Fundraising: Demystified! True Stories Direct From Founders

Jason Kirby

In this podcast, we uncover the untold stories of founders who have weathered the highs and lows of raising capital. We go beyond the headlines and Techcrunch funding news articles to explore the uncharted territories of the fundraising landscape. In each episode, we'll sit down with founders from various industries who have raised venture capital to bring their visions to life. They'll open up about their personal journeys, fundraising tactics & more. If you're a founder, this podcast offers a ton of value & insights you can apply to your fundraising journey. Don't forget to hit subscribe!

  1. EP 90: Search Funds Demystified: How Jon Staenberg (Agate Hound Fund) Nets 35% Annual Returns

    19 JUN

    EP 90: Search Funds Demystified: How Jon Staenberg (Agate Hound Fund) Nets 35% Annual Returns

    This week, I chat with Jon Staenberg founding partner of Agate Hound Fund, to unpack the real mechanics behind venture capital and search funds. From his early days at Microsoft, to founding a search fund that delivers 35% net annual returns, Jon pulls no punches. He warns, “Don’t go into venture until you’ve actually got a skill,” and breaks down the challenges of buying a company. We explore how grit, curiosity, and critical thinking separate founders who retire early from those who build enduring empires, and why the “comprehensiveness of change today is astonishing.”  Whether you’re curious about launching a search fund, leveling up in VC, or simply hungry for insights, this episode will equip you with the tools and the mindset to raise your game. Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Spotify&utm_medium=Video&utm_campaign=Episode90&utm_id=FundraisingDemystifiedPodcast Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Spotify&utm_medium=Video&utm_campaign=Episode90&utm_id=FundraisingDemystifiedPodcast We explore: 0:00 – Intro & Meet Jon Staenberg of Agate Hound Fund 4:50 – “Microsoft was way beyond my expectations…” 10:30 – “Don’t go into venture until you’ve actually got a skill” 16:15 – Search Funds 101: “5% net annual return 22:00 – “Buying a company is hard… it’s messy” 28:05 – Why grit, curiosity & critical thinking win 33:40 – The “retire early” myth vs. 60‑hour workweeks 38:20 – AI & the comprehensiveness of change today 42:10 – How to connect with Jon ABOUT JON STAENBERG Jon Staenberg is the founding partner of Agate Hound Fund, a search‑fund vehicle focused on acquiring and scaling founder‑owned companies. Before launching Agate Hound, Jon spent over a decade at Microsoft, where he led product strategy and saw firsthand how engagement and inspiration fuel innovation. A veteran operator turned investor, he’s passionate about teaching entrepreneurs that “buying a company is hard,” but also demonstrating how a disciplined, skill‑based approach can generate 35% net annual returns. Jon holds an MBA from Stanford and advises several high‑growth startups on go‑to‑market and capital strategy. Get in touch with Jon: Website: https://www.agatehound.fund/ Email: jon@agatehound.fund   ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: jason@thunder.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED  Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

    43 min
  2. EP 89: From Uber to Snap to AI: Ben Chiang on Raising Millions Then vs Now

    12 JUN

    EP 89: From Uber to Snap to AI: Ben Chiang on Raising Millions Then vs Now

    In this episode of Fundraising Demystified, I sit down with Ben Chiang, the former head of Uber China and founder of Forma (acquired by Snap- yes, from Snapchat), to unpack his journey through hypergrowth, high-stakes fundraising, and strategic exits. Ben shares the realities behind building in chaotic markets, the truth about investor dynamics post-exit, and how founders can stay sane while chasing scale. We dive into the underrated benefits of QSBS (Qualified Small Business Stock), why consumer startups have it tougher than ever, and the unique marketing challenges of building AI products in today’s crowded landscape. Great watch if you’re curious about any aspect of building and exiting in tech. —--------------------------------------------------------------- Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode89&utm_id=FundraisingDemystifiedPodcast Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode89&utm_id=FundraisingDemystifiedPodcast We talk: 00:00: From Zero to 50 Million Weekly Rides: Uber China’s Blitzscale Playbook 02:48: Why Market Fit Is Make or Break 06:07: Timing, Relationships & the Hidden Rules of Fundraising 08:58: Forma’s Acquisition by Snap: Behind the Deal 11:57: Luck, Credit, and the Realities of Startup Success 15:00: Negotiating from Leverage vs. Desperation 26:13: Founders vs. Investors: What Changes After an Exit 28:08: QSBS: The Most Underrated Tax Benefit in Startups 30:27: How Stock Market Volatility Affects Founders 32:11: Leaving Snap: Rediscovering Purpose 33:43: The Messy Reality of Building and Marketing AI Products 37:14: Fundraising Now vs. Then: What’s Actually Changed? 40:57: Herd Mentality and the Modern VC Landscape 44:07: What It Takes to Enjoy the Founder Journey 47:00: Final Advice: Know What You Want ABOUT BEN CHIANG Ben Chiang is a veteran operator and founder best known for launching Uber in China and later founding Forma, a startup acquired by Snap. His experience spans scaling platforms in hypercompetitive markets, navigating complex acquisitions, and now building across multiple AI content ventures. Get in touch with Ben: LinkedIn: https://www.linkedin.com/in/benjaminchiang/ Twitter: https://x.com/ben_chiang   ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: jason@thunder.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED  Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

