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"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
Puzzle, Turpentine
57 episodes
5 days ago
On Tech Finance, host Sasha Orloff brings you inside the office of the CFO - covering major tech finance news including funding announcements, deals, product launches, and emerging players shaping B2B fintech. We break down the week's biggest developments in finance tech and accounting, and explore how finance leaders are putting AI to work. Tech Finance is brought to you by Puzzle, the modern accounting platform with an AI-first ledger, built for speed, automation, and real time decision making. Learn more: puzzle.io Tech Finance is part of the Turpentine podcast network. Learn more: turpentine.co
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Management
Business,
Entrepreneurship
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All content for "Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech is the property of Puzzle, Turpentine and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
On Tech Finance, host Sasha Orloff brings you inside the office of the CFO - covering major tech finance news including funding announcements, deals, product launches, and emerging players shaping B2B fintech. We break down the week's biggest developments in finance tech and accounting, and explore how finance leaders are putting AI to work. Tech Finance is brought to you by Puzzle, the modern accounting platform with an AI-first ledger, built for speed, automation, and real time decision making. Learn more: puzzle.io Tech Finance is part of the Turpentine podcast network. Learn more: turpentine.co
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Management
Business,
Entrepreneurship
Episodes (20/57)
"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E57: Lessons from Brex, SVB, a16z: How Jason Mok Spots What Founders Need Before They Know It
In this episode, Sasha Orloff sits down with Jason Mok, VP & GM of Startups at Brex, about the company's evolution from credit cards to a comprehensive financial platform and their new partnership with Puzzle to offer "one-click accounting" that automatically sets up bookkeeping for startups during Brex onboarding, eliminating the friction that typically delays founders from getting proper financial infrastructure in place from day one. -- 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/jasonmok/ https://www.brex.com/ -- X/SOCIAL: @jasonmok (Jason) @brexHQ (Brex) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:50) Intro (01:18) Live from Brex offices with Jason Mock (02:19) Early days of Brex and startup credit challenges (04:20) Silicon Valley bank's role in the startup ecosystem (12:26) From SVB to Andreessen Horowitz (18:50) Sponsors: Notion | Puzzle (20:13) Bridging the knowledge gap for first-time founders (22:48) Joining Brex during a time of change (28:02) Starting at Brex: Initial goals and challenges (28:52) Evolving role and team growth (29:39) Bespoke go-to-market strategies (32:08) Defining startups at Brex (36:54) Importance of accounting for startups (42:25) Introducing one-click accounting (46:52) Partnerships and future vision (55:13) Wrap
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3 days ago
56 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E56: 5,000 Startups Later: Tax Lessons Every Founder Needs with Joe Faris
In this episode, Sasha Orloff talks with Joe Faris, founder of Accountalent, about his four decades of helping over 5,000 startups navigate tax and accounting challenges, covering critical founder lessons from 83B elections and R&D tax credits to payroll compliance and bookkeeping best practices that can save startups from costly mistakes and penalties. -- 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/farisjoe/ https://accountalent.com/ -- X/SOCIAL: @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:55) Intro (01:24) Meet Joe Ferris: Startup tax expert (03:24) Joe's journey: From Shell oil to startups (06:46) Birth of Accountalent (09:14) Navigating the financial crisis (13:32) Adventures in IPOs and legal battles (19:33) Sponsors: Notion | Puzzle (21:18) Lessons for founders: Payroll pitfalls (23:21) Introduction to payroll medic (23:39) Understanding tax compliance for startups (26:37) Importance of bookkeeping (27:55) Unbook keeper for founders (29:08) Setting up and managing bookkeeping systems (35:44) Role of RD tax credits (38:32) Lessons learned from working with startups (39:51) Impact of good accounting and tax strategy (42:29) Wrap
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1 week ago
43 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E55: First Round and YC-Backed Startup 'Eliminating Business Bullshit' | Josh Wymer, CEO of CentralHQ
In this episode, Sasha Orloff talks with Josh Wymer, Co-founder and CEO of Central HQ, about raising $8.6 million from First Round Capital and Y Combinator to build an AI-first back office solution that eliminates business compliance tasks through Slack-based automation, helping startups handle payroll, taxes, and HR without the administrative burden that typically comes with traditional software. -- 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/joshwymer/ https://centralhq.com/ -- X/SOCIAL: @jbwyme (Josh) @CentralHQX (Central HQ) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (01:03) Intro (01:46) The unavoidable hassles (02:20) Meet Josh Wymer: The mission to eliminate business BS (02:57) Complexity of payroll and compliance (04:48) Central’s vision: Simplifying the back office (07:19) Challenges and innovations in payroll solutions (10:10) Sponsors: Notion | Puzzle (11:35) Future of AI in business operations (18:42) Power of LLMs and AI in streamlining tasks (21:42) Origin of the tagline (23:41) Investor reactions and brand strategy (24:36) Challenges in a competitive market (25:32) Focusing on founders and SMBs (28:51) Learning and iterating as a startup (33:21) Misunderstandings and common mistakes (36:44) Future of startups and SMBs (38:42) Wrap
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3 weeks ago
39 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E54: Filling the Gap Between QuickBooks and NetSuite with SoftLedger CEO Ben Taylor
