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10 Examples of How Highly Admired Entrepreneurs Show Empathy

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You secretly envy celebrity entrepreneurs. Their prosperity is as inspiring as how they became wildly popular. There’s one extraordinary trait among these entrepreneurs who serve massive audiences, elevating their empathy gift.

Empathy benefits for high achievers come from careful reflections. Examples of their empathetic nature reveal insights YOU can copy. Insights that bond you closer with your audience.

Here are 10 benefits and insights of admired, empathetic entrepreneurs:

1. Earning loyal fans through vulnerability

The ‘Bufferoos’ of Buffer openly communicate they value and care about their staff and audience.  

Tuning into his empathetic mindset, co-founder Joel Gascoigne knows fans appreciate vulnerably disclosing business mistakes. They empathize with the team’s painful loss.

The mistakes we make don’t just affect product features. They affect people’s lives. No amount of optimism could prepare Buffer when we had to tell 10 talented teammates their journey with us was over.” – Joel Gascoigne

2. Creating virtual interactive experiences from reciprocal comments

Either Jon Morrow or his Smart Blogger’s guests hang out in the blog comments on publishing day. Jon and his team are empathetic pros at offering what their audience wants. In exchange for loyalty, blog fans receive personal replies, free advice, recognition, and blog topic input. Loyal fans eagerly await their weekly virtual conversations.

3. Considering online visitors’ point of view

Brian Carroll, Founder of B2B Lead Blog stresses that new customers and website visitors want to be treated as people –not as leads, email addresses, traffic, or conversions. Brian’s empathetic advice for content access considers online visitors’ point of view.

Use your empathy and put yourself in your customer’s shoes. People use the web and social media for research; they’re looking for fresh ideas, insight, and actionable information. That’s why you shouldn’t put your best thinking behind web forms and registrations pages.” – Brian Carroll.

4. Mastering attention-grabbing among a sea of choice

The head of I Will Teach You to be Rich, Ramit Sethi writes email subject lines by tapping into his empathetic ability. He understands what subjects evoke his readers’ emotions and curiosity. Later, readers are tempted to respond to Ramit’s thought-provoking questions.

Would YOU reply to these? Subject: “What I believe but cannot say” Email closure: “P.S. Just for fun: What do YOU believe that you cannot say? Hi reply and tell me. I’ll keep it anonymous if you want me to.” Ramit Sethi

5. Adding fireworks to empathy

Marie Forleo combines her contagious personality and empathetic charm. Drawing upon her contagious audience connection –Marie shares tough, heartfelt advice for motivating her audience. “Test your ideas in private so you don’t publically announce every time you’re going to try something new.” Marie Forleo

6. Fully revealing discoveries at no cost

Pat Flynn from Smart Passive Income reveals his proven results without charging his audience. Communicating openly –from income reports to business processes is what empathetic Pat knows his audience loves. He speaks from his inner self when sharing opinions and advice.

RAOK = random acts of kindness. You should do something to acknowledge that a reader or viewer did a RAOC for you. Perform your own ROACK. Randomly reply to a comment by reading it out and sharing with your viewers or readers.” – Pat Flynn

7. Matching your audience’s reality and perspective

Jill Smokler with Scary Mommy understands and lives her mom readers’ reality. Readers crave the relatable blog topics. They resonate with the emotional tone. Scary Mommy’s empathetic perspective unites their readers. It matches what they believe and value: Parenting doesn’t have to be perfect to be ideal. “All of the parties I didn’t get invited to as a kid came flooding back.” Jill Smokler

8. Enhancing what’s most appealing for your audience

Joel Brown with Addicted2Success understands what empowers and inspires his ambitious audience. He shares inspirational wisdom through his success secrets, along with discoveries from interviewing wildly prosperous people. Joel’s empathetic talent keeps viewers coming back. They’re treated to watching Joel discuss prosperity habits surrounded by breath-taking, exotic scenery. 7 million dollar habits Joel reveals from super high achievers…

First thing in the morning knock out high, heavy tasks as your willpower is high. Daily exercise heightens activity in your prefrontal cortex. This part of your brain is used for making executive decisions.  Visualization helps your goal setting direction.” – Joel Brown

9. Turning emails into privileged conversations

Chris Brogan personally and promptly replies to hundreds of weekly emails from his exclusive tribe. Reading these responses heightens Chris’ empathetic view. By drawing attention to tribe members’ updates and accomplishments –Chris unites his members.

Believe it or not, just by electing to receive this letter, I consider you part of my monchu. I’m lucky to have you in this one family.” Chris Brogan

10. Impacting people’s lives through trust

Larry Page of Google relies on his empathetic character for prioritizing users’ high privacy values.

Approval for beneficial access should respect people’s informed privacy rights. Trusting beneficial privacy requests could have life-altering results, i.e. exclusive medical treatment.

And when someone accesses your medical record, a research doctor, you could see which doctor accessed it and why. You could maybe learn about what conditions you have. I think if we just did that, we’d save 100,000 lives this year.” – Larry Page

Marketing has evolved since these empathetic entrepreneur celebrities were becoming affluent. There are substantially more options for customers. While mapping out your entrepreneur success journey, put on your empathy glasses.

Elevating your empathy gift deepens the human connection with your audience and customers. This connection strengthens trust for bonding with you. Contemplate the insights how celebrity empathetic entrepreneurs bonded with their audience.

Which insight will accelerate your success journey? Leave your comments below!

Keri Vandongen, R. SLP, has a dual focus for online communication and empathy marketing. She guides entrepreneurs from tuning into audience insights to earning continuous loyal customers. You’re welcome to connect with Keri through her website www.earnloyalcustomers.com.

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Business

The Entrepreneur’s Reading List That Transforms Ideas Into Empires

These must-read titles and writing insights reveal how entrepreneurs turn bold ideas into empire-level success.

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Entrepreneurship is powered by stories—of accomplishment, failure, and decision moments that define businesses. Books are maps, providing insight from individuals who’ve traversed the road ahead. (more…)

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The Leadership Shift Every Company Needs in 2025

Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

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Bridging the gap between employees and employers
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In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”

While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.

Why This Gap Exists

Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.

What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.

Tools and Techniques to Bridge the Gap

Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.

1. Practice Mutual Empathy

Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.

2. Maintain Professional Boundaries

Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.

3. Follow the Golden Rule

Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.

4. Avoid Micromanagement

Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.

5. Empower Employees to Grow

Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.

6. Communicate in All Directions

Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.

7. Overcome Insecurities

Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.

8. Invest in Coaching and Mentorship

True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.

9. Eliminate Favoritism

Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.

10. Recognize Efforts Promptly

Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.

11. Conduct Thoughtful Exit Interviews

When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.

12. Provide Leadership Development

Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.

13. Adopt Soft Leadership Principles

Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.

The Bigger Picture: HR’s Role

Mercer’s global research highlights five key priorities for organizations:

  • Build diverse talent pipelines

  • Embrace flexible work models

  • Design compelling career paths

  • Simplify HR processes

  • Redefine the value HR brings

The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.

Treat Employees Like Associates, Not Just Staff

When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.

Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.

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When you think of Richard Branson (Virgin Group), Bill Gates (Microsoft), Steve Jobs (Apple), Rupert Murdoch (News Corporation), and Ted Turner (CNN), one thing becomes clear: they are not just entrepreneurs, they are entrepreneurial leaders. (more…)

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Learn essential lessons, success strategies, and mindset shifts every aspiring entrepreneur needs to overcome challenges and build a thriving business.

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