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

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

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

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

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

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

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

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

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