How & When They Grew Their Team

Take your business to the next level by making your first hire! Learn from 20 entrepreneurs who reveal their first hire story today on the blog!

Pat Flynn

20 Entrepreneurs Reveal their First Hire Story: How & When They Grew Their Team

Ah, your first hire. When you’re just starting out, it can be tricky to know when it’s time to start building your team. The key, my friends, is to remember that you can’t do it alone—and that it’s okay to start small.

Like many entrepreneurs, I started out working with contractors for things like building iPhone applications, copywriting, and web design. But a couple of years in, as I was building new passive income streams, I realized I could use help with things like building websites and creating backlinks. Even though I enjoyed doing those things, they probably weren’t exactly the best use of my time.

So I started using sites like Elance and Odesk to find help for a few one-off projects, from designing WordPress themes to transcription work and even article writing. Eventually I hired my own virtual assistant, a programmer who helped build several websites for me and clients of mine.

The experience blew me away—it was like I’d been able to clone myself and get twice as much done. There was no way I’d ever go back to trying to do it all myself.

Fast-forward to the present, and boy have things continued to evolve in the direction of teamwork! After working with Matt Gartland for several years, first as an editor and project manager for my book Let Go, I hired his team as full-time contractors to help me run everything. Then, at the beginning of 2019, I brought them under my wing as Team SPI.

It’s been a trip I could never have predicted a little over ten years ago when I was putting together my first ebook by hand and posting it on my first website.

But stepping back a little bit . . .

Wherever you are in your business journey, you need to recognize the danger of trying to be a superhero and taking on too much in your business. That’s just a recipe for burnout and failure. But looking at where you could use help, both immediately and in the longer term, is what’s going to help you take your small business to the next level.

If you’re in that early but growing stage where you’re starting to stretch yourself thin, I’m a huge fan of bringing in talent to take things off your plate (and yes, do things better than you can do on your own!) whether it’s editing your podcast or helping create a niche site. You can’t do it alone!

Today, we’re going to hear from some special folks—good friends of mine who also have online businesses of their own—about their own first hires, how their teams have grown, and how building a team has changed things for the better, in some cases allowing them to scale and nurture incredible businesses—some making multiple six figures!

These are people who’ve learned, like I have, the incredible power of delegating, entrusting, and building something great with the help of others whose skills and ideas can make the whole of your business greater than the sum of its parts.

Amanda Bond

The Ad Strategist

“I hired a virtual assistant. And I just found that I didn’t really have clarity around why I was hiring that person.”

It’s been about three years since Amanda made her very first hire for her business, The Ad Strategist.

She hired that person, a virtual assistant (VA), after hearing a lot of talk in her industry that made it seem “glorified to outsource, outsource, outsource, as soon as you can, as fast as you can, to get yourself out of the doingness so that you can work on your business, not in your business.”

But shortly after hiring her VA, she quickly found “that I didn’t really have clarity around why I was hiring that person. So it was taking me longer to assign tasks than it would have actually taken me to do the tasks myself.”

Nonetheless, she continued to scale her ad agency, hiring a few ad managers. But she ran into a roadblock there too, because she “just expected these ad managers to immediately get it. To just do things the way that Bond did Facebook ads. And to understand why we were having success.” But they struggled to take the baton she was handing them.

Amand realized that she “hadn’t learned the lesson yet of creating systems to transfer that knowledge. Or productizing our experience for customers.” And so again, she “fell back into the situation of tasks taking longer to train than it would have taken me to do it in the first place.”

At that point, about a year and a half into her business journey with this brand, Amand was feeling pretty frustrated. She was still doing a lot of the work herself, and seriously burning out in the process. She ended up shutting down the services side of the business and running things in a much leaner way, after realizing that the business she’d been running, an ad agency, “was not great for my personality and what I should have been doing with the business.”

And now, three years into her business, she’s back in the process of hiring talent—except this time, as she puts it, she’s “slowing down to speed up,” taking time to read books and absorb strategies that will allow her to find the right players for her team and create a streamlined business that doesn’t require micromanagement. (On her reading list right: Mike Michalowicz’s Clockwork.) [Full Disclaimer: As an affiliate, I receive compensation if you purchase through this link.]

Instead of paying attention to the outside pressure to “outsource everything ASAP,” as Amanda says, she’s focusing on gradually creating “the systems that are going to support our future growth.”

