Sit Down Startup

May 15 2024 4
Sit Down Startup Podcast artwork

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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[$30B Market Reimagined] Unlocking Home Care's Potential with Honor

May 15 2024 32 mins  
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. Acknowledgin

[$400M raised] FLYR Labs’s Founder, Alex Mans: journey to product-market fit

Mar 20 2024 38 mins  
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, rec

[$80M+ raised] THAT Product-market fit moment: Avoid the analysis trap; Shippo’s Founder, Laura Behrens Wu

Feb 21 2024 41 mins  
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

Trulia’s Founder; product-market-fit journey with Sami Inkinen

Feb 08 2024 42 mins  
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

Failed startup to $98M raised; Thoropass’s Founder, Sam Li shares their product-market-fit journey

Jan 24 2024 22 mins  
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 Custo

[$163M raised] Knowing you’ve hit product-market fit; Redpanda’s Founder, Alex Gallego

Jan 10 2024 22 mins  
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 s

[$100M+ raised] How to get product-market fit validation without an MVP

Dec 06 2023 28 mins  
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 r

[$217M raised] Stop convincing prospects and find the ones who get it: Sentry’s Founder, David Cramer

Nov 08 2023 30 mins  
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 ma

Arc’s $181M Success: Unity-Led-Growth with Founder, Don Muir

Oct 25 2023 23 mins  
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 s

Bootstrapped to $40M and then raised $125M? Slice’s Founder, Ilir Sela

Oct 04 2023 26 mins  
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 areWhy he bootstrapped to $40M GMV vs. raising soonerWh