As a general rule of thumb, you should reach out to: • CEOs or founders for companies with 100 employees or less: At this size, companies rarely have more than three hierarchical levels. It's still possible for one central person (e.g. the CEO) to be aware of everything that goes on in the organization. • Functional leaders (e.g. Sales or Engineering leaders) for organizations with 100-250 employees: As companies grow, they start hiring more specialized functional leaders. Once that starts to happen, it's no longer realistic to expect the CEO or members of the founding team to still be keenly aware of everything the company is involved in.

The False Constraints That Limit Your Potential: - The Size of Your Opportunities I see that the most successful people swing big, even when they have no business taking those swings, and they often land The difference between you and them is your "willingness" to believe you belong in bigger conversations.

The False Constraints That Limit Your Potential: - How Quickly You Can Scale Whether it's your business or your career, there are unspoken timelines that people accept as gospel.They are all untrue: "You can only really grow at 10% a year." "You need to pay your dues for a decade before getting promoted." These artificial limits keep people moving at a crawl when they could be sprinting or pushing for more. The most successful people I know refuse to accept conventional wisdom about timelines, and oddly enough, they break them all the time.

Our limits lie in our thinking. You need to root them out and rework them. A lack of self-belief will fundamentally change how you direct your actions...across all facets of your life. The person who thinks they "might not be capable" of being the next CTO will fill themselves with anxiety and be less likely to take any chances, even if they get there. Chances that might showcase their talents and make them outstanding in their work.

Keeping the Fire, Slaying the Dragon (Part II) - People won't promote or fund me vs I AM JUST TALKING TO THE WRONG PEOPLE - I'm not built like X person vs I CAN LEVERAGE WHAT / KNOW TO MAKE THIS HAPPEN - My company isn't built for distance vs I CAN ARCHITECT THIS TO GO WHERE I WANT - These might not work vs I WILL PUT THIS INTO THE WORLD AND SEE WHAT COMES