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On Mondays, Jon Stewart hosts The Daily Show, but on Thursdays, he's back in your ears with The Weekly Show -- a podcast featuring in-depth conversations with a range of special guests. From experts and advocates, to stakeholders and thought leaders, we discuss the challenges, changes, and ideas that are shaping our world.
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Sales Players

Sales Players, LLC

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The #1 resource for top players in Tech Startup Sales. Hosted by Jesse Woodbury, an expert in early-stage startup selling, Sales Players features weekly, actionable ideas for reps, founders, and operators by exploring the mindset, skills, and tools high performers use to generate pipeline, close deals, and build wealth in Tech Sales.
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Fund/Build/Scale

Walter Thompson

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After working for years in early-stage startups and as a journalist, here are three hard truths I’ve learned: 1. Success in Silicon Valley hinges on connections, hard work and luck. 2. Startups often fail because founders lack fundamental business knowledge. 3. Real, actionable advice comes from those who’ve actually done it. There’s no such thing as “founder DNA.” If you’re willing to take on risk and invest years of your life in something that has maybe a 10% chance of paying off — less if ...
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Blockchain Bridge

Ben Arnon and Jay Kolbe

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Blockchain technology is transformative, disruptive and has the potential to redefine business and propel humanity into the decentralized future. It is also complex, confusing, and only fully understood by a tiny subset of the world’s population. In this podcast, hosts Ben Arnon and Jay Kolbe speak with leading experts - both within and outside of the blockchain industry - who will help make sense of this emerging technology. Conversations focus on tangible examples of blockchain’s impact on ...
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I am your trusted resource for educational content on individual stock analysis. My mission is to help listeners enhance their ability to analyze stocks independently, identify deeply undervalued opportunities, and explore securities that may be overlooked by the broader investing public. _______________________________________________________________________________________________________________________________________________________________________ What the Podcast Offers: On-the-Ground ...
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show series
 
