Contagious Culture – Details, episodes & analysis

In this episode of the Contagious Culture Podcast, Kyle King sits down with Dara Ashley, founding executive director of the Dara Ashley Foundation, researcher, and nonprofit leader working to close the access and exposure gap for underrepresented college students.

Dara shares how her own experiences, mentorship, and time at Howard University shaped her passion for helping students see what is possible. She explains why exposure matters, why students cannot pursue opportunities they have never seen, and how mentorship can change the trajectory of a young person’s life.

Kyle and Dara also discuss the difference between access and ability, the power of one-on-one mentorship, data-driven program design, Leadership U, and what it means to build an organization that helps students gain the skills, networks, and confidence they need for life after college.

Episode History

00:00 — Introduction 00:40 — Meet Dara Ashley 01:00 — Dara’s mission and infectious spirit 01:30 — Closing the access and exposure gap 02:30 — Helping students identify what they do not know 03:15 — The power of exposure 04:00 — Dara’s origin story and early mentorship experience 05:00 — Where to start if you want to serve your community 06:00 — Former mentees returning as mentors 07:15 — Access versus ability 08:45 — Why exposure also shows students what they do not want 10:00 — Dara’s path into research 11:00 — Why leaders must mentor and reach back 12:00 — Staying connected to the audience you serve 13:00 — What Dara saw missing in the system 14:30 — What leaders get wrong about mentorship 15:30 — The power of one-on-one mentorship 16:00 — What success looks like for Dara 17:00 — The ten-year vision for the Dara Ashley Foundation 18:00 — Growing into 42 states and going deeper locally 19:00 — Leadership U and student-centered program design 20:00 — Using data to measure and build impact 21:00 — Turning vision into systems and deliverables

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In this episode of the Contagious Culture Podcast, Kyle King sits down with Pedro Jose Rivera, a nonprofit fundraising strategist working at the intersection of law, philanthropy, wealth management, and nonprofit leadership.

Pedro shares how Latino-led nonprofits can move from grant dependency to deeper financial independence by building diversified fundraising systems. He explains why organizations need to focus on individual giving, planned giving, corporate support, board engagement, and community-based fundraising instead of relying only on restricted grants.

Kyle and Pedro also discuss the role of faith, family, generosity, board responsibility, peer-to-peer fundraising, and why asking for support is not begging. It is inviting people to invest in the mission.

Episode History

00:00 — Introduction 00:45 — Meet Pedro Jose Rivera 01:30 — Pedro’s Puerto Rican roots, family, faith, and education 03:40 — How generosity was modeled in Pedro’s childhood 06:00 — What Pedro hopes to give through his work 06:45 — Moving Latino-led nonprofits beyond grant dependency 07:40 — Understanding individual giving, planned giving, grants, and events 09:15 — Where new nonprofits should start fundraising 10:15 — Why nonprofits must think like entrepreneurs 11:30 — Why organizations become grant dependent 13:30 — Creative funding strategies and peer-to-peer fundraising 15:30 — What executive directors often overlook 16:50 — The role of the board in fundraising 18:45 — Why passion without systems is dangerous 20:30 — The fundraising truth leaders need to hear

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In this episode of the Contagious Culture Podcast, Kyle King sits down with Shola Richards, international keynote speaker, founder of Go Together Global, bestselling author, and host of the Kindness Extremist Podcast.

Shola shares the personal story behind his work and explains why kindness is not weakness. He opens up about pain, depression, imposter syndrome, and how his own wounds became the foundation for a global movement rooted in kindness, courage, and humanity.

Kyle and Shola also discuss the difference between being nice and being kind, why kindness requires boundaries and difficult conversations, and how leaders can create cultures where people feel safe, seen, and valued.

Episode History

00:00 — Introduction 00:24 — Meet Shola Richards 03:25 — The person behind the platform 06:30 — Why Shola does this work 08:30 — Pain, depression, and choosing kindness 10:54 — Why perfection is not required to lead 12:07 — Nice vs. kind 15:20 — How to embody kindness daily 16:24 — Boundaries, behavior, and difficult conversations 18:32 — Finding your voice through pain and healing 20:00 — Practical tools for the inner critic

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In this episode of the Contagious Culture Podcast, Kyle King sits down with Natalie Brown, Head of Strategic Workforce Partnership at Ally Financial, for a conversation on leadership, workforce development, strategic partnerships, and preparing the next generation for success.

Natalie shares how her work connects business goals, community priorities, and talent pipelines to create real opportunities for students, professionals, and future leaders. She also discusses the importance of mentorship, relationship-building, financial education, AI readiness, and partnerships rooted in shared values.

Kyle and Natalie explore what meaningful partnerships look like, why relationships matter in career growth, and how companies can build ecosystems that help people thrive.

