Don't Panic - Virtual Assistant Jess Ostroff

Jess knew she wanted to work on her own terms.

What she didn't know, was what a virtual assistant was.

And yet when an opportunity came up to be one, to work remotely and become freelance... she jumped at it. As years went by, the amount of work started to overwhelm her. So she hired her own virtual assistants to help out... and her company Don't Panic Management was born. Everything 'virtual' had gradually become very real.

Jess' story is one of going with the flow, swept along by hard work, consideration and seizing opportunities. Learning the ropes of managing people, managing the finances and managing not to panic. Instead, for the first time, to properly plan a future...

This isn't just a story of how to get started as freelancer. But how to grow from a freelance business to a company beyond your own skills and hours.

Keep scrolling for links to Jess Ostroff online and a transcript, but first make your email feel at home in this box below so you don't miss out on all things being freelance!

More from Jess

Jess on Twitter

Jess' site

Jess on Instagram

Don't Panic Management

Jess' book 'Panic Proof'


Who the hell is Steve Folland?

Steve's a freelancer helping businesses use and make video & audio content in much better ways. Find out more at, track him down on Twitter @sfolland or lay a trail of cake and he'll eventually catch you up.

Check out Steve's Being Freelance Vlog that documents his weekly wanderings and wonderings as a freelancer.

Transcription of freelance podcast interview - Jess Ostroff

Steve Folland:      Hey. I'm Steve Folland. Thanks for listening this time let's find out what it's like being freelance for virtual assistant, Jess Ostroff.

Steve Folland:      Based over in Connecticut just outside New York.

Steve Folland:      Hey, Jess.

Jess Ostroff:       Hey, Steve. Thanks for having me. I'm so excited.

Steve Folland:      Thanks for doing this. Yeah, so well let's find out as ever how you got started being freelance.

Jess Ostroff:       Absolutely well I went to New York University and studied marketing and international business. I thought I wanted to travel the world and make money because who doesn't? It turned out that the corporate environment was not for me, so I decided to try and find some other things to do but being a 22 year old who just graduated college, I didn't know what that was. I decided to do a complete 180 and not do anything business related at all at first. I did an AmeriCorps program, which is like if you've ever heard of the Peace Corps. It's like the Peace Corps but in America. That was something that I thought would be a really great opportunity, give back to the community but also hopefully, learn something new, which is always useful. I also knew that I wanted to get out of New York. I've been there for a while. I didn't love the weather. I don't like being cold and so I applied to a program that was in Los Angeles, thinking all right I'm going to go completely as far away as possible at least in the States and do something different.

Jess Ostroff:       I decided to do a program that worked in schools and I taught Math and Science to eighth grade students, which I hadn't studied math or science in college so that was a little bit of a challenge. But, of course I brushed up on my long division and was able to help them out.

Jess Ostroff:       Once I graduated from that program I was back to square one because I knew that I still didn't want to go back into a big marketing firm or an accounting firm or something like that. But, I was still interested in marketing so I got a job as a social media manager. This was around 2009 so Facebook had been around for a little while at that time. Twitter had just started maybe a year or two before. It started really picking up steam around that time and I thought it was a great way to connect people and connect people that weren't necessarily in the same geographic space. I thought that was really interesting so I worked at this nonprofit as a social media manager but quickly found out that the CEO of the company didn't even know what social media was. I was really fighting an uphill battle that I did not sign up for and that became really difficult.

Jess Ostroff:       Also, if anyone has ever worked in nonprofits it can be just challenging to get through all the roles and red tape and trying to get anything done with any sort of efficiency was really, really difficult. I hated that. I hated that I was sitting at my desk from 8:30 to 5:30 everyday and didn't have enough work to fill those hours. I was like, "Why am I even here? I can get my work done much quicker and then go to the beach or go to the gym or do whatever else I want to do with my life."

