Olivya Post-Mortem 🤖: Confessions of A Short-lived AI CEO
Why AI still can't replace the human touch, and will not so soon
How is it going with Olivya?
That’s the question many industry peers have been asking me lately. While answering it, I couldn’t help but feel a sense of disappointment—with myself more than anything. But I knew I had to be honest about where I stood in my entrepreneurial journey and where I truly wanted to invest my energy.
And that energy wasn’t in building a scalable AI/tech company.
We built Olivya in just three months and three months of research and testing. Here’s a snapshot of what we created during this process:
Alongside my partner, Marko Kecman, we’re happy to share our key insights—both about the product and the market—for anyone who might want to continue the quest of building the perfect AI human companion…
#1 The AI App Challenge: Another Habit-App Challenge
In the rapidly growing world of AI apps—whether AI therapists, coaches, mentors, or language tutors—the competitive advantage doesn’t lie in the large language model (LLM), already owned by the AI and Tech giants, but in the use case. The future opportunity for success is in creating a product that’s perfectly tailored and convenient for the intended audience.
“Olivya is your coach in the pocket, a conversational AI coach that empathizes and helps you break down your needs and goals.”
We originally aimed to build the best AI coach by embedding our coaching methods and principles into the app. However, the real challenge wasn’t in the AI itself but in fostering the habit of actually using Olivya. So our vision rapidly shifted from building an AI coach to building habits, discipline, and accountability into an AI coach.
While users loved their first session with Olivya (15–30 minutes of engagement), they often didn’t return—even with reminders via email and calendar notifications.
For instance, here’s a screenshot of my own poor track record that week:
Despite having all the tools in place to nudge users back, the real obstacle was self-discipline—a challenge every new app faces.
With so many apps competing for attention in our daily lives, the question isn’t just about retention. It’s about integration: How does this app become an indispensable part of a user’s lifestyle?
One surprising insight from our beta test was that users didn’t feel guilty about skipping a session with Olivya. Why?
“Olivya is just an AI.”
When users had calendar appointments with Olivya, they often skipped them if something more important came up.
Would they do the same with a human coach? Probably not.
With a human coach, there’s accountability, trust, and even guilt—powerful motivators that ensure people show up because they’ve made a commitment to both the coach and themselves.
So, if you are building an AI app, be aware that the main challenge will be building the habit of using your app. That is why mobile games are so powerful as they have strong core loops and mechanics that create habits that transcend the habit of self-discipline.
#2 B2B or B2C? Deciding Your Path
If you’re building a consumer product, one of the key market decisions you need to make is whether you’re targeting businesses (B2B) or consumers (B2C). These are two entirely different games, each with its own challenges.
B2B: If you’re focusing on B2B, your primary challenge will be sales. You’ll need a dedicated sales team to handle outreach, set up calls, and navigate multiple layers of decision-makers (e.g., Heads of People, COOs, or CEOs). It’s a complex and often lengthy process that requires solid CRM systems and skilled personnel.
B2C: On the other hand, B2C is a user acquisition and retention game. Success depends on building a community, leveraging content strategies, and navigating the ever-increasing costs of paid user acquisition. Organic growth through SEO and content creation is crucial, and maintaining an engaged user base is another grind entirely.
Based on our learnings, it is not recommended to chase both markets at the same time in the early phase, as this is already hard enough to execute well in one direction. Pick one market and focus on it.
Marko and I leaned toward B2C because of our background in games. However, the market often has its own response. If you notice stronger demand in B2B while you’re focused on B2C (or vice versa), my advice is to remain open to pivoting based on where your first clients naturally emerge.
#3 Welcome To The AI Race
The current landscape of AI apps feels like a gold rush, quite similar to the gold rush I have witnessed in games over the past decade, but on steroids.
Over the past six months, I’ve seen apps rise and fall quickly. It’s a “winner-takes-all” scenario, where the apps that succeed are those that penetrate the market fast, secure adoption, and execute flawlessly.
I’ve tested a variety of AI coach & therapists apps over the past months: Canopy, Bunch (acquired), Wave.ai (acquired), Finch, Clare&me, Ahead, OneLeaf, or Manifest. Time will tell which ones will prevail.
A similar trend is playing out with AI notetaker apps, where competition is fierce. For instance, Fireflies struggled to keep up with quality transcription, paving the way for newer players like Circle Back and Fathom (I am now using Fathom). And the question remains: How long will they stay on top?
There’s plenty of potential in gamifying AI coaching or health apps—a concept we explored with our team.
However, we had to ask ourselves: Did we want to create a gamified coaching app?
And more importantly: did we have the stamina to compete in this relentless AI race after a decade of already grinding in the gaming industry?
For us two, the answer was no. And so we decided to park Olivya after the summer, despite investors and VCs being excited to see this product grow.
#4 The Future of AI Will Not Be Human (Yet)
One of our original motivations with Olivya was to serve humanity with impact and offer coaching solutions at scale—making it affordable and accessible to those who couldn’t afford human coaching or fit it into their schedules.
We ran a beta test with 250+ users and got valuable feedback. While Olivya excelled at unblocking users in a single session, deeper insights emerged:
“Olivya is not human, and she doesn’t provide the human touch I’m looking for.”
Users wanted more than just guidance; they craved genuine connection.
This was a turning point for me. As someone passionate about bridging human gaps, I began questioning whether Olivya truly aligned with what people needed most.
I’ve spent 16 years in the gaming industry, and while I’ve loved it, I’ve also seen how apps, games, and technology have pulled us further away from what we deeply crave: human connection.
The most meaningful relationships I’ve built as a leader and coach have been through face-to-face, in-depth interactions—something no AI can replicate (yet?).
Choosing Human Connection
As an entrepreneur and human advocate, I’ve personally decided not to continue building Olivya as a tech company—for now.
Instead, I’m focusing on my roots and passions: fostering deep, transformative human connections. Since making this decision in September, my leadership coaching business has flourished. Clients are flowing in, and my new service of retreats is creating a movement for much-needed human connection in an increasingly isolating tech-driven world.
I’m not giving up on Olivya entirely. When the time is right, I will reconnect with her, with more clarity and purpose.
But for now, I have enough work to do fostering deep human connection :)
If you are interested in learning more about Olivya, feel free to reach out to me.
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Thank you for sharing the post-mortem of Olivya.
It's insightful to read the ups and downs of your entrepreneurial journey building it, the before and after.
It's though out there and it's inspiring learning more about your experience