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Hiring a freelancer can give you a higher return on investment than even the best stocks. But it can also be an endless money pit, that gives you nothing in return.

The difference between the two?

Well, it all comes down to the freelancer you pick to hire. Despite having great success hiring freelancers, I’ve never peeled back the curtain and reveal how I pick the best freelancers each time.

That ends today. In this episode, you'll discover my exact step-by-step process for hiring rockstar freelancers each and every time I need one.

Listen now.

Show highlights include:

  • How hiring a freelancer “flips” the usual hiring process and helps you land a talented team member quicker (2:10)
  • The absolute worst site, in my experience, to look for and hire freelancers (and which one to pick instead) (4:37)
  • How to hire a rockstar freelancer each and every time you need one (7:05)
  • Why hiring a more expensive freelancer will actually save you more money than hiring the cheapest freelancer (7:40)
  • How turning the freelancer process completely upside down magnetizes the best freelancers to you (and how to do this) (9:28)
  • Worried about handing over your passwords to freelancers? Here’s how to completely minimize your risk when you do… (12:17)
  • The overlooked way to get a 50% return on your investment (16:52)
  • The single biggest mistake financial advisors make when hiring freelancers—and the dirt, simple way to avoid this mistake (20:40)

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Go to https://TheAdvisorCoach.com/webinar to register today.

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Discover how to get even better at marketing yourself with these resources:




Read Full Transcript

You're listening to “Financial Advisor Marketing”—the best show on the planet for financial advisors who want to get more clients, without all the stress. You're about to get the real scoop on everything from lead generation to closing the deal.

James is the founder of TheAdvisorCoach.com, where you can find an entire suite of products designed to help financial advisors grow their businesses more rapidly than ever before. Now, here is your host, James Pollard.

James: Welcome to another episode of the Financial Advisor Marketing podcast. This episode is going to be about hiring freelancers and it's something I haven't talked about much in the more than 240 episodes of the Financial Advisor Marketing podcast. Wow. Sometimes I feel like I need to pinch myself because 240 episodes is a lot. I didn't really think I would make it this far. I mean, I know I like podcasting and I had the Advisor Coach Podcast before this, and it was something that I did, but, wow, 240, hoo. [01:00.0]

Anyway, I decided to record this episode, because, quite frankly, it looks like people are interested in this topic, and if people are interested, then I am going to give them more of that topic. Back on June 29, I posted a screenshot on LinkedIn of a freelancer I hired and said the following: “I love hiring freelancers. It's so much easier and faster to get specialized help. I hired another one this morning. What questions do you have about finding/hiring freelancers?”

What I'm going to do is answer the questions I received either in the comments and messages or through email. In the process, I hope I will detail what I do, how I do it, and why I do it. And who knows, I might inspire you to, I don't know, hire a freelancer, I guess.

There are several reasons why I like hiring them. I've already mentioned that it's easier. It's faster. But I love freelance websites like Upwork, because I can go on at any time and have a huge pool of potential hires waiting for me. I don't have to post an application and wade through a bunch of people who blindly applied. I can go on Upwork, type in what I want, put in whatever filters I want, and begin sorting through those people. [02:05.5]

Plus, everyone on those sites is there because they want to work and they tell you what they're good at. When you're hiring people, sometimes people just want a job. They'll do whatever you tell them and try to learn on the job. Freelancers tell you upfront what they're good at doing. If I want to hire a videographer, I can type in videographer and only see people who have that listed on their profiles.

You also know how much you're paying up front, because freelancers will tell you their rates, too. Think about that. They tell you, “Hey, I'm good at this. I'm good at this. I'm good at this, and this is how much I charge.” How cool is that? On websites like Fiverr, you can see how much each gig will cost. On websites like Upwork, freelancers display their hourly wage, but you can also hire them on a per-project basis. Continuing with the video example, you could hire someone for $50 per hour or you could contact that person and work out a deal for something like $150 per video, so you can do per hour or you can do per project. Fiverr is just per project, I believe. I haven't really used Fiverr that much, and I’ll tell you why in a minute. [03:08.3]

Next, another reason why I love hiring freelancers is because a lot of these freelance sites will give you some sort of social proof, and that's always comforting. Upwork is nice because it will tell you how much a freelancer has earned and it will tell you how many jobs that Freelancer has completed.

