PODCAST · business
Sit Down Startup
by Adam O'Donnell
Here’s how to startup. Even when the world goes topsy-turvy. From one home office to another, Zendesk leaders chat with founders, CEOs, and makers on their startup journey. There’s rule-flipping, new dogma and recycling failure into growth. Plus, why customer experience is at the heart of success, as told by people who know unpredictability inside out. (That seems pretty helpful right now.)
Episodes
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[$10M+ Raised] Mark Doble, Co-Founder of Alexi, on Overcoming Adversity and Achieving Product-Market Fit in Legal Tech
Welcome back to this week’s episode of Sit Down Startup! Today, host Adam O'Donnell sits down with Mark Doble, Co-Founder of Alexi, to explore his inspiring journey in the legal tech space and the challenges of achieving product-market fit while raising over $10 million in funding. Join us as…
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[Harnessing AI Technology for Business Growth] Founder Daniel Saks Discusses Persistence, Overcoming Rejection, and the Evolution of AppDirect and Landbase
In the latest episode of Sit Down Startup, Adam O'Donnell sits down with Daniel Saks, co-founder and CEO of Landbase, to delve into his entrepreneurial journey, including the successes and challenges he faced while building AppDirect. Daniel shares invaluable insights into the evolution of...
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[Sustaining Competitive Edge] CEO Randy Wootton of Maxio on the Dynamics of Product-Market Fit in a Changing Landscape
Welcome back to this week’s episode of Sit Down Startup! Today, host Adam O'Donnell sits down with Randy Wootton, CEO of Maxio, to delve into the intricate dynamics of sustaining product-market fit in the ever-evolving landscape of B2B SaaS. Join us as Randy shares his unique journey from…
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[$121.5M in Funding] Efficient Capital Labs' Kaustav Das on Bridging the Funding Gap and Achieving Product-Market Fit
Welcome back to Sit Down Startup! In this week's episode, host Adam O'Donnell sits down with Kaustav Das, co-founder of Efficient Capital Labs, a pioneering venture focused on transforming funding for SaaS founders. Join us as Kaustav shares his remarkable journey in navigating the complexities…
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[Pioneering Retail Innovation] CEO Angie Westbrock on Standard AI's Journey from Autonomous Checkout to Computer Vision Insights
Welcome back to this Thanksgiving week's episode of Sit Down Startup! Today, host Adam O'Donnell sits down with Angie Westbrock, CEO of Standard AI, to explore her inspiring journey from the manufacturing sector to leading a cutting-edge retail technology company. Discover how Standard AI pivoted...
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[$30M Raised] Transforming Legal Tech: Spellbook Co-Founder & CEO Scott Stevenson on Achieving Product-Market Fit
Welcome back to Sit Down Startup! In this week's episode, host Adam O'Donnell sits down with Scott Stevenson, co-founder and CEO of Spellbook, the first generative AI copilot for lawyers, to discuss his remarkable journey in the legal tech space. Uncover the invaluable insights Scott gained about...
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[Transforming Crypto Access] Co-Founder/CEO Driss Benamour on Building Exponential.fi and Overcoming Crypto Winter
In this episode, Adam O'Donnell sits down with Driss Benamour, co-founder and CEO of Exponential.fi, to explore the journey of building a decentralized finance platform amidst the challenges of the crypto winter. Driss shares his insights on achieving product-market fit by focusing on user needs...
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[Navigating the AI Landscape] Co-Founder and CEO Jensen Harris on Textio's Journey and the Future of AI in Management
In the latest episode of Sit Down Startup, Adam O'Donnell sits down with Jensen Harris, co-founder and CEO of Textio, to explore his remarkable journey in the world of AI-driven management solutions. Jensen shares how Textio has evolved over the past decade, transforming the way managers deliver...
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[~$100M Raised] Transforming Talent Assessment: Co-founder and CEO Tigran Sloyan on Building CodeSignal
Welcome to the latest episode of Sit Down Startup! Today, host Adam O'Donnell sits down with Tigran Sloyan, an MIT alumnus and the co-founder and CEO of CodeSignal, to discuss his remarkable journey to the forefront of innovation. Uncover the invaluable insights Tigran gained about resilience,...
