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SaaStr Podcasts

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The Official SaaStr Podcast is the latest and greatest from the world of SaaStr, interviewing the most prominent operators and investors to discover their tips, tactics and strategies to attain success in the fiercely competitive world of SaaS. On the side of the operators, we center around getting from $0 to $100m ARR faster, what it takes to scale successfully and what are the core elements of hiring. As for the investors, we learn what metrics they hone in on when examining SaaS business, ...
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The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
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Heresy

Dimitar Stanimiroff

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Thinkers. Builders. Rebels. Big ideas from the edge of tech and beyond. Hosted by Dimitar Stanimiroff, Heresy started with a simple goal: learn from the sharpest minds in SaaS GTM. It’s grown into a show that follows curiosity across domains—tech, startups, investing, science, and philosophy. Past guests include Jason Lemkin (SaaStr), Aaron Ross (Predictable Revenue), Philip Su (ex-Meta, OpenAI) and execs from Uber, Box, Twilio, and Stack Overflow. New episodes drop regularly.
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Learning Machine

Content and Coffee

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This is Learning Machine. A podcast about digital marketing, content, strategy, startups, and business. If you like Mixergy, Entrepreneur on Fire, Tropical MBA, Rocketship.fm, SaaStr, Tim Ferriss show, or Startups for the Rest of Us, you will love Content and Coffee.
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Cloud Returns covers ALL types of software investing, whether seed, venture capital, growth equity, private equity, debt, and the public markets. Our target audience: SaaS investors AND operators raising capital that listen to SaaStr, Twenty Minute VC (20VC), The Logan Bartlett Show, or Thoma Bravo’s Behind the Deal and still want to learn even more.
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SaaS Marketing Superstars is the show where we uncover proven growth strategies from CMOs and marketing leaders behind some of the fastest-growing SaaS companies.Each episode features an interview with a SaaS CMO, Founder or marketer leader, discussing topics like paid ads, SEO, content marketing, ABM and sales, landing page optimization, email marketing and how to use these strategies to generate more trial and demo signups for your SaaS.
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Made for "full stack" cloud operators, Cloud Radio covers all aspects of the business of software. Our target audience: SaaS investors that listen to SaaStr, The SaaS Podcast, SaaS Revolution, or Startups For The Rest Of Us and still want to learn even more.
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A show for CEO's, CMO's CRO's and Venture Capitalists If you are in a B2B Leadership role this is the podcast for you. The founder of "The Brutal Truth About Sales & Selling" interviews the most thought-provoking guests. We will cover what is working today in Sales & Marketing. If you like Tim Ferriss, Bill Burr, Dave Ramsey, Serial, Reply All, The Art of Charm, HBR, WTF, Startup, Motley Fool, Money, Gimlet, TEDTalk, NPR, EOFIRE, The TOP, Ziglar, Hustler, Advanced Selling, Salesman Red, Sale ...
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Join Christopher as he navigates the diverse intersection of business, technology, and the human experience. And, to be clear, the purpose isn’t just to explore technologies but to unravel the profound ways these tech advancements are reshaping our lives, work, and interactions. We dive into the heart of digital transformation, the human side of tech evolution, and the synchronization that drives innovation and business success. Also, be sure to check out my Substack for weekly, digestible r ...
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The Longcut breaks down the illusion of the overnight success by sharing the stories of those who have successfully created, launched, and grown software businesses to solve a problem. In the fiercely competitive world of SaaS, Ryan introduces you to the brilliant minds behind the businesses we admire. You’ll hear perils and pitfalls, stories of staggering success, candid conversations, and what drives these owners, entrepreneurs, and innovators forward. Key themes we’ll explore include prod ...
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B2B Revenue Leadership - CEO, CRO, CMO, VC, Sales and Marketing Startup SaaS

