Podcast appearances and mentions of sasha orloff

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

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

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

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

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

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

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

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

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

Accounting is no longer just about tracking numbers. It's about delivering real financial insights, making better decisions, and shaping the future of businesses.For Sasha Orloff, CEO and Co-Founder of Puzzle, that future is AI-native. After years of working in fintech and scaling financial services, he saw firsthand how accounting could be transformed—not by replacing accountants, but by elevating their role. By integrating AI at the core of bookkeeping, Puzzle is redefining how firms approach accuracy, efficiency, and advisory work.In this episode, Sasha breaks down what it truly means to be AI-native, why trust and traceability matter more than ever, and how accounting firms can shift from manual work to high-value strategy. If you're in the accounting world and wondering how AI will shape your future, this conversation is a must-listen.In this episode, you'll learn:The difference between AI-native and AI add-ons: Why layering AI on top of legacy systems isn't enoughWhy traceability is key to AI adoption: How accountants can maintain accuracy and confidence in automationHow accounting firms can scale without burnout: Why AI should free up time for strategy, not just speed up processesJump into the conversation:(00:00) Meet Sasha Orloff(02:06) Sasha Orloff's unexpected path to loving accounting(05:07) Bringing big-company financial insights to small businesses(07:15) Why AI is transforming accounting in 2025 and beyond(09:23) AI isn't replacing accountants—it's making them more valuable(12:00) AI-native vs. AI add-ons: What's the real difference?(16:13) AI mistakes are inevitable—why traceability is the solution(19:30) The risks of using too many disconnected tools(22:15) Why AI will never be 100% accurate—and that's okay(26:20) The biggest mistake firms make when adopting AI solutions(31:36) Why QuickBooks' incentives don't align with accounting firms(38:00) Scaling bookkeeping revenue without adding more work hours(45:00) What the AI-powered accounting firm of 2030 looks like(50:00) How to automate without losing control of accounting decisions(53:32) Why accountants must lead AI adoption—not fear it(55:28) Matt's takeaways

In this first episode of Season 2, Sasha Orloff is joined by Matt Tait, CEO of Decimal, to discuss the rise of AI in accounting, Decimal's recent acquisition of KPMG Spark, and their new strategic partnership with Puzzle. Matt also covers his journey building Decimal, the balance of human expertise in a tech-driven world, and the industry's future. --

In the final episode of season one, Sasha Orloff is joined by David Hartley, a seasoned CPA with over 30 years of experience, as they explore the evolution of accounting from the 15th century to today's AI-driven landscape and discuss how the profession adapts to technological change while preserving its core value of trust. —

In this episode, Sasha Orloff is joined by Andrew Gazdecki, founder of Acquire.com, who shares his expertise on successfully selling companies, maximizing exit value, and key lessons from his own acquisition experiences, with over $500 million in closed deals. —

This week, Sasha Orloff sits down with JustPaid founders Daniel Kivatinos, a successful YC founder behind the first iPad medical records company, and Anelya Grant, a Kazakhstan immigrant who built an accounting practice for YC startups, about how their unique backgrounds inspired them to tackle the critical challenge of accounts receivable automation with an AI-powered platform. For full show notes, visit: https://highlightai.com/share/309bb91f-34ee-4052-88e5-28718a9101da —

Today, we're sharing a special episode from our friends at the Webby Awards-honored CRAFTED. podcast. In this conversation, Dan Blumberg interviews growth expert, SYSTM founder, and former PayPal leader Matt Lerner about his book 'Growth Levers,' offering actionable strategies for startups to identify the 10% of efforts that drive 90% of growth. They discuss common startup pitfalls, the mindset shift to customer-centric thinking, JTBD-style interviewing, and the importance of rapid experimentation. For full show notes, visit: https://highlightai.com/share/af10e152-f30a-403e-805f-d234eb40109a — Check out Dan Blumberg's CRAFTED. where he interviews founders of high growth startups, including from Lattice, Gusto, Moov, Monte Carlo, Customer.io and our own Sasha Orloff! Apple: https://podcasts.apple.com/us/podcast/crafted-the-tech-podcast-for-founders-makers/id1649355311 Spotify: https://open.spotify.com/show/3xtU2V1jRP89aI1ULRN2GI?si=b5753bd5be14494c — SPONSOR:

Help improve CRAFTED. Please take this quick 5m survey. You might win a prize. Thanks!Accounting may not be the sexiest part of running a business, but according to Sasha Orloff, it's the key to understanding your company's financial health—and ultimately, its success. At his previous two startups, Sasha was frustrated that he didn't have a real-time view into his company's financial health. And he realized the problem wasn't accounting – but accounting software. So, Sasha founded Puzzle, because “it's hard to set yourself up for success if you don't know when you're about to run out of money.” Sasha is on a mission to make accounting intuitive, real-time, and accessible for founders and finance teams alike. In this episode of CRAFTED., we explore how Sasha is crafting Puzzle, how AI makes this the right moment to challenge QuickBooks, and why he was so confident that the market needed Puzzle that he was undaunted by the five years he estimated it would take to build an MVP. "We're not just rethinking accounting software—we're rethinking how founders and CEOs can make data-driven decisions to build enduring companies." Sasha shares:How the frustration he felt at his previous startups led him to Puzzle Why “accounting gets a bad rap”, but it crucial for founders: it's your financial healthWhy second-time founders are ideal customersWhy it took five years to build an MVP – and why he wasn't daunted by this expectationWhy the problem was never accounting, but accounting software and the distorted realities it's built to createWhy AI and modern API's made now the right time to build PuzzleWhy Puzzle is “poking the bear” and putting highway billboards up near QuickBooks HQ(01:04) - Sasha's finance frustrations at previous startups (02:49) - Traditional accounting software isn't made for founders (02:49) - The problem with traditional accounting software (05:35) - What Puzzle does differently: Real-time financial health (08:26) - AI's role in revolutionizing accounting (10:56) - Why second-time founders are Puzzle's ideal users (13:22) - Building a five-year MVP: Challenges and conviction (17:15) - Tackling QuickBooks: Bold marketing moves and billboards (19:49) - Understanding edge cases and complexity in accounting (23:41) - The future of Puzzle: Helping startups thrive (27:35) - Hosting the Turpentine Finance podcast Links:Learn more about Puzzle: Puzzle.ioFollow Sasha Orloff on LinkedIn: Sasha OrloffTurpentine Finance Podcast: Turpentine FinanceCRAFTED. is produced by Modern Product Minds, where CRAFTED. host Dan Blumberg and team can help you take a new product from zero to one... and beyond. We specialize in early stage product discovery, growth, and experimentation. Learn more at modernproductminds.com Subscribe to CRAFTED., follow the show, and sign up for the newsletter

This week, Sasha Orloff is joined by Andrés Ugarte to explore the rise of Copilot Money after Mint's shutdown announcement, sharing his journey from frustrated user to founder of a privacy-focused personal finance app, and discussing the challenges of building a product-driven company in a shifting financial landscape. For full show notes, visit: https://highlightai.com/share/31895f5b-d783-4eaa-ab11-ac3214b21ddb — RECOMMENDED PODCAST: Unpack Pricing Dive into the dark arts of SaaS pricing with Metronome CEO Scott Woody and tech leaders. Learn how strategic pricing drives explosive revenue growth in today's biggest companies like Snowflake, Cockroach Labs, Dropbox and more. Apple: https://podcasts.apple.com/us/podcast/id1765716600 Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg — SPONSOR:

In this episode of Turpentine Finance, host Sasha Orloff sits down with Paul Barnhurst, a passionate FP&A educator and content creator who shares insights on financial planning & analysis, teaching methodologies, and the evolution of financial tools. For full show notes, visit: https://highlightai.com/share/1823b417-abe8-49bb-8f00-d673e24077b1 --

In this episode, host Sasha Orloff interviews Brad Wiskirchen about his journey with Kount, the AI-driven fraud prevention company he bootstrapped and sold to Equifax for $640 million, while sharing insights from his experience as a founder and now a partner at CVC Capital Partners. For full show notes, visit: https://highlightai.com/share/eec1be56-ae04-4afc-bb24-7ed8523b2176 --

In this episode, Sasha Orloff is joined by Aneal Vallurupalli, CFO at Airbase, who drops insights on modern spend management and his journey from M&A to leading finance at a Paylocity acquisition target. Aneal discusses his career trajectory, the impactful role of a CFO in spend management, and how Airbase revolutionizes non-payroll spends in the AI era. Aneal also offers essential advice to CFOs navigating today's dynamic financial landscape.

In this episode, Sasha Orloff sits down with Blake Hutchison, CEO of Flippa, the leading platform for buying and selling online businesses. Blake shares insights from his career (Xero, Lonely Planet, Good44), and explains how Flippa operates as the ‘investment bank for the 99%,' providing a marketplace for subscale business transactions. The episode dives into the opportunities presented by the marketplace, key deal characteristics, and the different buyer segments. They also discuss the importance of financial literacy for subscale businesses, provide tips for first-time buyers, and offer predictions for the future of flipping businesses.

