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E46: Ex-Plaid CTO on Why Tax is the Ultimate AI Challenge, with Jean-Denis Greze
In this episode, Sasha Orloff talks with Jean-Denis Greze, Co-founder and CEO of Town, about building an AI-powered tax solution for SMBs, exploring the startup’s origin, the balance between automati…
Published on 3 months, 3 weeks ago
Artisan: Stop Hiring Humans, with Jaspar Carmichael-Jack
This week, Sasha Orloff sits down with Jaspar Carmichael-Jack, Founder & CEO of Artisan, about how their AI employees like Ava are transforming sales and workflows by integrating software into cohesi…
Published on 4 months, 2 weeks ago
From $2B to $80B: Wealthfront CFO Alan Imberman’s 10-Year Journey
In this episode, Sasha Orloff is joined Alan Imberman, CFO of Wealthfront, about how a client-first philosophy, transparent access, innovative products like S&P 500 Direct Indexing, and strategic use…
Published on 4 months, 3 weeks ago
The CFO's Blockbuster vs Netflix Moment: AI Adoption with Wouter Born
This week, Sasha Orloff is joined by Wouter Born, a finance, AI influencer, and General Partner at Born Capital to discuss how AI is reshaping the CFO role and financial tech stack, drawing lessons f…
Published on 5 months ago
Can AI predict the next unicorn. Crunchbase says yes with 95% accuracy.
This week, Sasha Orloff sits down with Megh Gautam, Chief Product Officer of Crunchbase, to explore the company’s evolution into an AI-driven intelligence platform, discussing its 95% unicorn predict…
Published on 5 months, 1 week ago
Surprising Trends from Deel's Data with Ben Cohen
This week, Sasha Orloff sits down with Ben Cohen, Head of Data from Deel to discuss the company's 2025 Global Hiring Report, covering trends in Gen Z salaries, rising demand for finance roles, global…
Published on 5 months, 2 weeks ago
The $500 Domain That Became a Multi-Million Dollar AI Tax Assistant with Kash Ali of TaxGPT
This week, Sasha Orloff is joined by Kash Ali, Founder and CEO of TaxGPT, who shares how a personal tax issue led to the platform’s creation, its rapid growth after Greg Brockman’s GPT-4 demo, invest…
Published on 5 months, 3 weeks ago
The AI Economy: How Agents Will Transact Without Us, with Don Gossen CEO of Nevermined
This week, Sasha Orloff sits down with Donald Gossen, CEO of Nevermined, to explore the future of AI-driven payments, highlighting the company's vision for AI agents with independent accounts and tra…
Published on 5 months, 4 weeks ago
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 stoc…
Published on 6 months ago
Using AI and Humans to Fix Accounting w/ Matt Tait, CEO of Decimal
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 pa…
Published on 7 months, 1 week ago