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...

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...

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...

Lubna Hameed

Bio

Lubna Hameed is a fractional design leader who helps early-stage startups go from blank brief to product market fit without accumulating creative debt. As the co-founder of The Company Advice, she leads design across product and web in partnership with marketing from day one—keeping the message and the experience in sync.

Her work spans user flows, information architecture, UX writing, and polished UI—all grounded in fast learning, intentional structure, and measurable impact. Previously Director of Design at Particle Health, Lubna built the design function from zero to one and shipped web and mobile experiences across complex healthcare workflows.

She’s known for her “designer who loves data” mindset, her no fluff approach to discovery, and her belief that design isn't just how it looks—it’s how it works, converts, and earns trust.

Summary

The central theme of this podcast episode revolves around the critical understanding that early-stage startup founders often fall prey to the debilitating misconception that their product must attain a state of perfection prior to its launch. Lubna Hameed, an esteemed expert in guiding startups from inception to product-market fit, articulates the imperative that readiness should not be equated with flawlessness, but rather with the clarity of objectives and the willingness to learn from iterative processes. Drawing from her extensive experience as the founder of Advice, she emphasizes the detrimental effects of delaying launches in pursuit of an ideal product, which frequently results in missed opportunities and wasted resources. We delve into the necessity of integrating design and marketing from the outset, highlighting that these functions must collaborate closely to ensure a cohesive user experience. This episode is essential for founders who are contemplating their next steps in navigating the tumultuous waters of startup development, particularly those grappling with the question of when their product is truly ready for the market.

Notes

The dialogue between Jothy Rosenberg and Lubna Hameed delves into the challenges that early-stage startup founders encounter, particularly the common pitfall of striving for perfection before launching a product. Hameed emphasizes that many founders erroneously believe that they must await a flawless product before entering the market, which can ultimately derail their startup aspirations and hinder potential growth. Instead, she advocates for a mindset centered on iterative learning: the notion that each launch, irrespective of its perceived completeness, serves as a crucial opportunity for gathering invaluable user feedback and insights. The conversation elucidates the significance of clarity regarding the target audience, the problems being addressed, and the metrics of success. Hameed's insights are rooted in her extensive experience in working alongside various startups, where she has observed firsthand the transformative power of launching minimally viable products and utilizing the ensuing data to inform future iterations. This episode serves as a clarion call for founders to embrace the learning process inherent within the launch experience, rather than being paralyzed by the fear of imperfection.

Takeaways

• The fundamental principle for startup founders is that they must prioritize learning over achieving a state of completion when launching their products.
• Perfectionism acts as a significant barrier to progress; one should focus on iterative development rather than waiting for an ideal product.
• Integrating marketing and design from the outset is crucial; these functions must collaborate closely to ensure a cohesive user...

Richard Sides

Bio

Richard Sides is Founder and CEO of Adroit North America and Adroit Hardware Solutions. Adroit North America was recently named to the Inc5000 at #1026 representing annual growth in excess of 40%. Rich is a driven entrepreneur that has founded and exited multiple ventures, some more successful than others including lawn care, systems consulting, an E-Commerce based chocolate truffles business, foreign language translations, supply chain software, ERP systems reseller, and plant floor computing hardware and integration. He has a passion for the food and beverage industry having started his career at Kraft Foods in 1990 and serving as SVP Of Information Systems at Preferred Meal Systems. He formed a jazz band called Blue Orbit Combo in 2019 that plays regularly through the Chicago area and speaks decent Spanish which he started to learn about 15 years ago.

Intro

Richard Sides’ transformative journey from a timid engineer to a successful entrepreneur underscores a pivotal revelation about career security: corporate loyalty is an illusion. This profound realization was catalyzed by witnessing his father’s abrupt termination after three decades at U.S. Steel, an experience that imbued him with a steadfast resolve to forge his own path. Throughout our conversation, Richard recounts his evolution, detailing how he overcame his introversion by immersing himself in consulting, ultimately leading to the establishment of multiple thriving enterprises within the food industry. He elucidates the critical importance of cultivating resilience and adaptability in the face of challenges, as well as the necessity of creating one’s own security through skills and relationships. Join us as we delve into Richard’s insights, which illuminate the intricate interplay between personal growth and entrepreneurial success.

