5 Questions I Asked Before I Launched My Startup

Ben Grapevine
3 min readSep 2, 2022

Who among us doesn’t have a dream to be the next king of Silicon Valley, sitting pretty on a throne of self-made success? We all have an idea that we think could be the next big startup; where we differ is preparation, dedication, and asturdation. Last week, the startup I launched at the height of the pandemic finally hit its first million in profit revenue. I might not be king yet, but I’m on my way, and I’m willing to share the throne with you. Here are the five questions I asked myself before I began my journey to prosperity:

  1. Where is the capital coming from? — A startup without finances is a hobby. If six years in the tech industry has taught me anything, it’s this: no matter your background, no matter how foolproof your plan, if you don’t have the know-how to secure reliable funding, you’re going to fail.
  2. Am I passionate about this? — A startup is more than a company. It’s the soul of its founding members. It’s less “should I get bangs?” and more elective amputation: if you’re not serious about it, it’s going to be rough.
  3. Am I ready for the hours? — Whatever you think it’s going to take, it’s going to be more. You’re going to wake up tired, you’re going to miss social events, your penis is going to shrink slightly. This is all normal. If the titans of business who came before made it through, you can too.
  4. Am I gay? — I was living as a straight man when I launched my startup. I thought I had everything together, I thought I was ready for the commitment and the long hours, but I realized that the paradigm shift that is coming out as gay could jeopardize my plans. I’d have to tell my friends and family, mentally prepare for their reactions, and stop dating women. I wasn’t worried about success; the world of business is replete with successful gay entrepreneurs like Tim Cook, Jim Fitterling, and Rosie O’Donnell. I could do it, but I’d have to be ready. I’d have to once and for all answer the question: “am I gay?”. And for me the answer was “no”.
  5. Where do I start? — Let’s be honest: when we dream about launching our startups, we’re thinking more about the “up” part than the “start”. A successful team isn’t born overnight, and a great idea is nothing without the right people to execute it. I’ll tell you what worked for me: most companies start with the big-ticket positions, the CFOs and CTOs of the world. You don’t want to be “most companies”. And neither do I. I hired an expert pickpocket renowned all over YouTube for his top-tier crime tutorials. For the first month of my operation, Kyle was more important than my C-suite. He was step one. Step two? Hiring and scheduling in-person interviews with prospective employees from outside the country. Once they enter the door, I have Kyle steal their passports. I already know the question you’re asking: what if they don’t have their passports on them? I’m way ahead of you. You and I both know that versatility is an important trait in a loyal employee. Kyle’s lockpicking skills are second only to his pickpocketing. While I draw the interview long listing quotes from successful businessmen and touting our billion dollar idea “the squatty urinal”, Kyle sneaks into their hotel rooms and accomplishes the task I hired him to do. Then, relieved of their tickets out of the country, I can pay the interested (or less interested) hires the low-ball salary I offered instead of the compromise pay we’d agreed upon. I get my team and they get to be a part of the revolution hitting the public restroom world where it hurts. Win-win.

That’s it. Ask yourself these questions and think real hard about your answers. This is the only personality test that matters if you want to hack it in the valley. I made it. Will you?