I was lucky to be introduced to John, who became incremental in the project. John was happy to talk openly and candidly (as one can, when one is one’s own boss), and gave me a number of key referrals such as Corbin McGuire and Rusty Branch.

John’s interview is the one I show to recruiters who are thinking about striking out on their own. It’s hard work and requires a willingness to struggle at first, but can pay huge dividends in money and freedom.

You can read John’s full biography here

Jamie: John just to start off, in terms of your career thus far in recruitment and your sales career, what have you found the most fulfilling about your career thus far? 
John: What I’ve always liked about sales is how you can create a lot of flexibility while making a great living for your family. That’s the thing I love about it the most. I especially experienced this freedom when I opened my own firm about 12 years ago.  It allowed me to spend more time with my family while enjoying an unlimited financial opportunity.

Jamie: What are your thoughts on the relationship between entrepreneurialism and sales?
John:  Having started my own business in a sales-focused industry, entrepreneurialism and sales have gone hand in hand for me.  The skill required to complete every assignment I accept is essentially a consultative type of selling.  Some new businesses require an upfront capital investment, a support staff, a technology investment, etc., to get started.  None of those were required in my entrepreneurial venture.  All that was required is a phone, a laptop, and a determined commitment to a sales process.

Jamie: If you are working alone, how do you keep your energy levels high, and how do you keep yourself motivated?
John: That’s by far the hardest part of my job. However, for me, the pros outweigh the cons.  Right now I’m sitting in my study, which I love, but it requires some unique methods to stay motivated.  For me, this is the love-hate relationship that comes with sales.  It can really be a lonely profession at times, especially when you’re running your own firm.

Right now, I’m relaxed. I’ve got a hat on. I’m talking with you; that’s all great. I don’t have to worry about somebody coming in and distracting me, pulling me away from the job. The challenge with isolation is that it’s very difficult not to be able to communicate with peers, “What are our common goals? What are we shooting for? Do we want to sell the company?” There’s no ‘we’; it’s just me. That does make it very difficult. It’s funny, Corbin [McGuire, fellow interviewee] and I were just talking about this yesterday. He is a bit more fatalistic than I am. He has a unique opportunity to work with the Governor of Oklahoma, my home state.  He’s seeing his friend do something meaningful, with a lot of people involved.  He’s seeing that that energy that our friend Kevin Stitt [now governor of Oklahoma] gets from this It’s contagious and a lot of fun.  In a role like that, there’s a more tangible way to see how you’re impacting lives.  In our case, it’s, “Yeah, we’re impacting lives, but they’re one at a time, and it’s by ourselves, and sometimes it’s hard to measure the impact we’re having, etc.  It’s easy at times to feel like we’re just paying bills.”

One challenge in my business is that you can have low energy and low excitement about what you’re doing at times and still do really well financially.  I’m not sure if that would be possible in many other businesses.

In my low moments, I think, “I can find something else to do that I’m more excited about doing every day, but it would be a tremendous step backward financially.”  That’s not a great feeling.  I have found in speaking with friends of mine in sales that it’s not an uncommon feeling to have though.  Every career track has its positives and negatives, and again, the positives have far outweighed the negatives for me.

One of my friends, Rusty [Branch, fellow interviewee], has a unique perspective on this dilemma.  He told me (paraphrasing) “Hey, embrace the fact that you have a job that gives you some financial opportunities that others might not.” If you’re having those emotional lows, say, “Hey, the good news is you can go have a vacation whenever you need, with your family.”  I think that’s a terrific outlook to have.

As an entrepreneur, I’m learning it’s all about how to balance protecting your emotions versus just digging in and saying, “Hey, I’m going to hit it hard every day.” I think there’s a point where you have to protect your emotional stability.

