What happens when venture capital stops being reserved for a small group of institutions and accredited investors?

In this episode of This Month in Fintech, Sasha Pilch sits down with Sarah Pinto, Head of Robinhood Ventures, to discuss Robinhood’s push to open private-market investing to a much broader audience.

Sarah explains the thinking behind Robinhood Ventures and its new RV2 fund, which is designed to give retail investors exposure to early-stage companies, including businesses coming out of the Y Combinator ecosystem. They discuss why so much wealth creation now happens before companies reach the public markets, the challenge of giving everyday investors access without sacrificing quality, and why Robinhood believes it can compete for allocations in some of the most sought-after private companies.

Sarah also reflects on her path from Goldman Sachs and private equity to Emerson Collective and Robinhood, where her previous investments included companies such as Stripe and OpenAI. The conversation explores women’s participation in investing and wealth creation, the impact AI could have on the next generation of founders, and why Sarah believes expanding access to venture could create not only more investors, but more entrepreneurs.

A conversation about venture capital, access, AI, entrepreneurship, and who gets to participate in the upside of the next generation of technology companies.

Subscribe for more conversations with the builders shaping the future of fintech.

Connect with the Hosts & Guest

Sasha Pilch: https://www.linkedin.com/in/sasha-pilch

Sarah Pinto: https://www.linkedin.com/in/sarah-pinto-peyronel/

About This Month in Fintech

This Month in Fintech is our premiere showcase podcast.  Each month, Sasha Pilch will have a deep 1:1 conversation with the leaders in the fintech arena, exploring questions about the industries next moves, where to focus energies, and how to lead into the next chapters and paradigm shifting technologies change everything again.

Sasha Pilch is joined by Alan Imberman, CFO at Wealthfront, to talk about what it really takes to scale a modern fintech from early scrappiness to a successful IPO, without losing the product instincts that got you there.

The conversation starts with the finance leadership side: how the finance function changes across stages, why audits and regulation create discipline, and what the public-company jump demands behind the scenes, from bank selection to testing-the-waters meetings to the S-1 feedback loop. Alan shares what the “ring the bell” moment hides, and why telling the business story clearly becomes a core part of the job.

We also cover custodial accounts and tax gain harvesting, plus the early push into a mobile-first mortgage and refinancing product. Finally, we look at AI financial advice, LLM referrals, and how conversational AI could reshape client education and service.

Subscribe for more conversations with the builders shaping the future of fintech.

Connect with the Hosts & Guest

Sasha Pilch: https://www.linkedin.com/in/sasha-pilch

Alan Imberman: https://www.linkedin.com/in/alan-imberman-cfa-aab2371/

About This Month in Fintech

This Month in Fintech is our premiere showcase podcast.  Each month, Sasha Pilch will have a deep 1:1 conversation with the leaders in the fintech arena, exploring questions about the industries next moves, where to focus energies, and how to lead into the next chapters and paradigm shifting technologies change everything again.

AI is changing how people shop, but the real story is what happens after the recommendation. When buying moves into ChatGPT-style interfaces, merchants suddenly face a new maze of platforms, protocols, and trust questions and nobody wants to rebuild checkout for every new “browser” of the AI era. We sit down with Karan, VP, Head of Agentic Commerce at Adyen, to get specific about what’s real today, what’s still early, and what infrastructure has to exist before agents can safely transact at scale. 

We break agentic commerce into four clear models: human-in-the-loop conversational checkout, consumer autonomous purchasing, machine-to-machine transactions, and B2B agentic procurement. Then we dig into the “universal translator” approach: real-time product feeds for discovery, cart creation that plugs into a merchant’s existing tax and fulfillment stack, and a payments trust layer that keeps transactions secure while preserving the merchant as merchant of record.

Subscribe for more conversations with the builders shaping the future of fintech.

Connect with the Hosts & Guest

Sasha Pilch: https://www.linkedin.com/in/sasha-pilch

Karan Katyal: https://www.linkedin.com/in/karan-katyal-14070438/

About This Month in Fintech

This Month in Fintech is our premiere showcase podcast.  Each month, Sasha Pilch will have a deep 1:1 conversation with the leaders in the fintech arena, exploring questions about the industries next moves, where to focus energies, and how to lead into the next chapters and paradigm shifting technologies change everything aga

In this episode, host Sasha Pilch sits down with John Glasgow, CEO and CFO of Campfire, to explore what it takes to build an AI-native ERP for modern finance teams.

