Board vs Staff: Strategy and the Flywheel

Loren and Dawn discuss how the elected board sets strategy and staff drives tactics through a collaborative flywheel.

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Episode notes

Guests

Dawn Wages | Loren Crary

Panelist

Richard Littauer

Show Notes

In this episode of Sustain, Richard Littauer talks with Dawn Wages, former Chair of the Python Software Foundation board and Loren Crary, Deputy Executive Director of the PSF, about how the PSF sustains Python and its community, governance, fundraising, and events like PyCon US, and why they ultimately turned down a $1.5M NSF grant rather than accept new anti-DEI conditions. They walk through what the grant was for, how the decision unfolded, the financial and ethical risks involved, and the overwhelming community response in donations and support, ending with a call to participate in the PSF fundraiser and submit talks to PyCon US 2026. Press download now to hear more!

[00:02:41] Dawn explains she just finished her term as Chair at the PSF Board, previously served as Treasurer, and that board seats are elected volunteer toles with three-year terms.

[00:03:40] Loren describes her job as Deputy Executive Director, #2 to ED Deb Nicholson. She leads fundraising and revenue strategy, handles internal operations and strategic planning, and she clarifies that the Python Steering Council steers the language itself and mentions PyCon US will be in Long Beach, CA May 2026.

[00:05:38] Dawn shares a personal story how PSF funding and local Python user group helped her start in Python a decade ago and encourages listeners to donate and use company matching.

[00:06:57] Loren speaks about sponsors and individual donors and plugs the fundraiser and the “cute snake thermometer” on the donate page.

[00:08:00] Richard, as a board member of Python New Zealand, underscores PSF’s support for Python user groups and conferences. He then pivots to ask about strategy where Loren describes how the board leads strategy.

[00:13:34] Dawn reflects on learning to chair the board for the first time, praising staff expertise, and she describes the ‘flywheel’ model where staff and board collaborate closely, with staff often joining board meetings to co-develop strategy.

[00:15:18] Loren highlights the PSF board and representation.

[00:16:59] Richard gives a special shout-out to Phyllis Dobbs as one of the “unsung heroes” of open source, noting her work with OSI and Deb in the past.

[00:17:26] The convo turns to the NSF Safe OSE program and what happened with the large grant the PSF was awarded and then declined. Loren details everything that happened and gives a shout-out to Seth Larson, whom she collaborated with.

[00:29:00] Loren reads the key clause that PSF would need to affirm, and the board ultimately made the call that it was too risky to their mission to accept the terms.

[00:31:42] Dawn explains the board’s decision to withdraw and Loren notes that no one on the board or staff ever floated “dropping DEI to take the money.”

[00:33:55] Dawn points to Python’s reputation as a welcoming, diverse community and DEI is portrayed as “lifeblood,” not an optional extra.

[00:35:03] What happened after they said they weren’t taking the money? Dawn and Loren recount an outpouring of support after the public statement, and we find out how much money the fundraiser has made so far along including an anonymous donation.

[00:38:33] Dawn zooms out to decades of conversations about funding open source, arguing that individual donors and major AI companies profiting from Python should be contributing at scale.

[00:41:20] Richard reinforces the ongoing donation, and Loren plugs the PyCon US Call for Proposals (open through December 19) with new AI and security tracks and invites listeners to submit.

Quotes

[00:07:09] “If you want to know what a nonprofit does, look at who their funders are and that’s who they’re working for.”

[00:12:07] “The board sets a strategy, but there needs to be a ‘flywheel’ from the staff to keep things like that going.”

[00:18:45] “We dipped our toes into grant funding, and we thought that would be a great way to make our work more sustainable.”

[00:32:40] “The $1.5 million is not net worth putting the future health and safety of the language in the organization in jeopardy.”

[00:32:58] “I am proud that at no point did anyone float: What if we just stopped doing everything DEI and take the money?”

[00:38:09] “I like my boss to be the users.”

[00:38:41] “We’ve been talking about what it means to fund open source for decades…I think this is an interesting arc that we’re experiencing. I’m hoping that the numbers will have two or three commas from individual donations.”