Oleg Poskotin

Built a $10M+/yr business that runs without me. I build AI agents for service businesses. DM "AI".

[GREG ISENBERG @gregisenberg]

I just got back from SF and I FEEL INSPIRED.

I spent 5 days with frontier AI model teams, AI startup founders, and 3 billionaires.

My takeaways:

1. I had lunch with 3 billionaires. All of them are buying SaaS companies and rebuilding them agent-first. They were deeply inspired by Bending Spoons and Ryan Cohen's eBay deal. Buy the company, cut the headcount, rebuild the tech, add agents, add features, make more valuable experience, raise prices.

2. The frontier model companies are hungry for usage data from the field. They can see API calls and token counts. They can't see the actual workflows. If you're deep in a niche using these models in ways the model companies haven't seen, that understanding is incredibly valuable. Usage intelligence is the new alpha.

3. Consumer AI is massively underbuilt. Every billboard in SF is either B2B inference infrastructure or vertical agent companies. The entire city is optimized for enterprise. Meanwhile you have companies like Cal AI doing $50M ARR in 18 months as a consumer app. I met with a cool few teams doing consumer AI (@paulscherer / @ekuyda)

4. MCP came up in literally every conversation. The companies exposing their product as MCP endpoints are getting pulled into deals they never pitched for. The ones that aren't are becoming invisible to agents. This is the new SEO. If agents can't find you, you don't exist. Building products for agents is the new zeitgeist in general.

5. Not uncommon for hot seed rounds to be $25-50 million valuations. I saw a Series A at $450 million

6. If I had a dollar every time someone mentioned "forward-deployed engineer" this trip I could have funded a seed round. It's the hottest role in SF right now. The person who sits between the agent and the customer, making sure everything actually works.

7. The mood around open source shifted. A year ago it felt like open source was chasing the frontier models. Now founders are telling me Gemma and DeepSeek are good enough for 80% of what they need at a fraction of the cost. The "which model do you use" conversation is being replaced by "which model for which task." Model loyalty kinda feels dead.

8. Voice agents came up more than I expected. Multiple founders told me voice is the interface for the next billion users. The billion people who will never type a prompt will absolutely talk to one.

9. The Obsidian community in SF is weirdly intense. Multiple founders showed me their vaults unprompted. Like showing someone your home gym. It's a flex now. The quality of your knowledge base (second brain?) is becoming a status symbol among builders.

10. Maybe it was just the people I met but the age of the founders is shifting. I met more founders over 40 this trip than any trip before and more founders under age 21 than ever before. Founders getting older and younger at the same time.

11. I spoke to a lot of fast-growing startups, VCs and frontier models who are hiring content creators right now.

12. The restaurant scene in SF is actually better than it's been in years. Founders are going out more. Alcohol is out, not surprisingly.

13. SF doesn't feel like the only place anymore. We all have access to the same frontier models. We all read the same X feed. A founder in NYC or Lagos is calling the same APIs as a founder in SoMa. So in the past it felt like SF was always lightyears ahead, doesn't feel that way anymore. It's okay not to live in SF and have BIG DREAMS.

14. The coworking spaces in SF are half empty but the coffee shops are packed. People want to be around people. I had a few startup ideas here....

15. Walking around the Mission I noticed something: the street-level businesses, the taquerias, the barbershops, the laundromats, none of them use any AI at all.

16. I heard the phrase "agent debt" for the first time. Like technical debt but for agents. When you hack together an agent workflow fast and never clean it up, the system prompts conflict, the memory gets polluted, the tools overlap. 6 months later the agent is doing weird things and nobody knows why lol.

17. Met a few people who carry two phones now. One for personal. One that's basically an agent terminal running Telegram or iMessage connections to their agent fleet.

It's always amazing to get that dose of inspiration in SF. I FEEL INSPIRED.

But I'm so happy to be back home, locked in and building.

We're 12-18 months into a shift that will take 15 years to play out. The urgency in every conversation was real.

What an incredible time to be building.

[Oleg Poskotin @olegfn]

@Connected_Data LLC wiki

[@jason @Jason]

The number one goal on tech right now is to kill openclaw

we can't let that happen

[Oleg Poskotin @olegfn]

@Jason definitely not!

[Oleg Poskotin @olegfn]

3/

**The Decision Maker Finder**

"Who else will be involved in making this decision with you?"

Avoids the classic mistake of spending hours with someone who can't actually say yes.

Especially important with couples and investors.

[Oleg Poskotin @olegfn]

2/

**The Timeline Detector**

"What's driving your timeline to move? Are you looking to buy in the next 3 months, or are you in the early research phase?"

This separates serious buyers from tire-kickers instantly.

Different answers = different nurture paths.

[Oleg Poskotin @olegfn]

5/

Step 4: Smart escalation
Radio silence after 2 hours = automatic staff alert. They can call or text from the same thread. Track response rates to dial in timing.

[Oleg Poskotin @olegfn]

4/

Step 3: Morning-of final check
Simple yes/no text at 9am. No response? Staff gets pinged for phone follow-up. Last shot to fill the slot if they bail.

[Oleg Poskotin @olegfn]

Not paranoia - experience. Don't be the cautionary tale at the next business meetup. Test your AI. Protect your business. Want agents with actual guardrails? DM me.

[Oleg Poskotin @olegfn]

Breaking: OpenAI just acquired Promptfoo - an AI security testing platform. If the company that BUILT ChatGPT thinks AI agents need security testing, what does that say about the chatbot you plugged into your business with zero guardrails?

[Oleg Poskotin @olegfn]

What actually breaks:
- Prompt injection (customers trick your bot)
- Data leaks (wrong info, wrong person)
- Brand disasters (AI says something awful)
- Lost money (can't handle basic edge cases)

At RobinClaw, we test every agent before it talks to customers.

[Oleg Poskotin @olegfn]

Not paranoia - experience. Don't be the cautionary tale at the next business meetup. Test your AI. Protect your business. Want agents with actual guardrails? DM me.

[Oleg Poskotin @olegfn]

If OpenAI - the company that built ChatGPT - thinks AI agents need security testing, what does that say about the chatbot you just plugged into your business? They just bought Promptfoo, a company that does "red-teaming" (basically trying to break AI before customers do).

[Oleg Poskotin @olegfn]

What actually breaks:
- Prompt injection (customers trick your bot)
- Data leaks (wrong info, wrong person)
- Brand disasters (AI says something awful)
- Lost money (can't handle basic edge cases)

At RobinClaw, we test every agent before it talks to customers.