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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We unfold the story behind industry-leading fitness entrepreneurs, sharing the trials and tribulations faced on their journey to success in order to pave the way for aspiring fitness entrepreneurs.
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[$300M Raised] Mapping the Human Immune System for Drug Discovery: Noam Solomon on Building Immunai
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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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[90% of Co-Founder's Time Spent Speaking to Customers] How Inspectify has Navigated Startup Success
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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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[$0 to $20M ARR in 1 year] Creating a Path to Financial Empowerment with Brigit's co-founder and CEO Zuben Mathews
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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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[$150M Raised] Navigating Product-Market Fit in Healthcare: Ashok Subramanian on Building Centivo
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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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[$3 Trillion Market Revolution] Democratizing Structured Notes with Halo Investing
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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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[4x Founder] From FBI to Founder: Jo Riley’s Journey to Product-Market Fit with Censia
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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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[$30B Market Reimagined] Unlocking Home Care's Potential with Honor
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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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[$400M raised] FLYR Labs’s Founder, Alex Mans: journey to product-market fit
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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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[$80M+ raised] THAT Product-market fit moment: Avoid the analysis trap; Shippo’s Founder, Laura Behrens Wu
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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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Trulia’s Founder; product-market-fit journey with Sami Inkinen
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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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Failed startup to $98M raised; Thoropass’s Founder, Sam Li shares their product-market-fit journey
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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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[$163M raised] Knowing you’ve hit product-market fit; Redpanda’s Founder, Alex Gallego
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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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[$100M+ raised] How to get product-market fit validation without an MVP
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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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[$217M raised] Stop convincing prospects and find the ones who get it: Sentry’s Founder, David Cramer
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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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Arc’s $181M Success: Unity-Led-Growth with Founder, Don Muir
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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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Bootstrapped to $40M and then raised $125M? Slice’s Founder, Ilir Sela
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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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[$150M raised] OpenStore’s Co-Founder, Jeremy Wood: Building the Right Engine: Overcoming Doubts
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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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[$200M+ Raised] Self-Doubt & Worry to Thriving Through Startup Challenges; Electric.ai's Founder, Ryan Denehy
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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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The Founder-led Content Formula; Atrium’s Founder Pete Kazanjy
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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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[$1.2B Val] Epidemic Sound's Founder, Oscar Hoglund: Overcoming Gov Regulations & Launching A Marketplace
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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's $113M Success: Developer-Led-Growth
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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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[$161M Raised] From Series A Struggles to 400 Employees: LinkSquares' Growth Strategies with Founder Vishal Sunak
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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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Bootstrapped to $100M+ Exit: Pardot’s Founder, David Cummings' Startup Journey
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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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Instacart's Former Chief Growth Officer; Building a Successful ML Startup: Anomalo's, Founder, Elliot Shmukler
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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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$0 to 100M ARR in 18-months: Revolutionizing Cloud Security With Base Thinking; Wiz’s Co-Founder, Ami Luttwak
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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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($155M raised) Glean’s Founder, Arvind Jain: How to close enterprise deals from day one
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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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Bootstrapped to nearly $100M exit to Citrix; Jesse Lipson; knowing when to ignore the “smart” advisors vs. just building
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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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[$271M raised] Frubana’s Founding Engineer, now board member, Daniel Bilbao; GTM tactics for $0 - $1M
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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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Backed by a16z, Virtually Human Studio’s Co-Founder, Chris Ebeling: Building with community, listening vs. letting them lead
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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’s Founder: scalable growth strategies
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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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[$0 - IPO] Braze’s Founder, Mark Ghermezian; knowing when to pivot & the power of persistence
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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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Talkdesk & Cleverly Co-Founder: Cristina Fonseca - Product obsessed, 5-min rule & not being distracted by competition
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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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[$396M Raised] Nailing pitch-market-fit? Eightfold AI’s CEO, Ashutosh Garg
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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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[0-IPO] Yext’s Founder, Howard Lerman: key to building a lasting company
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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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[$0-IPO] Shift’s Co-Founder, Toby Russell; knowing when to pivot DESPITE having product-market-fit?!