John shares why the next major shift in accounting software is not from on-premise systems to the cloud, but from cloud tools to AI-native platforms. They discuss the reporting, consolidation, and planning challenges that still force finance teams into spreadsheets, along with Campfire’s approach to automating routine workflows while keeping governance and business context at the center.

The conversation also covers John’s path from investment banking and corporate finance at Adobe to building Campfire through Y Combinator, plus his view on how AI agents and connected data can change the role of the general ledger.

Subscribe for more conversations with the builders shaping the future of fintech.

This episode is sponsored by Granola. Try it free for 3 months at granola.ai/thisweekinfintech using code THISWEEKINFINTECH.

Connect with the Hosts & Guest

Sasha Pilch: https://www.linkedin.com/in/sasha-pilch

John Gasglow: https://www.linkedin.com/in/johnglasgow/

About This Month in Fintech

This Month in Fintech is our premiere showcase podcast.  Each month, Sasha Pilch will have a deep 1:1 conversation with the leaders in the fintech arena, exploring questions about the industries next moves, where to focus energies, and how to lead into the next chapters and paradigm shifting technologies change everything aga

AI agents can already shop, compare prices, and check out for you — but would you actually trust one with your credit card?

In this episode of This Month in Fintech host Sasha Pilch sits down with Kathleen Peters, Chief Innovation Officer at Experian, to explore the trust layer behind agentic commerce. From the shift from KYC to KYA (“Know Your Agent”) to Experian Agent Trust and digital identity tokens, they unpack how AI-driven payments could become safer for consumers, merchants, and the broader financial ecosystem.

They also dive into fraud prevention, open standards, Cloudflare, Visa, stablecoins, and what trustworthy agentic transactions could look like in the real world.

Subscribe for more conversations with the builders shaping the future of fintech.

This episode is sponsored by Granola. Try it free for 3 months at granola.ai/thisweekinfintech using code THISWEEKINFINTECH.

Connect with the Hosts & Guest

Sasha Pilch: https://www.linkedin.com/in/sasha-pilch

Kathleen Peters: https://www.linkedin.com/in/kathleenhpeters/

About This Month in Fintech

This Month in Fintech is our premiere showcase podcast.  Each month, Sasha Pilch will have a deep 1:1 conversation with the leaders in the fintech arena, exploring questions about the industries next moves, where to focus energies, and how to lead into the next chapters and paradigm shifting technologies change everything aga

In this episode of This Month in Fintech, Sasha Pilch sits down with Ximena Aleman, Co-founder and Co-CEO of Prometeo, to unpack what it really takes to build a single banking API across Latin America and the US.

They dig into the realities of cross-border fintech infrastructure, from early workarounds like screen scraping to the impact of Brazil’s open banking movement, and how Prometeo is pushing banks toward API adoption. Ximena also shares lessons from scaling across fragmented markets, raising a Series A during a downturn, and navigating the challenges founders face in LATAM.

They also explore where LATAM fintech could gain ground in the US, from cross-border payments and remittances to new approaches to credit for underserved populations.

Subscribe for more conversations with the builders shaping the future of fintech.

This episode is sponsored by Granola. Try it free for 3 months at granola.ai/thisweekinfintech using code THISWEEKINFINTECH.

Connect with the Hosts & Guest

Sasha Pilch: https://www.linkedin.com/in/sasha-pilch

Ximena Aleman: https://www.linkedin.com/in/ximena-aleman/?locale=en_US

About This Month in Fintech

This Month in Fintech is our premiere showcase podcast.  Each month, Sasha Pilch will have a deep 1:1 conversation with the leaders in the fintech arena, exploring questions about the industries next moves, where to focus energies, and how to lead into the next chapters and paradigm shifting technologies change everything again.

We talk with FIS CEO Stephanie Ferris about building a career by leaning into risk, leading teams through complex M&A, and simplifying a legacy fintech business to focus on financial institutions. We also dig into why trust is the real infrastructure of banking, how tokenization is evolving, and why AI should make fintech leaders more optimistic, not fearful.

