POPULARITY
Categories
2B Bolder Podcast : Career Insights for the Next Generation of Women in Business & Tech
What if the fastest way to grow your career is to reinvent how you work before the market forces you to? In this episode, I had the pleasure of sitting down with Caitlin Clark-Zigmond, a two-time entrepreneur and former CMO for Intel's global software and SaaS portfolio, to map the leap from hands-on operator to AI-powered brand builder, and why clear value translation beats clever slogans every time.Caitlin takes us from scaling a catering business to shipping Comcast Digital Voice, to leading massive B2B portfolios at Verizon and Intel. We dig into how Intel Tiber emerged to make software visible inside a hardware giant, uniting trust and security, AI and ML, edge and cloud, performance optimization, and developer workflows under a narrative customers could navigate. The result: sharper messaging, analyst clarity, and real pipeline acceleration. If your portfolio feels like a maze, her brand framework shows you how to draw a clean map.Then we get practical with AI go-to-market. Forget tool-chasing—start with painful use cases, build on clean, connected data, and let AI amplify what already moves the needle. Caitlin explains why a CDP or an MCP layer unlocks CRM, marketing automation, analytics, billing, and customer success, enabling them to communicate effectively with each other. We cover intent data for account prioritization, conversation intelligence for coaching, predictive scoring for pipeline, and agents that handle repetitive data pulls and weekly reporting so teams can focus on thinking, not tab-hopping.For leaders and modern marketers, the upskilling path is clear: achieve 30% fluency in core AI concepts, measurement, and understanding how your stack—HubSpot, Salesforce, GA, CDPs, and chat systems —actually works. You don't need to code; you need to understand revenue mechanics. We also share Caitlin's strategic networking system—the 5–5–5 method—that turns coffee chats into an operating system for your career, with value-first follow-ups that work even for introverts.We conclude with candid insights on the value of progress over perfection, investing in relationships before you need them, and redefining success in terms of client transformation, sustainable growth, and work-life integration. Subscribe, share with a friend, and tell us: what's the scary move you're finally ready to make?Resources: Website: www.clarkgp.com LinkedIn: https://www.linkedin.com/in/caitlinclarkzigmond Upcoming LILive GTM Event: https://www.linkedin.com/events/2026gtmrealitycheck-makemisalig7393722093324107776/Monthly Blog: https://gtmmaven.substack.com/p/why-the-c-suite-must-work-together
Today we delve into the tech expertise deficit and why technical depth and decades of doing the work matter more than social media followers and content creation hype. Our guest is Russ White, engineer, author, teacher, and certification developer. We begin with current events in AI, and then investigate the differences between career and influence... Read more »
#670 What if your website could tell exactly who was visiting — and rewrite itself just for them? In this episode, host Brien Gearin sits down with Brennan Dunn, founder of RightMessage — the software powering hyper-personalized websites and email campaigns for top creators like Ali Abdaal and Justin Welsh. Brennan shares how his journey from freelance developer to SaaS founder led him to build a tool that dynamically customizes webpages and emails based on each visitor's needs. He breaks down how segmentation works, why it drastically boosts conversions, and the unconventional marketing strategy that helped RightMessage bounce back stronger than ever. If you sell online, collect leads, or want better conversions without more traffic, this conversation is packed with insight! What we discuss with Brennan: + Origin story of RightMessage + Dynamic website personalization + Segmentation through surveys + Boosting conversions with tailored messaging + Big-name creators using the software + AB testing personalized sales pages + Partner webinars as marketing strategy + Pricing challenges and evolution of the product Thank you, Brennan! Check out RightMessage at RightMessage.com. Follow Brennan on LinkedIn. Watch the video podcast of this episode! To get access to our FREE Business Training course go to MillionaireUniversity.com/training. And follow us on: Instagram Facebook Tik Tok Youtube Twitter To get exclusive offers mentioned in this episode and to support the show, visit millionaireuniversity.com/sponsors. Want to hear from more incredible entrepreneurs? Check out all of our interviews here! Learn more about your ad choices. Visit megaphone.fm/adchoices
SaaStr 829: A Hands-On Guide to SaaStr's New AI Tools with SaaStr CEO and Founder Jason Lemkin We delve into the functionalities of our SaaStr AI tools, including the AI Mentor, which has been engaged over 100,000 times, providing answers to various startup-related queries. You'll see a demonstration of how our AI VC tools, including a startup valuation calculator, pitch deck analyzer, and benchmarking tool, work effectively to help startups understand their valuations, get honest feedback on pitch decks, and connect with VCs. Additionally, explore our newly launched VC matchmaking system and other AI agents that have been integral in automating and enhancing SaaStr's operations. Experience these tools firsthand and discover how they can add value to your startup journey. Visit SaaStr.ai to access these tools for free and see the comprehensive suite of AI agents that we use. 00:00 Introduction and Overview 00:14 Exploring SaaStr AI Tools 01:15 Deep Dive into Digital Jason 04:20 AI VC Tools and Fundraising 05:26 Startup Valuation Calculator 06:07 Pitch Deck Analyzer 16:16 Benchmarking Your Startup 18:51 VC Matchmaking and Research 21:58 Conclusion and Q&A --------------------- This episode is Sponsored in part by Salesforce: Connect data, automate busywork and empower teams like nobody's business with the one platform that grows with you, every step of the way. Learn how Salesforce works for Startups at salesforce.com/smb. --------------------- If you're serious about B2B and AI, you need to be in London this December. SaaStr AI London is bringing together more than 2,000 leaders and founders for two days of practical advice on scaling into the new year. We'll have speakers flying in from OpenAI, Wiz, Clay, Intercom, and all your favorite SaaS companies, including yours truly with Harry Stebbings for a live 20VC podcast. It'll be fun, and it's all in the heart of London. Don't miss out: get your tickets with my exclusive discount by going to podcast.saastrlondon.com --------------------- Hey everybody, the biggest B2B + AI event of the year will be back - SaaStr AI in the SF Bay Area, aka the SaaStr Annual, will be back in May 2026. With 68% VP-level and above, 36% CEOs and founders and a growing 25% AI-first professional, this is the very best of the best S-tier attendees and decision makers that come to SaaStr each year. But here's the reality, folks: the longer you wait, the higher ticket prices can get. Early bird tickets are available now, but once they're gone, you'll pay hundreds more so don't wait. Lock in your spot today by going to podcast.saastrannual.com to get my exclusive discount SaaStr AI SF 2026. We'll see you there.
On the podcast, we talk with Eric about the opportunities and challenges of AI for consumer apps, what you can learn from Strava acquiring Runna, and the flawed thinking around ‘subscription fatigue'.Top Takeaways:
SHOW: 975SHOW TRANSCRIPT: The Cloudcast #975 TranscriptSHOW VIDEO: https://youtube.com/@TheCloudcastNET NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST - "CLOUDCAST BASICS" SPONSORS:[Interconnected] Interconnected is a new series from Equinix diving into the infrastructure that keeps our digital world running. With expert guests and real-world insights, we explore the systems driving AI, automation, quantum, and more. Just search “Interconnected by Equinix”.[TestKube] TestKube is Kubernetes-native testing platform, orchestrating all your test tools, environments, and pipelines into scalable workflows empowering Continuous Testing. Check it out at TestKube.io/cloudcastSHOW NOTES:LaunchAny websiteapicoach.io (note)Lessons learned after a decade of API StrategyLatest book: “Principles of Web API Design: Delivering Value with APIs and Microservices (Addison-Wesley under the Vaughn Vernon signature series)Upcoming report on AI-Assisted API DesignJames on The Cloudcast #153James on The Cloudcast #435Topic 1 - Welcome back to the show James. It's hard to believe it's been 11 years since we last spoke on the show! Give everyone a brief introduction.Topic 2 - To say we've come a long way with APIs as an industry is an understatement. But let's set the table for everyone. In your interactions with Enterprise customers, what trends or standards are currently top of mind? Topic 3 - You wrote an article (link in show notes) titled Lessons after a Decade of API Strategy. What struck me from the article was the combination of technology, business, and even culture, all of which have to come together. When talking to Enterprises these days, have we moved past understanding what APIs are and straight to solving problems with APIs?Topic 4 - What are the most common use cases you see today? API transformation? API sprawl and consolidation/documentation? Integration of SaaS/3rd party services?Topic 5 - No conversation would be complete without a discussion about AI and AI's impact on API's. I view this in several different ways. AI is creating APIs, and AI is being consumed through APIs. How do you think about AI and its impact? What's changed and what has stayed the same?Topic 6 - Second aspect to the AI topic, where and how does security fit into this intersection of AI and APIs?Topic 7 - If anyone is interested, what's the best way to get started?FEEDBACK?Email: show at the cloudcast dot netBluesky: @cloudcastpod.bsky.socialTwitter/X: @cloudcastpodInstagram: @cloudcastpodTikTok: @cloudcastpod