Jamie: What sort of things are you incorporating in your day-to-day to protect your emotional stability?
John: For me, I don’t know that it’s so much day-to-day. I know myself well enough to know that if I go 8-to-10 weeks without some sort of break, and that might mean a long weekend with my wife, I’m going to go crazy because the job can be such a grind.  It’s funny how that works.  As a solo practitioner, sometimes the more successful you are, the more of a grind it can become.  As you have more success in this business, you get deeper into relationships with clients who give you more to do.  That’s a great problem to have, but it can be stressful nevertheless.

I’d recommend to all solo entrepreneurs who are feeling that loneliness and lack of purpose at times, just don’t forget why you’ve chosen to do it this way and remember all of the advantages you have over people who’ve chosen to stick with the regular corporate job.  If your company is successful, you’re probably doing better financially than even the most successful corporate people you know.  You have more flexibility than any of them.  Just take advantage of that and allow yourself to have breaks when you need them.  That’s why you chose this path less travelled.  I try to take a quick two-to-three-day trip with my wife or my entire family about once every 10 weeks.  I still have my laptop with me.  I work a little bit in the morning, just to make sure nothing falls through the cracks, but I reserve the balance of the day for recharging the batteries.

I’ve got to have that time away to be sane.

Jamie: How would you recommend aspiring salespeople determine whether or not they should go into sales at all? Secondly, what advice would you give them on choosing the correct industry for them?
John: Go into it with a bit of a plan.  Do some research as to industries that are hot, whether it’s healthcare, a specific type of technology, energy sector, etc.  The more focused you can be the better prepared you can be.  But ideally it would be a subject matter that’s intriguing to you, because it’s going to take some time grinding to get established in whatever you do.  Also, take various types of personality tests and predictive analysis tests to give you some clues as to how you’re wired.  There are different types of selling that may be best suited for you.  For example, I’m much better suited for a consultative type of selling.  When I’ve tried to focus on product selling, I’m not as successful.  I can do it, but it’s not as natural to me.  Think about concepts like this and ask successful salespeople what motivates them, how they approach their business, how they stay organized, how they set goals, etc.?  With a little research and introspection, you should have a decent idea of whether sales is generally a good idea for you and, if so, what type of selling fits you best.

Also, be smart about the numbers involved in what you choose to sell.  I know some salespeople who are less talented than others who are making significantly more money than their more talented peers, simply because they’re choosing to sell products and services with higher margins or higher ticket sizes.  This can increase the amount of money available to pay them accelerated commissions.

Take a step back from it and look at the math involved. “Okay, there’s only so much time in the day, and assuming I’m successful at selling whatever it is that I’m going to sell, what gives me the best opportunity to maximize my earning potential?” I have a friend, for example, who didn’t care what he sold, theoretically. He was not emotionally attached to anything.  Through his research, he determined that selling medical devices had a high earnings potential, as compared to selling pharmaceuticals and a couple of other products he evaluated. He literally made his choice based on the math of what’s possible within those businesses. I thought that was fascinating. I have to admit, I didn’t put that much thought into it when I chose my profession. I now think it’s smart to do that, especially if you’re in the early stages of your career and don’t have any experience in any industry yet.

I also learned a significant sales lesson from my next-door-neighbour a couple of years ago.  He was a product developer in the plastics industry. I don’t really know what that entails, but he worked for specific technology companies in that space, developing a specific type of products for them. He was in a large team, and he really worked his way up over the years.  He led initiatives for creating products, all technical in nature, with little sales involved. Then he suddenly developed a desire to get into recruiting for some reason. He started picking my brain about it, and I said, “Look, I have to be honest with you, you’re 45 years old. You’ve never done anything like this before. I don’t think this is a good idea.” I mean, if you could stay in that business, you’re already making a lot of money doing that, so why wouldn’t you just stay in the lane you’re in now?  Despite my warnings, he started his own recruiting business and within 18 months, he was close to making what he was in his old job.  I was amazed.  I’m convinced the reason he was successful so quickly was that he decided to recruit in the business that he knew.  He only recruits product managers in the plastics industry.  He had immediate credibility and great relationships in that space.  It was a brilliant decision that allowed him to bridge the financial gap from one type of job to another very quickly.  He’s completely re-created his career and realized a level of freedom he would never have been able to experience in the old job.  It was partly because he worked very hard, no doubt.  But his choice to leverage information and relationships he already had and apply them in a slightly different way is what made it possible so quickly.  I tell that story because it’s a reminder that it’s never too late to make a change if you feel trapped in what you’re doing now.  You just have to be smart about your decision and be willing to bet on yourself.