    53 min
  3. EP 88: How a Broken Leave Policy Led to a $30M HR Tech Startup w/ Jenniffer Henderson (Tilt)

    5 JUN

    EP 88: How a Broken Leave Policy Led to a $30M HR Tech Startup w/ Jenniffer Henderson (Tilt)

    60 pitches in 90 days. A Series B term sheet that collapsed. A $15M valuation hit, and she still came out on top. In this episode, Jennifer Henderson, founder of Colorado-based HR tech startup Tilt, breaks down exactly what it took to raise over $30 million in venture capital while balancing motherhood, market crashes, and investor whiplash. Jen shares how Tilt was born out of personal trauma, why she built a leave management platform with empathy at its core, and what every founder, especially women, needs to know before walking into their next pitch. From Techstars to term sheet disasters, this is the real story behind startup success in today’s market. —--------------------------------------------------------------- Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode88&utm_id=FundraisingDemystifiedPodcast Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode88&utm_id=FundraisingDemystifiedPodcast Here's what you're in for:00:00 – “I don’t come from money”: Why Jen chose venture 04:21 – Building Tilt from personal pain 06:08 – Sales tactics that worked 09:07 – How Techstars changed the fundraising game 11:53 – Raising Series A: Saying no to ‘cute’ term sheets 18:03 – Series B nightmares: exclusivity traps, errors & resilience 33:07 – The truth about AI in HR tech 39:02 – Advice to female founders: “Be successful. We need you.” 42:56 – Surviving the current startup market   ABOUT JENNIFER HENDERSON Jennifer Henderson is the founder & CEO of Tilt, a Colorado-based HR tech platform that simplifies and humanizes leave of absence management for modern teams. After two traumatic parental leave experiences, she turned her frustration into a mission. From Starbucks barista to corporate leader to raising $30M+ across five rounds, Jen's journey is a masterclass in resilience, grit, and founder-first leadership. Tilt is now a trusted solution for teams across the U.S., navigating complex leave policies with care. Connect with Jennifer on:LinkedIn: https://www.linkedin.com/in/jenniferhendersonjctcjcdcEmail: hello@tilt.com ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: jason@thunder.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED  Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

    46 min
  4. EP 87: Customer Retention Over Acquisition? Travis Steffen, Who’s Done $200M in Deals, Says Yes

    29 MAY

    EP 87: Customer Retention Over Acquisition? Travis Steffen, Who’s Done $200M in Deals, Says Yes

    This week, I talk to Travis Steffen, who has built and sold eight companies. He’s raised over $100M and driven more than $200M in exits. In this episode, we delve into what actually drives startup growth and what quietly undermines it. We also get into how one bad exit almost wrecked him, and what he learned from losing years and seven figures because of one avoidable mistake. If you're a founder, operator, or even just thinking about building, this episode will give you a clearer view of what’s worth your attention. —------------------------------------------------------------------- Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode87&utm_id=FundraisingDemystifiedPodcast Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode87&utm_id=FundraisingDemystifiedPodcast We get into: 00:00 The Real Startup Journey: No Filters, No Hype 03:07 Why "Never Quit" Is Holding You Back 05:47 Churn: The Growth Killer Founders Ignore 09:12 What You Learn When a Startup Fails 12:05 Retention Isn’t a Metric. It’s a Strategy. 14:52 Why Investors Walk, Even If Your Numbers Look Good 17:48 The Retention-Valuation Link You Can’t Ignore 21:06 From Flatlined to $70M: A Turnaround Breakdown 34:37 How We Built the Most Trusted Brand in a Broken Industry 36:19 Revatto: Built to Solve Churn Without Adding Work 40:07 No Results, No Cost: A Different Kind of Retention Model 42:29 How To Save Customers, Without a Product Tutorial 45:10 You Probably Don’t Understand Your Churn. Here’s Why. 47:24 How to Test Revatto, with $1,000 in Free Recoveries 51:21 One Retention Habit That Changes the Game 54:24 The Exit That Went Sideways,  and What It Cost   ABOUT TRAVIS STEFFEN Travis Steffen is a founder, operator, and builder with a track record most founders never reach. He’s exited eight companies, raised more than $100M, and led over $200M in M&A. His work spans SaaS, cannabis tech, fintech, and AI. Today, he’s the co-founder of Revatto, a company that helps subscription-based businesses retain more customers and only charges when it works. Check out Revatto: https://www.revatto.com/   ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: jason@thunder.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED  Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

