The Quit Your Day Job Investors and EPs Preview Their New Oxygen Show [Interview] 

Who doesn’t dream about finding their passion and finding a way to make it pay? Some people fall into their dream job, but I’m more interested in the people who make their own luck. In Quit Your Day Job, we meet  features aspiring millennial entrepreneurs who receive the life-changing opportunity to pitch themselves and their innovative ideas to the angel financiers. The investment club — Lauren Maillian, Randi Zuckerberg, Ido Leffler and Sarah Prevette — use their business expertise, industry knowledge, and creative vision to determine which up-and-coming products have the potential to be the next big thing. The investors provide on-site, hands-on mentoring to the young professionals, who must prove they have what it takes to turn their concept into a viable business.

So, how does this work? The investors surprise everyday entrepreneurs in person to see if they really have the drive, ambition and commitment to take their products to the next level. Based on the experts’ observations and feedback, two start-ups with the most potential advance to the final round, where they are put through a field test to convince the investors that they are worthy of their financial backing and mentorship. After intense deliberations, the investors reveal if one, both, or neither of the prospective businesses will receive a commitment of funds. The caveat: All four investors must unanimously agree in order for a business to receive their venture capital. This high-stakes series proves that you don’t need an MBA to have a good idea . . . you need passion, hard work, and the drive to do whatever it takes to succeed.

I hope this show sounds exciting, because I’ve seen this episode and I went through a range of emotions while the fate of these 3 potential entrepreneurs was on the line. Not everyone listens to the advice their given and not everyone does well with the challenges. There are really stakes here and you feel that.

Back in January we attending the Winter TCA event for this show. The investors as well as EPs Philip D. Segal and Kevin Williams talked about the challenges of starting your own business, their own stories of success and failure, how they chose who to invest in and working together on the show.

What’s the biggest misconception people have about trying to start their own business and go after their dream job?

Lauren Maillian: “The biggest misconception is that it’s easy and you can just create something because you feel there’s a need for it and that the rest of the world has to buy into your vision.  So the toughest thing for an entrepreneur – and the same thing that’s been hard for all of us and that we all work on every single day and that we encourage entrepreneurs on the show to do – is to be receptive to that feedback and to evolve and adapt every day for the better good of the business, not just themselves.”

Randi Zuckerberg: “I also think there’s a view in our society that to be an entrepreneur, you’re a young man at a tech company. That’s not the case. Dreams are still alive in America, and it’s really amazing to see so many women, so many ethnic minorities that are out there. If we can give those people a chance, that’s a real win for all of us.”

Ido Leffler: “There’s never been a better time in history for anybody to become an entrepreneur. The hurdle used to be around technology or around access. Today each and every one of us has a computer that is more powerful than anything that existed 20 years ago. The fact that for $1,000 for a laptop, if you’ve got an idea, you can make contact to the people that can help you get to where you need to go and literally quit your day job.”

Sarah Prevette: “Oh, good plug.”

Ido: “On Oxygen.”

It’s great to have a platform for somebody to be an entrepreneur and for this show to provide that. Did you find with some of these people that as they got more into it, their hurdles were so insurmountable that either they decided not to proceed or it took a real huge push from you to get them over whatever hurdles there were?

Sarah: “That’s the beauty of this show. It shows that really gritty entrepreneurial journey, right? You get the backstage access to see just how much grit and resilience it takes to overcome those obstacles. I can’t give it away and tell you who didn’t make it through, because you are going to have to watch the show for that. There’s a lot of really great companies, great entrepreneurs, and not all of them receive an investment, and some of the ones that do receive investment, I think you’ll be surprised.”

Ido: “Frankly, I wish there was a show like this when we all started our businesses to give us that look behind the scenes to actually realize what it takes when you have to go make that pitch to a Fortune 500 company, which happens on our show. That idea around walking in front of an investment group and having to not just sell yourself and your idea, but to actually prove that you can do it, which is what the in-depth look of the show gives. It’s very unique.”

Randi: “I also think that’s why it was so important, as part of the show, that we actually gave real world challenges to these entrepreneurs. At the top of the show, they come into the office. They pitch us. But then we actually go out into their offices, into the wild and work with them. We threw challenges at people that, quite frankly, if they couldn’t rise to the task in a 24 hour challenge, how could they ever expect to rise to the challenge of being an entrepreneur?”

