Comfortable is Where Dreams Go to Die: Lessons from Dave Stech on Wealth, Family, and the Power of Six
Everybody is missing something in life.
That was the thought ringing in my head as I sat down with Dave Stech, entrepreneur, investor, author, and the embodiment of what it means to Be the Giraffe—to stick your neck out and see farther than the herd.
We started with something simple yet profound: Change is hard. Change or die.
But Dave’s story proves that change is not only possible—it’s essential if you want to stand out and reach higher in business, wealth, and life.
From Trailer Parks to Multi-Billion-Dollar Exits
Dave didn’t start with a silver spoon. He grew up in a trailer park, eating mayonnaise sandwiches when his father—a hardworking ironworker—fell from a fifth floor and was out of work for nearly two years.
“I developed two things during that time,” Dave told me.
“A burning desire to be filthy, stinking rich—and to be a great dad.”
And that’s exactly what he became. His sons have achieved billion-dollar business exits, and Dave has built a life that most people can’t even imagine.
But he’s the first to admit: It didn’t happen because he was comfortable.
Comfortable is the Silent Thief
One of the most powerful lines Dave shared was this:
“Comfortable is where dreams go to die.”
Read that again. Because it’s the enemy of every entrepreneur and dreamer.
Most people hit a comfortable six-figure income and stop. They sit still in the same job, the same role, the same life—because comfort lulls them into inertia.
Dave’s philosophy is radically different. He’s on a lifelong quest for more. Not just more money—but more impact, more learning, more growth.
Comfort? That’s not the goal. It’s the danger zone.
Grateful… But Never Content
Despite everything he’s achieved, Dave wakes up every day feeling like the luckiest guy alive. But he pairs gratitude with perpetual discontent.
“Grateful, but not content.”
That mindset keeps him moving forward. It’s the antidote to victimhood and regret—two toxins that kill more dreams than failure ever will.
Why Family is Business—and That’s a Good Thing
Most people think wealth is about money. Dave sees it differently.
We talked about how he’s intentionally run his family like a business—complete with mission, vision, values, and measurable outcomes.
Why? Because:
“What you don’t learn, your kids will inherit. What you don’t become, your kids will inherit.”
Dave believes your family deserves the same intentionality and strategic planning you’d give any successful venture. That doesn’t mean it’s less loving. In fact, he insists it makes families more loving, because everyone knows where they’re headed and why.
The Happiness Triangle
Dave sat his sons down at ages five and seven and shared the first of his two famous triangles:
Make Money
Do Good
Have Fun
People often guess that “Do Good” or “Have Fun” is the most important. Dave argues otherwise:
“It’s all about making money. Because the more money you make, the more good you can do, and the more fun you can have.”
This isn’t greed—it’s stewardship. Money is fuel for impact.
The Money Game
The second triangle? The Money Game.
Dave taught his kids that winning the money game boils down to:
Generating more cash (active, passive, and recurring income)
Accumulating more wealth (assets that throw off cash and appreciate)
Keeping more of what you earn
And then he posed the life-changing question:
“Do we stay small and keep it all… or add a zero?”
Dave’s family votes to add a zero—to income, net worth, and even happiness.
The Power of Six
Perhaps the most striking idea from our conversation was Dave’s Power of Six. After losing 3,000 contacts when his Palm Pilot died, Dave had an epiphany:
“It’s not about a lot of people. It’s about fewer, deeper relationships.”
He decided he only needed six key people in his life—people who met strict criteria:
No uncontrolled greed
No uncontrolled egos
Implicit trust
Excellent at what they do
Committed to winning
People he genuinely likes
His philosophy?
“Do fewer, bigger things with fewer, better people through fewer, deeper relationships.”
This is how you compress time and accelerate success.
Being Contrarian Takes Courage
Dave’s success is built on being contrarian. He predicted the real estate collapse in 2005 and was laughed out of rooms. Three years later, he was proven right.
“When you’re contrarian and you’re right, you’re a genius. When you’re wrong, you’re an idiot.”
Innovation isn’t a democracy. If everyone likes your idea, it’s probably mediocre.
Invest, Don’t Spend
Perhaps the most powerful practical shift Dave teaches is this:
“Never spend. Only invest.”
He doesn’t “spend time.” He invests it.
He doesn’t “spend money.” He invests it—whether it’s on relationships, knowledge, or strawberries at Costco. Because investing implies a return. Spending implies it’s gone forever.
The Entrepreneur’s Call to Action
I left our conversation with a renewed sense of urgency—and a warning for entrepreneurs and dreamers alike:
Comfort is the enemy.
Regret is the poison.
Growth lives in discomfort.
Time is the real currency.
So ask yourself:
Who are your six?
Are you investing or spending your time?
Are you grateful but never content?
Are you brave enough to be contrarian when it matters most?
If you’re ready to Be the Giraffe, it’s time to stand taller, see further, and stick your neck out—because comfortable is where dreams go to die.
Be bold. Be curious. But most importantly, be patient. And remember: invest your time, don’t spend it.
P.S. If this episode resonated with you, you’ll love my Be the Giraffe book.
