Connecting Dots and People: Ash Phillips

In this eye-opening episode of Generally Curious, hosts Milly and Lindsey delve into the multifaceted world of entrepreneurship with Ash Phillips, the Founder and Chair of Rebellious Co.

With a career spanning over a decade, Ash shares the patterns of success and common pitfalls he's encountered in his journey. From building and scaling companies to navigating the uncertainties of entrepreneurship, Ash provides deep insights into the risk management frameworks that have guided his path. As an angel investor, he also sheds light on what investing has taught him about business and life.

Furthermore, Ash, a renowned speaker, shares invaluable advice for aspiring speakers on becoming more confident on stage and landing both their first and bigger gigs. This episode is a must-listen for anyone interested in entrepreneurship, leadership, and the unique blend of skills that drive innovation and success in the business world. Join us as we explore Ash's dynamic career, his contributions to the UK startup ecosystem, and the invaluable lessons he's learned along the way.

Fun Fact: Ash introduced Lindsey + Milly, so this podcast quite literally would not have existed without Ash 👏

The introduction (00:00:01) Milly and Lindsey introduce the podcast and its purpose.

Introducing Ash Phillips (00:00:59) Ash Phillips' background and accomplishments are introduced, focusing on his impact in entrepreneurship and leadership.

Insights into entrepreneurship (00:02:12) Ash Phillips' insights into entrepreneurship, leadership, and innovation are discussed, along with patterns of success and common mistakes.

Patterns of success (00:03:41) Ash Phillips discusses the patterns of successful people and the role of confidence.

Common mistakes in business (00:07:07) The discussion shifts to the common mistake of focusing too much on small details and neglecting the importance of selling in business.

Career and self-reflection (00:09:45) Ash Phillips reflects on his career path, self-awareness, and the importance of taking life one step at a time.

Internal work and risk in entrepreneurship (00:13:23) The conversation delves into the internal work required for entrepreneurship and the tolerance for risk and uncertainty in building companies.

Objective vs. Holistic Approach (00:18:31) Ash discusses intuition and gut feel in decision-making, emphasizing the importance of subjective and objective approaches.

Evaluating Risk and Fiscal Management (00:21:14) Ash explains the importance of evaluating risk and fiscal management, providing insights into using mathematical analysis for risk assessment in business.

Angel Investing and Founder Market Fit (00:22:41) Ash shares his experiences and insights into angel investing, emphasizing the significance of founder market fit and subjective evaluation in early-stage investments.

Getting Started in Angel Investing (00:26:51) Ash provides tips for individuals interested in angel investing.

Becoming a Confident Speaker (00:29:31) Ash offers advice on becoming a more confident speaker, emphasizing the importance of having a common theme and understanding that most people in the audience may not care.

Energy and Engagement in Speaking (00:33:57) Milly discusses the importance of bringing energy and humor to speaking engagements.

The unique perspective (00:35:37) Discussion on the power of combining unique perspectives in entrepreneurship and the value it brings to the industry.

Bento box time management (00:39:24) Explanation of a time management strategy using a visual representation of time allocation, known as a bento box.

Spinning plates (00:41:37) Ash Phillips provides an overview of the different projects he is working on and how they intersect or operate independently.

Lightning round questions (00:44:17) Quick-fire questions about defining a generalist, the impact of social media on career journey, and the potential of generalists in the world.

Conclusion (00:47:13) Closing remarks and gratitude.