How My Team Has Evolved Over the Years: From Solopreneur to Powerhouse Employees

behind the scenes Mar 19, 2024

Go behind the scenes of how my team has evolved over the last 8 years; from good hires to bad and the biggest lessons I've learned as I build my dream team.

We’re currently in a series where I’m taking you behind the scenes of how my business has grown over the years, thanks to a fun question from my dear friend, Laurie when I asked in the Summit Host Hangout Facebook group for questions you wanted me to answer on the podcast. 

We started this series by talking about when business and summit strategies make someone question your ethics. In the last episode, I took you aaaaall the way back and walked through the different stages I’ve gone through in my various blogs and businesses.

This week I'm continuing to answer this question about the stages of my business and how it's evolved by focusing on what my team has looked like over the years. "Team" felt like it's own separate evolution to talk about on its own, so that's what we're covering today! 

My hope with this episode is to inspire those of you who haven’t started growing a team yet or are just starting so you can see what’s possible and get some insights on the process. And I also hope it’s just a fun listen, even if you’re someone who has a solid team of your own.

Let's dive in!

Listen to the episode

Prefer to listen to this post instead? Use the links below to listen on your preferred podcast player:

My First Two Hires

I'll start with the first two hires that I made, and then go into a few mistakes and bad hires that came after that. We'll also go into some of the better hiring decisions I made that make up Team SIAB as you know it today.

Hire #1: Virtual Assistant
My first hire was a VA I brought on for 10 hours per month and that felt huuuuge to me. This was way back in 2016, about 5 months into business, and I wasn't really making much money yet. But I noticed that things like editing blog posts and scheduling social media were taking so long and I needed that time for client work. That hire was definitely a situation of hiring juuust before I was ready and that theme still happens and plays out today. It’s a big part of why I’ve been able to keep growing. Luckily, I’m a very process-focused person, so that part was great from the beginning. I had the step-by-step processes, I was already using Asana, so we were able to get up and running pretty quickly. 

Working with that first virtual assistant was okay. I don’t remember the terms of her leaving, but I do remember there were a lot of mistakes. It was either a situation where I ended up letting her go after a while or one of those really convenient things where I was avoiding letting her go and she decided to stop offering VA services. Either way, there wasn’t much drama and I eventually brought on someone else who was priced way higher than I should have been paying for VA services, but she did a darn good job.

Hire #2: Design Assistant
Very soon after I brought on that VA, so also early-mid 2016, I brought on a design assistant who is still with me today. Even back then, I was always doing all kinds of launches and creating new products, and it wasn’t pretty when I did it. It also took me soooo long! Now, she designs anything and everything I need, full website pages, templates in our programs…all of it. Again, this was another hire that I probably shouldn’t have made if you’d have looked at my accounting records, but it was a hire I needed to make to keep growing. I regret nothing!

So at that point, I had a VA and a design assistant.

A few mistakes 

After that, things got messy for a little bit before I found the right people.

Mistake #1: No idea how to outsource development work
At the end of 2016, I was already getting a few more projects than I could handle and I wanted someone to hand off the simpler things to. So I started trying to bring on other developers to help. 

The issue was, that it was suuuch a long process to get an inquiry from a client, reach out to these other developers, wait for a quote, and then see that their quote was just as much or more than I would have charged. And there were a few projects where I had them do the work and I made no money on it. Several times, they didn’t complete the work on time so then I’d have to do it anyways. It was kind of a nightmare and the first time that I felt like I didn’t know what I was doing when it came to outsourcing.

I should have learned that trying to build some sort of agency wasn’t going to work for me…but it took a little longer for me to learn that lesson.

Mistake #2: Hiring from the Philippines
I stopped bringing on other developers running their businesses in the same way as me because it just didn’t make sense. In Q3 2018, I was also working on starting Summit in a Box and I had a baby, so my capacity for development work was more limited. So I tried hiring again! At this time, hiring people for $2-3/hour from the Philippines was all the rage and it sounded darn good to me, even though I felt a little guilty. But I did it anyway and paid double what they were asking for to make myself feel better.

This one was a mistake for a few reasons...

