Former Facebook exec. Paul Ollinger left his job with a pile of money and no plans. But retirement wasn’t all that and he decided to use his financial freedom to pivot to his true love, making people smile as a standup comedian and host of the podcast "Crazy Money". 

“The experience of being retired early was far far less satisfying than I ever anticipated that it would be.”

Paul's money story:

Yeah, I did quit at 42 and I left Facebook without a plan. I just thought, "Hey, I have enough money. I don't want to work and be stressed out all the time. I don't want to be away from my family. I want to be close to my mom who's sick," and I bailed on work and I didn't have a plan, so I thought, "Well, I'll just go be kind of rich for a while." After you take a few trips after you start getting back in shape and work on your golf handicap, one day I came home after dropping my kids at school and I turned on my computer and there was nothing there. It was like, you have no mail. I was like, huh. I was like, I missed work. I missed having a goal. I missed my friends. I missed my colleagues. I missed the challenge of being a part of a team and I was like, well, what now? The experience of being retired early was far, far less satisfying than I ever anticipated that it would be.

Bobbi Rebell:
Yeah, because we talk a lot now, there's this growing enthusiasm for this acronym FIRE, as I mentioned, Financial Independence Retire Early. You have some very strong opinions about that.

Paul Ollinger:
Yeah, I think FI is great, financial independence. I think it's hugely neglected in our country and that we should all work very, very hard to buy ourselves back from the bank and to give ourselves a buffer so that we have the independence to leave a job if it's unhealthy for us, but I think the fascination, the fetishizing of RE, retire early, is hugely misdirected. You don't want to not work. You want to work on your terms and if that's how you interpret RE, then we're on the same page. but you want to be able to do work that's sustainable, that feeds your soul, and that is done in a way that leaves time in your life for things like family and staying healthy. The goal of retiring early and having nothing to do, that's not something any of us should aspire to.

Bobbi Rebell:
Okay, so back to the blank computer screen. You're sitting there, you got no mail, you got nowhere to go. What happens next?

Paul Ollinger:
Well, I had done comedy before I worked at Facebook. I worked at Yahoo. I paid off my student loans and I went and I did comedy for two years before I went to Facebook. Then I got engaged and I just happened to end up getting a job selling advertising in Facebook, but when I left Facebook, I didn't have a plan. I was just walking away from something; I wasn't walking toward anything. After a year and a half, two years, of kind of goofing off and not finding what I wanted to do, I sucked it up and I decided I'm going to write every day, I'm going to get back in the open mics, I'm going to figure out how to reinvent myself as a stand-up comedian at, I guess it was 45 or 46 years old by that time.

Bobbi Rebell:
Wow. What was the first thing you did? What was the conversation like with your family because you are now married and you now have children? If you're comfortable, tell us. You're welcome to tell us all your financial details, but give us some context for what this would involve financially.

Paul Ollinger:
On my very first date with my wife 14 years ago, I told her that I was going to quit my job and be a stand-up comedian and she was in from day one. You might also say she was warned on day one, so we've gone through periods of me doing very, very well in the corporate world and me making very little money as an artist. Four and a half, five years ago, when I really started back after Facebook, I said, "I'm going to commit to doing this, to getting after being a full-time comedian." She was fully onboard. Now, full disclosure, working at Facebook as one of the first 250 employees and getting stock options provided us with a size-able nest egg from which we have enough money to live indefinitely if we don't overspend. That certainly puts salve on the wounds of financial... the questions around finances if you don't have to make a living to feed your kids and pay your mortgage,

Bobbi Rebell:
What is it that you think people misunderstand then about the whole FIRE concept?

Paul Ollinger:
What people don't understand is how much they get from work that they're not computing on the positive side of the ledger. They think about work, they think about, okay, I get a paycheck and then it comes with all these costs of stress and hours and travel, but they're not saying, oh, what I get from work isn't just a paycheck. It's camaraderie, it's an identity, it's respect from colleagues, it's the satisfaction I get from learning and solving problems. All that stuff is really, really important. I mean, look at Maslow's Hierarchy. Belongingness is something that takes us one step above where we would be without work.

