A Purposeful Career

I’m starting to find more purpose in my career, and invest more time, energy and capital into activities that further this purpose (my 2021 goals here). There was a period in my life where I thought I only wanted to work on problems in emerging markets (particularly Africa) and although I still care deeply about this area, I realize that’s more narrow than where I actually enjoy spending my time and resources.

I’d like to build a career in service of entrepreneurs and creators.

  • Making software allows me to build tools that support entrepreneurs and creators at at the earliest stages and at scale.
  • Angel investing allows me to compound capital, relationships, and learning and ultimately make better software.
  • Investing and operating allows me to build both broad and deep relationships with people over a very long time horizon.
  • Investing and operating let’s me learn and writing helps me share my learnings with others which in turn refines these learnings.

Making Software

I’ve been working in software development for over 15 years. I’ve helped build products for consumers, enterprises, and small businesses. I’ve found the most fulfillment in building utility software to help entrepreneurs run their companies and help people collaborate.

I’m particularly drawn to building software that is ‘Free to Start’ as this allows users to get value even at the smallest scale. World class software can be used by people starting new projects without paywalls that prevents folks who are not well capitalized from participating.

I’m also interested in Open Source projects (e.g. WordPress) as they have all the benefits of ‘Free to Start’ but also allow users to contribute to the development and customize it for their own (possibly esoteric) requirements which is often necessary in emerging markets or emerging use cases.

Finally, I’m really excited about software that helps us collaborate better as humans especially as the way we collaborate evolves into cloud based and distributed work. I’m looking forward to spending my own time innovating in this area. I wrote more about this area in another post “A More Open World“.

My hope is these products can be helpful to entrepreneurs and creators.

Angel Investing

I’ve been angel investing for over a decade – I enjoy it and have learned a lot. Angel investing allows me to develop and cultivate new relationships with people I would not ordinarily meet, stay close to cutting edge innovation and compound capital over a very long time in a way that is very aligned with entrepreneurs.

I enjoy meeting entrepreneurs who are passionate about the problems they are solving and have a really strong ‘Why’ story. As a very small investor my role is a friend to the founder and cheerleader for the business and don’t have the same baggage that institutional investors need to consider (round dynamics, ownership targets etc).

I’ve found it helpful as an operator at scale to stay close to innovation in adjacent industries and adjacent business models. It helps me generate new ideas, recognize patterns across companies and ultimately makes me a better operator.

My hope is that these small investments can be helpful to entrepreneurs.

Building Relationships

Investing and operating has allowed me to build both broad and deep relationships with entrepreneurs and co-investors and colleagues.

I’ve found that more repetitions (over a concrete thing) with the same people or group builds lasting trust and rapport especially when I don’t have a formal relationship such working at the same company. If you are actively collaborating on a project together or evaluating an investment together over many cycles you can build deep, trusting relationships.

I’ve been spending time collaborating with a very small group of co-investors – many who I’ve known for 20+ years. In this strange time of physical distance I’ve tried to be more structured and disciplined in my approach to collaboration (more writing, more sharing) and it’s helped me build stronger relationships as an operator and investor.

I’ve found that broad relationships are very helpful for making connections / introductions which are important. The smaller set of deeper relationships are very helpful for refining synthesis and judgment (as these folks are much more direct and honest).

My hope is that these relationships can be helpful to entrepreneurs either directly or indirectly.

Learning and Sharing

I’ve been trying to compound my learning as much as possible – through operating, investing, and consuming content (mainly audio books and podcasts). The intersection of all of these activities helps me develop a perspective on the world that is unique to my set of experiences, which has the potential to have a lot of depth.

I’ve been trying to write and share more of this with others (in this public blog – now over 80 posts!) and some of the idas are ‘stubs’ and others are areas where I feel more confident in the subject matter.

Writing helps me synthesize and crystalize my point of view and also allows my thinking to be shareable at scale. I’d like to experiment with a newsletter next, even to a small private group as I think this could help me synthesize across a series of topics in a way that could be useful to a particular audience.

My hope is that this shared learning can be useful to entrepreneurs.


All this thinking may evolve, but it’s been consistently true over many years so I wanted to document it openly. I hope I can come back to this post in ten or twenty years and feel like I’ve had a career in service of entrepreneurs and creators.