Should your employee have a side hustle?

Jessy Grossman is a long time entrepreneur in the digital media space. She's passionate about supporting women in business and being at the forefront of innovation. She’s been quoted in Forbes and was awarded a spot in the “Influencer Top 50” by Talking Influence. In less than two years she created one of the fastest growing talent agencies in the country. Amidst unprecedented growth, she sold the multi-six-figure agency and pivoted to focus on her long-time passion project: Women in Influencer Marketing (better known as WIIM). Founded in 2017, today WIIM is the premiere professional organization for those who work with influencers. The community offers networking and new business opportunities, career services, continuous education and more. Jessy also does consulting, advising and influencer marketing recruiting with her company Tribe Monday. You can find inspiring stories and more about Jessy on the WIIM Podcast. Check out iamwiim.com and tribemonday.com for more information.



Jessy: Hey guys, welcome back to the Women In Influencer Marketing Podcast. My name’s Jessy Grossman. I know many of you know that cuz you tune in every week. But for anyone who is new, I founded this community called Women In Influencer Marketing, and I also have a consultancy called Tribe Monday, where I help people in all things influencer marketing of course, women is a community hive, mind, a mentorship program, career resources, all sorts of stuff, all related to supporting women on their path in the influencer marketing industry.

This week’s episode is definitely one that I’m excited to chat about. It’s all about employees having side hustles and that can be anything that can be, they’re also a creator. That can be they, create t-shirts or whatever their side hustle is.

But I think that I would love to explore today with you guys the fundamental question, should your employee have a side hustle? So we’re gonna get into that this week. I hope you stick around.

Jessy: All right guys. So before we get into this week’s episode about side hustles and employee habits and just like how to have a great team, I am coming back from LA Today is actually my first day back in New York. It’s nice to be back. I think I’m still realistically processing that whole trip.

It was like three trips in one. The first part was our LA experience, which was the day after I arrived and then I went over to Anaheim for VidCon and that was like a multi-day event. and then I just spent time with my best friend who just had her first baby. He’s three months old. She got baby snuggles for a few days, which was really nice.

So I’ll recap that a little bit cause I’m sure some of you guys are curious. I know I’ve posted a little bit about it on social and yeah, I’ll share a little bit about all that here so you guys can get a little bit behind the scenes. 

So our LA experience, you guys, I feel like if you ask anybody who attended, I hope they would say that it was fun. It was a success. They had a nice time. I think that they would say that, from my perspective, it was a mess. It was a mess. 

I have not experienced that level of stress to that degree in a long time, and we planned the heck out of that event. Events are just a beast. I knew that things would go wrong because with events if you just do enough of them, you know that inevitably things go wrong. Things are, as much as you plan unpredictable things happen.

However, I did not think that it would be to the degree that it was, literally you guys, the day of the event our vendors were supposed to start coming around two o’clock to set up the furniture to like just set up generally we had photographer, videographer, caterer drinks the whole, everyone was supposed to start coming at 2 by 2:15.

I didn’t know if we were gonna have the event. I didn’t know if we were going to be allowed to, and around probably 2:20, I was explicitly told by this dick fire marshal that he was not gonna approve our event for that day. And sorry, but not sorry. 

Understandably I was panicked, literally on the verge of tears, but I think my adrenaline was pumping so much that I was just like, I can’t fall apart right now. And I just went right into problem-solving mode.

I think the part that annoys me the most is it seems like it was completely avoidable, and I just know that that’s just a pet peeve of mine.

I don’t know about you guys, but like experiencing that level of stress and knowing that I didn’t have to feel that at all, was so avoidable. It like makes my blood boil, and makes me so mad. 

And also, unfortunately, I didn’t really get to enjoy the event at all. Like I can get over things. If something goes awry, I’m not traumatized by it. I’m not like sitting around for months on end thinking about how terrible of an experience that was. 

But it legitimately takes me a couple of days, like literally two days, two full days, to come down from that level of disappointment or stress even.

We ended up taking the risk and putting on the event, even though we did not have this ridiculous fire marshal approval, basically, we had to make a judgment call and we decided to have the show go on.

Thank God for the I think we have six or seven people volunteer to help out at the event and exchange for a ticket and thank God for all of you guys, because while I’m like running around stressed the fuck out, trying to get it all together and shift my mindset from this like approval not happening to just producing a successful event, you guys were like getting everything together and like God’s end. Seriously. So shout out to all of you guys cuz I know you know who you are and thank you for all of your generosity.