Jamie: You mentioned how you’ve got to connect the client-side to your prospects. Can you talk a little bit more about the pros and cons of being in a sales role like that where you’re creating a market versus just having a product to sell?
John: Yes. I’m glad you brought that up.  I think this gets into personality types. The same individual I mentioned earlier, the one who sells medical devices, he said,

“I’m young, this isn’t going to get any easier. So, I’m going to try something different now. I really feel like I need a tangible product to sell, where it is a formulaic, much more structured situation.” He did that, and it worked great, and now he’s doing fantastically well. I mean, he’s one of the best people in the country for this particular medical device he sells. 

He needed to have the benefits of a core set of products memorized. He needed to know what type of people buy them, and he needed to set up a very regimented schedule to go out and sell that. He is highly organized individual – probably a high “C” to use the DISC profile terminology.  He was keenly aware of this, which is one of the reasons he chose a tangible product with defined benefits to sell.  It worked perfectly for him.

For me, I’m the opposite. I love the ability to be creative in sales, and I like relationship sales. I like consulting-oriented sales more so than I like hard, tangible products sales. The more transactional and “commoditized” the sale is, the less I enjoy it. I like to help my clients with broad initiatives.  As an example, I might have a client say, “Hey, we’re trying to grow in the Northeast. What are some ideas that you have?” In that example, I might talk to them about various options, including acquiring a small company or group of individuals.  That excites me when I think about it. 

I am not frustrated by ambiguity, because it allows me to be more consultative to my clients and help them clarify what’s best for them.  I think that brings real value and it fits my personality. 

Jamie: What do you think is your biggest strength as a salesperson?
John: I think I’m intuitive.  I’m able to see the bigger picture of what my clients are trying to accomplish and help them craft appropriate solutions to achieve their goals.  When I’m choosing candidates to present, I try to select people who match the people they’ll be working with first and foremost.  I’m pretty good at assessing that fit.

Part of what I think makes me successful is the ability to see things in different people that, in my estimation, make them a good fit for one another and not get emotional about all of the things that happen, because each side has very strong opinions. Even very laid-back people, at some point, when you’re asking them to spend significant money or completely change directions at some point get kind of uptight.  Even the most meek individuals will at some point say, “Wait a minute, this is my career. This is how I pay my bills. I need to be very serious about this.” When you squeeze the orange, whatever they are mentally dealing with starts coming out. My greatest strength is that I do a good job of distilling a person’s story, or perspective, or what’s important to them. Then I’m able to remain level-headed and be the voice of reason when they start getting tight, and they start getting worried, and say, “I can’t believe they would possibly consider offering me that.”

I’m able to calmly walk them through their stress.  “Hey, that’s fine. Let’s go back to your original reasons for wanting to make a move or the original reasons for wanting to speak with this firm” It’s just like when you’re selling books door-to-door. One of the great lessons I took away from selling books is when someone’s getting frustrated – and you probably remember the phrase from sales school, “frustrated people don’t buy” – I think I do a good job of taking them back to the beginning and reminding them, “Wait a minute, wait a minute. Why were you initially interested in this?” Maybe they wanted a better lifestyle, or more money, or whatever the real reasons are. Then I’ll remind them, “Okay, so is it fair to say that those things have nothing to do with this small hesitation?” In my business, it’s not uncommon that you have both a frustrated candidate and a frustrated client at times.  But they’re still a great fit for one another, and it’s my job to help them navigate through it and get the deal done.

I do a good job of being that punching bag that absorbs those issues and stays level-headed with them. So that’s probably one of my greatest strengths.

