Ask Me Anything · 60 min with

Oleg

Open 60 minutes. Bring any question on AI rollouts, fundraising, GTM, or founder strategy. I prep a short doc with specifics before the call so we use the hour for actual problem-solving, not context. Read more ↓
Oleg Karakash
$199
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4.9
/
🇺🇸
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60 minutes

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About this Session

Open 60 minutes. Bring any question on AI rollouts, fundraising, GTM, or founder strategy. I prep a short doc with specifics before the call so we use the hour for actual problem-solving, not context.

Your mentor

I help two kinds of people: early-stage founders going from idea to first traction, and operators trying to actually implement AI in a way that moves business metrics, not slides.

Over the past 9+ years I've held product and AI leadership roles at Rozetka and Intercom, launched 10+ products, and founded my own startups (Stamina AI, ExoChat). I've raised funding for my own ventures and helped other founders raise $10M+ combined, through pitch sharpening, narrative framing, and the honest investor prep that closes the gap between a polite 'no' and a real check.

Currently I lead AI implementation at a scaled product company, deploying agentic AI across product, marketing, and operations. That means I'm not advising from theory. I'm dealing in real time with the same tradeoffs you'll face when you actually try to put AI into a business: where it works, where it doesn't, and how to ship it without your team mutinying.

I work best with:
• Pre-seed and seed founders building B2B SaaS or AI products and getting ready to raise
• Non-US founders looking to crack the US market
• Operators and product leaders rolling out AI inside their company who want a real implementation roadmap, not generic advice

Recent wins:
• CEE founder entering the US with a B2B AI product. We rewrote the narrative around a single ICP wedge and cut the deck from 18 slides to 11. Closed $1.4M pre-seed six weeks later after three prior months of polite passes.
• Solo technical founder, strong product but losing investors at the data-room stage. Rebuilt the metrics page around retention cohorts instead of revenue. Closed $2.6M seed in the next two weeks.
• First-time founder, B2B SaaS idea and zero customers. Switched from broad outbound to 20 hand-picked design partners with paid pilots. Got to $4.2k MRR in 9 weeks, enough signal to start raising.

I won't just nod along. I'll tell you what's distracting you from the real bottleneck and when you're optimizing the wrong thing. The founder journey isn't linear, and I also know the psychological side matters as much as the product one.

I work in English, Russian, and Spanish, and have mentored founders across the US, EU, LATAM, and CEE.

Book an intro call or send me a quick message about your situation. Let's figure out if I'm the right fit.

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Oleg Karakash
$199
/
4.9
/
🇺🇸
Continue to booking

Scheduling conflict? No-show? Cancel session & get your money back instantly.

Limited spots Only 4 Spots Left