I think it’s like a major takeaway if I can go on a tangent for a second. During my entire trip to LA, I had so many people who were so kind and generous. And like all these people who volunteered, one of our volunteers came to my Airbnb the day before and helped me put together all of our gift bags.

Like she didn’t have to do that. It was just simply because she was trying to be nice and we got to know each other and we got dinner and it was so her to do that. When the speaker that we rented stopped working halfway through the event when we were playing music, probably two-thirds of the way through the event our videographer was so nice.

And he was like, hey, let me see if I can help you, blah, blah, blah. He’s supposed to be just like taking videos and doing his own thing. And he certainly didn’t have to help. And he stepped in and my anxiety went from here to like here, like a little down, lessened.

And it was just, I don’t know, there were just countless instances where people just went out of their way to just be kind and helpful. And I feel like it really inspired me, to do the same and to pay it forward a little bit. So thank you to all the people who were incredibly kind and gracious to me during my trip to LA. I really really appreciate it. 

But, to put a pin on the event if you check out our Instagram, iamwiim, you’ll see a little video of the event, some photos of it. We had a really incredible panel discussion. That was like really interesting. And shout out to Tagger for sponsoring and Hangarfour four for sponsoring and Create LLC.

We had a couple of those folks on the panel and that was a good conversation. The theme was endless summer, so we had, pool floaties everywhere. We had this really cool 360 photo booth. We had headshots for people’s LinkedIn being taken.

It was good. I can appreciate it through the photos cuz if I’m being a hundred with you guys, I wasn’t having a good time at the moment, which sucks. I don’t know if any of you guys can relate to that. I wish I was, but I was just so stressed. 

Anyways, so then, I took a couple of days after the event and headed over to Anaheim for VidCon, which was a really nice time. The first day that I got there, I just went straight to this outlet mall. And went to town. Love a good outlet mall. 

Got a couple of cool things from the Bloomingdale’s outlet, so nice two, actually, both of them I wore on stage when I was speaking, on Saturday. Shout out to Bloomingdale’s. It was my first job in New York too. Fun fact. 

Anyways, the outlet mall was super fun. I just got to like decompress and like chill and then like casually check into my hotel, get my badge, et cetera, et cetera.

And then VidCon began. It was really lovely. We had an impromptu lunch with people in WIIM. We have a VidCon Slack channel that we like to reinvigorate every year. And I posted in there, I was like, Hey, whoever’s at VidCon this year anyone wanna impromptu meet up for lunch? and three of you guys came. And it was just like really lovely.

We talked about all kinds of things from work to babies to fertility issues, to what it is to get a babysitter. It was really nice getting lunch with you guys. Shout out to you guys who came. It was really lovely to see you.

I did a mentorship session at VidCon, which was a very humbling experience. I was supposed to have 20 people show up and literally one did. Humbling. You guys are humble, like the second you like your head gets a little bit, and your ego is haha, I’ve made it. One person shows up to a session. So that was humbling. 

And look, the reality is I had a lovely conversation with this girl. We’re now connected on LinkedIn. She’s a junior in college, you guys, and I was so impressed with everything she’s doing. I was like, some of the things that you’re telling me about, I just discovered on my own At the age of 36, but you are doing this all as a probably like 20-year-old and you’re still in school. I was so impressed. 

It was really inspiring to meet her. So maybe it was more of a mentorship session for me. And Then Saturday I had my panels, and one of ’em was phenomenal, and the other one, I liked the first one better if I’m being completely honest. The first one was a bunch of WIIM members that I was able to get together to be my panelists. We had four women. All in women have been for years. I think all of them had been on the podcast before. 

So we had Katya Allison, we had Christina Jones, we had Christen Nino De Guzman and we had Meredith Jacobson. I’m sure you guys probably have seen them around the community, shout out to them, go check out their episodes on the podcast.

They were all on it at different times and they were, wonderful panelists. So we prepared these questions in advance like we all had just really good chemistry. And I felt so good about that panel. I know they recorded it. I’m sure they do. I hope we can get a copy of it. I would really love to share it with you guys.

Maybe we’ll have a whole podcast episode just of that panel. That would be really really cool. In case you, couldn’t freaking spend a thousand dollars on a ticket to VidCon. It’s a whole other conversation. Check out my LinkedIn actually, I posted a recap about Vidcon, my thoughts about it, and what could improve, but that one panel was really fun. 

And then the other panel wasn’t bad. I felt ill-prepared for it. And it was put together at the very last minute and it felt like that. And I just, ugh. had been wanting to speak at VidCon for years. Like no one would give me the time of day.

