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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.)
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Startup Grind

www.startupgrind.com

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Startup Grind is the world’s largest community of startups, founders, innovators, and creators. We bring like-minded yet diverse individuals together to connect, learn, teach, help, build, and belong. We do this daily through our local events, flagship conferences, startup program, partnerships, and online media + content - collectively reaching over 3.5 million individuals worldwide.
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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 and simplifying access to DeFi investments. He discus…
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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 feedback and recruit talent in an increasingly compet…
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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, adaptability, and the necessity of continuous product e…
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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 the importance of continuous product evolution, and hea…
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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 Harvard, and how that paved the way for the creation of …
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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 tech space, emphasizing the importance of capturing com…
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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 fit in financial technology. He also emphasizes the imp…
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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 health insurance market to make healthcare affordable fo…
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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 sought to eliminate the counterparty risk of big banks …
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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 transforming the way companies find and manage talent. Whether y…
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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 experiences during the pandemic greatly shaped his perspecti…
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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 with airlines to optimize pricing. Adam and Alex discuss…
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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 strategy (13:33), and conquering the Shopify App Sto…
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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 interactive maps, helping Trulia achieve an unparalleled …
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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 (00:07:48) The Importance of Intellectual Honesty in …
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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 unpacks his ever-evolving CEO priorities; from achievi…
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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 (00:45). Founders will appreciate the dialogue on tech da…
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His journey started when he started building products & wrote blogs for different companies - he was in New Zealand. He was the first writer for Mashable. All of this while he was just 14! After sometime, he joined Teachable as a founding engineer. He grew in his role all the way to VP of product & with teachable doing reasonably well - he thought …
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I recorded this episode in Delhi - what a time to record! We started with the impact of AQI on lifespan & talk about the impact of pincode on your lifespan. Longevity feels like a field where you need to spend a ton of time in research but Alex shared his views on how we can get started with a lot less. It was interesting to get his thoughts on how…
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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 unwavering belief in success (00:05:41), the power of focus an…
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We talk about the myths around remote work, how do we build the right culture at the company & deep dive into tons of challenges that becomes excuses for many to call their employees back to office. Some of the points we discussed include: Building the right culture Growing the team remotely Offsites or no offsited Cross team collaboration Global c…
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Following his remarkable success with the $780M acquisition of his startup, Vungle, by private equity giant Blackstone in 2019, Zain founded Zain Ventures, a family office with a diverse portfolio spanning various asset classes. Zain's investment philosophy is straightforward: strategically allocate capital to the right fund managers and partner wi…
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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 banking post-SVB collapse (2:45) come from his hands-on…
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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 - meet the customer where they are Why he bootstrappe…
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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 the e-commerce market. Join Adam O'Donnell and Jeremy…
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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! Aktie Now has a special offer for startups joining t…
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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 of 35,000 members. Atrium's software helps businesse…
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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 to change copyright laws and protect artists from ex…
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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 Score to move people from the middle to the top and off…
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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. Discover the importance of building a strong product, foun…
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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 of startup challenges.…
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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, Anomalo was able to grow 10x ARR during the big recessi…
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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 culture of the company, where all managers do the work th…
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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 episode its founder, Arvind Jain, shares his experie…
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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 relationship-based businesses keep in touch with cli…
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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 looking to succeed: Hire the best people you can. Talen…
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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 launching in the digital world and shares a few tips: In…
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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 journey so far: Stay patient. Growth is organic, so be pr…
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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 story and teaches us a few lessons: Iteration is key. …
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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 Adam, she shares her experience: Build trust. Stay pres…
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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 journey with Adam, sharing a few learnings along the way:…
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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 insights and strategies from his +20 years’ experien…
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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 Toby Russell joined Adam to share a few insights from th…
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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 learnings: Test your product with friends. Get in touc…
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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 from our chat with Co-Founder & CEO, Alex Bouaziz: Time…
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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 investors to talk about you on social media to get word-of…
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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 & Co-Founder, Waseem Daher, who shared his biggest ta…
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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 insights from Beats’ early days: Set clear objectives.…
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In only three years, financial planning company Origin grew from 20 to more than 150 employees and raised over 70 million USD. While only beginning their journey, the company — created to help employers answer their employees’ tough questions about financial benefits — has found success by focusing on solutions for real-world problems. We sat down …
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In March 2020, everything stopped for events company Bizzabo. So they quickly pivoted and designed a new product for the times we were living in — pairing in-person conference tools with a virtual event management platform. With offices spanning the globe and a team from all walks of life, the company is united by one mission: to define the future …
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