If your product strategy stops at the download, you're leaving impact—and revenue—on the table. In this conversation, I sit down with Ghazenfer Mansoor, CEO & founder of Technology Rivers, to talk about building software that actually gets used, loved, and shared. Ghazenfer has been in mobile since the pre-iPhone days and has led the build of nearly 60 apps, primarily in healthcare. We explore ideas from his forthcoming book, Beyond the Download, including why retention beats acquisition, when a mobile app truly makes sense (and when a web experience is smarter), and how AI-driven, proprietary workflows can become a company's real moat. We also step into leadership, including what it takes to fix “broken” projects, the values that guide his global remote team (transparency, fairness, and getting things done), and why peer networks and coaching matter for founders. It's a practical, fast-moving chat for leaders who want their technology to create efficiency, differentiation, and long-term value. Here are some highlights: -Retention over acquisition: Ghazenfer shares practical ways to design for daily use and bring people back because downloads without engagement aren't success. -“Do you really need an app?”: We unpack decision criteria for native vs. web, and why solving a real, repeat problem is the first gate before writing any code. -Workflow is the moat: How codifying proprietary processes, especially in healthcare and HIPAA-sensitive environments, creates efficiency, margin, and higher valuations. -Fixing broken projects: Common failure patterns (from feature chasing to UX missteps) and how to course-correct so you “build it right the first time.” -Leading a global team: The operating system behind Technology Rivers; clear KPIs, remote-first communication, fairness, and a growing commitment to women in tech. Plus the role of EO/Vistage-style peer groups and coaching for tough decisions. About the guest: Ghazenfer Mansoor is the founder and CEO of Technology Rivers, a Washington, D.C.–area software firm specializing in HIPAA-compliant healthcare SaaS and mobile apps. A mobile veteran since the pre-iPhone era, he has led the build of 59+ apps and numerous AI-powered workflow platforms that help service businesses scale, boost margins, and increase valuation. Known for “building it right the first time,” Ghazenfer is frequently tapped to rescue broken software projects. He's the author of the forthcoming book Beyond the Download: How to Build Mobile Apps That People Love, Use, and Share Every Day and host of the podcast Lessons from the Leap. Active in EO and other CEO peer groups, he leads a global, values-driven team grounded in transparency, fairness, and getting things done. Connect with Ghazenfer: Website: https://technologyrivers.com/ LinkedIn: https://www.linkedin.com/in/gmansoor/ Connect with Allison: Feedspot has named Disruptive CEO Nation as one of the Top 25 CEO Podcasts on the web, and it is ranked the number 6 CEO podcast to listen to in 2025! https://podcasts.feedspot.com/ceo_podcasts/ LinkedIn: https://www.linkedin.com/in/allisonsummerschicago/ Website: https://www.disruptiveceonation.com/ #CEO #leadership #startup #founder #business #businesspodcast Learn more about your ad choices. Visit megaphone.fm/adchoices
Hey CX Nation,In this week's CXWeekly Update episode I walk through some ideas, goals & CTAs that me & the team at CXC have been focused on.Full candor, we're in a full blown sales sprint to the end of the year to close 2025 with a bang & tee up the best year yet in 2026.We're also working on a ton of new customer focused business content -- including my 2nd book "Make Happiness A Habit" that we are launching in the New Year. Don't worry we have a ton of amazing guest interviews coming down the pipeline over the next couple of weeks.Part of our goal at CXC is to create some of the best customer focused business leader content, including short episodes like these CXWeekly updates that are digestible, actionable & most importantly entertaining for all of you.Huge thanks for all of you who helped to celebrate our 5 year anniversary of building CXChronicles, it's been a hell of a journey. Approaching 300+ episodes of customer focused business contentWorked with 150+ companies across the world helping make customer & employee happiness a habitPartnered with biggest players in software & technology including Salesforce, Hubspot, Intercom, Zendesk, & Freshworks.Launched CXC Healthzone Intelligence Platform, go see how your company's CX stacks up the rest. If you enjoy The CXChronicles Podcast, stop by your favorite podcast player and leave us a review today.You know what would be even better?Go tell one of your friends or teammates about CXC's content, CX/CS/RevOps services, our customer & employee focused community & invite them to join the CX Nation!For you non-readers, go check out the CXChronicles Youtube channel to see our customer & employee focused video content & short-reel CTAs to improve your CX/CS/RevOps performance today (politely go smash that subscribe button).Contact us anytime to learn more about CXC at INFO@cxchronicles.com and ask us about how we can help your business & team make customer happiness a habit now!Reach Out To CXC Today!Support the showContact CXChronicles Today Tweet us @cxchronicles Check out our Instagram @cxchronicles Click here to checkout the CXC website Email us at info@cxchronicles.com Remember To Make Happiness A Habit!!
The world record for fastest pit stop—a mere 1.8 seconds—was set by the McLaren F1 Team at the Qatar Grand Prix in 2023. It's an incredible feat of speed and choreography; a pit stop that fast can't happen without a team of people operating at peak human performance. But as Dan Keyworth explains, AI plays a crucial role, too. As the Director of Business Technology at McLaren Racing, Dan is responsible for helping the whole team perform at their best—and that starts with having the right tools. Whether it's the firehose of sensor data coming off a race car, video analysis of the pit crew in action, or marketing analytics for the next Grand Prix, AI helps the McLaren F1 Team make the right decisions—and make them fast.On this episode, Dan talks about the importance of getting simple answers from complex data, how they use Dropbox Dash, and why we shouldn't think of AI as labor replacement so much as laborious replacement.You can learn more about the McLaren F1 Team at mclaren.com/racing/formula-1. And if you haven't already seen it, be sure to watch their world record pit stop at youtube.com/watch?v=tRBOiq-Q6_s. Seriously, it's blink-and-you'll-miss-it fast.~ ~ ~Working Smarter is brought to you by Dropbox Dash—the AI universal search and knowledge management tool from Dropbox. Learn more at workingsmarter.ai/dashYou can listen to more episodes of Working Smarter on Apple Podcasts, Spotify, YouTube Music, Amazon Music, or wherever you get your podcasts. To read more stories and past interviews, visit workingsmarter.aiThis show would not be possible without the talented team at Cosmic Standard: producer Dominic Girard, sound engineer Aja Simpson, technical director Jacob Winik, and executive producer Eliza Smith. Special thanks to our illustrators Justin Tran and Fanny Luor, marketing consultant Meggan Ellingboe, and editorial support from Catie Keck. Our theme song was composed by Doug Stuart. Working Smarter is hosted by Matthew Braga. Thanks for listening!
In this episode of The Product Experience, Lily Smith speaks with Vidya Dinamani, product veteran, coach, and Co-founder of Product Rebels, about how to tell if your team is truly product-led or just paying lip service. With over a decade of experience coaching hundreds of teams, Vidya shares her insights into the critical elements of product maturity, the most overlooked barriers to effective product work, and how Product Rebels' diagnostic framework is helping companies move from chaos to clarity. Chapters00:00 – The customer conversation gap01:28 – Meet Vidya Dinamani and Product Rebels03:35 – Why they built a diagnostic, not an assessment04:45 – Mindsets, competencies, and the missing piece: resources06:28 – AI readiness: the new fourth pillar07:40 – What it really means to be product-led09:59 – How teams are using the diagnostic13:10 – Breaking down the four pillars16:01 – Why access to customers remains a key obstacle17:38 – Patterns, or lack thereof, in product maturity20:26 – AI readiness in context23:59 – A case study: product maturity at scale27:52 – Final thoughts on assessment vs namingWhat we learned from Vidya Most product teams lack customer access: 70–80% of PMs Product Rebels encounter say they've never spoken to a customer.Being product-led requires more than intent: It demands mindset, core competencies, supportive resources—and now AI readiness.Diagnostic, not assessment: Their tool isn't about performance reviews; it's a heat map that reveals where to begin your transformation.AI is not a bolt-on: AI readiness is most effective when integrated into the broader product maturity conversation, not treated as a silo.Start with one thing: Rather than trying to become product-led across the board, identify a single focus area and build momentum from there.Internal PMs need customer framing too: Even teams building internal platforms need customer advocacy and insight.Featured Links: Follow Vidya on LinkedIn | Product Rebels We're taking Community Questions for The Product Experience podcast.Got a burning product question for Lily, Randy, or an upcoming guest? Submit it here. Our HostsLily Smith enjoys working as a consultant product manager with early-stage and growing startups and as a mentor to other product managers. She's currently Chief Product Officer at BBC Maestro, and has spent 13 years in the tech industry working with startups in the SaaS and mobile space. She's worked on a diverse range of products – leading the product teams through discovery, prototyping, testing and delivery. Lily also founded ProductTank Bristol and runs ProductCamp in Bristol and Bath. Randy Silver is a Leadership & Product Coach and Consultant. He gets teams unstuck, helping you to supercharge your results. Randy's held interim CPO and Leadership roles at scale-ups and SMEs, advised start-ups, and been Head of Product at HSBC and Sainsbury's. He participated in Silicon Valley Product Group's Coaching the Coaches forum, and speaks frequently at conferences and events. You can join one of communities he runs for CPOs (CPO Circles), Product Managers (Product In the {A}ether) and Product Coaches. He's the author of What Do We Do Now? A...