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[Revolutionizing Climate Tech] Sealed’s co-founder and CEO Lauren Salz on Raising ~$100 Million and Finding Product-Market Fit
In the latest episode of Sit Down Startup, Adam O'Donnell chats with Lauren Salz, co-founder and CEO of Sealed, about her unexpected journey from aspiring musician to leading a revolutionary home energy startup. Discover the invaluable lessons Lauren learned about resilience, adaptability, and…
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[$300M Raised] Mapping the Human Immune System for Drug Discovery: Noam Solomon on Building Immunai
In this latest episode of Sit Down Startup, Adam O'Donnell chats with Noam Solomon, CEO of Immunai, about his incredible journey from academia to building a groundbreaking biotech startup. Hear Noam's fascinating backstory growing up in Israel and his move to the U.S. for a postdoc at MIT and...
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[90% of Co-Founder's Time Spent Speaking to Customers] How Inspectify has Navigated Startup Success
Welcome to the latest episode of Sit Down Startup! This week Adam O'Donnell hosts Inspectify co-founder and CEO Josh Jensen who leverages his diverse background in engineering and real estate to revolutionize property inspections for single-family homes. Josh brings a unique perspective to the…
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[$0 to $20M ARR in 1 year] Creating a Path to Financial Empowerment with Brigit's co-founder and CEO Zuben Mathews
Host Adam O'Donnell is back with this week's episode of Sit Down Startup with guest Zuben Mathews, co-founder and CEO of the financial health app Brigit. Mathews draws from his own experiences of financial hardship and his background in economics to address the critical issue of product-market…
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[$150M Raised] Navigating Product-Market Fit in Healthcare: Ashok Subramanian on Building Centivo
In this insightful episode of Sit Down Startup, Ashok Subramanian, founder of Centivo, shares his incredible journey from immigrant roots to becoming a successful startup entrepreneur. With $150 million raised, Ashok discusses the challenges and triumphs of disrupting the traditional employer...
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[$3 Trillion Market Revolution] Democratizing Structured Notes with Halo Investing
Join host Adam O'Donnell on the latest episode of Sit Down Startup. This week, Jason Barsema, a former financial advisor specializing in managing portfolios for ultra-high-net-worth individuals, has emerged as a groundbreaking figure in disrupting the structured notes market. Barsema initially...
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[4x Founder] From FBI to Founder: Jo Riley’s Journey to Product-Market Fit with Censia
Join us on the newest episode of Sit Down Startup as Jo Riley, founder of Censia, shares her inspiring journey from the FBI to launching a disruptive AI-driven platform. Host Adam O'Donnell and Jo discuss the importance of persistence, the value of customer feedback, and how Censia is…
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[$30B Market Reimagined] Unlocking Home Care's Potential with Honor
Welcome back to Sit Down Startup! Seth Sternberg, co-founder of Honor ($625M raised), a company dedicated to addressing the challenges faced by senior citizens during the COVID-19 pandemic, was heavily influenced by his upbringing in Connecticut and his entrepreneurial spirit. Sternberg's...
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[$400M raised] FLYR Labs’s Founder, Alex Mans: journey to product-market fit
Welcome to the latest episode of Sit Down Startup, where host Adam O'Donnell explores FLYR Labs’ founder and CEO Alex Mans' meteoric rise with $400M raised, #boom! Transitioning from a consumer-focused model predicting ticket prices to a B2B powerhouse, they're now strategically collaborating…
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[$80M+ raised] THAT Product-market fit moment: Avoid the analysis trap; Shippo’s Founder, Laura Behrens Wu
In this episode of Sit Down Startup, join Laura Behrens Wu, founder of the multimillion-dollar shipping platform Shippo, as she reveals the pivotal moments that led to staggering growth and product-market fit success. Discover Shippo's journey using customer retention tactics (8:12), an API-first...
