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Designing Successful Startups

Designing Successful Startups

Written by: Jothy Rosenberg
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Professor-turned-entrepreneur, and founder of nine companies, Jothy Rosenberg talks with business leaders and personal achievers. A companion to his book Tech Startup Toolkit, the “Designing Successful Startups” podcast tells the stories of Jothy's guests as they took on the challenges of building a new startup. The lessons conveyed come from both things done right and things done wrong that can help listeners learn the best way to design their own startups to be successful. Along the way this show explores the challenges and rewards of entrepreneurship, overcoming adversity, and where grit and perseverance can get you. Be inspired by others, and push yourself along your path to success and fulfillment.Copyright 2026 Jothy Rosenberg Economics Hygiene & Healthy Living Leadership Management & Leadership Psychology Psychology & Mental Health Self-Help Success
Episodes
  • The Librarian Who Wants You to Slow Down—Why 95% of AI Implementations Fail
    Jan 21 2026

    Jill Heinze

    Bio

    Jill Heinze helps startups turn AI risks into competitive advantages. A former academic librarian turned AI strategist, she founded Saddle-Stitch Consulting after spending two decades in market research, competitive intelligence, and digital strategy. As former Research Director at a major consultancy, she built responsible AI frameworks for Fortune 500 clients and founded the firm's first executive AI governance committee. Her superpower? Using research methods to uncover real risks before they become expensive problems. She hosts Responsible Tech Talks on LinkedIn Live and serves as Responsible AI Program Director for the American College's Cary M. Maguire Center for Ethics in Financial Services.

    Intro

    Jill Heinze, the founder of Saddle Stitch Consulting and a distinguished UX researcher, elucidates the critical intersection of technology and human experience in our discussion. She emphasizes that the rapid advancement of AI should not eclipse our responsibility to consider its impact on individuals and society at large. Throughout the conversation, Jill highlights a staggering statistic: 95% of organizations fail to achieve return on investment from their AI initiatives, attributing this failure to a lack of understanding of user needs and the inherent risks of technology implementation. We delve into the imperative for founders to engage with their teams and audit AI usage within their organizations to mitigate potential pitfalls. Ultimately, Jill advocates for a paradigm shift in how we approach technology, urging us to prioritize thoughtful engagement over reckless acceleration.

    The dialogue with Jill Heinze, a prominent figure in user experience research and the founder of Saddle Stitch Consulting, unfolds a critical examination of the intersection between technology and human experience in the context of artificial intelligence. Jill articulates a profound concern: the hasty deployment of AI technologies without a thorough understanding of their implications poses substantial risks not only to organizations but also to the individuals who interact with these technologies on a daily basis. Through her extensive background as a librarian and UX researcher, she underscores the necessity of grounding technology in real human experiences rather than abstract notions. Her insights urge founders to prioritize the well-being of users and to engage deeply with the communities affected by their technological innovations. In a landscape where 95% of organizations reportedly fail to realize a return on investment from AI initiatives, Jill's perspective becomes an invaluable guide for those looking to navigate the complexities of integrating AI responsibly. She emphasizes the importance of asking critical questions about the potential repercussions of new technologies and advocates for a shift in mindset from mere risk management to recognizing opportunities within those risks.

    The episode serves as a clarion call for a more human-centric approach to technology, reminding us that the decisions we make in the realm of AI will shape our collective future. The conversation with Jill Heinze delves into the often-overlooked aspect of technology's impact on human lives, presenting a compelling case for responsible AI implementation. Jill shares her journey from librarian to UX director and now to founder, highlighting the lessons learned along the way. She reflects on the inherent unpredictability of technology and the necessity of embedding a human perspective in AI governance. The discussion reveals that technology does not exist in isolation; rather, it interacts with human behaviors, expectations, and societal norms. Jill's experiences illuminate the challenges faced by organizations that move too quickly without proper consideration of...

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    39 mins
  • Anxious and Building Anyway: How Emily Smith Turned Fear Into Startup Fuel`
    Jan 7 2026

    Emily Smith

    Bio

    Emily Smith founded Side Nerd Apps to make building a custom, accurate, integrated chatbot as simple as creating a website. Drawing on her analytics background and years of volunteer work, she helps small and midsize businesses deliver software that’s accessible and user-friendly, even for people who want nothing to do with traditional tech.

    Intro

    The focal point of our discussion in this episode revolves around the essential truth that the technological frameworks underpinning our society—specifically applications and websites—often alienate significant segments of the population. My esteemed guest, Emily Smith, founder of Side Nerd, elucidates her profound understanding of this issue, drawing from her extensive experience in the startup environment. Emily’s journey began with her involvement in various startups, where she honed her skills and acquired a unique perspective on the challenges faced by individuals who struggle with technology. Through her innovative venture, Side Nerd, she aims to create user-friendly solutions that simplify data entry processes, thereby making technology more accessible to all. Throughout our conversation, we delve into the complexities of entrepreneurship, the vital importance of understanding user needs, and the transformative potential of designing technology that genuinely serves its users.

