How Freelancer Cory Jaccino Left the Safety of His Corporate Job to Triple His Income and Pay Off His Student Loans

Cory Jaccino is an Atlanta-based freelance Internet marketing consultant specializing in paid search engine marketing. In September 2011 he left the safety of his corporate job at InterContenintal Hotel Group (IHG) to freelance full-time.

His main motivations? Earn enough money to pay off his student loans in 3 years, diversify his income, and have more freedom and flexibility in his schedule.

I recently met Cory for lunch and I asked him a ton of questions about how he made the leap from employee to freelancer. I wanted to know how he had achieved freelance success so quickly and at such a young age. And I asked him about the prospecting methods that have generated his best and most profitable clients.

What follows is the transcript of our conversation. If you prefer to listen to the audio, you can download it here. (BTW, we recorded the interview right after the lunch rush, so you'll get to hear the kitchen staff prepping for dinner in the open kitchen. It added a bit of color to the interview. 😉

Download MP3

ED: Give us a quick summary of your solo business and specifically what you do, the types of clients you target and what services you provide.

CORY: I am an Internet marketing consultant and I specialize in paid search engine marketing. I usually focus on small and medium sized businesses, and I specialize in helping them grow their business online and expand their market share. Basically, I help them spend their advising dollars more efficiently and increase their conversion rates.

ED: I know you recently quit your day job, so this is kind of cool time to talk with you. Why don't you tell us a little bit about that journey ” where you were working, what kind of work you were doing and the challenges that you faced as you started making that transition.

CORY: I was working for a very large hotel company, IHG; it has seven different brands, Holiday Inn and Holiday Express. I was a senior analyst. I had worked my way up in a couple of different positions. But I really started out back in 2009 in the summer and I had a very large amount of student loans and really no way to pay that off quickly with the income I was making back then. So I was talking to a friend of mine who does SEO (search engine optimization) and he told me that I should really get into freelancing. I wasn't really sure about it at the time, but he told me just provide the same solutions that I was doing for these big businesses to small businesses. And he actually gave me a client and I did well with that client; I still have them today.

ED: And you did all of this on the side, so basically evenings, weekends, that sort of thing?

CORY: Oh yeah, I did the best job I could. I did this all on the side, at nights, on the weekends and I really just tried to help them any way I could to grow their business online. This initial client was a small company at the time, and they are still with me today. So I did that; I refined my processes and I applied those same ones to other clients who came along. So two years later, I had paid down a big chunk of that student loan debt.

ED: Using this new income source?

CORY: Yes, using the income that I had from the new clients. It was definitely a relief to have those clients because when you make that extra income, you don't have to worry about things the same way. You can really just focus on what's the most important thing you can do with your time, and I felt like that was refining the processes and doing a better job faster for each client so that I could take on more clients, which brought more income, which eventually allowed me pay down about $20,000 to $30,000 a year in student loan debt, which was great.

ED: Wow!

CORY: So basically I got into freelancing because of that student loan debt, and I knew I had to be the best I could be because I needed to pay it off.

ED: That was a big motivator. And it probably kept you from spending a lot of that extra money you are making. Because when you are making X and suddenly make 2X, it would be very tempting to increase your standard of living.

CORY: Yeah, I actually”when you say 2X, I actually went 3X.

ED: Wow!

CORY: So I actually had tripled my income within about two years, at the peak of it all. And I got to a point where I realized that I needed to go out on my own. I figured that if I can do this on the side while working a 40- to 50-hour-a-week job, then who knows what I could do on my own?

And I had really learned a lot at IHG. I had a great team that taught me a lot of different things about search engine marketing. But now I was working with these smaller freelance clients that would teach me different angles that I never would have appreciated or I never would have been exposed to had I not spent all this time with them. So I really got to be a much better search marketer by being exposed to different industries, different platforms and technologies and other people that were working with them, such as web designers and developers, for example.

