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From mobile credit to autonomous accounting using financial data and AI, with Puzzle CEO Sasha Orloff

Lex chats with Sasha Orloff, CEO and Co-founder of Puzzle – “the first smart accounting software,” which combines a streaming financial data platform that’s connected to a general accounting ledger.

Sasha starts the conversation detailing his journey from traditional banking to fintech entrepreneurship.

Sasha Orloff headshot
Sasha Orloff

Reflecting on the early days of fintech, contrasting the East and West Coast perspectives, and sharing his experiences from leading innovative fintech ventures like LendUp. The conversation dives into the future of fintech, discussing the transition into autonomous accounting, the rise and fall of Personal Financial Management (PFM) tools, and the integration of natural language processing into quantitative software. The duo also contemplates the nature of rules in language models, the dichotomy between deterministic and probabilistic models in AI, and the future of intelligent software. The episode concludes with Sasha sharing various channels to connect with him and learn more about Puzzle.


Puzzle’s Website:

Sasha’s LinkedIn profile:

Topics: Fintech, AI, artificial intelligence, machine learning, GenAI, Accounting, Software, LLM, embedded finance

Companies: Puzzle, Puzzle Financial, Mission Lane, LendUp, ChatGPT, Brex, Stripe, Plaid


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1’43”: The evolution from traditional banking to fintech entrepreneurship: Exploring personal journey and the early days of fintech

7’10”: The East vs West Coast perspective in fintech’s infancy: Analyzing venture investments, startup culture, and the birth of innovative fintech ventures like LendUp

12’36”: Deciphering the keys to fintech success: The role of mobile distribution, underwriting capabilities, and capital flow in shaping lending ventures

18’23”: Transitioning into the realm of autonomous accounting: The genesis of Puzzle and its inevitable emergence in the fintech landscape

22’41”: Reflecting on the evolution of fintech: Assessing the impact of financial data accessibility, manufacturing financial products, and mistakes in early accounting software ventures

28’23”: The rise and fall of Personal Financial Management (PFM) tools: Evaluating consumer adoption, value proposition, and the role of autonomous accounting in fintech’s future

34’47”: Exploring the integration of natural language processing into quantitative software: The role of language models in user experience and backend operations

39’04”: Deciphering the nature of rules in language models: Deterministic vs. Probabilistic approaches in accounting software

41’59”: Speculating the future of AI: A dichotomy between deterministic structures and probabilistic models in building intelligent software

46’10”: The channels used to connect with Sasha & learn more about Puzzle

  • Lex Sokolin

    Chief Cryptoeconomist @Consensys , repeat fintech founder, artist in love with systems. Follow me for insider analysis of Web3, Fintech, and DeFi.