Conversation

Richard Sides' journey from a seemingly secure corporate environment to the precarious realm of entrepreneurship unfolds like a compelling narrative, punctuated by significant life events that shaped his perspective on career security. At the tender age of seventeen, Richard witnessed the abrupt termination of his father's three-decade career at US Steel, an event that indelibly altered his understanding of corporate loyalty and job security. This pivotal moment instilled in him a profound conviction to never relinquish control over his professional destiny. As the discussion progresses, we delve into Richard's evolution from a shy, introverted engineer who struggled with interpersonal interactions to a formidable entrepreneur who has successfully launched multiple ventures in the food industry. His decision to pursue consulting as a means of personal growth is a testament to his resolve to confront and overcome his inherent challenges. Through his experiences, Richard elucidates the importance of cultivating skills, fostering relationships, and embracing calculated risks to build one's own security and autonomy in an ever-changing job market.

Takeaways

• The notion of corporate loyalty is fundamentally flawed; individuals must cultivate their own security and resilience.
• Richard's early experience with his father's sudden job loss profoundly influenced his entrepreneurial journey and career decisions.
• To achieve personal growth, one must confront discomfort; Richard's choice to pursue consulting forced him to overcome his introverted tendencies.
• Success in entrepreneurship relies on mastering delayed gratification; setting long-term goals allows for sustained effort and achievement.
• Building optionality through skills and relationships is critical; do not wait for unforeseen...

Shan Nair

Bio

Dr. Shan Nair is an entrepreneur and consultant on international expansion. He was the first to spot and develop the niche market of International Expansion Services (IES) which was previously fragmented. In the process he has worked with many companies in their early stages who have since become household names such as Tesla Motors, FaceTime and Sonus Networks. His role is to promote the services offered by Nucleus and to work with the management team to ensure a high level of technical excellence and client care is maintained at all times.

Nucleus is unique in that it provides true one stop, multi-disciplinary, multi-country shopping for companies seeking international expansion or with international operations. A single experienced Client Services Director and an Accounting Manager will be your sole points of contact for all of your foreign consulting needs – you will not need to chase multiple accountants, lawyers and HR consultants in different geographies or have a single contact point with little expertise acting simply as a postbox. The Client Services team is backed by staff at senior and mid-management level each having more than a decade of experience in providing IES services.

Shan has a doctorate in nuclear physics from the University of Oxford. He has received multiple recognitions for his contribution to business in the US, UK and India.

Intro

The conversation with Shan Nair elucidates the two predominant errors that enterprises frequently commit when endeavoring to expand internationally. Foremost among these missteps is the absence of a well-defined strategy, which often leads to a host of operational challenges and unanticipated legal ramifications. Additionally, Nair emphasizes the peril of attempting to navigate foreign markets with a constrained budget, a decision that can culminate in exorbitant costs in the long run. Drawing upon his extensive experience as an international expansion expert, he shares cautionary tales that illustrate the potential consequences of neglecting local legal frameworks. This dialogue serves as a critical resource for any organization contemplating global growth, underscoring the necessity of thorough planning and informed decision-making in the pursuit of international success.

Conversation

In this enlightening discourse, Jothy Rosenberg engages in a profound dialogue with Shan Nair, a distinguished expert in international expansion. The core of their conversation revolves around the intricate challenges faced by companies as they venture into global markets. Nair elucidates two pivotal missteps that frequently plague startups embarking on international journeys: the absence of a coherent plan and the inclination to economize on essential legal and operational frameworks. He stresses that a lack of foresight in understanding the regulatory landscape of foreign nations can lead to catastrophic financial repercussions, thus underscoring the necessity for thorough preparatory measures. Nair's extensive experience, spanning fifteen countries, provides him with a unique vantage point, enabling him to share harrowing examples of companies that have suffered dire consequences due to neglecting these fundamental aspects. Through this episode, listeners gain not only insights into the operational complexities of international business but also practical advice on how to navigate these treacherous waters effectively, ensuring their ventures are both profitable and sustainable.

Takeaways

• The foremost error companies commit when expanding internationally is a lack of a coherent and well-defined plan.
• Companies often underestimate the costs associated with international expansion,...

Jean Serra

Bio

Jean Serra is Founder and CEO of V2 Communications, an award-winning Boston-based communications strategy firm specializing in AI, B2B, healthcare and climate technologies. Since launching V2 in 2006, her firm has created high-impact programs for organizations including UiPath, Cloudera, AlphaSense, Breakthrough Energy Ventures and Instride Health. A pioneer in communications, PR/AR, social media, content marketing, and brand visibility in the AI era, Jean is known for developing programs that shift market perception, fuel growth and deliver measurable business impact. Learn more at www.v2comms.com.