In this episode, Sasha Orloff talks with Ben Taylor, CEO & Co-founder of SoftLedger, about bootstrapping a modern, API-first general ledger that helps finance teams manage multi-entity businesses beyond QuickBooks without the complexity of Netsuite. -- 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/bentaylor8/ ⁠https://softledger.com -- X/SOCIAL: @SoftLedger (SoftLedger) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:40) Intro (01:09) Meet Ben Taylor, CEO & Co-founder of SoftLedger (02:36) Origin story of SoftLedger (03:11) Target market and unique selling points (07:14) Evolution of the accounting software market (08:21) AI in accounting: Opportunities and challenges (11:08) Sponsors: Notion | Puzzle (12:31) SoftLedger's approach to AI integration (17:34) Choosing the right accounting software for complex enterprises (19:16) Customer success stories: Eco G energy (22:31) Challenges and surprises in building accounting software (26:58) Importance of multi-entity consolidation (31:53) Fundraising journey and efficient growth (34:16) Future plans and market expansion (37:03) Wrap
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1 month ago
38 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E53: How AI Agents are Replacing Manual Accounting Work with Truewind CEO Alex Lee
In this episode, Sasha Orloff and Alex Lee, Co-founder & CEO of Truewind, to discuss how his company is transforming accounting with AI-powered automation—streamlining tasks like data reconciliation and deposit matching from hours to minutes. They explore Truewind’s journey, recent funding led by Thomson Reuters and Row Capital, and the future of accounting through AI, autonomous agents, and customer-centric innovation. -- 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/alexlee611/ https://www.truewind.ai/ -- X/SOCIAL: @AlexLee611 (Alex) @truewindai (Truewind) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:28) Intro (01:07) Guest Introduction: Alex Lee from Truewind (02:27) Origin of Truewind (06:18) Impact of AI on accounting (08:24) Adoption of AI in accounting (09:59) Future of finance and accounting teams (12:09) Truewind's approach and strategy (15:13) Role of automation in accounting (17:12) Sponsors: Notion | Puzzle (18:49) Digital staff accountant concept (19:53) Exploring AI features in finance (21:07) Government regulations and data sharing (22:23) Exciting news: Fundraising success (24:08) Customer-centric approach to product development (24:57) Advice for founders on fundraising (27:15) Defining success for Truewind (35:55) Future of finance and AI integration (37:08) Wrap
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1 month ago
37 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E52: Building a Viral Contract Platform: Will Hubbard, CEO of Agree
This week, Sasha Orloff sits down with Will Hubbard, Founder & COO of Agree, about building an all-in-one platform that streamlines contracting, invoicing, billing, and payments. They explore Agree’s rapid growth, recent $7.2M seed round, and how AI and user-centered design are shaping the future of finance tech. -- 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/wbhub/ https://agree.com/ -- X/SOCIAL: @wbhub (Will) @AgreeHQ (Agree) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:41) Intro (01:23) Meet Will Hubbard: The story behind Agree (02:19) Agree: All-in-one contracting and invoicing platform (02:54) Evolution of Agree: From venture fund to B2B payments (03:54) Delightful user experience of Agree (06:06) Importance of design in accounting software (06:57) The Why Now: Bundling contracting and invoicing (08:51) Innovative features and AI-driven development (13:38) Sponsors: Notion | Puzzle (15:03) Favorite features: Tracking and reminders (17:34) Surprising use cases and rapid development (20:03) Viral growth of Agree.com (21:22) Story behind Agree.com (23:25) Challenges in naming a company (24:57) Raising the next round of funding (27:26) Future plans and product development (29:11) Advice for finance leaders and founders (34:22) Future of finance: Humans plus software (35:37) Wrap
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2 months ago
38 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E51: Ramp for Revenue: The Tabs Playbook for Faster Cash Flow with CEO Ali Hussain
In this episode, Sasha Orloff talks with Ali Hussain, CEO of Tabs, discuss how the company is using AI to modernize revenue and collections management, reduce DSO, and boost efficiency for finance teams. They discuss Ali’s journey from PhD dropout to fintech founder, Tabs’ $25M raise, and how the platform is reshaping B2B finance operations. -- 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/ali-hussain786 https://tabs.inc/ -- X/SOCIAL: @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (01:04) Intro (01:43) Meet Ali Hussain (03:20) Vision behind Tabs (07:41) Challenges and opportunities in finance automation (11:06) Future of finance teams (15:29) Sponsors: Notion | Puzzle (16:53) Case study: Success with Statik (19:09) Example of Tabs in action (19:49) Future of AI in finance (21:41) Agentic future and trust (23:52) Building operational software (27:32) Favorite features and lessons learned (30:32) Venture capital and market opportunity (34:05) Advice for founders (36:58) Future plans and excitement (41:41) Wrap
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2 months ago
44 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E50: Zuora CFO Todd McElhatton on Why 70% of Finance Stacks Hold Back Growth
This week, Sasha Orloff and Zuora CFO Todd McElhatton discuss the growing complexity of finance operations and the critical role of AI in modern accounting. They talk about the insights from the 'Modern Finance Leader' report, strategies for overcoming legacy systems, and practical advice for finance leaders navigating technological change. -- 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/todd-mcelhatton-2140761/ https://www.zuora.com/resource/modern-finance-leader-report/_ -- X/SOCIAL: @Zuora (Zuora) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:43) Intro (01:11) Season 2 focus: Accounting and technology (01:30) Insights from the Modern Finance Leader Report (02:13) Interview with Todd McElhatton: Challenges in finance technology (05:34) The modernization Catch 22 (09:08) AI and the future of finance (13:46) Sponsors: Notion | Puzzle (15:26) Practical advice for finance leaders (16:53) Zuora's impact and client success (19:20) Role of AI and automation (21:13) Building a 'Yes' department (23:27) Advice for new finance leaders (25:46) Transforming existing finance teams (30:14) Strategic investment in technology (32:22) Evolving role of CFOs (34:21) Joining Zuora and making an impact (35:29) Client success and product value (36:39) Wrap