“I missed work. I missed having a goal. I missed my friends. I missed my colleagues. I missed the challenge of being part of a team.”

Paul’s money lesson:

Find work that you want to do for as long as you can. Find work that doesn't just pay the most, but that you want to do for as long a period as you can. If you have a dream, by the way, it's a lot easier to chase if you've paid your bills first. Putting a little nest egg away before you chase your dream is a far safer way to do it than just saying screw this when you're 32 and then when you're 55 not having anything to show financially for your efforts of the previous two decades.

Bobbi Rebell:
Do you think there is a danger that some of the young retirees are putting themselves in by, especially, we're recording this at a time when the stock market is extremely volatile, so people may have historic calculations in their savings, but they may not necessarily play out as they expect?

Paul Ollinger:
Well, I think there's two things there absolutely. One is, if you think having a million dollars when you're 32 in the market is going to last you forever, then you haven't lived through too many economic cycles and that million dollars can easily be $600,000 after a couple of bad quarters, so there's that. The second thing is that it's human nature that our wants continue to expand and it's not that we can't manage that as people, and I think we should be very aware of how we spend our money so that we're making sure we're spending it on what we value and provides us with more happiness, but however much you have and think you can live on when you're 32, it's not going to be the same number when you're 42 as perhaps your family expands or your parents get sick. There's all kinds of stuff that's going to happen in life that million bucks that could turn into $600,000 probably won't be able to pay for.

“If you have a dream, it is a lot easier to chase if you have paid your bills first.”

Paul's everyday money tip:

Paul Ollinger:
Be on the same page as your spouse. As difficult as it may be, go sit down and talk about where you're spending your money with your partner because there's nothing more expensive than not being on the same page with the person who shares, not just your life and your household, but the money that you all spend together.

Bobbi Rebell:
Yeah, and I'm just going to add, have that conversation ASAP if you're not already and don't be afraid to actually bring documents and go over what you're actually spending. Right?

Paul Ollinger:
Well, that's the first part is to find out where it's actually going and to say, "Hey, do you know that we're actually spending X on this? Do you feel like, are you getting what you want out of it? Because it doesn't feel like that's bringing us as much happiness as the top line number would indicate it should be."

Bobbi’s Financial Grownup tips:

Financial Grownup tip number one:

My favorite line of Paul's in this entire episode was quote, "If you have a dream, it is easier to chase it if you have your bills paid." The truth is that is not so easy, but it is often the harsh truth. We get so caught up in the romance of going for it that we forget the role of financial stability in getting to our goals. No one wants a comedian who is stressed out about his bills, although actually in Paul's case, that could probably work into his act, but you get what I'm saying here.

Financial Grownup tip number two:

After our interview, I asked Paul how we could score discount or even free comedy tickets. He gave me the inside scoop. He said a lot of the shows don't actually sell out and the clubs make a lot of their money on the drinks and then the other stuff that you buy there, like souvenirs, so they really want to fill those seats and they often do this by sending out last minute email blasts offering free, free, free seats. You need to find out where the comedy shows are in your area or where you're going to visit. Get on those email lists, follow them on social media, so you can be on the list or get the social media tweets or posts and find out when those free tickets are happening.

Episode Links:

• Blinkist - The app I’m loving right now. Please use our link to support the show and get a free trial.

• Paul’s website - www.PaulOllinger.com/

• Paul’s podcast Crazy Money
  
  
  
  

Follow Paul!

• Instagram - Paul_Ollinger

• Facebook - @PaulOllinger

• Twitter - @Paul_Ollinger

• LinkedIn - @PaulOllinger

Some of the links in this post are affiliate links. This means if you click on the link and purchase the item, I will receive an affiliate commission at no extra cost to you. All opinions remain my own.

