The Four Freedoms of True Wealth - David DeWolf

The Four Freedoms of True Wealth

A couple of weeks ago I stumbled my way into a large group discussion. Thinking I was in a group of like-minded people, I was surprised to see the conversation quickly shift to a predominant focus on wealth creation, wealth-building, and monetization.

There’s nothing wrong with wealth creation and, as an entrepreneur, I understand that monetization is not only desirable, but necessary.

But money is not the end, and when it’s made the end – or, the primary conversation point turns to making more of it – things quickly get off track. After the conversation had ended, many of those involved reached out to me in order to express how put off they were. They felt like they were constantly being sold by others. They felt as though they had been pulled into a money-making scheme. They lost trust in the host and that he had their best interest in mind.

Wealth is an abundance of what is truly valuable. In many regards, money is valuable, in many others, it’s truly not.

True wealth is greater than money. In fact, money doesn’t make you wealthy at all. Money can support your wealth, but it can’t create it and it may even take it away.

True wealth consists of the following freedoms:

Freedom to live your values

Values are those things in our lives that are core to our being. We believe that they are foundational, goods in and of themselves. Regardless of the ramifications, we adhere to them. True wealth provides the freedom to live our values consistently.

Freedom to be who you are

We can allow ourselves be defined by others, by ourselves, or by our very nature. But who we are is really the only thing we have in life. True wealth allows us to be who we are, who we are called to be, and who we want to become. It gives us the freedom to be ourselves.

Freedom to relate with others

At the end of the day, it is our interactions with others – the community within which we live – that make us human. Our relationships with others are far more valuable than any possessions we could ever collect. True wealth provides us with the opportunity to be in relationship with those that we love.

Freedom to pursue your passion

Passion is associated with what we care deeply about. Pursuing our passion brings joy to our lives. True wealth exists when we are able to recklessly pursue our passion. It is the freedom to do what we love, for the sake of itself.

There’s no doubt that each one of these freedoms can be supported by money, but if money becomes the ultimate end, it can also take these freedoms away. We can become slaves to our pursuit of money, and in the conversation I experienced a few weeks ago, this is what many people began to notice. The passionate pursuit of money for its own end had begun to take away from the true reason why money had any worth. It seemed to become more important to some than the freedoms it had the potential to afford.

Question: Have you gotten intentional about your values, your life, your relationships, and your passions? Do you know what it is you’re pursuing, or are you caught in the pursuit of money, thinking that it will buy you what you’re ultimately after? I’d love to hear from you! You can leave a comment by clicking here. Learn to live an integrated life with humble confidence. Get it Now

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Align Your Expectations in Marriage and Life - David DeWolf

Align Your Expectations in Marriage and Life

This past weekend, I blew a gasket, and in doing so, I almost blew up our marriage.

Over coffee just a few days in advance, Teresa shared with me that she intended to take Catherine to the final out-of-town soccer tournament. We had been trading on and off: one would go to baseball, the other to soccer.

With baseball ending the weekend before, despite it being my turn, Teresa was making herself available to take Catherine to soccer. I understood it. Being with her daughter and having dedicated time together was important to her.

But I was also upset. There’s nothing I love more than having those dedicated moments myself, and combining that with an athletic tournament where I get to see my kids having fun and living life, competing with the same vigor with which I pursue my own life, gives me great joy. It is the single biggest thing I look forward to in my life: watching my kids compete, have fun, and use their God-given talents on the the sports field.

I shared with Teresa that I really wanted to go, that I didn’t want to miss it. She explained that there were multiple activities. We decided together to look for different ways for me to somehow be involved.

Over the course of the next few days, my work exploded. There was a ton going on and I simply couldn’t find ways to clear my calendar. I had asked Teresa to send me the schedule and I had asked her to think with me how we might find alternative plans. But by Friday night, nothing had been put into place.

I was furious. There was no way for me to make it to the out-of-town tournament. I made known my displeasure. I blew up.

Looking back, with the problem solved, I realize that my frustration stemmed from having great expectations. I have always had this perception in my head that it is Teresa’s responsibility to figure out logistics for our kids. I consider it part of her job to find ways for our family to operate, to prioritize our time with the kids, and to figure out how we will spend it. I consider carpools and babysitting to be her job.

Teresa, on the other hand — and rightly so — perceives my responsibility to be that of a helpmate. She knows that the busyness of our life is largely due to my schedule and my desire for the kids to be able to participate in the activities they love. It is stressful for her to consider all of the moving parts of a weekend away. She has homeschooling activities and many other things to do throughout the day.

As a result, her expectations are out of sync with mine, and mine are out of sync with hers.

The deep fight that we had over the weekend was due to an underlying mismatch of great expectations. I was furious that Teresa failed to recognize my desire to be with Catherine and understand that that was more important than anything else we had going on over the weekend. I perceived it this way because of my expectation that she was responsible for making all of the logistics happen.

Teresa, on the other hand, perceived in me an unreasonable expectation of her having to do it all. She felt backed in a corner, as though she had to pick up the pieces for the demands I was putting on her. She has an expectation that, as helpmates, we work together and that I participate in the logistics of the family.