In this episode, Sasha Orloff welcomes Jane Lee and Aditya Reddy of Sapphire Ventures to unpack their paper, “Rise of the Next Gen CFO,” which features a market map of CFO tools and identifies key trends and predictions. Jane and Aditya discuss how finance roles are transforming, the convergence of finance and data science, the influence of AI, and emerging investment strategies in this fast-paced sector. Nothing presented within this podcast is intended to constitute investment advice, and under no circumstances should any information provided herein be used or considered as an offer to sell or a solicitation of an offer to buy an interest in any investment fund managed by Sapphire Ventures (“Sapphire”). Information provided reflects Sapphires' views as of a time, whereby such views are subject to change at any point and Sapphire shall not be obligated to provide notice of any change. No assumptions should be made that investments or strategies described were or will be profitable. Due to various risks and uncertainties, actual events, results or the actual experience may differ materially from those reflected or contemplated in these statements. Nothing contained in this podcast may be relied upon as a guarantee or assurance as to the future success of any particular company or strategy. Past performance is not indicative of future results. -- SPONSORS: ANROK is the enterprise-grade solution that automates sales tax compliance worldwide. Anrok tracks your exposure, calculates tax, and handles filings—all in one platform. Visit https://www.anrok.com/turpentine to claim your free nexus study and take control of your SaaS tax strategy. NETSUITE: More than 40,000 businesses have already upgraded to NetSuite by Oracle, the #1 cloud ERP bringing accounting, financial management, inventory, HR, into ONE proven platform. Download the CFO's guide to AI and Machine Learning at https://netsuite.com/102 METAVIEW is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/heretics OMNEKY is an omnichannel creative generation platform that lets you launch hundreds of thousands of ad iterations that actually work customized across all platforms, with a click of a button. Omneky combines generative AI and real-time advertising data. Mention "Cog Rev" for 10% off https://www.omneky.com/ -- LINKS: Rise of the Next Gen CFO: https://sapphireventures.com/blog/rise-of-the-next-gen-cfo-the-evolution-of-finances-role-and-tech-stack/ Sapphire Ventures: https://sapphireventures.com/ -- X/SOCIAL: @sashaorloff @leejane09 @adityareddy97 -- TIMESTAMPS: (00:00) Preview (00:53) Intro (01:18) Viral market map by Sapphire Ventures (02:23) Rise of the Next Gen CFO (06:25) Key findings from the paper (10:57) Impact of AI on finance (18:09) Sponsors: Anrok | Netsuite (20:36) Complexities with crypto assets (24:22) AI affecting different industries (28:22) Investment insights from Sapphire Ventures (34:58) Sponsors: Metaview | Omneky (36:27) Platform risks (41:06) Sapphire Ventures' focus (43:37) Wrap

In this episode, Sasha Orloff is joined by Eugene Spevakov, the Treasurer and Head of Corporate FP&A at 6sense, treasury expert, and veteran CFO. Sasha and Eugene dive deep into the Treasury function: how it differs across industries, how a scaling startup will know when it's time to hire for the role, how to structure the function, and what separates a great treasurer from merely good. Eugene offers a masterclass on leveraging treasury to drive growth, improve cash flow, and allocate risk strategically in an uncertain world.

In this episode, Sasha Orloff sits down with Camille Ricketts, former Co-Head of Marketing at Notion, Editor of First Round Review and Elon's comms manager at Tesla, to talk about the ROI of content as a growth driver. Camille, currently a partner at XYZ Venture Capital, played a key role in persuading Sasha years ago to invest in content as a revenue channel. In this episode she shares her invaluable insights from her roles at Notion, Tesla, and First Round Review. Tune in to hear Camille's compelling arguments for CEOs and VPs about the strategic value of content marketing. This is a must-listen for founders, finance leaders, and anyone eager to leverage content for growth.

In this episode, Sasha Orloff is joined by Chris Sands, Head of Jobs at The F Suite, to discuss the landscape of finance leadership and career advancement in 2024. Sands unpacks the changing role of CFOs and how to navigate compensation from the vantage point of CFOs (and the CEOs hiring for the role). This episode offers invaluable insights on how to stay relevant, adaptable, and ahead of the curve in your finance career.

In this episode, Sasha Orloff is joined by Valerie Burman, CFO of Sugar Bowl Resort in Lake Tahoe and former VP at Workday and SAP, shares her unique journey from being an executive at Silicon Valley tech companies to becoming the CFO of a ski resort. Valerie talks about her philosophy on building the dream team, the importance of understanding business acumen in a CFO role, and strategies for achieving long-term liquidity. She also reflects on hard won lessons from multiple M&As and corpdev. -- Apply to join over 400 Founders and Execs in the Turpentine Network: https://www.turpentinenetwork.co/ -- RECOMMENDED PODCAST:

OpenAI Controller Sowmya Ranganathan sits with Sasha Orloff to share accounting insights from her experience at Square, Rippling, and OpenAI. She discusses automation and using AI in accounting, how difficult software motivated her to make the move to Controller at Rippling, and how she's streamlining the accounting workflow at OpenAI, where she is currently Controller. Sowmya also explains how AI is making accounting easier and why future accounting teams may be small and broadly skilled. --- This show is a part of the Turpentine podcast network. Learn more: https://www.turpentine.co --- SPONSORS: ATTIO

How do you navigate the tide turn when your competitor collapses during one of the biggest banking crises in recent history? In this conversation, Sasha Orloff sits down with Immad Akhund, founder and CEO of Mercury*. Immad pulls back the curtain on the chaos and critical decisions made when Silicon Valley Bank fell. From mobilizing an all-hands effort to rapidly onboard new customers to developing new product features virtually overnight to instill confidence, Immad provides an unvarnished look at crisis management and steadfast leadership during turbulent times. He also shares insights on Mercury's customer-first approach to building, how rising interest rates transformed their business model, and how he thinks about investing in new product initiatives by allocating internal resources like venture investments. *Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust, Members FDIC. --- SPONSOR: Attio is the next generation of CRM. It's powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. Profiled this season: Databricks, Reddit, Twilio, Copart + more. Spotify: https://open.spotify.com/show/0epyYBAxLeF0PsNagdDJAJ Apple: https://podcasts.apple.com/us/podcast/company-breakdowns/id1743119197 --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We're launching new shows every week, and we're looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: https://mercury.com/ --- X/SOCIAL: @sashaorloff (Sasha) @Immad (Immad) --- TIMESTAMPS:

In this conversation, Sasha Orloff sits down with Steve McLaughlin, CEO and Managing Partner of FT Partners. Steve provides an insider's look into the high-stakes world of capital raising and dealmaking for high-growth private companies. From being Goldman Sachs' Former Head of Fintech to founding FT Partners, a global fintech investment firm, McLaughlin shares his strategies for crafting compelling narratives that unlock massive fundraising rounds - like the $33 billion valuation for Revolut and a $100 million plus raise for Sam Altman's Worldcoin. They dive deep into storytelling, the importance of product over marketing spend, founder red flags, and much more. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It's powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We're launching new shows every week, and we're looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: https://ftpartners.com/ X/SOCIAL: @sashaorloff (Sasha) @FTPartners (Steve) TIMESTAMPS: (00:00:00) The art of storytelling in high-growth company valuations (00:01:31) A capital whisperer's journey (00:02:26) Inside FTPartners: Shaping the fintech universe (00:04:33) The intricacies of capital raising and M&A (00:07:39) Crafting the perfect capital raise story (00:14:13) The complex world of investor networks (00:16:41) Maximizing value beyond valuation (00:19:05) A deep dive into successful storytelling and strategic selling (00:22:57) The philosophy of business growth and valuation (00:23:33) Understanding the founder's journey and ambitions (00:24:32) The role of investment bankers in raising capital (00:25:46) The importance of choosing the right banker (00:28:17) Revolut's success story: A case study (00:36:07) Strategic advice on growth vs. profitability (00:39:01) Reflecting on capital raising experiences and red flags (00:41:06) The evolution of FT Partners (00:46:12) Closing thoughts and acknowledgements

TLDR: These show notes were optimized using Claude AI Haiku and are designed to make you listen to the full episode. We even asked Haiku to provide a Haiku summarizing the show notes for your reading pleasure.Haiku:Finance takes new shape,AI-driven transformation,Shaping the future. Prepare to be captivated as hosts Paul Barnhurst and Glenn Hopper welcome Sasha Orloff, CEO of Puzzle, to uncover the technological advancements reshaping the world of finance and accounting. In this eye-opening episode, you'll discover:How generative AI is seamlessly integrating into everyday software, automating tasks and delivering data-driven insights.The rise of "AI agents" in 2024 - advanced systems designed to autonomously process complex problems and provide tailored solutions.Sasha's visionary project, Puzzle, modernizing accounting software with real-time, flexible financial data processing.The transformative potential of blockchain technology to enhance transparency and traceability of financial transactions.The future of finance reimagined through AI and predictive analytics, empowering more precise forecasting and strategic decision-making.Sasha shares his insightful perspective:"I'm building Puzzle, which is modern accounting software for growing companies.""We may not yet be at a point where AI is going to take our jobs, but the future will be divided into two camps: people who use AI and those who don't. One of these groups is going to be left behind."Don't miss this captivating conversation that explores the intersection of finance, technology, and AI. Gain invaluable insights to stay ahead of the curve and thrive in the rapidly evolving world of corporate finance.Follow the Conversation:Glenn Hopper (LinkedIn: https://www.linkedin.com/in/gbhopperiii)Paul Barnhurst (LinkedIn: https://www.linkedin.com/in/thefpandaguy)Sasha Orloff (LinkedIn: https://www.linkedin.com/in/saor/)Puzzle (LinkedIn: https://www.linkedin.com/company/puzzlefin, Website: https://puzzle.io)Future Finance is sponsored by QFlow.ai, the strategic finance platform solving the toughest part of planning and analysis: B2B revenue. Align sales, marketing, and finance, speed up decision-making, and lock in accountability with QFlow.ai. Learn more at Qflow.ai/future-financeIn today's episode:[01:53] Introduction[03:34] The latest phase of AI revolution[04:51] Pros and cons of chatbots and the rise and evolution of AI agents[09:17] Recent updates about AI[13:52] Guest's background[15:30] Insights from guest's career[17:51] Introduction of Puzzle and future of general ledger in accounting[25:12] How blockchain can be an effective tool for accounting[30:24] How AI and predictive analytics can change finance in upcoming years[34:34] Democratization of data science and various uses of machine learning[39:05] Lighting Round Questions!

In the debut episode of Turpentine Finance, host Sasha Orloff sits down with Casey Woo, Founder of Operator's Guild, GP at Fog Ventures, and WeWork's former Global Head of Strategic Finance. They unpack the value of being a business-first CFO, the lessons learned from working in pressure-cooker settings like WeWork, how CEOs can evaluate CFOs (and vice versa), and frameworks for being a career 'specialist generalist'.  This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It's powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We're launching new shows every week, and we're looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: Operator's Guild: https://operators-guild.com/ Fog Ventures: https://www.fog.ventures/ Casey's Linkedin: https://www.linkedin.com/in/caseywoo Casey's contact: hello@operators-guild.com --- X/Twitter @sashaorloff (Sasha) @caseyswoo (Casey) @FogVentures (Fog) @turpentinemedia --- TIMESTAMPS: (00:00) Preview (02:00) Life as a banker (04:06) Story following numbers or numbers following story (04:39)How banking prepared Casey for working in a startup's finance team (07:00) Deciding that working in a startup is a right fit (09:10)Hiring a CFO (11:20) Advice for bankers transitioning to operating roles (12:41) First things to accomplish when stepping into a role (14:05) Sponsor: Attio (14:52) Interview question to see if a founder takes finance seriously (16:16) Advice for CFOs to change the dynamic that finance has in the company (18:08)Casey's time at WeWork as CFO for Western US and Canada (22:00) Casey's experience being Global Head of Strategic Finance at WeWork (29:40 Advice for founders in dealing with different growth or recessive cycles (32:57) Probabilities (34:00) Time spent on fundraising vs supporting the founder as a CFO (35:26) Operator's Guild and Generalists (42:00) How can operators thrive in a transition role (47:28) The number one piece of advice Casey would give to CFOs (49:38) Wrap