With the US now directly engaged in the Israel-Iran conflict, Jon is joined by Maziar Bahari, publisher of iranwire.com and author of “Then They Came for Me,” a memoir that served as the basis for Jon’s 2014 film “Rosewater.” Together, they explore the reality of life under Iran's current government, discuss the complex challenges of regime change …
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Uncork Capital Partner Amy Saper shares practical advice for early-stage founders building AI-enabled tools for engineering, product, and design teams, or as she describes them, "products that make you not want to quit your job." Drawing on her experience in product marketing at Twitter, Uber, and Stripe, she explains why storytelling is an underra…
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Ten Eleven Ventures CTO and Operating Partner Scott Lundgren shares practical advice for early-stage cybersecurity founders. He explains why founder-market fit matters more than product polish, how teams should think about TAM in fragmented markets, and the signals he looks for in technical pitches. He also breaks down how Ten Eleven’s network help…
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Jesse shares 20 proven sales plays he turns to when deals stall, pipeline dries up, or nothing seems to be working. These are high-leverage, momentum-building activities that have helped him bounce back from slumps and close big deals. EPISODE LINKS: • https://www.salesplayers.co/posts/20-high-leverage-sales-activities CONNECT WITH JESSE: • LinkedI…
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Construction workers spend hours on their hands and knees snapping chalk lines to mark where walls, plumbing and utilities should go. It’s painstaking, back-breaking labor. And that’s how it’s been done for centuries. Tessa Lau saw an opportunity — and built a robot that does it faster, safer, and with surgical precision. In this episode of Fund/Bu…
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Amid growing fears about where the Israel-Iran conflict leads, Jon is joined by Ben Rhodes, co-host of "Pod Save the World" and former Deputy National Security Advisor, and Christiane Amanpour, CNN's Chief International Anchor and host of "Christiane and The Ex Files with Jamie Rubin." Together, they trace the complex history that brought us to thi…
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In this episode, Dale defines what he looks for in a perfect stock: 1. A business with five low cyclically adjusted ratios. 2. A business with low competition, several clients, not capital intensive. 3. A business with a solid management team. Verbal disclosures read from 0:16 - 1:21 . General information and full disclosures for Dale’s Solo Invest…
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Jesse (who is not giving financial or investment advice) shares why tech sellers have a huge advantage when it comes to building wealth and financial security. He shares a few things you can do to develop financial security which will enhance your selling career. CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodbury/ • Website: …
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What happens when a team of legal veterans decides to rebuild the dispute resolution process from the ground up? To find out, I interviewed Rich Lee, co-founder and CEO of New Era ADR, a platform designed to resolve legal disputes faster, at lower cost, and with less friction for both companies and individuals. We talked about building a team that …
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This week, with the military deployed to LA and readying to parade in DC, Jon is joined by Jill Lepore, Professor of History and Law at Harvard University, and Kevin M. Kruse, Professor of History at Princeton University. Together, they consider what history reveals about moments when presidential power tests democratic limits, and discuss ways tha…
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Jesse sits down with "Fidel Cache Flow," an anonymous tech seller who’s built a cult following on Sales Twitter with unfiltered takes on career growth, wifi money, and escaping the W2 grind. Fidel runs Desperados, a fast-growing private community for sellers looking to build income beyond quota. In this episode, they dive into contract stacking, vi…
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Before Postman became a category-defining platform used by millions of developers, it was a personal side project. In this episode, co-founder and CEO Abhinav Asthana shares how he went from hacking on API tools in Bangalore to leading a global company with nearly 900 employees across three continents. We talk about: Building a developer-first prod…
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Jesse breaks down 23 hard-earned truths about enterprise sales that every seller should know SPONSORS: • ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp EPISODE LINKS: • Read the 23 Truths: https://www.salesplayers.co/posts/23-absolute-truths-about-enterprise-selling • Book FREE 1:1 Coaching …
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The best candidates don’t just show up, they sell themselves at every step. In this episode, Jesse shares the high-leverage interview plays that get offers in today’s brutal job market. SPONSORS: • ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp EPISODE LINKS: • Join the FREE Sales Players Sl…
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With the Trump administration generating headlines at breakneck speed, Jon is joined by CNN's Kaitlan Collins, anchor of "The Source with Kaitlan Collins" and Chief White House Correspondent. Together, they examine how to cut through the noise and ask the right questions, discuss the ins and outs of covering the White House, and explore what goes i…
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Jesse breaks down the 10 traits that separate good reps from top-performing enterprise and mid-market sellers. After a decade in tech sales and five years interviewing the best in the game, he shares what it really takes to sell at the highest level. SPONSORS: • ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://tr…