If you're hiring someone and you have 10 choices, one of the ways you can decide is by looking to see who has the best track record. If someone only has seven jobs and another person has 17, and another person has 77, you can give more weight to the person when 77, if all other things are equal, and you'll begin to see what I'm talking about if you go on Upwork or these freelance sites and you look at the social proof on there. You'll get a good feel for this. [03:49.2]

I started hiring freelancers in the early-2010s and I can tell you that the freelancing economy has come a long, long way. A lot of highly-qualified people are available that weren't available when I first started hiring, and that is awesome. That means, if you have any fears about hiring unqualified people, relax. I'm going to talk a lot about Upwork because that's what I personally use the most, and one of the nice features of Upwork is that freelancers have the option to share their portfolios on their profiles. This is also true on Fiverr where freelancers can upload samples of their work.

This is really common with designers, because they want you to see the work they've designed so you consider hiring them. It's kind of hard to say, “Hey, I'm a designer.”

“Can I see your work?”
“Oh, no. No work here. Just hire me as a designer.”

In full disclosure, I have not had good experiences with the contractors on Fiverr. I have paid for maybe 15 or 20 gigs and haven't had much success. I think part of the problem is that the workers on Fiverr just want to get the work done as quickly as possible, so they rush. I think there's more demand, so they know that if they're crappy, then more people are just going to come in because they're taking advantage of Fiverr’s distribution channel. [04:59.5]

On Upwork, there's more of a-- I don't want to say a more strict rating system because Fiverr does have a rating system, but there's just something there where, in my experience, the work has just not been as good. I've had more success on Upwork because it has stronger filters, and I love that. It's easier to message the freelancers and talk with them before hiring them. You can see if they're online. You can chat with them pretty easily. There's the mobile app. There's the desktop version. I use both to talk with people, because I like to vet people before blindly assigning jobs to them.

Then with that said, other people have had the exact opposite experience. I've had people tell me they've had fantastic experiences with Fiverr and that Upwork has gone downhill over the last few years. I can only speak from my experience, though, so take everything I say with a grain of salt that it may not apply to you and it may not work for you. It may not have anything to do with your situation. Let me get into the questions and the comments I received, and you can make an informed decision about what you want to do. [05:57.3]

One adviser said, “I have entertained the thought of seeking freelance help for one-off admin projects. When we have looked, we've been overwhelmed by the possibilities. It would be nice to hear how you cut to the chase and find reputable, trustworthy help.”

My hiring process comes down to a few simple fundamentals and I feel like this will help a lot of people. I think long and hard about what I actually want someone to do. If I want someone to help me with video, I don't just look for someone who has video experience. I consider the intended purpose of the video.

Is this video going to be for a webinar that's 90 minutes long and is largely a presentation?
Is this video going to be a YouTube short that's only 30 seconds long and needs a strong hook with captions, where a presentation wouldn't necessarily need a super strong hook and it definitely wouldn't need captions, especially if it's live?
Is it going on the homepage of a website where it will need awesome editing and it'll need to hold attention, so you increase time on page, which increases your SEO ranking, indirectly, of course? And all this other stuff. [07:00.0]

Even though all of those things can technically be done with one video person who is a jack of all trades, the way to hire a rock star is to find the person who specifically does what you want. In this case, it would be admin stuff, so you're looking at specifically what you need to get done and look for someone who does specifically that.

With a video example, again, if I'm trying to edit a webinar, I can look for someone who has experience editing videos for webinars specifically, and if I can't find that, then I’ll look for someone who has experience with presentations or slideshow videos. I’ll look for someone who has experience doing something similar.

Once I know exactly what I'm hiring for, then I will filter. My very first filter is to hire people in the United States. I know it's trendy to hire people in the Philippines and all that, but I hire American and I don't apologize for it. Yes, it is more expensive, but it's actually a great business decision for me for one big reason. Communication is so much easier and so much faster. [07:59.0]

Let's say it's 12:00 noon on the East Coast of the United States. That means it's 12:00 midnight in the Philippines. They are on the other side of the world, literally, 12 hours. If I hired someone in the Philippines, we would be on completely different schedules, and I don't want to deal with that. The same is true with India and other places in Asia, Singapore, even in the UK and in Ireland. I don't want to deal with the time differences.

It's so much easier to be able to message someone who is working the same hours as you and that person can respond to your messages within a reasonable timeframe. I guess if you hired someone in the Philippines who woke up 12 hours later or earlier than you and then went to bed 12 hours earlier or later than you, then you can kind of make it work if you're on opposite schedules and you just communicate that way, but that has not been my experience.