Ido: “The bravest thing was actually our producers, because we didn’t follow the rules. We would make up these challenges—”

Randi: “On the fly.”

Ido: “—as we met these entrepreneurs. We would meet them. We would see the things that they were lacking and challenge them to overcome that. The fact that they stepped up was phenomenal and this show proved to us more than anything that if you set people the challenges, they will surmount them in spades.”

Philip D. Segal: “I think that’s part of the fun of the show as well, to see the risk you have to take to break down that barrier and try. The takeaway for the audience here – and it was a great journey, a learning experience for us – is to watch them overcome this risk. Yes, these are investors, but they’re also mentors, and I think that risk, to not take it is the greatest risk, and we don’t often get an opportunity to see that dynamic, so the point of your question I think is one of the most powerful aspects of this show, is watching that barrier get broken.”

Lauren: “We take such a deep dive on this show that every entrepreneur, they’re always hearing, the first impression is so important. So of course everyone’s [got a] great first impression. We break down that facade and we figure out if their barriers, their hurdles and the things they’re struggling with are personal, professional or financial. Then we mentor them through [it]. We challenge them. We see if they can rise to the challenge, but we’re really able to take a 360 view to this entrepreneur in a fairly short period of time between the four of us to, hopefully, make what we think is the best decision.”

In the course of doing that, for any of the investors, did the phrase “Well, when this happened to me” come out of your mouth at any point?  

Lauren: “Oh, gosh, yes. I think a lot of the entrepreneurs came on the show because they were familiar with our personal journeys and because they saw a little bit of themselves in one or all of us.”

A show like Shark Tank, the investors there need people coming on who have a proven professional and financial track record in terms of their entrepreneurship. At what level do you accept people?Do you take people with just notes on a napkin?

Randi: “Yes, a very early stage. I mean, we have people come in with just an idea in their head, a drawing on a napkin. I think that’s what makes this show so exciting. Even today, as we were going through some of our conversations, practically everyone would take us aside at the end of the interview and say, ‘Hey, I have a business idea, too. Can I pitch it?’

Everyone has that idea. The beauty of our show is that you don’t have to already be rich. You don’t have to already have access or technical skills or knowledge. If you have an idea and you come to us and we resonate with you on a product on a personal level, you can get that made.”

Ido: “There was a perfect example that you’ll see in the series of a specific woman who, frankly, when she first approached us, chances are we would never have given her the light of day. She had an idea that was practically on a napkin. To see the transformation in this woman- watch out because this woman is a rock star. To see what she will become over the next few years is going to be an incredible story and we fell in love with her. It’s magic.”

Kevin Williams: “There’s some pretty big differences from the shows in this field, entrepreneurial shows that exist and what this is. One of them is, by nature, a younger show. These guys made their way at a younger age, and they are already turning around and mentoring and giving back at an earlier stage.

But, they don’t just sit in a room, take one meeting, and then haggle about it. This show was like jumping off a cliff as a producer because we literally shot across the country in their homes. They wanted to see their families. They wanted to see their process, the garages where these things were being made.

There’s a mentorship and there’s a real challenge that’s going on between these investors and those entrepreneurs. Then when we get to the end of the shoot, it’s, like, “I guess we are going to Seattle now to do a whole design thing. How in the world are we going to do that?”  And, honestly, it’s the scariest show I’ve ever been involved with. Now, only in retrospect, am I not as scared, but it’s amazing because every page is a different story.”

Philip: “I think that’s one of the most powerful aspects of getting an opportunity to do this and that’s why we were so excited when Oxygen allowed us to do this and tell this story. Personally, also, having a millennial, you often see hopelessness and sometimes just lack of direction. I think that one of the takeaways that I loved about this show is that opportunity to empower. So it works on a lot of different levels, not just that idea of have a great idea that checks off all of the boxes. Otherwise, you don’t come in.”

Ido: “We walked into a couple’s home that was basically living on food stamps. The fact that they were willing to risk all of it to make a better life for their family, whether or not their idea was good or not, was remarkable. It showed us a part of this country that is so, so encouraging, to show that people are willing to step up and make a stance and really fight for their family’s survival.

