Dear Founder

How do you lead when every decision feels like a bet on the future? In Dear Founder: Letters of Advice for Anyone Who Leads, Manages, or Wants to Start a Business, Maynard Webb—former COO of eBay, chairman of Yahoo!, and investor through the Webb Investment Network—offers a collection of heartfelt, practical letters that help founders navigate every stage of building a company. Written with journalist Carlye Adler, the book is both a tactical guide and a personal mentorship program from someone who has seen startups rise, fall, and scale to greatness.

Webb argues that starting and growing a company is among the hardest—and most meaningful—things anyone can do. You’ll face loneliness, doubt, and constant decisions under uncertainty, but if approached with integrity, curiosity, and grit, those challenges can become crucibles for leadership. Through short, conversational letters, Webb distills decades of experience into a timeless playbook covering topics like setting culture, managing crises, navigating relationships, and developing sound judgment.

Founders as Lifelong Learners and Servant Leaders

At the core of Webb’s philosophy is a belief that leadership begins with humility. Like Howard Schultz’s emphasis on servant leadership in Onward, Webb encourages founders to see themselves not as commanders but as stewards—responsible for nurturing teams and culture so that the company can thrive beyond any individual. He reminds readers that companies reflect their founders’ values. Authenticity, transparency, and integrity are not just moral choices—they are strategic advantages.

Each letter captures this ethos through real stories: how Meg Whitman taught Webb to run into the fire during crises at eBay; how Marc Benioff used philanthropy and equality at Salesforce to define purpose; and how Webb himself learned from early failures to balance compassion with rigor. These examples make clear that what separates enduring companies from fleeting ones isn’t just innovation—it’s the character of their leadership.

Navigating the Founder’s Journey

Webb structures the book around the arc of a startup’s life, starting with the early days of founding and funding, progressing through management challenges, scaling, and eventual legacy. In the beginning, you learn how to choose co-founders, hire diverse teams, and define a culture before it grows on its own. As the company gains momentum, you face harder decisions—delegation, judgment, poor performers, losing key hires, or being replaced as CEO. Later come existential challenges: crises, public scrutiny, or failure, and finally, what it means to leave a legacy that outlives you.

Each of these stages introduces new tests of judgment. Webb shares frameworks like the RACI model for decision ownership, the Richter Scale for crises, and Stephen Covey’s circle of influence for choosing battles. He connects these lessons to timeless principles of leadership psychology—emphasizing self-awareness, emotional resilience, and fairness.

Why These Ideas Matter

Webb’s letters resonate because they address what few startup playbooks do: the human side of entrepreneurship. Startups aren’t just about valuations and growth—they’re about people, integrity, and purpose. For every technical or financial decision, there’s a personal one hovering underneath: how to remain authentic when the world tries to manage you, how to balance family with ambition, and how to lead through vulnerability.

Ultimately, Dear Founder is not about how to become rich but how to become a better leader—the kind that builds organizations where people feel inspired, respected, and capable of greatness. These letters capture a lifetime of learning in a format that feels personal, timeless, and immediately useful to anyone building something from nothing.

Webb insists that culture isn’t something that evolves naturally—it’s something you must design intentionally from day one. Every action, policy, and even physical space communicates what your company values. If you don’t define the culture, it will define itself—and not necessarily in ways you’d like.

Authenticity Over Copying

Many founders imitate Silicon Valley fads—foosball tables, unlimited snacks, or titles like “growth ninja.” Webb calls this a mistake. A culture must be authentic to your values and the work you do. He recounts his experiences at eBay and LiveOps, where even small things—like Meg Whitman working in a cubicle just like everyone else—signaled openness and equality. Culture is made of everyday choices that reflect what matters most.

Questions That Define Your Values

To uncover what culture you want, Webb suggests posing specific questions: Are you frugal or lavish? How do you support learning and mentorship? Do you reward long hours or outcomes? Do you celebrate departures with dignity or ignore them? Every answer defines how people experience working with you. At eBay, treating sellers as partners became the company’s moral compass—“making our sellers successful was job number one.”

Evolution and Adaptability

Webb reminds founders that culture isn’t static. What works for a three-person startup might fail at three thousand employees. He urges leaders to revisit their core values every six months and ask: “Do we still believe this?” Authentic cultures evolve while remaining anchored in purpose. Inflexible ones calcify.

“Authenticity is the foundation of the strongest cultures. Copycat cultures never last.”

Like Simon Sinek’s advice to “Start With Why,” Webb argues that alignment around shared purpose outlasts perks or slogans. Culture, he says, doesn’t live in posters—it lives in behaviors. Founders who live their values create organizations that endure.

Every day, leaders make judgment calls that shape careers, products, and futures. Webb writes that understanding how your mind makes decisions—imperfectly, and often unconsciously—is one of a founder’s most crucial skills. Drawing inspiration from Malcolm Gladwell’s Blink, he explores how biases, blind spots, and context distort our reasoning.

From Snap Judgments to Structured Thinking

Quick decisions can be essential, but they’re also dangerous. Webb admits that many CEOs reward familiarity—hiring people who “seem like us”—and avoid unfamiliar innovations. He counsels founders to slow down and design transparent, fact-based decision-making processes. Always ask: “Do I have all the facts? What biases might be influencing me?” Then, solicit dissenting opinions. The best leaders, he says, make others feel like they made the decision—even when the final call was theirs.

