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: NotionBoost 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/puzzlePuzzle📈  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

In this first episode of Season 2, Sasha Orloff is joined by Matt Tait, CEO of Decimal, to discuss the rise of AI in accounting, Decimal’s recent acquisition of KPMG Spark, and their new strategic partnership with Puzzle. Matt also covers his journey building Decimal, the balance of human expertise in a tech-driven world, and the industry’s future.--SPONSORS: 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/FoundFound provides small business owners tools to track expenses, calculate taxes, manage cashflow, send invoices and more. Open a Found account for free at https://found.com/econ102--RECOMMENDED IN THIS EPISODE:https://www.linkedin.com/in/mtait83/https://www.decimal.com/--X/SOCIAL:@GoDecimal (Decimal)@sashaorloff (Sasha)--TIMESTAMPS:(00:00) Intro(00:59) Season 2 changes(01:48) Exciting times in accounting(03:12) Interview with Matt Tate, CEO of Decimal(04:22) Rise and fall of Bench(06:18) Challenges in the accounting industry(13:03) Founding and vision of Decimal(16:46) Sponsors: Puzzle | Found(18:34) Acquisition of KPMG Spark(23:11) Team collaboration and roadmap insights(23:45) Scaling with Puzzle's AI native ledger(24:31) Evaluating technology partnerships(28:59) Role of trust and accountability in accounting(29:43) AI's impact on client experience(31:08) Human interaction vs. full automation(36:22) Future of AI in accounting(43:34) Implementing AI tools at scale(45:14) Wrap

David Hartley, a seasoned CPA and former CIO, dives into the fascinating evolution of accounting from quill to AI. He discusses the critical role technology plays in the profession today, noting the major challenges and opportunities posed by AI and automation. With 75% of CPAs nearing retirement, he highlights a looming talent gap in the field. Despite advancements, Hartley emphasizes the unwavering importance of trust and human insight, positioning AI as a partner rather than a replacement in the accounting landscape.

In this conversation, Andrew Gazdecki, founder of Acquire.com, draws from his impressive experience in facilitating over $500 million in successful exits. He emphasizes the importance of creating a competitive bidding process and how having multiple buyers enhances exit value. Andrew discusses the necessity of thorough preparation and transparent communication about business challenges to build trust. He also touches on the financial advantages of Qualified Small Business Stock and adapts to changing regulations in the evolving crypto landscape.

In this discussion, co-founders Daniel Kivatinos, a pioneer in iPad medical records, and Anelya Grant, a former YC accountant from Kazakhstan, delve into their revolutionary platform JustPaid. They explore the challenges in accounts receivable management and introduce the CHARGE framework to streamline billing processes. The duo shares their personal journeys of innovation, emphasizing the transformative potential of AI finance agents in startups. Listeners will gain insights into enhancing financial communication and operational efficiency with cutting-edge technology.

In this discussion, Matt Lerner, a growth leader and former PayPal executive, shares insights from his book 'Growth Levers.' He emphasizes how understanding customer needs is critical for startup success. Lerner advises on identifying the 10% of efforts that yield 90% of growth and the importance of rapid experimentation. He explores common pitfalls founders face and the significance of effective messaging and user retention strategies. The conversation also highlights the contrast between the writing process and agile startup methodologies.

Nicolas Boucher, a finance influencer with nearly a million LinkedIn followers, shares his journey from corporate finance to content creation. He discusses the viral success of his free finance courses and their impact on financial education. The conversation delves into AI’s transformative role in finance, its impact on jobs, and the evolving skill set needed in the industry. Boucher emphasizes the importance of communication and community, advocating for continuous learning to navigate the tech-driven future of finance.

Andrés Ugarte, founder of Copilot Money and former tech executive at Groupon and Google, discusses the upheaval in personal finance following the shutdown of Mint. He shares his journey from frustrated user to entrepreneur, emphasizing the importance of trust and user experience in a crowded market. The conversation delves into strategies for managing user transitions and expectations amidst significant service changes, as well as the challenges of scaling operations and maintaining customer support during rapid growth.

In this discussion, Paul Barnhurst, a dedicated FP&A educator and founder of several podcasts, sheds light on the role of Financial Planning and Analysis in modern business. He emphasizes the need for effective communication and strategic budgeting techniques, especially with the integration of AI tools like ChatGPT. Paul also discusses the shift in FP&A education and the importance of storytelling for clarity in data visualization. He highlights the evolving partnership between CEOs and FP&A professionals in navigating challenges and enhancing financial outcomes.

In this insightful discussion, Brad Wiskirchen, the mastermind behind Kount, shares his remarkable journey in bootstrapping the AI-driven fraud prevention firm that sold to Equifax for a staggering $640 million. He delves into the complexities of navigating business growth, stressing the importance of selecting the right funding partners and transparent communication. Brad also explores the intricate dynamics of mergers and acquisitions, revealing key strategies for successful negotiation, especially during challenging times like the COVID-19 pandemic.