In this episode of Future Finance, hosts Paul Barnhurst and Glenn Hopper sit down with Sasha Orloff, CEO of Puzzle, to discuss the future of accounting and how AI is poised to transform the finance industry. Sasha Orloff shares his journey from founding LendUp and Mission Lane to building Puzzle, an innovative accounting software platform designed to solve the industry’s most pressing challenges.

Sasha Orloff is the CEO of Puzzle, a modern accounting software platform focused on building the future of finance. Before Puzzle, Sasha Orloff founded LendUp and Mission Lane, which both scaled to hundreds of millions in revenue. He has a deep background in finance, technology, and AI, and his insights are helping to shape the next wave of innovation in the industry.

In this episode, you will discover:

1. The challenges of traditional accounting systems and outdated software
2. How AI and predictive analytics can streamline financial tasks and improve decisions
3. The need for an evolving general ledger and the role of blockchain in enhancing transparency
4. How AI reduces errors and provides more accurate insights for finance professionals
5. The future of accounting and how AI will enable faster, smarter decision-making

Sasha Orloff explains how Puzzle is addressing the foundational issues with traditional accounting software by focusing on trust, transparency, and flexibility. He also shares his thoughts on the importance of building the right data infrastructure to enable AI-driven insights in finance.

Join hosts Glenn and Paul as they unravel the complexities of AI in finance.

Follow Sasha:

LinkedIn: https://www.linkedin.com/in/sashaorloff/

Company: https://www.linkedin.com/company/puzzlefin/

Follow Glenn:

LinkedIn: https://www.linkedin.com/in/gbhopperiii

Follow Paul:

LinkedIn - https://www.linkedin.com/in/thefpandaguy

Follow QFlow.AI:

Website - https://bit.ly/4i1Ekjg

Future Finance is sponsored by QFlow.ai, the strategic finance platform solving the toughest part of planning and analysis: B2B revenue. Align sales, marketing, and finance, speed up decision-making, and lock in accountability with QFlow.ai.

Stay tuned for a deeper understanding of how AI is shaping the future of finance and what it means for businesses and individuals alike.

In Today’s Episode:

[01:00] - Meet Sasha Orloff

[03:30] - The Problem with Traditional Accounting Software

[06:00] - The Future of the General Ledger and Data Transparency

[10:30] - How AI Enhances Finance and Accounting Tasks

[12:45] - Blockchain’s Role in Financial Trust

[17:30] - The Role of AI in Business Decision-Making

[20:00] - How Puzzle is Revolutionizing...

In this episode of Future Finance, hosts Glenn Hopper and Paul Barnhurst are joined by Ian Wong, co-founder and CEO of Summation, a cutting-edge AI platform designed to help enterprise leaders navigate complex data and make smarter business decisions. Ian shares his journey from CTO at Opendoor to founding Summation, inspired by his frustration with the inefficiencies of traditional reporting and analysis systems.

Ian Wong is the co-founder and CEO of Summation, an AI-powered decision platform built to help enterprise leaders better understand how their businesses are performing. Before Summation, Ian co-founded Opendoor and served as CTO through its journey to going public. He was also Square’s first data scientist, where he built early fraud and risk systems. Ian holds degrees in electrical engineering and statistics from Stanford University and brings a rare blend of deep technical expertise and business leadership experience.

Expect to Learn:

1. The Monday Morning Problem and its impact on business operations
2. How AI can eliminate tedious data analysis processes
3. The difference between traditional BI tools and the AI-powered platform Summation
4. The importance of real-time, decision-grade data for enterprise leaders

Join hosts Glenn and Paul as they unravel the complexities of AI in finance:

Follow Ian:

LinkedIn: https://www.linkedin.com/in/ian-wong/

Company: https://www.linkedin.com/company/summation-hq/

Follow Paul:

LinkedIn - https://www.linkedin.com/in/thefpandaguy

Follow QFlow.AI:

Website - https://bit.ly/4i1Ekjg

Future Finance is sponsored by QFlow.ai, the strategic finance platform solving the toughest part of planning and analysis: B2B revenue. Align sales, marketing, and finance, speed up decision-making, and lock in accountability with QFlow.ai.

Stay tuned for a deeper understanding of how AI is shaping the future of finance and what it means for businesses and individuals alike.

In Today’s Episode:

[01:01] - The Monday Morning Problem and Decision-Making

[03:46] - The time and effort spent on manual data analysis

[08:48] - Ian’s Motivation Behind Summation

[10:40] - What Makes Summation Different

[12:48] - The Importance of Accurate Data in Finance

[13:53] - Wrapping Up and Farewell

In this episode of Future Finance, hosts Paul Barnhurst and Glenn Hopper sit down with Ian Wong, co-founder and CEO of Summation, to talk about one of the most frustrating challenges in finance and analytics: getting timely, trustworthy answers to basic business questions. Ian shares the story behind what he calls the “Monday Morning Problem” and explains why finance teams often spend weeks chasing insights that arrive too late to matter. The conversation explores the limits of dashboards, the risks of AI hallucinations in finance, and what decision-grade analytics really means.

Ian Wong is the co-founder and CEO of Summation, an AI-powered decision platform built to help enterprise leaders better understand how their businesses are performing. Before Summation, Ian co-founded Opendoor and served as CTO through its journey to going public. He was also Square’s first data scientist, where he built early fraud and risk systems. Ian holds degrees in electrical engineering and statistics from Stanford University and brings a rare blend of deep technical expertise and business leadership experience.

In this episode, you will discover:

• What the “Monday Morning Problem” is and why it slows down decision-making
• Why dashboards and ad hoc reports often fail finance leaders
• The risks of relying on generic AI tools for financial analysis
• How decision-grade analytics differ from conversational AI
• What the coming “query flood” could mean for data infrastructure and costs

Ian explains how Summation helps finance and operations teams move from manual data stitching to faster, more reliable insights. The discussion also covers AI hype versus reality, why trust matters so much in finance analytics, and how leaders can think more clearly about where AI fits into real business workflows.

Join hosts Glenn and Paul as they unravel the complexities of AI in finance.

Follow Ian:

LinkedIn: https://www.linkedin.com/in/ian-wong/

Company: https://www.linkedin.com/company/summation-hq/

Follow Glenn:

LinkedIn: https://www.linkedin.com/in/gbhopperiii

Follow Paul:

LinkedIn - https://www.linkedin.com/in/thefpandaguy

Follow QFlow.AI:

Website - https://bit.ly/4i1Ekjg

Future Finance is sponsored by QFlow.ai, the strategic finance platform solving the toughest part of planning and analysis: B2B revenue. Align sales, marketing, and finance, speed up decision-making, and lock in accountability with QFlow.ai.

Stay tuned for a deeper understanding of how AI is shaping the future of finance and what it means for businesses and individuals alike.

In Today’s Episode:

[01:58] – Meet Ian Wong

[05:25] – The “Monday Morning Problem”

[09:23] – What Empathetic Leadership Really Means

[13:15] – How Enterprise Research Really Works

[16:34] – The Monday Morning Numbers Meeting

[21:25] – A Balance Sheet That Still Doesn’t Balance

[25:53] – Where AI actually helps finance teams

[28:27] – The AI Hype Question of 2025

[33:07] – Moving into Personal Questions