PHL The Hathaway Group
The Entrepreneur’s Guide to Recruitment: Innovative Approaches in Business and Career Advancement

In this insightful episode of our podcast, we delve into the dynamic world of entrepreneurship and recruiting with our special guest, Ryan Levy of Cruit Group. Join us as we explore the intricacies of starting a business, the evolution of the recruiting industry, and the impact of technology on these fields.

Listen to the podcast episode here!

On this episode, my guest is Ryan Levy. Ryan is the owner and founder of Cruit Group. It’s not pronounced crit,  I had made the mistake of pronouncing it, but it’s short for recruiting. So Cruit Group, they’re a local recruiting group specializing in a variety of fields.

With a focus on relationships. Ryan has always had that entrepreneurial bug growing up in a family of entrepreneurs. Now in this episode, we talk about the time to start a business, and what goes into recruiting, and Ryan shares his top tips for anyone looking for their next employer. If you enjoy this episode, do me a huge favor, subscribe to it, and leave us a review.

Now let’s jump into this episode.

Ryan Levy. Welcome to the show. 

Thanks, man. Thanks for having me. Excited to be here.

This will be fun. So we go back to high school.

Yes, we played played a little baseball together.


Man back in the day. Good Old Days. Fun, fun times. But we were here today because we wanted to talk about your business career group. I’ve been following you. Since you’ve kind of started a career group and are kind of curious about that business and what you do and then we’ll talk about your other businesses as well. 

Sounds good. To start, it’s Cruit Group.  [From the word] Recruit.

Okay. Got it.  It’s funny I never thought of that.

I guess because I’ve been in the industry so long. But when I talk to new customers or new candidates, that is a common mistake. So I won’t hold it against you. I started Cruit Group about three and a half years ago. So I’ve been in the recruiting industry going on 12 years now. So I guess I’m an industry veteran. But started my recruiting career in Chicago in 2012, which I believe was 2012. And moved to California, after eight years, and spent a couple of years there.

But finally started my firm. I always knew I wanted to start my firm. And finally did it a few years back. And it’s it’s been fun. It’s been a big learning experience for me. And we’ve grown exponentially, especially in 2023. So looking forward to a big 24.

So take us back to the beginning,  getting into the recruiting business, how to? Is that something you’re always interested in? Or how did that come about?

I guess, to take a step. back even further, I’ve always been an entrepreneur. Growing up by flipping baseball cards, washing cars, and mowing lawns, my sister owns a hair salon and Eastlake, I used to run that place in high school and college when she was having kids.

So I’ve always had that entrepreneurial itch. After college, didn’t know what I wanted to do. I’m a people person, I knew I wanted to do some sort of sales. And I’ve always been money-motivated. So honestly, the only reason I got into recruiting was because I saw these 23, 24, and 25-year-olds out of college, friends making a ton of money. So I just decided to get into recruiting. And that’s honestly the only reason I got into it. And then I fell in love with the business.

So I started with a Tampa-based company, actually, in Chicago, a company called – force publicly traded firm. Really good training. So I went through the process with them. I spent six years with them and then went to a smaller firm before ultimately starting my own.

Okay, so talk to me about the recruiting business or one what do you love about what did you fall in love with? What was that piece?

I think it’s just you’re constantly learning every single day. , I’m big on knowledge,  knowledge is power. But it’s also you’re helping people? It’s, super rewarding to help someone advance in their career or help them land their dream job or help them land a job at a dream company. So to me, that aspect of it is cool. And if you’re doing something that that you enjoy, or you’re passionate about, the Money Follows, And so that makes it quite enjoyable as well.

Do you think it could have been any other business?  if you’re helping somebody?

I think I mean, you could say that in sales, you could say that. And in marketing, you could say that in a lot of different industries. If it’s something you’re passionate about, and you’re helping people, I think you can have that same effect. 

I think because I think back to when I got started into real estate,  I was gonna I wanted to be an investor,? And I’ve talked about that before, but two years in I was, I’ll invest or I’ll save money, then I’ll start investing in real estate. And then I fell in love with the business for that. Those same reasons. You’re helping people, the relationships, the connections,  sure,  that journey is fun.

