I too often see marketing plans “focused” on everything: podcasts, site redesign, name change, conferences, awards, etc. When you focus on everything, you are clueless; you will fail at everything and spend all your money. FOCUS. Get one thing working, then move on to the next high-conviction item.

Below is a very brief overview of the three pillars of marketing.

I’m often asked for career advice. People think linearly: I get my degree, work for two years, return and get my MBA, etc. I like to challenge people to think non-linearly if they want to be massively successful. Here are the four career tips I give people:

Guava, one of our investments, is a free app aggregating ALL your healthcare data in one place. They pull data from your consumer, commercial devices, and over 50,000 healthcare providers (physicians, hospitals, blood labs, etc.). You can have a comprehensive view of all of your health data. They added a cool feature called "Insights" that looks for correlations between factors, like how the number of steps impacts sleep.

Jason and I go back to the early days of the Internet. Back in 1996, Jason started “The Silicon Alley Reporter” while we were building DoubleClick. We finally got to catch up on Jason’s “This Week in Startups” podcast. Enjoy.

This was a good exercise in collaboration with an LLM to distill my current understanding of various business models for startups, based of what I have seen over the past several years.

Measuring CAC Payback by channel is a must-have strategy if you are looking to scale. This will help you design a predictable, forecastable, and scalable go-to-market motion.

As someone who has had the opportunity to manage teams of 100 or more individuals, as well as being managed, I have gained some experience and knowledge that I hope can be useful to others. Through trial and error, and a willingness to learn from my mistakes, I have developed a few mental models that have helped me to navigate the challenges of leadership. In this post, I would like to share ten insights with you in the hopes that they may prove helpful in your own professional journey.

As a startup founder, it's important to keep an eye on paradigm shifts in technology because they present opportunities for disruption and the emergence of new winners. In the past, we've seen software displace machines, the internet create software as a service, and mobile-first products overtake the consumer market. Now, we're in the midst of another paradigm shift, and that's the rise of AI.

Kevin O’Connor’s guidance on how to be a CEO