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2 months ago
39 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E49: Why Accel Backed Campfire to Build the Modern GL, with John Glasgow, CEO
In this episode, Sasha Orloff talks with John Glasgow, CEO & CFO of Campfire, about building an AI-native ERP system that streamlines finance workflows through automation and faster month-end close. Fresh from raising $35 million, John shares insights on modernizing legacy systems, the challenges of building complex financial software, and why now is the right time to innovate in accounting tech. -- 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/johnglasgow https://campfire.ai/ -- X/SOCIAL: @john__glasgow (John) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (00:22) Intro (01:00) Guest introduction: John Glasgow (01:51) Journey of Campfire (05:05) Challenges and innovations in accounting software (06:47) Shift to modern GL and AI integration (11:21) Sponsors: Notion | Puzzle (13:29) Real-world impact and case studies (19:11) Fundraising and future plans (20:01) Partnering with John Lockett and Excel (21:06) AI conference and bigger investments (21:48) Challenges of a seed-backed business (22:50) Advice for founders in big industries (23:36) Product velocity and customer trust (25:51) Future plans and milestones (29:24) Origin of Campfire (30:53) Message to finance leaders and founders (34:05) Future of finance and AI (36:13) Wrap
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2 months ago
39 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E48: Why Sequoia Invested $25M in Accounting Software with Rillet CEO Nicolas Kopp
This week, Sasha Orloff and Nicolas Kopp, CEO & Founder at Rillet, discuss how Rillet is transforming accounting by leveraging AI to streamline processes, improve efficiency, and build lean finance teams. They also talk about the company’s $25 million funding from Sequoia, the importance of clean data, and Rillet’s customer-focused approach. -- 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/nicolas-kopp/ https://www.rillet.com/ -- X/SOCIAL: @nicckopp (Nicolas) @sashaorloff (Sasha) -- TIMESTAMPS: (00:00) Preview (01:00) Intro (01:28) Meet Nicolas Kopp from Rillet (02:23) Rillet's mission and market (03:11) Founding story and challenges (05:27) Building a modern GL (11:27) Future of finance teams (14:56) Real-world examples and success stories (16:39) Sponsors: Notion | Puzzle (18:03) AI-powered ERP (21:28) Building a business with substance (22:03) Investor perception and challenges (22:46) Customer obsession and success (24:31) Advice for founders (27:49) The Sequoia effect (30:47) Future milestones and product vision (32:23) Customer feedback and obsession (38:47) Wrap
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2 months ago
42 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E47: Agentic Commerce, Stablecoins, and Global Trends with Cindy Turner, CPO of Worldpay
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
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3 months ago
42 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
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 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
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4 months ago
53 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E45: 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 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
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5 months ago
35 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E44: 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 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
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5 months ago
39 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E43: 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 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
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5 months ago
44 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E42: 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 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
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5 months ago
41 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E41: 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 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
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5 months ago
40 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E40: 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, 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
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6 months ago
45 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E39: 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 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
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6 months ago
35 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
E38: 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 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
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6 months ago
36 minutes

"Tech Finance" with Sasha Orloff: B2B Fintech | AI | Finance Tech
On Tech Finance, host Sasha Orloff brings you inside the office of the CFO - covering major tech finance news including funding announcements, deals, product launches, and emerging players shaping B2B fintech. We break down the week's biggest developments in finance tech and accounting, and explore how finance leaders are putting AI to work. Tech Finance is brought to you by Puzzle, the modern accounting platform with an AI-first ledger, built for speed, automation, and real time decision making. Learn more: puzzle.io Tech Finance is part of the Turpentine podcast network. Learn more: turpentine.co