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Navigating the Pitfalls of Generative AI’s Post-Hype Era w/ Charlie O’Donnell

By February 22, 2024March 13th, 2024No Comments

Investors got over their skis in 2023 so 2024 will see low returns, high risks and even higher competition.

Hey, I’m Lindsay, the host of Make Sense w/ Lindsay T., Lady Engineer®, a weekly podcast where my guests and I simplify complex topics at the intersection of people & technology. We analyze whatever hot mess is in the news, evaluate trending innovations through a human-first lens, and take deep dives on a need-to-know basis.

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Folks, we’re entering what Gartner calls “The Trough of Disillusionment” with  Generative AI companies.

An xy graph where X is Time and Y is Visibility

“We got over our skis collectively and now I think folks are feeling that,” Charlie O’Donnell said on this week’s episode of Make Sense. Do you agree?

Going into the second year of this podcast, I will continue to emphasize that the media hype cycle creates fear: Fear of missing out or fear of negative future impacts.

Eventually, the reality of the user adoption curve sets in. So AI taking your jobs probably won’t happen tomorrow but you can future-proof yourself by learning about the tools.

With Charlie, I also cover:

➡️ The need for growth funding to step up for climate companies
➡️ How to make room for right-brain thinking in startups and innovation
➡️ Substack’s pseudo-libertarian, free-speech response to their Nazi problem

Choice Quote

Once you acknowledge failure, you bust your butt to ensure that you do everything to avoid it. Your don’t want to fail so you do the work necessary to see if you can prevent it. At some point you have to cut your losses and I think that’s healthy.

– Charlie O’Donnell, Investor Coach & Founder of Brooklyn Bridge Ventures

Picture of Lindsay Tabas and picture of Charlie O'Donnell with the title of the episode for Make Sense

Buck the media hype cycle. Calm the fear-mongering. Laugh at the inanity of Tech CEO “hero culture.” Be the smartest person in your peer’s LinkedIn feed:

Key Takeaways with Charlie O’Donnell

Here are Charlie’s takes on the predictions I pitched him in the segment Crystal Ball: What does the future hold?

  1. Twitter Will Become the Next “Everything App” that is video-first & enables intimate community-based conversations and panels. No
  2. Many Generative AI Companies Will Die: Yes
  3. VCs will turn inward to build for the future: No
  4. Growth Funding Will Remain Scarce for Climate Companies: Yes, particularly for seed stage.

Listen now on Apple, Spotify & YouTube

Show Notes

00:00 Introductions
01:25 Crystal Ball: Predictions for The Future
05:13 AI investment Opportunities
08:36 VCs Investing in Internal Operations
13:45 Scarcity of Growth Funding For Climate Companies
22:13 Bringing Vulnerability into Entrepreneurship
31:48 Is Slowing Down Imperative For Critical Thinking
37:56 The Openness of the New York Ecosystem
44:41 To Stay or To Go – The State of Substack
53:00 Where to find Charlie

Where to find Charlie O’Donnell

Charlie O’Donnell, founder and general partner of Brooklyn Bridge Ventures. He also publishes a weekly newsletter called Next NYC and his thoughtful writings on his blog We discuss the startup ecosystem and the differences between NY and Silicon Valley cultures, the state of funding, understanding risk-taking, and the importance of failures and vulnerability in entrepreneurship.

Note: Charlie is not making new investments right now and is an investor coach for venture professionals.

Events & Education in NYC:
Personal / Professional Blog: This is going to be BIG

Where to find Lindsay Tabas


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