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.

SPONSORS:

Notion

Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at https://notion.com/startups/puzzle

Puzzle

📈 No more waiting for month's end. No more manual reconciliations, just financials that keep up with you. Puzzle is leading a new movement with an AI first ledger, built for speed, automation, and real time decision making. Join today at https://puzzle.io/

RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/ankurdahiya/

https://www.fifteenth.com

X/SOCIAL:

@sashaorloff (Sasha)

@ankurd (Ankur)

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