A story about choosing autonomy over speed—and building something that lasts.This episode is for SaaS founders tired of chasing growth rounds—and wondering if slow, profitable building could win.Most software companies raise capital to scale fast. Rex Kurzius, Founder of Asset Panda, rejected that path entirely. His father ran a bakery. His brother built MailChimp. Rex grew up watching immigrant work ethic turn into entrepreneurial success—and applied the same principle to software.He spent 13 years building Asset Panda from startup to a world-class asset tracking platform. No investors. No board pressure. No artificial timelines. Just solving one problem—asset tracking—and letting customer revenue fund each next step.And this inspired me to invite Rex to my podcast. We explore why staying curious matters more than being right. Rex shares his thinking on positioning pivots (consumer to business, product to platform), building without investor timelines, and the inverse relationship between AI and headcount growth. You'll discover why he calls himself the turtle in the race—and what slow, steady building creates.We also zoom in on three of the 10 traits that define remarkable software companies: Master the art of curiosity Focus on the essence Turn customers into fansRex's story is proof that building slow beats chasing speed—when you solve real problems.Here's one of Rex's quotes that captures his growth philosophy:"It's not about being perfect, and it's not about being right. It's about being curious and having the ability to deal with failure, learn from that failure, and adapt to succeed."By listening to this episode, you'll learn:Why staying curious beats being right when building softwareWhat happens when you fund growth with customer revenue, not investor capitalWhy solving client problems matters more than hitting investor timelinesHow building slow creates more enduring value than chasing speedFor more information about the guest from this week:Guest: Rex Kurzius, Founder and CEO of Asset PandaWebsite: assetpanda.com
In this episode of Future Finance, Glenn Hopper and Paul Barnhurst sit down with Joe Friedman and Ranga Bodla from Oracle NetSuite to explore how AI is transforming enterprise resource planning (ERP) systems. Amidst rising competition and a rapidly changing tech landscape, NetSuite is doubling down on intelligent automation, open platforms, and embedded AI to redefine how finance teams operate.Joe Friedman is the Senior Director of AI Innovation at Oracle NetSuite, driving efforts to integrate practical AI across finance and operations. With over 15 years at NetSuite, Joe focuses on converting AI into measurable productivity gains. Ranga Bodla is the Vice President of Field Engagement and Marketing at Oracle NetSuite, with more than 20 years in enterprise software. He leads industry strategy across verticals, helping businesses convert innovation into performanceExpect to Learn:Why AI is reinvigorating interest in ERP platforms like NetSuite.How NetSuite's AI strategy balances “AI every day” and “AI your way.”What the MCP connector does and why it's a game-changer for data analysis.How NetSuite's clean data models fuel better AI outcomes and user productivity.Joe Friedman and Ranga Bodla offer a compelling look at how NetSuite is embedding AI into the core of ERP to drive smarter, faster decision-making. Their insights show that clean data, open platforms, and practical AI tools are key to transforming finance operations today.Join hosts Glenn and Paul as they unravel the complexities of AI in finance:Follow Joe:LinkedIn: https://www.linkedin.com/in/friedman-ns/Follow Ranga:LinkedIn: https://www.linkedin.com/in/ranga-bodla-bb45b/Follow Paul: LinkedIn - https://www.linkedin.com/in/thefpandaguyFollow QFlow.AI:Website - https://bit.ly/4i1EkjgFuture 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. Stay tuned for a deeper understanding of how AI is shaping the future of finance and what it means for businesses and individuals alike.In Today's Episode:[02:00] – Where NetSuite Stands in Today's ERP Landscape[05:17] – Why ERP and AI Go Hand-in-Hand[07:29] – AI Every Day, AI Your Way: What NetSuite's MCP Connector Unlocks[10:29] – Practical AI Integration Inside NetSuite[13:30] – Real-World Use Cases for AI in Finance[16:22] – AI Agents, Automation, and What's Coming Next[18:05] – SaaS as the Real Driver of AI Adoption[19:48] – Why Clean Data Fuels Better AI Outcomes[21:12] – Closing Thoughts
The evolution of the modern, Internet-driven economy has created the conditions for essentially unbounded Nth-party risks (that is, risks from your suppliers, and risks from your suppliers’ suppliers, and risks from your suppliers’ suppliers’ suppliers, ad infinitum). Nth party risks exist in public clouds, SaaS, software and hardware supply chains, and now in the form... Read more »
Blair Williams is the CEO of MemberPress, a powerful WordPress plugin company that empowers creators and businesses to launch and manage membership sites and online courses. He founded MemberPress after years of custom-building membership systems and recognized a gap in the market for a flexible, developer-friendly WordPress solution. Blair is also the Owner of Caseproof, the company behind industry-leading WordPress plugins like MemberPress, PrettyLinks, Easy Affiliate, Wishlist Member, MemberMouse, AccessAlly, ThirstyAffiliates, and Buy Now Plus. In this episode… Building a thriving membership business requires more than great content — it takes strategy, the right tools, and a deep understanding of your audience. From simplifying user experiences to streamlining revenue models, entrepreneurs must balance creativity with technical precision to keep members engaged. So how do you create a membership site that actually scales and sustains long-term success? A seasoned innovator in software and membership platforms, Blair Williams believes simplicity and customer focus are the keys to success. He highlights that many creators overcomplicate their offerings before launching, when the real key is just getting started and refining through feedback. Blair emphasizes the power of accessibility — tools like WordPress and AI have made building profitable membership sites easier than ever. He also points out that success stems from aligning features with audience needs, whether through strong onboarding, smart pricing models, or seamless integrations that enable entrepreneurs to monetize their expertise efficiently. In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz sits down with Blair Williams, CEO of MemberPress, to discuss the tools and tactics that power successful membership businesses. They discuss common mistakes creators make when launching sites, how to simplify offers for growth, and what makes MemberPress stand out in the WordPress ecosystem. Blair also shares lessons from building and acquiring top plugins across the web.
In this episode, we discuss MuleSoft and Camel similarities and take a brief tangent on the prevalence of XML as a data format, vibe-coding, SaaS fatigue, subscription overload, and Illuminated Cloud's support for GraphQL.
Your gross margin might not be telling the truth. In episode #327, Ben Murray exposes the seven “dirty secrets” that distort SaaS gross margins — from incorrect COGS coding to missing allocations for shared resources and misclassified expenses. Whether you're a CFO, finance lead, or operator, you'll learn how to clean up your P&L and get accurate unit economics that reflect your true performance and valuation. What You'll Learn The 7 big offenders that make SaaS gross margins misleading. How to correctly code payment processing fees (Stripe, ACH, wire) under DevOps in COGS. The difference between internal-use software and third-party apps embedded in your product. How to classify customer success — adoption-focused vs. account management. Why demo and test environments must be allocated properly between departments. How to ensure fully burdened expenses (wages, taxes, benefits, bonuses) are coded correctly. The impact of co-mingled headcount on margins by revenue stream. Why department leaders belong in the departments they manage. Why It Matters For Founders: Clean accounting drives higher (or preserved) company valuation and investor confidence. For Finance Teams: Accurate COGS and gross profit ensure your SaaS metrics are reliable. For Operators: Clear expense allocation helps identify efficiency opportunities in support, services, and DevOps. For Investors: Properly structured financial systems and accounting practices make due diligence faster and cleaner. Key Takeaways Misclassified expenses can make your gross margin appear stronger or weaker than it really is. Always differentiate between OpEx and COGS — the foundation of credible financial modeling. Track margins by revenue stream (subscription, usage, services) for true business insight. Ensure your P&L reflects fully burdened costs per department — including contractors. Clean financial data = higher trust from investors and buyers. Resources Mentioned SaaS Metrics Foundation Course: https://www.thesaasacademy.com/the-saas-metrics-foundation Quote from Ben “Your P&L doesn't lie — but bad coding does. If your COGS and OpEx aren't clean, your gross margin isn't either.”
The evolution of the modern, Internet-driven economy has created the conditions for essentially unbounded Nth-party risks (that is, risks from your suppliers, and risks from your suppliers’ suppliers, and risks from your suppliers’ suppliers’ suppliers, ad infinitum). Nth party risks exist in public clouds, SaaS, software and hardware supply chains, and now in the form... Read more »
In this episode, Carl Holden joins Jeff Mains to dive deep into the evolution of SEO, its marriage with AI, and the realities of scaling a SaaS business honestly in a world awash with hype and misinformation. Carl Holden shares his journey from running a leading agency to launching RankBot, an AI-powered tool that automates SEO backlinks for businesses and agencies.Together, they discuss the myths and challenges in transitioning from services to SaaS, the role of human expertise alongside automation, and why authenticity and steady results still win over quick fame. Tune in for actionable insights, candid leadership lessons, and advice on building products and companies that last.Key Takeaways00:00 SEO vs AI Search Trends04:38 "Zero-Click Search Impact"09:25 "AI-Coded Rank Bot Success"12:39 Automated Link-Building Solution15:12 "Importance of Links in SEO"18:05 Automated Link-Building Solution21:07 "Bots for Targeted SEO Tasks"27:55 Risks of Automated Content Control28:50 AI Marketing Red Flags & Promises35:07 "Scaling Automation for Market Adjustments"39:31 Future Where Witnesses Are Needed41:26 Start, Fail, Improve, Repeat44:25 Easy Connections via Networking PlatformsTweetable Quotes“Everybody can make a nice website, but who else out there on the Internet is talking about your nice website? That's where links come in.” — Carl Holden“AI is starting to take certain tasks, and if you do anything regularly with patterns, AI will help—or do that in the future.” — Carl Holden“Organic traffic is not going away at this time. The way we get traffic may shift, but people still need it.” — Carl Holden“If money is all that matters, there are plenty of dishonest ways to get rich. But when you're dead, you don't get to keep it.” — Carl Holden“You want people to do business with you because you're good, not because you're popular.” — Carl Holden“Consistent authenticity—being out there telling people what you do and having a good product—will win over time.” — Carl HoldenSaaS Leadership LessonsEmbrace Change, Don't Run From ItWhen you see an industry shifting (like with AI), lean into change and make yourself indispensable by creating value within the new paradigm.Balance Optimism and Caution with New TechDon't blindly trust automation or AI—always validate and maintain oversight. The best results come from combining human judgment with smart tools.Build in Public, Iterate QuicklyLaunch your MVP, gather feedback, and improve over time. Perfection is the enemy of progress.Results Over HypeFocus on delivering genuine results; honest, consistent effort leads to sustainable success more than chasing trends or flashy viral tactics.Be Authentically Honest in Marketing & ProductResist the urge to oversell or stretch the truth—long-term, authenticity and integrity win client loyalty and positive reputation.Stay on Top of Industry ShiftsIn dynamic markets like SEO, regular learning and adaptation are critical. Monitor changes, test new strategies, and never get complacent.Guest Resourcescarl@rankbotai.comrankbot.aihttps://www.linkedin.com/in/carlholdenmarketing/Episode Sponsor