Today is a special episode where CJ Gustafson and Sasha Orloff (3x founder and current CEO of Puzzle) go deep on the CFO-CEO mindsets…and talk podcasting. They cover: highlights and memorable advice from CJ's 50+ interviews on this feed, how to have impact as a CFO & CEO, the challenges of building finance software, each host's biggest mistakes, and how to make a successful podcast. Turpentine Finance hosted by Sasha Orloff will debut later this week and this season will feature firsthand stories from guests about the greatest inflection moments in the history of Mercury, OpenAI, Andressen Horowitz, Netflix, Runway, and more.

Lex chats with Sasha Orloff, CEO and Co-founder of Puzzle - “the first smart accounting software,” which combines a streaming financial data platform that's connected to a general accounting ledger. Sasha starts the conversation detailing his journey from traditional banking to fintech entrepreneurship. Reflecting on the early days of fintech, contrasting the East and West Coast perspectives, and sharing his experiences from leading innovative fintech ventures like LendUp. The conversation dives into the future of fintech, discussing the transition into autonomous accounting, the rise and fall of Personal Financial Management (PFM) tools, and the integration of natural language processing into quantitative software. The duo also contemplates the nature of rules in language models, the dichotomy between deterministic and probabilistic models in AI, and the future of intelligent software. The episode concludes with Sasha sharing various channels to connect with him and learn more about Puzzle. MENTIONED IN THE CONVERSATION Puzzle's Website: https://bit.ly/3NKuO6YSasha's LinkedIn profile: https://bit.ly/3Pt3pHX Topics: Fintech, AI, artificial intelligence, machine learning, GenAI, Accounting, Software, LLM, embedded finance Companies: Puzzle, Puzzle Financial, Mission Lane, LendUp, ChatGPT, Brex, Stripe, Plaid ABOUT THE FINTECH BLUEPRINT 

On The Deep End today, we welcome Sasha Orloff, the Founder and CEO of Puzzle, a modern accounting software package for startups that recently raised $15 million in series A. Sasha joins us to discuss the use of accounting as a powerful decision-making tool and the creation of infrastructure to start and scale businesses, as part of our series on meta-problems to help founders start more companies. Despite advances in financial technology, Sasha believes that core accounting software remains outdated and does not take advantage of modern capabilities. He suggests that accounting could be a competitive advantage for businesses if it were reimagined as a tool for data-driven decision-making, empowering founders to build better businesses. During the episode, Sasha identifies three key areas that founders should focus on when fundraising: telling a compelling story, taking the process seriously, and planning for success: Founders must have a strong answer for what sets them apart from their competitors, and they should be intentional about raising venture capital. As the market returns to normal, Sasha advises founders to be aware of business compliance and financial diligence to avoid giving away a larger percentage of their company for less money. Throughout the episode, he emphasizes the importance of founders understanding their business numbers to make informed decisions and build successful companies. You can learn more about Puzzle at https://puzzle.io.

Sasha Orloff built his first two companies at the same time. Now he's helping other founders figure out the financial puzzle they face on the startup journey. His latest venture, Mission Lane, has raised funding from top-tier investors like Oaktree Capital Management, Gramercy Ventures, QED Investors, and Goldman Sachs.

Connect with Fintech One-on-One: Tweet me @PeterRenton Connect with me on LinkedIn Find previous Fintech One-on-One episodes

It is curious to me that 56% of the adults in this country are classified as subprime. Yet, most lenders are focused on prime or near prime consumers. Improving the financial health of the subprime population is clearly a bigger problem but also one that can potentially have a bigger reward. Our next guest on […] The post Podcast 162: Sasha Orloff of LendUp appeared first on Lend Academy.

It is curious to me that 56% of the adults in this country are classified as subprime. Yet, most lenders are focused on prime or near prime consumers. Improving the financial health of the subprime population is clearly a bigger problem but also one that can potentially have a bigger reward. Our next guest on […] The post Podcast 162: Sasha Orloff of LendUp appeared first on Lend Academy.

