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As a small business owner, you know copywriting is one of the essential “skills to pay the bills.” But how often do you sit down at your laptop and struggle with knowing what and how to write? You’re not alone. It’s difficult to write your own copy (even for pro copywriters). Plus, when you’re juggling a family, clients, and a team... there just isn’t enough time in the day to do it all. It’s why sending an email to your list or updating your website never gets crossed off your to-do list. E ...
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The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show note ...
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Getting real about what it takes. The Amy Porterfield Show is a podcast devoted to helping online business owners grow their revenue, audience, and team in a sustainable way that doesn’t just require more time and hustle. Host Amy Porterfield, New York Times bestselling author and $130MM online business owner, shares insights from her own 16+ years in business, as well as candid conversations with leaders in the industry, captivating experts, and the unexpected entrepreneurs who’ve cracked t ...
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Against All Odds Radio Show

Sean V. Bradley CSP, L.A. Williams

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Sean V. Bradley, AKA “The Millionaire Car Salesman”, personifies the American dream and what a person is truly capable of achieving in this country. Sean was born into violence, poverty and abuse, in Queens, NY, which led to boys homes, gangs and eventually federal prison. However, Sean wanted more than to be a statistic and against all odds rose from the depths of hell, to become a multi-millionaire of multiple companies, a best-selling author and a “CSP” in the National Speakers Associatio ...
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Kieran Flanagan is the CMO at HubSpot, where he’s led the transformation of their growth strategy from SEO-led to multi-channel and AI-powered. Formerly SVP of Marketing, he helped scale HubSpot’s user base to millions and revenue past $2B. Before HubSpot, he drove breakout growth at Marketo and Salesforce. Kieran is one of the most respected voice…
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Agenda: [00:00] The AI Talent Crisis No One’s Ready For [03:00] Daniel Gross and Nat Friedman: Why Two Legendary VCs Walked Away From $1B to Join Meta [12:00] Meta’s AI Talent Magnet: Will It Actually Work? [15:00] Cursor Is Breaking the Market: Can Anyone Compete? [18:30] OpenAI’s SBC Bombshell: More Stock Comp Than Revenue [22:00] CoreWeave’s Pow…
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If you tuned in to last week's episode, you know we discussed the importance of being bold and clear in your messaging and marketing. Right now, one of the biggest trends is having a clear point of view. Nothing helps you stand out more in your marketing than knowing how to articulate what you do and whom you help in a clear and compelling way. Som…
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The Bold Reset You Didn't Know You Needed If you’ve ever found yourself chasing a version of success that no longer fits, this episode is your reminder that you have the power to rewrite your rules. I’m joined by powerhouse entrepreneur and author Morgan DeBaun to explore what it really means to build a business and life on your own terms. We talk …
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Scott Galloway is a Professor of Marketing at NYU Stern, where he’s taught for over two decades. He’s the founder of several successful companies, including L2 (acquired by Gartner for over $150M), Red Envelope, and Prophet. He’s a New York Times bestselling author of four books on business and tech, and co-hosts the award-winning Pivot podcast. Ga…
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AGENDA: 00:00 – $400B in AI CapEx: Rational Investment or Madness? 05:00 – Figma's IPO: Rule of 80, $1.5B in cash, 40% margins. Unreal. 08:00 – Adobe Screwed the Deal—Should They Have Just Bought Canva? 16:00 – Pay-to-Play Deals: Heroic Hail Mary or Guaranteed Write-Off? 21:30 – How Index Is Returning $3.5B on 2 Deals 24:00 – Melio’s $2.5B Exit: In…
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Welcome to the Summer Remix series on the Ill Communication Podcast! ☀️ Every summer, I take a short break from recording new content and re-air some of the most popular episodes (fan favourites, most downloads!) This week, we’re revisiting an episode originally released at the very start of 2025. In it I share 7 copywriting and marketing trends th…
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When Your Copy Evolves, So Does Your Business In this episode, I share how shedding "safe" copy transformed my business. From sharpening your brand message to showing up as your unapologetic self, I dive into the copywriting strategies that helped me write with more clarity, confidence, and connection. You’ll learn how to channel bold, emotionally …
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Philipp Freise is Co-Head of European Private Equity at KKR, where he manages the largest private fund in Europe with $8BN in the latest fund. Philip has led KKR's investments in FGS Global, Superstruct, Axel Springer SE, BMG Rights Management, Fotolia, GetYourGuide, GfK SE, Leonine, Mediawan SAS, Scout24 Switzerland and Trainline. Previously, Phil…
