This week, Sasha Orloff is joined by Ankur Dahiya, CEO and founder of Fifteenth, a B2B fintech startup using AI to modernize the tax industry, as they discuss his journey from navigating complex stock options at Flexport to transforming CPA services, the challenges of scaling a tax-focused business, the role of AI in automating tax processes, and his vision for more efficient, accessible tax advisory following a successful funding round.
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SPONSORS:
Notion
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Puzzle
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RECOMMENDED IN THIS EPISODE:
https://www.linkedin.com/in/ankurdahiya/
https://www.fifteenth.com
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X/SOCIAL:
@sashaorloff (Sasha)
@ankurd (Ankur)
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TIMESTAMPS:
(00:00) Intro
(01:37) Guest Introduction: Ankur Dahiya
(02:24) Problem with taxes
(03:01) Birth of Fifteenth
(08:33) Combining human expertise with AI
(12:22) Future of AI in tax solutions
(14:40) Sponsors: Notion | Puzzle
(16:03) Managing personal finances
(19:42) Fundraising and building the team
(25:49) Challenges and advice for founders
(27:55) Tax tips for founders and engineers
(33:12) Wrap