Jamie: If one wanted to be an entrepreneurial recruiter, how does one go about that?
John: I’ve only known one person, my my aforementioned next-door neighbour, who started recruiting later in his career. He’s an extremely unusual example of someone who was successful in shifting late in his career to this business after a long, successful run in a different business. With that lone exception, every successful entrepreneurial recruiter example I know is of a person that had recruited before as an employee of a search firm.

All of these individuals had experienced success in the business, or they had some belief level that theycould be successful. I think that’s the number one prerequisite actually.  You have to believe you can be successful. I wouldn’t recommend doing it unless you have had some success. At the end of the day, all successful entrepreneurs I’ve known are calculated risk-takers. They believe in themselves, and more importantly, they’re willing to put up with the initial suffering; the initial six months, a year, maybe even 18 months of working through non-competes, non-solicits, being willing to get creative, and find new territory if they need to be successful.

If I had to boil it down to one factor, it’s that they have to be committed. Entrepreneurial recruiters have to want it badly enough that they’re willing to wade through the initial difficult stages.  Have a pre-determined commitment plan and timeframe and stay committed to it.  Maybe you say, “I’m going to do this for a year as hard as I possibly can and only then will I consider going to do something else.” Most people who started their own business, in my experience, they know within six months whether they’re willing to commit to this or not and then they either get out, or they stay in it for the long haul.

Do you want it bad enough that you’re willing to put your actions behind your words? Those who do, if they’ve had some success prior, I can’t remember an example that they ever go back to a firm after that because it’s so hard to give up the freedom and the increased percentage of the money that you can keep.  How bad someone wants their freedom is a key factor in the decision-making process in my mind.  I’m learning that about early stage professionals in all industries.  Freedom is worth more now than ever before.  It’s one of the first qualities in a job that people seem to want. They want freedom, they want their opinion to be heard, and they want to be highly valued, not necessarily just compensation-wise. I used to get quite frustrated with that, “How can they not see the bigger picture? How can they not see that it doesn’t work that way?” Then I started to think, “You know what, maybe it does now work that way.” However, believe me, there are sacrifices they’re going to have to make in order to get that freedom.

I saw an article, where Jeff Bezos was being interviewed, and he made the comment that was something to the effect of, “The new system, the best practice of how you work with people in the future, is going to be total freedom.” They will have complete autonomy and freedom to work from anywhere, but they’ll need to be accessible 24/7.”

Now, when you first hear that, your response might be, “Oh, that’s awesome!  Total freedom.  I can do whatever I want, work wherever I want.” But if you’ve experienced that need to be on a call, where you have to respond right then, it’s tough no matter what’s going on. There’s a very definite trade-off. That probably is where a lot of these companies are going.

Jamie: In light of that changing dynamics and ways of working, what advice do you have for aspiring salespeople?
John: It’s more of an internal evaluation than it is an external evaluation. Unless you have a very specific plan; “I want to be an engineer or I want to be a something that’s very defined, and I want to be a something that’s generally more technical in nature.” Unless you want to do something like that, then, in my opinion, sales is an option for anybody. I think the questions you have to ask yourself is, “Am I curious about other people?”

I think you can make money with that mindset in sales.  Some people make money doing sales without that for a long time, but I don’t believe they are happy, I don’t think they’re fulfilled doing it. I call it an intellectual curiosity. “Am I a puzzle-solver? Does it motivate me to help people act in their best interests? Do I even care if they do that?” Or, “Am I just doing it so I can get a paycheck?” If you’re the kind of person who thinks of the notion of sales as helping people get more out of their life, get more out of their company, make more money, be more fulfilled, that’s the right mindset for sales. If you hear me say that and you’re motivated by that line of thinking, you’re probably a decent prospect to go into sales.

In other words, making uncomfortable calls, if you don’t care about the outcome that you’re trying to create, makes no sense to me. I’d be petrified to make that call, and I would think that was the worst idea in the world if I didn’t see the bigger picture of how I’m helping the people.