Comedian Catie Lazarus does not just host Employee of the Month, she also runs the business that supports it. Being the boss means setting realistic expectations for her team, and dealing with those who aren’t on board with her mission. 

In Catie’s money story you will learn:

-The real reason Catie started “Employee of the Month"

-The behind-the-scenes challenges of running a live show/podcast

-The employer side of pay negotiation

-Why Catie is talking about lobsters and diners and how that relates to deciding the right compensation

In Catie’s money lesson you will learn:

-How to evaluate if your pay expectations are realistic for the company or organization that you want to work for or if you need to rethink your approach

-How to tell the difference between being unfairly underpaid, and being paid what the employer can afford

-The benefits of being flexible with your compensation, if the position aligns with your goals

In Catie’s money tip you will learn:

-Her tips on negotiating

-How to navigate the implicit and explicit biases in the work place

-How Catie incorporates her degree in clinical psychology into her business decisions and negotiations

-Strategies to use statistics in your negotiations

In my take you will learn:

-Why and how to take the big picture into account when asking for a raise

-The importance of keeping up your work quality and attitude even if you are turned down for a raise or promotion

-Why it is ok to do something a second or even a third time until you get it right. 

-It’s not about perfection but it is about doing your best, and presenting the best product. 

Episode Links

EMPLOYEE OF THE MONTH https://www.employeeofthemonthshow.com/

Follow Catie and Employee of the Month!

Instagram Catie_Lazarus

Twitter @catielazarus

Facebook EOTM

---

Transcription

Bobbi Rebell:
Support for Financial Grownup with Bobbi Rebell and the following message come from Transferwise, the cheaper way to send money internationally. Transferwise takes a machete to the hefty fees that come with sending money abroad. Test it out for free at transferwise.com/podcast or download the app.

Catie Lazarus:
Well, I paid him and I never used him again. Fast forward, after that show, a very big corporation asked recommendations for audio engineers. So, of course, I recommended all of the people who hadn't asked for that, who had seen rightly. It's not that they devalued themselves, it's that they showed perspective and that, I saw, as a really important trait when recommending someone to someone else.

Bobbi Rebell:
You're listening to Financial grownup with me, Certified Financial Planner Bobbi Rebell, author of How To Be a Financial Grownup and you know what? Being a grownup is really hard, especially when it comes to money. But it's okay. We're going to get there together. I'm going to bring you one money story from a financial grownup, one lesson, and then my take on how you can make it your own. We got this.

Bobbi Rebell:
Friends, people often ask me, "How do I get these incredible and, often, really high-profile guests?" Well, the answer is simple. Perseverance and having high standards. The interview you are about to hear is the third attempt made to get this woman on for you guys. She's amazing. I had to have her on. First, we had a last minute rescheduling because she lost her voice. Then, we actually did tape an episode but she wasn't happy. She has a really high bar and she wanted to re-tape the show. High standards, my friends. Do it till you get it right.

Bobbi Rebell:
Catie Lazarus is a comedian who does not come to anything with less than her best. She joked that she is not a financial grownup but you're going to see, she absolutely is. Catie is running a business. She is making tough money decisions. You may know her as the host of Employee of the Month. It is a live show about working that is also a podcast. She interviews everyone from John Stewart to Lin-Manuel Miranda, Maya Rudolph and, famously, Jon Hamm. Here is Catie Lazarus.

Bobbi Rebell:
Hey, Catie Lazarus, you are a financial grownup. Welcome to the podcast.

Catie Lazarus:
Thank you, Bobbi, I'm one of your biggest fans or, at least, I am a huge fan of yours.

Bobbi Rebell:
Well, I'm a huge fan of yours.

Catie Lazarus:
I was so thrilled when you came to the show.

Bobbi Rebell:
Your new Employee of the Month. Taped live podcast.

Catie Lazarus:
Exactly. Exactly.

