It Doesn't Hurt to Ask!

It Doesn't Hurt to Ask!

Whether you're a professional fundraiser, volunteer on the board of a non-profit organization or you're about to make your first charitable donation, we've got a podcast for you! It Doesn't Hurt to Ask! explores the world of philanthropy through a critical lens. While that might sound serious, we have a lot of fun along the way. In our first season, we're chatting with "Shift Disturbers," charitable sector leaders who are doing things differently. After listening, you won't think about our sector in the same way for our motto is: in fundraising, as in life, it doesn't hurt to ask! We hope you listen, learn and laugh along with us as we chat all things fundraising and philanthropy. Great news! It Doesn't Hurt to Ask! is in the Top 25 Fundraising Podcasts to listen to on Feedspot.

Episodes

January 8, 2026 21 mins

.css-1t8gq41{border:none;background-image:none;background-color:transparent;box-shadow:none;color:#2F3133;cursor:pointer;font-size:inherit;padding:0;-webkit-text-decoration:inherit;text-decoration:inherit;width:-webkit-max-content;width:-moz-max-content;width:max-content;}.css-1t8gq41:hover,.css-1t8gq41:focus{-webkit-text-decoration:inherit;text-decoration:inherit;}

Mark as Played

Read more

Mark as Played

Read more

Mark as Played

We've all heard the phrase "culture of philanthropy." But what does it really mean? And how do you build one when you're already knee-deep in grant deadlines, donor meetings, and database cleanup?

In this episode, we unpack the elusive culture of philanthropy through a systems change lens – and explain why strong fundraising success isn't just about strategy. It's about shifting the way your entire organization thinks, acts, and wo...

Mark as Played

Your annual report shouldn't just check a box – it's a powerful donor stewardship opportunity to celebrate impact, engage supporters, and make them feel proud to be part of your mission.  
In this episode from the Fundraising Lab archives, we're joined by Brooke Erickson as we provide expert guidance on creating a donor impact report. Whether you're launching your first report back to donors or rethinking your annual report strateg...

Mark as Played

It Doesn't Hurt to Ask is the podcast for nonprofit leaders and fundraisers who want to raise more money with less chaos and build systems that last.

Hosted by Cathy Mann, award-winning fundraiser, educator, and founder of The Fundraising Lab, each episode blends decades of sector experience with practical insights you can apply right away.

Whether you're leading a team, writing your first grant, or steering a $2M campaign, you'll ...

Mark as Played

So, you've got a vision to grow your fundraising program, but you're not sure how to get there.  

Whether you're volunteer-led, an executive director flying solo, or building your first fundraising team, the path to sustainable fundraising growth isn't always clear.

In this episode, we break down the real stages of fundraising growth and what is required at each stage – not just in terms of fundraising strategy, but in terms of sys...

Mark as Played

That first major donor meeting can feel intimidating – but with the right preparation and strategy in place, it's an opportunity to build a meaningful philanthropic relationship that could transform your organization's impact.

In this episode from the Fundraising Lab archives, we're joined by Deb Thompson as we provide expert fundraising coaching on how to prepare for an upcoming major gifts meeting with a prospective foundation fu...

Mark as Played

Tune in as Cathy interviews Paul Taylor, Executive Director of FoodShare Toronto. Paul is a lifelong anti-poverty activist who has used his experience to fuel a career focused on helping others and dismantling the beliefs and systems that lead to poverty and insecurity.

Mark as Played

This is a replay of one of our favourite episodes from last season. In this episode,  Simone Joyaux, ACFRE (proclaimed by Cathy as the Grand Dame of Social Change Philanthropy) reviews the do's, don'ts and dilemmas of fundraising for social change. From the professionalism of fundraising to board governance, this wide-ranging conversation will su...

Mark as Played
This is a replay of one of our favourite conversations from last season. On today's episode, Cathy sits down with Ajeev Bhatia, Manager of Policy and Community Connections at the Centre for Connected Communities. Ajeev discusses how the situations of his past have transformed into motivation for his future as he charts a new course for philanthropy and invites us to get Comfortable with Being Uncomfortable.

