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 They discuss the outdated systems still powering tax compliance, how AI agents are enabling a new payments layer for accountants and taxpayers, and why the convergence of regulatory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.

--

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/innovationforall/

https://remitian.com/

--

X/SOCIAL:

@Remitian_app (Remitian)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

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.

--

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/jeffgrimes9/

https://www.perplexity.ai/finance

--

X/SOCIAL:

@jeffgrimes9 (Jeff)

@sashaorloff (Sasha)

--

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.

--

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/lukefrye/

https://lukefrye.co/

--

X/SOCIAL:

@LukeFrye (Luke)

@sashaorloff (Sasha)

--

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.

--

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/gregcapitolo/

http://www.attivopartners.com

--

X/SOCIAL:

@sashaorloff (Sasha)

--

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.

--

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/tarekalaruri/

https://www.stuut.ai/

--

X/SOCIAL:

@TAlaruri (Tarek)

@sashaorloff (Sasha)

--

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

In this episode, Sasha Orloff sits down with Sam Ross, co-founder and CEO of Numeral and former product leader at Teespring and Airbnb, about raising Series B funding from Mayfield (following Benchmark's Series A and Uncork's seed) to build what he calls "the most boring AI company"—an end-to-end sales tax automation platform that uses AI to eliminate the manual burden of multi-state and international tax compliance for e-commerce and SaaS businesses, transforming a traditionally services-heavy industry into a fully automated solution that handles everything from nexus analysis and registration to filings and government correspondence.

--

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/sambross/

https://www.numeral.com

--

X/SOCIAL:

@SpamRoss (Sam)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:49) Intro

(01:22) Guest Introduction: Sam Ross

(01:44) Most boring AI company

(03:54) AI and sales tax

(06:08) Origin story and early challenges

(10:56) Building the business and first customers

(13:14) Sponsors: Notion | Puzzle

(14:36) Sales tax compliance and solutions

(17:12) Automating mail and customer engagement

(18:24) E-commerce and tax compliance challenges

(19:40) Marketplace tax exposure issues

(22:15) Government complexities and physical mail

(23:54) Founding story and funding journey

(30:55) AI innovations in tax compliance

(33:11) Future of AI and browser automation

(34:33) Wrap

In this episode, Sasha Orloff speaks with Usman Gul, founder and CEO of Metal, about building an AI-driven operating system for fundraising backed by Y Combinator and Andreessen Horowitz that helps founders avoid wasting 80% of their investor meetings by using data-driven insights to identify the most likely investors based on historical funding patterns, industry benchmarks, and relationship intelligence across over 500,000 venture rounds.

--

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/gulsf/

http://www.metal.so

--

X/SOCIAL:

@usmangul (Usman)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:44) Intro

(01:28) Meet Usman Gul from Metal

(01:59) Genesis of Metal

(04:32) Metal's AI-driven fundraising solutions

(08:08) Common fundraising mistakes and solutions

(13:24) Sponsors: Notion | Puzzle

(14:15) Importance of modern tools for startups

(21:40) Metal manifesto

(24:35) Key indicators for successful fundraising

(25:53) Telling the right story to investors

(26:44) Challenges and insights from previous ventures

(27:13) Evolution of investor targeting

(28:38) Predictive intelligence and the future of Metal

(30:41) Current state of fundraising tools

(36:53) Building Metal with minimal capital

(39:19) Advice for founders on fundraising

(47:29) Wrap

In this episode, Sasha Orloff speaks with Renato Villanueva, Founder and CEO of Parallel, about his journey from finance professional at Divvy to raising $2.4 million from Bain Capital and K5 Tokyo Black for an AI-powered FP&A platform that helps founders model financial scenarios and make confident growth decisions. Renato shares lessons on building products founders are passionate about rather than forced wedges, nurturing investor relationships, and how Parallel's approach has enabled customers to achieve significant growth—including one company that scaled from planning one sales hire to four, ultimately raising one of Utah's biggest Series A rounds.

--

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/villanuevar/⁠

https://www.getparallel.com/

--

X/SOCIAL:

@_renatov (Renato)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(01:24) Intro

(02:09) Meet Renado Villanueva

(02:38) Renado's journey to founding Parallel

(04:02) Moment of decision

(04:45) Building the deck and quitting the job

(09:20) Challenges and insights in fundraising

(11:05) What Parallel actually does

(14:24) Sponsors: Notion | Puzzle

(15:49) Parallel’s target sweet spot

(16:49) Common mistakes founders make

(19:30) AI's role in finance decision-making

(20:15) Balancing flexibility and opinion in software

(23:11) Who should use Parallel?

(25:06) Excel vs. Parallel: Finding the right balance

(27:06) Evolution of FP&A tools

(31:24) Lessons learned from building Parallel

(35:34) Building and trusting a team

(38:31) Future of Parallel

(39:47) Wrap

In this episode, Sasha Orloff talks with Yogi Goel, Co-founder and CEO of Maxima, about raising $41 million from Kleiner Perkins and RedPoint Ventures to build an agentic AI platform for enterprise accounting that automates journal entries, reconciliations, and variance analysis for complex companies, helping them close their books 2-3 days faster with 98% automation while strengthening SOX controls and freeing accountants from mundane tasks.

--

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/yogi-goel/

https://www.maxima.ai/

--

X/SOCIAL:

@maxima_dot_ai (Maxima)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:50) Intro

(01:34) Introducing Yogi Goel and Maxima

(02:08) Problem with traditional accounting

(04:50) Birth of Maxima

(07:03) Maxima's solutions and innovations

(11:19) Sponsors: Notion | Puzzle

(12:43) Customer success stories

(25:08) Future of accounting with AI

(27:10) Fundraising and growth

(29:53) Advice for founders and CFOs

(34:15) Embracing AI: Overcoming fear and finding solutions

(35:56) Getting in touch with Maxima

(36:17) Story behind the name 'Maxima'

(37:01) Wrap

In this episode, Sasha Orloff sits down with Dan Westgarth, COO of Deel, to explore how the company scaled to 37,000 customers, processes $22B in payroll, and recently raised a $300M Series E to power global hiring in 150 countries. They dive into the future of back-office automation, including real-time payroll, AI-driven operations, and the push toward a unified, seamless global HR and accounting stack.

--

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/dan-westgarth-710650a4/

https://www.deel.com/

--

X/SOCIAL:

@DanWestgarth (Dan)

@deel (Deel)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:44) Introduction to Tech Finance

(01:25) Meet Dan Westgarth, COO of Deel

(02:18) Dan's journey with Revolut

(06:22) Building Deel's global infrastructure

(08:33) Managing global operations

(12:06) Expanding Deel's services

(19:56) Importance of consolidation

(21:15) Sponsors: Notion | Puzzle

(22:55) Common mistakes startups make

(24:09) Onboarding and implementation challenges

(25:46) Customer engagement and feedback

(28:23) Recruiting and hiring strategies

(31:27) Future of accounting and payroll

(40:53) Real-time payroll processing

(44:09) Wrap