I can see the correlations there. I used to want to be in real estate myself I like nice things and helping the money or is, the money it’s it. There are a lot of correlations there for sure. That’s cool. So talk to me about your I guess your job or your day-to-day for anybody because I don’t I’m not familiar with how the recruiting role works, and I guess explain that. 

So there’s two worlds in recruiting you have corporate recruiters and then you have agency recruiters, I’m on the agency side. So basically what that means, on the corporate side, you work for one company, you work internally for a company. Let’s just take Facebook, for example, Facebook hires 1000s of people every year, they have a huge team of internal recruiters. And that’s all they do is work on Facebook jobs, the agency side, essentially works with all sorts of different companies that have they spend money to hire outside agencies to fill their jobs. So that’s really what our focus is.

Being that we’re a smaller firm, we tend to focus on startups and smaller to midsize businesses,  here locally in Tampa, now we work with several law firms, from people that I grew up with, and things of that nature. So just more of a focus now on smaller to medium-sized businesses. So it’s, in your second year, you’re connecting with the different businesses trying to get them to hire you to help them with recruiting. 

So we operate on a contingency basis. So basically, that just means they don’t pay us until we’re successful in finding them a candidate. So on the agency side, there are two sides of the business as well, you have the recruitment side where you’re going out and finding candidates for jobs. And then you have the sales side and the sales side and the recruiting agency world is essentially going out there and trying to connect with businesses that are having trouble hiring, or just having difficulty bringing in the talent or attracting the talent, they don’t necessarily know how to do that and how to grow. So basically, we go out and get job orders, and bring them back to the recruiting team who then go and find the candidates. ,

Is that is there a standard?  Does it take X amount of months or whatever to find or fill a position? Or? It depends on the business. 

I think it depends on how good the recruiters are. Honestly, I think that’s something that we pride ourselves on is how quickly we’re able to identify and attract talent. Of course, there are several methods to do that. But I would say on average, if Donnie wanted to go hire an assistant. In the real world, it might take you 60 to 90 days to find someone, and a lot of it too is convenient.

Let’s take a managing partner at an attorney for an example or at a law firm, for example. They might have the resources and financial ability to post a job on LinkedIn Zip Recruiter or whatever site you want to use. What happens is, that they get hundreds of applications. And they don’t have time to go through them. And they have to filter an interview. And it’s a very long and grueling process. When you’re working with a recruitment agency, they take care of all that stuff for you. And they had hunted.

And then you’re just interviewing the person. So we get to know our client’s culture their must-haves of course,  salary requirements, benefits, all that type of stuff. So essentially, we’re going out there and selling the company on behalf of the company. 

That makes sense.

So let’s go back to starting group group. You talked about always having that entrepreneur itch when do that, Okay, I’m going to start my own business now.

Probably a year or two in, I knew it was the end goal. Once I learned the business and saw the potential, I always knew that was the end goal. So I started as a recruiter moved into sales, moved into leadership, and managed a very big sales team at K-force at one point.

And I kind of always just knew that, in the end, I would, I would own my firm I saw the inner workings of a large firm, and what it takes to operate any type of staffing agency or recruitment agency because it’s all the same no matter the size, but definitely knew at an early age and, or early in my career, I should say.

I made the move to a smaller firm in Chicago because I wanted to prove to myself that I could start from scratch somewhere else before I started my firm. Okay, so I spent so it’s all,  chess pieces, strategic moves throughout my career to get to where I am now.

So I spent two and a half years at a smaller firm and had to start my book of business from scratch again because I had a non-compete and all that. And finally, rip the band-aid off and went all in on my firm after two and a half years at this small firm, in Chicago. 

Was there any [entrepreneurial] itch to start earlier? So you started recruiting one to two years and this is gonna be your career? And then, at some point, if you want to start your own business, why not start it, too? 

I think there were thoughts of it. Even before I went to this smaller firm in Chicago for a couple of years, I almost did it then. And my father was willing to float me the money or the investment to do that. He passed away about six years ago. So rest in peace, he’d be proud of me now that I finally did it. But I had the urge.

