Investing in Kindness: 75 Interview Review

Investing in Kindness was inspired by a question I was asked during an innovation panel at SXSW at the German Haus. I used the phrase “Invest in Kindness” and after the panel I decided to research how kindness influences leadership, investing, and business outcomes. Between March through October, I completed 75 interviews.

In August, I published Investing in Kindness: 25 Interview Review, summarizing insights from the first 25 interviews conducted between March and May. Those interviewees represented the United States, Brazil, Bangladesh, Germany, Italy, Nigeria, Canada, Colombia, Congo, India, Switzerland, Taiwan, Venezuela, and Uganda. Their roles spanned wealth management, content creation, education, technology, healthcare, and executive leadership. Across industries and geographies, participants described kindness as a core leadership principle influencing trust, decision-making, and long-term outcomes.

In October, I published Investing in Kindness: 50 Interview Review, reflecting interviews 26 through 50 conducted between May and July. This group included participants from the United States, Bolivia, Brazil, Denmark, Dominican Republic, France, Iran, Israel, Italy, Lebanon, Nigeria, and Romania. Their backgrounds ranged from strategy and executive leadership to decarbonization, coaching, education, and investment. The second cohort expanded the discussion into capital allocation, governance, and cultural accountability.

Interviews 51 through 75, completed between July and October, include participants from Germany, the United States, England, Singapore, Canada, Vietnam, and Slovenia. Roles span former Fortune 500 executives, archaeologists, neuroscientists, sustainability leaders, entrepreneurs, real estate operators, AI founders, and community builders.

At this stage, the research is less focused on whether kindness matters and more focused on how it is embedded into systems, measured in practice, and operationalized in leadership, investment decisions, and organizational design.

Reoccurring Themes Across 75 Interviews

Across 75 global interviews spanning executives, founders, investors, technologists, scientists, educators, and community leaders, several patterns consistently emerge.

• Kindness is defined as clarity. Leaders consistently distinguish kindness from niceness. Kindness includes direct communication, honest feedback, and transparency delivered with respect. In some contexts, directness is considered the most respectful approach. In others, honesty is expressed through hospitality, ritual, or relational framing. Across interviews, truth delivered with dignity is a common thread.

• Trust is built through behavior. Interviewees describe trust as something earned through consistent actions. Leaders referenced deliberate meeting practices, preparation before entering new environments, acknowledgment of individual contribution, and follow-through on commitments. Psychological safety emerges when people feel safe to speak, take risks, and admit mistakes without fear of negative consequences.

• Accountability and compassion are not in conflict. High standards and empathy appear together. Leaders describe holding others to expectations because they believe in their potential. Mentorship is framed as responsibility. Several participants emphasized that time is a leader’s most finite resource, and choosing to invest it in others is one of the clearest expressions of care.

• Kindness strengthens loyalty and retention. Leaders described transparent and respectful cultures as creating long-term commitment, even during periods of stress or uncertainty. Toxicity, by contrast, was repeatedly described as destabilizing and costly.

• Leadership begins with internal regulation. Self-awareness, composure under pressure, and emotional regulation were described as prerequisites for sustainable leadership. Several participants connected self-kindness and healing to stable external leadership behavior. Leaders noted that insecurity often manifests as defensiveness or aggression in organizational settings.

• Capital reflects values. Investment and governance decisions reveal what organizations prioritize. Interviewees described community-owned systems, including food cooperatives that reinvest profits locally, and ownership structures designed to prevent short-term extraction. Kindness in these contexts appears in how incentives are aligned and who benefits from growth.

• Technology carries moral design choices. Leaders building AI and advanced technologies describe embedding fairness, transparency, and human-centered principles into product architecture. In one case, a founder explicitly framed the work as teaching AI what it means to love. Ethical design is treated as a responsibility, not an afterthought.

• Cultural humility requires preparation. Interviewees working across borders and in high-risk environments described kindness in practical terms: researching local customs, deferring to local expertise, acknowledging shared risk, and correcting mistakes quickly. Respect is demonstrated through preparation, not assumption.

• Attention shapes culture. Several leaders emphasized that what is noticed, rewarded, and reinforced becomes the culture. Kindness is expressed through what leaders prioritize publicly and privately.

After 75 interviews, kindness appears most clearly in five operational areas:

• It shows up in how leaders communicate under pressure.
• It shapes how capital is allocated.
• It influences how technology is designed.
• It determines whether governance structures are extractive or reinvested.
• It affects how teams experience accountability and feedback.

Across interviews, kindness consistently appears alongside disciplined decision-making, high standards, and long-term thinking. Leaders repeatedly connect it to trust, resilience, and sustained performance.

Kindness is a daily decision. It may prove to be one of the most practical investments we can make.