CORY: So I was able to pay down a lot of my student loans and I was able to build up a little bit of a buffer to transition out of my day job, which I highly recommend, by the way. You just can't have a big enough buffer when you are transitioning. But you also have to really recognize when you should transfer. And when that opportunity presents itself, like it did for me, you'll just know what feels right.

ED: What was it for you? What was the moment, the event?

CORY: In September of 2011, I had somewhere around 20 to 25 client leads come in that month. And I just had to choose what was the best thing for me at the time. I had a lot of different opportunities. I had to actually find people to take over some of my current clients so that I could take on other clients.

ED: Wow!

CORY: I realized that creating value for everyone that you network with, being a good connector for other people, finding them work ” all those things really pay off because then they send people back to you. And when the time came to make my decision about leaving my day job, I thought back to what Steve Jobs said in his D5 conference with Bill Gates and Will Mossberg, "You can't really connect the dots going forward, you can only connect them going backwards."

So when you are in this kind of situation, presented with all those different possibilities, you have to figure out what's really right for you at that time. And I think you'll have a gut feeling about it. It's good to talk to a couple of other people and make sure you're making the right decision.

But I think it really comes down to building your circle of colleagues and brand advocates ” your connectors, people who believe in you and what you do. If you help those people succeed, they'll reciprocate. They will. Network wisely and just refine that intuition over time and just have a "help me help you" mentality. I think you'll just know when it's time. You'll really be itching to switch over and continue growing.

ED: Well, it sounds like financially, too, you were already prepared, so it was really more of a psychological issue at that point, right? It was more about getting over that mental hurdle of "Okay, is it the right time to make my move?"

CORY: Absolutely. And it can be a scary time because you are not really sure. You have this huge client that is your anchor and that really helps you pay your bills, so if you lose some of your side clients, you still have the big anchor. But if you really think about it, when you have a day job, all you have is one income, whether it's huge or not. So if that income leaves, if you get let go or if there is downsizing, layoffs or whatever, you could lose that "client" just as easily as you could lose a freelance client.

So I think spreading out your income sources and having several clients paying you a lot of money is probably a safer way to go, and that would be my advice. Find people who truly value what you have to offer because you provide valuable services for them, you help them make money or you do something that makes their life easier, more enjoyable, more profitable or whatever it they are paying you for. Just do the best job you can do, and I don't see why someone wouldn't want to keep you around if they can.

Worst case scenario, if they fall upon bad times and they have to let you go, then at least they are now a brand advocate of yours (if you've groomed them appropriately) and maybe they can provide you a lead or two so that you could go help someone else. So it all goes back to social proof and doing the best you can and providing that value no matter what.

ED: What have you done to really set yourself apart from competing paid-search firms and freelancers and to generate a steady stream of business in a difficult economy?

CORY: That's a good question. I tend to over deliver, especially in the beginning of a relationship ” just because I want to make sure the client is 100% satisfied. No matter what, you want the client to be very satisfied and want to hire you over and over and over again.

You never know when there is going to be more work, but even if it's a one-time deal, they may know other people, they may have other friends. Especially people who have made it already, they usually have their own circles of connections that they could refer you to or refer them to you. It's good to be honest and to build social proof and also to get experts and those higher-up people to acknowledge who you are, because they usually have many more connections that you do.

One of the things that I do to set myself apart is that I don't try to be everything to everyone. I try to just be the best I can be at paid search engine marketing. I don't do SEO; I actually have a guy I work with that does all my SEO. So if someone asks me for SEO services, I am honest. I say, "You know, I'd love to help you out, but I know someone that could do the work for the same amount of money and do a much better job. For PPC [pay-per-click], though, I could do a really good job for you.

And by doing that and by saying, essentially "I am not going to take your money and do a mediocre job with something that I am not really qualified for," you build trust and rapport. It helps you build that connection and reinforce that relationship. And it reinforces over and over again, "I do paid search, I do paid search, I do paid search." That way, when someone asks one of my clients or one of my colleagues if they know someone who does paid search, they immediately think of me.