And one of my mentors kind of talked me out of it. So I think the timing was, for me, for sure. The recruiting business, it’s a very relationship-driven business. There’s, there’s a lot of independent recruiters out there that don’t have experience. And, they’re just good salespeople. But ultimately, a lot of those people fail because they don’t know what they’re doing.

You can get opportunities if you can sell, but, if you can’t deliver your opportunities are pretty limited. So I just think it was it was a time you just have to put in the time and build the relationships to be truly successful ultimately.

I think about that in real estate. I think now in real estate bigger teams are a big thing. And so new agents getting into the business,  a lot of them are joining teams, and I think there’s, there’s some positives to that I went the route of just being a solo agent.

Probably took a little bit longer to learn the business and learn things, I’m sure.  but so having a team having mentors and stuff is sure powerful.

For sure. I mean, and I think working at a bigger agency helped me ultimately, I mean, I worked in, your typical boiler room sales environment. When I first started, it was  I used to go under my desk with my hard phone, before cell phones, I mean, cell phones were around, I’m not that old, but, we still use desk phones. And, I’d go under my desk because it was so loud. And footballs are flying across the room just to try to close a deal.

And then, you go to a smaller firm, it’s a lot different. But I mean, to your point on mentorship, that’s been important to me throughout my entire career. And, I try to be a good mentor to the people that work with me now

What do you see the use of I read some stats on,  AI affecting recruiting and that sort of stuff. How is that intertwined with your business?

It’s interesting. I’ve always been, somewhat techie. I mean, even in the first eight years of my career, I only did technology recruiting, we mixed it up and did pretty much anything, just depending on the relationships.

But I use it daily, honestly,  I utilize ChatGPT for various things, whether it’s writing an email or sales campaign for automation,  automated emails, and things that, or helping a social media post, or writing a job description,  the fact that you can write a job description in, 30 seconds now, or less is incredible.

So I certainly see the value in it. And I will always be willing to utilize new technology. At the same time, I’ve heard since I started recruiting that, robots, were going to take our jobs or AI was going to take our jobs way back then.

I think what’ll happen is it’ll weed out the bad recruiters, and it’ll make the good recruiters even better. If you can just utilize technology to become more efficient, or a better writer, whatever it is because there’s recruiting as sales.

So if if you can utilize technology just to become a better salesperson, why wouldn’t you do it? I think the people who don’t evolve are the ones who are going to die for lack of better words, I’m a big evolve-or-die guy.

But at the same time, there’s always going to be that human aspect. Just in real estate that human connection in that relationship will always be important. You can’t have AI do all of your recruiting and talking to candidates and things [like] that. There’s that human element that is still going to be there. 

I think it’s interesting. I agree. I think the relation is any relationship business and in most businesses, there’s a relationship at the center of any deal or anything that. So, I think that keeps I agree,  it keeps,  the ones that are evolving and using technology, it keeps them in the business and makes them even better at what they’re doing anyway

The Entrepreneur's Guide to Recruitment: Innovative Approaches in Business and Career Advancement

I mean, I use it for contracts now too. I mean, I don’t need to spend a ton of money to hire an attorney to write me a contract or, I know. It’s, it’s not foolproof. I don’t just, put something in ChatGPT and I’m, and then I let it rip. 

I’m good, I’m gonna go through it, I’m gonna be, No, you need to change this but it’s cool that you can use it for things that. I mean, I use it to write master service agreements and statements of work and all sorts of different things. I do have an attorney that I’ve had, I’ve shown him, hey this is he this looks pretty good. I just like this but the thing is smart. So use it.

It’ll be interesting to see, how the attorney’s role changes to, because if you can just write a draft of your contracts and that sort of stuff. Maybe you have them to review things or, or whatnot.

100%. I mean, if you [know] how to the biggest thing with AI and ChatGPT specifically or whatever, using Google Bard, or whatever they call it. I think you have to learn how to prompt the thing. That’s the big thing learn how to talk to the machine. And if you can effectively talk to the machine and coach it the sky’s the limit.

It’s cool.

It is.

So I have a couple of stats here. And I want to kind of get, your reaction to them. So one thing I found 86% of professionals prefer remote work, at least part-time. You’ve seen a lot of that.

It’’s been an interesting evolution in the professional workforce. I prefer remote work still to this day, I worked remotely, a good amount before COVID. And then naturally, during COVID, full transition, transition to remote work, Cruit Group is all remote.