If I'm considering two people with similar qualifications to do a job and one is on the West Coast and the other is on the East Coast of the United States, I will lean toward the person on the East Coast, because when it's three o'clock in California, it's six here in Delaware. I don't want to deal with the messages at six, seven, or eight o'clock because I hired someone on the West Coast. [09:08.3]

Now, of course, this is all job specific, and, yes, I can set expectations in the beginning, but I'm speaking generally here. Don't take anything I say very specifically. I'm just speaking generally. Generally speaking, I would rather hire someone who is on the same schedule as I am because it's just so much easier to communicate. It's so much faster.

I also talk with them first. One big mistake I see people making on Upwork and other freelancing sites is they will create a job first and then invite a whole bunch of people to apply. I don't do that at all. I start with the people I want to hire and then create the job. I do it the complete opposite way that most people do, which, I mean if you think about it, most people get average results, and if you do what most people do, you'll get average results, so I'm doing something completely different. [09:55.2]

I'll record a video using a service like Loom or BombBomb, or something like that, explaining exactly what I want. I’ll show my face. I’ll share my screen so they know that I'm a real person. I'm sending the message specifically to them. I'll explain what I want in detail so they know exactly what to expect. Then I will let them sell me on why I should hire them if they're a good fit.
Once I find someone who is a good fit, I will create the job posting, and then invite that specific person only. Did you catch that? I am not creating a job and having 400 different people apply. That's insane to me. I know that's how it's done. I know that's how people do it all day long. But that is just absolutely bonkers to me. I look at the people. I talk to the people. I figure out who I want and I ask, “Hey, would you want to do this job?” If the person says yes, then I create the job posting and I send it directly to that person.

That is how I hire freelancers. I don't have to deal with a whole bunch of people who applied because they just want a job. I know exactly what I want. I find the people who can do it and then I make sure they're open to being hired. Then and only then do I create the application. My process is completely the reverse of the people who create applications first and then hire, which is probably why I get better results. [11:13.2]

Next question: “What types of things are you outsourcing?” I am primarily outsourcing admin stuff. I also outsource oddball editing jobs and coding, and things like that. I think graphic design is a great thing for a freelancer to do. If you do a lot of social media posts or stuff like that, it might be worth it for you to have a graphic designer. You pay a flat rate in order to create images for you, maybe $20 or something per social media image, I don't know. But then you can go back to your post that did well and tell him or her to model those images and you can just get better and better over time. Your social media approach, the entire thing, will get better over time.

Bookkeeping is another thing I think people could benefit from outsourcing to a freelancer. I personally don't do it because I have some ways to get my bookkeeping time down, 15 to 20 minutes per month, and I like to review everything myself. However, if you have a ton of transactions and you’ve found that it's a time suck for you, absolutely, hire someone to do bookkeeping. [12:09.5]

Oh, and a side note, this is really important so listen up. Hey, listen, if you're at the gym, stop. If you're driving, really pay attention, pull on the side of the road or whatever. When you're hiring someone to go into software, like your calendar or your webinar software, or any software you use, right, make sure you use a password manager. Please, please, please, do not give these people your passwords. Make sure they have the same password manager you use and then share it with them where it's protected. That way they don't see your password and you can revoke access at any time.

If you wake up some random Thursday morning and you're like, You know what? This relationship isn't working out. I don't want this person to be in my inbox anymore, boom, revoke access, and that person never sees your password. Okay? Use a password manager, please. Pinky promise you'll do this for me. [12:59.7]

Hey, financial advisors. If you'd like even more help building your business, I invite you to subscribe to James' monthly paper-and-ink newsletter, “The James Pollard Inner Circle”. When you join today, you'll get more than $1,000 worth of bonuses, including exclusive interviews that aren't available anywhere else. Head on over to TheAdvisorCoach.com/coaching to learn more.

Next question: “How do you determine the hourly rate? For example, which tasks are worth $80 per hour? And the $80-per-hour figure comes because I'm paying the Freelancer I hired in that LinkedIn post $80 per hour.

Now, there is no way for me to succinctly give a satisfying answer for determining the hourly rate. A really long story short is that I view it as an investment and I consider my alternatives. For instance, let's say I happily invest into a portfolio of index funds that I expect to generate 8% or so over the long term. This is per year, 8% per year. [13:57.6]

Now, let's say I can hire someone to do something that could net me a 30% rate of return. If I have a 50% chance of getting that rate of return, my real expected return is 15%. If I were to invest that money anyway, it's smart for me to invest it in hiring someone. That's a really summarized version. There's a lot that goes into it, and I know that, theoretically, the return could be -100% because you could get absolutely nothing back from your investment.

