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Sometimes, having a business partner is a pain, but once you’ve learned how to complement each other’s strengths and weaknesses, it becomes the perfect formula for growth. Our guest today is Connor Gillivan, the Co-Founder and Chief Marketing Officer of FreeeUp. As an eCommerce expert and outsourcing guru, Connor is passionate about building profitable businesses that address specific customer needs within the eCommerce world. He talks about his entrepreneurial journey with his business partner, Nathan Hirsch, which started back in college. Connor emphasizes the importance of communication, timing, and continuing education to build a successful business.
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Connor Gillivan is the CMO of FreeeUp.com. As an eCommerce expert and an outsourcing guru, Connor is passionate about building profitable businesses that address specific customer needs within the eCommerce world. He started out in his college dorm room and went on to sell over $30 million online. Having worked with over 1,000 suppliers and managed over 500,000 products, he’s now a published author and the owner of ConnorGillivan.com. He lives in Denver, Colorado. Connor, welcome to the show.
Thanks for having me.
You’re welcome. Why don’t you walk me through what you are doing? How it all worked so everybody could understand and then we’ll get to the story of how you’ve scaled it.
FreeeUp is a competitor to other freelance marketplaces out there like Upwork, Fiverr and Freelancer, but we do things a little bit differently. We spent years hiring from platforms like those and we wanted to create a simpler way for both business owners and freelancers. The core things that make FreeeUp different in connecting freelancers and business owners are first, we pre-vet every single freelancer that wants to join the FreeeUp network. We only allow the top 1% in and then those freelancers are able to make their services available to businesses through the platform. The other key difference is once you post a job through FreeeUp, you only get introduced to one qualified applicant at a time, whereas in some of the other platforms you may receive twenty-plus people. You’re then spending time interviewing and vetting them yourself. We try to cut that time down and make it an opportunity for a quick hire. On the back end, we’re very customer service-focused. If you ever run into any billing issues, if you have a freelancer that has to quit, we’ll replace them immediately and cover replacement costs. We’re always there to provide you with that hands-on experience when you’re hiring and also when you’re building your freelance business.
Are the freelancers global or US-based? Are they everywhere?
It is a global platform. We have about 2,000 freelancers on the network. About 40% are from the US, 40% are over in the Philippines, and then the remaining 20% are scattered across about 30 other countries.
Are there any industries or verticals that you focus on? Are they heavy in the tech sector or heavy in the admin? Where do they focus?
When we started the business, the first year was focused on catering to people that were selling products on Amazon. That was because that’s where our background was. My business partner and I, we ran a company before this one selling products on Amazon for a few years. We catered to them at first, but over the past few years, since we have the business, we’ve expanded to a lot of eCommerce disciplines and then a lot of marketing and advertising as well.
Do you still have a fairly good depth of the strength of your freelancers in the Amazon experience side as well?
That continues to be one of our top disciplines that we placed freelancers with businesses for.
Do you fill in the gaps between hires? If somebody is let go or someone is quitting, is that a good use of your model or is it more supplementing?
Both, we definitely have people that come in and they’ll use us to have an intermediary between hires if they’re doing full-time in-house. They could come to us and find someone who could fill that role while they’re doing other recruiting and interviewing. A lot of our clients will use it for supplementing. They may have an office and have employees in-house, but then they want to give each of those employees an assistant or they don’t want to hire in-house full-time for someone that’s creating content. They’ll come to us and get someone to manage that. There are a lot of different ways that they utilize it, but it does cover those two ways you mentioned as well.
When did you start? How long ago?
It was about mid-2015 when we started FreeeUp.
Has the growth been easy? Has it been challenging?
Growing any business is always challenging, but I think the timing and the space that we’re in has helped a lot. The whole freelance industry is booming and it has been since we started. We’ve definitely had that on our side and we’ve seen great growth because of the focus that we’ve had in terms of the customers we’re going after and the types of services that we’re offering through the freelancers. That’s been great in terms of the timing.
How do you make your money?
We were similar to a lot of the other platforms. Freelancers set their own rates at hourly or fixed rates. We even add a 15% fee from our end. The end fee is what the client pays to us and then we pay the freelancer as well.
Does the 15% cover your ability to screen and vet them?
Yes, correct.
