My First Million: How hiring four assistant got me there
Your Biggest Vision
Season 3, Ep. 61

I’m not Miranda Priestly, but I did have four assistants over the course of two years. In this episode, I outline just HOW this happened, the mistakes I made, and the benefits I finally tapped into that allowed my business’ growth thanks to my team.

You’ll hear:

  • The biggest mistake I made when hiring an assistant that wasn’t the right fit-
  • What I wish I would’ve known about hiring assistants beforehand
  • Exactly what about team support allowed my income to scale so much
  • How my team allowed me to take a maternity leave for a business than bears my name

Now, we want to do the unheard of and come in as your in house HR team to help you find, train and integrate your next (or first) assistant. Learn more about our Assistant Training Program HERE.

Tune into this week’s episode to hear in-depth about my journey with assistants, what I learned about the power of hiring & training the right people, and how our team can help you do the same to break through to your next level.

(Click here to tune in)

Tune in to hear about my journey with assistants, what I learned about the power of hiring the right people, and how our team can help you do the same.

Hear the Episode

Episode Transcription

Leah Gervais:

Welcome back to your biggest vision show. Leah here, and today I’m excited to bring you behind the scenes of my assistant experience. What it’s been like for me, hiring assistants, what it’s been like for me with ones that were great, what ones were not so great. Uh, and just a little bit of an honest conversation around it, because I, like I’m imagining many of you entrepreneurs out there, did not necessarily know I was going to be a team leader when I started my business. 

I know it might sound kind of obvious, but I think a lot of us start our business because we want to do what our business does. Right? I wanted to talk about starting your own business and being entrepreneurs and quitting your nine to five job and doing things your way, and becoming a leader just wasn’t on the forefront of my mind.

So there were a lot of reasons that, being chief among them, that I was late to hire an assistant. And then when I did, I didn’t really think about it in the way that I encourage you to now. And I paid for that. Um, so anyway, all this is to say in today’s episode, I wanna take you through what it was like hiring my first assistant, hiring  my second, my third and my fourth, and know that yes, in the last two years I have had four assistants.

Before you think I’m like Miranda, Priestly-style, a la Devil Wears Prada, I wanna really break this down because there’s actually been so many blessings that have come with all of these assistants, namely, that most of them have risen up in my company and have more leadership roles at this point. And that all started with them being an assistant.

So I’m sharing this for you. If you are listening to this and you are in that maybe six figure phase, you are really psyched about the money you’ve made, but you’ve kind of done it all alone. Maybe you are making more than you, you know, thought was possible at the beginning, you’re in an exciting place, but you know that you’re not gonna get more hours in the day.

The only real way you can do this is to scale in a big way, to scale is by growing your team, or maybe you’re listening to this and you have an assistant and they’re awesome, but they really aren’t taking as much off of your plate as you know, they could, and that’s not necessarily their fault. It’s almost like you don’t even know what you need to tell them to do in order to take more off your plate.

And you feel kind of like directionless in terms of what more they could do. I also wanna speak to you here. And then this is also for you, even if you’re not like, regardless of the income milestone you’re at, if you just are thinking about hiring someone because you need help, right? But that’s gonna look different for all of us. And you don’t know where to begin. I also wanna support you in that too.

Before I dive into the meat of my story and some tips I have on hiring an assistant, thinking about hiring an assistant and mistakes that you don’t wanna make when hiring assistant, I wanna make sure that you know about our new assistant training program. So as I alluded to out of my three assistants of the past four, two of them are now in leadership roles in my business.

Not only are they higher up in my company now, but they’ve actually hired now my new assistant. So they have experience being my assistant. They know what the inside of my seven figure business looks like in some ways better than I do, which is super cool because they have seen all this. They’ve built out the systems, the structures and the processes that have allowed us to grow in that way. 

Before I had my, my sister, Abby, who was my second assistant before I hired her, I was like at the $20,000 a month ceiling. And I really couldn’t break through. And six months after her, we hit our first six figure month and I’ll get into all of that. But my point is the people on my team who are part of this assistant training program, know the ins and outs of a successful online business more than almost anyone else you can find.