But here's the thing. When you're hiring someone, it is also a business decision, and in many cases, for financial advisors, it is replacing what they're already doing. I would never ever really be in a situation where there'll be a -100% return and you have to think about the probability of that even happening.

With the floor example, if you're just replacing yourself, you have to think, What is the probability that I'm going to get a 0% rate of return on this money? Then you're just going to stay the same. What is the probability that this person could be way more efficient than I am, and I see more things because I'm growing as a business owner and I can go back to that person and I can say, “Actually, I want you to focus on this,” and the whole business does better, like a rising tide lifts all boats, that sort of thing? [15:07.2]

So, you really have to think in terms of probability, but what I'm doing here is I'm thinking in terms of that and the expected return. I hope that makes sense. There is a lot that goes into it, but it is an investment.

As for tasks that are $80 per hour, pretty much all marketing manager jobs, marketing managers make about $130,000 or so per year on average. I know that $80 per hour is more than that, but I'm just giving you this example. I'm paying a premium for convenience, that's really what it is, on freelance sites, that you're paying for convenience, the ability to go directly to the sites and hire people, and to know with relative certainty that I'm hiring a rock star, since the people on the sites have the social proof. They have the reviews. Upwork tells you how many jobs they've completed. It tells you how much money they've earned. So, when I'm calculating my expected return, my probability is skewed up with a freelancer, because they have such strong proof. [16:02.4]

Now, I don't want you to think in terms of expensive or overcharging, or anything like that, because price is relative. It only matters when you compare it to something else. Let's say that you're currently putting $40,000 per year into a solo 401(k) and you would be thrilled with a 10% rate of return on that money. Okay, now let's say you could hire someone for $40,000 to do a single hour's worth of work for you. That's it, just one hour. Would you say that paying someone $40,000 per hour is outrageous? Are you overpaying? Is that overcharging?

LeBron James makes multiple thousands per minute when he's playing basketball. Is he overpaid? Is he underpaid? I don't know. And no matter what you think, it only matters when you compare the alternatives. How much money does he make for the NBA? How much merchandise does he sell? How much advertising does he indirectly sell?

Let's say you paid someone $40,000 for an hour of work and that work caused your business to make $60,000. That would be much better than the alternative. That would be a 50% rate of return when you would have been thrilled with a 10% rate of return. [17:10.7]

Most people will never be wealthy because they don't think like this. They don't think about the fungibility and the utility of money. They don't understand that their dollars can be invested in places like themselves and other human beings to generate a return.

Next question: “What is your exit strategy?” and the exit strategy is for the freelancers here obviously. My exit strategy depends on the task. Again, I don't hire people just to hire them. I will hire people with a specific job in mind that has measurable outcomes, and many jobs have a specific beginning and anyway, for example.

If you're hiring someone to create artwork for lead magnet, then the exit strategy is to part ways once that artwork is designed. If you're hiring someone to produce podcast episodes for you, then the exit strategy is to part ways once you no longer create podcast episodes. It seems so obvious, right? If the freelancers are terrible, fire them. If they're great, keep them. [18:04.1]

And I want to stress once more that you're making an investment. If the investment isn't working out for you, then you should not keep investing. That seems like common sense, but I guess it's not so common. If the Freelancer makes you money, keep him or her. If the Freelancer doesn't make you money, get rid of him or her.

Another question is “How do you measure the outcome?” Like I said, many of the tasks I hire for have clearly defined outcomes, because the only reason I'm hiring someone in the first place is to get an outcome. Back in the day, I had someone check my email for me. Her job was to get me to inbox zero every single day, no exceptions, and send me a collection of all the Inner Circle member questions once per day. That way, I can answer them all at once first thing in the morning. That is the outcome. If she didn't do that, she wouldn't work with me for very long. [18:51.4]

Think about when you hire people in your personal life. If you have a leaky faucet and you hire a plumber to fix it, the outcome is having a leak-free faucet. Either that gets achieved or you do not pay the plumber. You don't randomly hire a plumber to come into your home and look around. You only hire the plumber when there's a problem with a tangible outcome you want to achieve.