    1h 5m
  5. EP 86: What Founders Get Wrong About Exits (and How John Rood Got It Right)

    22 MAY

    EP 86: What Founders Get Wrong About Exits (and How John Rood Got It Right)

    Most founders dream of a life-changing exit. But few actually prepare for it, until it’s too late. In this episode of Fundraising Demystified, I sit down with John Rood, an exited founder who scaled a tutoring side hustle into a global edtech business, and sold it for over eight figures to private equity.John also shares the story behind his book Beyond the Exit and why post-exit life is often not what you think it will be. ---------------------------------------- Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode86&utm_id=FundraisingDemystifiedPodcast Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode86&utm_id=FundraisingDemystifiedPodcast We talk: 00:00 – The Brutal Truth No One Tells Founders 02:04 – How John Turned Tutoring into SaaS Gold 05:21 – The Finance Hack That Boosted His Valuation 07:10 – What Really Kicks Off an Exit 11:08 – The $10M Mistake Founders Keep Making 13:59 – What’s Actually Enough for You? 17:01 – Why Most Founders Regret Life After Exit 22:52 – Angel Investing: The Ego Trap No One Admits 28:22 – The Weirdly Happy Knife Founder Story ----------------------------------- About John Rood John Rood is the author of Beyond the Exit and the founder of one of the world’s leading pre-med test prep businesses. After scaling the company into a content-and-software powerhouse, he exited for over eight figures to a private equity firm. He now advises founders on exit strategy and post-exit reinvention, drawing from both his wins and the emotional landmines no one warns you about. Connect with John: LinkedIn: https://www.linkedin.com/in/johnrood1/ Get the book: https://www.beyondtheexitbook.com/

    40 min
  6. EP 85: From Burnout to Breakout: How Jennifer Tsai Bootstrapped Shoott.com to $10M After Raising $2.7M

    15 MAY

    EP 85: From Burnout to Breakout: How Jennifer Tsai Bootstrapped Shoott.com to $10M After Raising $2.7M

    What happens when you raise $2.7M... then realize you never want to raise again? Jennifer Tsai, founder and CEO of Shoott.com, built a profitable photography marketplace from the ground up; surviving death threats from creatives, a brutal CAC spike post-iOS14, and the chaos of marketplace economics. In this episode of Fundraising Demystified, we dive into how she scaled to $10M in revenue, hit breakeven, and is now facing the “what’s next” moment many founders dream of, or dread. Whether you're building a two-sided marketplace, wrestling with capital strategy, or wondering how to survive without more VC cash, this one's for you. Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode85&utm_id=FundraisingDemystifiedPodcast Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode84&utm_id=FundraisingDemystifiedPodcast In this episode, you'll learn: 00:00 – Death Threats, Disruption & The Origin Story of Shoott.com 05:45 – Why Creatives Hated Us And How We Won Them Over 12:08 – From $80K to $10M: The Fundraising + Growth Playbook 17:52 – How We Hit Profitability (And 20x’d It) 21:26 – Cash Flow Roulette: Paying Creators Before Clients Pay Us 22:57 – The $300K Mistake That Nearly Sank Us 25:57 – Should You Raise, Sell, or Stay the Course? 27:32 – The Brutal Truth About Valuations in Today’s Market 30:38 – Founders: Before You Build a Marketplace, Watch This

    42 min
  7. EP 84: David Connors Used The Swarm to Raise Millions | Deal Flow, M&A, and Warm Intros

    8 MAY

    EP 84: David Connors Used The Swarm to Raise Millions | Deal Flow, M&A, and Warm Intros

    This week on Fundraising Demystified, I sat down with David Connors, founder of The Swarm, a Go-To-Network platform transforming how founders and investors connect- think LinkedIn but for companies. David shares how he used The Swarm to raise capital for his own startup, how the product helps other founders close rounds, and what he learned from working at Sequoia. Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode84&utm_id=FundraisingDemystifiedPodcast Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode84&utm_id=FundraisingDemystifiedPodcast Sign up to get 70% off the Swarm: theswarm.com/thunder Here’s what you’re in for: 00:42 - Who is David Connors and what is The Swarm?02:08 - How working at Sequoia birthed The Swarm 05:32 - Raising The Swarm’s $2M pre-seed round solo (and why it was capped) 11:37 - Raising a $4M seed and scaling a building a winning team 14:31 - How to find investors and pick the right ones for follow-on funding 18:52 - Getting warm intros for investor outreach in minutes 22:28 - The best kind of warm intros ranked 25:43 - Why Swarm raised an extension round 29:10 - The shift from SaaS to data, 10xing revenue and getting Hubspot Ventures to invest 32:40 - Vibe coding and AI tools that support The Swarm’s scale 35:02 - Top tips for personal branding that boosted growth Check out the pre-seed investment memo for The Swarm here: https://docs.google.com/document/d/1wzo0PxFCyNgaD627-e2q2wefV0LUk4DJjnEr3R4b07k/edit?tab=t.0 ABOUT DAVID CONNORS David Connors is the founder of The Swarm, a Go-to Network platform that helps startups access warm intros to capital, talent, and strategic partners. A second-time founder with deep experience in startup M&A, David previously built a company acquired by Levels, a Sequoia-backed health tech firm. With a background in enterprise sales and operations, he built The Swarm to solve one of the hardest problems founders face: getting in front of the right people without wasting time on cold outreach. Connect with David via:LinkedIn: https://www.linkedin.com/in/connorsdavidWebsite: http://theswarm.com/ ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: jason@thunder.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED  Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thanks for tuning in! We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders. #startupfunding #venturecapital #theswarm #founderstories #fundraisingdemystified #saas #data #investoroutreach

