Tough Questions to Ask Co-founders

Philip Camilleri
8 min readMay 20, 2020

As a startup founder, one of the most important decisions you’ll ever make is your choice of a co-founder. Finding the right one is crucial. You’ll work through drudgery together and you’ll move as a singular unit when your startup is having funding or traction problems. Your habits, mindset, and instincts will inevitably clash, especially during difficult times.

Therefore the first thing you must do is to take your potential co-founders through a careful vetting process. Don’t simply take skills, experience, and compatibility at face value. You need to dig deeper and ask tough questions.

The First Question

Before you engage a potential co-founder in a lengthy discussion, make sure you’ve asked this first: Is getting a co-founder really the right move for you? Consider the following pros and cons of having a co-founder:


  • Faster scale. Compared to a founding team with two members, solo founders take 3.6 times longer to reach scale, according to the Startup Genome Report. The report defined scale as the stage where the startup gets Series A funding, has massive customer acquisition, and has more established operations in the form of executive hires and the creation of departments. Once at this stage, your startup will have established a solid foundation, since it has already solved basic issues such as product-market fit, product-solution fit, and fundraising. While you shouldn’t rush to scale, the faster your startup achieves it the less time your startup spends in uncertainty.
  • Co-founders can bring in complementary skills. Co-founders can also bring in domain expertise you don’t have. A technical founder can bring in a co-founder with marketing or business development experience, and vice versa. The benefits of having complementary experience will play out in many areas of your startup. Balanced teams with technical and business co-founders tend to raise 30% more money and have more user growth than teams that are heavily focused on either business or tech. They are also more likely to scale at an appropriate rate.
  • Co-founders can broaden your network. You only get this benefit if you choose a co-founder who doesn’t have many overlapping networks with you. Did they attend a different…
Philip Camilleri

Former corporate tech, turned co-founder & CTO @ SmartAsset. Now building, a platform for founders to connect & find the resources they need.