Are they vetting you by doing work on your business for you? Is that part of your interviewing process?
It’s not, but when we started the business, we only started with people that we had worked with to start with. Now it’s a four-stage application interview, testing and onboarding process that every freelancer has to go through.
What kind of recruiting, interviewing process or platform do you use for that? Do you do something in-house?
It’s in-house. We custom-built it into our software that also manages the clients’ and the freelancers’ relationships as well.
You’re the CMO and you’re the Cofounder of the company. Who’s the CEO or who is your Cofounder?
The CEO is Nathan Hirsch.
Complementing Your Business Partner: Growing any business is always challenging, but timing and space will help a lot.
How did you and Nathan connect?
We’ve known each other for many years and we’ve been building businesses together for that entire time as well. We met in college in Connecticut. We were in some similar business classes together. He was starting to buy and sell books on Amazon. I was always looking for something to do that was entrepreneurial and he was looking for someone to team up with on it. That’s how it all started. We started with that first business and ran it. We got to know each other. We became good friends and realized that we complemented each other pretty well when it came to running a business.
Were you running businesses while you were in college then?
Yeah, we started that first one. We were both sophomores. We ran the business for a couple of years while we were in college.
Do you think you learned more about running the business than you did in class?
That’s 100%, for sure.
What did you take in school?
I was an econ and math major. It was a lot of business and a lot of numbers and data.
I was talking to my girlfriend about it, that I definitely learned more in college running my painting business than I ever did in classes. I wish I’d paid more attention in my classes now because I could have maybe pulled some of that information back in a little bit. You and Nathan got involved in this. How did the idea start? What was that discussion like?
We were running this Amazon business where we are working with suppliers and brands around the United States. We are pretty much their partner to help them sell their products on Amazon. This was 2009 to 2015 when a lot of brands and manufacturers didn’t know much about the online space. They were starting to learn about Amazon and they didn’t have anyone in-house that could help them sell. We partnered up with them. We built the business into a good size. We had an office and some full-time employees, but then we learned about this whole world of outsourcing and the ability to hire people at lower wages in different areas of the world that could potentially supplement what we’re doing with the business, lower our overall costs and keep growing at a good rate.
We started using Upwork, Fiverr, Freelancer to post jobs, interview and find candidates. We found some amazing people. That turned us on to this whole idea of outsourcing. We ran into a lot of frustrations. We were spending a lot of time doing the interviews. We were running into a lot of turnovers and we didn’t have any customer support from those platforms since they were already big enough to be solely focused on the software experience and not necessarily on more of hands-on experience. In 2015, after running the Amazon business for a few years and coming to a conclusion that there was always going to be a little bit of a ceiling with selling on Amazon because of how large Amazon is and how much control they have over their sellers. We started to think, “What other business ideas could we have?†That’s when we came up with the idea for FreeeUp and we tossed it around for a few months and tried to understand what it could look like. We brought it to the market and tested the idea out and saw what customers thought about it.
How did you fund it?
We funded it by ourselves. We started at about $5,000 and bootstrapped it all the way to where it is now.
You’re still self-funded then.
Yes, correct.
How many employees do you have now?
Our entire team is about 35 people. All of them are contractors. We run the business 100% remote. I’m in Denver, Nate is in Orlando. We have a team of specialists around the US and then a good amount of people in the Philippines as well.
How did you and Nate divide up the roles then? How did you decide who is running which parts of the org chart?
When we started, we knew we wanted Nate to be the CEO. He’s great at that role and commanding things and making sure the strategy and goals are being met within the team and within the growth. I’m definitely more on the side of content marketing, data analytics and software development. We initially divided it like that. Over the years, we’ve slowly built out our own roles. We have Nate as the face of the company. He’s the one doing a lot of the public appearances, podcast interviews, Facebook Lives, whatever it may be. Those things that are helping us get out there and get the company known. He’s also working with the actual experience. He’s talking to clients, he’s doing sales calls and he’s working with the freelancers on the actual experience. On my side, I’m handling all of the content marketing. I’m working with our development team to make our software better on an ongoing basis. I’m also handling all of our partnerships to keep them organized and ongoing.
Clearly, you’re in different time zones, different parts of the US. How do you stay in sync with each other?