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Trulia’s Founder; product-market-fit journey with Sami Inkinen
In the latest episode of Sit Down Startup, uncover Sami Inkinen's entrepreneurial journey, [00:11:28] beginning with how seizing the opportunity in his 20s set the stage for a phenomenal career. Sami shares his groundbreaking strides in [00:19:51] revolutionizing residential real estate with...
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Failed startup to $98M raised; Thoropass’s Founder, Sam Li shares their product-market-fit journey
Sam Li, co-founder and CEO of Thoropass, has a rich background. His perspective on achieving product-market fit as a startup founder is rooted in resourcefulness, curiosity, and adaptability. Here are some cool parts of the episode to check out! (00:02:18) Navigating Rookie Mistakes as a Founder...
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[$163M raised] Knowing you’ve hit product-market fit; Redpanda’s Founder, Alex Gallego
In this insightful episode, Red Panda's founder, Alex Gallego, embarks on a comprehensive exploration of the entrepreneurial journey. [00:02:33] He reveals the intertwining of personal struggles and leadership challenges, while advocating for a more supportive startup community. [00:10:36] Alex...
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[$100M+ raised] How to get product-market fit validation without an MVP
Sit Down Startup is back with Arjun Narayan, founder of Materialize, who shares how they nearly hit product-market fit before their MVP was ready! Host Adam O'Donnell dives into Arjun's journey from India to raising $100M+ (1:40) and revolutionizing real-time data processing with Materialize...
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[$217M raised] Stop convincing prospects and find the ones who get it: Sentry’s Founder, David Cramer
In this new episode of Sit Down Startup, Adam interviews Sentry's founder David Cramer, who shares insights from his illustrious journey that led to successfully raising $217 million. Tune in as David delves into diverse topics such as unraveling unique product monetization, cultivating…
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Arc’s $181M Success: Unity-Led-Growth with Founder, Don Muir
In this week's episode of Sit Down Startup, get to know Donald Muir, the creator and driving force behind Arc, a digital bank crafted for the tech-savvy crowd. As an experienced business leader with a keen desire for breakthroughs, Muir's interpretations of the explosion and teamwork in online...
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Bootstrapped to $40M and then raised $125M? Slice’s Founder, Ilir Sela
Join us for the latest episode of Sit Down Startup! Anyone want to order a pizza? You're in luck. This week's guest Ilir Sela is the founder and CEO of Slice, a platform that "builds innovative tech to empower America’s independent pizzerias." Sounds delicious! Ilir dives into... Fax-machine-MVP…
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[$150M raised] OpenStore’s Co-Founder, Jeremy Wood: Building the Right Engine: Overcoming Doubts
Jeremy Wood's solution, OpenStore, offers these founders the option to sell their businesses or have OpenStore operate and run the stores on their behalf. This innovative approach has not only provided a lifeline for many e-commerce founders but has also positioned OpenStore as a major player in...
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[$200M+ Raised] Self-Doubt & Worry to Thriving Through Startup Challenges; Electric.ai's Founder, Ryan Denehy
Ryan Denehy discussed the importance of overcoming self-doubt in the early stages of a startup. He shares his own experiences, practical advice, and data-driven insights that can help founders navigate the competitive business landscape. Thank you to this week's partners Aktie Now and WorknetGPT!...
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The Founder-led Content Formula; Atrium’s Founder Pete Kazanjy
Atrium, a software company co-founded by Pete Kazanjy in 2016, has achieved more business success with fewer Sales Development Representatives (SDRs). This accomplishment can be credited to their strong inbound game and their valuable content that educates and provides insights to their community...
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[$1.2B Val] Epidemic Sound's Founder, Oscar Hoglund: Overcoming Gov Regulations & Launching A Marketplace
The success of Epidemic Sound, a platform for content creators and music artists, is a testament to the skill, and creativity of Oscar Hoglund and his team. Despite the numerous legal and financial obstacles they encountered, they refused to give up on their mission and took the fight to Brussels...
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Tailscale's $113M Success: Developer-Led-Growth
Tailscale has been a huge success, raising over $113 million and growing to 80 employees. They discovered that if developers love the product, they will tell their decision makers in their organization to buy it, and the money will follow. To ensure customer satisfaction, they use Net Promoter...