But at the same time, I certainly see the value in face-to-face interaction and face-to-face work. Because you can learn a lot just by being around people in the same profession as you and listening to them on the phone or being in a meeting with them, whatever the situation is. So I certainly see the value of it. But you’ve seen him, we’ve seen a major shift across corporate America, and startups, whatever you want to call it, where they’re pushing more return to Office and less flexibility.

But ultimately, I think the companies that will succeed the most and continue to grow are the ones that are offering, a flexible first environment. , I think people realized during COVID-19, that they can be just as effective, if not more effective when they’re remote. But also, not everyone can succeed in that environment.  it takes a unique person who’s very disciplined to be able to be 100% remote, there’s no doubt about it. So I mean, I can see both sides of the coin.

But I think the companies that are mandating five days a week on-site,  that’s just such an old-school mentality, and I think it’s foolish.

I’m the one coming into the office, and I struggle working from home. Okay. I think part of it too, is when I first started in real estate,  being in the office,  learning from other people being able to go down and talk to my broker. It’s a big part of it. And I think that’s kind of, the piece that I enjoy the most about,  being in the office.

And then I mean, my business too, is out in the future, and that sort of stuff, too. But one of the other stats I read, too, was I think it was, it was close, it was  75% of them 70 to 75% of the workforce felt that they were more productive working from home. 

I believe it, it’s just what I said, it’s not for everyone. I mean, look, I’ll do a peloton ride in the middle of the day. I’ll do laundry, I’m working on my other businesses from time to time, and I’ll record a podcast in the middle of the day.

I think you have to be good at time management. That’s something that’s that’s made me successful.  I used to be organized chaos. And in a way I still am, I’ve got sticky notes all over my desk, but I also live by my calendar.

Yes, I work a 12-hour day every day. But, if I’m not busy on a Thursday, I’ll go play golf. There’s nothing that’s that’s gonna stop me from doing that. If I’ve effectively managed my calendar. So it’s really about finding the balance. And if you can be productive in any job in any industry that’s the bottom line.

If you’re producing, no one is going to be breathing down your neck being, Okay, you left at 5:05 when you should be here till six.  it shouldn’t matter as long as you’re being productive. I just think the workforce nowadays wants more flexibility, especially people with kids or, maybe they’re caretakers, whatever it is, you as an employer, should be more flexible. That’s all as long as they’re being productive. We’re gonna set the expectations.

Have some boundaries there. This is along the same lines, but 77% of workers say they’ve accepted a job without visiting the physical office.

I believe that. Absolutely. I mean, when I first started recruiting, we were so segmented, that I only focused on Chicago or the suburbs. And now of the 30 clients or whatever that we actively have. I think maybe three of them are in the Tampa Bay area. They’re all over the US.  And a lot of them are still hiring through Zoom without face-to-face interviews. And, that you might not ever go into an office. So, 77% seems pretty accurate.

Do you see any issues with not having, face-to-face meetings, when when hiring or just hiring through Zoom?

I think it could be a little risky because people are good actors or are full of crap. A lot of times  I’m working the people business, so I’ve been burned every way you could imagine.

So, I mean, maybe I have some trust issues. But, I would say if you’re going to hire someone without meeting them in person, you should at the very least check references.  However, at the same time, I also think references are kind of a joke, because the references that people are going to provide you are going to course they’re gonna be good.

Of course, 90% of references are good. If you can, you can sneak in a backdoor reference to a reference on them without. That sounds a little shady. But Hey, I saw you guys work together at this company. How was your experience with this person? I don’t think there’s anything wrong with doing that show personally, but references are kind of outdated, in my opinion.

So let’s talk about Wags and Wine a little bit. And from what I’ve seen, it’s a cool business. Really cool idea. Where did it where did it come from? And, what is it?

Crazy idea. Jeez, when we were living in Chicago, probably back in 2014. , winters are terrible up there. And we’ve always been dog people. We wanted to open a wine bar that was dog-friendly. So we bought Wagsandwine.com. In  2014, maybe it was even 2013. It was a long time ago. Again, entrepreneurial thing. I just buy websites, if I have a good idea sometimes or, I had a dream last night, that I owned this dog company.