Mark as Played
This episode is a replay of one of our favourite conversations from last season of It Doesn't Hurt to Ask. Dr. Elizabeth Dale is a fundraiser turned academic who studies the giving habits of women and LGBTQ donors as an Assistant Professor at Seattle University's Nonprofit Leadership Management program. Elizabeth's insights are invaluable on both a practical level and in a big-picture way and she's got the research to back it all u...
Mark as Played

On today's episode, Cathy sits down with Paulina O'Kieffe-Anthony, the executive director of SKETCH based in Toronto. Paulina discusses her new role as Executive Director of SKETCH and some of what she's learned in various roles. She also talks about her work in the arts with racialized and marginalized youth. She then talks through how having a strong fundraising plan and database has been a game-changer for SKETCH. And finally, t...

Mark as Played

In this episode of 'It Doesn't Hurt to Ask,' the Fundraising Lab's Anne LeMesurier talks with David Phu from Nonprofit Video Comms. We learn about how small to mid-sized nonprofits can look to simplify their marketing communications while increasing impact using simple and targeted video. David and Anne discuss different types of audiences, where you should spend your time and money, strategies for success and what data you should ...

Mark as Played
February 1, 2022 22 mins

On today's episode, Cathy sits down with Sharon Redsky, the Principal at Redsky Fundraising. Sharon discusses how community has the ability to be transformed through intentionality and deepening relationships with partners.  She discusses finding common ground, investing in women and the ongoing resiliency of the indigenous community. Join our Spark Community for FREE: https://www.fundraisinglab.ca/spark

Mark as Played
On today's episode, Cathy sits down with Ajeev Bhatia, Manager of Policy and Community Connections at the Centre for Connected Communities. Ajeev discusses how the situations of his past have transformed into motivation for his future as he charts a new course for philanthropy and invites us to get Comfortable with Being Uncomfortable. Get more great podcasts at www.fundraisinglab.ca/resources 

Great news! It Doesn't Hurt to Ask...
Mark as Played
October 3, 2019 42 mins

Ken is the President and CEO, William Osler Health System Foundation and has just been named the 2019 Outstanding Fundraising Professional by the Association of Fundraising Professionals Greater Toronto Chapter. Ken is a quiet shift disturber in our sector this conversation reflects the things he has done to shift and serve the sector. Shout outs to Dr. Krishan Metha, Emma Lewzey, Marni Spears, Kulvir Singh Gill, Rickesh Lakhani.

Mark as Played
September 26, 2019 40 mins

Join Cathy and Laura Manning, Executive Director of the Lyle S. Hallman Foundation as they discuss the foundation's shift from program-based funding to providing General Operating Support (read: unrestricted funding!) to some of their grantees. The Lyle S. Hallman Foundation is a real shift disturber with a board that gets excited about doing things differently. Tune in to hear about their approach to values-based philanthropy.

Mark as Played

It Doesn't Hurt to Ask! podcast is back after a little hiatus. In this episode, Cathy sits down with Chris Baylis of The Sponsorship Collective to discuss the "secretive" world of cause sponsorship. Chris is a self-confessed sponsorship geek. After several years as a "sponsor," Chris decided to cross over to the sponsorship sales side where he has personally closed tens of millions of dollars in sponsorship deals. Chris has been on...

Mark as Played
May 16, 2019 2 mins
I remember my early years of fundraising. The questions, the insecurity, the doubt. I'm so glad to be past that stage of self-questioning. I see so many early in their careers with similar feelings. When I reflect back on that time, I wish I had had someone I could reach out to when I had questions, rather than wring my...
Mark as Played

Popular Podcasts

    I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

    Stuff You Should Know

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    The Joe Rogan Experience

    The official podcast of comedian Joe Rogan.

    The Breakfast Club

    The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

    SmartLess

    "SmartLess" with Jason Bateman, Sean Hayes, & Will Arnett is a podcast that connects and unites people from all walks of life to learn about shared experiences through thoughtful dialogue and organic hilarity. A nice surprise: in each episode of SmartLess, one of the hosts reveals his mystery guest to the other two. What ensues is a genuinely improvised and authentic conversation filled with laughter and newfound knowledge to feed the SmartLess mind. Subscribe to SiriusXM Podcasts+ to listen to new episodes of SmartLess ad-free and a whole week early. Start a free trial now on Apple Podcasts or by visiting siriusxm.com/podcastsplus.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.