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When Tony Stubblebine took over as CEO of Medium in 2022, the platform was burning $2.5 million a month, bleeding subscribers, and was overrun with content that left founder Evan Williams cringing. Tony pitched Ev a turnaround built on small teams with access to data, customers, and the freedom to rebuild Medium like a startup from the inside out. …
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Jesse shares the unfiltered story of his time as the founding AE at a seed-stage startup. From landing the role on a mountain bike trail to building sales ops from scratch, it's a raw look at what early-stage startup life is really like. SPONSORS: • ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.co…
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Rachel Springate is the founding general partner of Muse Capital, an early-stage venture fund focused on overlooked sectors like women’s health, wellness, parenting, gaming, and sustainability. In this episode, she shares her strategy for finding value where other investors aren’t looking, explains how Muse assesses early traction in non-traditiona…
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Fredrik Thomassen, co-founder and CEO of Superside, joins the show to unpack how startups can scale creative work without slowing down or burning out their teams. Superside is a subscription-based design company that helps fast-growing teams get high-quality creative at scale. In this conversation, Fredrik shares how he built a globally distributed…
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As Democrats seek to reestablish their credibility, Jon is joined by Crooked Media founders and "Pod Save America" hosts Jon Favreau and Jon Lovett. Together, they dissect the political and media environment that shields established leaders from accountability, debate how Democrats should position themselves during Trump's second term, and explore …
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Dale values symbol BDL and talks about the benefits of diverse menus in the restaurant business. Verbal disclosures read from 1:18-2:27. General information and full disclosures for Dale’s Solo Investors Podcast LLC are listed here: dalex5.podbean.com Sign up for Guru Focus: https://www.gurufocus.com/?affid=213fdcd9248dba7b149775aea75327e1 , click …
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Jesse breaks down the exact cold call routine he uses daily to drive pipeline. SPONSORS: • ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp EPISODE LINKS: • Want to get better at cold calls? Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNE…
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Jesse reminds sellers why understanding the product matters, especially when selling to IT buyers. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: •…
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As concerns mount over presidential profiteering, Jon is joined by Susan Glasser, New Yorker staff writer and co-author of "The Divider: Trump in the White House, 2017-2021," and Eric Lipton, investigative reporter for The New York Times. Together, they explore the scope of Trump’s business entanglements, discuss the challenges of covering these et…
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Jesse shares a real-life look at how he juggles tech sales, content creation, fitness, and family life each week. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNEC…
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What makes a founder dangerous? Not credentials. Not their pedigree. And it's not who they know. For investor and former operator Promise Phelon, a dangerous founder is someone with lived experience, relentless conviction, and the ability to build something the world doesn't expect. Promise is the founder and managing partner of Growth Warrior Capi…
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In this era of executive overreach, Jon is joined by Representatives Tom Suozzi (D-NY) and Brian Fitzpatrick (R-PA), co-chairs of the Problem Solvers Caucus, to examine how bipartisanship might still be possible. Together, they explore the caucus's approach to building consensus across party lines, discuss what leverage remains with the legislative…
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Jesse shares real strategies for SDRs looking to break into AE roles, drawing from his own journey from SDR > SDR Leader > Enterprise AE. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-…
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What kind of founder spends five years building a product before going to market? One who's trying to solve a very hard problem. Vince Gaydarzhiev is the founder of Alcatraz, a deep tech startup that uses facial authentication. The platform isn’t used to lock people out of single offices or consumer gadgets; its customers are buying global enterpri…
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What turns a free trial user into a paying customer? For Ola Sars, founder and CEO of Soundtrack, the answer is all about behavior. In this episode, we break down how his team uses product-led growth (PLG) and product-qualified leads (PQLs) to drive conversions. You'll hear how playing 100 tracks became a key signal for purchase intent, the tactics…
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In a political landscape defined by polarization, Jon is joined by Kentucky Governor Andy Beshear to discuss his success as a Democrat in a deeply conservative state. Together, they explore his approach to revitalizing Kentucky communities, examine his blueprint for winning in Trump country, and consider how he plans to lead his state through a sec…
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Jesse gives his take on why you should consider spending the first few years of your career in an office. SPONSORS: • Pre-Order Commission Impossible! - https://www.salesplayers.co/products/ci EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://ww…
