Lead the Ask Podcast
with Holly Kobia
Most nonprofit leaders would rather do anything but ask for money. Holly Kobia makes fundraising clear, less scary, and finally doable—with real best practices that actually work.
The Problem
Most Nonprofit Leaders Are Avoiding the One Thing That Funds the Mission
Because fundraising feels scary, pressurized, and deeply personal. You care about the mission, but the moment the ask gets real, everything tightens up—awkwardness, self-doubt, fear of rejection, and the sense that you’re putting your integrity on the line.
Lead the Ask is the antidote: real structure, real strategy, and no fluff. It gives nonprofit leaders a way to stop freezing, start leading, and ask with clarity and confidence.
Sound Familiar?
- You avoid the ask until it's urgent
- Your board doesn't know their fundraising role
- You feel awkward talking about money
- You want results, but don't have a clear plan
What We Cover
These are the fundraising conversations most nonprofits never have—but desperately need. From board accountability to the ask itself, we tackle the hard stuff head-on so you can stop guessing and start leading.
Your Board Isn't Fundraising. Yet.
Your board can show up to meetings and still leave the fundraising to you. We talk about how to move them from present to proactive.
Stop Reacting. Start Planning.
When fundraising is reactive, everything feels like a scramble—no plan, no pipeline, no predictability. Planning changes that.
Know Who to Ask. Know When.
If you don’t know who to ask, when to ask, or how to move someone forward, fundraising stalls. We show you how to build momentum.
The Moment Everyone Dreads.
This is the moment everyone dreads: the ask. We help you get through the fear and make it with clarity, confidence, and conviction.
More Topics We Dig Into
Getting the Gift Is Just the Beginning.
Too many nonprofits celebrate the donation—and then go silent. Donors notice when the thank-you fades fast, and that silence can quietly undo trust, momentum, and future giving.
Your Best Donors Are Your Past Donors.
While everyone chases new names, the biggest opportunity is sitting right in front of you. We dig into how to re-engage the donors you already have and turn overlooked relationships into real growth.
The Stuff Nobody Wants to Say Out Loud.
This is where Holly goes where other podcasts won’t: the dysfunction, the avoidance, the excuses, and the uncomfortable truth behind why fundraising underperforms. It’s blunt, honest, and weirdly relieving to hear.
Our Philosophy
No Fluff. No Fear. Just What Actually Works.
This isn't another podcast chasing noise, empty inspiration, or "fundraiser of the week" energy. Holly cuts through the hype with real best practices, hard truths, and practical guidance that makes fundraising feel clear, doable, and less intimidating.
Structure over Scrambling
Lead with a clear plan, not last-minute panic. Build a fundraising rhythm your whole team can actually follow.
Leadership over Luck
Strong fundraising comes from leaders who set direction, model the work, and take ownership of results.
Strategy over Noise
Ignore the trends. Focus on the fundamentals, the hard stuff, and the decisions that drive real results.
Action over Theory
Leave with clear next steps, not vague motivation—so you can put the ideas into practice right away.
Meet Your Host
Holly Kobia
Holly Kobia is the founder of Kobia Consulting and a fundraising strategist and journalist with more than 20 years of experience. She has led teams that have raised more than $100 million and now works with nonprofit leaders to build clear strategies, strengthen donor pipelines, and lead fundraising with confidence.
Her approach is simple: When leadership gets clearer, fundraising gets easier. Every episode of Lead the Ask reflects that belief—practical, honest, and built for real results.
20+
Years of Experience
$100M+
Raised
What You'll Walk Away With
Every episode is designed to deliver immediate, practical value—not inspiration that fades by Monday morning.
Immediate Clarity
Understand your fundraising blind spots and what's actually holding your organization back from consistent results.
No More Mixed Messages
Finally get your board and staff rowing in the same direction on fundraising, with less confusion and more shared accountability.
Real Steps for Monday Morning
This isn't theory—you'll leave with something you can actually do right away.
"Fundraising isn't the scary part. Avoiding it is. Lead the Ask gives you the structure to stop second-guessing yourself, lead with confidence, and turn fundraising from something you dread into something you can actually do well."— Holly Kobia, Host & Founder, Kobia Consulting
For Executive Directors
If fundraising feels like one more burden on your already full plate, Lead the Ask helps you step in with clarity, set the tone, and lead a strategy your whole team can trust.
For Development Staff
If you're tired of scrambling, guessing, or carrying the pressure alone, get the tools, systems, and language you need to build momentum and make the ask with confidence.
For Board Members
If fundraising has ever felt awkward, unclear, or like someone else's job, Lead the Ask shows you how to show up with purpose, support the mission, and be a real partner in the work.
Stop Avoiding It. Start Leading It.
It’s time to move from hesitation to confidence. Follow Lead the Ask, take the next step, and start building the mindset, language, and momentum you need to lead fundraising with clarity and conviction.
Share this with a board member before your next meeting. It gives them a clear, low-pressure way to understand their role, support the mission, and show up as a confident fundraising partner—not a bystander.