”.

You’re seeing a ton of “get rich quick” courses, peddled by breathless 21 year olds– with 20 years of experience, about how easy it is.

You’re going to see “Limitless” pills plastered in ads everywhere– and even mattress companies claiming they can give you the competitive edge.

The winners (of which I hope you and I be in that group) will have these characteristics:

+ Massive social proof– not just celebrities with paid endorsements who are 3 degrees away, but friends causing their own friends to buy.

+ Cross-functional– you’ll see a wave of figureheads who are highly knowledgeable in business, fitness, medicine, public speaking, marketing, and so forth. This causes society’s definition of health to expand from just treating the sick to preventative care and maximizing peak performance.

+ Products that are services, and services that are products- You can “buy” physical products, but they will have subscriptions, online membership programs, and live events integrated. The next wave of influencer won’t be the rented Lambo type, but tell emotionally powered stories that eventually lead to a product sale.

I’ve been intentionally aligning myself with these folks, since I know they need systematic digital marketing not to be “famous”, but because championing their cause (if I believe in it) leads to building a community, which leads to purchase of products.

Watch the billionaires start podcasts, sell courses (and even courses on how to create courses), peddle skin creams, and tell you about their membership programs.

According to AARP, the average cost of having cancer is $150,000.

This destroys health, wealth, and families at the same time– the financial and emotional burden is tremendous. And it’s not just on the patient herself.

Your car insurance payment will be lower or disappear when self-driving cars eventually come around. But your healthcare costs will skyrocket.

And that’s both with traditional medicine, as well as non-traditional forms– natural medicine and Eastern practices that range from good old fashioned exercise to eating, impacting your microbiome, cellular-level hypoxia, and mental well-being.

Remember I told you this was coming– as you start to hear more and more about these topics.

Limiting Beliefs

I’m not being paid enough.
– employee mindset

I need to create more value so I can earn more.
– owner mindset

It’s THAT person’s fault, not my problem.
– employee mindset

How can I solve problems instead of create them?
– owner mindset

If you’re struggling to pay bills, get your projects done, or get out from under the massive weight on top of you, consider your limiting self beliefs.

Thank you to Woody Marks for the gold nuggets, helping me grow as an entrepreneur.

If you’re a one person business– guess what?

You’re not a business.

Because when you step away, your business doesn’t exist anymore.

What would happen if you went on vacation for a month with no internet?

You need people, process, and platform so that your business can run without you being there.

Just as ridiculous is the CEO of a one-person firm.

I picture a toddler triumphantly riding their Big Wheel around town, flexing to the other children.

But eventually, it’s naptime or Mom is calling– so it’s time to put the toys away.

There’s nothing wrong with working for someone– as an employee, freelancer, or consultant.

In fact, that’s the best choice for most people– since who wants to deal with the risk, long hours, and stress?

Why not have plenty of of time for family and friends– as well as your health and personal life?

Be clear on whether you’re working for someone else or wanting to be a leader of your own company– and all that entails.

But if you’re claiming to be a “business”, you have obligations beyond what you alone can do.

Pick 3 of these 5 things– family, work, health, sleep, friends. Which two things are you dropping?

Set The Example

I’m not feeling motivated today, so I’m not doing any work.

And if others aren’t working hard, then neither do I.

It’s my manager’s job to constantly praise me and my work, even when I’m clearly messing up.

Besides, I’m not being paid enough for what I do.


That was my attitude when I first joined a team over 20 years ago.

I made a lousy $36,500 a year while working 80 hours a week. That’s $9 an hour.

I was managing people who made $250/hour.

And running projects with multi-million dollar budgets that were making the company a lot of money.

I worked harder than everyone else around me, as far as I could see. And I believed those other people didn’t do much, at least from my point of view.

I was defensive and entitled, blaming other people for my issues instead of owning up and taking charge.

It’s not until you become a manager yourself that you learn how ridiculous your behavior was when you were younger.

For my entrepreneur and manager friends– my empathy is to you, since I understand how much time you spend helping your people, even if they don’t appreciate it now.

Keep on going, since a few of these eager, smart, immature young adults will blossom into incredible leaders– and you’ll look back on those moments with gratitude.

Set the example by getting the job done, even if those around you aren’t or are full of excuses.

I spent nearly 10 years as a corporate employee.

Some days I didn’t want to go to work.

I didn’t like the office politics, which were at every company I’ve been at.

There were incompetent, mean, and unmotivated people that wanted to sabotage my projects, take credit, or just waste time.

Yet I’d still do it again if I could turn back the clock 20 years— since the 10 years of corporate were my training ground for the 10 years I’ve been an entrepreneur.

I couldn’t enjoy the freedoms I have now were it not for learning how to run teams, deal with contracts, speak at conferences, get results at meetings, work with clients, and communicate in general.

Where else would I learn about how to manage a $50 million P&L without risking my own money?

How else would I have been able to meet CMOs and CEOs were I not an executive at several Fortune 500 companies?

Where else could I have learned how to build corporate training systems, except to see how it’s done at large companies?

Though I’m an entrepreneur at heart, I’m grateful I made it through those formative years.

Because every giant corporation was a small business at one point, too.

Walking through DigitalMarketer’s, after a series of meetings and trainings, I reflected on how DigitalMarketer was once a company of 8 people and is now quite the operation.

It now takes a whole minute to walk from one end of the office to the other, when a few years ago, I remember mainly one room on one side of the building.