Today’s show brings us two fascinating guests.  Alex Lintner is President of Consumer Information Services for Experian, and Sasha Orloff -- who is a previous guest on Barefoot Innovation -- is founder and CEO of LendUp. They recently joined forces to explore using new kinds of data to widen financial inclusion. We all sat down to discuss it at the LendIt conference this spring in San Francisco. Credit scores are a great tool for evaluating the creditworthiness of many consumers, but as Alex explains, not for all of them. He and Sasha think -- as do I -- that we need a fuller view into what Alex calls the consumer’s financial “reputation.” Experian estimates that 100 million people in America need this kind of broadened evaluation. We know that many consumers with low or no credit scores are actually creditworthy, and in fact could prove it if we had systems that could look closely at their financial behaviors and situations beyond reported credit history. Traditionally, though, we didn’t have efficient ways to get that information because, in the analog age, when the current systems were designed, data was scarce and costly. Today, in contrast, we have massive volumes of digital information we can access and analyze, instantly and efficiently. This creates the ability to do what used to be impossible -- make financial services more inclusive, without sacrificing lending soundness. Toward that goal, LendUp and Experian undertook a joint research project to look at the benefits of capturing data on customers’ performance on single-payment loans. The study produced really striking results -- the overwhelming majority of consumers in the study came out with positive impacts on their credit scores. And as Alex explains, single-payment loans are just one kind of nontraditional data. In today’s digitized world, there are many other factors that we can begin to capture methodically and build into routine credit scores. Experian is now routinely doing this, offering a new score called Clear Early Risk. In our conversation, Alex and Sasha share insights drawn from their own lives and talk about the many situations in which people have trouble accessing credit when they need it. Some of these consumers are young people or new immigrants with thin or no credit file. Some are facing life changes like a family death or divorce. Some are contending with emergencies like loss of a job or medical bills. Our discussion also tied these kinds of individual challenges into big shifts underway overall in lifestyle and in technology -- the advent of mobile financial services, the rise of the gig economy, and expanding use of artificial intelligence.  In addition, we touched on the future of the Community Reinvestment Act, which is due for much-needed, tech-driven modernization. Using alternative credit risk data has complex implications for fair lending regulation, especially in the US and especially regarding “disparate impact.”  US policy bars use of credit practices that have a disproportionate adverse effect on “protected classes” like women and minorities, unless the lender can demonstrate a business need and show that less-discriminatory alternatives are not available. The criteria for proving this are not clear today, and I’m among the many people who think that clarifying them is essential to expanding financial inclusion by fostering use of new data. Despite having the best of intentions, policymakers have inadvertently made hard-to-score consumers the riskiest market to serve, due to the regulatory risk arising from uncertainty. That chills efforts to address these customers’ needs by many mainstream and high-quality lenders. The CFPB is exploring this issue through its evaluation of alternative data and issuance of a “no action letter” for Upstart. A similar effort is underway, also, at the new nonprofit FinRegLab, which is run by Melissa Koide and funded by the Omidyar Network. I chair FinRegLab’s board, and we’re conducting empirical testing of alternative data -- specifically cash flow underwriting -- including how these new methods relate to disparate impact. Today’s show is a glimpse of a promising future, harnessing innovative technology to produce lending that is more inclusive, and also more sound. More Links Episode Transcription Podcast with Al Ko - Episode recorded last year with Al Ko of Intuit LendUp Infograph Alternative Credit Data trends and reports Op-Ed by Sasha on innovation in credit scoring More on Sasha and Alex Sasha Orloff is CEO and co-founder of LendUp. LendUp’s mission is to provide anyone with a path to better financial health. The company builds technology, credit products, and educational experiences that haven’t existed before for the emerging middle class -- the 56% of Americans shut out of mainstream banking due to poor credit or income volatility. It has originated more than $1 billion in loans. With offices in San Francisco, CA and Richmond, VA, LendUp is backed by debt and equity financing from venture and social impact investors including Y-Combinator, Kleiner Perkins, Andreessen Horowitz, Google Ventures, Victory Park Capital and Yuri Milner’s Startfund. In June, both Nigel Morris and Frank Rotman of QED Investors joined the LendUp board of directors. Prior to founding LendUp, Sasha held roles in risk management, finance, online acquisitions and customer insights on Citi’s consumer credit team, and most recently served as Senior Vice President on Citigroup's Venture Capital team. He previously worked for the Grameen Foundation Technology Center and The World Bank. He has a B.S. in applied math and economics from the University of California, San Diego and an MBA from Georgetown University. Alex Lintner is President of Experian’s Consumer Information Services, overseeing the company’s US consumer credit bureau and the National Consumer Assistance Centre (NCAC). He’s responsible for all aspects of Experian’s consumer credit activities within the business-to-business marketplace, including delivery and management of value-added credit risk, marketing, and collection products to help clients manage and optimize their customer relationships. Alex was previously CEO and President of Vertafore, a $450+ million revenue insurance industry technology provider. Prior to that he was President of Intuit’s Global Business Division and also Senior Vice President of Strategy, Government Affairs and Corporate Development. He’s also spent 15 years as a consultant, starting as a Business Analyst at Dr. Hoefner & Partners in Munich, Germany and later serving as Vice President of The Boston Consulting Group in their London and San Francisco offices. More for our listeners Our next guest on the show will be another community bank CEO, Mike Butler of Radius Bank in Boston.  Upcoming episodes include a fascinating conversation with Congressman Gregory Meeks on financial innovation and policy; a talk I recorded this year at LendIt with my friend Greg Kidd of Global ID; and three discussions with regtech firms -- JWG in London, Compliance.ai, and Alloy. Speaking of LendIt, I was a guest this month on Peter Renton’s Lend Academy podcast, and he’ll be on our show soon as well. I was also a guest in June on the Commodity Futures Trading Corporation podcast, CFTC Talks, with Andy Busch. And here are my two podcasts with the CFTC, one with Chairman Giancarlo and a recent one with innovation head Dan Gorfine. It’s not too early to register for the fall’s premier fintech event, Money 2020, in October in Las Vegas. I’ll again be MC for the regulatory track, which, remember, is on Sunday -- be sure to plan accordingly!  I’ll also be speaking on the Revolution Stage, which is new this year, about regulation innovation. Also watch for Regtech Rising in December, which I’m helping to plan. We’ll also be posting information on my collaboration with Brett King on his new book on the future of finance -- we’ll have a show and events on that as well, and I’ll be a guest on Brett’s great radio show Breaking Banks this week, on July 5. Please remember to give Barefoot Innovation a five-star rating on iTunes to help us expand the show. I hope you’ll sign up to get emails that bring you the newest podcast, newsletter, and blog posts, at www.jsbarefoot.com.  Follow me on Twitter and our Facebook fan page. And please send in your “buck a show” to keep Barefoot Innovation going! SUPPORT OUR PODCAST Until next time, keep innovating! Subscribe Sign up with your email address to receive news and updates. Email Address Sign Up We respect your privacy. Thank you!

