"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech

Sasha Orloff sits down with Solon Angel, CEO of Remitian, to explore why tax payments remain one of fintech's most overlooked infrastructure problems. They discuss the outdated systems still powering tax compliance, how AI agents are enabling a new payments layer for accountants and taxpayers, and why the convergence of regulatory change, fraud prevention, and agentic AI could transform the $7 trillion tax payment ecosystem into a seamless, deadline-free experience.

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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/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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RECOMMENDED IN THIS EPISODE:

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

https://remitian.com/

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X/SOCIAL:

@Remitian_app (Remitian)

@sashaorloff (Sasha)

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TIMESTAMPS:

(00:00) Preview
(00:51) Intro
(02:23) Why tax payments are broken
(06:07) Trust accounts and theft risks
(07:59) Golden Gate Bridge analogy
(09:14) DeepMind sparked MindBridge
(11:12) Humans stay in the loop
(12:46) Why VCs finally care
(15:38) Sponsors: Notion | Puzzle
(17:02) Play your own game
(19:37) Finding the Remitian opportunity
(22:18) Tax payments before Remitian
(24:14) Why it wasn't solved
(26:25) Hybrid AI with humans
(28:39) Scaling partnerships and sovereignty
(32:04) Customer collaboration culture
(36:13) Legal breakthrough for CPAs
(37:02) Who needs this most
(40:29) Fundraising and API wedge
(42:34) Future no tax deadlines
(44:20) Naming the AI agents
(47:28) Wrap

Sasha Orloff and Jeff Grimes, Perplexity’s Product Lead for Finance, explore the evolution of search from a simple "answer engine" to a high-stakes "action engine." They discuss the disruption of legacy platforms like the Bloomberg Terminal and how Perplexity is building an AI-native operating system designed specifically for the rigors of financial analysis. The conversation tackles the industry's skepticism toward AI accuracy, detailing the "auditability-first" approach that allows finance teams to verify every data point back to its original SEC filing, effectively turning complex technical workflows into plain-English commands.

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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/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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RECOMMENDED IN THIS EPISODE:

https://www.linkedin.com/in/jeffgrimes9/

https://www.perplexity.ai/finance

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X/SOCIAL:

@jeffgrimes9 (Jeff)

@sashaorloff (Sasha)

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TIMESTAMPS:

(00:00) Preview

(00:50) Intro

(02:28) Why it went viral

(06:50) Comet and agentic browsing

(08:57) WSJ controversy breakdown

(10:40) What versus How

(12:52) Google innovators dilemma

(14:33) Sponsors: Notion | Puzzle

(16:13) Perplexity finance users

(18:24) Off the shelf data deals

(22:37) Future of finance workflows

(26:19) Workflows and automation

(27:05) Proactive assistants

(28:28) Trust in finance

(31:31) Audit trails by design

(34:20) Getting started with computer

(36:16) Multi model orchestration

(37:47) Wild user stories

(39:48) Domain specific finance

(41:40) Where to learn more

(42:28) Wrap

In this episode, Sasha Orloff sits down with Luke Frye, founder of LukeFrye.co, to trace his decade-long journey through foundational fintech pioneers like Bench and Pilot and explore how AI is shifting the accountant's role from manual data entry to "architecting" financial systems and human-centric advisory.

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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/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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RECOMMENDED IN THIS EPISODE:

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

https://lukefrye.co/

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X/SOCIAL:

@LukeFrye (Luke)

@sashaorloff (Sasha)

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TIMESTAMPS:

(00:00) Preview

(00:37) Intro

(02:14) From Wyoming To Techstars

(05:49) Bench origin story

(07:11) Automating accounting tension

(09:20) Bench growth playbook

(11:06) Early sales and scale

(14:28) Sponsors: Notion | Puzzle

(15:53) Bench cracks and incentives

(18:59) Tax experiment trainwreck

(21:38) Solo practice to Pilot

(23:51) Pilot tech stack shift

(24:48) Sales ops balance

(26:36) From Pilot to Rivet

(27:18) Why Puzzle mattered

(29:17) Modern tax software gap

(31:12) Automation limits today

(34:33) AI makes us human

(37:06) Where firms should start

(39:19) Vision values planning

(42:43) Future firm architect

(44:57) Wrap

In this episode, Sasha Orloff speaks with Greg Capitolo, Co-founder and Partner at Attivo Partner, to discuss how fractional finance teams are transitioning from manual bookkeeping to AI-driven advisory roles, emphasizing the shift toward "real-time data-driven decision making" over traditional month-end closes.

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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/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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RECOMMENDED IN THIS EPISODE:

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

http://www.attivopartners.com

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X/SOCIAL:

@sashaorloff (Sasha)

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TIMESTAMPS:

(00:00) Preview

(00:39) Intro

(02:07) Meet Greg Capitolo of Attivo Partner

(03:26) Who Attivo serves

(04:07) Why VCs recommend

(06:40) Founder trigger points

(08:50) AI outlook

(10:59) AI boosts advisory

(15:19) Creating 10x accountants

(19:51) Sponsors: Notion | Puzzle

(21:14) Pricing and billing shift

(23:41) Choosing AI tools

(27:06) Human in the loop

(30:22) Accounting needs accountants

(32:09) Real time data

(35:14) Tool evaluation framework

(38:54) Growth mindset future

(40:56) Wrap

In this episode, Sasha Orloff speaks with Tarek Alaruri, CEO and Co-founder of Stuut, about raising a Series A from Andreessen Horowitz to build an AI-powered accounts receivable platform that automates the entire AR function—from credit and collections to cash application and disputes—delivering a 40% reduction in DSO in the first six months compared to the 3% improvement from legacy software, while implementing in just 3.6 days for mid-market and Fortune 100 companies.

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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/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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RECOMMENDED IN THIS EPISODE:

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

https://www.stuut.ai/

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X/SOCIAL:

@TAlaruri (Tarek)

@sashaorloff (Sasha)

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TIMESTAMPS:

(00:00) Preview

(00:42) Intro

(01:25) Interview with Tarek Alaruri, CEO of Stuut

(01:50) Problem with traditional accounts receivable

(03:31) How AI is transforming accounts receivable

(05:39) Stuut's mission and impact

(08:17) Future of AI in finance

(09:55) Customer experience and AI solutions

(11:35) Evolution of AI and business processes

(14:04) Sponsors: Notion | Puzzle

(15:31) Eliminating clicks with Stuut

(17:07) AI in B2B transactions

(21:56) Role of AR teams today and tomorrow

(23:38) Fundraising insights and strategies

(30:46) Building enterprise AI and future outlook

(35:12) Wrap