• Career path from PwC to Fifth Third to Vantiv to FIS, prioritizing tough roles and high learning curves
• How major M&A really happens, from long strategy conversations to relationship-driven execution
• Why FIS separates Worldpay and what the three-party transaction changes operationally
• Build versus buy in payments, and the scarcity of scaled credit card processing assets
• Trust as the foundation of financial services, lessons from SVB, 9/11, and COVID-era stress
• How banks and fintechs compete and partner, including shifting regulatory dynamics
• Stablecoins and tokenized deposits, practical use cases and what remains nascent in the US
• Imposter syndrome, coaching, and doing the reps as a leadership skill
• Generative AI as a strategic accelerant, and what it means for product delivery and speed

Connect with the Host & Guest

Sasha Pilch: https://www.linkedin.com/in/sasha-pilch

Stephanie Ferris: https://www.linkedin.com/in/stephanieferris

We sit down with Xero’s CTO/CPO Diya Jolly to unpack how AI, product conviction, and human judgment are reshaping small business finance. From JAX, Xero’s financial superagent, to passwordless lessons at Okta, we dig into saving time, making better calls, and building faster.

• Xero vs QuickBooks and why orchestration matters
• Jax as a unified financial superagent
• Transparent automation that invites human override
• Data moats and domain depth as AI advantages
• Focus markets across ANZ, US and UK
• Auto bank reconciliation and 22 hours saved per month
• One leader across product and technology
• Reversible vs one-way-door decisions and speed
• Career jumps for learning over brand
• Betting on passwordless and proving security with less friction
• Google lessons on pairing data with intuition
• The next decade of fintech UX beyond dashboards

Connect with the Host & Guest

Sasha Pilch: https://www.linkedin.com/in/sasha-pilch

Diya Jolly: https://www.linkedin.com/in/diyajolly/

Announcing the next chapter of the This Month in Fintech Podcast.

We are excited to welcome Sasha Pilch as the new host, leading conversations with the founders, operators, and thinkers shaping the future of fintech.

Each episode will explore the ideas, products, and decisions driving the next generation of fintech, from AI and financial infrastructure to the platforms redefining how businesses and consumers interact with money.

Join Sasha as she sits down with leaders across the ecosystem to unpack what is working, what is changing, and what comes next for the global fintech community.

Tune in for thoughtful conversations, practical insights, and a front row seat to the people building the future of finance.

In today’s episode, Ryan Zauk sits down with Bret Taylor, Co-Founder & CEO of Sierra and Chairman of the Board at OpenAI. 

Bret’s career is the stuff of valley legend…he is the former Co-CEO of Salesforce, former CTO of Facebook, and has been credited with building products like Google Maps and Facebook's 'Like' button. 

There may not be anyone closer to AI, spanning the app layer all the way down to its core foundation.

In this episode, Bret and Ryan explore several topics including how Sierra has transformed customer service, the agentic era and its consequences for software, why we ‘might’ be in an AI bubble, how Sierra differentiates to win customers like Ramp, Rocket, and Brex, where AI moats will accrue, the 3 AI megatrends he’s leaning into, and much more.

Key Takeaways
“Every company’s AI agent will be as important as their mobile app or their website.” Bret sees a future where AI agents replace apps and websites as the first point of contact for customers. Agents will handle workflows end to end (fraud reports, mortgage refis, account changes) across all channels, languages, and modalities.

CS agents are showing immediate ROI on both the top and bottom line…For example, Rocket’s customers who engage with a Sierra agent are 3x as likely to complete a transaction vs. traditional service. At Ramp, their self-service resolution rate with Sierra’s agents is over 90%. Healthcare giant Cigna is replatforming its IVR with Sierra…using AI will help businesses rethink their operating model.
Outcome pricing raises the stakes for software, morphing them into true business partners. Outcome pricing will create accountability, transparency, and measurable ROI in an era of vague productivity claims.

The Future of AI is 3 things. 1) Multimodal - seamless voice experience. 2) Personalized - knowing your context, preferences, and intent. 3) Proactive - solving a problem before it arises or before the customer knows it has occurred. 

It’s an AI bubble, but a healthy one. The fundraising hype is alarming, but the underlying transformation is real. Similar to 1999, many firms will fail, but some will become generational winners. If you bought pets.com you lost your money. If you bought Amazon, you made history.