E38: AI-Powered Tax Solutions are Really Here, with Fifteenth Founder Ankur Dahiya

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