This week, Sasha Orloff and Worldpay Chief Product Officer Cindy Turner explore the shifting digital payments landscape—from stablecoins and agentic tech to global trends in account-to-account payments, regional behaviors, regulatory influences, and innovations like buy now, pay later.

--

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/lucinda-turner/

⁠http://www.worldpay.com

--

X/SOCIAL:

@Worldpay_Global (Worldpay)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:58) Intro

(01:40) Meet Cindy Turner: Chief Product Officer of Worldpay

(02:08) Cindy Turner's career journey

(06:41) Global payments report

(10:01) Account-to-Account payments: A global perspective

(13:15) Sponsors: Notion | Puzzle

(14:55) Unlocking Open Banking

(17:10) E-commerce and digital payments trends

(20:33) Impact of surcharging in Australia

(21:56) Surcharging trends in the US

(23:23) Cash dominance in certain countries

(26:03) Rise of buy now, pay later

(29:39) Future of payments: Agentic commerce

(33:59) Stablecoins and the future of payments

(37:29) Optimizing payments for businesses

(38:50) Wrap

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 automation and human expertise, strategic market targeting, funding insights, and the transformative potential of AI in tax preparation.

--

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/jeandenisgreze/

https://town.com/

--

X/SOCIAL:

@jgreze (Jean)

@TownTaxCo (Town)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:48) Intro

(01:20) Jean-Denis Greze: The origin story of Town

(02:10) Challenges and opportunities in business tax prep

(03:41) Role of AI in automating tax preparation

(05:50) Market dynamics and constraints in tax services

(15:49) Sponsors: Notion | Puzzle

(17:14) Unique needs of small businesses

(24:38) Future of AI in tax preparation

(26:12) Segmenting the small business market

(27:15) Building trust and scaling AI

(37:14) Exploring AI agents and their potential

(47:21) Fundraising and future plans

(50:57) Wrap

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 cohesive ecosystems, highlighting breakthroughs in AI capabilities, the balance between automation and human input, and the future of work.

--

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/jaspar-carmichael-jack/

https://www.artisan.co/

--

X/SOCIAL:

@jasparcjack (Jaspar)

@GetArtisanAI (Artisan)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:38) Intro

(01:08) Jaspar Carmichael-Jack, Founder & CEO of Artisan

(02:53) Concept and evolution of Artisan

(04:09) Challenges and iterations in AI development

(05:09) Expanding Artisan's capabilities

(08:33) Future of AI in the workplace

(10:34) Sponsors: Notion | Puzzle

(11:58) From better data to smarter responses

(13:24) Funding and growth journey

(16:44) Balancing AI and human labor

(27:26) Fun and unusual use cases for AI

(28:45) Final thoughts and lessons learned

(31:09) Wrap

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 of machine learning have helped Wealthfront grow to $80 billion in assets and 1 million customers, while delivering lower fees, better rates, and sustainable wealth-building strategies.

--

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/alan-imberman-cfa-aab2371/

https://www.wealthfront.com/

--

X/SOCIAL:

@Wealthfront (Wealthfront)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:48) Intro

(01:16) Interview with Alan, CFO of Wealthfront

(01:54) Wealthfront's vision and growth

(03:24) Innovative financial products

(04:19) Profitability and business model

(06:03) New product launches and strategies

(15:18) Tax loss harvesting and direct indexing

(17:43) Sponsors: Notion | Puzzle

(19:23) Wealthfront’s tax strategy triumph

(23:13) Bond ladders explained

(28:11) Future of Wealthfront and AI in finance

(33:41) Advice for founders and finance leaders

(36:01) Wrap

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 from Netflix’s rise over Blockbuster, emphasizing innovation, practical AI adoption, and financial storytelling.