Ian and Aaron talk about 20 years of HelpSpot, Aaron's big week on Twitter, and....talk about burying the lede....Aaron's got ARR! Subscription revenue! It's happening!Sponsored by Bento, Flare, and Ittybit.Interested in sponsoring Mostly Technical? Head to https://mostlytechnical.com/sponsor to learn more.(00:00) - A Weekend Story (15:25) - Sick Kids (20:12) - Laravel New Update (22:40) - 20 Years of HelpSpot (37:27) - Ian's Hiring (43:03) - Aaron's Big Week on Twitter (53:20) - Database School Update Links:Paperless PostFuji X100VIRicoh GR IVLaravel NewIan's hiring!Aaron's tweet"Put Food On My Family"
Most misses in sales are baked into the plan before the year even starts.In this episode, Toni talks with Scott Domareck, a four-time VP of Sales who's been through every phase of growth, exit, and burnout imaginable. Together, they break down the hidden mistakes that ruin annual planning long before execution begins.From massaged Excel spreadsheets to unrealistic ramp times and compounding assumptions that look great to investors but kill execution, they get real about what actually happens inside revenue planning season, and how to build a plan you can actually hit.This episode is brought to you by Evergrowth — Their Agentic GTM Workspace enables revenue teams to collaborate and win with AI-powered teammates, breaking down silos and helping B2B teams grow smarter with fewer resources. Want to work with us? Learn more: revformula.io(00:00) - Introduction (04:16) - The Reality of Planning Season (07:22) - Transparency and Context in Planning (13:12) - Compounding Effects in Sales Planning (18:14) - Involvement of Go-to-Market Leadership (25:29) - Trust and Executive Leadership (28:43) - Top Mistakes in Hiring (30:49) - Staggering for Supply and Demand (34:02) - Challenges in Scaling and Execution (41:04) - The Reality of Adding New Elements to the Plan (43:34) - Risk Management and Buffers (46:31) - Planning for Attrition and Unexpected Events (49:13) - Final Thoughts and Future Discussions
In this episode, we sit down with Fabian Veit, CEO of Make.com, to talk about what it really takes to scale not just one but two hyperscale SaaS companies - first in a classic enterprise sales-led motion, and now in a PLG + AI/automation world. Fabian shares how Make has 15x'd revenue and grown from ~50 to nearly 400 people, while racing past 100k+ paying customers and aiming for €100M+ ARR, and why that requires a fundamentally different mindset than selling multi-million euro deals into the Fortune 2000. He contrasts the “one deal can make your quarter” reality of enterprise sales with the high-volume, product-first, self-serve motion of Make, where thousands of users sign up every month and the product has to carry the weight. We also dig into what it means to build in the middle of the AI & agentic wave when your platform is literally how people wire AI into their business processes. Fabian explains why most AI projects are actually 80–90% integrations & automation, where AI is the smart layer inside the flow, not the whole show, and how Make is evolving from classic “if-this-then-that” workflows into visual AI agents that power real operations. You'll hear Fabian talk about: PLG vs Sales-Led: What changed when he went from 9–12 month, high-touch enterprise cycles at Celonis to Make's “sign up free, upgrade yourself” engine. Rebuilding While Scaling: Why everything is always breaking in hypergrowth, and how he decides what to fix for 5× future scale, not just today. Brand & Positioning Pivots: The risky shift from Integromat to Make.com, losing SEO in the short term to win a much bigger global brand in the long term. Culture at Hyperspeed: How they keep their values intact with hundreds of new hires through explicit values & operating principles, and a brutal honesty policy inspired by Radical Candor. The AMA Channel: An internal Ask Me Anything Slack channel where anyone can ask leadership anything (even anonymously), and why Fabian believes answering every question publicly is non-negotiable for trust. We wrap up with Fabian's view on where we are in the AI hype cycle, why he compares this moment more to the industrial revolution than just another tech fad, and what kinds of human skills will matter even more in an AI-driven world.
On this episode we dive deep into Glif. This beginner tutorial shows how AI agents on Glif automatically optimize prompts and workflows to create scroll-stopping content. We demo four agents live: Mr. Beast-style thumbnails, miniature documentaries, AI influencer videos, and automated Reddit story content. Total cost: $2. Timestamps: 00:00 – Intro 03:35 – Nano Banana Ultimate 08:53 – Diorama Shorts Creator 15:49 – AI Influencer Generator 23:27 – TikTok Reddit Story Creator 32:28 – Conclusion and Final Thoughts Key Frameworks: The ACP Funnel (Audience → Community → Product) Build businesses in this order: First create an Audience with storytelling/content (use creative AI here), then build a Community with paid memberships or IRL events, then create a Product to sell to them. This gives you the highest probability of success. Modern Social Strategy: 1 Brand + 10 People Old way: 1 brand account on multiple platforms. New way: 1 brand account + 10 different people accounts (real and AI influencers) across platforms. If 1-2 of 10 pop off, you win. Four Demos Shown: Nano Banana Ultimate: Redesigned thumbnail Mr. Beast-style with proper aspect ratios, high contrast, exaggerated expressions—got 3 variants that couldn't be achieved with regular Nano Banana Miniature Documentary Creator: Created 40-second tilt-shift video about Facebook IPO in ~5 minutes using Seadream, WAN 2.2, 11Labs—includes research, script, voiceover, animations, period music, and subtitles (agencies charge thousands; this cost $0.40) AI Influencer Generator: Generated 35-year-old woman in tennis clothing using Quen Realism and OmniHuman—creates realistic talking head videos for brand representative accounts or video ads at zero production cost Reddit Story Automation: Scraped r/SaaS for story about developer building $1M SaaS through Reddit, generated educational 60-second video with voiceover, Pexels stock footage, and subtitles—enables faceless content channels (example cited: 67% of customers from Reddit, zero CAC) Key Insight: AI agents get you 80% there but you still need to be the creative director, push agents to create better scripts, expect to iterate, and manually review for character consistency and details. The #1 tool to find startup ideas/trends - https://www.ideabrowser.com LCA helps Fortune 500s and fast-growing startups build their future - from Warner Music to Fortnite to Dropbox. We turn 'what if' into reality with AI, apps, and next-gen products https://latecheckout.agency/ Boringmarketing - Vibe Marketing for Companies: boringmarketing.com The Vibe Marketer - Join the Community and Learn: thevibemarketer.com Startup Empire - get your free builders toolkit to build cashflowing business - https://startup-ideas-pod.link/startup-empire-toolkit Become a member - https://startup-ideas-pod.link/startup-empire FIND ME ON SOCIAL X/Twitter: https://twitter.com/gregisenberg Instagram: https://instagram.com/gregisenberg/ LinkedIn: https://www.linkedin.com/in/gisenberg/
Struggling with ineffective tech teams or expensive agencies? Vygandas Pliasas, a seasoned Fractional CTO, reveals how to streamline development, build high-performing in-house teams, and achieve sustainable growth. Tune in for actionable insights to align your tech strategy with your business goals.
This week on Make It Happen Mondays, John sits down with Rory Sadler, Co-founder and CEO of trumpet, the leading digital sales room platform helping companies like Gong, HubSpot, and Personio increase sales velocity by transforming the buying experience.Before founding trumpet, Rory spent years on the front lines of SaaS sales—first as an individual contributor, then leading global teams at Hotjar. Along the way, he saw firsthand just how painful and chaotic buying software had become—and made it his mission to fix it.In this episode, Rory shares the aha moment that led to building trumpet, his early entrepreneurial grit (selling sweets and DJing as a teen), and why entrepreneurship is way different than just working at a startup. We also dive into:Why buyer enablement is the new sales enablementHow mutual action plans build real trust and alignmentWhat sellers are still getting wrong about personalizationThe massive opportunity in simplifying complex buying decisionsIf you're in sales, RevOps, or just care about delivering a smoother, faster, and more human buying experience, this episode will hit home.Are you interested in leveling up your sales skills and staying relevant in today's AI-driven landscape? Visit www.jbarrows.com and let's Make It Happen together!Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/Connect with John on IG: https://www.instagram.com/johnmbarrows/Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletterConnect with Rory on LinkedIn: https://www.linkedin.com/in/rory-sadler-trumpet/ Connect with Trumpet on LinkedIn: https://www.linkedin.com/company/sendtrumpet/Check out Rory's Website: https://www.sendtrumpet.com/
He walked away from a cushy job to build products in his garage. Here's how he made it work. Today, we're talking to Scott Henderson, CTO and Co-founder at Celigo. We discuss why AI needs minimal autonomy instead of maximum freedom, how the future of SaaS is chat-to-validate rather than click-to-execute, and why the most expensive AI mistake is adopting it too slowly rather than spending too much. All of this right here, right now, on the Modern CTO Podcast! To learn more about Celigo, check out their website here.