We do a few things. We are on Skype, each of us about twelve hours a day. We’re always communicating and staying in touch with each other. We have weekly calls where we go over strategy and talk about our goals for the week, the month, the quarter so that we’re on the same page. Every quarter we meet up once in-person to plan out the next quarter and review the past quarter. That first meeting of each year is where we plan out the year as well. We have some touchpoints where we’re physically together. We communicate on a regular basis through online as well.
Talk to us about running the remote team in the Philippines. How has that been working? What lessons have you learned in running teams over there? You’re literally on the other side of the world. It’s a twelve-hour time difference.
We’ve been working with people in the Philippines for a few years now. It was definitely a learning curve at first, understanding their culture, understanding how they work with people. We learned they’re pretty shy. A lot of them aren’t going to speak out. They’re very polite. They have a very customer service-driven culture, so that helps. Business process outsourcing is one of their biggest industries over there. A lot of the people that end up in freelancing have worked with American, Canadian, European companies in the past, which helps a lot. We’ve become very strict on who we work with too. We have criteria internally of who we look for. We do look for people that are more entrepreneurial, that is a little bit outside of that normal Filipino culture, and that are ambitious and want to help us grow the company.
Were they working from an office over there as well or are they working remotely?
They’re all working from home as well.
You’ve gone upmarket in that market then as well. The Filipino culture is amazing and the people are completely loyal and they’re almost honored to work with American companies or Canadian companies as well. It’s a big pride of theirs to be able to have landed that job and the loyalty is amazing. I remember I had an EA for a few months from the Philippines. One morning I woke up, she’d sent a video of her playing guitar and she’d written a song for me that she’d sung. It was like a birthday message. I’m like, “This is crazy and partially creepy as well,†but it was neat. She was honored to work with me, which is cool. What about technology and working with your group that is scattered throughout the US? You are 100% remote company, right?
Complementing Your Business Partner: Thinking more in a quarterly term gives you goals to be working towards on a daily basis.
Yeah, correct. We have a CTO who’s been with us since the beginning. He’s up in Seattle now. We have two full-time developers in India and a guy in the Philippines. All that communication is done through Skype and online channels. The way I do it as I project manage that team. I work very closely with our CTO to understand what our high priority projects are so he and I can work very closely on them. Our team, we divvy out work to them on usually a two-week sprint basis. We’ll say, “This is what we’re focused on for the next two weeks. Let’s go ahead and make progress there. Keep us updated on a daily basis.†We go ahead and push to make things live at the end of each two weeks. As bugs and things come along, they’re communicated to us from the assistants and the internal team and we handle them as they come in. We have systems and processes in place that allow us to communicate and keep everything very organized.
How about with your operations, marketing and salespeople? Are they working on those same two-week sprints as well?
Less on two-week sprints, more on weekly meetups and figuring out goals for each other. With my content team, my advertising team and a few others that I’m responsible for, I’ll have weekly or every other week meetings where we go over core goals and we set the trajectory for what’s happening next. We check in with each other every day online as well. There’s constant communication going on at all times.
I love to learn from you on the recruiting and interviewing side, especially as you’ve taken those recruiting and interviewing systems and put them in place to screen 2,000 and freelancers. What’s working for you on the interviewing and recruiting side with them? What have you thrown out that you tried that didn’t work or used to work but no longer works?
For the things we’ve thrown out, we used to do either phone or video interviews. We have stopped doing those. We do chat interviews for every freelancer that applies and make it to the interview stage. The reason for that is that’s one of the most common ways that freelancers are communicating with clients once they’re on the platform and working with them. For us, we want to make sure that they have good written English, they communicate quickly and they show up on time for those types of meetings. That’s something that we moved away from and something we found to be effective in the interview process.
When it comes to overall vetting, the three key areas we look for are their skills. We look for people that have at least one to two years of experience in freelance working in the skill set that they say they have. We look for their attitude. We like freelancers that view their freelancing as a legit business and they do it full-time. They’re trying to grow it. They may be working towards eventually owning their own freelance agency as well. To us, that shows they’re more serious about it and they’re not going to be flaky with clients and they want to take it seriously. The third is communication. That’s the biggest thing with working with anyone remotely. Are they showing up on time? Do they have good standards for daily check-ins? Are they sending updates as it makes sense through email and things along those lines? Those are the three things we focus on. We ask a lot of questions around those topics as well.