Jess Ostroff:       That's when I started looking into other opportunities and it happened to be through Twitter that a former boss of mine had tweeted that they needed a virtual assistant. Of course, I'm 23 at this time, I didn't know what that was. I Googled it, which is always helpful and I applied. I think I got lucky at that time because he knew me and he had worked with me before so he hired me. That's how I got started being a virtual assistant. I was doing 10 hours a week for this particular client and I kept my job at that time and was doing the work before work and after work or at my lunch break, things like that. Then he was generous enough to refer me to some other colleagues of his who also needed virtual assistants. Basically, as soon as I got enough work to pay my rent, I quit my job and became a full-time freelancer.

Steve Folland:      Wow so if you hadn't logged on to Twitter at that moment ...

Jess Ostroff:       Right, right I don't know where I'd be.

Steve Folland:      There was no plan of ... You just knew though that you wanted to work remotely, that you wanted to be able to do what you wanted with your time by the sounds of it, be that working or at the beach and so on and so forth.

Jess Ostroff:       Yeah, I just felt I was motivated enough to manage my own schedule and I didn't like being underneath someone else's control if you will. I didn't mind doing work for clients. I felt that was a different relationship but having a boss where I had to do whatever they said no matter what, no matter whether I agreed with them or not was really hard for me. I learned that I had to really believe in my work in order to do a good job and that didn't work with some of my full-time jobs.

Steve Folland:      How long did it take to build up that confidence or rather that roster of other clients to quit?

Jess Ostroff:       Yeah, it didn't take as long as I thought it would. Even when I first got that first client, I didn't really expect that I was going to be able to do this full-time because I thought, "Wow it's a diamond in the rough situation." I didn't know anybody else who was a virtual assistant. I didn't even know that the industry existed so I really didn't think it was going to be something that I would do but I think it only took about five months. I think I started the conversation with him. Maybe even less, I started the conversation with him in January and I had quit my job by March and maybe had my two weeks' notice so I was gone by April. Maybe even three or four months.

Steve Folland:      Were you getting those people on retainers to give you that confidence?

Jess Ostroff:       Mm-hmm (affirmative). Exactly. I didn't quite do this on purpose at the time. I just was taking any work that I could get. Some of them were project-based so they'd give me a 20-hour project to be done over the course of a couple of weeks or they'd have a five-hour project here and there but even if they weren't on retainer they generally had enough projects to fill my time. I did make sure that I had at least 20 hours of retainer work though so that I could pay my bills. Luckily, at that time I was making practically no money at the nonprofit so I had a pretty low bar of what I needed. I was really young. I didn't have a significant other. I didn't have any dependents or a dog or much of anything so I didn't need much to be able to do it full-time.

Steve Folland:      Actually, just to put this in perspective so what year are we at now when that happened?

Jess Ostroff:       Now, it's early 2010 and I was just frustrated with the system. I felt I had so much to give the world and no place to let my work shine.

Steve Folland:      Well, that sounds like you're saying in on the stage when they write Jess The Musicale. It's a nice-

Jess Ostroff:       You're right. Coming soon to a theater near you.

Steve Folland:      That's what? Eight years ago or so now. What happened in those intervening years? How did you ... At that point, you're also billing your hours. You've got a certain amount of retainer and you don't seem to have much of a plan. No offense.

Jess Ostroff:       Nope.

Steve Folland:      But, you're seeing what happens with this new virtual assistant role you've landed in, right?

Jess Ostroff:       Right. I think that because I was so adventurous I guess I could say, I wouldn't say that I'm a risk taker but I wasn't really risk averse. I felt like no matter what I would be okay and even if I only did this for a couple of months, I'd find something else to do. I had worked in restaurants growing up. As soon as I was 16, I got a restaurant job. I worked in restaurants in college. I always felt, if I needed to I could go back and work in a bar or work in a restaurant. If I needed to make ends meet or even if I just needed some supplementary income, I felt there was always going to be that.

Jess Ostroff:       Also, my family was always so supportive and I felt if I had to go live back with my mom or with an aunt or an uncle or something like that I could. I was really blessed to have a supportive family even though at that point they had no idea what I was doing. They were like, "We know she's in LA and she's somehow making money but hopefully it's not on drugs or something." Because it really wasn't. Nobody else in our family was freelancing. Everyone had a real job and so yeah, it's a little scary to think that your daughter or your niece or whatever is doing something that you don't understand and I get that.

