What the Fundraising, Ep. 288: Delusion, Disruption, and the Future of Fundraising Systems with Natalie Poindexter

Host: Mallory Erickson
Guest: Natalie Poindexter
Date: March 24, 2026

Episode Overview

In this engaging and deeply honest conversation, Mallory Erickson sits down with Natalie Poindexter—a self-described “funding systems architect,” consultant, and tech founder—to dive into what it takes to build support systems for nonprofit leaders, the realities (and delusions) of being a woman and a woman of color in tech, and why the future of fundraising needs disruption. Centering their discussion on innovation, burnout prevention, and the challenges of entrepreneurship, Mallory and Natalie trade stories about forging new paths in spaces that haven’t always welcomed them, all with actionable insights for nonprofit leaders.

Key Discussion Points & Insights

Natalie’s Unconventional Path to Systems Innovation

• Natalie’s Journey (02:42)
  Natalie recounts her non-linear road from lifeguard and EMT to teacher, public health worker, grant writer, and now tech founder. She operates as both a consultant (a “fractional development department” for nonprofits) and as the creator of Scaffina, a technology tool built “by women, for women” to support grant writers and development professionals.

  "I have also built a technology tool that is myself, in a way. Her name is Scaffina... it’s built by women, for women... I want us to reduce our burnout. I want us to regulate our nervous systems. And what better way to do that with a solution that actually supports you?"
  — Natalie Poindexter (03:17)

The Spark for Disruption: Challenging the Status Quo

• SXSW Moment (04:29)
  Natalie describes challenging a White House official at SXSW about the lack of technical assistance for organizations seeking government funding. Frustrated by the non-answer she received, Natalie decided to create the change herself, prompting her tech journey.

  "I was like, why not me?"
  — Natalie Poindexter (06:16)

Non-Tech Tech Leadership: Centering User Experience

• Building for the End User (07:22)
  Natalie highlights that as a “non-tech” founder, her focus is on functionality and user experience—not code.

  "My users aren't CTOs, so they don't care what language it’s being coded in. They care, does it save me time, does it actually work, and can I use it tomorrow?"
  — Natalie Poindexter (07:56)

• The Importance of Feelings in Product Design
  Both speakers discuss how to make tech feel supportive, warm, and genuinely helpful—especially in the nonprofit sector.

  "I want it to feel good when you're like clicking around in this product and not be like, this is a little cold and sterile... I want it to feel like, 'Oh, I’m talking to Greta. Oh, Greta is this person who supports me.'"
  — Natalie Poindexter (08:38)

The Human Element: Combining Tech and Compassion

• Human in the Loop (10:05)
  Natalie asserts the necessity of maintaining human support, even as technology scales, to ensure quality and appropriate use of AI-generated content.

  "There's still human support. So you still are connecting with a human once a month at the base... so they aren't completely separated by the voice of Greta."
  — Natalie Poindexter (10:09)

• Responsible Use of AI (10:46)
  Explicit conversations about accountability and the perils of unchecked technology are ongoing in the development of both Natalie and Mallory’s platforms.

  "Greta is only producing the content for you. You still have to deliver on whatever was written... Make sure that you've read what was written or had your grant specialist audit that content for you."
  — Natalie Poindexter (11:26)

Navigating Structural Barriers

• Being a Woman of Color in Tech (12:54)
  Natalie opens up about feeling out of place, the low odds of VC funding, and the empowerment and self-delusion necessary to keep pursuing her vision. She emphasizes building a support network.

  "I had to learn to be a little delusional of my own success and to really dig deep and find out my why... Find your people who believe in you more than anything else."
  — Natalie Poindexter (13:30)

Burnout, Grief, and the Real Cost of Hustle

• Mallory’s Cautionary Tale (17:03)
  Sharing her experience with Bell’s palsy and the effects of grief, Mallory stresses the importance of self-care and resisting the glorification of overwork, especially for trailblazers.

  "Do you remember like what happens when you don't take care of yourself? And I wish sometimes I didn't have to really bang my head against the wall to learn those lessons."
  — Mallory Erickson (18:25)

• Rejecting Hustle Culture (19:20 – 20:56)
  Natalie and Mallory agree the myth of the 80-hour workweek is unsustainable.

  "The idea that the only way you can be successful is working 16 hour days and 80 hour work weeks... you won't be successful because you'll probably be hospitalized."
  — Natalie Poindexter (15:26)

  "This sexiness in the hustle... but we don’t talk about grief... our brains don’t understand the difference between pain. The receptors are the same. So, like, we need to give ourselves some grace. We’re doing a lot of things."
  — Natalie Poindexter (20:51)

Disruption, Capitalism, and Impostor Syndrome

• Disrupting Old Models (22:48)
  Natalie reframes imposter syndrome as a sign of disruption, not deficiency, and calls for new models of leadership—especially for women.

  "Imposter syndrome is a construct... In fact, we're disruptors. We are disrupting the workplace... The motivation behind a lot of us can be we are disrupting what society is telling us you have to do to be a successful entrepreneur."
  — Natalie Poindexter (23:23)

Notable Quotes

• "I had to learn to be a little delusional of my own success and to really dig deep and find out my why."
  — Natalie Poindexter (00:56, 13:30)

• "I'm not caught up in the language. I'm caught up in: is this system, this clickable process, actually helping someone? If not, what do we need to change?"
  — Natalie Poindexter (07:47)

• "I want it to feel good when you’re clicking around in this product—not cold and sterile… I want it to feel like, 'Oh, Greta is this person who supports me.'"
  — Natalie Poindexter (08:38)

• "It’s so hard when you don't have models for the way you want to do it... We don't have models for this. We're out here trying to break the way that it's always been done."
  — Mallory Erickson (21:44)

• "Imposter syndrome… In fact, we’re disruptors. We are disrupting the workplace. We came in as women and disrupted how men did business."
  — Natalie Poindexter (23:23)

Timestamps for Key Segments

• Natalie’s introduction and background – 02:42
• SXSW challenge and the birth of Scaffina – 04:29
• Building tech for women, by women – 07:22
• Human-AI partnership; user responsibility – 10:05
• On being an outsider in tech and finding support – 12:54
• Mallory’s personal health and self-care story – 17:03
• Burnout, hustle myths, and the need for rest – 19:20
• Disrupting old models and imposter syndrome reframing – 22:48
• Closing thoughts and where to connect with Natalie – 25:26

Further Resources

• Natalie Poindexter’s platforms:
  NataliePoindexterinitiatives.com
  LinkedIn, Instagram, YouTube @NataliePoindexter

• Mallory Erickson’s coaching & programs:
  MalloryErickson.com/Podcast

Closing Thoughts

This episode is a must-listen (or read!) for anyone in nonprofit leadership, aspiring social impact tech founders, or those who find themselves navigating uncharted territory as disruptors. Mallory and Natalie offer a refreshing, honest take on the personal and professional realities of system-building, emphasizing community, realistic self-expectation, and the radical notion that we can lead differently—and thrive.