Here’s the thing. Whether you care or not it’s still going be a hard call at times. I don’t think you’re going to consistently – over a 20-year career – make those calls if you don’t care about the people involved.

Jamie: If you had your sales career again, what would you do differently?
John: I feel like I’ve been so blessed with the way that it’s worked out, that I hesitate to say, “I would have done it another way.” I might have opened my own business a little sooner.  I’ve probably always been a little too risk averse.  I’m not risk averse from the perspective of, “Do I think I could make something work?” – I’m more risk-averse from the perspective of “Do I want the extra work that it would require?” Some people would have expanded their businesses much faster and more aggressively than I have.  Sometimes, even when I know I’m leaving money and possibly even more fun on the table, I’ve chosen not to be as aggressive as I should have in growing.

Once you start having a family, things change. You can’t just think of yourself.  For me, decision making becomes, “If I did that it’s going to affect them too.” If it was just me, I could live very lean if things changed dramatically financially for a period, but I’m committed to the ultimate outcome.  When you’re on your own, that’s cool. I used to live on nothing; when selling books, we lived on two hundred bucks a week. You can do that if it’s just you, but it changes everything if you have a family.

Jamie: Can you tell me about a time when you didn’t make a sale, but it taught you something really valuable?
John: I sold books with Southwestern, then I worked for Tom James – I worked there for about a year and a half, – then I went directly into recruiting.  So I basically I have had three jobs in my life.

Southwestern taught me the tremendous work ethic and belief in myself.  It gave me a strong vision of what type of industry I wanted to be in. It made me realize I want to do sales. Those are the things I got from Southwestern. On the other hand, Tom James taught me how to create a professional schedule and manage my day in a realistic way.  The challenge in the role at Tom James is I was only 22 years old and I needed to call on much older, well-established executives in order to sell the level of product I was representing.  You just have to figure it out.  It was very much baptism-by-fire, and I learned more that has helped me in my professional career in those 18 months than I did in five summers selling books.

There was a sales manager at Southwestern named Allen Clements.  He used to make the comment that everyone likes sales when they’re selling, but when they’re not selling, they hate it. That’s obviously true.

I hated the job most of the time I was at Tom James, but not because I hated the products or the people involved.  I just wasn’t any good at it.  I wasn’t selling much of anything, and it became very frustrating.  When everything was clicking, clients were into what you were doing and buying suits, it was a very fun place to work.  But again, the problem was I was just not good at it. In fact, production-wise, I was kind of horrible at the job, even though I was working really hard. I would go out in hundred-degree weather up and down office building steps, elevators, just slinging this fabric all over the place, and then come back to the office at three o’clock and make 80 dials to try to set up all my own appointments for the next day. Here’s the problem.  I didn’t know anything technically about the products I was selling and I was struggling to grasp the concepts that helped you gain traction in that business.

To answer your question, here’s the lesson I learned from not making a sale. One day, I was selling suits, unsuccessfully, and had a couple of appointments fall through.  For me, this meant hitting the car dealerships, where I knew I could always find an audience, for better or worse.  The salespeople there would always make fun of you, as they’re getting beat up themselves from selling all day, and then here you come selling to them. They’re like, “Oh, here’s the Tom James guy, you got any free ties today?” They’re having fun at your expense. At any rate, I did have this one general manager, a big car dealership in Oklahoma City, where I was at the time. He was kind, as it turned out. He said, “You know, you just mis-measured my pants,” that he’d paid $400 for, and by “mis-measured” I mean I was off by 2 1/2 inches – just an egregious mistake on my part. The guy tried the pants on, and it was obviously a horrible fit. This was the fifth time that particular week I had to send something back to be remade, which means the company is making virtually no money on it. Tom James doesn’t like that at all, and they’re not enjoying paying me as they’ve made no money on the products I’m selling and I’m killing their reputation in the process.

