2023 Development Plan

Learning Data Science and machine learning in Spring 2022 was fun and mind expanding. It has been valuable for its own sake. I wanted to prove that I could still learn an intimidating subject at this point in my life. And I did! The timing was fortuitous, because a few months later was the explosion of AI innovation with DALL-E and ChatGPT. It felt like I accidentally skated to where the puck was going.
Going forward, understanding technical topics at a deeper level will be fundamental to critical thinking. For example, understanding how AI works down to the mechanics of the algorithms will defend against mind fuckery as it becomes more way more common.
But, I want to stay grounded in my accumulated experience and strengths as a business operator. Becoming more technical will bolster my skillset in brand new directions. For example, I was always very numerate (pretty handy with spreadsheets), but still had to recruit an analyst to work with me and at a minimum, write a SQL query. Therefore, I want to become stronger in this area.

Angel investing has been incredibly important in terms of fun, learning, and growing my network. I am fully convinced that having skin in the game alongside entrepreneurs is the best and fastest way to learn about the biggest and most strategic topics. It is valuable for its own end. 2022 was my 3rd year investing. I feel good about my personalized strategy and process, and even confident enough now to be called upon as a resource and teacher to others on this topic.
On the one hand, I have also found myself useful to founders on an intangible level, aka “Being there for them.” My experience of scaling with Remitly from early days to IPO has been useful for those intangible conversations that lean more towards the psychological, emotional, and interpersonal. And even though I have a high quality reputation with regard to this, most founders I work with would struggle to articulate what I specifically and consistently help them with.
Therefore, I want to have more consistently useful skills and assets for founders to be able to call on, leading to tangible inputs. Things like: recruiting, product strategy, fundraising, customer acquisition, etc. I plan to invest time and resources to lay some of the foundations for this.
Advancing against this goal will earn positive returns to my reputation, which is by far the most important asset in this domain.