Bobbi Rebell:
Celebrity studied extravaganza.

Catie Lazarus:
You know it's funny, 'cause I've had everyone from FBI agents and taxidermists and the lice lady and a former pick-pocket to, as you know, John Stewart and Rachel Maddow and Jon Hamm and Maya Rudolph and some of the others, so, it does range and that's, I think, what's nice about having this One-On-One podcast, as you know?

Bobbi Rebell:
Yes.

Catie Lazarus:
As well as these live shows where you get to see an variety of guests, as you did.

Bobbi Rebell:
And, by the way, it is a beautiful spring day in New York City and I hear the birds chirping behind you because you're a woman on the go so you're taping outside, which is kind of awesome.

Catie Lazarus:
I want to apologize because I know that the sound quality may not be as good because I'm outside, however, once you hear my voice, it actually might be better.

Bobbi Rebell:
It's all good. It's all good and you brought a really good money story. Tell us.

Catie Lazarus:
So, I started this show, Employee of the Month, 'cause I could not figure out how to get a job writing for The Weather Channel. I got hired to be an assistant on A Bee Movie, and I don't mean a B-grade movie, I mean a movie about bees by a very famous comedian and, at the last minute, the studio went with so-and-so's niece. You know I'd have these-

Bobbi Rebell:
Of course. Of course.

Catie Lazarus:
I was walking to the subway, kind of thing. And so I started my show to understand, not just how people break in, but how did they sustain careers. And you're here in New York and maybe this is a good way to say, "When you're starting out on your own, you may not be able to afford an office." Even a wee workspace. You may work from home. It may be DIY and that certainly was the case with my- [crosstalk 00:04:07].

Bobbi Rebell:
It's about being authentic, Catie, you're authentic.

Catie Lazarus:
Well, what I was also going to say on that note is, I made a joke with you earlier. I said, "When you walk into a diner, you don't order the lobster unless you wanna, you know, figure out what salmonella tastes like or find yourself ... maybe you don't wanna go home. Maybe you don't have a place to stay so you would order a lobster in a diner so that you would end up in the hospital and that would be the place you stay that night."

Bobbi Rebell:
Right. So your money story. I need to put you back on track, Catie. Okay. Let's go to your money story. Your money story is about people hitting you up for money. You're this struggling comedian.

Catie Lazarus:
Yes. So my money story is that you want what you want, but you also need to see what's in front of you. And so when people have come to me demanding wages that I just simply couldn't offer, it was as if they had walked into a diner and demanded a lobster.

Bobbi Rebell:
So, what do you mean? They were asking to borrow money or you were hiring them? What was going on?

Catie Lazarus:
I would be hiring people and they would want ... this would happen very rarely, but it happened. It happened with a couple audio engineers where they wanted money that they deserved to get if they are working at a corporation. They deserved to get it, maybe, even if they worked at a non-profit so they were-

Bobbi Rebell:
Wait, so it wasn't a judgment of the value of their work, it was a judgment of your budget?

Catie Lazarus:
Yes. And they're just simply ... It is what it is. It's nothing personal. I wish it was bigger. I wish that I made money too.

Bobbi Rebell:
So what would happen when this would ha ... I mean is there one incident that stands out?

Catie Lazarus:
Yes. Because I have to say that most of the people who worked on my show worked on my show forever and that, I will tell you at the end, why. So I have a really great team in place. But, on occasion, I would hire someone because I needed someone last minute and this happened with one specific person, a guy who came in and he was from a very small town and I always ask before I hire someone, I say, "What do you want to get out of this?" Because I know from my own experience that sometimes working at organizations that don't have as big a name, don't have as much clout or cachet, you, actually, get to do more work and you get to really learn on the job, which is a positive. And I asked him and he said, "I really wanna be part of something small." But the truth was is that he didn't. So he wanted to get paid really well.

