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The Twenty: Elite Impact Education Platform

Risk is inevitable; irresponsibility isn’t.

Why a well-defined company culture with bold, disciplined, and consistent leadership is non-negotiable for sustained success.

October 9, 2026   |   Volume 44

From investing in private real estate to running a business, to getting married and raising a family—everything in life carries risk. You can’t outrun it, you can’t avoid it, but you can position yourself to face it head-on.

Last month, I was honored to speak at an intimate event with Howard Marks in NYC, but the true privilege was being part of his audience. While he spoke about risk in terms of how he believes others should approach investing, his insights were equally valuable when taken through a broader lens, and that’s a little bit of what I want to take you through today. 

Risk predominantly carries a negative connotation, but reflecting on what he called the best thing he has ever heard about risk, Marks neutralized it by explaining it this way: risk means more things can happen than will happen, a quote from Elroy Dimson, a finance professor at London Business School. 

How much less intimidating does that seem? 

Howard marks

He went on to explain that you should approach the future as a probability distribution: many things could happen, but only one will happen—so why hide from what could be a good outcome of taking a risk? " No risk, no reward" is a cliché for a reason. When risk is at play (and it nearly always is at some level), there’s an equal chance you could miss out on something good happening because you tried to play it safe. 

“It ain't what you don't know that gets you into trouble. It's what you know for certain that just ain't right.” 
Mark Twain

One of the biggest tenets of the investment philosophy that Marks helped create at Oaktree Capital is that they do not base their decisions on macro forecasts. Why? Because he strongly believes that no one knows what is going to happen more than anyone else, and, even more, no one knows what the impact of what is going to happen will be. 

He gave the example of the 2016 election. There was an 80% probability of Hilary Clinton winning, which meant a 20% chance of her losing the election, which she did. It was predicted that if Trump won, the stock market would collapse, yet the opposite happened: it went straight up. 

You don’t know what’s going to happen. “Experts” don’t know what’s going to happen. And risk is omnipresent in life. So what do we do about it?

We run on disciplined systems. To build and sustain extraordinary businesses, extraordinary lives, and extraordinary families. This is how we responsibly position ourselves to handle risks and roadblocks as they emerge along the way. 


Culture vs. Climate

At DLP, we run on a disciplined system known as the Elite Execution System and remain diligent about prioritizing our core values, especially the 20-Mile March, which means that we put in the same consistent effort day in and day out, despite headwinds or tailwinds. 

Culture vs climate

This year, I introduced the concept of Culture vs. Climate to the company, which is a different way of looking at the discipline that drives us. 

Culture is the what. It’s a declaration that lives in our values and our words. It’s what we believe, value, and say we stand for. Metaphorically speaking, it’s our root system.

  • Why do we exist?
  • What do we believe?
  • How do we treat people?
  • How do we make decisions?
  • What behaviors get rewarded?

Climate is the feel. It’s a daily decision that lives in how our leaders show up. It’s what our team members experience when they walk in every day, the emotions they have, their experience of being part of this company. It’s the weather that swirls the root system of our culture. 

  • Do people trust leadership?
  • Are people energized?
  • Are teams aligned?
  • Is there hope?
  • Is there fear? 

Strong and healthy cultures can survive a difficult season; temporary storms do not define the ecosystem. Culture is what drives long-term performance, while climate drives short-term performance. This part is important: leaders steward both, but never sacrifice culture to improve climate. 


Gaps between culture and climate are closed or widened daily by the decisions of leaders. 

There are five dimensions of climate every leader controls:

  1. Trust
  2. Clarity
  3. Psychological Safety
  4. Recognition
  5. Accountability

Each of these sounds pretty important, doesn’t it? 

That's why investing in leadership development is one of the areas in which the entire senior leadership team and I pour so much of our time, energy, and resources; it’s central to building an Extraordinary Enterprise.

Leadership conference

We’re just days away from hosting our annual Building Extraordinary Organizations and Leadership Conference, which we host to not only invest in our own existing and emerging leaders, but also those at the organizations that we lend to, that we invest in, and that we consider partners in our mission of transforming lives through the Building of Thriving Communities, including the non-profit signature partners of the DLP Positive Returns Foundation.   

This year, much of the training we’ll do to equip and empower leaders will be based on Liz Wiseman’s great book, Multipliers: How the Best Leaders Make Everyone Smarter. Over the last year, we’ve adopted key lessons from her earlier book, Impact Players, which is all about how you show up in your job, as a leader or otherwise. Part of our culture is about hiring, retaining, and empowering these people; the kind of people who make work light for others and who look for opportunities hidden within the toughest challenges; the ones that ask, “What more can I do?” and never say “That’s not my responsibility.”

In Multipliers, Wiseman focuses on what makes someone an impactful leader; someone who can multiply the impact of their team, without adding headcount. She explores why some leaders seem to drain capability from teams while others amplify it. Based on a study of more than 150 leaders, she identified two distinct leadership styles: diminishers and multipliers. 

Diminishers: Leaders who believe intelligence is rare and fixed, relying only on their own smarts. 

Multipliers: Those who believe intelligence is abundant and can be cultivated, getting twice the capability of their people. 