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[$161M Raised] From Series A Struggles to 400 Employees: LinkSquares' Growth Strategies with Founder Vishal Sunak
Vishal Sunak, Founder of LinkSquares, shares his journey of building software for legal teams. Listen as he speaks to Sit Down Startup's host Adam O'Donnell about raising $161 million over five rounds of venture capital, overcoming fundraising struggles, and unlocking the secrets to growth....
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Bootstrapped to $100M+ Exit: Pardot’s Founder, David Cummings' Startup Journey
Join Adam O'Donnell on Sit Down Startup as he sits down with David Cummings, the founder of Pardot, which eventually sold to Salesforce. In this episode, they discuss pivoting from unsuccessful strategies, customer discovery, and marketing automation platform, while sharing their personal stories...
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Instacart's Former Chief Growth Officer; Building a Successful ML Startup: Anomalo's, Founder, Elliot Shmukler
Adam O'Donnell sits down with Elliot Shmukler, former Chief Growth Officer at Instacart and co-founder of Anomalo, to discuss the challenges data teams face in detecting and solving data quality issues using machine learning. Despite the initial failure of their product to meet customer needs,...
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$0 to 100M ARR in 18-months: Revolutionizing Cloud Security With Base Thinking; Wiz’s Co-Founder, Ami Luttwak
Welcome to the Sit Down Startup podcast, where host Adam O'Donnell interviews entrepreneurs and startup founders about their inspirational stories. In this episode, Adam brings in Ami Luttwak, the CTO and co-founder of Wiz, one of the largest cloud security companies. Ami shares the hands-on...
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($155M raised) Glean’s Founder, Arvind Jain: How to close enterprise deals from day one
Glean was founded in 2019 as an AI-powered workplace search engine aimed at helping people browse through their company apps to find the information they need and boost productivity. Since then, Glean has raised $155M+ and grown to 200+ employees while staying true to its initial mission. In this...
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Bootstrapped to nearly $100M exit to Citrix; Jesse Lipson; knowing when to ignore the “smart” advisors vs. just building
Jesse Lipson initially thought he would become a philosophy professor — until he took a job with a startup that changed his career path. After founding his first company Sharefile in 2005, he sold it to Citrix in late 2011 for almost $100M. And in October 2017 he established Levitate, which helps...
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[$271M raised] Frubana’s Founding Engineer, now board member, Daniel Bilbao; GTM tactics for $0 - $1M
During Truora’s first year, they raised no money. Four years later, this customer-engagement and WhatsApp-first startup has come a long way, with 8M USD in ARR, 14M USD in revenue, and presence across seven Latin American countries. Co-Founder and CEO Daniel Bilbao shares his tips for founders...
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Backed by a16z, Virtually Human Studio’s Co-Founder, Chris Ebeling: Building with community, listening vs. letting them lead
When Chris Ebeling co-founded entertainment company Virtually Human back in 2018, Blockchain was just becoming popular. Since then, the company has raised $21M+ and their online horse racing game ZED RUN gained an impressive following. In this episode, Chris talks to Adam about his experience...
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Zapier’s Founder: scalable growth strategies
Zapier has one mission: to help companies use automation to connect tools and apps so data can automatically move between them. The business was founded in 2012 and their remote team has since expanded worldwide across 40 countries. Founder Mike Knoop shared some takeaways from their 11-year...
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[$0 - IPO] Braze’s Founder, Mark Ghermezian; knowing when to pivot & the power of persistence
Back in 2008, when mobile apps were the talk of the town, Mark Ghermezian had an idea: build a bridge between app developers and users. That was the seed for Braze, a customer engagement platform, which has grown to 1200+ employees and 3.5M+ monthly active users. In this episode, Mark tells his...
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Talkdesk & Cleverly Co-Founder: Cristina Fonseca - Product obsessed, 5-min rule & not being distracted by competition
Cristina Fonseca, our very own VP of Product, knows a thing or two about being a founder. She has set up two companies specializing in CX: Talkdesk, back in 2011 (right after college!), which went on to raise over 250M USD; and Cleverly in 2017, now acquired by Zendesk. In this one-to-one with...