Catie Lazarus:
Well, I paid him and I never used him again but, fast forward, after that show, a very big corporation asked recommendations for audio engineers so, of course, I recommended all of the people who hadn't asked for that, who had seen rightly. It's not that they devalued themselves, it's that they showed perspective. And that, I saw, as a really important trait when recommending someone to someone else.

Bobbi Rebell:
Right, because you have to be realistic about what the budget is for the organization that you're working for. It's not that you're not worth it, it's that this is what this is the project is. Yeah, so what's the lesson then from this story?

Catie Lazarus:
So I think the lesson is to look at what you're going into and ask yourself, "What do I want and what can I get?" And if the answer is, "I want to make money." Well, then you should probably go to an institution that has a track record of making money. If you want to be part of a really creative, artistic show that has tremendous potential for learning a skill, for perfecting a skill, for having ownership, an agency, all of those things, my show has always delivered. And that's why 99.9% of my staff has been with me for so long. My team, really.

Bobbi Rebell:
Awe. That's so great.

Catie Lazarus:
Yeah, and they're fabulous and we work together versus working for me. Now, if you're going to a bank, I'm not gonna name any, but if you're going to a bank or you're going to another kind of corporation, there is a sense that you work for someone.

Bobbi Rebell:
Of course.

Catie Lazarus:
Whereas, I treat my show as I work with you, even if you're my intern. You work with me.

Bobbi Rebell:
So I wanna talk about your money tip. It's, sort of, the flip side of this because you're talking about when you're on the receiving end of someone trying to negotiate with you but you also, in your business now, are constantly being in the position of having to negotiate for yourself in an environment that can be very precarious.

Catie Lazarus:
Yes. And so the hardest part, I find, as a creative person or anyone who's independent and particularly in a culture now where everyone has to be a brand even if you're a peace activist, on some level, you, somehow, have to find yourself as a brand. Pro-peace is not enough. With that in mind, I was short changing myself and I'm talking about with corporations and companies, not with other peers. And part of the challenge is is that there are implicit and explicit biases which the Me Too movement and Black Lives Matter and all of ... Pay Parity, all of these things have really shed tremendous light on it. I'm so thrilled that people are speaking out and having the courage to do so because it's really hard. How do you negotiate if women, typically, make less than men? How, as a female, do I go in and negotiate?

Bobbi Rebell:
Right. So your money tip is about how to negotiate?

Catie Lazarus:
So I decided that I was gonna try to be jovial about it and the reason that I chose to be jovial, meaning humorous, it's still serious. You need to get paid.

Bobbi Rebell:
Well, how much you get paid is a very serious thing.

Catie Lazarus:
Well, the approach. Exactly what you were saying, Bobbi, is that you want to not make it personal so it's not that that person is intentionally trying to be biased against me any more than I'm intentionally trying to be biased against someone else. So, instead of making it about us, I would make a joke about now women are statistically paid less than men, so I wanna make sure that neither of us falls prey to it.

Bobbi Rebell:
So you're calling them out.

Catie Lazarus:
I'm calling it out. Instead of-

Bobbi Rebell:
Calling it out. Yes.

Catie Lazarus:
Yes. So I'm calling the problem out versus the person.

Bobbi Rebell:
So can you go through an example of how you use this? What kind of language would you use?

Catie Lazarus:
A lot of times companies will say, "You know, you're gonna to get a lot of exposure if you go with us." So let's say, we're gonna hire you. You may or may not get exposure from that as anyone who's actually has experience in the business knows, including myself, and that's really up to you, whether that's what you're going in to get. If I'm going in because I'd like to pay my rent, pay for the dentist, what money people do when they go for major jobs. In that scenario, it's okay for me to joke about it a little bit and bring up the subject just like I said. So I stick with the facts which is that women are statistically paid less and, in fact, whether you're a woman of color becomes even more of an issue. So I stick with the facts and then I just make a very light joke about, "I don't want either of us to fall prey to it." Part of the reason I do that is so that I don't have to undermine myself either because I also carry these biases.