It's a very simple and clear message and I am getting people of high stature to vouch for me. And I do this in a very genuine way because I'm contributing to them. I'll invite them to coffee, I have a genuine interest in knowing how they got to be as successful as they are. And often I'll try to provide something. I'll offer them valuable ideas and information. I'll offer to help them out with something and without any expectations.

ED: So it's not a "gimmicky" approach. When you try to connect with them, you listen to what they are saying and you try to find a way to add value first.

CORY: Right, absolutely.

ED: Can you give me an example of how you add value first, and how you do it in a genuine way?

CORY: Yeah, actually I had a large client hire me recently because a key person in their marketing team went on maternity leave. So the very first day on the job I wanted to do something that really proved my value to them. Well, I had already worked with their web platform before and I knew that that web platform exposed their web-server logs through the PDF via a URL on their website. And so I pulled up the URL on the website and I showed them that all that information that described their web-server activity was freely available for their competitors to pull down and use against them.

ED: Wow, not good!

CORY: And I told them, "Hey, you really should contact these people and have them block this URL." They had no idea that anyone could just grab their sensitive information off the Internet.

ED: And that's not part of the work you typically do, but you happened to notice this glitch, right?

CORY: Absolutely. Another example is a macro that I built for a client recently. In my field we spend a lot of time doing repetitive tasks with keywords ” bidding, changing budgets and that sort of thing. So I offered to build some VBA programs for a client at no cost. VBA is a programming language, and you can use it with Excel to automate tasks. So I offered to build a macro for this client to increase their productivity.

It's little things like this that make a huge impact. For one, it exposes me to what they are doing. So I get a better understanding of their business. Plus, they get something of value and they begin to appreciate me at a greater level.

ED: So then, going down that same path, what prospecting approaches are yielding the best results for you right now in this economy?

CORY: That's a good question, too. I have four different ideas to share. The first is word of mouth and helping others find clients. So let's say you know someone who may have an occasional need for a web developer, and you know a web developer that needs work. If you put the two of them together, both of those people are going to appreciate what you've done, and that's going to add towards the good will they have for you.

If you do that over time for multiple people ” all kinds of different people in different fields and different industries ” and they know you as the guy that does paid search (or whatever you do), that clear, simple message is going to resonate through all those different connectors and many of them are going to overlap. And as you help others find clients, those people are going to be more willing to send the same types of people back to you.

The second strategy that has worked well for me is going on LinkedIn and really getting on the radar of people who could help you out or who are in a position to help you out. Don't really go on LinkedIn like some people and post some random topic about something and trying to start a discussion just to spread your name. What you really want to do is find people who are in the same associations as you, or people who are in the same groups, trade organizations as you or in the same city ” something that resonates with you.

Then, just check out their profile in LinkedIn, and a few days later see who visits your own profile. Chances are that a lot of these people you checked out will also appear on the list of the people who have read your profile because you visited theirs. What that does is that now you're on their radar. It's almost like saying "hi." But if you can go on their profile and see who you are connected with, if you are really good friends with that person and you could get that person to kind of give you an introduction to that other person, then that social proof from that other person will help start that relationship off on a good foot.

ED: You are talking about using LinkedIn in a very organic way. So this is not about sending generic messages to all your connections in LinkedIn. I get those all the time. They're so annoying. They basically say something like, "Hey, we're connected here in LinkedIn; we should talk." But you can quickly see that they sent the same message to 500 other people. So it wasn't personalized or sincere.

However, you're talking about something very different. You're actually handpicking certain people you'd like to meet, correct?

CORY: Definitely. It's almost as if you are tailoring your resume for each individual person. In fact, I often max out the 300-character limit in every e-mail I send out via LinkedIn, so I perfectly phrase how I could be of value to that person. I make it zero risk, or I invite them for coffee or lunch if they want. But I try to do something that shows that it's not a generic, copy-and-paste e-mail.

CORY: So I may say something like, "I really loved your presentation that you did back in March" or "I really liked this or that" or "a book that you wrote" or whatever. I'm also talking about people here that are pretty high up on the ladder, not just someone that's a step or two above you.