    Conversation

    The conversation between Jothy Rosenberg and guest Emily Smith delves into the intricacies of technology and its accessibility, particularly within the context of her startup, Side Nerd. Emily elucidates that many individuals in society find the technological landscape, characterized by applications and systems, to be daunting and often exclusionary. This conversation is particularly relevant as it sheds light on the pervasive challenges that hinder user engagement with technology, which, ironically, is designed to enhance user experiences. Emily emphasizes that the discomfort associated with technology is not merely a personal failure but a widespread issue that affects numerous individuals, particularly those who feel marginalized or inadequate in their technological capabilities.

    Emily recounts her journey into the world of startups, revealing her early experiences with a grocery delivery service that ultimately failed when Amazon acquired Whole Foods. This setback, however, became a catalyst for her entrepreneurial spirit, instilling in her the belief that in the startup ecosystem, one must take initiative to solve problems independently. This mentality birthed the concept of Side Nerd, a tool designed to simplify the interaction with complex systems like Salesforce, allowing users to engage in data entry through natural language via text. The goal is to transform the user experience from one of frustration to ease, thereby empowering individuals who may otherwise feel alienated by technology.

    Furthermore, Emily provides an insightful reflection on the notion of grit in entrepreneurship, identifying it as a product of both her personal struggles with anxiety and her unwavering determination to solve meaningful problems. By embracing discomfort and pushing through fear, she has cultivated resilience that allows her to navigate the tumultuous landscape of startup development. This episode serves as an inspiration for aspiring entrepreneurs, illustrating the importance of perseverance, the necessity of user-centric design, and the profound impact of addressing accessibility in technology.

    In summary, the dialogue encapsulates the essence of entrepreneurship: the pursuit of innovative solutions to existing problems while fostering inclusivity within the technological realm. Emily's insights not only highlight the significance of...

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    40 mins
  • From the Principal's Office to 100 Episodes: Luis Derechin on Grit, Talent, and Going Global
    Dec 17 2025

    Luis Derechin

    Bio

    Luis Derechin is a serial entrepreneur, global talent strategist, and author of "The Nearshore Edge: How Smart Companies Scale With Latin American Talent." As the founder and CEO of Nir-Yu, Luis created the REMOTE Intelligence framework, helping ambitious startups and mid-market enterprises access top talent while cutting costs by up to 70%.

    Intro

    The salient point of today's discussion is that a staggering 73% of offshore or nearshore projects culminate in failure, a statistic that underscores the critical need for a paradigm shift in hiring practices for startups. I, Jothy Rosenberg, am joined by the esteemed Luis Derechin, a repeat entrepreneur who has navigated the complexities of building successful teams across borders. Luis shares his transformative revelation that extending a startup's runway is not solely reliant on securing additional funding, but rather hinges on rethinking talent acquisition strategies. By leveraging the vast pool of world-class talent available in Latin America, companies can dramatically reduce operational costs while fostering real-time collaboration. This episode, marking our centenary, is a profound exploration of effective hiring practices that can significantly enhance a startup's prospects for success.

    Conversation

    The conversation with Luis Derechin, a seasoned entrepreneur and founder of Nir-yu, delves into the pressing issue of talent acquisition in the startup ecosystem. With a staggering 73% of offshore projects failing, Derechin posits that the solution to extending a startup's runway may not lie solely in securing additional funding but rather in strategically rethinking hiring practices. He shares his personal journey from selling candy as a child to successfully raising venture capital for his tech startup in Mexico. Derechin advocates for hiring Latin American talent, which not only reduces costs significantly but also facilitates real-time collaboration across time zones, thereby enhancing the effectiveness of agile methodologies. The episode culminates in a discussion about the critical importance of intentionality in hiring, integration, and communication, emphasizing that remote workers must feel connected to the company's culture to thrive and contribute effectively. This episode serves as a valuable resource for entrepreneurs grappling with the complexities of building and sustaining their teams in an increasingly competitive landscape.

    Takeaways

    • The podcast reveals that a staggering 73% of offshore or nearshore projects ultimately fail, underscoring the critical importance of effective management and strategy in such ventures.
    • Luis Derechin emphasizes that extending a startup's runway may be more about rethinking hiring strategies, particularly by sourcing talent from Latin America at more sustainable costs.
    • Effective communication and cultural understanding are essential for the success of remote teams, especially when integrating talent from diverse geographical locations.
    • The discussion elaborates on the significance of real-time collaboration, highlighting how working within similar time zones can enhance team dynamics and productivity.
    • The concept of 'grit' is explored, suggesting that resilience and a deep-seated determination to succeed are key traits among successful entrepreneurs in the startup ecosystem.
    • Luis shares insights on a framework for remote team success, which includes rigorous talent selection and optimized team performance as pivotal components.

    • LinkedIn
    • Nir-Yu | Your nearshore staffing...
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    49 mins
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