She acknowledges that “from a hiring perspective, I have not done it the easiest and most streamlined way possible.” But through this process she’s learned a ton.

“From initially hiring VAs to hiring the wrong types of people for the wrong roles, to really just not understanding my frameworks and having to take a step back, to now having clarity on how we’re going to move forward to attract the right talent—it’s been a journey. I wouldn’t change it for anything. But it has taught me so much along the way.”

Breanne Dyck

MNIB Consulting

Long term I’m thinking, ‘What are the higher-level responsibilities? What’s the decision making that I want to be able to transfer to someone?’”

Hiring for the first time is something Breanne is very familiar with. “I’ve actually hired for the first time a lot of times because it’s something that we do a lot with our clients.”

“Obviously every time it’s different because every business is different,” says Breanne. As she puts it, “Sometimes the answer is not hiring, and sometimes it is hiring.” So when she started to ask herself if it was the right time to make the first hire for her own business, there was no easy answer.

She was forced to ask herself, “Is this the best time and place to invest energy and time and money to create the next stage of the business’s evolution?”

After some consideration, Breanne decided that hiring was the answer if she wanted to grow the business and take her clients’ results to the next level. She realized she needed someone who could help with customer fulfillment and client delivery. This area represented the “bottleneck” that meant the difference between “where the business was at the time and where I wanted it to be.”

To Breanne, it was crucial to have a hiring plan, because for her, “hiring is a long term play.” She thinks about building a team as an exercise rooted in understanding what people “I want to have around me next year, two years from now, five years from now, ten years from now.”

As an analytical person, Breanne also looks at a whole range of factors when thinking about a potential new hire. How much will it cost? How much revenue will this position create? How will it help improve client capacity? Affect profit margins and cash flow? How long will it be before the new hire is “ROI positive”? She’s thinking ahead, asking, “What’s the next place that I’m going to find a bottleneck?”

At the same time, Breanne says that although she very much operates from a plan when it comes to hiring, “the plan’s not set in stone. It’s going to evolve as the business does.” Ultimately, she’s trying to make hiring decisions that “create the biggest leap forward” for her business and her clients. “It’s not just about me. It’s about how can I build something that’s going to be amazing for everyone it touches,” says Breanne.

Rick Mulready

“I didn’t do it until two years into my business. And the reason for that was really because I wasn’t clear on what I wanted somebody to do.”

Rick made his “first real hire” two years into his business. Although he’d been working with an assistant before then for help with some one-off tasks, he realized he could benefit from steadier assistance.

He wanted to find a “day-to-day assistant” who could help with emails and calendars, as well as someone who could help with the several live launches he carries out each year. He found someone on Craigslist, conducted an interview, and brought him on in a part-time capacity, roughly twenty hours a week.

Three years later, Rick’s assistant is still with him, although still as a part-time contractor because he also works for another online entrepreneur. Nonetheless, the assistant has developed “a ton of knowledge of the back end” of Rick’s business, which has caused his role to shift more toward “ownership of things rather than having everything be task-based,” whether it’s customer service, administrative work, or managing launches.

“It’s worked out well,” says Rick.

Christine Gallagher

“Entrepreneurs are pretty high idea generators by nature, and it means we love to launch new projects, and we chase bright, shiny objects. That also means that we’re notorious for not finishing what we start . . . that’s just one of the big reasons why having a team in place has been so powerful.”

Christine’s company guides female service-based entrepreneurs to step into the leadership role they were meant for with cutting-edge marketing, mindset strategy, and training.

She made her first hire—an admin VA—when she had been in business for about two years, through a personal referral, which Christine says is “the absolute best way to find really good quality team members.”
She hired her VA because she realized she was doing things that were not directly revenue generating that were taking up a lot of her time. The VA initially took over Christine’s weekly newsletter, then eventually started taking more stuff off Christine’s plate, which allowed her to focus on marketing and getting more clients. This helped Christine land her first six-figure year.

Looking back, Christine says, “I wish I had hired that first person sooner.” She now tells her clients that even if they don’t feel like they’re ready to hire someone, they should, because “you’re going to wish you had done it sooner if you wait.”