Akshat Vaidya – Managing Partner & Co-Founder, MaelstromAkshat Vaidya is the Managing Partner and Co-Founder of Maelstrom, the family office founded by BitMEX co-founder Arthur Hayes. In this role, Akshat leads Maelstrom's investment strategy across its multiple verticals, including venture investments, liquid markets, and private equity deals. He oversees the recently launched Maelstrom Equity Fund I (a US$250 million fund) which focuses on acquiring mid-sized, profitable companies in the crypto-infrastructure space.Akshat's journey into digital assets began over a decade ago. He first started buying Bitcoin in 2013 while still working in traditional finance. Before co-founding Maelstrom, he served as Head of Corporate Development and M&A at BitMEX, where he led the exchange's expansion through acquisitions and strategic partnerships. Earlier in his career, Akshat was an investor at Granite Creek Capital Partners, executing leveraged buyouts and growth investments in U.S. middle-market companies. He holds a Bachelor's in Economics from the Wharton School of the University of Pennsylvania, combining a classic finance education with a forward-looking tech perspective.Under Akshat's leadership, Maelstrom has grown from a two-person family office into a multi-strategy investment platform. The firm now operates across venture capital, liquidity provisioning, and private equity initiatives. Akshat remains a champion of long-term value creation in a market often driven by hype and short cycles. He strives to bridge traditional financial rigor with digital-asset innovation, ensuring Maelstrom's portfolio is built on strong fundamentals and sustainable growth. LinkedIn: https://www.linkedin.com/in/akshatvaidya/Adam Schlegel – Partner & Head of Private Equity, MaelstromAdam Schlegel is a Partner at Maelstrom, where he leads the firm's private equity strategy and heads its debut buyout vehicle, Maelstrom Equity Fund I. With over a decade of experience in traditional private equity and cross-border transactions, Adam brings institutional discipline to the evolving crypto-infrastructure space. He joined Maelstrom to expand its reach into buyouts of established crypto-industry companies, applying proven investment frameworks to this emerging sector.In his previous roles, Adam built a strong foundation in global finance. He was an Investor at Haveli Investments – the Austin-based private equity firm founded by Brian Sheth (co-founder of Vista Equity Partners) – focusing on enterprise SaaS buyouts and growth-equity deals. Prior to Haveli, he served as an Associate at Baring Private Equity Asia, executing large cross-border transactions across the Asia-Pacific region. Adam began his career as an Investment Banking Analyst in Morgan Stanley's Global Energy Group, where he gained experience in capital markets and corporate finance. He holds a Master of Arts in International Finance from Johns Hopkins University's School of Advanced International Studies (SAIS) and a Bachelor of Arts in Political Science (with a minor in Chinese) from Swarthmore College.At Maelstrom, Adam is driving the firm's expansion into private equity by identifying and acquiring crypto-infrastructure and data analytics companies that meet specific criteria. Adam's approach blends traditional buyout expertise with a deep understanding of how digital assets, stablecoins, and decentralized finance are transforming financial infrastructure worldwide. By applying classic private equity frameworks (e.g. rigorous due diligence, operational improvements, and long-term value creation plans) to crypto-enabled businesses, he aims to bridge the gap between conventional finance and the crypto economy. LinkedIn: https://www.linkedin.com/in/adam-schlegel-2b5247b/
SaaS Scaled - Interviews about SaaS Startups, Analytics, & Operations
Today, we're joined by Chris McHenry, Chief Product Officer at Aviatrix, a cloud native network security company. We talk about:Prerequisites to driving operational efficiency with agentic AIBridging the gap between security & engineering so organizations can go fast & be secure What's required in order for agentic AI to create a magical momentWith cloud powering so much of our society, the need to get security right The security challenges introduced by agentic AI apps, including new attack vectors
In this episode of Run the Numbers, CJ Gustafson sits down with Colin Gardiner, General Partner at Yonder VC and former Chief Revenue and Product Officer at Outdoorsy, to unpack what really drives successful marketplace businesses. Colin shares lessons from scaling a peer-to-peer RV platform, where the biggest unlock came not from casual users but from power hosts optimizing utilization and yield through the SaaS tools they built. He introduces his “Marketplace Plus” investing framework—showing how layering SaaS and professional tools can transform a platform into an operating system—and where founders risk overreaching by taking on inventory or managing supply too tightly. The conversation dives deep into monetization, pricing psychology, take rates, and the fine balance between product-market fit and margin obsession, before zooming out to explore how AI and the decline of SEO are reshaping marketplace discovery.—LINKS:Colin on LinkedIn: https://www.linkedin.com/in/colingardiner/Company: https://www.yonder.vc/CJ on X (@cjgustafson222): https://x.com/cjgustafson222Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:996 Culture, Exploding AI Bills & SaaS Chaoshttps://youtu.be/qhrxDL0gsRo“Keep the Take Rate Low” - Turo's Chuck Fisher on Scaling a Successful Peer-to-peerhttps://youtu.be/LKH8o1MjnZoThe Art of Stacking S-Curves: Olo's Winning Vertical SaaS Strategy with CFO Peter Benevideshttps://youtu.be/1X2VoYogj44—TIMESTAMPS:00:00:00 Intro and Guest Overview00:02:57 Sponsors – RightRev, Tipalti, and Aleph00:07:13 Outdoorsy and the RV Market00:10:33 Balancing Supply and Demand00:13:05 Marketplace Plus Model00:16:59 Sponsors – Fidelity Private Shares, Metronome, and Mercury00:21:45 Professionalizing Marketplaces00:24:10 Building Software, Insurance, and Financing Layers00:28:07 Avoiding Fully Managed Models00:32:34 Take Rates and Pricing Strategy00:35:00 Monetizing Both Sides00:37:06 Advertising and Marketplace Scale00:39:48 Marketplaces Meet Social Platforms00:42:36 AI and Marketplace Distribution00:45:54 AI Agents and Matchmaking00:47:03 When AI Becomes the Supply00:49:09 Negative Gross Margins and Scale00:53:04 Picking a Side – Supply or Demand00:54:35 Branding, Utilization, and Growth00:55:42 Closing and Credits—SPONSORS:RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comMercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com—#RunTheNumbersPodcast #MarketplaceStrategy #AIPoweredBusiness #SaaSModel #StartupFinance This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com
Many organizations believe that Microsoft 365 backup is handled by Microsoft. That's a dangerous misconception. In this episode, W. Curtis Preston (Mr. Backup) and Microsoft 365 expert Vanessa Toves explain why you own your data and are responsible for protecting it—not Microsoft. They discuss the limitations of the recycle bin, why retention policies aren't backups, and what can go wrong when organizations assume SaaS means hands-off data protection. Whether you're running a Fortune 500 company or a small business, if you're using Microsoft 365, you need a proper backup solution. Learn why the shared responsibility model means you're on the hook for your data, and what you can do to protect it. This conversation will change how you think about cloud data protection.
What if the real story of AI isn't about chatbots or copilots at all, but about what happens when intelligence becomes part of the infrastructure of how work gets done? That's the idea driving this conversation with Vahid Taslimi, CEO and co-founder of Zenphi, who joins me from Melbourne, Australia, to discuss how his team is quietly redefining the way organizations think about automation. Vahid believes the real potential of AI lies not in flashy interfaces or generative tools, but in its ability to act as an invisible layer that powers everyday business operations. He explains how Zenphi is embedding AI into workflow automation for companies across sectors—from Gordon Food Service, which uses AI to manage access reviews and reduce shadow IT, to Action Behavior Centers in the US, where AI ensures compliance in sensitive healthcare processes. In each case, the focus is on operational AI that improves efficiency, accuracy, and decision-making without exposing organizations to unnecessary risk. We also talk about the importance of starting small, proving value, and scaling sensibly, echoing lessons learned from the early days of SaaS adoption. Vahid shares his views on how to move from AI experiments to enterprise-wide deployment, how to build compliance and governance into every layer, and why the future of automation depends on empowering non-developers to shape their own workflows. His no-code approach is enabling HR, finance, and operations teams to experiment safely with AI, achieving compounding gains without depending entirely on IT departments. Throughout our chat, Vahid brings to life the concept of "AI as infrastructure" with grounded stories and practical insights. He also reflects on how Zenphi balances innovation with reliability, ensuring that even regulated industries can integrate AI responsibly. As he puts it, sometimes the smartest systems are the ones you never see. So how close are we to a world where AI is simply part of the background of every business process? And what will it take for companies to trust AI at the infrastructure level rather than the interface? Tech Talks Daily is Sponsored by NordLayer: Get the exclusive Black Friday offer: 28% off NordLayer yearly plans with the coupon code: techdaily-28. Valid until December 10th, 2025. Try it risk-free with a 14-day money-back guarantee.
How Outsourced Accounting Empowers SMBs: Insights from Rhett Molitor, CEO of Basis 365 AccountingIn this episode, host Josh Elledge interviews Rhett Molitor, CEO and co-founder of Basis 365 Accounting, to explore how outsourced accounting is transforming small and mid-sized businesses. Rhett shares how fractional accounting services help companies move beyond simple bookkeeping to strategic financial management. He also discusses how AI and automation are reshaping the accounting landscape and why proactive financial oversight is the key to scaling with confidence.The Shift to Strategic, Outsourced AccountingRhett Molitor founded Basis 365 Accounting in 2012 to fill a crucial gap for businesses earning between $1M–$20M in revenue—companies that have outgrown basic bookkeeping but don't yet need a full-time accounting team. Instead of focusing on compliance alone, Basis 365 partners with CEOs to turn accounting into a growth lever.Molitor breaks accounting into four key levels: bookkeeper, accountant, controller, and CFO—each representing a stage of financial maturity. A proactive approach means using data for decision-making, forecasting cash flow, and improving profitability over time. He also cautions that while AI and automation have made accounting faster, expert human oversight remains essential for accuracy and strategy.For SMB leaders, Rhett's message is clear: don't treat accounting as an afterthought. It's not just about managing expenses—it's about creating visibility, confidence, and insight to drive growth. Partnering with the right fractional accounting team gives businesses access to senior-level expertise without the overhead of full-time hires.About the Rhett MolitorRhett Molitor is the co-founder and CEO of Basis 365 Accounting, a U.S.-based outsourced accounting firm specializing in digital agencies, SaaS companies, and consultancies. With over a decade of experience helping SMBs scale efficiently, Rhett champions proactive, transparent financial management supported by technology and expert insight.About the Basis 365 AccountingBasis 365 Accounting provides outsourced bookkeeping, accounting, and fractional CFO services designed for growth-focused businesses. By combining automation tools with expert financial guidance, Basis 365 helps companies gain clarity, reduce risk, and improve profitability. Learn more at basis365.com.Links Mentioned in This EpisodeBasic 365 Accounting WebRhett Molitor LinkedIn ProfileKey Episode HighlightsThe 4 levels of accounting: bookkeeper, accountant, controller, CFOWhy proactive financial management drives scalabilityHow AI and automation are reshaping accounting workflowsCommon pitfalls SMBs face when they “outgrow” basic bookkeepingActionable steps to make accounting a strategic business advantageConclusionOutsourced accounting isn't just about saving money—it's about gaining visibility, expertise, and strategic advantage. Rhett Molitor's approach at Basis 365 Accounting shows that when SMBs invest in proactive financial systems and fractional expertise, they set the stage for smarter growth and long-term stability.
