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    Think like an outsider, w/Shellye Archambeau, Ellevest’s Sallie Krawcheck, and Calendly’s Tope Awotona

    enAugust 22, 2023

    Podcast Summary

    • Embracing Outsider Status for SuccessThinking like an outsider and embracing unique approaches can lead to greater success in today's chaotic economy. Disadvantages can actually be advantages in challenging the status quo and finding unique solutions.

      Success in today's chaotic economy requires thinking like an outsider and doing things differently. Sallie Krawcheck, Shellye Archambeau, and Tope Awotona all achieved great success by overcoming obstacles and embracing their outsider status. Sallie broke the glass ceiling on Wall Street, Shellye fought her way into the CEO's seat in the tech world, and Tope built his business outside of Silicon Valley. Their stories teach us that disadvantages can actually be advantages and that taking a different approach can lead to greater success. By thinking like outsiders, we can find unique solutions, challenge the status quo, and ultimately thrive in a rapidly changing business landscape.

    • Challenging Conventional Thinking: Addressing Biases in the Financial Industry for WomenThe financial industry must recognize and overcome biases towards women, including societal expectations and false narratives, in order to effectively cater to their needs.

      The financial industry needs to challenge conventional thinking and cater to the needs of women. The story begins with the realization that a life insurance company, appearing to be growing, actually had deteriorating credit quality. This led to the understanding that subprime loans were a real concern. The conversation then shifts to the gender pay gap and the gender investing gap, highlighting the lack of representation and understanding of women in the financial industry. The surprising discovery is that even when a product is designed specifically for women, some women reject it due to societal expectations and the false narrative that women are risk averse or bad at math. The key takeaway is that the financial industry must address and overcome these biases to genuinely serve women's needs.

    • Turning Disadvantages into Opportunities in EntrepreneurshipAssess your advantages and disadvantages, and use your limitations as opportunities to achieve success in entrepreneurship.

      Being an outsider can actually be advantageous in entrepreneurship. Tope Awotona, the founder of Calendly, shares his experience of being an outsider due to his background, location, and lack of a successful entrepreneurial track record. Instead of letting these disadvantages hold him back, Awotona turned them into opportunities. He took unconventional approaches by emptying his 401(k), taking out loans, and adopting a freemium business model with a focus on customer satisfaction. By maniacally prioritizing and spending more time with customers, Awotona was able to build a successful and profitable company without relying on outside capital. This story teaches us to assess our advantages and disadvantages and find ways to turn limitations into opportunities for success.

    • Choosing the right investors and thinking like an outsider for business growth and success.Select investors with a track record of accelerating growth and achieving better outcomes, while also embracing unconventional approaches to succeed in challenging situations.

      Choosing the right investors can significantly impact the growth and success of a business. Institutional capital provides validation and can attract more enterprise customers, making it crucial for ambitious goals. When selecting investors, it is important to consider their track record in accelerating growth and achieving better outcomes for businesses like yours. Additionally, having a network of supportive allies is essential in building a great business. Thinking like an outsider can also unlock opportunities and challenge the status quo. By embracing her outsider roots and learning to pay close attention to her surroundings, Shellye Archambeau orchestrated a dynamic turnaround as CEO. Therefore, it is crucial to find unconventional approaches and leverage them to achieve success in the face of adversity.

    • The Importance of Pivoting and Being Open to Change in BusinessBusinesses should not be afraid to pivot and adapt when faced with failure or a lack of interest. Being open to external feedback and willing to make necessary changes can lead to new opportunities and success.

      It is crucial for businesses to be open to pivoting when faced with failure or a lack of interest in their current product or service. In the case of Zaplet, they were burning through money and struggling to sell their product. By looking outside for insight and speaking to industry experts like Roger McNamee, they discovered a pressing problem in corporate America: compliance. They then conducted their own research to confirm the need for a solution in this area. With limited resources, they partnered with MetricStream, rebranded, and focused on solving the compliance problem. One important lesson learned throughout this journey is to not become too attached or in love with one's product, as it may prevent necessary changes and hinder success. Being receptive to external feedback and willing to adapt is key in navigating challenges and finding new opportunities.

    • Understanding your market and adapting your offerings for success.Falling in love with your target market, adapting your offerings, and fostering an outsider mindset can lead to innovation and success.

      Falling in love with the market you're targeting is crucial. By understanding your customers' needs and requirements, you can tailor your product or service to meet those needs effectively. This requires a deep level of care and attention, like nurturing a baby. It is important to recognize that the initial idea or product may not be the ultimate solution you're aiming for. You must be willing to adapt and morph your offerings to align with what your target market truly needs. Additionally, fostering an outsider mindset within your team can lead to innovative thinking. By asking thought-provoking questions and encouraging resourcefulness, you can inspire your team members to think outside the box and continuously learn and evolve. Ultimately, through intentional values and diverse hiring, you can create a team that brings fresh perspectives and drives success.

    • Embracing diversity and challenging norms for innovation and growth.Incorporate diverse perspectives, challenge established norms, and trust your own knowledge and beliefs for successful product development and meaningful change.

      In order to create successful products and drive meaningful change, it is important to incorporate diverse perspectives and experiences. By bringing in people with different backgrounds and expertise, such as someone from outside the industry, a company can gain fresh insights and approaches to problem-solving. Additionally, it is crucial for leaders to actively reinforce the desired behaviors and incorporate them into the company's processes, making them second nature instead of temporary exercises. Being an outsider and challenging established norms can be difficult, but it is necessary for innovation and growth. Ultimately, leaders should trust their own knowledge and beliefs, staying confident in their ability to navigate the path towards success by thinking differently.

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