Meet Anna: How the Dot Com Boom Shaped Her AI Investing Strategy—And Which Founders Get Her Attention

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Anna Barber spent the first months of her life living in the Chelsea Hotel across the hall from Janis Joplin—possibly an early sign of the bold, fearless path she would take. From contemplating a life as a backcountry guide to founding a book publishing startup, Anna’s eclectic interests laid the groundwork for her eclectic career. 

Anna’s initial foray into the corporate world as a lawyer and McKinsey consultant provided a solid foundation in understanding the inner workings of large companies. Transitioning to Hollywood, she spent six years as a talent manager, refining her storytelling prowess—a skill that she now leverages to help founders articulate their visions compellingly. And as a former founder herself, Anna has navigated entrepreneurship firsthand, so she understands the resilience and creativity required to succeed in the startup world.

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As a venture investor, Anna champions a philosophy that combines deep support with high expectations, believing that this duality drives the best outcomes. She also sees beyond the frothy valuations and bubble talk, understanding that even in that environment generational companies will emerge. In an industry often dominated by short-term gains, her long-term vision and holistic approach to venture capital stand out.

We sat down with Anna to learn more about her career journey, what kind of founders she wants to work with, and what innovations she’s interested in right now.

Anna's recent publications 

• AI Fundamentals: What AI Really Does and Where We’re Looking to Invest
• M13's Guide to Building Your Early-Stage Fundraising Deck
• AI Guardrails: How Enterprises Can Safely Adapt to the Generative AI Wave
• The Rise of AI Agents

Q&A with venture investor Anna Barber

Many believe AI is at peak hype right now. Does a founder have to have AI in their pitch deck to get your attention? 

AI is all about efficiency gains—it makes things faster, cheaper, and better. It’s not a trend, it’s a paradigm shift that is improving efficiency. So if you’re a founder that is not using AI. I want to know why.

What are people getting wrong about AI right now?

There's a notion right now of we're in an AI bubble, and then the conclusion that some people draw is nothing that's getting funded today is going to work out. I think that's the wrong frame. 

People see that we're undergoing a massive platform shift—similar to what happened in 1999, similar to what happened in 2008 with cloud computing—and so people are excited to invest behind that thesis. As a result, valuations have maybe gotten a bit frothy, and people are getting ahead of their skis in terms of backing things that might not have an actual market.

“The fact is there will be generational companies that are getting funded now, even though there will also be a lot of companies that don't succeed.”

I think both can be true. While we're in a bubble and undergoing a major, exciting platform shift, it's also a great time to be investing. When you look backwards at 1999, you see evidence of that in companies that not only survived that period, but thrived, and become some of the largest companies in the world (like Google and Amazon, and infrastructure companies like Cisco). 

What is exciting to you about AI right now?  

I’d say there are three big areas I’m really interested in:

I’m also interested in companies building AI agents. I believe that yesterday, AI was all about data structures, algorithms, and machine learning. Today, the focus is on generative AI. And the AI of tomorrow is the world of agents.

What is not interesting to you about AI right now? 

As an early-stage investor, it’s challenging to invest in large foundational models. This is where big tech companies are focused on investing.

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As an investor, what makes a founder stand out to you? 

There are a few types of founders that stand out to me. 

• Founders with a lot of courage, who aren’t afraid of contrarian thinking 
• Founders who see venture capital as a tool, not the end goal
• Founders with deep perspective on the market they’re building in because of prior experience—it’s probably not a coincidence that I tend to be drawn to older founders
• Founders with a deep conviction about their purpose and the business they’re trying to build

You were a founder and worked at a startup that went bust in the 2000 dot com boom. How has that shaped the way you make decisions as a venture capitalist?

I learned from the early 2000s dot com boom, that in every hype cycle, there will still be generational companies made. Apple, Amazon and Google were considered startups that many called “hype” back in 2001. I look at startups today as the future Googles and Apples. Regardless of the hype, a handful of startups today will be the biggest companies in the world in 2035.

‍You’ve also been a lawyer, a consultant, a talent manager, and more—how have these other career paths shaped you as an investor?

Starting my career as a corporate lawyer and a McKinsey strategy consultant gave me a real foundation of understanding how large companies work. That experience was valuable to me as I transitioned into the startup world, because I didn't harbor any illusions that things were somehow easier if you were a large company.  

I also spent six years as a talent manager working with writers and directors, which really helped me hone my storytelling skills. The time I spent in Hollywood has really informed both my ability to craft a great story and my appreciation for storytelling as a leadership skill. I believe founders are only as good as the story they tell. What attracts capital? What attracts people to work for you? Stories. 

Finally, I founded a company called Scribble Press: I raised money, ran that company for a while, and sold it. So I went through that entire trajectory of inventing something completely new, bringing it to the world, pivoting it, trying to sort out how to make the unit economics work, trying to iterate quickly in a physical retail environment where quick iterations are really, really hard. That experience taught me a lot of humility and insight into how tough it is to be a CEO and how lonely it can be.

What’s a daily habit of yours? 

Every morning I write down five things I’m grateful for and text them to a friend. It’s my gratitude practice. And I say “practice” because it doesn’t always come naturally—but I’ve found that when I do it, it puts me in a more positive mindset and helps me be more creative throughout the day. 

To close out, let’s do a quick lightning round: 

First job?

Photographer’s assistant. Once during a cosmetics catalog shoot, it was my job to make the perfect swirl in the cold cream. Today that job doesn’t really exist anymore; you can create the swirl with AI. 

Favorite app?

The New York Times games app.

Guilty pleasure? 

Elin Hilderbrand novels—they always feel like the beginning of summer to me. 

Book, movie, or music rec?

Right now I’m reading This Is How You Lose the Time War. It’s fantastic. 

Hidden talent? 

I used to be a pretty serious triathlete, and I can change over from the swim to the bike in record time. The secret is laying out your outfit in exactly the right way, for maximum efficiency. 

If you weren’t working in tech or venture, what would you be doing?

I think my alter ego lives in the Adirondacks and teaches kids to rock climb.