Evolution of Design Awareness and Technological Expectations Among Different Generations

In this episode of Experiencing Data, I speak with Ellen Chisa, Partner at BoldStart Ventures, about what she’s seeing in the venture capital space around AI-driven products and companies—particularly with all the new GenAI capabilities that have emerged in the last year. Ellen and I first met when we were both engaged in travel tech startups in Boston over a decade ago, so it was great to get her current perspective being on the “other side” of products and companies working as a VC.  Ellen draws on her experience in product management and design to discuss how AI could democratize software creation and streamline backend coding, design integration, and analytics. We also delve into her work at Dark and the future prospects for developer tools and SaaS platforms. Given Ellen’s background in product management, human-centered design, and now VC, I thought she would have a lot to share—and she did!

• I introduce the show and my guest, Ellen Chisa (00:00)
• Ellen discusses her transition from product and design to venture capital with BoldStart Ventures. (01:15)
• Ellen notes a shift from initial AI prototypes to more refined products, focusing on building and testing with minimal data. (03:22)
• Ellen mentions BoldStart Ventures' focus on early-stage companies providing developer and data tooling for businesses.  (07:00)
• Ellen discusses what she learned from her time at Dark and Lola about narrowing target user groups for technology products (11:54)
• Ellen's Insights into the importance of user experience is in product design and the process venture capitalists endure to make sure it meets user needs (15:50)
• Ellen gives us her take on the impact of AI on creating new opportunities for data tools and engineering solutions, (20:00)
• Ellen and I explore the future of user interfaces, and how AI tools could enhance UI/UX for end users. (25:28)
• Closing remarks and the best way to find Ellen on online (32:07)

• “It's a really interesting time in the venture market because on top of the Gen AI wave, we obviously had the macroeconomic shift. And so we've seen a lot of people are saying the companies that come out now are going to be great companies because they're a little bit more capital-constrained from the beginning, typically, and they'll grow more thoughtfully and really be thinking about how do they build an efficient business.”- Ellen Chisa (03: 22) 
  
  
• “We have this big technological shift around AI-enabled companies, and I think one of the things I’ve seen is, if you think back to a year ago, we saw a lot of early prototyping, and so there were like a couple of use cases that came up again and again.”-Ellen Chisa (3:42)
  
  
• “I don't think I've heard many pitches from founders who consider themselves data scientists first. We definitely get some from ML engineers and people who think about data architecture, for sure..”- Ellen Chisa (05:06)  

• “I still prefer GUI interfaces to voice or text usually, but I think that might be an uncanny valley sort of thing where if you think of people who didn’t have technology growing up, they’re more comfortable with the more human interaction, and then you get, like, a chunk of people who are digital natives who prefer it.”- Ellen Chisa (24:51)

• [Citing some excellent Boston-area restaurants!] “The Arc browser just shipped a bunch of new functionality, where instead of opening a bunch of tabs, you can say, “Open the recipe pages for Oleana and Sarma,” and it just opens both of them, and so it’s like multiple search queries at once.” - Ellen Chisa (27:22)

• “The AI wave of  technology biases towards people who already have products [in the market] and have existing datasets, and so I think everyone [at tech companies] is getting this big, top-down mandate from their executive team, like, ‘Oh, hey, you have to do something with AI now.’”- Ellen Chisa (28:37)
  
  
• “I think it’s hard to really grasp what an LLM is until you do a fair amount of experimentation on your own. The experience of asking ChatGPT a simple search question compared to the experience of trying to train it to do something specific for you are quite different experiences. Even beyond that, there’s a tool called superwhisper that I like that you can take audio content and end up with transcripts, but you can give it prompts to change your transcripts as you’re going. So, you can record something, and it will give you a different output if you say you’re recording an email compared to [if] you’re recording a journal entry compared to [if] you’re recording the transcript for a podcast.”- Ellen Chisa (30:11)

• Boldstart ventures: https://boldstart.vc/
• LinkedIn: https://www.linkedin.com/in/ellenchisa/
• Personal website: https://ellenchisa.com
• Email: ellen@boldstart.vc