Intro

The primary focus of today's discussion revolves around the transformative nature of communications in the tech industry, as articulated by our distinguished guest, Jean Serra, the founder of V2 Communications. With a wealth of experience, Jean elucidates how traditional perceptions of public relations are fundamentally misguided, positing that effective communications are pivotal for establishing credibility in an increasingly competitive market. She emphasizes that many founders fail to grasp that securing press coverage is merely a facet of a broader narrative-building strategy essential for their survival and growth. Jean's insights are particularly salient in today's landscape, where the advent of AI answer engines is redefining how brands are perceived and interacted with in digital spaces. As we delve into this conversation, we aim to illuminate the critical importance of strategic communication for startups, ultimately challenging preconceived notions about its role and efficacy.

Conversation

The dialogue between Jothy Rosenberg and Jean Serra unveils the transformative landscape of public relations (PR) in the technology sector. Jean, the founder of V2 Communications, elucidates how her agency has redefined the conventional paradigms of tech PR by prioritizing genuine communication that fosters credibility rather than merely securing press coverage. She recounts her journey from being an English major with no clear career path to establishing a successful agency that has navigated challenging economic climates, particularly during the 2008 financial crisis. Through this narrative, listeners are introduced to the notion that effective communication is essential for startups not just for visibility, but as a fundamental component of their survival and growth in a competitive market. Jean emphasizes that many founders misconstrue PR as a luxury rather than a necessity, thereby highlighting the critical need for startups to recalibrate their understanding of communication as an integral part of their operational strategy, essential for attracting investment and building a brand narrative that resonates in an ever-evolving digital landscape.

Takeaways

1. The fundamental tenet in communications for startups is to regard it as infrastructure rather than mere marketing, which is critical to establish credibility and market presence.
2. Jean Serra's agency, V2 Communications, emphasizes a service-oriented approach, aiming to be indispensable partners to their clients amidst the competition in the tech industry.
3. In the rapidly evolving landscape of AI, startups must now consider their visibility in AI answer engines, as traditional Google searches become increasingly less relevant.
4. The foundation of success in public relations lies in building...

Kae Kronthaler-Williams

Bio

Kae Williams is a global software marketing executive on a mission to empower women in their careers through her work and her forthcoming book, Not Made For You. She raises awareness about bias and hostile work cultures so every woman feels supported, respected, and enabled to achieve her full potential. She champions this cause through writing, speaking, coaching, and nonprofit work because when barriers are removed for women, everyone benefits.

Intro

The conversation with Kae Kronthaler-Williams delves into the nuanced challenges faced by women in the realm of startup leadership, particularly as she articulates her experiences navigating a landscape often fraught with unspoken barriers. Kae draws upon her extensive career to illuminate the systemic issues that hinder women's full participation and recognition within corporate environments. She emphasizes the necessity for women to develop pragmatic strategies to confront these insidious barriers while maintaining their career trajectories. Furthermore, Kae's insights extend to her forthcoming book, "Not Made For You," which aims to provide a voice to these challenges and offer actionable guidance for women striving for success in their professional endeavors. This discourse not only underscores the importance of gender representation in leadership roles but also serves as a clarion call for organizational awareness and cultural transformation.

Notes

The discussion between Jothy Rosenberg and Kae Kronthaler-Williams presents a profound exploration of the challenges encountered by women in the startup ecosystem. Kae, with over three decades of experience in startup leadership as a woman of color, articulately shares her insights on the barriers that often remain unspoken yet significantly hinder women's career progress. Through her personal experiences and her new book, 'Not Made For You', she sheds light on the pervasive issues of sexism, ageism, racism, and microaggressions that women face in the workplace. Kae emphasizes the necessity for women to navigate these challenges with resilience and strategic acumen, providing practical approaches to overcoming obstacles and achieving success. This episode serves not merely as a narrative of struggles but as an empowering guide for women aspiring to thrive in their careers, offering them tools to confront biases and advocate for themselves effectively.

Takeaways

• Kae Kronthaler-Williams emphasizes the unspoken barriers women face in their careers and how they can navigate these challenges effectively.
• The discussion highlights the importance of equal gender representation in leadership roles, which significantly impacts workplace dynamics and decisions.
• Kae shares her experience of advocating not only for herself but also for her team, showcasing the need for visibility and recognition in male-dominated environments.
• The podcast underscores the necessity of building one-on-one relationships to overcome biases and foster authentic connections in professional settings.
• Kae's insights reveal that women's experiences in the workplace can differ drastically from men's, necessitating unique strategies for success.
• The significance of addressing issues like sexism, harassment, and microaggressions is paramount, as these factors contribute to the challenges women encounter in their careers.

• Kae's web site
• Substack
• Kae Kronthaler-Williams - United States | Professional Profile |...