Empowering Others to Build Judgment

Delegation is an exercise in trust. Webb’s RACI model—who is Responsible, Approves, Consulted, and Informed—clarifies ownership and accountability. But he pushes further: as CEO, your job is to develop others’ judgment, not monopolize it. Great organizations scale by distributing decision-making authority, ensuring others can act independently when the founder isn’t in the room.

Honing Through Experience and Humility

Mistakes, Webb writes, are inevitable—and indispensable. The key is to learn quickly, conduct postmortems, and never hide from bad calls. In his words, “We all must realize that we are applying judgment every day. Do your best to have pure motives.” Experience may make judgment easier, but only if paired with an open and curious mind.

Webb believes the best leaders inspire action through listening, not intimidation. He contrasts fear-based leadership, which silences teams, with inspiration-based leadership that multiplies creativity, trust, and ownership. Quoting Stephen Covey’s maxim, “Seek first to understand, then to be understood,” Webb underscores that listening is a leader’s most undervalued tool.

The Transformative Power of Listening

In one letter, he recalls a tense exchange with a CEO who reacted defensively to feedback. Rather than reflecting, the leader argued back—turning advice into a battle. Webb realized that defensiveness wasn’t just tiring; it was contagious. If the CEO couldn’t listen to investors, how could he hear his employees? A culture of reaction breeds silence—and mediocrity.

Creating Psychological Safety

When CEOs listen openly, they set a tone of curiosity. Employees feel safe to surface concerns and ideas. Leaders who listen poorly, however, create what Webb calls a “command-and-control culture.” To reverse this, ask clarifying questions, acknowledge differing opinions respectfully, and repeat what you’ve heard before offering solutions. The goal isn’t agreement—it’s understanding.

“The very best companies are led by inspiration, not power.”

Inspired teams solve problems faster because people feel ownership. This echoes Daniel Goleman’s Emotional Intelligence: empathy, not authority, drives performance. Webb reminds readers that inspiration doesn’t mean softness; it means clarity, vision, and faith in people’s ability to rise.

Webb’s mantra in crisis management is simple: “Run into the fire.” Every company will face its 9-on-the-Richter-scale moments, and how leaders respond determines whether they emerge stronger or scarred. Drawing on his experiences during eBay’s outages and Yahoo!’s corporate turmoil, Webb outlines a disciplined framework for crisis response.

Assess the Magnitude

Before reacting, gauge how bad the problem is. Is it a tremor or an earthquake? Small issues can become catastrophic if ignored. Webb and Meg Whitman used a “Richter Scale” to categorize incidents, ensuring proportional—and fast—responses.

Overreact, But with Precision

Webb advocates alerting everyone immediately, deploying resources, and coordinating responses transparently. However, he warns against abusing emergency status or overworking teams. Crisis management is a muscle developed through repetition and clear communication. “Run into the fire,” yes—but know when the fire is out.

Tell the Truth, Tell It Fast

Silence kills trust; transparency restores it. During eBay’s 22-hour outage, Whitman and Webb personally called customers to apologize. That act of humanity built more loyalty than any marketing ever could. After the storm, conduct postmortems, fix root causes, and turn scars into systems. In Webb’s world, “never waste a crisis” isn’t cynicism—it’s growth.

Failure, Webb insists, is not the end of the entrepreneurial journey—it’s an education. Whether a product flops, a market resists, or a startup folds, the test is how you respond. He explores founders’ emotional arcs from denial and rationalization to responsibility and recovery.

From Rationalization to Ownership

When companies fail, common excuses dominate: “The market wasn’t ready,” “We ran out of money.” Webb cuts through these rationalizations. “Who picked the market? Who spent the money?” he asks. True responsibility means acknowledging your role in outcomes. Personal accountability is the first step to reinvention.

Failing Gracefully

He urges founders to communicate openly with investors, care for employees during layoffs, and help customers transition. Leaving gracefully protects reputations and preserves opportunities for “round two.” He cites examples of founders who returned stronger—like Steve Jobs at Apple or Jack Dorsey at Twitter—because they failed with dignity, not denial.

Resilience as Mastery

Webb likens resilience to a muscle strengthened by body blows. Drawing on his childhood hardships and professional setbacks, he frames adversity as training for greatness. Echoing Viktor Frankl’s message in Man’s Search for Meaning, Webb argues that purpose transforms suffering into progress. When failure comes—and it will—your legacy will be how you handled it.

Webb expands the definition of success beyond profits. A company’s true measure, he says, is whether it impacts people positively—both inside and outside its walls. This means cultivating inclusion, giving back, and designing a legacy that lasts longer than any founder’s tenure.

Diversity and Belonging

Hiring diverse talent is only the start. Inclusion requires constant effort. Drawing from research and voices like Lori Mackenzie and Masha Sedova, Webb describes practical steps: anonymous resume review, diverse interview panels, and equitable parental leave. Diversity adds not just fairness but performance—companies with varied perspectives simply build better products.

Philanthropy and Purpose

Citing Salesforce’s 1-1-1 model—1% of equity, time, and product for good—Webb argues every startup, no matter how small, should embed generosity into its DNA. At LiveOps, employees formed volunteer teams and managed charitable programs themselves, reinforcing respect and unity. When companies cultivate conscience, they attract loyalty and meaning.

The Long View of Legacy

Finally, Webb asks leaders to differentiate between building a career and building a company that lasts. Legacy, he explains, means codifying values so they endure beyond you—like IBM’s mentorship culture or eBay’s commitment to community. True leadership is knowing when to step aside, mentor successors, and let others carry the mission forward. As he concludes, “Great companies outlive great founders—but only if those founders lead with purpose.”