I love that you’re doing the chat interviews as well. I used to hire a bunch of people in PR and for me, public relations was an outbound sales role where they phoned the journalists. They never emailed anyone, so they picked up the phone. I decided to only interview people over the phone. I didn’t want to see their face because I didn’t care what they looked like. I wanted to hear what they sounded like and how they could work. I had them send me some basic follow-up stuff from our call on email to see if they could be succinct and get the point across and if they could spell it. I didn’t want them to be a journalist, but I wanted to know that their grammar was reasonable and they could maybe drop an emoticon in there. In growing this business, has it had to pivot at all or have you been on strategy for the few years since you started? Has it stayed consistent with what you thought?
There was some pivoting in the first year for sure. When we started the company, it wasn’t a 100% freelance marketplace. We were offering eCommerce consulting as well as a course on how to sell on Amazon. We threw the three things out there for the first year to see what bites we could get and see what people were most interested in. Once we saw that a majority of the people, no matter which channel they came through, they were most interested in hiring pre-vetted freelancers. In year two, we said, “Let’s drop the others. Let’s switch totally over to this and make our focus this.†Since then it has been pretty consistent. It’s always a balance because with the marketplace, you have your demand from clients and then your supply of freelancers. If you get too outbalanced on either side, someone gets angry with you. You’re always trying to keep that in balance and make sure that when there’s more demand, you have more freelancers coming in, etc. That’s been consistent and we’ve tried to stay in our lane. We focus on the Amazon, the eCommerce, the marketing people and we try to keep that niche very focused.
It’s interesting you talk about the supply and demand and the balance in that. I’m laughing because Uber finally went public, but it was in the summer of 2008 or 2009, I told Garrett Camp who was the Founder of Uber, that it was a stupid idea because I could never understand how they would ever get that balance in place. I was trying to explain the whole ride-hailing thing. We thought it was stupid that people would ever want to get into a stranger’s car. I dismissed it as a dumb idea and now I’m like, “That was a dumb idea not to invest in that one.†You and Nate are working remotely and staying in sync. You have your meetings, your quarterlies, your weeklies, your monthlies. Did you have any conflicts over the years and how have you worked through those? Conflicts are normal.
A big conflict we went through on when we were starting to work together and figuring out each other’s work styles was I was much more of a long-term thinker. He’s much more of a short-term thinker. At first, we very much clashed. I was always “Let’s plan out the next few months.†He was, “Let’s get something done tomorrow.†There were a lot of arguments around that at first. Over time we respect each other a lot. We understand each other’s opinions and see where each other come from. Over time it’s benefited both of us because he now thinks more in a quarterly term. I like that because it gives us those goals to be working towards on a daily basis, but it spreads it out a little bit. I’m much more grounded to what’s going on in that quarter and then on a weekly basis as well and less concerned with a few years down the line. There were a lot of arguments there at first, but it’s happened for the best for both of us.
How about in terms of growth? Where have you had grown the most over the last few years in terms of being a COO, second-in-command and building this startup to where you are now?
My biggest area of growth has been digital marketing in general. I did not have any experience coming into starting this business with digital marketing. With our first business, it was know everything about Amazon and know how to help people sell their products there. We never had to do the selling of products outside of Amazon. Amazon takes care of all your marketing. When we started the business, I had to learn about SEO and content marketing. I had to understand how you’d set up partnerships with companies and what different referral programs look like and what advertising looks like as well. That’s been a huge learning curve for me but I personally love learning new things. I take it as a challenge and throw things at the wall, stick with ones that work and toss away the ones that don’t.
How did you learn? Where did you go? What did you devour? Was it courses, masterminds, videos? What did you do?
It was a lot of books and blogs. I found some influencers in the marketing space that we’re creating updated and modern content about all the topics. I devoured all of their information, listened to their videos, listened to their podcasts. I found direct books that were related to growth marketing, digital marketing and examples from what other companies had done in the past as well. I took all that information and then ran a lot of tests internally.
Are there any specific resources that you’d recommend?