Steve Folland:      Yeah, especially virtual assistants weren't a big thing. They weren't in the common language should we say and also for that matter essentially it looks like you're helping strangers of the internet on their businesses.

Jess Ostroff:       Correct.

Steve Folland:      Yeah, it must be weird.

Jess Ostroff:       If you really think about it, right and that could mean anything. That could be a hotline that you call for other things. Even now, you said virtual assistants weren't a known thing, even now I have to explain what I do and that's eight years later. It's not the kind of thing that everyone knows about. It's not the kind of thing that everyone uses. You have to be an internet professionally or I think a somewhat savvy business person. I mean my dentist down the street doesn't know what a virtual assistant is and would never have a need for a virtual assistant. He has an actual assistant, an in-person assistant. It is still a lesser known industry, I would say.

Steve Folland:      How did it grow from there? You've got a handful of clients taking up most of your time now.

Jess Ostroff:       I was working a lot. I thought this is great. I wasn't afraid of work. I liked working and I liked that I could make my own schedule around my work. Sometimes I'd get up early put in a couple of hours, go to the beach, do whatever I want to do and then come back and work all night. Or, if I knew that I had a dinner, I would put in more of a normal nine to five work schedule. It just depended on what my plans were but I didn't mind working pretty much all day.

Jess Ostroff:       Once I started to feel overwhelmed and feel I had so many balls in the air that I was afraid I would lose one, I thought about, "Well, hey you know people are hiring me to do this. I could hire my own people to help me." I figured I'll keep an eye on it. I'll keep the quality really great and I'll review everything but a lot of this work, anybody could do. My clients as well didn't really care if I did it or if someone else did it as long as it got done on time and as long as it got done well. This was now by 2011, I was starting to think about growing and hiring people. That's when I officially started the LLC and registered with the government and did all the paperwork. Before that, I was just Jess. I was Jess Ostroff. Didn't even have a real business name.

Jess Ostroff:       2011, I decided to pull out the big guns, which by the way it's not difficult at all to incorporate a company. I don't know why I didn't do it sooner but that's when I started Don't Panic Management. That's when I started hiring some of my own freelancers to help me out with the work. Yeah, it took about 18 months for me to get to that point.

Steve Folland:      At this point as long as your clients are concerned, they're hiring you. They have that relationship with you. They love the way you do things. Are they aware that you're then hiring other people to help you with that?

Jess Ostroff:       That's a good question. I don't remember. I think some of them that I did specifically have other people working on, they knew because I would introduce them. I'd say, "Okay, you're going to work with Ms. Marie over here and she's going to help you with your research project," but I didn't have that with all of them. I especially didn't have that with some of my longest running clients. I continued to do the work for the ones that really knew me and really trusted me. It was only until much later that I started to say, "Hey, I started a company and now you're going to be working with a different person besides me and is that okay?"

Jess Ostroff:       I think in the beginning most of the ones I have grandfathered in were still working with me and it was only new people that I would say, "Okay, you're working with Stacy," or "YOu're working with Bob," or whoever it was.

Steve Folland:      How did you find managing other people on top of everything else?

Jess Ostroff:       That was the worst. I mean I thought as most entrepreneurs I just wanted to do the work. I started doing this because I was good at this certain thing and when you're starting as a freelancer, and you're just doing that it's great. You're doing the things that you sought out to do. As soon as you start to grow and you're dealing with more things, it was one thing when I had to send out three invoices, now all of a sudden I have to send out 10 or 20. Now, I have to report my income to the government and do all these papers that I don't know what they mean. Oh, by the way now I have these other human beings that I am responsible for. None of them were full-time so luckily I didn't have to provide health insurance or any other type of benefits but even yeah, managing other people is so hard and I didn't of course didn't know that.

