Masters of Scale

Stewart Butterfield, Co-founder and CEO of Slack, is known for transforming failed gaming ventures into groundbreaking platforms like Flickr and Slack. He shares insights on the critical moments that prompted major pivots in his career. Listeners learn how Flickr was born from a stalled game project and how Slack evolved from a communication tool into a business necessity. He emphasizes the importance of community involvement and employee support during challenging transitions, showcasing how storytelling and adaptability lead to innovation.

Whitney Wolfe Herd, founder of Bumble, shares her journey of transforming online dating with innovative ideas to empower women. She discusses how small changes can lead to significant impacts, using anecdotes from her own experience. The conversation touches on redefining dating norms, the importance of user insights, and creating safer environments in digital interactions. Wolfe highlights Bumble's unique approach where women make the first move and examines the app's growing influence, especially in India, where it sparks cultural shifts.

Gwyneth Paltrow, an acclaimed actress and founder of the lifestyle brand Goop, discusses her transition from Hollywood to entrepreneurship. She shares her insights on the value of life experience in business and how it can fuel innovative ideas. Paltrow emphasizes the importance of mentorship and networking in building a brand. She reflects on the challenges of leadership and the need for a strong company culture while scaling a startup. With fascinating anecdotes and advice, she inspires listeners to embrace entrepreneurship, regardless of their age.

Navigating a big career change can be daunting, but insightful advice from industry leaders makes it easier. Key discussions revolve around balancing passion with practicality, the power of honest feedback, and the importance of strategic planning. Personal stories of resilience highlight how challenges can foster growth. The significance of adaptability is emphasized, along with innovative employee benefits, while the necessity of maintaining work-life balance in high-pressure environments is explored. Overall, it's a valuable guide for anyone contemplating a career pivot.

Dara Khosrowshahi, CEO of Uber, discusses his journey transforming the company's culture from a chaotic 'pirate ship' to a disciplined 'navy.' He shares insights on the importance of truth-telling and ethical behavior in leadership. Dara highlights the challenges he faced in promoting accountability and removing toxic practices within Uber. He also emphasizes the need for authenticity in communication and how fostering an inclusive environment directly enhances employee morale and customer experience.

Ben Chestnut, CEO of Mailchimp, shares his journey of bootstrapping the company to $600 million without external funding. He emphasizes the DIY ethos that fueled Mailchimp's growth and explains how storytelling and community support are vital for entrepreneurs. The conversation delves into the unique challenges of bootstrapping in the tech landscape, contrasting it with VC funding. Chestnut also discusses the significance of aligning investors with a founder’s vision and innovative strategies that foster growth, such as engaging customer feedback and enhancing employee appreciation.

In this engaging conversation, Joi Ito, the visionary Director of the MIT Media Lab, discusses the critical balance between open and closed organizational systems. He argues that chaos can fuel innovation, drawing on his experiences with Creative Commons and cyber currency. Joi shares insights on navigating traditional corporate structures while embracing openness, illustrated by real-world examples like crowdsourced translation programs. Megan Smith makes a cameo, further emphasizing the transformational potential of collaboration in today's interconnected landscape.

Shellye Archambeau, the former CEO of MetricStream and a tech turnaround expert, discusses the importance of taking risks for success. She vividly shares her journey from leading a struggling company to achieving significant growth through calculated decisions. Archambeau emphasizes that avoiding risk can lead to mediocrity. She explores strategic planning, leadership under pressure, and the influence of heritage on personal identity, offering valuable insights on resilience and innovation in the business world.

Sallie Krawcheck, a former Wall Street executive and founder of Ellevest, discusses the necessity of diversity in the workplace. She shares her journey from investment banking to creating a platform for women's financial empowerment. Sallie highlights the gender investing gap and the biases women face in finance, calling for cognitive diversity to solve these challenges. With humor and insight, she makes a compelling case for how inclusive perspectives fuel innovation and enhance economic growth.

We’re back with Part 2 of our special turn-the-tables episode with Reid Hoffman. In this episode, we follow Reid through PayPal, LinkedIn, the Microsoft acquisition, his angel investments, Greylock, and his hosting of Masters of Scale — all the while proving our theory that you can chart an epic journey to scale if you make everyone you enlist a hero — in their OWN story and not just yours. Guest host: June Cohen, the executive producer of Masters of Scale and the cofounder of WaitWhat, the company behind it). Cameo appearances: Arianna Huffington (Thrive Global) and Jeff Weiner (LinkedIn).Read a transcript of this interview at: https://mastersofscale.com/reid-hoffman-make-everyone-a-hero-part-two/Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.