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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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