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Strategic Leadership

Everette Taylor’s Unconventional Path to Leadership

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Everette Taylor’s Unconventional Path to Leadership

When Everette Taylor was named CEO of Kickstarter in 2022, it marked a historic milestone—not just for the pioneering crowdfunding platform, but for the tech industry, where Black leadership at the highest levels remains rare. At the time of his appointment, Taylor became one of only a handful of Black CEOs leading a global tech company—breaking barriers in a space that has long struggled with representation. Taylor wasn’t just making noise. He was making impact.

The Journey to the Top

In a candid video conversation with Forbes, Taylor spoke about that journey—from the margins to the main stage—and how his unconventional rise continues to shape his leadership and Kickstarter’s comeback. Raised by a single mother on the South Side of Richmond, Virginia, he dropped out of college—twice. He slept in his car, cold-called his way into rooms where no one expected to see him, and launched his first startup at 19.

Early Life and Career

That early boldness set the tone for a career defined by risk-taking, reinvention, and relentless drive. Without pedigree or privilege, Taylor forged his own leadership style—one that blends creative vision, market instinct, and a deep understanding of culture. His big break came when tech veteran Mike Steib took a chance on him at Artsy, naming Taylor CMO at 29. “Mike taught me what it meant to be a CEO,” Taylor says. “Everything is your responsibility. No excuses.”

Turning Around Kickstarter

By the time he took the helm, Kickstarter’s shine was starting to dim. Though still the leader in its space, “revenue was declining, competitors were gaining ground, and the company’s cultural relevance had started to fade. We weren’t operating at the level we needed to be,” Taylor recalls. To reignite Kickstarter’s influence as a vital player in a rapidly evolving digital ecosystem, Taylor made a bold bet on the creator economy. “I didn’t just want to be a leader in crowdfunding,” he says. “I wanted Kickstarter to be a leader in the creator economy.”

Focusing on Creator Education

Since Taylor joined as CEO, creator education has become a central focus at Kickstarter, and over the past year alone, Kickstarter has rolled out dozens of new product features designed to support creators not just at launch, but to help them sustain, scale, and thrive throughout the full lifecycle of their projects. It’s a vision that’s already showing results, as the company returned to consistent year-over-year revenue growth. “Project success rates on the platform have climbed from around 50% to 65%,” he says. “That matters more to me than revenue or any other metric because our mission is to help bring creative projects to life—and that starts with giving creators the tools, support, and education they need to succeed.”

Cultural Transformation

But the transformation hasn’t stopped at product innovation. Taylor also reimagined the company’s internal culture to reflect the diversity of the global creative community it serves. “Inclusivity was mission-critical,” he says. “It started internally—with our team. My CMO is a Black woman. My head of content is a man of color. Our head of social is a woman of color. We built a team that looks like the world we serve.” With that diverse leadership team in place, together they revamped outreach and education, expanded funding initiatives, and positioned Kickstarter not just as a launchpad, but as infrastructure for creators of all kinds.

Personal Mission

“For me, this work is personal,” Taylor says. “I know what it’s like to fight for an opportunity. I know what it means to have someone believe in you. That’s what we’re building at Kickstarter—a place where creators don’t just launch projects, they build movements.” Two years since Taylor first stepped into the top role at Kickstarter, now 35, he remains an anomaly in the tech C-suite. But he’s determined not to be the last. “There are so many incredible Black men and women who deserve these seats,” he says. “I carry the responsibility of paving the way for them.”

Conclusion

Everette Taylor’s journey to the top of Kickstarter is a testament to his determination and innovative spirit. By focusing on creator education and cultural transformation, he has successfully turned around the company and positioned it for long-term success. As a Black leader in the tech industry, Taylor is committed to paving the way for others and creating a more inclusive and diverse community.

FAQs

  • Q: Who is Everette Taylor?
    A: Everette Taylor is the CEO of Kickstarter, a pioneering crowdfunding platform.
  • Q: What challenges did Taylor face in his early career?
    A: Taylor dropped out of college twice, slept in his car, and had to cold-call his way into rooms to get opportunities.
  • Q: What is Taylor’s vision for Kickstarter?
    A: Taylor wants Kickstarter to be a leader in the creator economy, providing tools, support, and education to help creators succeed.
  • Q: How has Taylor transformed Kickstarter’s internal culture?
    A: Taylor has reimagined the company’s internal culture to reflect the diversity of the global creative community it serves, hiring a diverse leadership team and revamping outreach and education initiatives.
  • Q: What is Taylor’s personal mission?
    A: Taylor’s personal mission is to create a place where creators can build movements, and to pave the way for other Black men and women in the tech industry.