And they’re here now to help you go through that, they’re here to now show you what that can look like, how you can make that happen for yourself, what it can mean for your business and for your income. And they’ll do the training for you.

We built this program because we saw our own clients need it. And we actually did this with a few of our clients before we offered it publicly. They were doing so well on their own, and we knew they were ready to hire someone else, but they just didn’t have the time to properly hire someone. I know I’ve been there where you’re like, I desperately need help because I have no time on my hands. And I so don’t have time on my hands that I can’t even hire someone, let alone train someone, right?

Raise your hand. If you’ve been there, I’ve been there more than once. So to have my team come in, me and them to do whatever you need to bring this assistant up in your business. And it doesn’t necessarily even have to be an assistant. Maybe you want more of an operations person or a social media person, and you just need to have them have more ownership over what you’re doing, but you don’t have time to train them. We’re here to do that for you.

Over the course of eight weeks, we will hire your assistant, train them and integrate them into your business, including building out the system to keep you organized and you on top of it and your business growing that you probably desperately need, or that you don’t have time to build yourself. Or that could be improved. When I started out, when I started hiring my assistant and growing my team, I was still using Google docs for everything.

And my now operations director, who’s one of the people that you get to support you in this program, came in and she was like, okay, we need a project management system. And she built out our whole Asana deck and we, she built out slack for us and she built out our team meetings and everything. So, um, anyway, all this is to say that if you’re interested in growing your team, but you either don’t have the time or don’t have the background or don’t have the confidence in doing it yourself, we’re here to do it for you.

This is something brand new that we’re offering. And for this week only you can get $500 off of this eight week container. That is it’s $2,997 typically, and you can get $500 off. Payment plans are something we’re happy to work with. That is a crazy deal for the amount of money you can make with a good assistant, right?

With someone who can help your business grow. So let’s talk a little bit about my own journey and why I think our team is the team to help you do this. Even if you didn’t really know that you needed this right now, so to speak. So when I was first realizing I needed a little bit of help, it was actually one of my coaches who told me that I needed help. And I was like, no, no, no, I can’t afford help. I just quit my nine to five. Um, I think that that was the timeline I had just quit. My nine to five. I was still desperately trying to get to a five figure month. I still had business debt, um, from starting, you know, months before. And I didn’t think I had the time nor money to pay someone to start helping me.

And I also wasn’t confident that I would be able to, to take on the responsibility of having to consistently pay someone, right. It’s like, it’s not like a one time investment hiring someone it’s a recurring cost. So you really wanna make sure that you’re getting your return on that investment pretty much from day one. And I just didn’t have that confidence, but I couldn’t ignore it after a little while I was getting in over my head, I was too busy and it would make a huge difference if I had someone to help me.

I also remember it started to feel weird that I was both the administrative person in my business with my clients, as well as their coach for what I did personally, it was like I was coaching them on how to do something, but then also having them sign contracts and things like that.

And it just kind of felt misaligned. So I was also excited about having a little bit more of that boundary, which I highly recommend. Because I waited so long, and because I just kind of did this in a as quick as possible type way. I hired someone who had the most experience in online business. I thought that that would be the easiest transition and it would be someone that could just take on the work right away, take things off my plate, know what I needed before I needed them, and really think it ahead of me.

This was a mistake. Not because I wanna put this person down, but because of a few reasons: one, I didn’t actually take the time to interview other people and see what was the best fit for my growth and who was the best fit for me personally. And I can’t emphasize enough how much you wanna look for someone that is on the same growth trajectory as you and your business.

Because if you’re an entrepreneur you’re going to grow very quickly, things are going to change very rapidly, and you’re really not just looking for a robot type assistant, someone that just generates tasks as you give it to them. You’re looking for someone who can be in the game with you, um, and you know, be excited about what your building and also have ideas for you and really kind of be your right hand man or woman, thinking about things before you even need them.

Long story short, this ended up not being the right fit for me and without getting into details just mostly because it’s pretty boring. The thing I really want you to understand is without the right care and attention when you hire someone, both during the hiring process and as you integrate them into your business, that usually won’t be a good match.