I would encourage others to get creative and to be a bit bolder. E-mail the president of a company, e-mail the vice-president, e-mail the hiring manager and just try to start a legitimate professional friendship.

ED: I like it!

CORY: The third strategy is "meetups" groups. There are so many groups on where you can go and network with people. Now, as of this moment I have never actually gotten client from a Meetup group. But what I have gotten are connectors. So I go to some meetup groups to learn about other people, not to preach "I am here to sell you something."

I try to really learn about as many people as I can, and in my mind about a third of the time I am thinking, "Could this person fill a need for one of the other people in my network?" Again, I'm trying to connect people. And these meetings are often filled with quality people.

ED: How do you find meetup groups that are worth checking out?

CORY: I start by really thinking about what I do. I do paid search engine marketing. But I try to think about what types of people might be in a position to feed me clients, but whom I could also feed clients to. So I may not join a basket-weaving group, for example.

The way I began the search was to take a "Venn diagram" approach to brainstorming possibilities. I created a bubble called "paid search" in the middle and then I drew other bubbles, such as "web design" or "iPhone programming" - that sort of thing. And that got me thinking, "Hey, you know what? I bet there is an iPhone programmer that needs some online marketing to promote their app. Maybe I could talk to the organizer of that iPhone developers meetup group and say "Hey, I want to give a presentation for free on how you can promote your products with paid search." By doing that, I can be exposed to that group.

The fourth prospecting strategy I would suggest other freelancers explore is to start reaching out to agencies and firms that offer some of your same services. Start developing relationships with the key people in those firms and let them know that if a client doesn't work out, or if a prospect is not a good fit for them but would be a potentially good fit for you, to send them your way.

For instance, in my case I would go to a search engine marketing agency in Atlanta (where I live) and say "Hey, if you send me people that you don't want to bring on board then I could compensate you for that. Or if you want, I could do some comp work for you or we could work something out."

And if you get rejected the first time because they don't seem keen to help you out, don't write them off completely. They may have a change of heart at some point. A new person might come in who's much more open to the idea. The key is to just be genuine and helpful.

ED: What about approaching other competing freelancers with the same proposition? Have you tried that?

CORY: Yes, I have. And basically what I say to some of my colleagues is, "Hey, when you are at capacity, if you could send me your overflow, I'll do the same thing for you when I am at capacity." And you really have to trust your gut right there and get an idea for how honest they are, and you'll find out after getting to know a few of them. Sometimes it will be a little lopsided or one way - where one of you is sending more business than the other - but if you really believe the person is honest and fair, that's what really matters. And again, it's got to be the right person, because your name is ultimately tied to that person and how they deliver.

ED: Any parting thoughts or advice?

CORY: Always be honest, sincere and helpful. There are people that you'll come across that you really don't want to work with. There are clients that come my way and I know that I really should find them someone else because maybe someone is a better fit for them, or they need something that's a little different from what I offer.

That's totally okay because by finding them the right person, and by continuing to take leads that come your way and help those leads find the best for them, those leads will continue to come in. But when you start saying, "No, I can't help you" without at least trying to point them in the right direction or referring them to a couple of people or firms that would be a better fit for them, then what ends up happening is that people stop sending leads your way.

ED: Thanks so much, Cory! I appreciate you taking the time to talk with us today.

About Cory Jaccino

Cory Jaccino is an Internet marketing consultant living in Atlanta, Georgia. He's worked on the agency, client, and freelance side of the business and has managed a total of over $150 million in online advertising spend since he began working in paid search engine marketing in 2007.

His previous clients include household names such as Saks Fifth Avenue, Enterprise, Alamo, and National Rent-A-Car, and he's even managed the global paid search budgets for InterContinental Hotels Group (IHG), which includes the hotels Holiday Inn, Holiday Inn Express, Crowne Plaza and others.