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Kim Graves is GM, Americas at Notion, where she oversees all Sales and Customer Success efforts across the region. She brings extensive experience in building and scaling high-performing sales organizations, most notably at Slack where she helped grow revenue from $6M to over $1.5B. In addition to her operational role, Kim serves as a founding part…
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Agenda: 04:21 - The Meta Acquisition Bombshell: Nat Friedman & Daniel Gross Join Facebook?! 06:00 - Facebook’s $100 Billion Gamble: Can Zuck Buy the Future? 09:27 - The “Magic Room” Theory: Why Only Insiders Get Billion-Dollar Paydays 11:27 - Is Loyalty Dead in Silicon Valley? The Great Talent Exodus 16:00 - Harvey’s $5 Billion Valuation: Genius or…
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The marketing landscape has changed big time, and today’s buyers are more cautious, more skeptical, and taking way longer to say yes. In this episode of Ill Communication, I’m breaking down the three essentials your business needs to sell with more clarity and ease in 2025, especially in what many experts are calling a “trust recession.” We cover: …
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The Website Upgrade Your Business Has Been Waiting For Want a brand that instantly builds trust and makes you money? It all starts with your website. In this episode, I’m joined by Jen Olmstead, co-founder and lead designer of Tonic Site Shop. Jen is a design powerhouse with a journalism background, and she’s here to show you how to incorporate you…
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Johannes Reck is the Founder and CEO of GetYourGuide, the $2BN company that started with a holiday to China and nothing to do. For the first two years, GetYourGuide received only 5 bookings. Today the platform is worth $2BN. They have raised from some of the best, including an amazing story with Masa Son and Softbank. In Today’s Episode We Discuss:…
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Cem Kansu is the Chief Product Officer at Duolingo, where he leads product strategy for over 90 million monthly active learners. Since joining Duolingo, Cem has played a pivotal role in driving record user engagement, revenue growth, and product innovation, including the launch of Duolingo Math and the wildly successful Duolingo Music. Under his le…
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Agenda: 00:00 – Meta’s $14.8B Deal for Scale: The Analysis 05:40 – Will Scale Lose Their $800M ARR? Will All Customers Leave? 13:00 – Who is the Winner from All Scale Customers Leaving? 21:30 – Who Made the Most Money From Scale? 24:00 – LPs Just Got $14B Back. Are They Reinvesting? 26:45 – Chime IPO: The Breakdown 29:20 – Ramp Hits $16B Valuation:…
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Tired of writing sales copy that just seems to list out features and specs, but leaves your readers yawning? In this special 150th episode of Ill Communication, I’m diving into the secret sauce that transforms dull, lifeless sales copy into a message that sparks curiosity and inspires action: the FAB Formula. It’s the technique that helps you bridg…
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What Helped Me Trust My Team, Protect My Energy, and Step Into True Leadership I’ll be honest—this conversation with Patrick Lencioni shook me (in the best way). If you’ve ever felt like running your business is way harder than it should be, or like you’re carrying the weight of every single task on your back, this episode is going to be a game cha…
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Larry Aschebrook is the Founder and Managing Partner of G Squared in what is one of the wildest stories of venture capital. Larry started G Squared with nothing, dialling for dollars having personally invested in Twitter and Uber. In his first fund, Larry made sizable bets into SpaceX, Palantir, Alibaba and Twitter. Larry has also had mega losses a…
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Agenda: 00:03 – Circle’s IPO: Investors Just Left $BNs on the Table 00:06 – CoreWeave & Circle: Are We Back to Meme Stock Madness? 00:11 – Should Stripe and Databricks Finally Go Public? 00:17 – US Stock Markets: How They DOMINATE the Global Game 00:21 – 50% of Unicorns Are DOOMED. What Happens Now? 00:25 – Founders Fund Just Dropped $1B on Anduril…
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How often do you stop to truly celebrate your wins—big and small? In this episode, I dive deep into why celebrating successes matters more than you think, both in your business and in your personal life. From sharing personal stories of family milestones to reflecting on how I often skip over acknowledging wins in business, this episode is all abou…
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Joy Is Not a Reward for Success — It's a Tool That Drives Sustainable Success In this episode, I’m talking to the version of you who’s not completely burned out…but you’re definitely not lit up either. You’re just fine. You’re checking off the to-dos without that sense of momentum, joy, or excitement that once fueled your business. Sound familiar? …
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Micha Kaufman is the Founder and CEO of Fiverr, the leading online marketplace for freelance services. Fiverr has had an insane ride in the public markets, in 2019 the company went public with a $650M market cap, at their peak that hit over $8BN. Today, facing a wave of AI, the company has a market cap of $1.121BN on an estimated $430M EOY revenues…
