From pioneering proprietary ad systems in the early days of the internet to steering cutting-edge AI innovations in advertising, Michael Yavonditte has consistently been ahead of the curve. As the founder and CEO of Yieldmo, and a seasoned private investor with over 100 portfolio companies, he brings decades of experience navigating the intersection of technology, creativity, and business strategy. With 37 patents to his name and a track record of competing against some of the industry’s most formidable players, he’s not only witnessed the evolution of advertising technology, he’s helped shape it. In this conversation, we explore his journey, the role of AI in redefining advertising, and the bold thinking that fuels his vision for the future.
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You’re CEO and a private investor in the technology industry, and currently the founder and CEO of Yieldmo, an ad tech company. Before we go deeper into that, I’d like to talk about the beginning of your journey. Could you share why you became interested in advertising technology?
I started working on proprietary ad systems in the mid-90s, which dates back to the beginning of the internet. I’ve been working in the field consistently throughout my career, on profile targeting systems, search advertising systems, contextual systems, machine-learning-based systems, and now AI-based systems. I’ve been deeply involved in all the major trends in advertising since the beginning.
When did you realize AI would play a significant role in your vision?
Probably right after ChatGPT launched. It became clear that things were going to change significantly. Generative AI was a different flavor of AI and machine learning than I had seen before, but I quickly understood how it could be used. We moved aggressively into AI early on and have been using it, and finding new ways to use it, for over two years now.
Before Yieldmo, you built Quigo. How did that experience influence how you’re building now?
Quigo was one of the first successful builders of contextual targeting in advertising, and one of the few companies to successfully compete against Google. I learned a lot about building high-performing systems and competing against some of the most aggressive competitors in business history. At Quigo, I built multiple versions of our core technology. At Yieldmo, we’re doing the same, building multiple versions of our AI-driven core technology.
You’ve often emphasized that AI should enhance, not replace, humans. Can you explain your thinking?
We’re building what’s called “man-in-the-middle” systems. Our technologies can do a lot automatically, but in most cases, humans make decisions in tandem with the technology. I don’t think the market is ready for fully automatic, end-to-end advertising systems. When it is, we’ll be ready, but for now, we focus on giving humans decision points along the way.
Many people believe advertising will be one of the next industries to automate. With AI agents now a hot topic, what’s your perspective?
We’re already using agents in various parts of our system to complete tasks, and we’ll continue to do so. For creative work, GenAI can help, but many decisions still need to be made by brands. We try to balance machine optimization with human judgment. Machines are great when the volume of decisions or information is too high for humans to handle such as in optimization algorithms, but for creative messaging, most brands still want final approval.
Your systems are grounded in radical transparency. What does that mean to you?
There’s a lot of talk about transparency and control in the industry. Many big brands want to know exactly where their ads are running—usually they find out only after a campaign ends. We show advertisers where their ads will run before they spend a dollar. This is a radical change. They can refine targeting and make adjustments in real-time based on granular tools and data. It’s challenging to surface millions of possible ad placements in a way that’s usable, but that’s the goal.
You hold 37 patents. How has that shaped your problem-solving approach in AI advertising?
Patents don’t solve problems directly. We start with creative, novel ideas, decide whether they’ll make it into the product, and then determine if they’re patentable. Having 37 patents puts us in rare company, it signals that we’re one of the most inventive and creative firms in advertising.
What’s the biggest challenge in getting patents?
Finding a great patent attorney. Many believe nothing can be patented. Ours is optimistic, which helps. But ultimately, you need a unique, creative idea, without that, you won’t get a patent.
You’ve invested in over 100 companies. What drives your investment decisions?
It’s usually both the idea and the people. The idea must be good, and I have to believe in the team. I haven’t noticed a single pattern, but I’ve had consistent success in areas like analytics.
Advertising AI walks a fine line between personalization and privacy. How do you design systems that respect user intent while delivering engagement?
We’ve never focused heavily on user identity, even before AI. Many companies invest heavily in identifying users, we don’t. Instead, we focus on statistical models, such as historical performance of certain pages, without knowing who the user is. None of our AI work relies on individual user data.
How do ethics, fairness, and accountability factor into Yieldmo’s AI work?
I don’t spend much time worrying about AI ethics because our work is far from areas where AI can be dangerous. We know AI isn’t 100% accurate, so we build processes and systems to detect and correct inaccuracies.
Looking ahead, how do you think AI will shape the brand–consumer relationship?
Edgier brands will take bigger risks. Conservative brands will change slowly. It’ll take time before AI truly reshapes brand–consumer relationships, but eventually even conservative brands will use AI to generate creative content, including TV commercials. I think advertising will change radically in the next 5–10 years.
Have you had mentors who influenced your leadership style?
Yes, former and current investors, board members, and my father, who’s a computer scientist and engineer. I come from a family of engineers, and I value input from many people.
Is there a human story you’d like to see emerge from AI in the next 5–10 years?
There’s so much potential. Outside advertising, I’m excited about education. I’m helping my son prepare for the SATs using AI to build diagnostic tests. That’s just one small example. In advertising, I think every aspect will eventually be transformed by AI.
How have communities, teams, and investors shaped your AI platforms?
We’ve had ongoing debate about how to use AI. At first, it was a bumpy road, but over time, we aligned on big, innovative ideas, some very different from our core business. The products we’ll launch in the next six months will make us look like a very different company.
Finally, what advice would you give to entrepreneurs entering AI advertising?
Don’t be overly cautious. Many people use AI in small, incremental ways for modest gains. We’ve chosen to build products radically different from our core business because the AI wave is too important for small steps. Have the courage to try big things.
