92 episodes

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.)

Sit Down Startup Adam O'Donnell

    • Business
    • 5.0 • 46 Ratings

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.)

    [$150M Raised] Navigating Product-Market Fit in Healthcare: Ashok Subramanian on Building Centivo

    [$150M Raised] Navigating Product-Market Fit in Healthcare: Ashok Subramanian on Building Centivo

    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 perseverance and innovation. He also delves into the nuances of achieving product-market fit, the importance of character and integrity in business, and the lessons learned along the way. Tune into Adam O'Donnell's latest founder interview to gain valuable insights and inspiration from Ashok's remarkable entrepreneurial journey.

    (00:04:37) Affordable Healthcare Solutions for Underserved Americans
    (00:11:29) Scaling Success: A Multi-Year Journey
    (00:16:02) Optimizing Founder Time Allocation for Growth Strategy
    (00:20:58) Navigating Entrepreneurial Hurdles for Startup Success

    Qualifying startups can use Zendesk six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

    • 23 min
    [$3 Trillion Market Revolution] Democratizing Structured Notes with Halo Investing

    [$3 Trillion Market Revolution] Democratizing Structured Notes with Halo Investing

    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 strategically pivoted to enhance the efficiency and accessibility of structured notes, much like Netflix adapted its model in response to technological constraints. This shift led to the creation of Halo, a platform that democratizes access to structured notes, making them available to retail investors and addressing the savings crisis, thus revolutionizing a $3 trillion market.

    (00:03:18) Revolutionizing Structured Notes Accessibility Through Innovation(00:08:45) Efficient Structured Notes Revolutionize Financial Products Market(00:13:24) Structured Notes: The Path to Profitability(00:18:23) Leveraging Financial Advisors for Business Growth Strategy
    Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

    • 23 min
    [4x Founder] From FBI to Founder: Jo Riley’s Journey to Product-Market Fit with Censia

    [4x Founder] From FBI to Founder: Jo Riley’s Journey to Product-Market Fit with Censia

    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 - Background: Jo’s early life and introduction to intelligence.
    00:04:25 - Transition from the FBI to entrepreneurship.
    00:10:45 - The turning point and early struggles in raising venture capital.
    00:12:24 - Hitting product-market fit and scaling Sentia.
    00:29:58 - Using customer feedback to guide product development.

    Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

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

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

    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 older adults, Sternberg was faced with the realization of potential risks and the survival of the company.
    Despite these daunting challenges, Sternberg emphasized the necessity of resilience, adaptability, and finding creative solutions to ensure the safety of both employees and clients. Implementing strict infection control protocols and policies, Sternberg showcases his deep-rooted motivation to contribute positively to society, especially during times of crisis.

    Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

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

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

    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 strong personal relationships FLYR Labs has forged with airline C-suite executives, key in securing lucrative contracts. Finally, Adam and Alex tackle the criticism airlines face for poor data management and how FLYR Labs' machine learning solutions are setting new industry standards.

    Don't miss this high-altitude discussion!

    Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

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

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

    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 the competitive e-commerce space.

    Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

    • 41 min

Customer Reviews

5.0 out of 5
46 Ratings

46 Ratings

Dan1777999877 ,

Love this show!

No matter the subject, you’re guaranteed to gain something from every episode - can’t recommend Sit Down Startup enough. 🙌

nawDoode ,

Smart tactics very accessible

Adam and his guests are so strategic and transparent ! They share growth practices that work and are insightful for anyone growing a business. This podcast is so juicy I listen with a napkin and a notepad ready to ask for seconds!

Donald1503 ,

Amazing content for early stage founders

I’m in process of launching my startups and this show is helping me a ton. It’s amazing to hear from these leaders on how they are investing in customer experience.

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