Or let's say that you have an unfinished room in your house and you want to finish it. You want to create and build instead of stop a problem. You're building something new where something didn't exist before it, kind of like you do in business where you're building marketing assets and things like that. The same thinking applies. You pay a contractor to finish the room for you and you track his or her progress over time.

If six weeks go by and the room still has no drywall, no paint, no electrical outlets or anything in it, then you wouldn't pay. It would be silly of you to say, “Aw, shucks, things happen. I'll keep paying you for another six weeks,” no, the right answer is “Wow, I should have checked in on you the very first week to see how you're benchmarking against these measurable outcomes. Now hit the roads so I can get another contractor.” [20:01.4]

I guess the real advice I'm trying to give you here is that I would avoid hiring for anything that doesn't have some sort of measurement associated with it. I wouldn't even get to the hiring part, and it's not merely because you want to play micromanager and breathe down people's throats. These measurements also gauge your success as a leader, because if your people aren't improving, then it means you aren't developing them enough. You are not helping them enough. A lot of the measurement isn't just for them. It's for you, too.

Okay, one more question and then I'm wrapping up the show. “What are the biggest mistakes people make when hiring freelancers?” That is a good question and I'm glad I'm ending on this one. I would say, the number one mistake is not vetting the freelancers. Take your time. Do research on what you want. Figure out exactly what you want the freelancer to do and then talk to a bunch of freelancers about that task. [20:55.2]

My wife recently started looking for an electrician on one of the big contractor lead gen websites where they take your information and send it out to 50 quadrillion people. She wanted someone to help with electrical work actually. Guess what? Apparently, everyone with a pulse in a 50-mile radius from our home is an electrician because she's getting bombarded with phone calls and emails from people who claim to do electrical work.

If she hired an electrician my way, she would have done the following. First, she would have figured out exactly what she needed done. Let's say we're getting a second electrical vehicle and we need another charging station in the garage. She would have looked for electricians who already talked about doing those sorts of jobs. Maybe they'd have pictures in their reviews or on the websites where they chose to show the little charging thing like the 14-50. Maybe they would mention it in their marketing materials. Maybe they would see it on the social media profiles.

When she saw that, she would reach out to them and ask them questions about how they could help her, not the other way around. I would never create a situation where a whole bunch of people reach out to me and try to sell me on why I should hire them, where they get the first contact because they're reaching out to me. I will create a situation where I reach out to only the people I deem qualified from the beginning. [22:13.8]

The number two mistake is being cheap. I think sometimes financial advisors will see, for example, freelancers who charge $50 per hour for something like admin work and have intrusive thoughts like, $50 per hour? I didn't even make that until Year 2 or Year 3, or whatever. They get in their heads and they start thinking about stuff that has absolutely nothing to do with what they're doing, which is making an investment.

I'm not hiring people to give them jobs. I'm not hiring to buy back my time. I do that in my personal life primarily, which Inner Circle members already know about. I do it to make more money. That's it. I'm taking a certain amount of money and giving it to a human being with a skill, because I have a reasonable belief that the human being skill can return more money to me. That's it. At the risk of sounding like a broken record, it is an investment. [23:06.0]

Let's say I have $100,000 in my business. I'm going to give you real numbers here. If I have $100,000 in my business and I invest it in a combination of good people and good marketing, it compounds at 30% per year and that's not difficult to achieve. If you know your business and you see the task that will lead to solid financial returns, it's absolutely not that difficult to achieve. If I invest that $100,000 at that rate of return, I will have more than $1.3 million after 10 years, even if I never invest in another dime. That's how you get to the million dollars with that investment.

People say, “Oh, that's a lot of money for you to start with.” You don't start with $100,000, necessarily. I mean, obviously, we have to go from zero to 100,000. Then you make your investment and you could do the numbers any way you want. You compound that over time. You can invest a little bit until you get to the 100k, whatever you want to do. If during that process, I invested an additional $50,000 per year, then I can reach $1.3 million by Year 6. [24:03.7]

I want financial advisors to be wealthy in all areas of life, including financially, which is why I stress the investing part so much, so really think about that. You can get to the seven-figure mark with just investing in other people in hiring. I mean, an additional $50,000 per year, I mean, that could be in a marketing campaign or several marketing campaigns. It could be in freelancers. Whatever, right? I'm just talking about the investment part of it, okay?

All right, that's enough. This podcast episode has gone on long enough. I hope this has helped someone. Thank you so much for listening. I appreciate you, and I will catch you next week.

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