I’ve partnered with them for the past couple of years to give our members a discount on tickets. And we explored last year, like a whole bunch of different things that I pitched to them, and they inevitably said no to all of them. Like was so excited that I finally met someone who worked on the programming side of VidCon, who was willing to gimme the time of day and have me speak there this year.

And he not only gave me one panel, he gave me two, one of ’em. He’s like yeah, put the whole thing together. So I grabbed a bunch of women from WIIM as I did in the mentorship session. I was so excited. So like, that second panel just was not prepared and it felt sloppy, to be honest to me.

I was just really disappointed because I know how much it meant for me to be there and how much I had worked so hard to get onto that stage. And so to let that opportunity, like to treat it like that was really disappointing to me. So I’m glad that I got to, because at least I got to experience that one really positive experience.

And then from there I just went to go visit my best friend who just recently had her baby. He is just the sweetest. You guys, it was really scratching that itch with Zoe, who some of you guys know is my stepdaughter. I only had her in my life since she was three. She’s almost eight now.

But I missed that baby phase. I’ve never really been around babies my whole life like it just never really happened. So it was just really nice to spend time with my best friend catch up, and mostly just hang out with her little baby. He’s just the sweetest thing and I really enjoyed just decompressing and just like truly taking some days off.

I’m probably gonna do a podcast episode in the future about what it is to have freedom in your life because of the business that you run. I’m very mindful of the fact that I own my own business and I can just take a week off and that’s okay to do.

I know that’s not everybody else’s experience, but if that’s something that you want, it is totally possible. So if you guys are interested in having an episode about like, how to make that a reality for yourself, comment on the YouTube video of this podcast and let me know. And if you say that you’d like me to do an episode on that, I will totally do an episode on that.

But today’s episode, as I mentioned in the beginning, is all about employee side hustles. It’s a topic of conversation I’ve been wanting to chat about with you guys for a while and we’re gonna get into it today. thanks for listening to my recap of my LA trip. I would love to hear from you guys if you attended the event. If you liked it, if you enjoyed it, if you attended VidCon, if you enjoyed that too.

Again, like the best place to share this stuff is on our YouTube channel. So check out our YouTube. We’ll link it below, so you can just go right there, leave a comment and let me know what your guys’ thoughts are. All right, let’s get into this week’s topic. 

So there has been, a resurgence, I would say, of people who are working full-time roles as employees at a company and also simultaneously having a side hustle.

I’ve changed my mind about it over the years. I will be honest and say that years ago when I had a team and I was hiring people myself, I just wanted their focus to be on my company and my vision, and I didn’t want them to be distracted. I didn’t wanna question like if they were on their phone or on their computer, are they just doing their business or are they doing my business?

And I think that like many years, removed from that and having a bit more perspective. I’m all for employees having side hustles. Like all of us, all of you guys who are listening and watching, we’re like multidimensional people.

And I feel like maybe like your early twenties when you know we had more of this hustle culture anyway, where you are solely focused on this one job and you are giving it your all and that’s your only focus. 

I feel like nowadays, like, especially post-pandemic, there are just a lot of us who need to scratch an itch, like a creative itch, and get a little bored by doing the same thing all the time. Basically, by having a side hustle, I just equate that to having another passion, something that’s important to you.

And I am all about, being passionate about your work. So that’s what it equates to for me. And I know that it like, could really invigorate a person, it could make them better employees for you and your business that you do together. In fact, I would put money on it that it would, so I’m all for it.

I think the real question. In our industry is when that side hustle is that they’re a content creator, so they’re working at an influencer marketing company, and on the side, they’re a content creator. And is that okay? I know a lot of people have mixed feelings about it, and I know some people draw a bright line there and say, that’s not what I want for an employee in my business.

And I get that. I really do. I appreciate it and I think it’s a very personal decision. I do think that it depends on the role of course, and what they do for your business. If it’s a clear conflict of interest, I understand not having an employee do that. 

However, what I wanna do is shed light on what the possible benefits could be. And again, I’m not saying to have all of your employees be creators, but when you find someone who is really great at what they do for you and your company, and they also wanna be a creator, they also are a creator. I don’t think you should immediately like, say that’s not okay. 

I think even in the hiring process, if you find a candidate, that’s fantastic, but they happen to also be a content creator, don’t disregard them simply because you made this arbitrary rule in your mind and you believe it’s a conflict of interest, and I will tell you a million reasons why, but a few today.

One perspective is so important. So if you have a person who’s like running campaigns, let’s say, and they’re also a creator, that perspective is going to be so valuable in their interactions with the creators as the campaign manager. Why? Because they understand when things go awry. They speak that language. They understand like how to communicate something to get what they want, and they just empathize. They get it. 