    40 min
  8. EP 83: Jess Loren on Digital Twins & Unconventional Strategies of Raising Capital as Female Founder

    1 MAY

    EP 83: Jess Loren on Digital Twins & Unconventional Strategies of Raising Capital as Female Founder

    In this episode, Jess Loren, founder and CEO of Global Objects, shares her journey on raising capital as a female founder, including turning down a $20M offer and building her business using digital twins technology. Jess dives into how she's building a tech company rooted in culture, purpose, and innovation, while navigating the fundraising landscape as a female CEO. We talk about generative AI in media, managing a startup as a mom, building a tech community, and how to use AI to boost productivity. A great story about leadership, innovation, and startup resilience. —------------------------------------- Raising capital? Get a list of vetted VCs for FREE here: https://web.thunder.vc/list-of-investors-vcs-for-founders?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode83&utm_id=FundraisingDemystifiedPodcast Get the latest fundraising insights, news, and tips: https://blog.thunder.vc/funding-101?utm_source=Youtube&utm_medium=Video&utm_campaign=Episode83&utm_id=FundraisingDemystifiedPodcast Here's what you're in for: 00:00 - Intro 00:35 – Raising Capital as a Female Founder: Intro to Jess Loren & Global Objects 03:06 – Building a Tech Community in LA 06:05 – Balancing Life as a Female CEO 08:42 – Digital Twins Technology for Culture & Innovation 13:16 – Using AI to Boost Productivity in Creative Industries 16:34 – Generative AI in Media & Entertainment 22:18 – Jess Loren’s Journey: From 2X Exit Founder to Building Global Objects 25:47 – Funding Strategies & Investor Alignment 28:16 – Global Objects' Mission and Growth Plan 31:30 – Startup Leadership as a Female CEO 34:05 – Jess Loren on Persistence, Boards & Building Visibility   ABOUT JESS LOREN Jess Loren is a 2X exited founder and the CEO of Global Objects, a cutting-edge startup at the intersection of digital twins technology, cultural preservation, and generative AI. With a background in community building, immersive experiences, and Web3 innovation, Jess is known for her bold leadership, fundraising acumen, and vision for reshaping how we digitally capture and interact with the world. Her journey includes turning down a $20M term sheet to stay mission-aligned, proving that purpose and persistence can coexist at scale. You can reach out to Jess through: LinkedIn: https://www.linkedin.com/in/jessloren/ Global Objects' LinkedIn: https://www.linkedin.com/company/globalobjects/   ABOUT JASON Jason Kirby is the co-founder of Thunder VC. He is a serial entrepreneur with 4 multi-million exits and decades of experience in fundraising and business building. He has coached hundreds of entrepreneurs in his career on fundraising, investing, capital strategy, and business development. You can reach out to Jason through: Email: jason@thunder.vc LinkedIn: https://www.linkedin.com/in/jasonrkirby/ ABOUT FUNDRAISING DEMYSTIFIED  Our goal is simple: to equip you with the knowledge, inspiration, and guidance to navigate the labyrinthine world of fundraising. Whether you're a budding entrepreneur seeking seed funding or an established founder looking to scale your business, this podcast will provide you with the tools you need to conquer the fundraising landscape. Thank you for being a loyal subscriber to Fundraising Demystified. We appreciate your support and are excited to continue bringing you more inspiring stories from successful founders.

    44 min
5
out of 5
2 Ratings

About

In this podcast, we uncover the untold stories of founders who have weathered the highs and lows of raising capital. We go beyond the headlines and Techcrunch funding news articles to explore the uncharted territories of the fundraising landscape. In each episode, we'll sit down with founders from various industries who have raised venture capital to bring their visions to life. They'll open up about their personal journeys, fundraising tactics & more. If you're a founder, this podcast offers a ton of value & insights you can apply to your fundraising journey. Don't forget to hit subscribe!

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