Today’s episode is about new ideas about a very old problem in consumer finance -- high-cost lending to high-risk borrowers. My guest is LendUp CEO Sasha Orloff, who is one of a new generation of fintech founders building alternatives to traditional payday lending. In public policy, there has been a long-standing assumption, sometimes implicit and sometimes explicit, that widespread access to credit -- especially mortgages -- is a good thing. A host of government regulations, programs, and bank supervisory activities aim to promote more credit, because we’ve assumed that wider credit access is, broadly speaking, good. Is it, though? Most people would agree that up to a point, it’s good, and beyond some point, it becomes bad. It definitely becomes bad at the point where the borrower can’t realistically repay the loan. It can also become bad if the pricing is so high that the person ends up worse off for borrowing, instead of better, especially if the borrower doesn’t understand the terms We could do many episodes on the tough issues embedded in this question. One is whether it’s better to have high-cost loan options that are legal and subject to regulation, or to outlaw them, knowing that shutting down legal options will drive some desperate people to use illegal ones, which hurt them even more. Another is the philosophical question of how much the government should protect people from themselves. If the price of a high-cost loan is clear, and borrowers understand it, should the government respect their decision on whether to take it, or substitute its judgment for theirs and remove the option? Again, public policy has been debating these issues for decades --  maybe centuries -- and still is, including through many of the initiatives taken to date by the CFPB. In this podcast, we won’t tackle those questions, but will instead ask a very different one: What if we didn’t need to resolve them? What if, thanks to technology, we could solve the problems surrounding high-cost credit -- or a big chunk of them -- not through regulation, but in the marketplace. LendUp.  Sasha Orloff founded LendUp to provide more affordable credit to the 50% of Americans with credit scores below 680. He had worked at a big bank, and at an NGO in the developing world, and had a brother in the technology world who kept telling him that better software could create better products. He finally founded LendUp, to build them. LendUp offers credit products online -- which means it has, automatically, a lower cost structure than the traditional bank model of branches. As Sasha explains in our discussion, it has also designed its products to offer borrowers a gateway to better credit scores, credit options, and financial health. LendUp is backed by major investors including Y-Combinator, Google Ventures, QED Investors, Startfund, Kleiner Perkins, A16Z seed fund, Thomvest Ventures, Kapor Capital, Bronze Investments, Founders Co-Op, Data Collective, Susa Ventures, and Radicle Impact. Sasha and the firm have been featured in the Wall Street Journal, NYTimes, Financial Times, CNN, NBC, TechCrunch, Venturebeat, Inc, Wired, Bloomberg, Fortune, Dow Jones, American Banker, Marketplace and many others. He has presented at TEDx, and LendUp, and they won Finovate Best In Show. FastCompany named the firm as one of the World’s Top 10 Most Innovative Companies in Personal Finance, and it won runner up in Webbys for best website design. They have presented at LendIt, Emerge, Money20/20, The HubSF, NBC News, and Huffington Post Live, and participate in The Clinton Global Initiative on Financial Inclusion. Sasha also serves on the Consumer Lending Advisory Board for TransUnion (one of the three major credit bureaus) A regulatory note.  After Sasha and I recorded this episode, the CFPB announced an enforcement action against LendUp. The order is, among other things, a warning flag for startups about the importance, and the great challenges, of maintaining complete regulatory compliance in the midst of rapid growth. The company has responded with a massive expansion of compliance staff. Following the announcement of consent order last fall, it issued this statement: We started LendUp because the traditional banking system wasn’t working for more than half of Americans. From day one, we’ve committed ourselves to offering better, safer and more transparent credit products and to aligning the success of our business with the success of our customers. We genuinely believed the product features that were identified by the CFPB and the California DBO– like optional expedited funding and a 30 cent per day discount for early repayment—were in the best interests of our customers. But we fell short in the execution and in meeting the expectations of our regulators.  We have since taken action to resolve every issue they’ve raised, including beginning to refund customers prior to entry of the Consent Order and Settlement Agreement. We’ve also made significant investments to build out our legal and compliance operations. In this respect, we are a different company today, with a completely new legal and compliance team that is larger now than our entire company when we started these exams. Importantly, those teams are brought in at the beginning of the development lifecycle for every new product and feature. We are proud of the progress we’ve made to expand access to credit, lower borrowing costs and provide credit-building opportunities to our customers. LendUp has: Graduated more than 20,000 borrowers to the highest rungs of the LendUp Ladder in more than 11 states Saved Californians alone more than $18M in 2016 (and an estimated $40M to date nationwide) Delivered over 800,000 free credit education classes; and Helped LendUp customers improve their credit scores: according to TransUnion data, 66% of LendUp customers showed a credit score increase – more than those in the control group using similar types of products from other lenders. We are eager to keep building on this track record, and look forward to continuing our work to put our customers on paths to better financial health. I have found Sasha to be one of the most thoughtful people in fintech. I think you’ll be fascinated by his overview of the shrinking of the American middle class, the impact of the smartphone revolution; innovation models fort startups versus banks; how making financial education interesting; and how to redesign regulation for the 21st century, The loans at Lendup cost less than traditional payday options, but more than loans to prime customers, because the borrowers are simply higher risk. If lenders can’t charge enough to cover that risk, they won’t serve these customers. If they can, though, and if they can leverage technology to gain efficiency and underwriting accuracy, and if they can enable high-risk borrowers to build and repair credit records, and if they can educate people about managing their finances, and can also make a great return on capital and then truly scale up…. then seemingly unsolvable problems can, maybe, begin to.get solved. More links: Study on LendUp impact on credit scores. LendUp education on credit scores. More for our listeners: I'll hope to see you at "LendIt in New York in February, SXSW in March, FinXTech Summit in April and of course CFSI’s Emerge in June. Remember to review Barefoot Innovation on iTunes, and please sign up to get emails on new podcasts and my newsletter and blog posts at jsbarefoot.com.  My latest post argues for some healthy regulatory disruption as a new administration takes office. Go there too to send in your “buck a show” to keep Barefoot Innovation going. Please also join my Facebook fan page, and follow me on twitter. Support the Podcast And watch for the next podcast, because we’re going to turn to innovation in small business lending. My guest will be Karen Mills, the former Administrator of the SBA and at Harvard Business School, where she has just issued an updated study on small business lending This one is focused mainly on fintech. We had a fascinating conversation. See you then! Subscribe Sign up with your email address to receive news and updates. Email Address Sign Up We respect your privacy. Thank you!

