Why Founders with Skin in the Game Build Stronger Companies

I’ve spent over four decades working with other founders, often in those early days when nobody is quite sure if what they’re building will actually last. And one thing I’ve realized is that long before there’s product-market fit, an established team, or even a repeatable process, there’s an unmistakable moment when the founder steps forward and says, in one way or another, "I’m willing to carry the weight."

As founders, we feel that weight long before we ever say it out loud. We invest our time, our resources, our reputations, and a fair amount of our identity into something that doesn’t exist yet. And because the consequences land at our feet, we look at things through a sharper, more honest lens. That relationship between our choices and what they create becomes the structure that holds our company together.

It’s not about being fearless or heroic. It’s far simpler than that. When the outcomes rest on your shoulders, you have to stay close to reality. You have to notice the things most people look past. And over time, that honesty shapes how you lead. It keeps you anchored in the actual conditions of the business, not the story you hope is true.

Let’s talk about what that weight does for us as leaders: how it sharpens our judgment, how it keeps our companies connected to what’s real, and how we can continue to carry it as we scale. Because once you understand that dynamic, you start to see why having skin in the game not only holds founder-led organizations together, it makes them stronger.

The Commitment Every Founder Makes

Long before we ever hire our first team member, we’ve already accepted a commitment many people will never experience: If I’m wrong, I’m the one who takes the hit. We put real pieces of our lives behind something that hasn’t proven itself yet. And even if we never say it out loud, that commitment shapes how we show up from day one.

What’s easy to miss is just how much this affects our thinking. When the stakes are this high, you start testing assumptions differently. You become more curious about how things actually work, not how you hope they will. You get clearer about what matters and what doesn’t. Because every decision, good or bad, doesn’t get absorbed by some distant system. You feel it directly.

And even though that sounds like a lot of pressure (because it is), it’s also one of the greatest advantages of founder-led companies. That weight teaches us discipline early. It forces us into a level of honesty that you just don’t feel when the consequences fall on someone else. Over time, that honesty turns into steadier, better judgment.

Here’s the part many founders don’t realize: When you own the consequences, people watch how you handle reality. They see you base decisions on what’s actually happening, not on preference or convenience. And over time, they start doing the same. Your relationship with the truth becomes the pattern the rest of the company follows, and that pattern becomes the backbone of how the organization operates.

When you take on risk, you are taking on the responsibility for the consequences of your actions. This is what it means to have skin in the Game.

Nassim Nicholas Taleb

How Carrying the Weight Makes You a Better Leader

When you have skin in the game, you see things earlier and more clearly than anyone else in the organization. It’s not that you're paranoid or hypervigilant. You’re just more attuned to the inner workings of your company. And as a result, you:

• Ask better questions
• Stop letting what looks good on paper substitute for what actually works in practice
• Understand the difference between effort and real progress
• Sense when decisions are being made based on preference or comfort instead of what the business actually needs

Over time, this awareness turns into a reliable early-warning system. You can sense when a plan that looks sturdy to everyone else won’t work. You can tell when the goals a department sets for the quarter outpace their capacity. You know before anyone else when someone is in the wrong Seat.

These aren’t mystical instincts you’re born with. They’re the natural result of being the person who carries the consequences if the call is off.

The problem is, when we get busy, we often ignore our instincts. That’s why it’s important to set time aside once a week to ask yourself, “What feels off?” You’ll find that most of the time, you know the answer instantly. Whatever comes to mind first is almost always the thing you need to address now before it turns into something bigger.

This is also where having the right systems matters. In Ninety, the Meetings, Scorecard, and Issues tools give you a continuous, clear view of what’s happening throughout the company so you can spot problems before they grow and stay aligned with the reality of the business. These tools don’t replace your instincts — they sharpen them.

Why Teams Rally Around Founders Who Carry the Weight

Whether you realize it or not, your team pays close attention to how you handle the hard parts of running a business. They watch what you do in the moments when things aren’t going well, when the path forward isn’t obvious, or when a decision needs to be made even though there isn’t enough information. Those are the moments that tell people what kind of organization they’re part of.

When you’re the one who owns the consequences, your team feels it. They see you diving headfirst into the ambiguity instead of avoiding it. They see you take responsibility for your part when something doesn’t work out. They see you dig into the real issues instead of circling around them. And that builds a kind of trust no inspirational speech can replicate.

The practical benefit here is simple: When your team trusts your relationship with reality, they spend less time protecting themselves and more time doing the work that matters. Accountability strengthens, conversations get more honest, and decisions get clearer. And the organization moves faster in the right direction because people aren’t guessing what matters. You’ve shown them.

If you want to understand how much this dynamic shapes your company, start paying attention to what your team mirrors back to you. If you avoid an uncomfortable issue, they will too. But when you step into it, they’ll follow. When you model responsibility and accountability, they learn to do the same. That’s why founder behavior becomes the baseline for the entire company’s culture.

5 Practices to Help You Carry the Weight as You Scale

As your company grows, the weight on you doesn’t disappear. It just shows up in different ways. These five practices help you stay connected so you can continue to make decisions from a place of clarity rather than pressure:

1. Stay close to the places where real work happens: Spend time where value is created — with customers, with the product, with the teams doing the heavy lifting. Firsthand exposure gives you a clearer read on what’s working, what’s not, and where your leadership is most needed.
2. Name the real constraint: Every organization has one thing holding it back more than anything else. When you name it, people know where to focus and what deserves attention now.
3. Own your decisions out loud: When your team hears you take accountability, it strengthens trust and raises the standard for everyone else. It also reminds people what owning your part actually looks like.
4. Ask the questions people hesitate to bring up: Invite your team to tell you what’s not working. The more you create room for honest input, the easier it becomes to address issues before they get too big to tackle.
5. Watch for the problems that keep returning: When something shows up again and again, it’s pointing to a deeper issue in the system. Treat those patterns as a cue that something structural needs adjusting.

Scaling doesn’t remove the weight you carry as a founder. It just makes it easier to lose track of where it’s showing up. These anchors help you stay connected to reality so you can make better decisions, support your team more effectively, and keep the organization aligned with what actually matters. They’re simple habits, but they go a long way toward keeping a growing company grounded.

The Strength Behind Founder-Led Companies

At the end of the day, skin in the game isn’t a leadership style. It’s the reality every one of us who's building, running, and scaling a company lives with. The weight we carry forces us to pay attention, stay honest, and make decisions based on what’s happening inside the business. And when we stay connected to that weight as the company grows, our team stays connected too.

This is why founder-led companies often feel steadier and more aligned. The relationship between our choices and what they create is always right in front of us. And that relationship builds a company that’s productive, humane, and resilient.

If we keep carrying the weight with clarity, if we stay close to what’s real, our organizations don’t just survive growth. They grow stronger because of it.