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Oleg Karakash – Experienced founder with $8M exit

I'm Oleg Karakash, founder of Stamina AI and ExoChat. I help turn ambiguous ideas into structured, validated digital products. My biggest achievement (till now) selling one of my startups to Snapchat for 8 000 000 $
Oleg Karakash

CEO / CPO / Startup founder / Venture Partner, Stamina AI / ExoChat / Gradient / Teleport

Why did you decide to become a mentor?

I’ve spent the last few years building startups from scratch — often in messy, fast-paced environments where clarity and confidence are hard to come by. In that process, I realized how much faster you can move when someone helps you name what matters, what doesn’t, and what’s truly possible. Mentorship felt like the natural continuation of that — sharing not only what worked for me, but also what I wish someone had told me earlier. I also see mentorship as a two-way exchange. When I speak with early-stage founders or career switchers, it sharpens my thinking, exposes me to new questions, and helps me stay grounded. You don’t have to be perfect to be helpful — you just have to be honest, clear, and open. That’s what I try to bring into every session.

How did you get your career start?

I started out by building side projects — not because I had a perfect plan, but because I was curious and slightly obsessed with how ideas turn into products. My first real break came when I joined a startup as a product and business lead, where I had to grow fast, wear 10 hats, and learn to ship even when things weren’t perfect. Along the way, I had a few informal mentors — people who asked me the right questions at the right time. One of them taught me to think in terms of systems, not just features. Another pushed me to articulate not just what I was doing, but why it mattered. That mindset shift helped me build products people want, not just what I could code or design.

What do mentees usually come to you for?

Most people I work with are trying to build or validate something — a startup idea, a product, a personal brand. They usually feel stuck somewhere between “I have a vision” and “I don’t know how to make it real.” I help them break the fog. In our mentorship, we usually start with structure: clarifying the problem, defining a clear hypothesis, mapping out quick validation steps. Then we work through practical moves: messaging, positioning, landing pages, outreach, AI tools, anything that gets results faster. I’m especially helpful to people working in the AI / no-code / digital product space, or those transitioning into entrepreneurship from corporate backgrounds.

What's been your favourite mentorship success story so far?

One mentee came to me with a vague idea for a writing tool. He was a developer, but wasn’t sure how to position the idea or get any traction. In two months, we worked through his value proposition, created a one-page landing, launched a basic prototype with GPT, and got him 100+ signups from cold outreach. But what made it my favorite wasn’t just the progress — it was seeing him shift from “maybe I’m not cut out for this” to confidently sharing his product in public. That mindset shift — from hiding to shipping — is the real unlock.

What are you getting out of being a mentor?

Mentoring has become a way for me to reflect, refine, and recharge. It sharpens my ability to communicate clearly, zoom out from my own projects, and spot patterns in other people’s journeys — patterns I often miss in my own. It’s also a way of giving back to the ecosystem that helped me grow. I didn’t get where I am by myself. I had people who took the time to listen, challenge, and support me — sometimes for no reason other than kindness. Mentoring is how I pay it forward. And selfishly? It’s energizing. Seeing someone break through a block or launch their first product reminds me why I do what I do.

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