Since going solo, Cory has become a Google AdWords Certified Partner, co-taught Google AdWords Certification classes and started a new Paid Search Meetup group in Atlanta to help local businesses better understand paid search engine marketing.

  • Nathan Collier

    Thanks for sharing Cory! Love the LinkedIn idea. I always thought the "who viewed your profile" thing was a little stalkerish, but I never thought to use it as a networking tactic. I'll be trying that one out ASAP.

    • edgandia

      Thanks, Nathan! Yes, Cory is a great guy -- very generous in sharing his experiences and ideas. Very much like another guy I know by the name of Nathan Collier. 😉

  • Pingback: Filling the void of coworkers | The Freelance Strategist()

  • Stuart

    I have a question for Cory - maybe Ed knows the answer. How did you (Cory) manage to do all the prospecting work while working full time? I understand doing client work evenings and weekend, but how did you connect and prospect while at your full time job.

    • Mark Keating


      Many of the strategies Cory discusses can be done during evenings and weekends: LinkedIn, meetups and networking, email prospecting. If you're still employed, one of the best things you can do is to beef up your professional network, starting with other people at the same company. Salespeople can be great assets, and the good ones will be doing some of the same things. Learn to leverage that. Building bridges BEFORE you need to use them is a great way to transition to full-time freelancing.

    • Thanks everyone for the kind words! 

      Stuart,This is a very good question.  In fact, it's one of the most important things that I do to drive more leads.  It's not always easy to do and you need to be patient, but here is the secret sauce, so to speak...

      I help OTHER people succeed... and THEY prospect for me.

      Doing this multiplies my reach and extends far beyond what I could ever accomplish on my own.  

      You are right, though.  There are only so many hours in the day.  We only have 24, and we have to sleep, but what if you had several (well-connected or not) friends and acquaintances who believed in the quality and the value of your work?  What if those people kept their eyes and ears open for you and referred people to you?  If you had only twelve friends and each sent you only one lead a year, you'd have one new lead a month.  Double the number of people and you'd have one new lead roughly every two weeks.  That's a lot of leads, especially if they are prequalified!

      So the question then becomes, "Where is the best place to invest my time?"  Also, think of WHO you should invest in.  You should invest in:

      1) people who value you, and
      2) people who reciprocate.

      If you listen to the monthly coaching calls, you'll hear my questions come up from time to time and you'll hear the hurdles that I go through.  Ed has excellent advice that he gives during these coaching calls and it has really helped me avoid burning time (among many other things) helping others who don't fit number one and two (above).  I can't overestimate how important it is to be productive with your time because you can't slow it down.  You can only (as far as I know) be more or less productive, efficient, effective, etc. 

      You only need to know a few connectors who are willing to connect people back to you.  Find a way to meet connectors (such as Meetup group organizers, etc.) and find a way to provide some value to them in a genuine, non-salesy way.  Imagine that you came to me, for example, and we connected.  My goal would be to know your goals and help you achieve them.  If you are looking for work and you let me know, I'll keep you in mind.  When the next opportunity presents itself, I will try and connect you with that opportunity. It may be a month from now or it may be six months from now, but I will remember you if we had a genuine conversation and I feel comfortable sending leads your way.

      In doing this, it strengthens our bond to some degree and you may feel the need to reciprocate.  Not everyone can help me, and I don't expect it, but if I like you and someone asks me for help with something that you do for a living, I will connect that person to you.  Hopefully over time you'd do the same for me.  It does me no good to keep that person from you.  I also don't ever want someone to feel that I couldn't either help them myself or find someone to help them who is a better fit.  That would send the message that I'm either too busy to help or that I couldn't, and if I'm not helpful, why would you want to connect?  So, I may take a few days to respond if I'm busy, but I absolutely do my best to help and I do get back to everyone who shows that they are someone I could be comfortable referring new leads to.