Strategic Leadership

Why top CEOs are saying “I Don’t Know” more often

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Why top CEOs are saying “I Don’t Know” more often

For years, leadership was defined by confidence, control, and certainty. But in 2025, a different kind of leader is rising—one who leads not just with vision, but with vulnerability.

From the tech world to healthcare, more executives are stepping up to say, “I don’t have all the answers—and that’s okay.” It’s not a sign of weakness. In fact, vulnerability has quietly become one of the most powerful leadership tools in today’s workforce.

So why now? And what does this shift mean for teams, culture, and long-term impact?

The Vulnerability Pivot

We’ve seen glimpses of this shift over the past few years. Satya Nadella at Microsoft shared personal stories of parenting a child with disabilities. Jacinda Ardern led New Zealand through a pandemic with compassion and transparency. Oprah Winfrey has long spoken openly about trauma and healing, reshaping how leaders connect with audiences.

In 2025, more leaders are taking cues from that playbook. According to a new Deloitte Human Capital Trends report, 62% of executives believe showing vulnerability builds greater trust among teams, up from just 34% five years ago.

This change is reshaping boardrooms and team dynamics alike.

What Vulnerable Leadership Actually Looks Like

Contrary to popular belief, leading with vulnerability doesn’t mean oversharing or constantly expressing self-doubt. It means being open about challenges, admitting mistakes, asking for help when needed, and inviting others to do the same.

Key behaviors include:

  • Saying “I was wrong” or “I don’t know”

  • Sharing lessons learned from failure

  • Opening up space for feedback from junior staff

  • Acknowledging mental health challenges

  • Prioritizing psychological safety in decision-making

These habits don’t erode authority. They humanize it.

In fact, according to Gallup, teams with vulnerable leaders report 27% higher engagement and 30% more innovation, as employees feel safer taking risks and speaking up.

Why This Matters Now

The modern workforce—especially younger professionals—is craving authenticity. Gen Z, which now makes up over 25% of the U.S. workforce, ranks emotional intelligence and transparency as top traits they value in a leader.

At the same time, organizations are grappling with complex, fast-moving challenges: AI integration, DEI backlash, economic shifts, climate accountability. No one leader can navigate all of this alone—and pretending to only fuels disconnect.

By modeling vulnerability, leaders signal a new norm: collaboration over perfection.

The Risk of Performative Vulnerability

However, there’s a caveat. Not all vulnerability is created equal. When leaders use vulnerability as a tactic without follow-through—or when it’s overly polished—it can backfire.

Employees can sense when it’s performative. And when they do, it creates more mistrust, not less.

True vulnerable leadership is consistent. It shows up in one-on-one check-ins, in how feedback is received, in how accountability is shared across a team. It requires self-awareness and courage, not just well-crafted talking points.

Leaders Are Learners Now

One of the biggest shifts we’re seeing is that leadership is no longer about having all the answers—it’s about being willing to learn out loud.

At a recent summit hosted by the NeuroLeadership Institute, senior leaders from industries ranging from fintech to pharmaceuticals shared how they’ve redesigned internal decision-making to be more transparent and collaborative.

The result? Faster adaptability, higher retention, and more aligned leadership pipelines.

As one VP from a Fortune 100 company put it, “The more I show that I’m learning, the more my team leans in with their own ideas.”

So, How Do You Practice This?

If you’re a leader—or an aspiring one—who wants to lead with more authenticity and courage, here’s where to start:

  1. Own your learning curve. If you’re navigating a new challenge, share that openly. Let your team see your problem-solving process.

  2. Invite feedback, then act on it. Ask your team what they need from you—then show them you listened.

  3. Normalize the messy middle. Not every project will go smoothly. Instead of hiding the friction, talk about what you’re learning from it.

  4. Check in often. A simple “How are you really doing?” can go a long way.

  5. Lead by example, not just intention. If you want a culture of openness, be the first to go there.

Final Word

Vulnerability won’t show up on a balance sheet—but its impact is deeply felt. It shows up in how teams communicate, how innovation flows, and how resilient organizations become when change comes fast.

As the future of leadership continues to evolve, one thing is clear: we don’t need more leaders who have it all figured out. We need more who are willing to grow in public, listen deeply, and lead with their whole selves.