Sales Leadership Marketing Startup SaaS expert - Brian Burns

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If you're interested in B2B Revenue Leadership this is the show for you. From the founder of The Brutal Truth about Sales & Selling and The Sales Questions PodCast. This PodCast is Focused on Leadership in the B2B Space to drive revenue by using the most modern and scientific approaches. If you are a CEO, VC, CRO, CMO or want to be one some day this PodCast is for you. If you like Tim Ferriss, Bill Burr, Dave Ramsey, Serial, Reply All, The Art of Charm, HBR, WTF, Startup, Motley Fool, Money, ...
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Angles and Insight

Casey Hill and Danny McCarthy

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This show pairs up 2 leaders in the tech world to face off on specific issues from differing perspectives. Through these debates, we aim to shatter the echo chambers and help you build winning strategies for your team in fast-changing times.
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Breaking down the divide in modern day SaaS sales culture by having REAL and HONEST conversations with all levels of the power line. Fixing the broken SDR/BDR system one episode at a time. The show by an SDR... for SDR’s. Discussing the sales topics that you care about. Brought to you by ABUVEGROUND
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We are only one week into 2026, and the "AI Takeover" headlines are in full swing. While half the internet cheers the efficiency of replacing humans with agents, the other half is screaming about the problems it creates. However, as leaders, we can’t afford to react with outrage. We have to react with strategy. This week, I’m putting the recent Saa…
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SaaStr 836: The Step-By-Step Playbook for Building AI-Powered GTM Teams with Personio's CRO Philip Lacor, CRO of Personio, shares his company's journey to building an AI-powered go-to-market motion, including 5 critical lessons learned and 4 real-world use cases delivering measurable results. In this podcast, Philip breaks down: ✅ The 5 lessons for…
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Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new op…
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Can your 9-to-5 job secretly prepare you to be a founder? In this solo episode, Rob Walling shares 11 unexpected lessons from his own day jobs, from courier to electrician to engineering manager, and how each role quietly taught him skills that shaped his success as a SaaS founder. He dives into the value of curiosity, self-education, and learning …
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Aishwarya Naresh Reganti and Kiriti Badam have helped build and launch more than 50 enterprise AI products across companies like OpenAI, Google, Amazon, and Databricks. Based on these experiences, they’ve developed a small set of best practices for building and scaling successful AI products. The goal of this conversation is to save you and your te…
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We have officially woken up from the "AI Hangover" of 2025. As we kick off 2026, the initial razzle-dazzle of generative AI has faded, and we are left staring at the reality of integration, accountability, and the messy human reaction to it all. This episode is a deviation from my standard weekly news rundown. Instead of chasing headlines, I’m plan…
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What’s it take for a bootstrapped SaaS to beat a competitor with $10M in venture funding? In this episode, Rob Walling talks with Laura Roeder, founder of Paperbell, about how her lean, fully-bootstrapped team outlasted and outperformed a VC-funded rival. They discuss what the venture-backed company got wrong, how Paperbell focused on the right cus…
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2025 was the year of, "Buy more, go faster, and worry about the fallout later." We put the innovation agenda on the company credit card. But as we enter 2026, the music has stopped, the lights have come on, and the tab is coming due. This week, I’m declassifying what I call the "AI Hangover." Many headlines continue screaming about the next model r…
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Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models f…
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SaaStr 835: AI + B2B in 2026: Find the Tailwinds or Get Left Behind with SaaStr CEO and Founder Jason Lemkin Software spend is set to hit record levels in 2026, but you're not getting any of it unless you change. SaaStr CEO and Founder Jason Lemkin breaks down the paradox facing B2B companies right now: It's never been easier to scale to $100M (for…
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How will AI, SEO, and market shifts change SaaS next year? In this solo episode, Rob Walling revisits his predictions for 2025, what he got right, what he totally missed and shares nine new predictions for 2026. He reflects on trends shaping bootstrapped SaaS, from the rise of AI-first startups to the challenges facing horizontal SaaS founders. Int…