Bobbi Rebell:
Interesting. So have you changed, recently, in how you approach people when you hire them? Are you looking at people differently?

Catie Lazarus:
Absolutely, in that I really strive ... I'm coming from [inaudible 00:10:44] a doctor in clinical psych. So I think that there's a part of me that always strives to be better at being mindful of who gets hired and on my talk show, as you know, I have as many female guests and LGBDT, I have guests of all ages and careers and all of this reflects on a desire to see the world as larger than myself. Even if it's harder to get certain kinds of guests 'cause I may not know as many people in that age range or whatever it is or that field or whatever the different points are that create true inclusivity.

Bobbi Rebell:
Well, I just want to have one more moment with you to have you tell us a little bit more about the show, Employee of the Month. What's next with it and tell us where people can hear it.

Catie Lazarus:
We're, actually, going to be going on the road, so if people go to employeeofthemonthshow.com, you can find out if we'll be in a major city near you. You can also listen to the podcast One-On-One and I highly encourage you to go and look through the back files because there's everyone from Lin-Manuel Miranda to Jon Hamm and Maya Rudolph on my show and it's a lot of fun. Even Cynthia Nixon before she ran for governor.

Bobbi Rebell:
I know. That's interesting. That's for another show. Alright, and on social media, where can people follow you, be in touch with you, all that good stuff?

Catie Lazarus:
I'm on Instagram and the Twitter and Employee of the Month has a Facebook page which Putin may or may not also be checking out. So you can go to @employeeofthemonth and Catie is spelled with a C, C-A-T-I-E and then Lazarus, L-A-Z-A-R-U-S.

Bobbi Rebell:
You're wonderful, Catie Lazarus. Thank you so much.

Catie Lazarus:
Thank you, Bobbi, as are you.

Bobbi Rebell:
Hey, friends. Here's my take on what Catie had to say. Financial grownup tip number one. When you go to your boss and ask for a raise, be mindful of the economics of the business. You may be worth more but only to another company that has a bigger budget. Sometimes, the company you work for, actually, cannot afford to pay you more or there are business reasons they choose not to, even if you deserve it. If you make the choice to stay, own that decision and do the best job you can. Don't be that person who complains all day but keeps showing up. You know that person. We've all had them at work. I've had them at every job. You just think, "If this place is so bad, leave." Put a smile on and make it work. But it's also okay to leave for a place that can afford to pay you more. Your employer may not be happy to lose you, but the truth is, they probably know that they can't afford to keep you. They will probably wish you well.

Bobbi Rebell:
Financial grownup tip number two. Sometimes, consider a do-over when you aren't happy with the results. Not only did Catie ask to re-tape her episode, I, myself, have gone to guests and asked them to re-tape their episodes or to come up with more original or compelling stories and money tips to share if I'm not happy with the show or the plan for the show they're going to be on. It can be uncomfortable, at first. But every single time, it results in a better show, a happier guest and, often, a thank you for making the effort to make them sound and come off even better than other shows.

Bobbi Rebell:
That is a wrap on the Catie Lazarus episode. If you want to be a guest on the show and have high standards, like Catie, write to us at info@financialgrownup.com to be considered for our new, once-a-month, listener episodes. Include, in the email, the money story that you wanna share, the lesson and, of course, a very original and compelling everyday money tip. Be sure to subscribe, if you have not already, so you don't miss any upcoming episodes and follow me on Twitter @bobbirebell, on Instagram @bobbirebell1 and for more on the show, go to bobbirebell.com/financialgrownuppodcast. I am such a Catie Lazarus fan. I can't wait for the next Employee of the Month podcast. Make sure you subscribe to that, as well. She is the best and thanks to Catie for helping us all get one step closer to being financial grownups.

Bobbi Rebell:
Financial grownup with Bobbi Rebell is edited and produced by Steve Stewart and is a BRK Media production.