  1. First, I should have listened to the nudge telling me that it didn’t align with my values to pay someone less than I should have.
  2. Second, the quality just wasn’t there so I spent a lot of time going back through work and fixing things.

I had to cut that off pretty quickly, too

Mistake #3: A bad VA hire
A year later, around Q3 2019, I changed things up again and made a mistake yet again. My awesome VA who had been with me through all this decided to stop offering VA work and I had to find a replacement. At the time, my best friend who also ran a business was looking for more work and was willing to dive into VA work to help me. She was amazing at the work, so no problems there, but again I was paying too much and we had a bit of a toxic relationship and I knew that going in. 

We’d do fine for a long time, but then suddenly she’d get mad at me and totally stop talking until she eventually would just go off on me about how terrible I was. I’m sure I did it to her a time or two as well, but it was bad and it carried over into business. I have no idea what happened, but at the end of 2020, she thought I was upset at her about something (I wasn’t), stopped answering me, assigned all of her tasks me or another team member I’m about to tell you about, deleted her accounts on everything, and disappeared. It was right before Christmas break, so it led to me working through the holidays and was just a terrible situation and a huge lesson, which I shouldn’t have had to learn.

Mistake #4: Another bad VA hire
And then I had one more crappy VA hire a little later in the timeline, but I’m just going to group it in with my mistakes here. I needed more help after that last VA ditched out, and this time I went through a VA agency that seemed to have it all together. I remember on the call I had with the owner, that there was no emotional connection or desire for a friendship involved, which felt weird, but I thought that maybe I placed more weight on friendships with my team than I should. So I went with it even though I really wasn't feeling it. I signed a 3-month contract because she required it. I got assigned to one of her VAs and had the same exact issue. There was no emotion in her communication, I felt like I was annoying her, and the work wasn’t getting completed correctly. Within 1 week I fired her, paid off my contract, and learned another big lesson. 

These mistakes were really crappy, but taught me so much and it’s why my team is where it is today!

Time to build the dream team

I learned several lessons along the way, but the biggest was that I really had to listen to my gut when I was thinking about working with someone new. If my body wasn't screaming "Yes, hire this one!", I had to listen to it. Now, we'll touch on a few of the better hires that I've made that have helped build the dream team.

Hire #3: Podcast Editor
Same as the first few hires, I started the Summit Host hangout podcast and edited it myself for a while, but really quickly realized it was slowing me way down. In 2019, I hired an editor who is also still with me today - Sharon from Just Keep Podcasting. There is no drama, she does a great job, she's always on time, and I love it!

Hire #4: Facebook Ads Agency
In 2019, Facebook ads were doing wonderful things for us. I joined an ads coaching program through Intentional Spark and thanks to what I learned I was able to spend $15,000 per month and make $30,000 back! It got to the point where I didn’t want to manage it anymore, so I outsourced to them and loved it so much. Unfortunately, once ads crashed in 2021, it stopped making sense for me to pay as much as I was paying. We were also in the process of adding the Accelerator to our offer suite and I didn’t know how it was going to go so I stopped our contract. You’ll hear in a little bit that I now have in-house ads support, but if I ever get to the point where I don’t, I’d go back to the Intentional Spark team in a heartbeat!

So from 2019-2020, my team consisted of a contract VA, a design assistant, a podcast editor, and an ads agency. This is where things really start to shift. 

From Contractors to Employees

In early 2020 I finally launched the full Summit in a Box program. With the influx of students to support and the reality of running two businesses, I needed more help than the contract VA I had could offer and I also wasn’t willing to pay those prices. I had heard about the power of hiring employees, but was scared to do it…but I felt ready to deal with it.

I ended up choosing Gusto to manage the HR side of having employees, and it was awesome! It took lots of time upfront setting that up, creating accounts on confusing government websites, creating more official onboarding material, a company guideline, a handbook, figuring out the interview process, and making a job description.

For anyone curious about the process, it was time-consuming, but not difficult. has a lot of really great articles and then Gusto ($100 off with this link!) made the actual hiring process really clear and easy. I didn’t need a lawyer or anything like that. Gusto makes payroll really easy too. None of my employees so far have needed health insurance or anything like that, but Gusto also makes that easy…although not cheap. I do offer a 401k with a small match for full-time employees and that is super easy.