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Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion. We discuss: 1. Why “extraordinary results demand extraordinary efforts” 2. Why you should deliberately understaff projects, and how to know when you’ve gone too far 3. Matt’s transition from COO to CPO …
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SaaStr 834: Why OpenAI Doesn't Pay Sales Commission (And Why It Works) with OpenAI GTM Leader Maggie Hott, and Harry Stebbings, Founder of 20VC Discover how OpenAI's unique approach to B2B sales compensation is changing the game. In this interview with Harry Stebbings, Founder of 20VC, Maggie Hott, OpenAI GTM leadership, shares her experience at Op…
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After funding 210+ B2B SaaS companies, what patterns have emerged? In this episode, Rob Walling shares the 2025 State of TinySeed, from its first fund in 2018 to a global portfolio of over 210 B2B SaaS companies. He reflects on TinySeed’s growth, what the data reveals about today’s founders, funding trends, and the rise of AI-first startups. Topics…
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There’s a narrative that "nobody knows the future," and while that’s true, every January we’re flooded with experts claiming they do. Back at the start of the year, I resisted the urge to add to the noise with wild guesses and instead published 10 "Realistic Predictions" for 2025. For the final episode of the year, I’m doing something different. In…
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Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering and ran the first-ever prompt injection competition, working with top AI labs and companies. His dataset is now used by Fortune 500 companies to benchmark their AI systems security, he’s s…
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Elena Verna is the head of growth at Lovable, the leading AI-powered app builder that hit $200 million in annual recurring revenue in under a year with just 100 employees. In this record fourth appearance on the podcast, Elena shares how the traditional growth playbook has been completely rewritten for AI companies. She explains why Lovable focuses…
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2023 broke the old rules of go-to-market. AI isn’t just changing the tools — it’s rewriting the entire playbook, and most GTM leaders are already behind. In this episode, I sit down with Sam Jacobs, founder of Pavilion, to unpack the seismic shifts shaking SaaS leadership: Why growth has never been harder — even at top-tier tech companies The comin…
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SaaStr 833: AI and the Death of the 2021 Sales Playbook with SaaStr CEO and Founder Jason Lemkin Join SaaStr CEO and Founder Jason Lemkin from SaaStr London as we tackle pressing topics in AI and sales during an engaging AMA session. From discussing the evolution of inbound vs. outbound sales to detailing the transformative impact of AI on sales ro…
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How do you step back from daily decisions without losing control of your SaaS? In this episode, Rob Walling answers listener questions about when to delegate key founder skills, whether great founders can succeed with any idea, and the limits of no-code or “vibe-coded” apps. To help answer one question, he calls up Ruben Gamez to get his insights o…
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There’s a narrative we’ve been sold all year: "Move fast and break things." But a new 100-page report from the Future of Life Institute (FLI) suggests that what we actually broke might be the brakes. This week, the "Winter 2025 AI Safety Index" dropped, and the grades are alarming. Major players like OpenAI and Anthropic are barely scraping by with…
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Alexander Embiricos leads product on Codex, OpenAI’s powerful coding agent, which has grown 20x since August and now serves trillions of tokens weekly. Before joining OpenAI, Alexander spent five years building a pair programming product for engineers. He now works at the frontier of AI-led software development, building what he describes as a soft…
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SaaStr 832: How to Use AI to Hyper-Customize Go-To-Market at Scale with SaaStr's CEO and Chief AI Officer In this episode from SaaStr AI London 2025, SaaStr CEO and Founder Jason Lemkin and SaaStr's Chief AI Officer, Amelia Lerutte discuss the implementation and optimization of AI SDRs within various business contexts. They focus on key AI agents u…
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How much design polish is really enough? In this episode, Rob Walling is joined by fan favorite Derrick Reimer for a new round of listener questions. They dig into the best AI coding stacks right now, how to ship fast without losing polish, whether AI is changing the kind of risk founders face, and when to start taking security seriously. Episode S…
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