Key Topics:

• What strategic workforce partnerships really mean
• How companies can build stronger talent pipelines
• Why partnerships must be rooted in shared values
• Preparing students for corporate America
• The role of AI skills in the future workforce
• Why mentorship and relationships matter
• How young professionals can build meaningful networks
• The importance of excellence, trust, and paying it forward

Episode History

00:00 — Introduction 00:12 — Meet Natalie Brown 01:30 — Who Natalie is beyond the title 03:10 — What keeps Natalie excited about the work 04:34 — Defining strategic workforce partnerships 06:20 — What meaningful partnerships look like 09:17 — Preparing students for future opportunities 11:20 — AI, prompting, and workforce readiness 13:20 — Why partnerships sometimes fail 16:30 — Mentorship, leadership, and advice that shaped Natalie 19:30 — The leadership traits young professionals need 21:30 — How to build and nurture relationships

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In this episode of the Contagious Culture Podcast, Kyle King sits down with Lindsey Fuller, Executive Director of The Teaching Well, leadership coach, keynote speaker, and organizational wellness consultant.

Lindsey shares why strong adult culture is the engine of strong student outcomes. She explains why schools cannot expect students to regulate, learn, and thrive if the adults leading them are burned out, unsupported, and disconnected from their own wellness.

Kyle and Lindsey also discuss educator burnout, adult behavior in schools, restorative leadership, the need to invest in teachers and school leaders, and what it would take to build school systems that are more human-centered, healing-centered, and sustainable.

Key Topics:

• Why adult culture shapes student outcomes
• How educator burnout impacts school communities
• Why schools need to invest in adults, not just programs
• The difference between a broken system and a sick system
• Why most school problems are adult problems
• Restorative leadership and repairing relationships
• The importance of therapy, coaching, and stronger benefits for educators
• Why school leaders need support, training, and accountability
• How philanthropy can better support educator wellness
• Building schools where adults stay whole so students can thrive

00:00 — Introduction 00:20 — Meet Lindsey Fuller 01:15 — Lindsey’s background and love of learning 02:30 — Childhood, trauma, and becoming a leader 03:30 — Teaching as inheritance 04:30 — School as both sanctuary and harm 05:30 — What it means to build human-centered schools 06:00 — Why the education system is sick, not broken 07:30 — What practices need to be preserved or reimagined 08:45 — Critical hope and why children keep Lindsey hopeful 09:30 — Where school change begins 10:30 — Why most school problems are adult problems 11:30 — Adult behavior, regulation, and school culture 13:00 — Why schools must invest in educators 14:30 — Educator mental health as a public health crisis 16:30 — Caring for the caregivers 17:00 — What Lindsey would change if she had the keys 18:00 — Coaching, therapy, benefits, and professional development 19:30 — Funding, accountability, and philanthropy 20:30 — Why teachers and school leaders are the key levers 21:30 — Seeing the full puzzle of school transformation

Lindsey Fuller is the Executive Director of The Teaching Well, a leadership coach, keynote speaker, and organizational wellness consultant. Her work focuses on helping schools and districts build strong adult culture, improve educator wellness, strengthen leadership practices, and create environments where adults can stay whole so students can thrive.

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In this episode of the Contagious Culture Podcast, Kyle King sits down with Olivia Jefferson, VP of Social Impact at Best Buy and a leader helping drive the vision of the Best Buy Foundation.

Olivia shares how her personal story, her mother’s resilience after a life-changing accident, and her early exposure to philanthropy shaped her purpose and commitment to community impact. She explains why philanthropy is not just about moving dollars, but about stewarding resources in ways that change lives, open doors, and create lasting opportunity.

Kyle and Olivia also discuss corporate philanthropy, authentic partnership, youth workforce development, durable skills, AI, mentorship, accountability, skills-first hiring, and how the Best Buy Foundation is helping young people move from access to technology toward economic opportunity and mobility.

Key Topics:

• Olivia’s journey into philanthropy and social impact
• How her mother’s resilience shaped her purpose
• Why corporate philanthropy can drive meaningful community change
• The weight of leading impact work from inside a corporation
• What Olivia had to unlearn to become the leader she is today
• Trusting yourself as a leader
• The importance of coaching, accountability, and repair
• Why durable skills matter in the future of work
• How AI is changing workforce preparation
• Why relationships, curiosity, and critical thinking still matter
• What strong partnership looks like beyond the grant dollar
• How funders can reduce friction for nonprofit partners
• Best Buy Foundation’s work around technology, mentorship, and economic mobility