Jess Ostroff:       I would think most of the issues that I've ever faced in my career have been related to people. Whether it's a client or someone that I manage and they don't teach you that. I studied marketing and I didn't ... I wished that we did some human resources and leadership training because I think everybody can use that. It's not just business owners and entrepreneurs but most people as they grow their careers they might start as an assistant or a coordinator but then they're a manager and then they're maybe a VP or something like that. You're always going to have to manage people. I wish that I had some of that training.

Jess Ostroff:       Both of my parents were leaders in different ways and I learned a lot from them. Then I started reading leadership books. I started doing all those things because I realized, I can do the virtual assistant thing. That's not a problem but the whole managing other people, managing expectations, giving feedback. I mean I would rather redo an entire project and do it myself, you know? Than give the feedback that they did something wrong and that's not the case anymore but at the time oh, my gosh. I was just going over, and over things and I was just so nice. I was giving people the benefit of the doubt. I was letting people get away with stuff that they shouldn't have gotten away with and that's not a good way to run a business because you put yourself in danger of disappointing your clients and that was my biggest motivator for doing anything with my business is to make my clients happy.

Jess Ostroff:       Once I got clear on that, I didn't feel as bad giving feedback or firing people because I was, "You know what? This is not about you. It's about the client and if we can't make the client happy here and you're not willing to do what it takes then you're just not a good fit." I made it more simple for myself but I still felt pretty bad. I had to get over that over the years.

Steve Folland:      How about the pricing element of it where once you were just billing for your time but now you're billing for somebody else's but you're still having to manage it so there's a bit of time involved there and maybe I don't know cashflow-wise you might be paying the freelancer before you've been paid by the client and it all suddenly changes?

Jess Ostroff:       Absolutely, that's been an ongoing battle. I think we've finally figured it out eight years later but I remember speaking of that one time I sent a new contract ... Every year we would adjust our prices and clients knew that. They expected that. Nothing crazy, a couple of bucks per hour more something like that, but one year I started realizing that I was severely undercharging even for my services. Based on what everybody else was getting out there and based on just basic needs. I didn't realize when I started as a freelancer that I had to pay my own health insurance and I had to pay for my own computer and equipment. Nobody else is paying for that and that didn't occur to me because I was just going with the flow.

Jess Ostroff:       I realized when I really broke it down I was losing money so I had to change my pricing and I thought that it would be fine and it was fine because what I did was every time I got a new client, I charged them a little bit more. It was the old clients that were a problem. I remember one year, I sent a new contract and it was literally I think the hourly price was double what he had been paying before. He said to me, "Jess, are you telling me that you're going to charge me double for the same work?" I was like, "Yup." I think he knew that my rates were ridiculous and he was like, "Okay." That's when I also said, "All right. Great. I am worth this amount of money." I think that's always a challenge for freelancers to determine how much they're worth. At least especially with women, I think we tend to undervalue ourselves but at the end of the day I just had to make ends meet.

Jess Ostroff:       Once I realized I could charge that, well let me see if I can get a little bit more from other clients. Again, nothing crazy. I wasn't trying to go nuts because I also didn't want someone to feel they were overpaying for a service and when it's a virtual assistant you can only charge so much. I can't charge the same as an audio engineer or a consultant or even a business operations manager. I had to be careful not to go too high, which now you know some people say, "Well, I pay my virtual assistant $5 an hour," and I say, "Well, what happened with that virtual assistant? Because, now you're here talking to me." It's funny when you talk to some people who are like, "Well, I don't want to pay more than this amount," and it's like, "Okay, but you know what you're getting for that."

Jess Ostroff:       I think the other thing for me that I've learned through working with accountants and working with a business coach is what the right profit margin is that you should strive for as a business. These are things that I didn't know. I still manage to grow. I still manage to hire people but I never had that cushion of cash that in the event that something went wrong or if I wanted to send a birthday gift to a client or little things like that, I never had the money for anything else. We were just making ends meet and that was it. Now that we've been able to create a little bit of a cushion it makes me feel more stable. It allows me to pay some of our freelance assistant a little bit more if they are doing really great work. It's not the kind of thing where I can give people raises all the time unless we raise client rates but I think that if you're doing a good job, you deserve something whether it's a bump in salary or a bonus or a really nice gift or something like that.

