How working at a day job can make you a better entrepreneur

Photo via RootStartup
Photo via RootStartup

I’m an entrepreneur with a day job. For a while now I’ve been asking myself if this is reasonable, and I’ve recently decided that it is.

The caveat: I believe day job entrepreneurs can only still consider themselves an entrepreneur if they actively pursue the betterment of the entrepreneurial self.

Put in another way, if you’re not taking advantage of the many resources your company likely has to offer to learn about all the things you know little about, you’re wasting lots of time and making a huge mistake.

I’ve thought about this a lot over the past 18 months at UP Global, and wanted to share a few of the things that I’ve kept front of mind.

Finance say what?

Photo via Shutterstock
Photo via Shutterstock

As a founder there will likely be a period of time where you’ll be the tech team, the manager, the janitor and the ever-important chief financial officer (gulp). Personally, business finance is foreign to me, but I know there will come a time when I’ll need to have a basic understanding. I could put this off and learn as I go, or I can take the time now, while nothing is on the line, to put myself in a better position for the future.

There are probably a number of resources available to you that you never think about. Think about it, and then ask the right resource on your team, and just like that, you’ll be closer to becoming the founder you’ve always wanted to be.

Here’s a template you can use to make the ask. I sent this same template below to my CFO and my questions were answered almost immediately.


Recruiting 101

Before moving into a business development role with UP Global, I was focused on building and maintaining relationships with our customers, entrepreneurs and community leaders. The number of emails I received with the subject, “Know any good CTO types?” was astounding.

This leads me to my next point: Always be recruiting.

The moment you enter a room or hop on a phone call the word “recruit” should be somewhere on your mind. As with anything, people have to like you if they’re ever going to consider working with you.

Actionably, this just means take five minutes to go the extra mile. At the end of a call, send a follow-up email. After an in-person meeting, send a thank-you card. More importantly, have fun and be yourself. When you’re actually recruiting for your future startup, the intentionality you put into this now will more than pay off (that’s what I’m banking on anyways).

networking-redfinTo Network or Not To Network

Every person you meet has a network of people likely foreign to you. There’s no better time to build a meaningful network than when you have a day job. It’s all about your perspective and ability to see an opportunity when it’s right in front of you.

Building a company is all or nothing, which means that as a founder you’re always working. At every event you have a million things on your mind which can potentially lead to missed opportunities. Example: you’re seeking new developer and so you fail to notice the designer on the other side of the room.

When you have a day job, you’re often open to all possibilities that might present themselves. It’s not intentional; it’s just because you likely won’t have the laser-focus that the founder version of yourself will have.

So be intentional about striking up as many meaningful conversations as possible. You can do this whether or not you’re currently a founder, but it’s my belief that it’s easier to be totally open when you’re not so consumed by your startup.

Chet Kittleson.
Chet Kittleson.

Duck, Duck, Goose (provide, provide, ask)

Provide value a minimum of three times before making any asks. It’s that simple. For example, you read an article that you think a contact would resonate with? Share it with them. You met someone at an event that a friend should meet? Make the introduction. These are all small things that show you’re a friend, rather than just a LinkedIn contact looking for help with X, Y and Z.

There’s no better time to provide value then when you’re a cog. Chances are, you’re not going to need as much, which means the amount of asks you’ll have will be lower than when you’re the founder you hope to be. So provide value. Tools like Nimble can be really helpful in reminding you to keep in touch, while Newsle can help you to stay posted.

Practice Makes Perfect

As with almost anything, to be prepared is better than to be unprepared (mind-blowing, right?). If you find yourself in a place where leaving your job doesn’t feel like the right decision, that’s okay. You can still consider yourself an entrepreneur. Just make sure you take advantage of the steady salary and the resources of plenty, for if your “dream” comes true you may be living without both for a while.

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