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Matt Pohlson is the co-founder and Chairman of Omaze, the most insane story in startups that you have never heard. From near death experience to working with Arnold Schwarzenegger, George Clooney and The Pope. Omaze has raised over $200 million for charity by offering once-in-a-lifetime celebrity experiences and luxury house draws. He's a master st…
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Agenda: 00:00 – The Most Unfiltered Episode Ever Begins 03:30 – Does OpenAI Even Matter? Sam Lessin Says Maybe Not. 05:45 – TVPI Is Bullshit? 09:20 – Asset Gatherers vs Real Investors: Who Actually Wins? 12:15 – The Death of the Billion-Dollar VC Fund? 16:00 – Mid-Tier VC Funds Are Getting Annihilated 21:00 – Chime: Great Exit or Missed Opportunity…
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The New Visibility Strategy That Doesn’t Require Hustling, Performing, Or Pretending Let’s be honest—social media can feel like a never-ending hamster wheel, and trying to “beat the algorithm” is exhausting. That’s why I wanted to have a real conversation about an entirely different visibility strategy—one that actually works and doesn’t rely on so…
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What would it take for you to truly unplug this summer—without your business missing a beat? I’m sharing all the juicy details about my most popular workshop of the year: The Summer of Ease. I walk you through why planning now can give you the freedom to enjoy more sunshine and yes—more ease. Join me as I break down exactly what we’ll be doing toge…
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The Simple Shift That Turned My Low-Converting Offer Into Scalable Success Let me say something that might feel like a relief: you don’t need more offers. What you actually need is a clear path for your audience to say yes. In this episode, I’m sharing a massive mindset and strategy shift I made in my own business—one that took me from trying to pu…
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Varun Mohan is the CEO and Co-Founder of Windsurf, the leading AI-native IDE, which has over a million users and generates over 50% of all committed software across thousands of companies. Prior to Windsurf, Varun graduated with a Master’s in Computer Science from MIT and led a team at Nuro focused on large-scale deep learning infrastructure for au…
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Kyle Norton is the Chief Revenue Officer at Owner.com, where he scaled revenue from $2M to $40M ARR in under 3 years while selling to one of the toughest markets: SMB restaurants. Before Owner, Kyle led sales at Shopify, where he helped architect one of the most operationally elite GTM orgs in SaaS. Agenda: 00:00 – From Shopify to $40M ARR at Owner…
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Agenda: 00:00 – Why “Fund Returners” Are a Myth in Late-Stage VC 05:02 – Builder.ai Implodes: $500M Gone & Fraud Allegations Begin 11:40 – The Dirty Truth About Late-Stage Venture Math 15:57 – The Hinge IPO: Who Won, Who Lost, and Why It’s a Game Changer 23:03 – The Chime Bombshell: Late-Stage VCs Forced to Crystallize Huge Losses 27:14 – Why YC Is…
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This episode is different—and deeply personal. I'm stepping away from the usual copywriting tips to talk about something many of us avoid: mental health, burnout, and the hidden toll of holding it all together. The past year left me mentally and emotionally tapped out, and I didn’t even fully realize it until I was on the other side. So in honor of…
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Airwallex is the most insane story in startups: The best angel investment ever: The angel that turned $1M into $1BN. One of the world's best VCs pulled a term sheet and lost $1BN. The company turned down a $1.2BN offer from Stripe. The company scaled to $1BN in transaction volume in 9 months. The company has never not grown 100% in a year. Jack Zha…
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How To Own the Room, Build Trust, and Convert—With Just One Signature Story Whether you're hosting a webinar, guesting on a podcast, or stepping onto a live stage, your ability to sell starts with mastering the art of connection. In this episode, I sit down with Colin Boyd, international speaker and business mentor, for a high-impact conversation a…
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Luke Harries is Head of Growth at ElevenLabs, where he leads marketing, product, engineering, and developer experience. ElevenLabs has raised $281M with the latest round pricing the company at $3.3B valuation. Previously, Luke held roles at PostHog and Microsoft, and is also an angel investor supporting startups like Lovable and Runna. In Today’s E…
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Agenda: 04:34 Chime's IPO Announcement: Who Wins & Who Loses 06:28 The Lopphole That Means Chime Has a Better Business than JP Morgan 10:51 Why Investors Who Invested at $25BN Will Make Money When it IPOs at $12BN 18:59 Are IPOs Dead & The Future of the Late Stage Private Market 27:32 Exits are Larger Than Ever: So What? What Happens? Who Wins? Who…
