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Ep. 304 How I Raised It with Yoav Oz of Rep AI

·36 min·2 clips

Yoav Oz describes a first acquisition proposal above $150 million that the board initially rejected.

1. How I Raised It episode 304 centers on Yoav Oz and HelloRepAI, an AI sales chatbot built for e-commerce websites. 2. Nathan Beckert hosts Yoav Oz, who comes from Tel Aviv and describes HelloRepAI as a company that “mimicked the salesperson” for online stores. 3. The episode asks how a founder from Israel raised from U.S. investors while building an AI product that tries to reduce e-commerce drop-off. 4. Yoav Oz says HelloRepAI collects “more than 500 data points” from new website visitors, including source, mouse speed, and movement between pages. 5. He says those signals give the system about “92% accuracy” in predicting when someone is about to leave. 6. He compares the product to a great brick-and-mortar salesperson who waits, observes behavior, and then approaches with the right offer. 7. He says the AI layer combines behavioral prediction, emotion detection, and an LLM such as ChatGPT. 8. He says the company fits best when products are expensive or when catalogs are confusing, naming coffee, autoparts, pharma, clothing, and jewelry. 9. He traces the origin to his own online shopping habit, where he says he was buying only about 1% of the time. 10. He says the move from voice to text was a pivot, and that the company had to “fire all the clients” and switch direction. 11. He says the first company sale process was a “roller coaster” and that the first proposal was above $150 million. 12. He says the board initially did not want to sell, even after multiple proposals and long discussions. 13. He says the eventual sale happened for less than the first proposal, but still represented a major outcome. 14. He says early-stage investors evaluate four things: team, market, product, and pricing. 15. He says he organizes fundraising into tier one, tier two, and tier three VCs, and starts with tier one for feedback. 16. He says he asks investors about fund size, last funding date, sweet spot, and recent investments before wasting time on a mismatch. 17. He says a “let me get back to you” response usually means no, while a real yes leads to a meeting scheduled within a day. 18. The interview style is direct and tactical, with Nathan Beckert pressing on board dynamics, investor feedback, and U.S. company structure. 19. Founders raising cross-border seed or Series A capital will get the most value from this episode. 20. Listeners wanting product-market anecdotes without fundraising detail can probably skip it.

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