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PODCAST

Sit Down Startup

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.)

business management

All Episodes

18:47

[$10M+ Raised] Mark Doble, Co-Founder of Alexi, on...

Sit Down Startup ·

2025/02/12

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 Mark shares his experiences transitioning from law to entrepreneurship, the pivotal moments that tested his resolve, and how Alexi is revolutionizing legal research through innovative AI solutions. He emphasizes

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22:23

[Harnessing AI Technology for Business Growth]...

Sit Down Startup ·

2025/01/29

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 AppDirect, which has grown into a unicorn valued at over half a billion dollars, and how those experiences shaped his current venture, Landbase.Discover the pivotal moments during the early days of AppDirect,

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22:51

[Sustaining Competitive Edge] CEO Randy Wootton of...

Sit Down Startup ·

2025/01/15

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 military leadership to the helm of a transformative billing and revenue management company. He discusses how Maxio is redefining the standards of product-market fit, particularly in a market increasingly influenced

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24:31

[$121.5M in Funding] Efficient Capital Labs' Kaustav...

Sit Down Startup ·

2024/12/11

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 of cross-border financing and the critical importance of achieving product-market fit.Discover the invaluable insights Kaustav gained about understanding customer pain points, the challenges of raising

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27:35

[Pioneering Retail Innovation] CEO Angie Westbrock on...

Sit Down Startup ·

2024/11/27

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 from autonomous checkout to leveraging computer vision for retail analytics, unlocking valuable insights for retailers. Angie shares her experiences navigating the challenges of product-market fit, the

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24:18

[$30M Raised] Transforming Legal Tech: Spellbook...

Sit Down Startup ·

2024/11/13

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 resilience, the struggles of achieving product-market fit, and the transformative power of large language models in revolutionizing legal document management. Learn how Spellbook, which has raised over $30

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25:20

[Transforming Crypto Access] Co-Founder/CEO Driss...

Sit Down Startup ·

2024/10/30

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 discusses the importance of maintaining conviction during tough times and the pivotal moment that led to the creation of their innovative risk assessment tool,

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25:37

[Navigating the AI Landscape] Co-Founder and CEO...

Sit Down Startup ·

2024/10/10

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 competitive landscape.Discover the challenges Jensen faced during the early days of Textio, including navigating the uncertainties of the COVID-19 pandemic, and

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26:24

[~$100M Raised] Transforming Talent Assessment:...

Sit Down Startup ·

2024/09/25

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 evolution. Learn how CodeSignal, which has raised almost $100M, achieved product-market fit by shifting focus to advanced talent assessment tools.Here's the

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21:50

[Revolutionizing Climate Tech] Sealed’s co-founder...

Sit Down Startup ·

2024/09/12

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 hear how Sealed found its product-market fit by transitioning from in-person sales to a streamlined phone-based sales process. The lesson? Sometimes you need

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23:45

[$300M Raised] Mapping the Human Immune System for...

Sit Down Startup ·

2024/08/28

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 Immunai. Learn about the challenges of navigating product-market fit in the deep science space and the responsibility that comes with managing significant

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20:27

[90% of Co-Founder's Time Spent Speaking to...

Sit Down Startup ·

2024/08/14

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 comprehensive home data to support decision-making. His journey, marked by early-stage company experiences and real estate investment, shaped his belief in

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25:21

[$0 to $20M ARR in 1 year] Creating a Path to...

Sit Down Startup ·

2024/07/31

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 importance of listening closely to the core pain points of customers, such as financial stress from living paycheck to paycheck, lack of credit score, and

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23:54

[$150M Raised] Navigating Product-Market Fit in...

Sit Down Startup ·

2024/07/17

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 for all. From his early days in Buffalo, New York, to obtaining his MBA at Stanford, and eventually founding Centivo, Ashok's story is a testament to

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23:54

[$3 Trillion Market Revolution] Democratizing...

Sit Down Startup ·

2024/06/26

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 by using listed options and cash to replicate structured notes, but faced challenges in product adoption due to custodial limitations. Undeterred, he

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41:30

[4x Founder] From FBI to Founder: Jo Riley’s Journey...

Sit Down Startup ·

2024/06/05

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 you're a founder or an aspiring entrepreneur, Jo's story of resilience, innovation, and customer obsession provides invaluable insights.00:01:08 -

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32:16

[$30B Market Reimagined] Unlocking Home Care's...

Sit Down Startup ·

2024/05/15

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 perspective on its challenges. Acknowledging the significant impact of the pandemic on his business, which involves sending care professionals into the homes of

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38:21

[$400M raised] FLYR Labs’s Founder, Alex Mans:...

Sit Down Startup ·

2024/03/20

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 why pivoting to high-margin, recurring revenue streams with big companies was a game-changer for their business model.Also critical to success are the

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41:37

[$80M+ raised] THAT Product-market fit moment: Avoid...

Sit Down Startup ·

2024/02/21

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 Store with a savvy inbound marketing approach (00:35:15). Listen to this interview for a deep dive into the game-changing approaches Shippo took to thrive in

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42:49

Trulia’s Founder; product-market-fit journey with...

Sit Down Startup ·

2024/02/08

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 product-market fit. Venturing into health tech, [00:36:53] Sami discusses Virta Health's mission to reverse diabetes through nutrition, not

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105 results

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