00:00 — Introduction 00:30 — Meet Olivia Jefferson 01:15 — Kyle shares Olivia’s impact on his leadership 02:00 — Who Olivia is outside of work 03:00 — Family, friendship, mentorship, and community service 04:30 — The journey that shaped Olivia’s values 05:30 — Olivia’s mother’s accident and resilience 07:00 — Learning the power of grants and philanthropy 08:30 — Discovering philanthropy through the Kresge Foundation 09:45 — Purpose and corporate philanthropy 11:00 — Carrying the weight of impact work 12:30 — Why people like Olivia need to be in corporate spaces 14:30 — Unlearning ego in impact work 15:15 — Learning to trust yourself as a leader 16:30 — Leading young and growing through responsibility 18:30 — The importance of coaches, sponsors, and advocates 20:00 — Accountability, repair, and leadership growth 22:00 — Are young people ready for the workforce? 23:00 — Skills-first hiring and economic mobility 24:30 — Durable skills and the automation of entry-level work 27:30 — Where jobs are going and how young people can prepare 28:30 — Relationships, curiosity, communication, and critical thinking 30:30 — AI as a resource, not a replacement 31:00 — What real partnership looks like 32:00 — Supporting nonprofits beyond the grant dollar 35:30 — Vetting partnerships and reducing wasted time 38:00 — Why nonprofits should not shape-shift for funding 40:30 — Best Buy Foundation’s work in community 41:30 — Tech-reliant careers, skills, and credentials 43:00 — Teen Tech Centers and preparing young people early 44:30 — The next generation of community impact leaders 46:30 — Corporate philanthropy aligned with business strategy 48:00 — Where to connect with Olivia and Best Buy Foundation

Olivia Jefferson is the VP of Social Impact at Best Buy and a leader helping drive the vision of the Best Buy Foundation. Her work sits at the intersection of corporate citizenship, community partnership, youth opportunity, technology access, mentorship, and workforce development. Through her leadership, Olivia helps create pathways that support young people as they move from access to technology toward economic opportunity, mobility, and real-world career exposure.

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In this episode of Contagious Culture, Kyle S. King sits down with Claire Masikewich, founder of the Strong Like Sloan Foundation, for a powerful conversation about purpose, adversity, storytelling, community, and turning pain into impact.

After her daughter Sloan was diagnosed with stage four cancer at five and a half years old, Claire’s life and work shifted. What started as a way to cope became a foundation raising money, awareness, and advocacy for pediatric cancer research.

Claire shares how her family navigated treatment, relapse, remission, and hope while building a nonprofit that has raised nearly $400,000 in less than three years. This episode is for nonprofit leaders, parents, founders, and changemakers who are trying to build something meaningful while carrying the weight of real life.

00:00 — Welcome to the Contagious Culture Podcast 01:00 — Claire Masikewich’s background in marketing and communications 02:30 — Sloan’s diagnosis and the start of Strong Like Sloan 05:00 — Finding purpose without forcing purpose 07:00 — The vision: a world where pediatric cancer is cured 09:30 — Why nonprofits should focus on solving root problems 12:00 — The challenge of funding pediatric cancer research 14:30 — Raising nearly $400,000 through community and storytelling 17:00 — How to tell powerful stories when the story is not your own 19:00 — Turning adversity into action 21:00 — “What if it all works out?” 23:00 — What kept Claire going during the hardest seasons 25:00 — The lesson of capability: we are stronger than we think 27:00 — The role of community in survival and impact 29:00 — Letting go of what you cannot control 30:30 — Boundaries, balance, and learning to say no 31:30 — Claire’s message to leaders and changemakers 32:00 — Closing: What type of culture are you spreading?

Strong Like Sloan Foundation Instagram: @stronglikesloane

Claire Masikewich Instagram: @therealclairem

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In this episode of the Contagious Culture Podcast, Kyle King sits down with Lauren Riley, Executive Director of Gratitude Network, to talk about nonprofit leadership, culture, sustainability, and scaling impact.

Lauren shares why passion alone is not enough to grow an organization. Nonprofits need clear systems, aligned messaging, strong leadership, and a value proposition that everyone on the team can communicate.

Kyle and Lauren also discuss why values are not culture, why organizations cannot scale what is not sustainable, and how nonprofit leaders can build systems that outlast the founder or executive director.

Episode Highlights

00:00 — Introduction 01:16 — What keeps Lauren’s fire burning 02:00 — What Gratitude Network does 03:10 — What nonprofits often get wrong 04:44 — Building systems beyond the leader 06:18 — Why behaviors define culture 10:32 — Coaching, mentorship, and performance 13:15 — Recovering from disruption and defeat 15:48 — Moving beyond grants and donor dependency 18:26 — Training your team to communicate value 28:36 — Product, distribution, and financial sustainability 30:03 — Closing reflections

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In this episode of the Contagious Culture Podcast, Kyle King sits down with Peggy Doherty DeLong, Psy.D., a psychologist, speaker, and educator who teaches practical tools for gratitude, well-being, and personal fulfillment.