She took on a second person about a year later, an online business manager who Christine considers “a partner, because she really did help me with more than just sort of the logistics. She helped me with brainstorming around the marketing. She helped me with envisioning a live event and actually pulling it off.”

Christine has found that successful hiring requires “a mindset shift of sorts,” from feeling panicked and rushed to get someone in place right away, to “being more strategic and focusing more on the candidate’s unique strengths and how well they match up to the responsibilities of the role.”

Christine says she “gives prospective team members the Strengths Finder Test, sometimes the Kolbe Assessment, to help find their strengths and what they’re good at and how they’re wired, so that they are the right fit, and it’s not just sort of a guessing game. Because a resume or job experience only tells you so much.”

David Young

“She’s been a great hire, and I think if I had to do it over again I’d probably [do it] in that same order as well.”

When David decided to start building a team, his first permanent hire was for a customer service person who could also handle administrative tasks. David found this person, Jasmine, through Upwork. She handles all customer support inquiries, answers phone calls, and deals with administrative tasks like password resets and refunds.

David hired Jasmine because he was spending most of time on administrative tasks that could be done by someone else as long as they had a good personality, were organized, and were competent.” He wanted to get these tasks off his plate so he could focus on things like creating new products and developing new partnerships with other companies.

Eventually, Jasmine also started taking on larger roles, helping with some affiliates and expanding some of the company’s sales and marketing efforts.

Gemma Went

“I’m very much a believer in finding people that are better than you are at the things that you shouldn’t be doing, and just letting them manage it.”

Gemma Went is a business and mindset mentor from the UK who’s just begun her sixth year in business. She started to build her team about two years into running the business, when she started “feeling stretched and not able to do all of the things.”

For her first hire three years ago, she didn’t “go the usual VA route.” Says Gemma, “I told myself that I wasn’t very good at writing and so, therefore, I froze. I didn’t manage to get out as much content as I wanted to.” So she hired a copywriter to help create content for her. That copywriter is now her content manager, and Gemma loves the “amazing relationship” they’ve built. “She sounds exactly like me because she knows me inside out now.”

Her next hire was a VA who took on things like managing her calendar and inbox and taking over client onboarding. Three years later, this person is now the company’s online business manager, and “pretty much runs the show,” says Gemma.

Two years ago, Gemma also hired a designer to help with branding. And now, in its sixth year, the team is taking on a second VA, a social media person to support the content manager and the online business manager.

Although her team is all freelance, “I tend to build strong relationships with them, and they kind of stay with me forever, which is what I like . . . It feels more like they are employees, and they are very, very invested in the business.”

“I’m very much a believer in finding people that are better than you are at the things that you shouldn’t be doing, and just letting them manage it,” says Gemma. “So I step away and I don’t micromanage, and it works really, really well. I think that’s probably why we’ve been working together for so long.”

Toward the end of 2018, Gemma also started scaling her mastermind group, hiring four coaches to support this growth. Those four coaches are all actually former clients of Gemma’s—people who have been through her program or mastermind. “They understand my frameworks, they understand my systems, and their values are very much aligned with mine.”

Jasmine Star

“There’s a wild opportunity to connect people in your audience, who’ve already caught onto your vision, they get what you do.”

Jasmine hired her very first employee, a part-time business manager, a year into her business.

Jasmine has done most of her hiring via social media, a strategy she admits “seems counterintuitive,” but also makes sense given her lack of previous experience or a framework for evaluating candidates. “The thing that I realized was that without a proper hiring system, I didn’t know how to vet members of my team, so I really just depended on people’s presence within my organic platforms.”

Her business manager became part of the team this way. “She started leaving comments on Instagram, and she would show up on my Facebook Lives. She was such an active member that I remembered her face and I remembered her name,” Jasmine says. Every so often, this person would send Jasmine emails with helpful suggestions about the content Jasmine was creating. She was also a very active member of Social Curator, Jasmine’s paid community.

Jasmine decided to test the community member with a small project to see if there was a fit, and “Boy, oh boy, did she overdeliver!” So Jasmine slowly brought her onto the team by making her a community manager within Social Curator, and then within four months, elevating her to business manager.

The following year, she hired her second employee, a contractor to help with quarterly launches. In 2018, year three, Jasmine’s team started to pick up “a ton of momentum,” growing from two part-time employees to eight, four of whom are full-time. Jasmine is excited to bring on another four team members in 2019.