--

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/wouterborn/

https://cfooffice.io/

--

X/SOCIAL:

@wouter_born (Wouter)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:58) Intro

(01:26) Meet Wouter Born: From founder to AI influencer

(02:39) Wouter entrepreneurial journey

(05:30) Evolution of CFOs in the age of AI

(07:28) Practical AI Tips for CFOs and Founders

(13:01) Future tech stack for CFOs

(17:15) Sponsors: Notion | Puzzle

(18:40) Changing role of CFOs

(21:30) Importance of storytelling in finance

(23:32) Leveraging AI for financial storytelling

(25:54) Building financial tools with AI

(28:51) Future of CFO tech stack

(34:54) Practical advice for AI prompting

(38:39) Connecting with the community

(39:53) Wrap

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 prediction accuracy, AI-powered user experiences, pricing challenges, and insights for founders, investors, and job seekers.

--

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/meghbartma/

https://www.crunchbase.com/

--

X/SOCIAL:

@crunchbase

@skyspeak (Megh)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:35) Intro

(01:03) Megh Gautam, Crunchbase's Chief Product Officer

(01:48) Megh’s journey to Crunchbase

(04:26) Transitioning Crunchbase to an AI company

(07:06) Crunchbase's AI and data insights

(09:45) User engagement and product development

(14:58) Sponsors: Notion | Puzzle

(16:22) Forbes article on Crunchbase's AI model

(24:58) Pricing strategies and user experience

(29:33) Future of AI in product management

(35:53) Conclusion and future collaboration

(38:27) Wrap

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 workforce management challenges, domestic hiring shifts, employee termination rates, and the tools Deel provides to support global hires, with an emphasis on trust and asynchronous decision-making for productivity.

--

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/benjamin-cohen-0618308/

https://www.deel.com/

--

X/SOCIAL:

@deel

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:40) Intro

(01:51) Understanding Deal's global hiring report

(02:38) Insights on data utilization

(04:42) Collaboration and data storytelling

(08:23) Generational workforce trends

(08:41) Gen Z's impact on the workforce

(13:59) Sponsors: Notion | Puzzle

(15:39) Global hiring trends and challenges

(19:49) Introduction to global hiring trends

(20:28) Surprising rise of accountants

(22:52) Impact of AI on job market

(25:31) Employee terminations and market trends

(30:01) Tools and insights for global hiring

(33:06) Best practices for a global workforce

(36:33) Data analysis tools

(38:15) Wrap

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, investor interest from Marc Cuban and Jason Calacanis, its shift from a consumer tool to a B2B AI assistant for accountants, its unique advantages over general AI, and his own journey from Pakistan to Silicon Valley, culminating in Y Combinator and a vision for the future of AI-driven tax assistance.

--

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/chkashifali/

https://www.taxgpt.com/

--

X/SOCIAL:

@AskTaxGPT

@ChKashifAli (Kash)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:45) Intro

(01:14) Meet Kash Ali: The Journey Begins

(01:35) Inception of TaxGPT

(02:41) From side project to startup

(04:16) Securing the domain and early success

(07:13) Kash Ali's background and path to Silicon Valley

(13:11) Evolution of TaxGPT

(13:33) Sponsors: Notion | Puzzle

(14:59) TaxGPT's unique value proposition

(19:28) Future of TaxGPT and AI integration

(20:44) Evolution of AI models

(21:48) Enhancing workflows with frontier models

(23:03) Importance of prompting in AI

(28:13) Journey to Y Combinator

(29:55) Fundraising success and future vision

(33:06) Future of accounting and AI

(40:16) Adopting AI solutions in accounting firms

(41:29) Wrap

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 transaction protocols, the challenges of dynamic payment systems, the role of blockchain in security, and Nevermined's journey in enabling decentralized AI-to-AI transactions.

--

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/donald-gossen-40ab96/

https://nevermined.io/

--

X/SOCIAL:

@Nevermined_io

@dongossen (Donald)

@sashaorloff (Sasha)

--

TIMESTAMPS:

(00:00) Preview

(00:50) Intro

(01:18) Overview of AI-to-AI payments and decentralized finance

(02:34) Vision behind Nevermined

(04:01) Challenges in AI payment systems

(05:34) Nevermined: The PayPal of AI

(06:52) Future of AI commerce

(11:46) Real-world applications and security

(13:54) Sponsors: Notion | Puzzle

(15:17) Security & trust in AI transactions

(19:39) Evolution of AI agents

(27:45) Building Nevermined and fundraising

(32:31) Wrap

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:

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/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