I like Neil Patel. I love his contents. It’s very in-depth when it comes to digital marketing SEO. He also has a podcast called Marketing School. That’s a great one if you’re looking to learn about that stuff. Those would be my two biggest that influenced me the most.
What have you stopped doing in terms of marketing? What was working that’s no longer working or what have you changed there?
At first, were doing a lot of advertising to start, but we didn’t see a lot of great results from it. We cut back on that a lot. We still do it to a certain extent for branding and awareness. We decided to pull away from the budget from there.
Where are you getting most of your customers from now?
Most of our customers come from referrals and word of mouth? We have a great referral program where we paid out over $250,000 worth in referral earnings for people sending clients to us. We get about 25% of our customers through Google search and other search engines. We have a lot of partnerships with influencers and other companies in the space that we do a lot of content marketing with. Through those efforts, they come through to us as well.
Are those all the areas that you run in the business?
That’s correct.
Those are huge. What’s coming now in the business? What challenges are you working through?
A big challenge of ours has always been our software experience. Since Nate nor I are experts in that area, we’re always relying on our CTO to pick up the slack there. He’s more of a developer, less of a designer. We launched a new design for all freelancers and clients. They were happy about it. It makes it a little bit more modern and makes it easier to use on mobile. We’re also introducing the ability to add fixed price rates through the software. That was something that we were doing manually before. Another idea that we’re working through is the idea of pre-vetting agencies and allowing them to offer their services through the platform to businesses. We’re trying to gather feedback around it and see if it’s a viable option, and if agencies and businesses would be interested in it.
It’s an interesting model because there are many agencies out there and it’s been tough to evaluate them all against each other. We almost need to start seeing the leveling of that because a lot of people have wasted a lot of time and money with agencies that they wouldn’t have gone with had they known more.
That’s the idea. We’re testing it out and seeing how it goes. We’re trying to keep it very specific. We’re looking for boutique agencies. People with five to fifteen people max. Their founders are still involved in the daily processes and working with clients. They take their customer service seriously and they have a proven track record with other clients.
Complementing Your Business Partner: Instead of doing it alone, get a business partner.
Do you get together at all to start planning out any of your annuals or your quarterlies? Do you and Nate get together? Do the management team get together or do you still do all of that remotely?
We do. Nate and I get together in person about once per quarter. We’ll plan out the next quarter and then we disseminate that to all the team, but we don’t have meetings where we get the whole team together in person.
How do you deal with building a culture when you’re remote? I coached a company called Acceleration Partners. They’ve got about 150 employees in the affiliate marketing space. I think they’re the number twelve company to work for on Glassdoor. They don’t have anyone in a single office. They’ve cracked the code. I’m wondering what you are doing to crack that?
It starts with Nate and me and the way we run the business and the values that we live by. We value hard work. We value people who are entrepreneurial and share their voice and give us real feedback. We value people that want to stay with us for the long run, take this as a piece of their own and want to run with it. We regularly make examples of those as we’re working with people. In our interview process, a lot of our questions for people internally are around those values. We try to find people that are of the same mold as us but then come with different skillsets that they can offer to the business. The last thing is communication is everything for us in our culture. If we hire someone and the communication is not there, we’re quick to let them go because it’s such a huge part of running the company. We can’t have people that aren’t good communicators.
You mentioned that you and Nate use Skype a lot. Are you using Skype with all of your clients and your freelancers as much as possible after you’ve hired them or are you still doing a lot of that written?
We use Skype and we use chat for mostly everything. We’ll have calls sometimes, but mainly it’s group chats or individual chats.
What are you working on training your team? I’ve always believed that a leader’s job is to grow people. How are you growing your management team or your frontline staff? How are you working on growing their skillset?
Nate and I, we meet weekly with the leaders of the different teams of the company. There are about five of them. They oversee the main areas of the business and operations. We meet with them on a weekly basis. We keep them on track with the core goals that they’re working towards. We also have one-on-one quarterly meetings with each of them to go through feedback on how they can continue to grow. We provide them with resources that we think will be useful in helping them to be better leaders and managers. We keep pushing them. We were always there as a resource to answer questions they have. We’re always trying to give them honest feedback that will help them to grow as well.
How does that honest feedback work? Give me an example of what you mean by honest feedback.
