Sit Down Startup

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 hi...

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 sh...

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 M...

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 inva...

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 insigh...

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 langu...

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 durin...

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 fa...

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 a...

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 trans...

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...

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. H...

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 poin...

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, t...

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 stru...

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...

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 signific...

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 st...

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:...

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, [0...

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 Pivoting (00:12:36) Discovering Customer Pain Poin...

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 achieving product-market fit in the early stages to focus...

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 database funding and the role of investor...

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 and core concepts (00:08:45), and managing feedback...

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 experience of building Arc from scratch. Muir und...