Questions I ask to suss out red flags after a dozen+ experiences: - Who are the founders? - Who is the CEO? - Who runs the company? - Do the founders h

Questions I ask to suss out red flags after a dozen+ experiences: - Who are the founders? - Who is the CEO? - Who runs the company? - Do the founders have any experience running a startup? - Who are the key investors? - Do the investors have any experience mentoring founders running a startup? - How much money did the company raise? Is that a reasonable runway? - Did they actually form a company? - Did they actually file the paperwork with the SEC (if US) documenting the fundraising? - What employment terms are they offering? - Are they especially onerous on the employee? - Are they offering a ridiculous or a reasonable amount of equity in return for a reduced salary? - Who is their payroll provider? - Who is their bank? - How are they tracking expenses and accounting in general? - How are they measuring success (for whatever stage the company is in)? It's ok to have “wrong” or even no answers to some of these, especially if the company isn’t even really in operation yet. But no answers or wrong answers to many of these lead me to walk away. You are not going to get a lot of detail about capital structure or investment terms unless you’re coming in as the CEO or a C level executive. But I have found that checking and verifying to learn that the company and executives are practicing just the basic mechanical business skills of setting up the business is a good “smell” test for how they are operating the company. You may personally decide that you’re ok with paychecks being written against a personal bank account, or that an LLC vs C Corp (again, US specific, apologies) is reasonable at this stage of the company. There's no single thing I look for, it’s a balance of questions and how the company / founders /CEO responds. Just this week a colleague was negotiating final terms to join a startup. They asked to clarify a specific employment term that was verbally made as part of the offer, but not included in the employment contract they were asked to sign. The CEO reacted extremely inappropriately and, well, my colleague isn't joining the startup. My first few startups I was far too naive in assuming that if investors had invested what was claimed then they must have done some due diligence. Learning after the fact at one company that the Series A was actually not closed and the founders were financing the company off credit cards and home equity lines of credit lead me to leave after only six months.