In a quarterly meeting, we make sure we ask for their feedback and understand what they think of the business and how things are going and give them that opportunity to share things that they may not have in a group setting in the past. We challenge them. An example may be one of our team leaders is definitely less confrontational when it comes to managing the direct assistants that she works with. If something happens, she may not get on top of them immediately and say, “This was done incorrectly. We need to correct it in this way.†She may wait sometime before letting us know, then that halts us from being able to go and talk to that person. Direct feedback around where there are these small things that you probably have to get over mentally to be able to handle more responsibility. We try to give that honest feedback so they can take that and challenge themselves to be better.
You mentioned that you’re also pretty quick to get rid of people if they’re not good on the communication side of the business. What systems do you have in place for firing people?
We’re quick to fire, but we also give warnings. It’s usually a two-warning type of deal where if they made a mistake, we give them honest feedback. We give them constructive criticism on how they could improve there. We give them a week or two weeks to see if improvements are made. If more things come back and there are more strikes, we then decide to let them go from the business. At that point, we have a system process in place that removes them from all group chats and shuts down their email. It changes all of our internal passwords so that they don’t have access to anything anymore. We make sure that they’re completely let go from the business so that they can’t impact us negatively in any way going forward.
You mentioned passwords. What are the technology tools that you are using or any tech hacks that you have been using that have been helpful?
We use LastPass, which is an app that allows you to store passwords and once you change them, you can put them in there. You can share it with different people on the team so they have access to all of it or certain parts of it, etc.
What other software and apps are you using to run the business?
I use Trello pretty often for software, graphic design, content. It’s easy to be able to communicate with people and put projects in there and then have them comment or give me updates. Nate uses a bunch of apps for networking that he uses to reach out to people and get in touch. We also use Jira for our software development management as well.
How about any masterminds? Are you part of any mastermind groups at all that you’re growing with or involved in?
We are not as of right now. We partnered with some mastermind groups to be a resource for all of the entrepreneurs. Nate is going to Baby Bathwater Institute, which I believe is technically a mastermind. It’s a meetup. He’s going to that in Croatia. That will be the first one we’re attending.
He’ll love it. The client that I was coaching in Germany is going to be at the Baby Bathwater Croatia. I’ve been to three of their events. It will be great. He’ll love the community and great people. I’ve been in the Genius Network for a few years. I’ve been in Strategic Coach for a few. I went to five Mastermind Talks events, three Baby Bathwater events. I came back from one at War Room. There are some legit conferences and then we started one for Second In Command. It’s called the COO Alliance too that I’ll send for you. That could be interesting for you because it’s more operational. It’s people that think more like you. I’m glad Nate’s going to Croatia. That will be a fun one.
We were back and forth on whether we should send him, but he was finally like, “I want to do it.†We said, “Let’s go for it and see how it works out.â€
It’s a no-brainer. He’ll get ten times his investment in terms of the dollar value of what it costs him to go and to fly there and everything else. He’ll get ten times return just on business from it. The learning, the ideas, and everything else will be incremental. The network that you build of people that are doing what you do as well is powerful too.
It should be a great trip.
One final question. If you were to go back to your 21-year-old self, if you were to be talking to the 21-year-old Connor and say, “Here’s some advice that will help you in your career.†What do you wish you’d known at 21 that you now know to be true?
It just happened, but I wish I had known how important a business partner is. When I was younger, in my mind it was always, “I’m going to go start a business and I’m going to do it on my own because I don’t want to work for anyone. I don’t want to have to report to anyone.†What I’ve learned over the years of working with Nate is we add so much value to each other. I don’t think I could have grown as much as I have without having him by my side. Sometimes he’s a pain in the butt and annoys me, but for the most part, it’s been a great experience. If I were a 21-year-old, I’d want to know that and I’d want others to know that as well.
You have done a great job of complementing each other. It’s almost creating a bit of a yin and yang partnership, which is great. Connor Gillivan, the CMO and Second-In-Command for FreeeUp.com, thanks for sharing with us on the show.
Thank you so much for having me.
I appreciate it.
Important Links:
- FreeeUp.com
- ConnorGillivan.com
- Neil Patel
- Marketing School
- Acceleration Partners
- LastPass
- Trello
- Jira
- Baby Bathwater Institute
- COO Alliance
About Connor Gillivan
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