Trust is the foundation of every business relationship, but even the most successful founders have learned its lessons the hard way. At Do Not Work With (DNWW.io), we study these cases to help others avoid similar pitfalls. Let’s examine some of the most instructive examples from business history.

Steve Jobs and the Apple Board

The story of Steve Jobs’ removal from Apple in 1985 remains one of the most famous trust breakdowns in startup history. Jobs had brought in John Sculley as CEO, personally recruiting him from Pepsi with the famous line, “Do you want to sell sugar water for the rest of your life, or do you want to come with me and change the world?”

Initially, Jobs and Sculley were so close that People Magazine ran an article about their friendship. They would often have dinner together and take walks to discuss Apple’s future. Jobs trusted Sculley completely, even calling him his “father figure” at Apple.

However, when sales of the Macintosh didn’t meet expectations, the relationship deteriorated. Jobs didn’t realize that Sculley was gradually building support among board members to reduce Jobs’ role. In May 1985, Sculley and the board stripped Jobs of his operational duties.

The Lesson

Trust must be balanced with governance. Jobs later reflected that his mistake was believing personal loyalty would outweigh business interests. When he returned to Apple years later, he ensured his role was protected through clear agreements and board structure, not just relationships.

Mark Zuckerberg and Eduardo Saverin

While the movie “The Social Network” took creative liberties, the core story of trust breakdown between Facebook’s co-founders is well-documented. Eduardo Saverin, Facebook’s first CFO, trusted Zuckerberg to handle the legal paperwork during the company’s early funding rounds.

This trust proved costly when new investment documents diluted Saverin’s stake from over 30% to about 0.03%. While Saverin had neglected his duties as CFO according to many accounts, the manner of his removal highlighted how verbal understandings mean little without proper documentation.

The Lesson

Trust must be backed by clear legal documentation. Even among friends, proper contracts and transparency about equity and rights are essential. Today’s founders can protect themselves by having all agreements reviewed by independent counsel.

Richard Schulze and Best Buy

Best Buy founder Richard Schulze built an empire from a single audio store, but in 2012 he was forced to step down as chairman. The reason? He had trusted a CEO who betrayed that trust spectacularly. Brian Dunn, the CEO Schulze had mentored, was involved in an inappropriate relationship with a subordinate.

More damaging than the scandal itself was Schulze’s handling of it. When informed about Dunn’s behavior, Schulze trusted his personal relationship with Dunn and failed to inform the board. This breach of governance forced Schulze out of the company he had founded.

The Lesson

Personal loyalty cannot override corporate governance. Modern founders must understand that their fiduciary duties sometimes require acting against personal relationships.

Travis Kalanick and the Uber Board

Uber’s founder Travis Kalanick built one of the most valuable startups in history, but his trust in his ability to maintain control proved misplaced. Despite having significant voting power, Kalanick was forced out by investors in 2017.

Kalanick had trusted that his board seats and voting power would protect him. However, when a series of scandals erupted, he discovered that even strong legal positions can become untenable when trust is lost at multiple levels – with the board, employees, and the public.

The Lesson

Trust is multidimensional. Legal control isn’t enough; founders must maintain trust with all stakeholders. Today’s founders should build relationships at all levels while maintaining strong governance structures.

Adam Neumann and WeWork

WeWork’s story shows how excessive trust from investors can actually harm a company. Adam Neumann’s primary investor, Masayoshi Son, trusted him with billions of dollars and minimal oversight. This trust enabled behaviors that ultimately damaged the company, from questionable related-party transactions to governance issues.

When WeWork attempted to go public, the lack of proper checks and balances was exposed, leading to Neumann’s removal and a massive devaluation of the company.

The Lesson

Too much trust can be as dangerous as too little. Modern founders should actively seek accountability and welcome proper oversight, using tools like DNWW.io to maintain transparency and trust verification.

George Eastman and Kodak

Sometimes the most dangerous trust is in our own assumptions. George Eastman built Kodak into a photography giant, but the company’s eventual downfall came from trusting their dominance in film too much. When one of Kodak’s own engineers invented the digital camera in 1975, the company buried the technology, trusting that their traditional business model would prevail.

The Lesson

We must not let trust in our current success blind us to future threats. Today’s founders must balance confidence with constant questioning of their assumptions.

Building Trust Intelligence

These stories share common themes that modern founders can learn from:

• Document Everything: Trust is enhanced, not diminished, by clear agreements
• Maintain Independence: Always have your own advisors and counsel
• Create Oversight: Build governance structures that protect all parties
• Verify Claims: Use platforms like DNWW.io to check backgrounds and track records
• Balance Relationships: Build trust across all stakeholder levels

A Final Thought

The history of business is, in many ways, a history of trust – both well-placed and misplaced. By studying these cases and using modern tools like Do Not Work With, today’s founders can build trust intelligently, creating safeguards while fostering the relationships necessary for success.

Remember: Trust is not about blindly believing in people. It’s about creating systems and relationships that enable people to be their best selves while protecting against their worst impulses.