Jen Paxton, VP of People and Talent at Privy dishes about her dream retirement | Liquid Assets

Posted by LearnLux

It's 2021, and talking about money is still taboo for a lot of professionals. That's why we're uniting HR and benefits leaders for candid conversations around career and finances. Join us for our next chat with Jen Paxton, VP of People and Talent at Privy.

Rebecca Liebman, CEO of LearnLux sat down with Jen to enjoy a "liquid asset" and talk through:

  • The money advice she'd give her 16-year-old self
  • Her dream retirement
  • What she'd do with a $5 Million dollar benefits budget, and more.

Prefer to watch the interview? Click below to launch the video, or read on for the full Q&A.



Rebecca: Hi, I'm Rebecca . I'm the co-founder and CEO of LearnLux. Welcome to Liquid Assets, the interview series where we have candid conversations about money and careers. And today I'm joined by Jen Paxton, the VP of people and Talent at Privy. Excited to have you here. 

Jen: Thank you for having me. 

Rebecca: And of course, in Liquid Assets spirit, we have really interesting drinks with us today. I think I just have iced coffee in a coffee mug. 

Jen: I have ice tea in a teacup. 

Rebecca: So cute! Let's start off with a nice and easy one. If you could go back in time and meet with your 16 year old self, what piece of financial guidance would you to share?


If you could go back in time and meet with your 16 year old self, what piece of financial guidance would you to share?

Jen: That's a good one. Yeah. I think for me, I'd probably say "start saving" then. I definitely did not start saving until really  after college. And, I had to be really, really frugal.


What did you spend your first paycheck on?

Jen: This is, this is funny. So I have like my high school job. So I was fundraising. I was part of this touring choir that basically traveled all over the world, but to get to travel the world, you had to pay for it. So I would fundraise, I worked at the ballpark in Arlington doing concessions.

And so a lot of that paycheck went to traveling. So I I've, I've been to a lot of different countries.  If you're talking like real first paycheck, like that would be what I spent it on. 


What is one big financial goal that you're saving for now?

Jen: Ooh. Um,  I want to retire early and I'm trying to figure out how I can retire full-time early. I think, you know, when I get to my  sixties, I'd like to do some consulting on the side and kind of be, you know, maybe be on a board as an advisor, but to get there, I need to actually save up enough money to, to make it happen. So right now, my husband and I, we've saved about three months of a buffer. So we have a lot of room to grow there, but I think that would be my big financial goal. It's going to take a few years to get there. 


What is one purchase that you've made that you regret now?

Jen: Ooh. I didn't regret it at the time, but probably do regret it now. It's not just one particular purchase though. I have lots of clothes and lots of really nice shoes that I never wear. I've worked at startups for almost 10 years now where I wear yoga pants and some kind of, you know, tennis shoe or slippers to work.

So it's really funny to think about all the fancy clothes I have. So I don't know if I like exactly regret it. But I also am kind of like, they just sit there and take up dust. I need to, to figure it out.


What has been your favorite work from home purchase? 

Jen: I hate exercising, like really, never had a gym membership ever. Uh, but three of my really good friends, had a Peloton and basically said "Hey, I think you would like this."

And so me, never taking a spin class beforehand, bought a Peloton randomly out of the blue. And I love it. I've had it since September and I have already done almost 200 rides. I'm addicted. Like I ride every single day for at least five to 10 minutes. If it wasn't for quarantine, I probably wouldn't have done it. So I'm thankful for it. 


Describe your dream retirement. 

Jen: Oh, okay. The one thing I want to do is still kind of have my foot in the door in different startups. I don't know if I'll be like 80 years old and be like, finally, I don't want to  talk about a startup or talk about some kind of scaling growth problem. But I want to be able to make more of my own hours and maybe not work as much. And then I want to be able to travel more. So one thing I really envy is my in-laws actually, uh, before COVID hit they had a trip planned at least once a year to some really cool place. And I'd love to be able to do that with my husband as well. So I think that would be a good retirement.


Did you talk about money growing up and if so, what were those conversations like? 

Jen: Oh, man. I was not talked to a ton about money growing up, but money was a huge divider and my family.

My mom was the breadwinner in the family but she also spent way more money than my dad did. And I think it was always an area of friction where, you know, it was just, "what are we, what are we spending our money on?" My mom was really good at finding deals, but then also, we just get so much like so many things.

I have kept the "deal hunter" kind of stuff. But I also have like more restraint, I guess, on like buying as much. And so now like it's like a trigger in my head of like, "Ooh, 50% off at like, Old Navy," then like, "Ooh, but do I really need another pair of pants? I have a lot of pants."


If you could hire one celebrity to join your team, who would you choose?

Jen: This is super difficult, actually. I would want someone who is like a comedic relief basically because I think that would, just really work well for, for stressful situations. If I was picking for me and Rachel who's on my team, I'd probably say Tina Fey because she would go really well with both of our personalities. And I think that every joke would land pretty well. Um, I would go with Tina Fey for now. Yes. 


If you had $5 million to spend on any benefit for your team, your entire company of employees, what would you choose? 

Jen: So our team is small, Privy is 68 people. That's why I'm like $5 million goes a long way. Um, because we could do a 401k match, which employees have asked about what we don't have. We could also potentially put in a health savings account - Privy pays a hundred percent of health care, so no one really has to worry about that, but if they have  an out-of-pocket expense that's" kind of nice. Um, yeah, it's hard to pick one of those actually.  I would probably, this is cheating, but I would probably put it into a platform where employees have a few different options to choose. Yeah. So I would probably invest in a platform and then be able to fund it through there.


Working in people and talent, what is the smartest financial decisions you've seen your employees make, and what's an area where you think employees could improve? 

Jen:  Ooh. Um, I would say the smartest one is still investing in 401k as early as they can. I didn't do that in my first few startups cause I wasn't really well aware of it. Hindsight is 20-20 looking back and like, "Oh, I could have had so much more money for retirement later on if I didn't."  


What career advice do you have for women graduating college this year?

Jen: I have two things to say that I wish that were were told to me earlier on. One actually was kind of told to me. The thing I would say is, start your own path and be okay kind of defining your own path. When I graduated from college, I had friends that  jumped into getting married and having kids. And I went on to grad school and I was encouraged to do whatever I wanted to do.

I wasn't feeling pressured for it.  And then the other thing I'll say is just advocate for yourself early on, like start off small.  It could actually be in college, advocating for yourself, you know? If you're in a job right now and then like advocating for your worth and what you're able to do. Every pay raise, and actually a lot of the roles that I've gotten and, and gotten, you know, maybe higher than the salary band might've called for is cause I asked.  I advocated for myself as much as I could so that I could actually get what I thought I was worth.

And I used market data to back it up, of course, but can't be shy when you're talking about your accomplishments and you need to be your own megaphone, right? If you're not going to advocate for yourself, don't expect other people to. 


This has been a crazy year. What advice do you have for aspiring HR professionals entering the workforce this year? 

Jen: The first thing that popped to my head was trust your instincts . I'm biased because I didn't come out of school with an HR background whatsoever.  I just kind of fell into it. But you have really good instincts and being able to  lean on those is going to help you more than what you learned in a book. Especially if they're going into a startup environment, be prepared to be flexible, I guess, too.

Rebecca: Absolutely. Yeah. Thank you so much, Jen. What a great conversation. Let's do our final Liquid Assets cheers.

Jen: Cheers!


Thank you, Jen for helping smash the sigmas around money and career! For more interviews in the Liquid Assets series, click here. 

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