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 empha...
Feb 12, 2025•19 min•Season 9Ep. 3
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,...
Jan 29, 2025•22 min•Season 9Ep. 2
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 influe...
Jan 15, 2025•23 min•Season 9Ep. 1
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 c...
Dec 11, 2024•25 min•Season 8Ep. 33
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 ...
Nov 27, 2024•28 min•Season 8Ep. 32
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 ...
Nov 13, 2024•24 min•Season 8Ep. 31
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 to...
Oct 30, 2024•25 min•Season 8Ep. 30
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...
Oct 10, 2024•26 min•Season 8Ep. 29
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...
Sep 25, 2024•26 min•Season 8Ep. 28
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 ...
Sep 12, 2024•22 min•Season 8Ep. 27
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 signifi...
Aug 28, 2024•24 min•Season 8Ep. 26
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 ...
Aug 14, 2024•20 min•Season 8Ep. 25
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, an...
Jul 31, 2024•25 min•Season 8Ep. 24
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 pe...
Jul 17, 2024•24 min•Season 8Ep. 23
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 ...
Jun 26, 2024•24 min•Season 8Ep. 22
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 - Bac...
Jun 05, 2024•42 min•Season 8Ep. 21
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...
May 15, 2024•32 min•Season 8Ep. 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 t...
Mar 20, 2024•38 min•Season 8Ep. 19
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 thriv...
Feb 21, 2024•42 min•Season 8Ep. 18
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 pharmaceut...
Feb 08, 2024•43 min•Season 8Ep. 17
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 Points for Product Market Fit (00:19:50) Framework Thinking and Curiosity: Sam Li's Superpowers Apply to...
Jan 24, 2024•22 min•Season 8Ep. 16
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 focusing on team recruitment and understanding market structure later on. [00:18:49] He underscores the c...
Jan 10, 2024•22 min•Season 8Ep. 15
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 expertise (16:16). Tune in for more! Shoutout to this episode's partners Capchase and FounderPass! Capchase - ...
Dec 06, 2023•28 min•Season 8Ep. 14
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 at scale (00:18:37). The conversation touches upon customer engagement wisdom: distinguishing valuab...
Nov 08, 2023•31 min•Season 8Ep. 13
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 underlines the value of a dynamic digital bank that blends the personalized touch of a bank like First ...
Oct 25, 2023•24 min•Season 8Ep. 12
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 bootstrapped to $40M GMV vs. raising sooner What he looked for in a VC partner And more! Shoutout to our partners DocSend and The Launch Box! DocSend: DocSend al...
Oct 04, 2023•27 min•Season 8Ep. 11
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 Wood as they delve deeper into this topic on the next episode of Sit Down Startup. Lark is a next-generation team productivity suite that boosts orga...
Sep 06, 2023•24 min•Season 8Ep. 10
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 the Zendesk for Startups program: Zendesk Express implementation - Have your Zendesk up and running, fully configured to your processes, including trai...
Aug 24, 2023•22 min•Season 8Ep. 9
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 businesses implement data-driven sales management by monitoring KPIs and providing alerts. Host Adam O'Donnell also discusses the challenges of business growth...
Aug 09, 2023•23 min•Season 8Ep. 8
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 exploitation. The key to their success was their passion for the project and the support of those around them. Through their dedication, they were able ...
Jul 26, 2023•28 min•Season 8Ep. 7