Sasha Orloff is the CEO and Co-founder of LendUp, a fintech startup offering online and mobile personal loans and credit cards in the United States. Prior to launching LendUp Sasha was on the other side of the table as a VC with Citi Group’s corporate venture capital arm. On the topic of VC funding, LendUp raised an incredible $150m in Jan 2016 from likes of SV Angel, Yuri Milner our friends at Susa and Google Ventures just to name a few.  In Today’s Episode You Will Learn: 1.) How did Sasha come to found LendUp following a stint in VC with Citi Group? 2.) What Sasha learnt from VC about running a successful startup and how he applied them to his founding of LendUp? 3.) Was it difficult leaving the security of a VC job to found a startup? Would you have done the same had you had children at the time? 4.) What trends in FinTech is Sasha most excited for? Why does Sasha think banks are in so much trouble? Is there the potential to co-operate rather than replace banks? 5.) How was the fundraising process for Sasha? What was his preferred round and how did they differ from stag to stage? Items Mentioned In Today’s Episode:  Sasha’s Fave Book: Banker To The Poor Sasha’s Fave Blog: Sam Altman As always you can follow The Twenty Minute VC, Harry and Sasha on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!   The Twenty Minute VC is brought to you by Leesa, the Warby Parker or TOMS shoes of the mattress industry. Lees have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is order completely online and ships for free to your doorstep. The 10 inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com/VC and enter the promo code VC75 to get $75 off!      

Connect with Fintech One-on-One: Tweet me @PeterRenton Connect with me on LinkedIn Find previous Fintech One-on-One episodes

Sasha Orloff, the CEO and co-founder of LendUp, is our next guest on the Lend Academy podcast. LendUp is different to every other company that has appeared on the podcast in that they are firmly entrenched in the subprime area. They are completely focused on serving those customers that traditional financial institutions will not or […] The post Podcast 51: Sasha Orloff of LendUp appeared first on Lend Academy.

Sasha Orloff, the CEO and co-founder of LendUp, is our next guest on the Lend Academy podcast. LendUp is different to every other company that has appeared on the podcast in that they are firmly entrenched in the subprime area. They are completely focused on serving those customers that traditional financial institutions will not or […] The post Podcast 51: Sasha Orloff of LendUp appeared first on Lend Academy.

Trends In Credit Underwriting panel at LendIt USA 2015 with Jeff Knott, of Equifax; Angela Ceresnie, of Orchard; Sasha Orloff, of LendUp; Tim Van Tassel, of FICO; Louis Beryl, of Earnest; and moderator John Hecht, of Jefferies.

This week we have special guest and CEO of LendUp, Sasha Orloff joining the conversation. We’ll be discussing opportunities in microfinance, peer to peer lending and what LendUp has already done to revolutionize payday loans. Around the coin podcast.