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How do you turn what's happening in your life right now into compelling content your audience actually wants to read? I’m sharing a powerful seasonal writing prompt that will help you show up consistently and with purpose—whether it’s through email, social media, blog posts, or your podcast. I’m in the thick of baseball season with my son, and it g…
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What If Your Biggest Growth Opportunity Was Rethinking How Your Customer Actually Moves Through Your Business? If your business growth feels stalled, the issue might not be your funnel, ads, or webinar strategy — it could be that your ideal customer has outgrown you. In this episode, I introduce a powerful reframe around how to think about your cus…
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Severin Hacker is the Co-Founder and CTO of Duolingo, the world’s most downloaded education app with over 100 million monthly users. Since its 2021 IPO, Duolingo has reached a market cap of $20BN. The company has raised over $183M from top-tier investors including CapitalG, Kleiner Perkins, Union Square Ventures, NEA, Ashton Kutcher, and Tim Ferris…
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How to Build a Membership That Fuels Freedom, Stability, and Long-Term Growth If you've ever wondered whether a membership could work in your business model — or if you're still sitting on the sidelines debating when to make the leap — this episode is your permission slip to stop waiting and start validating. Stu McLaren is here for an unfiltered, …
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Yuhki Yamashita is the Chief Product Officer at Figma, where he leads the development of one of the world’s most beloved design platforms. Previously, he was Head of Product at Uber, overseeing the core rider experience used by millions globally. A master of product storytelling and team-building, Yuhki has redefined how world-class digital product…
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Items Mentioned in Today’s Episode: 04:11 Owner’s New $120M Round at $1BN 06:05 Why Series A is F****** Today 14:55 Could Tiger Global Be Saved by OpenAI and Scale 22:43 Why SBF is the Greatest Investor of the Last Decade 31:34 Why No Individuals Should Invest in Venture Funds 36:27 Why Microsoft Laying 3% of Their Workforce Off is not Enough 41:38…
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What if “f*cking around and finding out” was exactly the mindset you needed to gain new traction in your business? In this episode, I’m pulling back the curtain on my new FAFO (F*ck Around and Find Out) era—what sparked it, how it reshaped my marketing approach, and why I’m finally letting go of perfectionism. If you’re anything like me, you might’…
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Clarity Over Guesswork: The CEO-Level Questions You Should Be Asking What if the only thing standing between you and your next big leap in business is how you see your business? I’m joined by powerhouse business strategist and five-time Forbes business coach Jessica Marx. Together, we unpack what it really takes to scale with clarity, confidence, a…
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Immad Akhund is the CEO of Mercury. Launched in 2019, Mercury has raised $500M in funding from Sequoia, Coatue, CRV, Andreessen Horowitz and others. He is a former part-time partner at Y Combinator and is an active angel investor, with more than 350 investments in startups including Rippling, AirTable, Rappi, Applied Intuition, and Substack. In Tod…
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Eléonore Crespo is the Co-Founder and CEO @ Pigment, one of Europe’s fastest-growing companies. With Pigment, Eleonore has raised over $397M from the best in the world including ICONIQ, Greenoaks and IVP to name a few. Prior to Pigment, Eléonore was on the other side of the table as an investor with Index Ventures. In Today's Episode We Discuss: [0…
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How many people are missing out on your offer just because it’s hard to find or share? I’m giving you six dead-simple, free, and often overlooked ways to promote your offers that you can implement today. These strategies are designed to support all types of buyers from the DM-happy to the lurkers who never comment but love to click. Tune in to lear…
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Today’s Topics: 04:44 Analysis of $3 Billion Windsurf Acquisition 12:39 Will Mega Funds Win the Future of Venture Capital 18:39 Does Every Fund Have to do Pre-Seed to Win Series A and B Today 27:53 Why AI Will Create Massive Unemployment 31:06 The $100,000 Bet on the Future of Work 35:52 Why Venture Has Become a Bundled Good 37:52 Why Stage Specifi…
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More Isn’t Always Better—Here’s Why Knowing Your ‘Enough’ Changes Everything If you’ve ever felt stuck chasing bigger goals just because you should—you’re not alone, and you’re not wrong for wanting a different pace. In fact, this episode might be exactly what you didn’t know you needed. I'm sharing something that completely shifted the way I opera…
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Bucky Moore is a Partner @ Lightspeed Venture Partners, announced exclusively in the show today on 20VC. Prior to Lightspeed, Bucky spent an incredibly successful 7 years at Kleiner Perkins working with Mamoon Hamid to build one of the most successful early stage firms of the last decade. Bucky has made investments in the likes of Prisma, Netlify, …
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