In this high-energy episode of Mostly Growth, CJ Gustafson, Kyle Poyar, and Ben Hillman dive into the hidden levers of SaaS growth and what truly separates startups that scale to $20M+ ARR from those that stall out. They explore eye-opening data from 6,500 companies, revealing how the best improve net retention, raise pricing, and re-engineer their revenue models over time. Alongside the metrics, there's plenty of playful chaos—like a naming debate over “Yoshinobu Yamamoto Gustafson,” a rapid-fire game of “Founder or Pop Star,” and CJ's accidental IPO embargo break. It's part insight, part inside joke, and 100% for SaaS operators and C-suite climbers.—LINKS:Mostly Metrics: https://www.mostlymetrics.comCJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Growth Unhinged: https://www.growthunhinged.com/Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/Slacker Stuff: https://www.slackerstuff.com/Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/https://www.growthunhinged.com/p/the-compounding-startuphttps://www.growthunhinged.com/p/the-odds-of-making-ithttps://www.superme.ai/kylepoyar?conversationId=VgDXTOl2Z89mW7UYXstU0bhttps://a16z.com/anatomy-of-an-enterprise-platform-company/https://www.investopedia.com/terms/h/hhi.asphttps://navan.com/https://www.mostlymetrics.com/p/navan-ipo-s1-breakdownhttps://x.com/amendandpretend/status/1983588137453416763?s=46https://x.com/ryan_c_walsh/status/1983705182371475630?s=46https://www.reddit.com/r/TwinCities/comments/z6hxp8/how_much_are_people_paying_for_residential_snow/—RELATED EPISODES:Getting fired 4 times made me a founder | Sam Jacobs of Pavilionhttps://youtu.be/8X-JVOF-1A0Why Founders Are Posting Sad Dinnershttps://youtu.be/Zl6NSIHF2Gk—TIMESTAMPS:00:00:00 Preview and Intro00:01:55 Sponsors – Pulley & Metronome00:04:25 Dodgers Banter & Baby Naming00:05:38 Founder or Pop Star Game00:07:50 ChartMogul Data & Growth Levers00:08:30 Expansion, Upsell & Retention Discussion00:15:53 Testing Kyle's AI Avatar00:17:07 CJ's AI Self-Query & Beta Discussion00:18:04 AI Use Cases & Knowledge Retention00:22:03 Platform Debate & A16z Analysis00:24:29 Herfindahl-Hirschman Index Explained00:25:34 Platform Metrics & Valuation Upside00:26:48 CrowdStrike, Datadog & Multi-Product Expansion00:28:13 Core Systems of Record & AI's Impact00:29:49 Business Blunders – Navan IPO & Snowflake CRO00:34:07 Snow Removal Pricing & Insurance Logic00:35:56 Closing Remarks & Credits—SPONSORS:Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That's why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.comPulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: https://pulley.com/mostlymetrics—#MostlyGrowthPodcast #SaaSGrowth #StartupStrategy #B2BTech #RevenueRetention This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com
Thinking about raising capital or selling your SaaS company? Your legal readiness can make or break the deal. In episode #326, Ben Murray breaks down what investors and acquirers look for during due diligence — and why preparing your cap table, contracts, IP, and financial systems at least six months in advance is essential to protect your company's valuation and ensure a smooth process. What You'll Learn Cap Table Management: Why tracking every issued share, option, and agreement matters — and how to avoid “email equity surprises.” IP Protection: The critical role of signed IP assignment agreements for employees, contractors, and vendors. Customer & Vendor Contracts: Why detailed MSAs, renewal clauses, and change-of-control provisions are required for investor confidence. Accounting Readiness: How clean, timely accounting — especially a complete MRR schedule (revenue by customer by month) — helps prove the health of your recurring revenue and ARR growth. Sales Tax Compliance: Why sales tax exposure can derail your exit process. Due Diligence Prep: How to build your data room, organize key documents, and present your SaaS business model with clarity. Why It Matters For Founders: Legal gaps can reduce your valuation multiple and slow down the exit timeline. For CFOs: Solid financial systems and clean documentation protect your cash flow and reputation with investors. For Investors: A well-prepared company signals operational maturity and reduces transaction risk. For Operators: Legal readiness supports strategic growth and prevents “deal fatigue” during M&A or fundraising. Resources Mentioned Ben's Blog Post: “SaaS Legal Readiness Checklist” : https://www.thesaascfo.com/why-legal-readiness-can-make-or-break-your-saas-exit/ SaaS Metrics Foundation Course – Learn how to align your financial reporting and recurring revenue metrics for due diligence success. Upcoming Webinar: “Legal Readiness for SaaS Founders — How to Prepare for an Exit or Raise” (details via newsletter)
The Biz to Biz Podcast with Allen KopelmanGuest: Cindy Gallop – Founder of MakeLoveNotPornPremieres Friday at 6 PM ESTIn this powerful episode, host Allen Kopelman sits down with the legendary entrepreneur and changemaker Cindy Gallop, founder and CEO of MakeLoveNotPorn — a groundbreaking social sex platform redefining how we talk about sex, relationships, and human connection.Cindy shares her journey of building a business that challenges taboos, sparks meaningful conversations, and promotes a more open, healthy, and honest dialogue around intimacy. Beyond that, she dives into her fearless approach to entrepreneurship, disruption, and innovation — and what it takes to stand out and make change happen.
Arun Upadhyay, Serial Entrepreneur & Innovator, SaaS & Wireless Industry Leader, Forbes Council Member and CEO of Wirelo joins Enterprise Radio. Listen to host … Read more The post Growing The Premier B2B Marketplace for the Wireless Industry appeared first on Top Entrepreneurs Podcast | Enterprise Podcast Network.
From the archive: This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant. JiNan Glasgow George has built her career from engineering to patent law and investment by transforming ideas into assets and connecting innovators to the resources they need to make positive impact. She is the CEO and co-founder of Patent Forecast, a business intelligence SaaS company that provides insights for investors and executives, serial entrepreneurs and innovators, giving vision ahead of market data using patent data and AI. Top 3 Value Bombs 1. With imagination and ideas, you have an unlimited resource for solving problems and creating a positive impact in the world, however, most people do not use it. 2. Almost everybody has a trademark to register, copyright, or patent. 3. You can make the most valuable asset in your business from your ideas and transform that into intellectual property, but you have to know how to use it in your industry. NEO IP is an intellectual property law firm with a holistic approach for creating IP assets - NEO IP Sponsors HighLevel - The ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies. Learn more at HighLevelFire.com. The Dealmaker's Will - If you're ready to sharpen your instincts, elevate your mindset, and learn what separates deal-takers from deal-makers. Go grab your copy of The Dealmaker's Will today on Amazon. Quicksilver Scientific - Make advanced liposomal supplements so you can actually feel the difference - energy, focus, calm, recovery. Get 10 percent off plus free shipping at TryQS.com/fire!
Which business model should you start? Get Andrew's cheat sheet with his full ranking and real profit margins here: https://clickhubspot.com/dge Episode 762: What's the best business to start in 2026? Agencies, SaaS, Restaurants, Real Estate, Marketplaces. Angel Investing; Andrew Wilkinson has played every game. He built 38 companies, lost $10 million, and still ended up with a $300 million portfolio. This week, @shaanpuri spoke with him about: the best and worst business models to win in 2026 starting Tiny with just $4M (now $250M) the truth behind the Twitter hate on Tiny's stock why buying companies beats building them His is not a redemption story. It is the unapologetic reality of building, failing, and getting back up. — Show Notes: (0:00) Intro (3:06) MLM (4:28) Freelancer (5:07) Agency (9:33) SaaS (14:48) Restaurant (17:03) Marketplace (19:43) Short Term Rentals (20:52) Content Creator (23:06) Real Estate (26:16) Fund Management (35:21) Local Services (36:36) Investing (38:12) Sweaty Startup (43:15) Tiny stock performance (52:20) The courage to be disliked (1:10:21) Inputs v outputs — Links: • Tiny - https://tiny.com/ • Never Enough - https://www.neverenough.com/ • Serato - https://serato.com/ • Rekordbox - https://rekordbox.com • Pershing Square Holdings - https://pershingsquareholdings.com/ • Invest Like The Best - https://www.youtube.com/@ILTB_Podcast • The Courage To Be Disliked - https://tinyurl.com/5fk3sa79 — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies! Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth • Sam's List - http://samslist.co/ My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano //
The Twenty Minute VC: Venture Capital | Startup Funding | The Pitch
Chad Peets is one of the greatest sales leaders and recruiters of the last 25 years. From 2018 to 2023, Chad was a Managing Director at Sutter Hill Ventures. Chad has worked with the world's best CEOs and CROs to build world-class go-to-market organizations. Chad is currently a member of the Board of Directors for Lacework and Luminary Cloud and on the boards of Clumio and Sigma Computing. He previously served as a board member for Astronomer, Transposit, and others. He was an early-stage investor at Snowflake, Sigma, Observe, Lacework, and Clumio. In Today's Discussion with Chad Peet's We Discuss: 1. You Need a CRO Pre-Product: Why does Chad believe that SaaS companies need a CRO pre-product? Should the founder not be the right person to create the sales playbook? What should the founder look for in their first CRO hire? Does any great CRO really want to go back to an early startup and do it again? 2. What Everyone Gets Wrong in Building Sales Teams: Why are most sales reps not performing? How long does it take for sales teams to ramp? How does this change with PLG and enterprise? What are the benchmarks of good vs great for average sales reps? How do founders and VCs most often hurt their sales teams and performance? 3. How to Build a Hiring Machine: What are the single biggest mistakes people make when hiring sales reps and teams? Are sales people money motivated? How to create comp plans that incentivise and align? Why does Chad believe that any sales rep that does not want to be in the office, is not putting their career and development first? Why is it harder than ever to recruit great sales leaders today? 4. Lessons from Scaling Sales at Snowflake: What are the single biggest lessons of what worked from scaling Snowflake's sales team? What did not work? What would he do differently with the team again? What did Snowflake teach Chad about success and culture and how they interplay together?
