How to win at startup

Mostly made to be a joke, highly opinionated, 100% fun to read.

Alex Loukissas
3 min readFeb 3, 2020


Photo by Japheth Mast on Unsplash

Back in 2016 when I started my entrepreneurial journey, I did the same as going into any new field: try to devour as much information and advice from people considered the best in their field, i.e. learn from the winners. Kind of like when you start getting into basketball, you want to imitate someone like Kobe (RIP), so that you (maybe) reach their level.

So what did I do? Read a bunch load of books, listened to a ton of podcasts, subscribed to some newsletters, and in general, I consumed (terrible verb) a lot of content. Although I learned quite a bit from this, I believe the high-level advice I would give to my younger self in 2016 would be this:

  1. Build something people want. Famously, the YC motto that was probably coined by its co-founder, Paul Graham. I would augment this motto with get your product to customers’ hands as fast as possible.
  2. Don’t die. You (of course), but also your startup. As I’ve seen pointed out by a lot of people (most recently in the amazing interview with Jason Fried on the Knowledge Project podcast), most successful companies are those that have managed to outlive their competitors. But how do you do this? Start charging from day one and charge more. It’s important that you know what value your customers get from your product and expect them to pay for it. A great recent example of that is Superhuman. At first glance, it’s a really, really expensive email client (as in, $30/mo expensive). But, as its founder explains here, their users find the software extremely useful and happily pay this price.
  3. Build a product for businesses, not consumers. If it solves an extremely boring and totally unsexy problem, even better. You get bonus points if that problem is as close as possible to how the company acquires its customers, sells its products, and best, collects payments from customers. Yes, building cool sexy apps or products for consumers looks fun and hip. But those customers are expensive to get, have smaller budgets, and can (and most likely will) leave you for the next, hotter, shinier competitor at a moment’s notice. As Steve Jobs (never) said: stay hungry, stay boring.

But I want to build a fun and sexy consumer startup!

Good luck to you. But if you do, I would maybe advise focusing your product to satisfy one (better: more than one) of the seven deadly sins. Too weird?

Here are some examples:

  • Lululemon: help people seem that they’re into fitness (even if they may mostly wear those yoga pants to brunch), while making their butt look almost as good as a serious yoga instructor (vain, pride).
  • Tinder: help people who may have normally sucked at picking up dates IRL cast a 100x wider net, make them look cooler at first impressions, and maybe get them 10x more dates than before (lust, pride).
  • Instagram: help people who may not really lead a much more exciting life than their friends (ugh, followers) show off their specks of glam life, travel, food, etc (pride, vain).

So, where do I go from here?

  • Stop reading this.
  • Talk to your future customers.
  • But mostly listen. Learn to ask good questions, sit back and take notes.
  • Get something in their hands, like, yesterday.



Alex Loukissas

Engineer. Optimist. Always building side-projects. #LongLA