And anyway, so we bought the web domain, did nothing with it for 10 years, or however long it was, and tied it into the recruiting world. I was recruiting for a pet tech company in San Francisco. And I got pretty close with a GM. And she was a brilliant woman, an entrepreneur. And she owned a subscription box company that she ultimately sold to Walmart for I don’t know millions of dollars.

And this was during peak COVID that I was working with them. And somehow somehow, I had the idea that we should own Wags and Wine, or we should make Wags and Wine into a subscription box company. We were living in Oakland the Bay Area. COVID in California was a different beast we were basically on lockdown for a year it was wild, and way different than Florida.

Hence why I’m back in Florida. But we were close to wine country. , Oakland’s an hour from wine country. So we visited wine country a lot. And during COVID, we were getting a lot of wine deliveries, we were getting a lot of dog tree deliveries, and dog product deliveries. So my wife told me it was a dumb idea. And I was crazy. But after she let it stew for a few weeks, I talked her into it. And the rest is history.

So essentially, it’s a subscription box company that features small production wineries and healthy dog treats and goodies from small producers as well. You get two bottles of wine and three to five dog products. You can do the monthly every other month quarterly. It’s a great gift box.

But we had no idea what we were getting into. Now we make wine we become a winery. Cool. We have a wine brand called Hair of the Dog. Which you can also get in our subscription boxes. Or you can buy it without being a dog owner if you just want to try our wine but, it’s been an interesting journey. Man. I knew nothing about the wine industry. I just love wine.

And, I think it’s interesting.  one thing that stood out to me,  having this conversation with the now is the time that, an idea comes up and then the time that you execute or realize that idea  In this society even we want everything now.  There’s a lot of time there that ideas it takes time to get to work through the kinks.

That’s so true, man. I mean, there were several times when I wanted to give up. We don’t know what the hell we’re doing. And it’s been cool to see the evolution of the product itself, the Wags and Wine product, if I could go back and look at our first box to what we’re shipping out now that the product is 10x better at first, we had breakage, we had bottles exploding and just things getting Returned to sender and just an absolute nightmare.

And we have it all figured out. It’s a great product now. And it’s funny two and a half years in now, it’s starting to grow. So it’s cool to see that but, sometimes you just got to go for it. And you got to believe in it and continue down the path. It’s tough being an entrepreneur, though. It’s crazy. And you just got to believe in it. And you got to keep going.

What do you love about entrepreneurship the most?

I think it’s the creativity. I’m creative in some aspects, and in others, I’m not creative at all. But I think it’s it’s the ability to create something and see it grow. And it’s also the freedom,  I  said, I can go play golf on a Wednesday afternoon if I want to. But to me, it’s the freedom as well,  not working for the man.

I was always, there’s some power in that.

My father owned a tire store back in the day when he was younger.  I said, my sister owns a hair salon. My brother owns a medical practice. So I think it’s also something you could be born into. I mean, you can do anything you want to do. You don’t need to be born into something.

But it helps to have those mentors. If you grow up in a household of entrepreneurs, and you see people working for themselves, it’s different. You believe that you can do it.

Having that belief, going back to that blind faith. That’s a big part of it? You have this idea. But a lot of I mean, I’m sure everybody has ideas but they just don’t execute them.

For sure. I think people are just afraid to do things that it’s against the norm,  the way society is trained people is to not take risks and not do those things. It’s have a stable job working nine to five. But in today’s day and age, you can do anything with social media and, you can start a website and you can start a business with minimal income or minimal investment, I should say. 

Going back to that you just remind me of your recruiting business. Do you recruit on Instagram, I saw some stuff that, where, people are finding jobs through Instagram. And I thought that kind of.

So that’s one of my goals for this year is to be better on social media. We have an Instagram account. And we have a LinkedIn page. And I want to create more free content on Tiktok, and Instagram and stuff  that. Just giving people advice and building a brand and all that.

But we have made placements, depending on the role I’m not going to go looking for a CFO on Instagram, But maybe we’re working on a social media marketing manager or receptionist or anything really.