      Naturally, the word will spread that you are the guy/gal with all the answers and people will continue sending leads your way.  The point is that you will be leveraging other people who are your brand advocates and they will, through word of mouth, personally vouch for you.  Your connections will reinforce the prospect's buying decision before you've even meet with them.  This is very similar to getting other websites to link to you to improve your ranking within Google's search results.  It's like each person is a website linking to you and saying good things about you.  Who wouldn't want that?

      Honestly, I've made a lot of sacrifices along the way.  Some I regretted and some were worth it.  It's a learning process and you have to refine your intuition over time.  I've made some bad investments in people and clients, but I encourage you to learn from any mistakes you make and invest in people who reciprocate.  You'll learn quickly and get a sense for the people who just take and don't give back, but all you need is a select few who you trust who are also well connected and they will fill your plate with work.  Be patient and keep thinking, "How can I help this person?"  Like any relationship, if they're not reciprocating, move on to someone who values what you have to offer.

      As Ed said, some people reach out and they don't take the time to establish a meaningful connection.  If someone I don't know sends me a LinkedIn request with no explanation of why they are contacting me, I'm usually not going to chase them down and ask why they sent me a request.  That being said, if they type up a sincere and well-thought-out email, I will definitely respond and try to help that person.  There's nothing to lose, so why not?  In fact, the more that someone appreciates me, the more value I deliver.

      • Stuart

        Thanks for your detailed reply Cory. Great tips.

      • Anonymous

        Oh, wow, Cory! GREAT insights here! Thanks for sharing!

  • Great interview! It is so great to hear another professional's outlook to connecting is all about making connections without the immediate 'cash in' on their own business. The world returns what you put out.

    • Anonymous

      So true, Crystal!

  • Great and timely article. I will be loosing a sizable chunk of my yearly income the middle of March as a company I do work for is "changing their business model". 

    It is interesting that in the past week, through three different conversations, I have had leads drop into my lap. It must be a mental shift: mind over matter. I will no longer have my monthly payment "cushion" so maybe I have opened myself up to receiving other opportunities. Cory offers a great roadmap! Thanks! 

    • Anonymous

      Oh, Patty, I couldn't agree with you more! I've learned so much over the last 2 years about manifesting great things and "letting go" of HOW they'll come into my life. Fact is, we can't control every detail of how great people, things and circumstances will come into our lives. Our job is to ask... visualize... and have faith. The rest we have to leave to a power greater than ourselves.

      I had a similar experience earlier this year (big retainer agreement ended). At first I didn't take it real well -- until I realized a couple of months later that it was all for the best. New and better opportunities opened up.

      And strangely enough, a similar thing happened to me last week. Just when I was beginning to forget what I just mentioned above. 😉

      Thanks for your thoughts and comment!

  • Kirk Richardson

    Ed. Great interview. Thorough. I really like what Cory had to say about prospecting. Strangely enough, I've been thinking about checking out meetup groups as a prospecting avenue. Seeing it here just reinforces that it's worth a try. I plan to go into it with no agenda - meet people, and see what happens. That approach, rather than going into a group with a mind to sell, seems to work best for me and serendipity takes over. How do I know? Much like Cory, I left a corporate Fortune 500 company marketing job in October 2011 to go it alone. Thus far, I've booked 121% of my former salary for 2012 (and more work is on the way). I'm in the enviable position of being able to handpick my clients at this early point in the game. Life is good!

    • Anonymous

      I agree, Kirk. That's the way to approach these creative prospecting/networking opportunities. They're not the standard fare. But amazing things can happen when you follow your instinct and try new things.

      One of my best, biggest and most important clients a few years back came from going to an event that I ALMOST didn't attend. I'm still amazed at what came out of that split-second decision to show up, even though I didn't feel like it at the time.

  • Congratulations, Cory, in having so much success in freelancing. I admire your well-thought-out approach to getting new business. You have developed a blueprint for expanding your universe of contacts. You said something important: give to get. You can't always be asking for for the business. First, see how you can help the other person. Over time, you will reap the rewards coming back to you.

    • Anonymous

      Thanks for your comment, Jeannette! Give to get -- beautiful mantra. Timeless. 😉