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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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[$99M raised] Sweep’s Co-Founder, Rachel Delacour; listening for low signals during customer research to land big logos
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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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[$600M+ raised] Deel’s Founder, Alex Bouaziz: pivoting with conviction
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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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[$1.6B val] Mercury’s Founder, Immad Akhund; rapid growth via word of mouth
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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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[$1.2B val] Pilot’s CEO, Waseem Daher; knowing where to stay in the weeds
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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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[Acquired by Apple] Beats by Dre’s Omar Johnson on building a brand and standing out
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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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[$70M+ raised] Origin’s Matt Watson on finding clarity to target problems
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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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[$194M raised] Bizzabo’s Alon Alroy on pivoting early and fast
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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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[3M+ users] BharatAgri’s Founder, Sai Gole: micro influencers as a GTM channel
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BharatAgri began as a college project back in 2015 and came to reality when they launched in 2017. Since then, the company has stuck to their mission of being the bridge between tech and farming. Today, their app has over 100K subscribers and is available across India. Co-Founder & CEO Sai Gole gives us a glimpse of their journey: Think outside the…
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[$98M raised] Paystand’s Founder, Jeremy Almond; meet them where they are > selling a cool tech idea
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When digital B2B payment service Paystand launched in 2013, it had one mission: to democratize commercial payments. Today, the company has over 400,000 businesses making payments through their network, as well as $4B of volume on the block chain. Co-Founder & CEO Jeremy Almond joins Adam to give some advice: Stay true to your mission. Imagine the w…
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[$164M+ Raised] Aisera’s Muddu Sudhakar on fundraising the right way
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Since launching in late 2017, AI service experience startup Aisera successfully raised over $164M from VCs such as Zoom, Menlo Ventures, First Round Capital and Norwest Ventures — helping them grow to the +180 employee company they are today. Co-Founder and CEO Muddu Sudhakar gives his tips on fundraising: Vision is everything. Make sure your inves…
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[Ukrainian Founder] Fuel Finance’s Alyona Mysko; growth during a war
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It’s been a rocky two years since Ukrainian cloud-based financial company Fuel Finance opened their doors. In 2022, they faced the toughest challenge yet — the invasion of their home country. Here’s what Co-Founder & CEO Alyona Mysko had to say: Adapt your priorities. When times of uncertainty hit, it’s important to look out for your family and tea…
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[$LFLY] Leafly’s Founder, Cy Scott - don’t hack everything & knowing which battles to fight
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20:41
This week Adam sat down with Cy Scott, Co-Founder of Leafly — think Yelp, but for cannabis — now a publicly traded company listed on the NASDAQ ($LFLY). Here are some key learnings: Be smart about hacks — know when and when not to do them. In the long term, doing things the right way can bring far better results than cutting corners! Keep user expe…
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[$73M+ Raised] Pair Eyewear’s Nathan Kondamuri - customer discovery & GTM wins
20:46
20:46
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Gillad
20:46
When Pair Eyewear first started, their focus was on making glasses a fun and dynamic accessory for kids. Today, they provide frames for everyone and employ over 90 people across the U.S. In this episode, Co-Founder and Co-CEO Nathan Kondamuri shares their journey as we discuss: The importance of evaluating possible paths when opportunities arise Ho…
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Carrot Fertility’s Tammy Sun on knowing your business inside and out
20:25
20:25
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Gillad
20:25
Tammy Sun co-founded Carrot Fertility in 2016 with a mission to provide personalized fertility benefits for everyone, regardless of age, race, sexual orientation, income or geography. Since then, the company has gone global and their services are available in over 120 countries. Adam sat down with Tammy to get her take on: Why you should always lis…
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Swag.com’s Jeremy Parker on targeting the top from the get-go
17:42
17:42
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17:42
Jeremy Parker made the unusual switch from documentary filmmaker to entrepreneur in 2007 and hasn’t looked back. Since then, he founded promotional product platform Swag.com in January 2016, before it was acquired by major online apparel retailer Custom Ink in 2021. Adam sat down with Jeremy for a virtual chat to get the stories behind: How Swag.co…
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