In certain industries, I’ve found or certain professions, people need to be more active on LinkedIn. So you have to get creative. Okay, when you’re looking, I’m a big LinkedIn guy I live in  LinkedIn is my Facebook or whatever. 

I’m scrolling on LinkedIn, just typical corporate America is kind of  LinkedIn. 100%.

That is our bread and butter. It’s our base expense to pay for premium LinkedIn to be able to message anyone. But, I mean, I think social media is huge now for sure. But it’s also it’s also part of branding. But, you can long story short, you can use Instagram and Facebook to find people.  I found paralegals on Facebook. There’s you and I are older millennials.

So  Facebook. I remember when Facebook was used just to be a dorm. You had to have a college email to get on Facebook. But now,  our parents and older generations are big on Facebook still. So there’s a Facebook group for anything.

That’s true. I’m a big Facebook group guy now, I collect baseball cards and stuff now or I used to and I’m still just, interested in what’s going on. So baseball card group, I’m in a paralegal group. Just when I get a paralegal job posted on Facebook people reply and message me and, you have to get creative to make sales to find people.

Which is it It’s challenging but also fun. Because you can you there’s so many different ways to find jobs or to make a sale, whatever industry you’re in.

Absolutely. And the other thing that kind of gives me a good point to make is, if I could give one piece of advice to someone who’s looking for a job, it would be in this is any industry, you have to network and you have to market yourself. Especially now, in corporate America sadly, there’s been a ton of layoffs in 2023. There’s, over hiring and COVID led to a lot of layoffs, in my opinion, because more remote people and just companies overextended themselves.

So there are a lot of really good people on the market now, especially in the tech world. But I know this is true in a lot of industries. And I’ve done some consulting in the recruiting world, on the internal side, as well. So I’ve seen how many people are applying to these jobs at big companies and things that, and we’re talking hundreds of applications to one job crazy.

And if you don’t know, someone, it’s really hard to get seen you, you have to be able to network and market yourself. So, part two of my advice on that would be if a recruiter reaches out to you on LinkedIn, or Facebook, Instagram, whatever, even if you’re happy in your job, talk to them, you just never know when the rug is going to get pulled out from under you through especially if you’re working at a big company, man they’re worried about their bottom line.

And as shitty as it sounds, they’re there, they’re not worried about you, and what bills you have to pay, you’re, you’re just a number to most companies.

So just take the call,  build your network, how to keep your LinkedIn profile up to date. And make friends, even if you’re not looking, you should still talk to people. Because you never know where that person is gonna end up and you might want to work at that company, you might get laid off, you might get fired.

You might hate your boss, but, it might not be now, but it might be a year from now. That’s such great sound advice. I, I relate that to the podcast to, the conversation that I have on here. , I may not have a deal or something may not come up from this conversation. But, three years down the road  Something may come up. So it’s, it’s just relationships just connecting with people.


100% I believe in that and you did not have an ulterior motive with this podcast. I know that but before we started, I was, Hey, I might be looking for Beach Condo soon. I might want to sell my house.  and I’m gonna give you an opportunity over Joe Schmoe in real estate and St. Pete just because I know who you are. So I agree with you. 100% 

I love that. So where can people get more info on Cruit Group? I’m in the sense it’s taking a minute to get past it. And then Wags and Wine.


So Cruit Goup. I mean, we have a website, just cruitgroup.com my email is Ryan@cruit group.com Wags and Wine. You can check us out on Instagram @WagsandWinebox, or Wagsandwine.com.

I know we’ve got some discount codes on Wagsandwine.com  now,  to get 50% off your first box. So definitely go check us out on there for sure.




JOIN THE LOCALS  for exclusive discounts and specials from our local business owners and stay up to date on what’s happening in Palm Harbor.

Together, we keep Palm Harbor local.

Stroll through the laid-back streets of the Palm Harbor community with this informative podcast, proudly brought to you by Donnie Hathaway with The Hathaway Group, your trusted guide and local expert in navigating the diverse and ever-changing property landscape of Palm Harbor.

Work with me + FREE Resources

Would you like help buying a home in Palm Harbor? – Buyer Consultation
Would you like help selling your house in Palm Harbor? – Seller Marketing Consultation
Download our free buyer’s guide today – Buyer’s Guide