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[$396M Raised] Nailing pitch-market-fit? Eightfold AI’s CEO, Ashutosh Garg
When Ashutosh Garg founded talent intelligence platform Eightfold AI in 2016, he had one clear goal in mind: to help businesses hire and retain the best professionals out there. The company has since grown to almost 700 employees and has raised $400M. Ashutosh sat down to discuss Eightfold’s...
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[0-IPO] Yext’s Founder, Howard Lerman: key to building a lasting company
Howard Lerman founded tech company Yext in 2006, recording revenues of $100M during his final quarter as CEO. In November 2022, he started building his next project: Roam, an all-in-one Cloud HQ — and predicts it’s going to be even bigger. The entrepreneur joined Adam for a chat to share some key...
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[$0-IPO] Shift’s Co-Founder, Toby Russell; knowing when to pivot DESPITE having product-market-fit?!
In 2013, e-commerce platform Shift set out with one simple mission: to make car sales and purchases a seamless experience. The company began accelerating in late 2015 before they went public in 2020, and last year recorded revenues of 630M USD, selling vehicles in all 50 US states. Co-Founder…
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[$99M raised] Sweep’s Co-Founder, Rachel Delacour; listening for low signals during customer research to land big logos
Carbon emission tracking company Sweep was founded in June 2020. In just over two years, they have evolved to employ +80 people across Europe and the United States and, in less than 12 months, raised an impressive 100M USD. We sat down with Co-Founder & CEO, Rachel Delacour, who shared some key...
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[$600M+ raised] Deel’s Founder, Alex Bouaziz: pivoting with conviction
Founded in 2019 with the goal of offering a simple solution for hiring freelancers and contractors internationally, Deel pivoted just a week before demo day. They restructured their program and grew to over 1,900 employees, 10K+ customers worldwide and raised $600M+. Here are the key takeaways…
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[$1.6B val] Mercury’s Founder, Immad Akhund; rapid growth via word of mouth
Mercury, a banking service for startups, was launched in 2019 but their business idea had been brewing since 2013. Mercury has now grown to 357 employees and tens of thousands of customers. CEO & Co-Founder Immad Akhund joined us to share some advice: Classic strategies work. Encourage your...
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[$1.2B val] Pilot’s CEO, Waseem Daher; knowing where to stay in the weeds
Founded in 2017, Pilot is a platform that offers bookkeeping, tax and CFO services for growing businesses. From a team of 10 to now 400, Pilot helps thousands of startups — crediting their speed, responsiveness and going above and beyond for customers as key to their growth. We sat down with CEO…
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[Acquired by Apple] Beats by Dre’s Omar Johnson on building a brand and standing out
In 2010, Beats by Dre saw a huge opportunity to pivot and make a mark. They were able to uniquely combine the world of sports and music in a way people hadn’t seen before. A clear vision and authentic messaging helped differentiate themselves. We talked with former CMO, Omar Johnson, who shared...
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ABOUT THIS SHOW
Here’s how to startup. Even when the world goes topsy-turvy. From one home office to another, Zendesk leaders chat with founders, CEOs, and makers on their startup journey. There’s rule-flipping, new dogma and recycling failure into growth. Plus, why customer experience is at the heart of success, as told by people who know unpredictability inside out. (That seems pretty helpful right now.)
HOSTED BY
Adam O'Donnell
CATEGORIES
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Frequently Asked Questions
How many episodes does Sit Down Startup have?
Sit Down Startup currently has 105 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Sit Down Startup about?
Here’s how to startup. Even when the world goes topsy-turvy. From one home office to another, Zendesk leaders chat with founders, CEOs, and makers on their startup journey. There’s rule-flipping, new dogma and recycling failure into growth. Plus, why customer experience is at the heart of success,...
How often does Sit Down Startup release new episodes?
Sit Down Startup publishes regularly with 105 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Sit Down Startup?
You can listen to Sit Down Startup on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Sit Down Startup?
Sit Down Startup is created and hosted by Adam O'Donnell.
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