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Let's Build with Shegun Otulana

The Tuesday Roundup

Published 3 months ago • 1 min read

If you’re trying to decide whether to take your startup full-time, you need to be realistic about what it will take. This article from Foundr takes you through a mental model to determine whether it’s time to go all-in. You need to know what you’re getting into and prepare – and this includes financial preparation. Their perspective is more risk-averse than mine, but the key message is effective: understand what it takes, but also be willing to recognize when it’s time to just go for it.

“Realize that you’ll never feel completely ready to make the leap. That’s just part of being an entrepreneur—jumping into the unknown. No one is ever ready to graduate, get married, have kids, buy a house, move, or quit their job to build their own business. Yet, we eventually make the jump.”


Once you’ve decided to go all-in, you need focus, grit, and perseverance. Cofounder of Dropbox Drew Houston offers a detailed look into what it takes to win. His story is a good lesson in the basics of success. You have to believe in what you’re doing – you’ll never have to courage to take the leap if you don’t. When you truly believe, you have to focus and drill down on making it work. A key to this is learning. Move quickly and learn as much as you can.

“If you’ve never started a company, or worked at a smaller company, you’ll run into a vertical learning curve, Houston says. There’s no way to know everything you need to from the start, so you need to a) gain as much knowledge as you can as fast as you can, and b) plan ahead to learn what you’ll need months down the line. You have to be prepared for a never-ending conveyor belt of challenges.”


Kathryn O’Day also has some great resources on what to focus on as you get started. Again, learning (and learning quickly) is essential. Don’t forget to keep having fun and taking care of yourself, too.


Whether you’re quitting your job or taking on two full-time jobs to go all-in, you’re going to need to optimize your time. My episode of CEO on the Go contains some of my frameworks for focus, quick decision-making, and prioritization. I recommend finding a system that works well for you and how you work.


Join the Let’s Build Community to get even more resources, plus conversation with myself and other entrepreneurs.

Let's Build with Shegun Otulana

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