The guy says to me, “John, I have to tell you something, and I really mean this with great respect; I like you, and if you keep doing this, I’ll probably keep buying stuff from you just because I like you, but I think you deserve to know this–” keep in mind I’m 22 – he says, “You’re not good at this man.” The way he said it was heartfelt and sincere; he was like. “I really have tried to give you the benefit of the doubt here, I’m trying to work with you, but I just have to tell you I’m not sure this is for you.” 

I initially got mad. As I got back to the office, I was, of course, deflated. I’d made $39,000 that year working 85 hours a week, and when I did the math – I could’ve worked at McDonald’s and made roughly the same money in the same hours, so I thought, “You know what, it’s okay– did I put my best effort in? Yes.  Have I worked as hard as I can for the past 18 months? Yes. Does it make sense for me to keep doing this? No, it doesn’t.”

I have to admit when I left that job I felt like – was that Southwestern thing just a joke? I was good at that, but was it because it was a sympathy sale where I can say, “Hey, I’m a college student trying to pay my way through school,” and they sort of bought my books because they felt sorry for me?  Am I really not good at sales?  In retrospect, I know this was the best thing that could have happened to me.  And I learned a valuable lesson in the process – if you’re not succeeding at something after giving it an earnest effort, it’s okay to move on from that job with your head held high. Go do something else if it’s not working for you – and this is coming from the same person that said you need to be long-suffering if you start your own company.

I would specifically say for people who are very early in their career. As a recruiter, you notice people get free passes; they get mulligans for the first few years of their career as they’re trying to figure out what they want to do. Once you get into years, 5, 6, 8, 10+, you start getting less free passes by potential employers when they see frequent or sudden job changes happened in your background.

But in those first few years, I think it’s generally accepted that, “Hey, this guy is trying to figure out what he’s good at.”

On the heels of my worst day at Tom James, walking out of that car dealership, I would have told you, “I’m so deflated, this is the worst day of my professional life” and it turned out it was the best lesson I ever learned – listening to that frustrated customer and going to do something else.  That’s when I started working with Rusty Branch again in the recruiting business in Dallas, and the rest has turned out great.

Jamie: On the flip side, please can you tell me about a time when you did make a sale, and it shows off the skills and the knowledge you’ve developed over the years?
John: There were two that were almost identical.  One of them just happened, and the other one happened about four years ago. These were situations where companies in my industry wanted to expand geographically, but they didn’t know who the players were in that those geographical markets and didn’t know how to do it. They knew they needed to grow and they didn’t have any presence in a particular US geography.  The other situation was a client who didn’t have a presence in a particular service line that they knew I recruited.  Both of these situations were in my areas of expertise.  I was able to put together large teams for both of them, which was a great deal of fun.

Those were great in that they allowed me to see my benefit in this industry, in that I was able to help them create this idea out of thin air and execute on it.  They started from a place of, “All we know is we want to grow but we don’t really know how to do it.” The reason group hires make me feel good, when you’re talking about multiple people moving into a new company together, is that every one of them has their own story of what they’re looking for. The prospective employer has one vision that they’re trying to accomplish, but in reality there may be 8 to 10 to 15 to 20 individual people need to connect to realize that idea, and all of those needs must be somehow satisfied. If two people decide that’s not for them, they’re not going to do the whole deal, so behind the scenes, I have to recruit nine people individually and keep them all committed to this bigger process. When those come together it’s just awesome because then you realize, my company just added 15% additional revenue to their firm, they’ve got a new service line, there’s a nice press release that comes out, and I’m not mentioned, but I know I was a huge part of it. I know they wouldn’t have been able to do it without me.

The reality is when I do the normal one person here, one person there, those are also meaningful – they’re impacting both sides. But it’s those larger group deals where I am reminded, “That brings real value, as they’re not able to make that move without me,” and that’s cool. It reminds you that it’s not just a low-level sale where the only value you’re bringing is that you’re willing to dial the phone. It requires consulting to help all these people stay on the same page when they all have very different personalities.  They want the same big picture goal, but they all get side-tracked by their own individual goals and challenges.  I have to help them stay the course, and I feel like I’m spinning plates along the way to help them all get to the finish line.

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