Team
Working at desk
Team discussion
Lending team

The 5 Disciplines of Leadership: Diminishers vs. Multipliers

Wiseman outlines five key disciplines that differentiate Multipliers from Diminishers.

01. The Talent Magnet   

(DISCIPLINE: Managing Talent)

  • The Diminisher Approach — Empire Builder
    Hoards talent, uses people for personal gain, and underutilizes skills, causing stagnation.
  • The Multiplier Approach — Talent Magnet
    Attracts high-caliber people, deploys them to their highest use, and removes barriers so they can grow.
02. The Liberator

(DISCIPLINE: Creating Environment)

  • The Diminisher Approach — Tyrant
    Creates a tense, high-stress environment that induces fear of judgment, stifling people's best thinking.
  • The Multiplier Approach — Liberator
    Generates an intense but safe environment that demands people's best work while giving them the freedom to think.
03. The Challenger

(DISCIPLINE: Setting Direction)

  • The Diminisher Approach — Know-It-All
    Gives directives, showcases their own knowledge, and tells the team how to do things, limiting the organization's vision.
  • The Multiplier Approach — Challenger
    Defines opportunities, asks hard questions, and challenges people to push beyond what they think is possible.
04. The Debate Maker

(DISCIPLINE: Making Decisions)

  • The Diminisher Approach — Decision Maker
    Makes centralized decisions inside an inner circle, leaving the organization confused and slow to execute.
  • The Multiplier Approach — Debate Maker
    Drives sound decisions by convening rigorous, data-driven debates, ensuring everyone understands the rationale.
05. The Investor

(DISCIPLINE: Executing Results)

  • The Diminisher Approach — Micromanager
    Drives results by managing every detail, intervening frequently, and creating an organization dependent on them.
  • The Multiplier Approach — Investor
    Gives away ownership, invests in others' success, holds people accountable, and provides backing instead of taking over.

Multipliers are the leaders we are building at DLP; those who achieve superior results, doubling an organization’s intelligence and capacity without adding headcount. 


Leadership decisions are the biggest risk in your organization. 

The biggest risk that any organization faces is knowing which leaders to empower. Identifying the leaders who are, or could become, multipliers for your organization is crucial. It’s yet another example of why, despite 14 consecutive years of recognition by the Inc. 5000 as one of America’s fastest-growing companies, our senior leadership team, including me, remains connected to the front line—and we’ll run like that forever.

Leadership

We need to see how new and experienced leaders are showing up for their team; how they’re communicating wins, challenges, and setbacks; and how they are growing—or stalling in their leadership journey. Using the tools of the Elite Execution System (EES) is key to staying disciplined in this area. 

The healthy and flourishing roots of a culture are your strongest asset against risk, but their strength is only as good as your climate, which is fueled entirely by the consistency, authenticity, and care of your leadership team. Never forget what my friend John C. Maxwell says: everything rises and falls on leadership. 


Upcoming Events

Leadership event 2027

Equip & Empower: The Extraordinary Summit

March 29-31, 2027  |  Dallas, TX

Join DLP Capital for an intimate, high-impact gathering designed to equip and empower extraordinary people to create greater impact in the areas that matter most. It's about becoming more intentional in your leadership, relationships, resources, impact, and the legacy you're building.

Register

Marriage retreat 2027

Elevate: The DLP Marriage Retreat

April 16-18, 2027  |  Glen St. Mary, FL

Join us at Island Oaks Resort for a powerful retreat hosted by Lloyd and Linda Reeb. This experience is designed to help you and your spouse dream boldly, align deeply, and live fully, translating thoughtful intention into meaningful action.

Register

Family event

2027 Extraordinary Impact Family Event

July 28-31, 2027  |  Pigeon Forge, TN

We are already building on the incredible foundation of this past year to bring you the 2027 Extraordinary Impact Family Event. We are designing a fresh, immersive experience to help your family align on its purpose, build lasting wealth, and make an extraordinary mark on the world.

Register


Wenner Family BHAG Progress

Our family's big, hairy, audacious goal (BHAG) is to experience 1,000 extraordinary days in 100 different places before our eldest son, Donny, goes to college.

 We started working towards this goal in May of 2022, so we’re 4 years and 4 months in and right at 471 days as of September 30th. With 4 years and 8 months remaining, we’re right on track to achieve 1,000. 

Recent Extraordinary Day Highlights

Jakey birthday

We celebrated Jake’s 5th birthday with an unforgettable safari—and of course a big cake. 

Cape town africa

We spent a day touring Cape Town, South Africa, including meeting penguins and hiking to Cape Point.

Impact africa service day

One of the most powerful days

One of the most powerful days was a Mission Day with the organization Impact Africa.


Where I’ve Been

Location waterberg africa

Waterburg, South Africa

Location dubai

Dubai

Cleveland ohio

Cincinnati, OH (to see the Jaguars beat the Bengals!)


Where I’m Going

Location nashville tennessee

Nashville, TN

Location dallas texas

Dallas, TX

Location austin texas

Austin, TX

Location colorado springs

Colorado Springs, CO

Location tulsa ok

Tulsa, OK


Looking to learn more?

Meet the team in person, or talk it through one-on-one.

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