According to Jasmine, your audience can be an incredible place to recruit talent for your team. “While amazing opportunities exist on LinkedIn and Monster and Upwork, I do think it’s important to understand that there’s a wild opportunity to connect with people that are already in your audience, who’ve already caught onto your vision, they get what you do. They get your voice. They get your purpose, and they’re there to empower you to do it.”

Hal Elrod

Hal Elrod International/Author, The Miracle Morning

“With a new hire, whether they’re an intern or you pay them, by investing that time you are training yourself on how to train someone. So, you’re getting practice—real-world experience.”

Hal runs a business that puts on live events, offers online coaching and training programs, publishes books, and provides keynote speaking engagements.

He made his first hire about four years ago. He and his wife were at a restaurant, and Hal was impressed with the work ethic of their waitress. “Her enthusiasm, her respectfulness, her level of attentiveness, or attention to detail was just incredible,” he says. So he said to his wife, “Man, I need somebody like that on my team. Someone like that as my assistant would be a dream.”

His wife said, “Why don’t you ask her if she’s open to extra work, or a change in careers?”

She was, and Hal ended up bringing this person, Tiffany, on as an intern to make sure the fit was right.

The experience was initially stressful for Hal. “At first it’s actually more of a burden than it is a benefit, because you now have to figure out how to train this person, and how to delegate, and how to effectively manage this new person. If you’ve never done that before, which I had never really done, it was really stressful.”

But he appreciated the “real-world experience” he gained from working with his first employee.

“What I love about starting out your first hire as an intern, is that it allows you to not only test the person, but to help develop your leadership abilities.”

Although Tiffany is now a salaried employee, Hal admits that having her start as an unpaid intern when his business was young and very lean helped ease some of the financial stress. “If you have to pay somebody and you’re trying to learn on the job how to train them, it’s an extra layer of stress.”

Today, Tiffany has become Hal’s director of operations and executive assistant all in one. “She kind of wears both hats a little bit. She handles all of my speaking. She books my speeches. She gets all of the documents to my speaking clients, she handles the contracts, handles the billing, makes sure we collect money, tracks all of that, and she manages my inboxes…”

For Hal, having her on the team has definitely been worth the initial learning curve.

Jenny Shih

“With each person, I was able to train them in how we do things here, and that not only saved money along the way, but also really helped form the culture of how we do things.”

Jenny first started building her team shortly after starting her business, with a short-term hire for some tech help with her website.

Then, after a few months, she realized she could use the help of a VA, so she hired a woman from the Philippines. They built a great working relationship, and she worked for Jenny for several years before going on maternity leave, although she still helps out from time to time.

Jenny’s second hire came about a year later, hiring someone to help with ongoing tech support, updating her website, doing security checks and backups, and other technical things that Jenny didn’t feel comfortable doing on her own.

Then, several years later, although business was going well, Jenny got very sick. She started to need more help, so she hired someone who could help with social media, design, and writing.
She would also hire people for small jobs here and there—“a little design job here, a little copy job there.”

Since then, her team has grown a lot. She has one full-time employee, along with many folks on retainer. “It’s growing quite a bit, but it’s also a whole lot of fun for me to be a part of this collaborative community of folks really trying to achieve big goals.”

She’s also hired coaches for her core coaching program, Make It Work Online. They’ve helped Jenny “refine how we deliver our product, our program to our clients.”

For Jenny, it’s about balance. She says, “I really like keeping my team lean,” and although her team has grown a lot since she started, keeping overhead low and making sure everyone is aligned with the mission is a big focus for her. She has especially appreciated the opportunity to train each new hire “in how we do things here, and that not only saved money along the way, but also really helped form the culture of how we do things.”

She acknowledges that for people like her who are the “expert” or head of the business, “it’s easy to think that we’re the only one who could do [blank],” but the magic begins “when we start to think outside the box a little bit. What skills have we gained in terms of, in this case, serving and coaching clients that we can train other people to do as well as or better than we are?”

Perhaps the biggest takeaway for Jenny from her team-building experience? “When you hire the right people and create the right culture, you actually create better results for your clients.”

Jessica Larrew

“I’m a big believer in outsourcing whatever I can.”