Jess Ostroff:       Managing people and dealing with money are the hardest things I think.

Steve Folland:      You said earlier, "Like most entrepreneurs," you said something, "Like most entrepreneurs." Was there a point where maybe you always did, where you identified with that word entrepreneur rather than just freelancer? You know when you said, "Just me Jess. Just Jess." Where it felt like actually, "No, actually I'm building something more than that."?

Jess Ostroff:       Yeah, it's taken a while. After I started the business, I was back in New York and I was working at a bunch of different coworking spaces just trying to find the one that fit me the best. Everyone that I met thought that it was a startup, that Don't Panic Management was a startup. For me, that word rubbed me the wrong way because when I think of startups I think of technology or a service product that is new and innovative and that people are going to want but also a company that needs to take investment from other people and I was really proud of the fact that I bootstrapped the business and that I never took any investments, still had never taken any investments or loans or anything like that and that I've built it by myself. I couldn't explain it to people. They were like, "But, you're a startup." I'm like, "No, I'm not a startup. I'm a small business. I'm just a small business."

Jess Ostroff:       All those conversations and growing it organically and trying to figure out what is an entrepreneur? Is an entrepreneur just someone who starts a business? I didn't think that. I thought an entrepreneur was more. I thought it was some bigger role in the world of business and so once I started to be able to provide more opportunities for people and really change the lives of my clients or at least they've said that my team and I have changed their lives, that's when I started feeling like an entrepreneur. I'd say that's come in the last two years or three years maybe.

Steve Folland:      And identifying with that, did that make a difference?

Jess Ostroff:       Yes. I think I definitely feel more confident in what I'm doing because I feel I'm literally building something from scratch. Before, it just felt like well this fell in my lap and now I'm going to just going to do something with it. Do whatever I can with it and now I'm more actively saying, "Okay, where do I want to go with this? Who do I want to help? How can I make a mark in our economy and in our society and in these people's lives?" I feel I'm taking a more active role in my future but also in the future of the business and the future of the people that work with me.

Steve Folland:      Yeah, so within the brand, it's creating that grand beyond just yourself, isn't it?

Jess Ostroff:       Exactly and that's been really important, too, because I can't possibly do all the work that we have now. That has taken a couple of years to say, "Yes, you are going to talk to me. I'm the new business face of the company. I bring in the clients and this and that but you're not going to work with me and is that okay with you?"

Jess Ostroff:       At first, it was hard but now, because we've really built the brand and I've taken my name out of it a little bit, it's been great. Also, because I think I have great people. When someone talks to my colleagues, they're like, "Oh my god, I love Becca," "I love Jen," "They're so great. I'm so happy to be working with you guys." It's not just about me anymore. It's about everyone being onboard with the mission and everyone wanting to serve these clients the best that they possibly can.

Steve Folland:      Do you know what struck me though as you were saying all of that is this team effort where often as a freelancer you can feel isolated quite by yourself working towards something and even if you grow your business and you bring on other people to work with you as you did at the beginning, it's still you driving everything forward and managing everything. But, yeah, it must feel as it were, I presume it must feel great to feel yeah part of something bigger, working within that team, but it's your team.

Jess Ostroff:       Yeah,  I think that I'm very stubborn, and I don't like to ask for help. You may have gleaned that from this conversation. My team now, I have been working with them for about three or four years now and it's taken that long for me to fully trust them and for them to know that they can say, "Jess, stop. Stop being an idiot." They feel comfortable telling me when I'm doing something that's not going to be great.

Jess Ostroff:       I remember one example from last year. He was a friend who came through another friend and wanted to work with us. My one colleague had said to me, "Jess, we just decided with our coach that we're not going to take on clients like this." I was like, "Well, but it's a friend you know and I think we can do this ... " Of course, she was right. I got my way and I brought this client on and it was a bad fit. We ended things on fine terms, which is always good but I should have listened, we made this decisions about the business for a reason and we can't be all things to all people. That's one thing as a freelancer that I have really struggled with. I want to help everybody. I think everyone deserves to be helped but that doesn't mean that every client is going to fit into my core values or the way that I want to grow my business and that's okay.