It’s important in a marriage and for the sake of the kids that we figure out how to align our expectations, get on the same page, and communicate without blowing a gasket.

Question: Have you faced a similar misalignment of expectations in your marriage? How have you dealt with it? I’d love to hear from you! You can leave a comment by clicking here. Learn to live an integrated life with humble confidence. Get it Now

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Become Who You Are - David DeWolf

Shaping Your Life So It Doesn’t Shape You

I was an awkward 7th grader, six inches taller than anyone on my basketball team. I towered over the competition. They put me in when we needed to score, rebound, or anything else, despite the fact that I could barely shoot.

My size simply gave me an advantage.

But it wasn’t my size that placed me in my first of five high schools when I was in 7th grade, it was my brain. I could compute mathematical equations that many adults couldn’t figure out. I found myself as the only junior high kid in a classroom full of sophomores and juniors. I had kids three and four years my senior coming to me, asking for help with their homework.

I was labeled the big nerd. I was labeled the smart kid.

A short year later, we moved from that school in Belgium to Minot, North Dakota. I found myself in a small Catholic school – again with a series of individuals anywhere from 7th grade to seniors in high school. At this school, I became known for…well, nothing.

I was in advanced classes, but I had transitioned from algebra to geometry, and geometry wasn’t my cup of tea, nor did I have much interest in it. On the basketball team, my talents were exposed: I couldn’t shoot and I couldn’t dribble, and those at the school had learned to do it quite well. My size had faded away and was now quite average among my peers.

I lasted at that school for a year before moving on to a public school in the same town. I started afresh. Once again, my vision of me and the perception others had changed. This year I made the basketball team. In the semifinals game, playing against my former school, I scored 32 points, including six 3-pointers. All of a sudden, I was a star for the junior high B-team. I made the baseball team and while I wasn’t necessarily the cool kid, I had a cool group of friends.

A year later I landed in Colorado Springs, Colorado, where I would spend the next year-and-a-half. Settling in, I found a niche. I found a group of friends at our church and quickly became a leader in my youth group.  I didn’t even make the basketball team and was eventually cut from the baseball team — but I had a different identity. I was good enough at sports, but not great. I was average at academics, but not too nerdy. I had a group of friends and became “one of the guys”.

It was only a year-and-a-half before it was time to move again. This time, to Cheyenne, Wyoming. I stuck out like a sore thumb. It was a bit difficult to break into a group of folks that had been together for their entire lives. Because I wouldn’t cede to peer pressure, I simply didn’t gain much traction. After a short four months, I decided that it was time to go off to college. And so I did – without a high school diploma.

I had experienced 5 high schools in only 3 and a half formal years of high school.  More importantly, I was perceived as 5 different people in a short seven years. I had allowed my surroundings to define me.

Moving so often wasn’t easy, but, I learned a lot from the experience that I wouldn’t trade for anything.

Too often, we allow the world to define us. We allow the world to dictate who we become. We become the star athlete when we happen to be better than those in our immediate circle. We become a big nerd when we happen to excel in academics at a point in time in our lives. We become “one of the guys” when we ‘click with others’ and don’t stand out. We’re an outsider when we are new or different.

Too often, we define ourselves by these perceptions instead of reaching down to figure out who we really are.

Since highschool, I have been fortunate enough to be able to step back and see myself for who I really am. The diverse experiences in my life gave me the opportunity to identify the trends that wove themselves through each one of my experiences. They allowed me to figure out who I really am and double down on those gifts.

Don’t be defined by your surroundings. Figure out who you really are and leverage your gifts. Shape your life. Don’t let it shape you.

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The 3 Sights of Vision - David DeWolf

The 3 Sights of Vision

Study after study has shown that one of the most essential traits of any leader is the ability to cast a vision. Not only does it inspire others to follow, it points them in the right direction.

A clear vision is at the center of any high performing team and is the basis for strategy. Without vision, the people perish.

When crafting a vision, consider the following sights.

Foresight What does the future hold for the industry?

In the early days of personal computing, Microsoft’s sole goal was to put “a computer in every home”. They clearly envisioned a world where personal computing technology became ubiquitous.

Microsoft founder Bill Gates dared to dream. He envisioned what life might be like if everyone had a computer at their finger tips. He envisioned moms looking up a new recipes, students doing their homework and professionals exchanging digital documents that included spreadsheets and presentation materials. He could describe a world that had been reinvented by the personal computer.

Foresight provides a glimpse into the future. It requires imagination and creativity and is born out of a broad understanding of industry trends. It helps the entrepreneurial leader to paint a picture of what can and will be.

Insight What about our organization will help shape the industry?

Apple has always envisioned a world where users love using technology. In fact, they have painted a picture of technology getting out of the way to the greatest degree possible.

Apple founder Steve Jobs fought the status quo. He painted a picture where technology was simple to use and intuitive. He imagined a world without instruction manuals, where small children could use technology by simply picking it up. He realized that Apple’s creative core was significantly different than their engineering oriented competitors and he saw how Apple could push the industry to be more aesthetically pleasing by leveraging this asset to it’s fullest potential.