Because in the end, the most effective leaders aren’t just impressive—they’re real.

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Strategic Leadership

The Best Leaders Are Rethinking How They Spend Their Time

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The Best Leaders Are Rethinking How They Spend Their Time

Ask any executive what they’re short on in 2025, and they’ll say the same thing: time. Calendars are packed, decision fatigue is real, and meetings seem to multiply overnight. But quietly, some of the most effective leaders are doing something different—they’re auditing how they spend their attention, not just their hours.

Leadership today is not about doing more. It’s about choosing what matters most, and ensuring every hour reflects that priority.

Time Is the New Currency of Strategy

You can tell what a leader values by looking at where they show up—and where they don’t. The most strategic leaders are no longer attending every meeting, weighing in on every decision, or micromanaging every deliverable.

Instead, they’re focusing their time in three places:

  • People development: Coaching, mentoring, and unblocking talent

  • Foresight and pattern recognition: Zooming out to spot risks and opportunities early

  • Culture shaping: Reinforcing values through consistent behavior and communication

Everything else? Delegated. Automated. Or eliminated.

From Reactive to Intentional Leadership

The pace of business has made it easy for leaders to fall into reactive mode. But reaction isn’t strategy. When every day is spent putting out fires, no one is steering the ship.

The leaders who are rising above the noise are:

  • Setting boundaries around low-impact tasks

  • Using data to inform, not overwhelm

  • Trusting their teams to lead—and being clear about expectations

They treat their time like an investment portfolio—carefully allocated for long-term returns.

What This Signals to the Team

How a leader spends their time shapes the rhythm and priorities of the organization. If they’re always buried in emails, teams mimic that urgency. If they make time for learning, innovation, or 1-on-1s, that behavior becomes contagious.

Time isn’t just a resource—it’s a signal. And in today’s workplace, everyone’s watching.

3 Ideas to Take With You:

  1. Audit your calendar. Does it reflect your role—or your habits?

  2. Decide where you want to create the most value. Protect that time like your job depends on it.

  3. Lead by example. Your presence teaches people what to care about.

That’s the real work of leadership. Not doing more, but doing what matters—on purpose.

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Strategic Leadership

Everyone Wants to Be a Visionary. Few Know What It Actually Takes.

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Everyone Wants to Be a Visionary. Few Know What It Actually Takes.

In leadership circles, “vision” gets thrown around like a buzzword—mission decks, strategy retreats, motivational speeches. But in the real world of deadlines, turnover, and bottom-line pressure, vision alone isn’t enough.

The leaders making the biggest impact in 2025 aren’t just dreamers. They’re builders. They know how to translate abstract ideas into action, and they’re not afraid to make hard decisions when the roadmap changes.

So what separates the ones who talk about transformation from the ones who actually drive it?

They Know That Clarity Is More Important Than Charisma

It’s easy to inspire with a keynote or a punchy internal memo. What’s harder is consistently aligning people around a clear direction—especially when change is uncomfortable.

Strong leaders simplify the vision until every team member can answer three questions:

  • Where are we going?

  • Why does it matter?

  • What’s my role in getting us there?

They do it through repetition, context, and everyday decisions that reflect what they say they believe.

They Make Space for Feedback—And Know When to Push Through

Leadership in 2025 is less about popularity and more about balancing perspectives. The best leaders:

  • Invite dissent without defensiveness

  • Know when to pause for input and when to move forward with conviction

  • Build psychological safety without sacrificing standards

The goal is not to make everyone happy. It’s to make everyone feel heard, and then move with purpose.

They Build Teams That Outgrow Them

Legacy is not about control—it’s about capability. Forward-focused leaders measure their success by what happens when they’re not in the room. They:

  • Develop people who can think strategically on their own

  • Delegate authority, not just tasks

  • Reward growth, even if it means someone eventually leaves

These leaders aren’t afraid to build successors. They know sustainable impact depends on shared ownership.

From the Field: Three Questions to Ask Yourself This Week
To move from visionary to strategic, ask yourself:

  1. Have I said the same message three different ways so everyone on my team gets it?

  2. When was the last time I invited pushback and used it to sharpen our direction?

  3. Am I building a team that relies on me—or one that can rise without me?

You don’t need to lead a global company to lead with vision. You just need to show up with clarity, courage, and a plan that moves people—not just strategies that look good on slides.

And that’s the difference.

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