Great brands aren’t just built on great founders; they’re built on resolute Forever Agreements, the elements of your vision that define the company’s soul and guide every decision.
In a recent article, I highlighted Southwest Airlines as an example of a company that became iconic because of its founders’ unwavering commitment to a radical vision. But today, Southwest is making headlines for changes that contradict its Forever Agreements.
As founders, we have an almost irrational commitment to an idea that has the power to break industry norms and build something that feels different. But what happens when the founder is gone?
It’s rare for non-founder leaders to have a founder-like influence. The willingness to take audacious risks — risks rooted in personal conviction — is almost impossible to replicate. We’ve seen this play out with companies like Apple and Disney.
And now, we’re seeing it at Southwest. Without its founders at the helm, the airline that once defied industry norms is starting to look a lot more like its competitors.
The Vision for Southwest
Southwest Airlines wasn’t just another airline. Cofounders Rollin King, an amateur pilot and businessman, and his attorney, Herb Kelleher (who would later serve as CEO of Southwest for over two decades) didn’t just create a company — they built a movement. Their vision was simple but radical: Make air travel accessible, fun, and hassle-free.
That meant:
- No baggage fees: Because charging extra for the basic needs of travelers felt wrong.
- No assigned seating: Because speed, efficiency, and customer choice mattered more.
- No change fees: Because life happens, and customers deserve flexibility.
- No nickel-and-diming: Because trust was a competitive advantage.
Southwest wasn’t just about low-cost travel; it was about democratizing the skies, making flying accessible and enjoyable for everyone — not just business travelers or the wealthy. Its purpose statement captured the company's Compelling Why: “To connect People to what’s important in their lives through friendly, reliable, and low-cost air travel.”
By introducing new fees, restricting rewards, and shifting toward legacy airline pricing strategies, Southwest is moving away from the very Why that set it apart.
According to an episode of The Founders Podcast, Kelleher once recounted a time when investors pressured him to raise fares to match competitors. He refused, saying: “You don’t understand the philosophy on which we are built.”
His focus wasn’t on squeezing more revenue out of customers — it was on building an airline people could trust. And that trust was earned, not exploited.
Today, that philosophy is fading.
We don't have a marketing department, we have a customer department.
Southwest Airlines Cofounder
Southwest’s Shift: From Founder-Led to Finance-Led
As of May 28, 2025, Southwest will begin charging for checked bags and will transition to assigned seating in 2026. There are also significant changes to its Rapid Rewards program, reducing the points earned on lower fare classes and making it harder for budget-conscious travelers to achieve A-List and A-List Preferred status.
For years, Southwest’s policies reinforced its commitment to the everyday traveler, including families, budget-conscious flyers, and people who otherwise might not have been able to afford to fly. But now? These recent changes suggest a shift toward prioritizing higher-paying customers over the “common man” Kelleher and King originally built the airline for.
Instead of keeping fares simple and inclusive, Southwest is introducing a Basic Economy fare, a move that brings it more in line with legacy carriers. And, instead of maintaining low-cost, predictable rewards, Southwest is making it harder for budget travelers to earn status, favoring high-spending customers instead.
The very things that made Southwest Southwest are disappearing.
And that’s where the real risk lies — not just in lost revenue, but in lost trust.
When Trust Erodes, So Does Everything Else
Here’s the thing about trust: It’s not a marketing tactic. It’s an agreement between a company and its Ideal Stakeholders. It’s a promise that says: We see you. We understand you. And we’re always going to put your needs first as our company evolves.
For decades, Southwest honored that agreement. Families flying with small children didn’t have to worry about paying extra just to sit together. Loyal customers knew exactly what their points and rewards meant.
Now? Those agreements are being rewritten. Not because customers asked for it. Not because it improves the experience. But because financial pressures demand it. And that’s where so many great brands stumble.
Things won’t change much for business travelers — in fact, they’ll earn points even faster. But for everyone else, this is a significant change in how they interact with the brand and whether they choose Southwest over other airlines in the future.
Growth vs. Identity
Founders don’t build brands to maximize shareholder value. They build brands to solve problems, disrupt industries, and build high-trust relationships with all their Ideal Stakeholders.
But once a company becomes successful — especially when it goes public — the pressure shifts. The board, investors, and financial analysts start asking: How can we extract more? Instead of asking: How can we build more?
That’s what is happening to Southwest. Although Kelleher stepped down as CEO in 2001, he remained a champion of the airline’s mission until his passing in 2019. In the years since, his successors have increasingly prioritized financial performance over the core philosophy that made the airline different.
This is what can happen when a company moves from operating in Founder Mode to Successor Mode — where decisions are made not based on the Forever Agreements but on what the data says will boost quarterly earnings. This shift often happens over multiple leadership transitions, as decisions drift further from the founder’s original vision and the Forever Agreements that built trust begin to erode.
The irony? Playing it safe can often be the biggest risk of all. The moment a brand starts looking like every other competitor, it loses the very reason customers chose it in the first place.
A Learning Moment for Founders
For founders, the takeaway is clear:
Your Forever Agreements are your company’s most valuable asset.
The second you start compromising on the very things that made you different — the things that built trust with your Ideal Stakeholders — you set off a slow-motion collapse.
That collapse doesn’t happen overnight. It starts small. A minor tweak here, a policy shift there. A little more focus on optimization, a little less on differentiation.
Then one day, you wake up and realize something: You’re just another company.
3 Questions Every Founder Should Ask
- What made my company different in the first place?
- What agreements have I made with my Ideal Stakeholders?
- Are recent decisions reinforcing or eroding the trust that built this brand?
3 Questions Every Successor CEO Should Ask
- How do I uphold the founder’s Forever Agreements while evolving the company?
- What agreements with Ideal Stakeholders must remain intact?
- Am I making decisions based on long-term brand integrity or short-term financial pressure?
If you don’t have good answers to those questions, you might already be drifting.
Founder-Led vs. Founder-Like
Southwest’s real test isn’t just whether these changes will improve its financials in the short term. It’s whether it can evolve while still honoring the core philosophy that made it different.
If Southwest’s leaders begin to think and act like founders, they may find a way to adapt without losing the trust of their Ideal Stakeholders.
If not? They risk becoming just another airline. And that might be the biggest challenge of all.