Insight provides a glimpse into how our organization will participate in the future of the industry. It is born out of a deep knowledge of an organization’s assets and how they can be leveraged to bring about the foresight. It helps the entrepreneurial leader paint a picture of why we are relevant and how we will participate.

Cross Sight How do the unique assets that we have integrate with each other and the rest of the ecosystem?

Uber has reimagined the way people would move throughout the world. They clearly see a world where our mobile phones become the hub of transportation and are used to create a more enjoyable experience.

Uber’s founder Travis Kalanick crafted a bold outlook. He saw on-demand and reliable pickups. He imagined cashless transactions. He integrated this vision into an already thriving ecosystem. Herealized that the ecosystem he developed was valuable to others and he wove his vision into an underutilized portion of the transportation industry (Black Cars).

Cross sight provides a glimpse into the ecosystem. It is born out of a deep understanding of your own differentiated assets and a broad understanding of the industry. It helps the entrepreneurial to paint the picture of how the vision will interact with the rest of the world.

Vision evolves – it becomes more clear, if you will – over time. As an industry changes, so does the reality of the future. As an organization matures, additional assets can be leveraged for ultimate impact. As an industry evolves, additional integration points may arise. But, as the vision evolves, it continues to pull a company. It is the magnetic force that pulls us.

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Don't Give Up the Second Time Around - David DeWolf

Don’t Give Up: If the Third Time’s a Charm, Second’s a Dog

After 90 minutes I was ready to pull my hair out. “Let’s try that again. I think it could be tighter.”

Mike was right. Everything I said seemed like it was coming out wordier than it needed to. I wanted it tighter and I wanted to put a finer point on my message.

“I’m not this much of a bumbling idiot, I promise.”

Mike Manion and I were in the studio together for the second time. Having a co-host for “Steal My Show” was supposed to make this easier and more engaging.

It didn’t seem to be working out that way. Maybe the opposite.

Mike saw my frustration.

“It’s not uncommon for the second time around to be harder than the first. The first time around you’re not thinking about it. You’re just going with the flow. The second time around you’re trying to replicate the results and fix what you didn’t like. By the third time, you’ll be perfecting it.”

This got me thinking. Maybe there is something to “Beginner’s Luck.”

And then it hit me. How many people give up after the second time around, simply because it’s harder than the first and they figure they are “not good at it”?

Here’s my theory. The second time you do something, it takes about twice the time or effort of the first. The third time, on average, it takes half.

Don’t give up. Persevere and perfect your art. It will pay dividends in the long run – in more ways than you expect.

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4 Steps BEFORE Building Your Startup Team - David DeWolf

4 Steps to Take Before Building Your Startup Team

The excitement and passion were high. Karen and Jose couldn’t stop talking. No matter how much time we had together, it was apparent that neither one thought there was enough time to cover everything.

Having just raised capital, they had a million ideas about how they might take their (rather immature) product to the next level. They wanted to discuss several hires they were about to make and talk a bit about how to set up their organization.

After 15 minutes had passed, I barely snuck in a question. “Can you back up? I think I missed something. What’s your vision”?

Karen paused. Jose quickly piped in, but he failed to answer the question. He simply spouted a few more ideas and it was obvious to everyone in the room that he missed the mark.

I asked a follow on. “Let me ask it this way, what is it that you’re ultimately trying to become? Describe your company five years from now. What does it look like? What have you accomplished?”


“Okay. Twelve months from now? How are you different from anyone else in your space?”

More silence.

“Describe your product. Don’t tell me what it does. Tell me why it’s different.”

Finally, an answer. Unfortunately, it was all about the cool technology that had been developed and was unlike anything else in the market. A recipe for disaster.

After a few more questions, it became apparent that the founders of this company had no idea where they were going and how they were going to get there.

All too often I see product companies with nothing more than technology. No vision. No strategy. Nothing but an idea.

I advise first-time CEOs to be deliberate about creating a business by following these steps, each one of which builds upon the other.

1. Develop your core ideology.

What is your mission/purpose? What are your values? Be explicit, this is the foundation of your business and will seed the culture of your organization.

2. Develop your vision.

What is it that you want to become? Where are you going? Get crazy and define that “Big Hairy Audacious Goal”. This will inform your strategy and motivate your team.

3. Develop your strategy.

How is it that you intend to be different? What is your unique advantage? Competing on the basis of being better, or cheaper (obviously), will lead to commoditization. Be deliberate about creating a differentiated strategy.

4. Develop your structure.

How do you need to structure your organization in order to deliver on your strategy? Hiring people without an organizational strategy is a colossal failure waiting to happen.

I was shocked that Karen and Jose raised significant capital with so much ambiguity. While it’s not incredibly common any more (1999 has come and gone), there are plenty of entrepreneurs, intrepreneurs, and organizations that have gone straight from “an idea” to “a product” to trying to build a team. Doing so creates mass confusion and is a recipe for disaster.

A two- to three-day pause can solve all of these problems. Take the time to develop your core ideology, vision, strategy, and structure and you’ll be ready to build your team in no time.


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