From the very start of building her business, Jessica looked for ways to hire freelancers. “Early on, I hired someone to add a membership program to my website. I hired someone to do design work. And I hired someone anytime I needed something special done to WordPress that I didn’t know how to do.”

Although she “didn’t consider that building a team at the time,” in 2014, almost two years after launching her website, she started “officially” building a team by hiring a full-time general VA from the Philippines from Upwork (at the time called ODesk).

She proudly reports that her VA, Myla, “still works with me today almost five years later. She has been a huge asset to me over the years.”

One of the big reasons Jessica initially hired Myla was to help with email, which Jessica was finding “super overwhelming.” But the decision turned out to be smart for other reasons too. “Hiring Myla made it so that I could get out of the day-to-day tasks like email—plus so much more.” Myla’s multiple skill set meant she could help with things like WordPress, graphics, Facebook community management, “and pretty much anything that comes up. She’s had a lot of different hats over the last five years.”

As a result, Jessica “could focus on things that were really important for my business like creating content and trainings for my students. Now I was no longer just feeling stuck to my email.”

Since then, Jessica has hired several more people, including a customer support assistant, a writer, and a community manager who takes care of the members-only Facebook community.

Building a team has helped Jessica scale her business without dedicating every hour of her day to it. “I’m able to leave town for a week at a time and not use my computer if I don’t want to. I definitely couldn’t have done that before I had a team and I’m definitely thankful that I do, because that is total freedom.”

Lacy Boggs

Content Direction Agency

“She was my manager back in the day. Now she’s managing my team for me.”

Lacy’s business, the Content Direction Agency, is “a small team of rockstar women who help personality-driven brands create strategic content marketing to grow their businesses.”

She started building the business in about 2014, roughly three years after starting another business as a freelance ghost blogger for other small businesses.

Her first hire was a friend who was also a writer and could handle some of Lacy’s overflow. The friend started as a contractor, and as the business grew, Lacy hired other contractors to do similar work, as well as other work outside Lacy’s wheelhouse like design and SEO. “As I grew, it became clear very quickly that there’s only so many hours in the day and so many blog posts I could write in that amount of time,” says Lacy.

Fascinatingly, that first hire was actually Lacy’s boss from a previous job! Although this person had actually been the one who laid off Lacy from that job, they’d had a great working relationship. Lacy says, “I knew I could trust her. I knew she would be great at what we did.” And so making her the “first real official employee hire” was a “no-brainer.”

“She was my manager back in the day. Now she’s managing my team for me. It’s just been a wonderful circle of life, if you will.”

Lacy realized about two years ago that she “was building an agency without even realizing it, because of all these people who had come on as contractors really just to help me with my overflow.” She decided to embraced the idea of building a digital agency and actually becoming the director of the agency herself. She currently has one employee who is project manager/writer, along with three writers, an SEO specialist, analytics specialists, a graphic designer, and a VA.

Azul Terronez

“A lot of the small tasks that we were doing were taking up a lot of time so that we couldn’t move or grow our business in the ways that we wanted to.”

Azul first decided he needed outside help when he started work on his podcast, Born To Write. Tasks like editing, doing show notes, uploading the show, and making sure WordPress was configured properly were taking up much more time and energy than he wanted.

He found his first hire via referral, after another podcaster recommended a VA in the Philippines who could help out with the show. He actually ended up hiring two VAs to work on the show, one to do the editing and the other to create and publish the show notes.

A big advantage was that the two VAs actually knew each other. “That was really helpful,” says Azul. “It allowed me to easily make a transition” away from the repetitive podcast production tasks he had been doing before.

As he continued to grow the business, he started to need help from other professionals, specifically with book design, editing, and publishing. He found them in a few different places, including 99Designs, Upwork, and Breezy, which focuses on publishing professionals. He also found book editors and proofreaders via referrals from people in his network.

Most recently, Azul realized he needed help on the management side of the business. That’s when he reached out to his friends in the SPI Accelerator mastermind program. One of them told him that an integrator might be able to help him apply some management discipline and structure to bring Azul’s ideas to fruition.

As Azul puts it, “I realized I was not an integrator. I’m not a project management type person. I am a visionary. I see big pictures. I like to create.” He found someone via referral and set them up on a six-month contract.