Peggy shares how gratitude helped her through deep grief after losing her fiancé and father within weeks of each other. She explains the science behind gratitude, why it is most powerful on our hardest days, and how simple daily practices can improve our mental health, relationships, and sense of meaning.

Kyle and Peggy also discuss the power of handwritten notes, awe, nature, human connection, the PEACE Method, and how high achievers can redefine success without burning out.

Episode Highlights

00:00 — Introduction 00:55 — Peggy’s story and work with gratitude 02:35 — The science behind gratitude 04:29 — Daily gratitude practices 06:20 — The power of handwritten letters 08:00 — Gratitude, simplicity, and emotional blocks 10:21 — Starting the day with simple practices 11:21 — Finding awe in everyday life 13:14 — Nature, healing, and mental health 15:00 — Man’s Search for Meaning and resilience 16:48 — Defining meaning through connection 17:16 — The PEACE Method 20:08 — Redefining achievement 21:36 — The three P’s: pleasure, present, purpose

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In this episode of the Contagious Culture Podcast, Kyle King sits down with Christine Robertson, a nonprofit technology and data professional with more than 20 years of experience helping mission-driven organizations strengthen their impact through better systems, strategy, and technology.

Christine explains why nonprofit data should not be treated as administrative busywork. When managed well, a CRM can preserve donor relationships, strengthen fundraising, improve communication, protect institutional knowledge, and give organizations a clearer picture of the people who support their mission.

Kyle and Christine also discuss data security, clean data, selecting the right technology, consolidating information into one source of truth, maximizing the tools an organization already owns, and why buying new software will not solve a broken process.

Key Topics:

• How technology can strengthen donor relationships
• Why every organization needs one source of truth
• The danger of keeping donor information in inboxes and spreadsheets
• How staff turnover can disrupt donor relationships
• Choosing technology based on organizational priorities
• Why organizations often underuse the tools they already have
• Training problems versus software problems
• Why a new tool cannot fix a broken system
• Treating database professionals as fundraisers
• Protecting donor information and maintaining trust
• What clean data actually means
• Where organizations should begin cleaning their data
• Using email engagement data to improve communication
• Starting with small, strategic steps instead of fixing everything at once

00:00 — Introduction 00:15 — Meet Christine Robertson 00:55 — What is exciting Christine about technology 01:45 — Technology, fundraising, and relationships 02:30 — How the nonprofit technology landscape is changing 03:00 — Why donor information cannot live in one person’s head 03:30 — Using a CRM to preserve organizational relationships 04:00 — The first step toward better data management 04:30 — Creating one consolidated source of truth 05:00 — The problem with disconnected email, event, and donation tools 06:00 — Documenting every donor interaction 06:45 — Why CRM work is not busywork 07:00 — Technology options for grassroots organizations 08:00 — Choosing software based on priorities 09:30 — Integrations, email tools, and non-negotiable features 10:00 — Why organizations underuse the software they own 10:30 — Training problems versus system design problems 11:30 — When it may actually be time to change tools 12:00 — A new tool will not fix a broken system 12:30 — The people behind the technology 13:00 — Treating data professionals as fundraisers 13:30 — Why data management should not be an afterthought 14:30 — Donor data security and organizational responsibility 15:00 — Protecting donor trust and sensitive information 16:00 — Guarding donor information like your own 16:30 — What clean data really means 17:30 — Why clean data does not mean perfect data 18:00 — Starting with the pain point that hurts the most 18:30 — Building weekly, monthly, and annual data routines 20:00 — Recognizing when your organization needs help 21:30 — Why nonprofit strategy often lives in the gray 22:00 — The myth that some people cannot learn technology 23:30 — Why data is the foundation of nonprofit growth 24:30 — Using donor behavior to personalize relationships 25:00 — Underused email marketing insights 26:30 — How often leaders should review their data 27:30 — Asking the right questions before analyzing data 28:30 — Avoiding overwhelm and running your own race 29:30 — Practical advice for leaders who want to scale 30:00 — Documenting organizational pain points 30:30 — Making time to improve systems 31:00 — Fixing problems one at a time 32:30 — Where to connect with Christine 33:00 — Humanitru and supporter management

Christine Robertson is a nonprofit technology and data professional with more than 20 years of experience helping mission-driven organizations strengthen fundraising, improve donor relationships, and build better systems. She began her career as a nonprofit database manager and has since worked inside organizations and as a consultant, helping teams use data, strategy, and technology to amplify their impact.

Christine also works with Humanitru, a supporter management platform designed to help nonprofits consolidate donor, event, membership, email, and engagement information into one place.

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