On today’s show, we are happy to welcome someone we’ve wanted to have on for some time now, Andrew Wilkinson. He is currently a Managing Partner at Tiny Capital, as well as the Founder of MetaLab, which helped design Slack. Along with this, Andrew is also invested in a range of other companies. In this episode, we learn more about his incredible journey and how he grew a passion for tech and design into a range of flourishing businesses. Andrew also sheds light on his investing education and overcoming his initial reluctance to see the power of investments. For Andrew, being an entrepreneur is about freedom to create the life you want, and having time to pursue your interests, which is how he saw the value of delegating. This is not easy when you are starting out your entrepreneurial journey, as Andrew knows, but as a company scales, so too should the owner’s levels of delegation. We take a look at the types of businesses Tiny Capital is interested in and why they are only pursuing simple business models. Our conversation then takes a turn into a different interest of Andrew’s — subscription podcasts. We discuss why these are such effective, yet untapped income-generating models and Andrew shares some of the work they are doing in this space. We then circle back to Tiny and leadership more generally where Andrew unpacks the importance of incentives along with his characteristic lazy leadership style. Andrew’s self-reflexivity and ability to talk openly about his weaknesses is truly refreshing. This conversation was a great look into what it really means to be an entrepreneur. Be sure to tune in today!
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Eric Siu (@ericosiu) is the CEO at Single Grain, a digital marketing agency that focuses on paid advertising and content marketing. He contributes regularly to Entrepreneur Magazine, Fast Company, Forbes and more.