Even as the business has grown and new team members have come on board, many of those hires continue to come from Azul’s network. At the same time, Azul and his team have started tapping larger candidate pools as well, like posting jobs on sites like Indeed. For their most recent hire, a publishing manager, they had the new integrator (officially their “director of operations”) help write the job application and post it. She screened all the applicants, then narrowed them down and sent the final list to Azul and Steve, the company’s chief operations officer, to interview.

Although he’s grown his team using multiple sources, Azul holds a special place in his heart for hiring through referrals from people in his network. He says hiring via this route is “a great way to get somebody who’s worked with somebody who you trust and know.”

Michelle Warner

“I could keep my eye on what I wanted to be creating in the business and creating amazing results for clients, as opposed to just keeping track of what everyone was doing all the time.”

When Michelle started her consulting business, she was recovering from burnout from her prior career in a tech startup—and she knew that was a fate she wanted to avoid in her new business.

About a year in, “when I was getting serious about it,” she hired a personal/executive assistant—but for a slightly different reason than many other entrepreneurs do: to oversee the work of other contractors. “A lot of people in the online space will hire a VA to do technical work, or different tasks. And I knew from my time in the startup world that having an executive assistant allowed that person to oversee things in a way that I would not have to deal with,” Michelle says.

Michelle’s VA has helped out by managing one-off contractors Michelle brings in to help with various tasks and projects. “The model of hiring different VAs to do a bunch of different things and you’re still sitting there trying to manage it all, at least for me personally, is very overwhelming,” she says.

Michelle believes having someone who can help out in this way has made a huge difference for her and the business: “It was definitely the right decision for me.” And it has allowed her business to grow, by letting her “keep my eye on what I wanted to be creating in the business and creating amazing results for clients, as opposed to just keeping track of what everyone was doing all the time.”

Nathalie Lussier

“I started building my team before I felt like I was truly ready to have a team.”

Nathalie’s first hire was a VA who started off working just five hours per week, scheduling newsletters and working on blog posts. Over time, the VA began helping with customer support inquiries, and eventually transitioned to a full-time role as marketing manager, handling Facebook ads and marketing campaigns and training other people on the team to take on marketing tasks as well.

Nathalie’s next big hire (and first full-timer) was . . .her husband. He was “a very important hire for our company, because he is our lead developer.” Bringing him on was “a big step for us,” because it meant quitting his job and making AccessAlly the source of 100 percent of the family’s household income.

The gamble paid off. Since then, business has taken off and the team has grown to eight full-timers. “I definitely recommend hiring a team,” says Nathalie. Although her first hire was “a stretch for me financially . . . without that first assistant, I don’t think my business would have grown to the multiple six figures, and given me the confidence to then hire my husband full-time, and then, from there to pivot our business from online courses and coaching into more of the software business that we have today.”

She also has advice for how to find talent. “Start with people in your local network. Get referrals. and you might think that strangers would be better for your business, because they’ll bring in new insights, but sometimes the people who are already your fans, and who already know your business inside and out will actually have the best ideas, because they’re still outside, and have great perspective, but they’re also really passionate about your business.”

Building a team has also been an incredible learning experience, one that’s improved the business beyond just the individual contributions of each member. “We’ve done so much learning around hiring, and firing, and training, and onboarding new team members,” she says, “and just doing monthly, and weekly check ins with team members to learn what’s working? What’s not working? What can we do better? How can we improve our processes? How can we improve our internal documentation, and our systems? So that it’s easier for everyone on our team to do their job, and also, it’s easier for us as business owners to do our job.”

“That’s why we hire in the first place, right?”

Greg Hickman


“The biggest thing for me when I was looking to hire was to get someone that would help take as much off of my plate as possible.”

Greg’s business is a coaching and training company that helps small, service-based businesses launch a group consulting or group coaching program and deploy their funnel.

It began, however, as a full-service agency that deployed Infusionsoft campaigns for clients. Greg’s need for his first hire came about quickly. “When I first got started, I went out and pre-sold a bunch of clients to help them with their Infusionsoft. Very quickly, in a matter of a week or so, we had seven committed to starting within a matter of fourteen days.”

Greg quickly started interviewing for someone to help him manage these new clients and build campaigns. And so, “before the business even officially started serving clients,” his first team member, Lisa came on board.

Greg’s aim in hiring Lisa “was to get someone who would help take as much off of my plate as possible. Since I was really service based, that was someone who could do the work in the fulfillment and the delivery.”