And then, this is what happened to me when I realized that this wasn’t working and we decided to part ways, I was in an even worse situation than I was before I had the assistant, because now my business had grown even more. Our responsibilities had grown even more. My client base had grown even more. I basically had more to do and I had absolutely no one to help me with it. And I felt like I even had even less time to find someone new and I had even less time to, um, onboard the right person. 

I also didn’t really trust myself because I felt like I didn’t really know what I was doing, which I kind of didn’t. So in a moment of kind of desperation, I asked my sister, Abby, who at the time was working at an investment bank here in New York city to just help me with my inbox here and there just because I needed so much help and I needed some things off my plate.

And so I just asked her if she could help me around her nine to five job. And if it just could free up some of my time and that turned into her, leaving her job like three months later to work for me full time. So this was a huge lesson for me and something that I want everyone to feel really excited and free about.

I think a lot of times it’s really daunting to hire an assistant because we want someone who’s as trained as possible and people who do have online business experience or experience in whatever your business is, are obviously going to be helpful for a number of reasons, but it is not the key thing to look for, and the right person who’s on the same growth trajectory as you is trainable. And so that’s what ended up happening with Abby and I.

Though she didn’t have that experience, we were on the same growth path. She was excited about what I was building. She believed in it. She wanted to be on the path with me and she quit her job. And she really believed in, you know, this vision that we ended up up sharing and we still share to this day.

And so sooner than later, I mean right away, I started seeing results from having her as an assistant, as someone who was learning the ropes of my business, the culture of my business, um, that was really learning about my vision and her like systematizing it was so helpful for me and really held me accountable. So like six months after she quit her nine to five job, we were making $20,000 a month when she did that. And then we had our first six figure month. So this was not a mistake. This is not an accident.

This wasn’t just a coincidence. This was because I no longer had everything on my plate. Sounds so obvious. I had more time to focus on the things that generated us more money. I had administrative things off my plate. And most importantly, I had an assistant who wasn’t only doing administrative tasks, right? That’s obvious.

It was someone who shared the vision with me and held me accountable for it and systematized it every single month so that we could just kind of plug and play in it and grow with it. And that’s exactly what happened. So shortly after that, I realized that Abby had become such a valuable part of this team that she really could be in the leadership position. And we could grow our team because this was going really well. And we wanted to kind of continue that momentum. So she ended up moving up and hiring a new assistant for me, whose name is Brooke.

So Abby then starts doing a little bit of the coaching that I do with me alongside. That was her favorite part of what we did. Oops, sorry. She realized she was very good at it. And it was just something she kind of continued to grow into organically, which was great for both of us because I loved that she was a, we were able to serve more people through her, helping me with coaching. And she was really fulfilled by it. She really loved that client-facing role. So she hired Brooke. She put up job listings. She muddled through all these applications. She did video interviews, she narrowed it down to these finalists and then she chose our final hire. Brooke, and Brooke was then my assistant for a little while. And then with Brooke, we had a similar quantum leap.

So Brooke joined in February of last year. And about six months later, we had crossed the million dollar mark. And as you can imagine, this is no coincidence. This is no surprise. Abby being able to take on more. And then Brooke being able to take on more and then having Brooke really be on this ride with us and in this vehicle with us and in momentum with us and sharing the vision was so much more important than having someone who understood Facebook ads, right?

It’s about that cultural connection. It’s about the right person and it’s about the systems in, in place. And Brooke was really proactive and she built those, which I, I really will be forever grateful for her for having done those because it wasn’t even about me taking time out of my business over those months and sitting down with her and like teaching her how we keep track of our goals and teaching her how to have the communications amongst the team.

It was basically me asking her what I thought she, you know, what we needed and because she knew my vision and she knew what I wanted, she was able to create those. And that’s something we wanna bring to those who we help with this assistant training program. I think a lot of entrepreneurs out there have some sense of organization.

Maybe it’s a to-do list. Maybe it’s a spreadsheet. Like I had, maybe you have Asana or Trello or whatever, but to have someone whose literal job it is to go in and make sure that everything you’re working on is delegated aligned with the vision that you have and the goals you’re currently working toward, have deadlines have priority, like are actually in a way that we can’t fail if we stick to it. That’s where your seven figures is. Uh, David Neagle’s, um, CEO once told me that seven figures is just about good planning.

