Lead the Ask
Lead the Ask
Holly Kobia
Most nonprofit leaders would rather do anything but ask for money. Lead the Ask exists to change that. Hosted by Holly Kobia, founder of Kobia Consulting and a fundraising strategist with 20+ years of experience leading teams that have raised over $100 million, this podcast hands nonprofit leaders the structure, strategy, and confidence they need to stop freezing and start leading.
The State of Giving: Where Smart Nonprofits Are Putting Their Energy in 2026
Americans gave nearly $600 billion to charity in 2024 — so why are so many nonprofits still struggling to hit their fundraising goals? Holly Kobia breaks down the latest Giving USA data and what it actually means for your organization as you plan for the year ahead.She walks through five major giving trends — from the concentration of wealth among high-capacity donors, to the growing importance of planned giving, to why corporate sponsorships are getting way too much attention from small nonprofits. (Spoiler: individuals still account for two-thirds of all charitable giving. Are you spending two-thirds of your time there?)You'll walk away with three concrete things to focus on: building a donor pipeline, developing a board that opens doors, and creating a stewardship system that keeps donors coming back. The money is out there. The question is whether your organization is positioned to receive it.
Jun 30
21 min
Stewardship as Donor Retention Strategy | Lead the Ask Bonus Episode
If you could double your fundraising without finding a single new donor, would you be interested? Most nonprofits are leaking donors faster than they're acquiring them. And the biggest growth opportunity you have is already sitting in your donor database.In this bonus episode, Holly breaks down why stewardship isn't just a thank you letter — it's your most important fundraising strategy. You'll hear why donor retention is the hidden crisis we've all accepted as normal, how to build a simple A/B/C donor category system, the four levels of stewardship that actually move the needle, and why donors leave quietly (and what we can do about it). The people who've already said yes to your mission deserve your attention first. The next gift often begins the moment the last gift is received.
Jun 25
13 min
Your Fundraising Problem Isn't Donors — It's Leadership
Most nonprofits think they have a fundraising problem. More donors, more events, more staff — that's what they're after. But after years working in fundraising, communications, and leadership, Holly Kobia has a different diagnosis: the real problem starts at the top.In this debut episode of Lead the Ask, Holly breaks down why fundraising is a leadership issue — not a development department issue — and what that means for your organization's culture, clarity, and consistency. From the habits that quietly undermine donor relationships to the systems that high-performing nonprofits swear by, Holly gets real about what's holding your fundraising back and exactly what to do about it.In this episode:Why fundraising culture lives inside leadership, not the development officeThe most common mistakes leaders make (and don't realize they're making)How to move from reactive fundraising to a steady, confident rhythmWhat strong fundraising organizations do differentlyThis week's challenge: take an honest look in the mirror at your fundraising cultureLead the Ask is for nonprofit leaders, fundraisers, and board members who are ready to skip the fluff and do the real work of fundraising.Follow Holly on LinkedIn | @leadtheask on Instagram | New episodes drop the last Tuesday of every month.
May 26
20 min
Lead the Ask Introduction
Fundraising gets easier when leadership gets clearer. Lead the Ask is the podcast for nonprofit leaders, fundraisers, and board members who are done guessing their way through fundraising and ready to do the real work.Host Holly Kobia — former TV journalist turned fundraising professional with $100M raised at Virginia Tech — cuts through the fluff and gets into what fundraising actually looks like day to day. We're talking practical strategy, donor psychology, board empowerment, major gifts, stewardship, and the hard conversations nobody else wants to have.Because fundraising isn't about asking for money. It's about inviting people into something bigger than themselves, and leading them there with clarity and confidence.Here, we'll lead boldly, ask clearly, and fund that mission.
May 22
8 min