Lisa’s focus was managing a handful of client accounts and “helping remove me from as much of the fulfillment and delivery as possible so that I could keep focusing on sales,” says Greg. She started part time, but within two to three months had taken on enough work with Greg that she was able to leave her full-time job.

Greg’s next hire was a part-time executive assistant, Megan, who came on to “help protect me and my time around my calendar, my email inbox.” Megan’s role has since evolved to become a community manager and client concierge.

Lisa’s role has evolved too, as she’s become the company’s operations manager.

Although Greg certainly doesn’t regret his hiring decisions, he says, “If I were to be doing it again with our current model, which is more group consulting, group coaching, and training, an executive assistant would almost definitely be my first hire.” Says Greg, “Having an executive assistant really helped protect my time and do a lot of the ‘lower-value’ tasks. By having them taking those off my plate, I inherently increased my own hourly rate and could start working on higher-income-producing activities.”

Finally, Greg has advice for other entrepreneurs who are eager to make their first hire. “I did interview a lot of people. It was very scary, but, speak to enough people and make sure they’re a good fit for your personality and your values. Be patient with them coming onboard.”

Racheal Cook

“You don’t have to start with a huge team. You can start with the area that is the bottleneck for you and just five hours a week and grow from there.”

When Racheal launched her business over ten years ago, she “started with a virtual assistant pretty much immediately.” Racheal knew she needed to stay focused on revenue-generating activities—namely her consulting and coaching clients, so she hired this VA to help out just five hours a week with admin, email, invoices—“all of those little nitty-gritty details that go into the day-to-day of running a business.”

This “freed so much bandwidth” for Racheal, who credits hiring a VA early on “as a big reason why I’ve been able to grow my business working just twenty-five hours a week.” As a result, she oftens recommends her own clients “get some support as quickly as they can in the area that is the biggest bottleneck for them.”

By three or four years in, she had also hired an online business manager to take over the behind-the-scenes operations and team management. This person, Amber, “has taken over the entire operations path of my business… she’s really the person between me and everyone else who we need to be in contact with to run the team,” says Racheal.

Having Amber on board has allowed Racheal to “stay in my zone of genius . . . working with my existing clients, creating new content, new products, programs, and services.”

“She’s my number two all the way. I trust her with my life.”

With Amber’s help, Racheal has “grown this business to multiple six figures on the way to a million dollars of revenue a year.”

Now, ten years later, she’s running that multiple six-figure business with “a very small, but very amazing team.” In fact, most of her team has been with her for going on six or seven years now.

About five years ago, Racheal was also able to retire her husband, Jameson, and bring him onto the team part-time. (The rest of his time is as a stay-at-home dad.) As a former English teacher, Jameson has played an integral role in content creation and strategy for the business, planning out content and producing both a weekly Facebook Live Show and a podcast called Uncomplicate Your Business.

“We now are able to literally look at each other across a desk while we are working about twenty-five hours a week so that we can enjoy the rest of the time with our family.”

Laura Roeder

“I knew there were people out there who would love to do it and could do a much better job than I would do.”

Unlike many entrepreneurs who hire their first employee to help with administrative tasks like email inbox management, Laura, the CEO of social media startup Meet Edgar, started building her team by filling two slightly different needs: bookkeeping and customer service.

When it comes to bookkeeping, Laura says, “You can’t mess around with doing that yourself. It’s too complicated. Almost everybody needs to outsource that. So, I always, always had a bookkeeper from my very first freelance business.”

“And I think that applies to a lot of entrepreneurs out there,” she says.

Her decision to hire a customer service specialist, meanwhile, grew out of her realization that customer service “was not a strength of mine. I would get really frustrated answering customer service emails and I knew there were people out there that would love to do it and could do a much better job than I would do.”

Grant Baldwin

The Speaker Lab

“Think through what are the things that only you can do, and then the other things that you could potentially have someone else do.”

Grant made his first hire a few years ago, when he was a full-time speaker. His gig load had grown from twenty or thirty to as many as seventy gigs a year, and the logistical requirements began to pile up. So the first person he hired was an administrative assistant who could help him with all the “moving pieces that go into being a speaker and all of the things that go on in the back side of the business in terms of contracts, and travel, and logistics, and details, and all of that stuff.”