For other people in this country to be able to see this journey through this show is going to make people step up. I think this show is going to literally make people walk into their boss’s office and say, “Thank you for the opportunity, but I quit my day job.” That is something that is not for everybody, but I think it’s going to encourage a lot of people to step up and hopefully make the next generation of entrepreneurs come to life.”

How did you choose the entrepreneurs and how many are actually in the show?

Randi: “Some of them, we dug into our own Rolodexes. I think, between us, we come across a lot of incubators, a lot of different entrepreneur groups. We didn’t just want to tap into the same pool of entrepreneurs that we know. That’s part of what drew me to the show, is the fact that we want to introduce a whole new generation of entrepreneurs.

I worked in the Silicon Valley the past 10 years. I’m so tired of being the only woman in a room. I think it was really important for all of us to branch out and find those entrepreneur communities and people have dreams that we don’t even know.”

Ido: “As investors we get, I want to say at least 2 to 20 approaches a day through social media channels, through LinkedIn, about people who want us to look or invest or mentor them in business. The biggest challenge of this show was that we could only see three per episode.

As this grows and as we see more and more people, we probably could have filled an entire slate for the next series based on the fact of just how many people came to us and said, ‘I want to quit my day job.  I have got an idea.'”

Randi: “So we are taking casting for anyone who has an idea.”

Ido: “Who has an idea? The beautiful thing is that everybody has an idea and we wish, as entrepreneurs, that we could help everybody that comes our way and delve as deep as we did with the folks on this show.”

For the investors. I know you guys knew each other and were friends before you started this project. Can you talk a bit about your history and whether that was a plus or minus when it came to the competitive aspect?

Ido: “It was amazing to walk in day one and just feel comfortable with the fact that Sarah was going to be hitting me in the stomach and that Lauren and Randi and I, that we’ve all had this honest chemistry that was real. We didn’t have to hold punches and that we could be honest with one another.

But, at the end of the day, the big, unique factor of this show is the fact that we have to make a unanimous decision when we invest. That is not easy when you get four personalities such as ourselves in the room, especially when we disagree. There were times that it was unanimous from the get-go, but there were times when it was definitely not and I’m dying to see that episode.”

Lauren: “There’s this ultimate decision which, yes, has to be unanimous, but you’ll also see that we often disagree on the best way for that particular product to get to market. Maybe we all agree on the fact that it’s a product that we are interested in moving forward with, but maybe we think it should be wholesale versus direct to consumer versus, e-commerce versus some other multilevel marketing or something.

So we have a lot of respect for each other and that is really important. That’s a foundation that binds us and that’s made us successful. But we are competing counterweights to each other on this show. There are times that we are like this [hands in a fist and touching each other] on a product and our advice to an entrepreneur. There are times when that entrepreneur is, like, “Oh, gosh. Should I listen to what Ido says or listen to what Lauren says?” You are going to take all of this and now you have to make that executive decision on what you think is right for your business.”

Randi: “And it’s our own money. So I could think Lauren, Ido and Sarah are the nicest people in the world, but if they are saying something that I disagree with, that doesn’t make me want to pull my wallet out and invest a significant amount of money in a company. There are definitely a lot of times you will see that on the show, that we are in disagreement, and at the end of day, it’s real dollars and real investment money that’s going into these companies.”

Ido: “If all else fails, I just use my Australian accent to convince them of the wisdom of their investment decision.

Randi, what types are you attracted to? Just tech types of projects on this show? And what are some of the biggest lessons you’ve learned while you’ve been at Facebook and building Facebook?

Randi: “I think one of the biggest personal challenges for me in this show was stepping out of my comfort zones and looking into spaces that were unknown to me. In real life, I’m generally drawn to tech, social media, app-type investments.

In the first episode of the show, everyone told me I was going to be assigned to go to the woman pitching the Weave Scratcher Pro and that could not be farther from social media or tech investing. It really made me think, ‘Okay, so many people would write this woman off right away?’ I see male VCs in Silicon Valley doing that all the time to women. They just write them off because they don’t have personal experience with that.

So it was important to me and, I think, to all of us that we open up our eyes and never just write an entrepreneur off because it’s an area that we are unfamiliar with. That was my biggest takeaway from doing this show.”

Ido: “And isn’t her weave lovely?”

Randi: “Coming from the bald man.  Thank you, Ido.”

Edited for space and content.

Quit Your Day Job premieres Wednesday, March 30th at 10/9c on Oxygen.