Hire #5: Kate
In June 2020, along came Kate as my Marketing & Operations Assistant. She came from a teaching background and was trained from the ground up on all things online business, summits, and being a VA. She started as a part-time employee with 15 hours per week, and within 2 months was my first full-time employee. I really can’t even explain to you what she does because it feels like everything. This company wouldn’t run without her. She does everything from podcast management and show notes, any and all automations and tech, inbox management, tech support for our Accelerator clients, social media scheduling, managing our physical boxes, client onboarding and offboarding, affiliate management, payment recovery, all of our ongoing daily, weekly, and monthly tasks, and so much more. 

She is such a gift!

Hire #6: Copywriter
This hire actually happened slightly before Kate was hired, but things shifted after Kate came on. So Elli started as a contract copywriter. She wrote copy for random projects but pitched me to basically keep her on retainer, and I loved it! She started off full-time doing things like client support, editing show notes, writing newsletters, and continued writing my sales pages and launch copy. She also dove into the role of our client support lead and Facebook ads manager. She's my second brain for all things strategy and marketing.

She moved back down to part-time about a year later and she leads our client support, runs our Facebook ads, and does our show notes editing. She does a few copy-related projects along the way, too, if I ask her. For my bigger copy projects, I contract with Nadine from Can Do Content and she's wonderful.

Hire #7: Leads Coordinator
Now we're up to 2023, when I joined a program that taught me a new way of getting leads and selling. I dove into it and it worked so well for us that I couldn't maintain all the emails and social media messages on my own. It was leading to sales, so it was a smart thing to do, but it was more than I could manage on my own so I needed to find a Leads Coordinator. I wrote up another part-time employee position, and only shared it on my internal channels like our Facebook group and Instagram, and I quickly got a lot of solid applications. It was a very difficult decision! There were a few people I knew and a few great applicants, but out of them all came Mel. She's wonderful. She's fun, has so much energy, and is the perfect person to put in charge of talking to my audience. She cares about them and makes it fun. 

My current team: The original design assistant and podcast editor, Kate full-time, Elli part-time, Mel part-time.

Hire #8: OBM
I recently hired an OBM because of all the team members I have, the tasks we have, and all the details that go into everything. With our current team, I should be the one going into and doing all those checks, but it ends up bogging down all my time. So I hired an OBM and it's too early to tell you how it's going.

Update: As of posting this, but after recording, the OBM was let go and someone new is being trained in the position. Stay tuned to hear how that's going!

The Biggest Lessons Learned

I've learned a lot over the years about making good, and bad, hires. The biggest things I've learned are:

  • Don’t hire someone you know you have an interesting relationship with. Duh!
  • Fire FAST - if your gut is telling you it’s not working, it’s not going to start working unless there’s something clear you can do to fix it.
  • Allll the systems are wonderful to have.
  • Hire employees over contractors.
  • Be strategic in your hiring process and interviews
    • For example: When I hired Mel, a big part of her job was going to be communicating with our audience via email, so I made sure the application process involved writing me an email. That helped me so much. Mel had me laughing out loud and I knew I wanted her talking to my people.
    • Bring on a team member or friend to the interviews to be your gut check. I had Kaitlyn or my previous VA on the call when I hired Kate, and I had Kate on when I hired Mel. It's so nice to have someone to give you that gut check. 
    • Have them do a sample project on the interview. It really helps to see if they can follow the processes and be a good fit. 

In the next episode, I'm going to bring on Kate, Elli, and Mel and get their take on being on a team like ours, so be sure to check that out!



View related episodes >>

Pin it for later!

Go behind the scenes of how my team has evolved over the last 8 years; from good hires to bad and the biggest lessons I've learned as I build my dream team.Go behind the scenes of how my team has evolved over the last 8 years; from good hires to bad and the biggest lessons I've learned as I build my dream team.

50% Complete

Free: Virtual Summit Prep Timeline

Learn how much time to set aside for planning and launching your profitable, stress-free online summit and use my calculator to set the due dates for you.