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How to Know When It’s Time to Quit Your Day Job

Oxygen and Sheknows Media presents  Quit your Day job , March 24th 2016 30 Rockefeller Center, New York.Oxygen and Sheknows Media presents  Quit your Day job , March 24th 2016 30 Rockefeller Center, New York.
BaubleBar founder Daniella Yacobovsky (left), serial entrepreneur Ido Leffler (center) and Zuckerberg Media founder Randi Zuckerberg speak on a panel focusing on entrepreneurship in New York City.Tiffany Hagler-Geard Tiffany Hagler-Geard

When should I quit my day job and focus on my own business full-time?

It’s a tricky question that has crossed the mind of nearly everyone who longs to take their side hustle to the next level. Entrepreneurship can be exciting, but taking the plunge is not easy. There are so many issues that can crop of along the way: What if you get in arguments with your co-founders? Or your business pitch falls flat? What if, after days of not enough sleep, you burst into tears following a failed product launch?

All of these scenarios — and more — are captured in the new Oxygen Channel show, Quit Your Day Job, premiering March 30 at 10 p.m. ET/PT. The reality series, in which millennial entrepreneurs from across the country pitch their ideas to in the hopes of getting funding, highlights the pitfalls of early stage entrepreneurship. It also offers strategies on how to deal with common setbacks, thanks to advice of the show’s four star angel investors: serial entrepreneur Ido Leffler, founder of Zuckerberg Media and former Facebook exec Randi Zuckerberg (yes, she also happens to be Mark’s sister), model-turned-entrepreneur Lauren Maillian and Sarah Prevette, founder of Future Design School and Sprouter.

Related: The Unexpected Payoff of Failure

The cast’s four investors were joined in a panel last week by BaubleBar founder Daniella Yacobovsky and Melissa Ben-Ishay, the founder of Baked By Melissa, to discuss the ups and downs of entrepreneurial life.

Here are some of the best pieces of advice the panelists had for entrepreneurs looking to launch their first business.

1. Show investors they can trust you

Leffler: You can never ignore the fundamentals of any relationship – business or otherwise. You need someone you can trust. We have a one-strike policy when it comes to trust. Screw us once, we’ll never do business with you again. By the time somebody gets to me in an investment stage, I want to picture that person stuck with me on a deserted island.

The other thing we look for in a pitch is someone who knows their stuff. Be confident in your idea, be willing to take criticism, and know your stuff and know your numbers.

Oh, and don’t call your business, “The Uber of something.”

Zuckerberg: Come in with data. When you come in with things like, “I’m going to work really hard,” or “I really want this,” that makes me want to give you stickers, not money. When you come in and have real data, it speaks volumes.

Yacobovsky: When you’re looking to raise money, the interview should go both ways. When you take money from someone, they don’t just give you money and go away. You spend a lot of time with them, so you have to really like them. When they’re investing in your passion, there is nothing more horrifying than being stuck with someone that you potentially don’t trust. Get references on that person. Find people who can talk to you about what they’re like as investors when things go sideways because, inevitably, things do go sideways. Make sure you’re taking money from the right person for you.


2. Develop a network of advisers

Maillian: When you come in, don’t tell me you have no advisers. I don’t care if it’s your dad’s friend, you must have somebody.

Ben-Ishay: You have to recognize from Day 1 that you’re not going to do it on your own. Surround yourselves with people who have skills that you don’t. Recognize what you’re not good at. I had the product, but I didn’t have the food background or the experience working in a bakery. So I created a team of people who had skills that I didn’t, and that’s ultimately what propelled us forward.

Related: Gary Vaynerchuk Credits His Success to This Personality Trait

Leffler: We call this “The Power of Five.” Everyone has five people who can help them get to where they want to go. Find out who those people are. If we all had to dissect our career path, five people made it happen.

3. Take time for yourself and for your loved ones

Yacobovsky: Remember to celebrate the wins. Pause and take a moment to feel good about something you’ve achieved. It’s important to have those moments of celebration and pride to keep giving yourself the motivation to continue.

Leffler: When I started my skincare company, my wife was my girlfriend at the time. I would be on a call, park my car, walk into the house, give her a kiss, go into the study and continue my call. I did that for about a year. One day, I walked into the house and her bags were packed. She told me she was going to leave me unless she could have my undivided attention from 7 p.m. to 9 p.m. She said, “After that, you can do whatever the f— you want.” That changed my life. This is something anyone can do. If you’re single, it’s your time to go to the gym, to watch a movie, to do whatever. Make sure you have those two hours of the day to connect to the real world and not be on your phone.

4. Understand you have to play by the rules before you can make your own

Maillian: I talk a lot about being able to finally make your own rules. Unfortunately, sometimes we need to bite our tongue and crouch before we can conquer. Sometimes we have to play by rules we know are unfair until we can make them, break them, and change them ourselves. Is that right? Is that fair? Should it be that way? No. But life isn’t fair. Obviously don’t let everyone walk over you, but realize that you don’t have to fight every battle because you’re not going to win in the end. It’s been my hardest lesson to learn as an entrepreneur.