After wrapping this week’s conversation with published author and ReadySet’s CEO, Y-vonne Hutchinson, I stepped out of the studio, opened my phone, and X was ablaze. 

In the year of our Lord 2024, a startup had decided that an anti-woke marketing campaign was the best possible way for them to generate attention for their payroll software company. The culmination of this campaign was one of their sales affiliates posting a racist rant. The fallout from this was all over my timeline.  Even the most anti-woke of the tech set found themselves embarrassed and deeply uncomfortable with the direction and velocity the pendulum was swinging. 

Tech has a tortured relationship with DEI, race, and gender. The world is becoming increasingly diverse, yet the number of employees and funded startup founders from diverse backgrounds has remain unchanged, if not shrunk. Because the Me Too, George Floyd, and Black Lives Matter movements have left a bad taste in the mouths of many tech leaders, I fear we’re at risk of throwing the baby out with the bath water. 

At the heart of this uncomfortable conversation is something deeply important to company cultures specifically, and the future of tech broadly, so I invited my friend Y-vonne to talk about it. 

Y-vonne and her company ReadySet were part of the Indie v4 batch of companies. I have a deep respect for her, her work, and the company she’s building. A few takeaways from this conversation:

Historical Context of DEI Efforts
Progress in diversity, equity and inclusion (DEI) often follows a pattern of advancement followed by backlash and retrenchment. This has happened repeatedly throughout U.S. history. The recent pushback against DEI initiatives can be seen as part of this historical pattern, rather than an isolated event. DEI efforts sometimes focused too much on individual change rather than systemic issues, leading to fatigue.

DEI in the Tech Industry
The broad, nebulous nature of “DEI” as a concept allowed it to become a target for criticism. Some DEI initiatives were performative rather than substantive, causing disillusionment. The tech industry initially embraced DEI efforts, but economic pressures and changing market conditions led many companies to cut DEI programs and staff. Some tech leaders have used DEI as a “boogeyman” to justify cuts, even though the underlying issues of bias and lack of diversity remain unaddressed.

DEI as a Business Imperative
Y-Vonne argues that DEI should be seen as a tool to solve real business problems like attrition, market share, and product-market fit. Companies that ignore diversity issues risk building products that don’t serve increasingly diverse markets and user bases. Companies should aim for “healthy culture” that enables collaboration and innovation, rather than trying to mandate diversity, but the healthiest cultures are diverse.

Moving Forward
Work environments should avoid causing trauma, but shouldn’t be expected to heal past traumas - that’s not their purpose. While companies shouldn’t be responsible for “healing” employees, leaders can adopt a more trauma-informed approach to avoid causing additional harm. Broader social and political change is needed to address systemic issues, beyond what individual companies can accomplish.

The world, and its demographics, are shifting so quickly it would be a huge miss for companies not to be thinking about how their culture can reflect the broader universe or potential customers and users. 

This isn’t about quotas or raising or lowering bars, it’s about capturing opportunity. 

This was such an engaging and energizing conversation for both Y-conne and I. We hope you enjoy listening as much as we enjoyed recording it.