#663 Most entrepreneurs talk about starting businesses — but what about buying or selling them? In this episode, host Kirsten Tyrrel sits down with Blake Hutchison, CEO of Flippa, the world's leading marketplace for buying and selling online businesses. Blake explains how Flippa helps everyday entrepreneurs find liquidity and buyers for digital assets like Shopify stores, Amazon FBA brands, blogs, SaaS tools, and even YouTube channels. He shares how to know when it's time to sell, what makes a business attractive to buyers, and why most founders underestimate the value of what they've built. From exit psychology to real-world success stories, this episode opens up a whole new way to think about entrepreneurship — one where ownership and exits are no longer reserved for the 1%! What we discuss with Blake: + What Flippa is and how it works + Buying and selling online businesses + Common types of digital assets sold + Why most entrepreneurs overlook exits + Steps to prepare a business for sale + How to value and price your business + Real success stories from Flippa users + Importance of consistency and documentation + The psychology behind selling a business + Flippa's tools and AI-powered valuation system Thank you, Blake! Check out Flippa at Flippa.com. To get access to our FREE Business Training course go to MillionaireUniversity.com/training. And follow us on: Instagram Facebook Tik Tok Youtube Twitter To get exclusive offers mentioned in this episode and to support the show, visit millionaireuniversity.com/sponsors. Want to hear from more incredible entrepreneurs? Check out all of our interviews here! Learn more about your ad choices. Visit megaphone.fm/adchoices
In this episode of Crazy Wisdom, host Stewart Alsop sits down with Harry McKay Roper, founder of Imaginary Space, for a wide-ranging conversation on space mining, AI-driven software, crypto's incorruptible potential, and the raw entrepreneurial energy coming out of Argentina. They explore how technologies like Anthropic's Claude 4.5, programmable crypto protocols, and autonomous agents are reshaping economics, coding, and even law. Harry also shares his experiences building in Buenos Aires and why hunger and resilience define the city's creative spirit. You can find Harry online at YouTube, Twitter, or Instagram under @HarryMcKayRoper.Check out this GPT we trained on the conversationTimestamps00:00 – Stewart Alsop welcomes Harry McKay Roper from Imaginary Space and they jump straight into space mining, Helium-3, and asteroid gold. 05:00 – They explore how Bitcoin could hold value when space mining floods markets and discuss China, America, and global geopolitics. 10:00 – Conversation shifts to Argentina, its economic scars, cultural resilience, and overrepresentation in startups and crypto. 15:00 – Harry reflects on living in Buenos Aires, poverty, and the city's constant hustle and creative movement. 20:00 – The focus turns to AI, Claude 4.5, and the rise of autonomous droids and software-building agents. 25:00 – They discuss the collapse of SaaS, internal tools, and Harry's experiments with AI-generated code and new workflows. 30:00 – Stewart compares China's industry to America's software economy, and Harry points to AI, crypto, and space as frontier markets. 35:00 – Talk moves to crypto regulation, uncorruptible judges, and blockchain systems like Kleros. 40:00 – They debate AI consciousness, embodiment, and whether a robot could meditate. 45:00 – The episode closes with thoughts on free will, universal verifiers, and a playful prediction market bet on autonomous software.Key InsightsSpace and Economics Are Colliding – Harry McKay Roper opens with the idea that space mining will fundamentally reshape Earth's economy. The discovery of asteroids rich in gold and other minerals highlights how our notions of scarcity could collapse once space resources become accessible, potentially destroying the terrestrial gold economy and forcing humanity to redefine value itself.Bitcoin as the New Standard of Value – The conversation naturally ties this to Bitcoin's finite nature. Stewart Alsop and Harry discuss how the flood of extraterrestrial gold could render traditional stores of value meaningless, while Bitcoin's coded scarcity could make it the only incorruptible measure of worth in a future of infinite resources.China and the U.S. in Industrial Tug-of-War – They unpack the geopolitical tension between China's industrial dominance and America's financial hegemony. Harry argues the U.S. is waking up from decades of outsourcing, driven by China's speed in robotics and infrastructure. This dynamic competition, he says, is good—it forces America to build again.Argentina's Culture of Hunger and Resilience – Living in Buenos Aires reshaped Harry's understanding of ambition. He contrasts Argentina's hunger to survive and create with the complacency of wealthier nations, calling the Argentine spirit one of “movement.” Despite poverty, the city's creative drive and humor make it a living example of resilience in scarcity.AI Is Making Custom Software Instant – Harry describes how Claude 4.5 and new AI coding tools like Lovable, Cursor, and GPT Engineer make building internal tools trivial. Instead of using SaaS products, companies can now generate bespoke software in minutes with natural language, signaling the end of traditional software development cycles.Crypto and AI Will Merge Into Incorruptible Systems – Harry envisions AI agents on-chain acting as unbiased judges or administrators, removing human corruption from law and governance. Real-world tools like Kleros, founded by an Argentine, already hint at this coming era of algorithmic justice and decentralized decision-making.Consciousness and the Limits of AI – The episode closes on a philosophical note: can a robot meditate or clear its mind? Stewart and Harry question whether AI could ever experience consciousness or free will, suggesting that while AI may mimic thought, the uniquely subjective and embodied nature of human awareness remains beyond automation—for now.
In this episode of Defender Fridays, LimaCharlie Founder Maxime Lamothe-Brassard talks to Julie Agnes Sparks, Security Engineer at Datadog, about how to maximize logging visibility for effective detection engineering.Julie has a passion for continuous learning, proactively detecting significant security events, and responding effectively. Interests include: diversity & inclusion, privacy, and making technology more accessible.Join the Defender Fridays community, live every Friday, to discuss the dynamic world of information security in a collaborative space with seasoned professionals.Support our show by sharing your favorite episodes with a friend, subscribe, give us a rating or leave a comment on your podcast platform. This podcast is brought to you by LimaCharlie, maker of the SecOps Cloud Platform, infrastructure for SecOps where everything is built API first. Scale with confidence as your business grows. Start today for free at limacharlie.io.
Natalie Barbu is the founder and CEO of Rella, a SaaS platform built to streamline collaboration and workflows for social media teams and agencies. She began as a YouTube creator, grew a following of over 300,000, and then identified the fragmentation of the creator tools market — which led her to build Rella 1.0. With some small seed funding, the first Rella version focused on content creators and made no revenue with a freemium model. With $25K in the bank and no revenue, the four cofounders thought they would shut it down. But a viral video focused on social media teams immediately created paid users and revenue for a new Rella product. "Rella 2.0" now offers all-in-one content planning, scheduling, collaboration boards, billing & analytics, an AI content strategist, and all in one workspace — for social media teams. In just 12 months, they went from having no revenue, no funding, and a hard pivot relaunch to almost $3M in ARR run-rate revenue — with only four co-founder employees. Key Takeaways Charge Early: They learned the hard way that free users don't convert — monetization early was non-negotiable. Lean Teams Win: A small, focused team aligned tightly with a mission beats trying to scale prematurely. Community Is Fuel: Natalie shared behind-the-scenes of the product with early users — built trust + word-of-mouth. Pivot Smart: They transitioned from creator workflow tools to a full SaaS platform after validating demand. This Interview Is Perfect For SaaS founders pivoting after a stalled product Founders learning how to find product-market fit Teams deciding when to hire or stay lean Builders designing tools for marketing and content teams Quote from Natalie Barbu, founder and CEO of Rella "It was about two years before we decided to pay ourselves. I was still making money from my social media. So that's how I supported myself. And then my co-founders had to find side things, which I know a lot of people say, you have to be a hundred percent all in and invested in it. "But when you're not making money, you need to find a way to support yourself. So yeah, they had some side gigs that they were working on while still working full-time on Rella. "Once we started making more money with Rella 2.0, we all bumped ourselves up and got some raises since we could afford it, which has been such an accomplishment. It's money that we're actually making from our customers and our users and the income that we're generating." Links Natalie Barbu on LinkedIn Rella on LinkedIn Rella website - Use this 10% Discount Code for Rella - practical Podcast Sponsor – Cypress Growth Capital This podcast is sponsored by Cypress Growth Capital, an alternative to equity, royalty-based growth capital provides funding in exchange for a fixed percentage of your company's future monthly revenues. Learn more at https://www.cypressgrowthcapital.com/ The Practical Founders Podcast Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel. Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com. Practical Founders CEO Peer Groups Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.
In this episode of Chaos to Clarity, Eric Weiss sits down with Gaurav Agarwal, COO of ClickUp, to unpack how one of San Diego's biggest SaaS success stories built a $300M ARR business by putting product, speed, and customer obsession at the center of its strategy.Gaurav shares how ClickUp redefined product-led growth, balanced self-serve and sales-assisted revenue models, and built a culture obsessed with iteration and feedback. From eliminating “work about work” to running 100+ experiments per week, this conversation is a masterclass in operational excellence and founder discipline.In This Episode:How ClickUp grew to $300M ARR from San Diego The real meaning of product-led growth (and why it's misunderstood) Finding the line between free and paid features How to build a customer-obsessed culture Running 100+ experiments per week without chaos The secret to scaling operations without killing innovation Gaurav's leadership framework: business first, team second, self third Key Quote:“Our speed is our secret weapon. You can't think your way to success — you have to ship, learn, and iterate relentlessly.”