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Jesse shares his basic process for negotiating compensation as a tech seller. SPONSORS: • Pre-Order Commission Impossible! - https://www.salesplayers.co/products/ci EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodb…
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Dale talks about five Cyclically Adjusted Valuation Ratios: Cyclically Adjusted Enterprise Value to EBIT (CAEE™) , Cyclically Adjusted Price to Book (CAPB™), Cyclically Adjusted Enterprise Value to EBITDA (CAEVE™), Cyclically Adjusted Enterprise Value to Free Cash Flow (CAEF™), and Cyclically Adjusted Enterprise Value to Gross Profit (CAEG™) . Verb…
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Jesse talks about mindset shifts sellers can embrace for long-term success. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Pre-Order Commission Impossible! - https://www.salesplayers.co/products/ci • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jes…
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As Trump's actions and rhetoric rock the global economy, Jon is joined by Rory Stewart, former British Cabinet Minister and current co-host of “The Rest is Politics.” Together, they examine the rapidly shifting relationships between the U.S. and its traditional allies, discuss the opportunities these shifts create for China, explore which policies …
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Mike Conover started his career as a machine learning engineer. Today, he’s the co-founder and CEO of Brightwave, an AI startup helping financial professionals make faster decisions with massive, unstructured data. In this episode of Fund/Build/Scale, Mike shares how he made the leap from technical contributor to strategic leader—and the hard lesso…
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Dale discusses a novel approach to valuing individual stocks. Verbal Disclosures read from 2:54 - 3:50 . General information and full disclosures for Dale’s Solo Investors Podcast LLC are listed here: dalex5.podbean.com Sign up for Guru Focus: https://www.gurufocus.com/?affid=213fdcd9248dba7b149775aea75327e1 , click "Book a Demo" CAEE™ Ratio — Pate…
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Dale talks about BFH , Credit card duopolies , and how retail stocks benefit. Episode starts at 0:15 . Verbal Disclosures read from 0:50 - 2:00. General information and full disclosures for Dale’s Solo Investors Podcast LLC are listed here: dalex5.podbean.com Sign up for Guru Focus: https://www.gurufocus.com/?affid=213fdcd9248dba7b149775aea75327e1 …
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As the Trump administration’s attacks on diversity initiatives intensify, we’re joined by Heather McGhee, author of "The Sum of Us”. Together, they explore the myths fueling anti-DEI sentiment, examine how the Trump administration weaponizes racial grievance to protect powerful interests, and discuss how a truly inclusive society benefits everyone,…
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Jesse shares ideas for how you can become a more fierce competitor in your deals. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • Mutual Action Plan: https://docs.google.com/pres…
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Igor Taber has sat on both sides of the table: first as a VC at Intel Capital, then as an operator at high-growth AI startup DataRobot. Now, as co-founder of Cortical Ventures, he’s backing the next generation of AI-first startups. In this episode, Igor shares how his operating experience reshaped his investment lens, what most VCs still miss about…
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Runway CEO and co-founder Siqi Chen shares how his team used a waitlist not just to build hype, but to engineer smarter growth. In this episode of Fund/Build/Scale, Siqi breaks down how Runway strategically kept customers in a holding pattern to gather feedback, qualify demand, and refine product-market fit. We also talk about: How to build trust w…
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Rachit Kataria is the Co-Founder & CEO of Centralize (https://www.usecentralize.com/) an all-in-one deal collaboration platform for enterprise revenue teams backed by Y Combinator. In this episode, Rachit shares his career story, the origins of Centralize, and the AI opportunity for Enterprise Sales. SPONSORS: • Surfe (LinkedIn Prospecting Streamli…
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As the economy reels from Trump's sweeping tariffs, Jon is joined by former Transportation Secretary Pete Buttigieg to examine the fallout. Together, they explore what Trump's levies mean for everyday Americans, discuss how to bridge the divide between politicians and the people they serve, and consider how a new generation of leadership might rebu…
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Jesse shares how he is planning to navigate the uncertain times ahead and asks for feedback on what direction to take the show. Please reach out on Slack, InMail, or email [email protected] to share: #1 What keeps you coming back to the show? #2 What topics would you like to hear more about? For a few of you, I'll pay you for your time giving m…
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Jesse shares the 10k play for developing a PoV when reaching out to executives at public companies. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • Book FREE 1:1 Coaching Intro w…
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As the Trump administration targets the federal workforce, we're joined by Michael Lewis, editor of and contributor to The New York Times bestselling collection "WHO IS GOVERNMENT?: The Untold Story of Public Service.” Together, they explore the vital yet uncelebrated work of civil servants, discuss why negative perceptions of them persist, and con…
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Ayelet Noff has spent more than two decades helping startups land meaningful press — but she’s also seen how the game has changed. In this episode of Fund/Build/Scale, the founder of SlicedBrand and new PR tech startup Dazzle shares what still works, what doesn’t, and how founders can earn meaningful attention in today’s fractured media landscape. …
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