He paid his new assistant per event, “so when I was busy, she was busy. When I got paid, she got paid.” Grant says this helped not just in terms of cash flow, but also “to eliminate a lot of the stress and worry of different things that I was trying to deal with so I could focus on the thing that only I could do, which was to be a speaker.”

Whenever Grant would book a gig, he’d “pass the baton to her. I would tell the client that, hey, here’s your new contact. Here’s who you’re going to be working with, and she’s going to take care of everything from there.”

She handled all the contracts, deposits, invoices, travel, and anything else the client needed, which freed up Grant to do what he did best: “My job was to book the gig and to show up and speak, and she handled everything before and after and even during the process.”

Then, after starting his podcast, the Speaker Lab, Grant hired someone else to help out “with the tech side of things,” getting all of his software tools “to play together nicely, and to make sure everything was loaded up correctly for email blasts or email responders that were going out.”

These first two hires “made a huge, huge difference” by allowing Grant to “focus on the things that only I could do.”

Grant’s advice to other entrepreneurs is straightforward: “For anybody considering making their first hire, think through what are the things that only you can do, and then the other things that you could potentially have someone else do.”

Shannon Irvine

“As my business grew, as my vision grew, as I started to really want to see it go a different level, then I started to bring personality tests into it and really hire for aptitude and passion.”

Shannon started to build a team about a year after launching her business. She noticed she was spending her time doing what she now calls the “less than 5 percent activities”—things like responding to emails and building Facebook ads.

At this point, she says, “As I started to focus on my vision and where I wanted to take the business and how I wanted to impact others and transform others’ lives, it really became important to me to start focusing on those top 5 percent activities that really would get my business to the level of my vision.”

She started by going to sites like Upwork and to find technical help for one-off projects and tasks.

When she found hires that excelled at their task, she’d keep those people on. Gradually, she started to think about how she could build an actual team of people who were in it for the long haul. Says Shannon, “As my business grew, as my vision grew, as I started to really want to see it go a different level.”

That’s when she “started to bring personality tests into it and really hire for aptitude and passion.” She made a decision to focus on cultural fit over hard skills, and to “allow somebody who may not have the exact skill but would really be the right team member fit to be who we hired.”

And “the biggest and best thing” she’s done to bring her vision to reality happened about a year and a half into starting her business, when she hired an “integrator.” Her integrator helps her manage her ideas and set goals based on a ninety-day period. Whenever Shannon comes up with a great idea, her integrator will tell her, “Okay, let’s put that in the vault” for consideration in the next ninety-day stretch. Shannon believes that doing this “keeps me focused on what’s going to really move the business forward.”

But the “number one thing about bringing on a team,” according to Shannon? “I wish I’d done it sooner.”

Christina Nicholson

Media Maven

“It is such a weight off my shoulders to have another person there to help me take care of things and execute work successfully for my clients.”

Christina started building her team about six months after starting her business. She had a large and diverse client load, and the work necessary to keep all of her clients was getting to be too much, so she brought on an extra publicist to help her pitch a potential new client.

She found this publicist in a Facebook group composed of other people in the media industry. It just so happened that this person was local to Christina, which she says was “very helpful.” “It was a good fit,” says Christina, and a few years later, the publicist is still on Christina’s team and helping out with client work.

After bringing her on, Christina realized how valuable it was to have some help in her business. “I quickly decided that I will never do any of the servicing for my clients by myself.” Christina still oversees a lot of the client work, but estimates that 80 to 90 percent is carried out by people on her team, which Christina says “is wonderful because it frees up some time for me to focus on, a) what I’m best at and, b) what I like doing.”

Christina’s team has grown since then, but all of its members are independent contractors. “I don’t have any employees, and I don’t want any employees. I think that’s just more work and a bigger headache than what I want to get into right now.”

Employees or not, Christina says the benefits of having a team are huge: “No matter how much bigger my business gets, or even if I lose everything and I go down to just one client, I would still have help because it is such a weight off my shoulders to have another person there to help me take care of things and execute work successfully for my clients.”

These entrepreneurs chose not to go it alone, and it’s been paying off for them. Hopefully their examples will give you some ideas and inspiration for how you can tap into the immense talent that’s out there waiting to help you take your business to the next level!


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