Jess Ostroff:       There's so many other freelancers and other businesses out there that can help and so that's one another big goal for me, this year is to make more of those connections so that even if I can't help a person myself, I can refer them to somebody who can. I think that as freelancers even if you don't have a team, having a network of complementary freelancers or other businesses that you can talk to and that you can refer people to I think is really valuable.

Jess Ostroff:       The other thing that I'd done especially when I was alone was I was involved in a lot of different communities, social media clubs because I was doing a lot of marketing work. I was in some Masterminds for small business owners. All those kind of things really help you see what you're doing from another perspective and talk to other people that are dealing with the same kinds of issues and challenges that you are dealing with. Once I outgrew some of those that's where I landed was I found myself in all these different Masterminds and I was always the one giving the advice and nobody had any advice for me. That's when I decided I need to bring in an executive leadership coach and a business coach, instead.

Jess Ostroff:       I think when you're not sure where you're at yet, get into a Mastermind and the one that I was in, there was a girl from Bali. There was a girl from Scotland. There was a girl from Australia. There was a girl from Texas. It doesn't have to be location specific and that's what's so great about Skype and having a time zone converter app. There are so many people out there that are either doing the same thing as you or at least dealing with the same challenges and issues as you and you should find those people and talk to them and share. I found the more vulnerable I got, the more that I was willing to share with other people, the more value I got. Also, the more connections and referrals that I got from people because they were like, "I know exactly what Jess does and what she doesn't do. So, I am able to send people her way because we've had those conversations before." That for me has been the ultimate success.

Steve Folland:      You sounded like you started off wanting this flexible lifestyle. Do you still feel like you've got that?

Jess Ostroff:       It comes in waves. After I started in 2011 and then on up until probably 2016, I was just balls to the wall, doing everything and I think was a little bit ... I didn't care about working all the time and I didn't have a lot of goals. I was just like, "Let's grow this thing. Let's do whatever we possibly can to make more money." I had gotten really sick, which I talk about a little bit in the book. That was a bit of a wake up call for me because I realized, I felt I was a superhero. I could work all day. I could go out and party with my friends all night and get no sleep and continue on. At a certain point, my body was like, "Nope, you cannot do that. You have to take better care of yourself," and it was just a matter of time. It was just a matter of hours in the day.

Jess Ostroff:       I had to figure out what things I was most uniquely qualified to do, what things that I should be doing and get rid of everything else. I would say my quote-unquote, "work-life balance" you know I don't really believe in balance per se because I definitely work more than I have in my life, but I think the quality of both is much better now that I've set boundaries around who I'm going to work with, when I'm going to work and also what my priorities are because my health now. I can't work because of myself and because my fingers and my brain are basically my work, I have to be healthy. I prioritize that over almost anything and unless there's a client emergency, I'm going to the gym. I just think that often times you don't realize what you need until you have an incident, which is unfortunate but usually if you listen to what your body's telling you in those incidents you're going to make a positive change and you're going to be much happier as a result.

Steve Folland:      If you could tell your younger self one thing about being freelance, what would that be?

Jess Ostroff:       Know your finances and understand them. Because that was the first thing I always wanted to delegate was dealing with the books, invoices and expenses and the bank account and everything. I needed to understand it better in order to make sound decisions about the growth of the business. I wish I had paid more attention in the early years. I know I had money. I knew there was money sitting there and I never got into trouble luckily but I think I would have been able to be more intentional about the direction of the business and about my growth if I had understood it better from the beginning. That's just advice I give anyone who's starting their businesses. Even if you have someone helping you with your finances, be in contact with them. Have a monthly meeting with them so that you understand what's going on and you understand what each change in the client load or in the expenses, what all of that means for the bottom line.

Steve Folland:      Jess, thanks so much and all the best being freelance and being a boss.

Jess Ostroff:       Thank you Steve. This was so much fun. I really appreciate you having me.