In this Seven Questions episode, Martín Diego Garcia sits down with Denise Feriozzi, co-founder and executive director of Pipeline Fund, to talk about building the long-term, down-ballot infrastructure progressives have needed for years. She breaks down the gaps Pipeline Fund set out to fill and digs into the realities of this work today, from rising safety and security concerns to the case for contesting races everywhere, not just in swing states.

Guest Info:

Denise Feriozzi, Co-founder and Executive Director, Pipeline Fund.

Sign up for The Baseline, Pipeline Fund's monthly newsletter, here.

Check out Denise's recommendations:

TV: Below Deck (Peacock/Bravo)

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In this episode, Joe sits down with Cesar Toledo, Executive Director of the Wanda Alston Foundation, to talk about what it really looks like to make local impact. Cesar shares his journey from national politics — including the Harris-Walz campaign and the LGBTQ+ Victory Fund — to leading a small but mighty DC nonprofit serving homeless LGBTQ+ youth, where nearly 40% of DC's homeless youth identify as queer. He and Joe dig into how Cesar is scaling impact with limited staff, why campaign skills translate directly to nonprofit leadership, and how he refuses to let the opposition steal his joy.

Guest Info:

Cesar Toledo, Executive Director, Wanda Alston Foundation

Connect with Cesar on Instagram (@chico_ces)

Resources:

• The Wanda Alston Foundation's housing programs
• Cesar's 2025 Out100 feature
• Cesar's Metro Weekly cover story
• LGBTQ+ Victory Institute candidate and campaign trainings

Check out Cesar's recommendations:

TV: Invincible (Amazon Prime)

Movies: George A. Romero's Dawn of the Dead and the Resident Evil film franchise.

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What does it actually mean for a bank to be "socially responsible," and why should every nonprofit, campaign, and advocacy organization care? In this episode, Martín sits down with Maura Keaney, Vice President and Director of Client Engagement at Amalgamated Bank, to unpack what ethical banking looks like in practice. Maura shares how a bank can be a real partner in the progressive movement. She also gets into the practical stuff: ACH payments, fraud prevention, payment strategy, and the questions every executive director or CFO should be asking their banking partner.

Guest Info:

Maura Keaney, Vice President and Director of Client Engagement at Amalgamated Bank, America's socially responsible bank.

Connect with Maura on LinkedIn.

Check out Maura's recommendations:

Books: Tana French and Emily St. John Mandel both have new books hitting the shelves!

TV: Slow Horses and Ted Lasso (both on Apple TV+)

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In this special 7 Questions episode, Joe sits down with Kristen Grimm, Founder and Strategist at Spitfire Strategies, for a candid conversation about what it takes to win a campaign right now. Kristen unpacks common strategic-planning mistakes: vague milestones, the "build the plane while we're flying it" approach, and the obsession with one giant "big tent" coalition. She and Joe also dig into why so many strategic plans sit on a shelf, what AI is changing about the speed of campaigns, and why the most important question in your planning meeting may be what you're for, not just what you're against.

Guest Info:

Kristen Grimm, Founder and Strategist at Spitfire Strategies.

Connect with Kristen on LinkedIn.

Resources:

• Planning to Win — Spitfire's updated campaign planning guide and tool
• Replenishing Trust — Kristen's guide on rebuilding civic trust through interactivity, not just transparency

Check out Kristen's recommendations:

• Book: Don't Burn Anyone at the Stake Today by Naomi Alderman
• TV: Vladimir (Netflix) and Rooster (HBO / HBO Max)

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In this bonus episode of How to Win a Campaign, host Martín Diego Garcia shares a webinar recorded in September 2025 featuring two innovative leadership development programs working to solve one of campaigns' most persistent problems: what happens to great talent between election cycles. Martín sits down with Theo LeCompte of Loft Leaders and Lorenza Ramirez of Blue Line Fellows for a deep dive into how both programs are investing in the next generation of political and advocacy leaders. Whether you're a campaign staffer navigating the off-year gap, an organization looking to hire mission-driven talent, or someone curious about how progressive campaigns are developing their bench, this conversation is packed with practical insight. Both guests share how their programs work, what they look for in fellows, and how employers and mentors can get involved.

Guest Info:

Lorenza Ramirez, Founder, Blue Line Fellows. Blue Line bridges the gap between election cycles by placing top campaign talent into meaningful roles, while building their networks and skills ahead of future cycles and beyond. Learn more at bluelinefellows.com.

Theo LeCompte, Executive Director, Loft Leaders. Loft is a fully paid, year-long fellowship that provides up-and-coming leaders in campaigns and public service with access to a graduate business education. Loft gives fellows the opportunity to deepen their network and build a stronger foundation for future opportunities. Learn more at loftleaders.org.

Resources:

• Arena
• TCW Blog: How to Land Your First Political Internship
• TCW Blog: Job Banks and Boards for Political Careers

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Joe and Martín are back to give listeners a sneak peek at what's coming in Season 5's bonus episodes. From ethical banking and mental health policy to DC voting rights and the future of advocacy, this season's lineup is packed with timely, practical conversations from some of the sharpest minds in politics and advocacy. We're also sharing a few webinar recordings — including an exclusive goal-setting training from our TCW Advocacy series. This bonus season is a must-listen, whether you're a seasoned campaigner or just getting started.

In our final regular episode of Season 5, Heather Booth returns to share more of her journey and insights into organizing and activism, as well as the need for love and joy in sustaining long-term activism. Joe and Heather discuss the challenges of staying organized and the importance of maintaining personal connections and joy in their work.

Guest Information:

You can connect with Heather on LinkedIn or on her website.

Check out some of Heather's recommendations:

Books:

• The Hard Work of Hope (Michael Ansara)
• Working 9 to 5: A Women's Movement, a Labor Union, and the Iconic Movie (Ellen Cassedy)

Movies

• The Janes (HBO Max)
• Freedom On My Mind (Vimeo)
• Salt of the Earth (Prime Video)
• Z (Criterion)
• Sinners (HBO Max)
• Heather Booth: Changing the World (Amazon)
  

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Presented by The Campaign Workshop.

In this episode, Joe chats with Cheryl Contee about AI’s impact on nonprofits. Cheryl discusses her book, “AI for Nonprofits,” emphasizing the importance of using AI to enhance work and make a greater difference. She also addresses concerns about AI ethics and environmental impact, advocating for transparency and responsible use. If you’ve got questions about AI, this is the episode for you!

Guest Information:

You can connect with Cheryl on LinkedIn. You can check out Cheryl's book, AI for Nonprofits here.

Some of the websites and AI tools mentioned in Cheryl's interview include:

• Change Agent
• AI4NP
• NTEN
• There's An AI For That

Cheryl's recommendations:

TV:

• Star Trek (Paramount+ and other platforms)

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Presented by The Campaign Workshop.