And I feel like creators or anybody like appreciates having somebody on the other side empathize with them. So that empathy and that perspective are really important and valuable. 

I also think that. They’re out there doing it. They’re out there seeing what’s working, what’s not working. And so let’s say you have someone on your team who’s more of a strategist, more high level, and they’re out there experimenting on their own channels, what methods are really getting traction? Tactics and strategies that make their content pop.

That experience, that hands-on experience is so much better than like the theoretical one because all of us can preach all day long about, I believe that we should do this with the strategy or that with the strategy this with the content, the social media, et cetera.

But to actually have real-life hands-on experience doing it and seeing what’s working and what’s not working in real-time, cuz they’re experimenting on a regular basis, it’s just like a really positive attribute. It’s a positive skill that they are honing in on a regular basis. So I think it’s great. 

I also know that people get concerned with, if it’s a content creator that’s on your team, are they gonna basically steal contacts or take that opportunity to pitch themselves?

And look, I think that fundamentally you either just need to trust somebody or you don’t trust them. But if they work for you and they’ve earned your trust, and they are explicitly telling you that I would never pitch myself to somebody, I would never take contacts from you for my own purposes, then I think that like you just need to trust them until they’ve proven otherwise.

The reality is influencer marketing is a relationship business. So many other industries have this too, so we’re not that special. But basically, if you have employees that are really digging into the relationships and really exploring them with people that you’re doing business with, you want that to be the case, and you either have to trust these people or you don’t, but if you don’t trust someone because they’ve done something that’s shown you, they’re not trustworthy, they shouldn’t work for your company anyway.

But I think that people are trustworthy until they prove otherwise. I think that, if a creator is saying to you that I’m gonna work for your company and I am gonna be respectful of these contacts and I’m not gonna pitch myself, then I would believe them.

I just fundamentally don’t wanna live in this untrustworthy state. I understand that some people have been burned in the past, and so for you, it could be really hard to do that. I think that it could also be really hard for you to trust again, I totally appreciate that.

But ultimately I just think you need to trust him. Or you don’t trust him, but this in between where it’s I’m gonna have them be on my team and I’m wondering what they’re doing and I’m micromanaging things like people just need to be given permission to fly, and to soar. And if they’re given that their work is just gonna be infinitely better.

the last thing I think I just wanna stress and so many other people in the creator economy got in here because we’re creatively minded. So if you have an employee that just needs to flex that a little bit more, whether it’s like their own business or they’re contributing to somebody else’s, or it’s simply just something for fun, but they monetize it like there is no shame in that.

We are living in a different world than we were, 10 years ago, 20 years ago. When like this probably wouldn’t be as possible as it was before, but I think that it is okay to say that, your employees can have side hustles because it just ultimately, in my opinion, makes them better employees for you and it makes them better human beings.

And at the end of the day, I just want employees who are really talented and fulfilled human beings. So I think the answer to this, at least in my eyes, is just taking a much more human approach. And you could disagree, you could agree. I would love to hear what you guys think. Do you currently have employees who have side hustles?

Are you a little salty about it? Do you think that it’s a good thing that you should encourage? Do you think it’s just something you should accept, but you turn a blind eye but you’d rather it not be happening? I’m curious what you guys think, but yeah, there are course certain circumstances and contexts that matter around all this, but ultimately I think it’s okay.

I think it’s a positive thing actually, and what I said before is I think the best way to sum it up, which is I just want happy and fulfilled humans as my employees, goes a really long way, and I did not used to feel like this. 

So again, check out our YouTube comment on this because I want you guys to give me your thoughts on this topic.

Thank you, guys, so much for tuning in, and we will see you next Tuesday. Bye, guys.


Founder of Women in Influencer Marketing and CEO of Tribe Monday

Jessy Grossman is a long time entrepreneur in the digital media space. She’s passionate about supporting women in business and being at the forefront of innovation. She’s been quoted in Forbes and was awarded a spot in the “Influencer Top 50” by Talking Influence. In less than two years she created one of the fastest growing talent agencies in the country. Amidst unprecedented growth, she sold the multi-six-figure agency and pivoted to focus on her long-time passion project: Women in Influencer Marketing (better known as WIIM). Founded in 2017, today WIIM is the premiere professional organization for those who work with influencers. The community offers networking and new business opportunities, career services, continuous education and more. Jessy also does consulting, advising and influencer marketing recruiting with her company Tribe Monday. You can find inspiring stories and more about Jessy on the WIIM Podcast. Check out iamwiim.com and tribemonday.com for more information.

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