In this episode of Cloud Wars Live, Bob Evans speaks with T.K. Anand, Executive Vice President at Oracle, during Oracle AI World in Las Vegas. The discussion centers on Oracle's new AI Data Platform, a major initiative designed to help customers harness their own data to drive AI transformation. Anand outlines how Oracle's open, unified approach to managing enterprise data enables organizations to bring AI directly to their business processes, while also citing breakthrough developments in industry-specific applications.Reinventing with AIThe Big Themes:Data + AI = Business Reinvention: Enterprises cannot simply adopt AI as a bolt‑on; they must combine their private business data — workflows, applications, processes — with advanced models if they hope to reinvent themselves ahead of disruption. Anand notes that many AI/LLMs have been trained on public domain data and thus “know nothing about our customers' private data.” The AI Data Platform is designed to enable that union.Pre‑integrated with SaaS Applications: For customers of Oracle's large SaaS portfolio (e.g., Fusion, NetSuite, industry apps) the AI Data Platform offers tailored variants that are pre‑integrated with the application's data models and semantics. This means organizations get out‑of‑the-box predictive models, analytics, and agents aligned to their workflows, but still have the full platform underneath to extend or customize. This helps reduce time‑to‑value for companies using those applications.Full Stack Advantage: Oracle positions its differentiator as owning and integrating the full stack: cloud infrastructure (OCI including autonomous database), data and analytics platform, applications (SaaS) and now AI/agents. This end‑to‑end control enables closer integration between data assets, applications, and AI use cases. For example, having application workflow knowledge baked into the data platform allows faster mapping from business process to predictive agent.The Big Quote: “The AI Platform is all about helping our customers achieve AI transformation through the power of their own data."More from T.K. Anand and Oracle:Connect with T.K. Anand on LinkedIn or get an overview of Oracle AI Data Platform. Visit Cloud Wars for more.
Nightfall AI is pioneering AI-native data loss prevention (DLP) for enterprises navigating cloud, SaaS, and AI application proliferation. Founded in 2017 by former Uber engineers who witnessed data breaches firsthand, Nightfall addresses the architectural limitations and false positive problems plaguing legacy DLP solutions. By leveraging machine learning and large language models across three distinct layers—content classification, risk assessment, and forensic investigation—Nightfall delivers 10x accuracy improvements while enabling secure AI adoption. In this episode of Category Visionaries, I sat down with Rohan Sathe, Co-Founder & CEO of Nightfall AI, to explore their strategy for displacing entrenched incumbents and positioning as the security enabler for organizational AI deployment. Topics Discussed: Nightfall's founding thesis addressing DLP coverage gaps created by cloud and SaaS migration Three-layer AI architecture: content classification, behavioral risk analysis, and agent-assisted forensics Positioning against legacy DLP's rules-based approaches and exact data match workarounds Market education shift post-ChatGPT: from "don't use AI" to "enable AI securely" Purple brand differentiation strategy in security's dark-themed visual landscape Conference ROI reallocation: executive suite meetings versus booth presence at RSA and Black Hat Mid-market to enterprise expansion pattern through peer-to-peer word-of-mouth Founder-led LinkedIn strategy balancing market education with competitive displacement narratives Sales team composition: domain practitioners versus traditional sales profiles GTM Lessons For B2B Founders: Structure POVs to prove quantifiable superiority on one dimension: Rohan revealed Nightfall benchmarks against Google and Microsoft DLP APIs, demonstrating 10x accuracy improvements during proof-of-value cycles. When challenging mature categories, identify the single metric where you demonstrably outperform and architect evaluations to surface that gap. The key isn't claiming superiority—it's creating controlled comparisons where buyers verify it themselves. Deploy AI across three workflow layers, not as a monolithic feature: Nightfall applies AI distinctly at content classification (identifying sensitive data with high precision), behavioral analysis (distinguishing risky data movement from standard workflows), and investigation assistance (helping analysts focus forensic efforts). This creates compounding value and defensibility. Map where AI can reduce friction at multiple decision points in your customer's workflow rather than treating it as a single capability. Replace field marketing spend with curated CISO access: Nightfall redirected budget from RSA and Black Hat booths to private suites hosting scheduled executive meetings. Rohan emphasized engaging "chief information security officers who sign the checks" in intimate settings rather than booth traffic. For enterprise sales, calculate cost-per-meeting with economic buyers and reallocate spend accordingly. Design 8-person dinners as vendor-neutral industry forums: Nightfall hosts 3-4 annual dinners with 5-7 prospects and 2-3 team members (founders, head of product) structured around industry developments—like OpenAI's agent workflow builder and security implications—not product pitches. The format positions Nightfall as thought leaders while qualifying prospects through discussion quality. Agenda topics, not sales decks, drive conversion. Hire former practitioners into quota-carrying roles: Rohan identified hiring former DLP security operations analysts as account executives or solutions architects, mirroring trends in legal tech (hiring lawyers) and HR tech (hiring recruiters). For technical categories with sophisticated buyers, domain fluency in customer-facing roles outweighs traditional sales experience. This isn't solutions engineering—it's putting practitioners in quota-carrying positions. Use LinkedIn for two narratives: market education and competitive wins: Rohan posts thought leadership on DLP evolution and AI security implications alongside selective announcements of competitive displacements at enterprise AI companies and top 10 banks. He noted role postings also drive engagement, signaling growth momentum. The pattern: educate on category gaps, prove you're winning deals in those gaps, show team expansion. Avoid pure product promotion. Leverage AI adoption mandates as your demand generation engine: Post-ChatGPT, Rohan noted "board mandate and CEO mandate from every company to use as much AI as you can" created new security requirements. Nightfall shifted positioning from "prevent data loss" to "enable AI adoption securely." When macro shifts create executive-level mandates in your category, realign messaging around enabling that mandate rather than preventing its risks. Challenge category conventions through education, not assertion: Rather than simply claiming exact data match (EDM) is obsolete, Nightfall explains EDM emerged as a workaround for rules-based approaches' false positive problems—and ML eliminates the need for workarounds entirely. When displacing established practices, reveal why current solutions exist (what problem they patch) before explaining why your approach eliminates the underlying issue. // Sponsors: Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don't Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM
Register for Founder University Japan's kickoff! https://luma.com/cm0x90mkToday's show:*On TWiST, Jason welcomes an all-star VC panel — Deedy Das of Menlo Partners and Jay Eum of GFT Ventures — for a deep dive into the shocking scale of early-stage AI raises, a transitional moment for investors, the growing importance of the “prosumer” market, ChatGPT's insane smile curves, and much much more.IN THIS EPISODEWhat the panelists make of Roelof Botha's exit from Sequoia… and is he really going anywhere…Why Jason says VC is no longer the best way to get rich…Why so many private companies are growing SO HUGE before going public…And much more!Timestamps:(00:03:37) Jason is fresh from surviving Riyadh traffic but he's here and introducing our all star panel(00:04:03) Why Jason compares Riyadh to Silicon Valley in the 1960s(00:05:21) Friend of the Pod Roelof Botha is stepping down at Sequoia… our insiders try to guess what might have happened…(10:00) Crusoe - Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit crusoe.ai/startup to reserve your capacity for the latest GPUs today.(00:13:11) Deedy moved up at Menlo without being a venture native… he shares the secrets behind his rise.(00:19:09) Was Roelof wrong about “return-free risk”? Does more capital always = more great companies?(20:00) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(00:26:54) With so many private companies growing SO HUGE… when is the right time to go public? Considering the case of Glean and Stripe…(30:00) AWS Marketplace - If you're ready to really accelerate your sales cycle, AWS Marketplace is your next stop. Head to https://aws.com/startups to learn more.(00:30:07) Why Jason says venture capital is no longer the best way to get rich(00:32:34) Why AI apps are so appealing to enterprises after years of paying for SaaS(00:36:32) The growing importance of “prosumers”(00:37:31) Why Deedy says a smile curve is the most beautiful depiction of “Product Market Fit”(00:44:36) Why it's still tough to raise pre-seed money, even during an AI “boom”!(00:46:08) Why Jason says the hardest job in the tech ecosystem is being an investor(00:55:52) “Time is one of the primary drivers of venture capital return.” - Jay Eun(00:57:42) Deedy on the shocking amounts being raised by early-stage AI companies(01:00:21) Just how much DO VCs work compared to founders? The panel compares notes.(01:02:53) Are some investors not doing diligence? Deedy on the speed of some AI deals.(01:16:51) The panel picks their fav portfolio company of the moment (or one of their faves)Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comFollow Alex:X: https://x.com/alexLinkedIn: https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisThank you to our partners:Crusoe - Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit crusoe.ai/startup to reserve your capacity for the latest GPUs today.Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visitAWS Marketplace - If you're ready to really accelerate your sales cycle, AWS Marketplace is your next stop. Head to https://aws.com/startups to learn more.Check out Jason's suite of newsletters: https://substack.com/@calacanisFollow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
In this episode, we talk about whether Rick's expertise with traditional inbound marketing will work for LegUp Health.
On this episode of WP Builds, Natalie MacLees joins Nathan Wrigley to talk about the new accessibility tool, Aaardvark Accessibility. They discuss Natalie's background in web accessibility, the evolution and importance of accessible web design, and how their SaaS platform helps agencies and developers find, fix, and monitor accessibility issues across client websites. The conversation also covers practical and moral reasons for improving accessibility, details about automated and manual testing, reporting features, explanations in plain English, and pricing plans.
In this live SocialNext Toronto 2025 conversation, guest host Maddie Alvarez sits down with Joe Teo, founder and CEO of HeyOrca!, the Canadian-built social media platform helping thousands of agencies and teams simplify their content workflows.From dad jokes to dashboards, Joe shares why the point of social media isn't virality—it's community. He unpacks how HeyOrca's product philosophy puts collaboration first, what social media managers actually need in 2025, and how AI can support (not replace) the humans behind the posts.You'll hear Joe's take on why strong communities require intentional moderation, how brands can create digital “gardens,” and why the best social spaces are both safe and self-sustaining.
OpenAI: reportedly losing $12 billion a quarter.