She just said, anyone who doesn’t hit seven figures is just not organized basically. And I hadn’t hit seven figures at that point. So I was like, oh, that’s a  slap in the face, but it’s probably right. But I didn’t have the time to get organized. Right. I was so in deep with my business and my life. And, and by the way, you guys, as I’m telling these stories, like, as I’m going through these years, I simultaneously was quitting my nine to five job, grieving the passing of my father, suddenly getting married, planning a wedding. And you know, that’s no, that’s kind of a part-time job in itself. And then getting pregnant and moving. We moved from New York to Florida and then Florida back to New York and then having a baby. So life only gets busier. The more you have people to come in and organize it for you, the more bulletproof your business is going to be.

You don’t wanna wait until you have time, or you have what you think is going to be time to do stuff like this, because that might not happen. And guess what? That’s not what you wanna do with your free time. Anyway, you should be able to spend your personal time going on that vacation, having a baby, if that’s what you want, planning a wedding, moving, um, you know, buying an apartment, buying a home, like those things that we have our business, this is what it is to make your business work for you and not consistently be a slave to your business. So as we are approaching the million dollar mark, I see what a rockstar Brooke is. I see how much he is part of our team and how much I trust her and how much I believe that she sees my vision, even when I don’t always have the words for it.

And I want to promote her as well. I want her to start overseeing others and growing this with me. So she hires my fourth assistant. And so I’m sharing this with you. One to show you that no journey looks perfect, but two, to help you see how incredibly valuable it is to have me, Abby, and Brooke, come into your business and find, train, and integrate an assistant for you because they have literally built the inside of my business to reach seven figures.

They have done the hiring for assistants themselves. They each hired each other. I hired Abby, Abby hired Brooke, Brooke hired my now assistant Dani, who I also literally can’t live without. So they know how to do this and they know how to do it right. And they know how to do it well. And for you to have that off your plate now, instead of waiting until your assistant is found and trained and integrated for things to start lightening up, that’s where you make the big moves.

That’s where your life becomes easier very quickly. That’s where you scale. And so I’m excited and passionate about this offering that we’ve created together, because I just know that it is going to transform people’s businesses. And I know that whoever takes us up on this offer is going to start seeing a difference in their income, a difference in their work life balance, a difference in their quality of work, because they have more time working in their zone of genius. And we’re so excited to do that for people, you know, this is not something you’re supposed to do alone, and I’m forever grateful for these women. And for my team who have kind of shown me how powerful this is, so that we can share that with others and help them build that business in a really solid way, too. 

And if you have any questions about the logistics of team building, how do we do hourly pay? How do we promise our, do we promise ours? How do we pay people? What kind of software do we use? What about taxes? You know, I’m an open book with that kind of thing. I’ve had to do it all. And I know a lot about it because Abby is a full-time employee of mine, and then we have other contractors. So I’ve kind of experienced it all. And I’m really willing, you know, to share that expertise and talk to you guys about it. So if you are interested in having us either find your first assistant, find your next assistant, or just train your assistant to have more of those systems and structures in place in your business so that you can scale from having this support

Or maybe it’s not an assistant you want, because you just heard my story, that Abby is now the lead coach of our business, and Brooke is the operations director, and I have an assistant. We really can help you with any of those, then go to You also can just find it at under services, or reach out to us and take action, because this is something that can happen so quickly and you can see results from so quickly. Once we can kind of get our hands, um, in there with you and really see the work and the growth with you.

Okay. I hope you guys found this helpful. I hope that it is helpful to see kind of how I started from never having hired anyone or managed anyone or not knowing if I could keep up with the financial commitment or not knowing really how to teach someone and all of that to now having had four assistants, three of whom still work for me and two of whom have been promoted, um, and you know, manage other people now and how cool it’s been to kind of see that step into ownership and to see my business cross the million dollar mark because of it. Please reach out to us. We would love to support you. All right, everyone. I hope that this was helpful. Here is your biggest vision. I will talk to you guys soon.

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