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Every investor wants to soar, but according to Kyle Connor from DIY Wholesaling, sometimes speed isn’t what is most important. Sometimes you should look to progress slowly. Kyle emphasizes that it’s okay to slow down and build the structure so you can move faster in the long run. As an entrepreneur whose aim is to help both new and tenured investors scale their real estate ventures, Kyle shares how DIY Wholesaling uses the power of systems, data, and how it provides apt VAs to make their goal happen. Watch the full episode now!

About Kyle Connor

Kyle is 30 years old and started his professional career working in cyber security software sales, helping to build out Inside Sales Teams for hyper growth startup companies. After joining a number of mastermind groups, he started wholesaling real estate in Nov. 2019 with his brother & business partner Chris. It was after a few years of building a successful wholesaling company that he decided to partner up with another 7 figure wholesaler out of Ohio, and launch their business DIY Wholesaling to provide lead generation, virtual assistant, data management, & systems building services to new and tenured real estate investors across the US. Kyle now resides in Miami, FL and is on a mission to help real estate business owners scale their operations to 6 & 7 figure heights through the power of outbound sales marketing, data, and systems.

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Slow Down and Scale Responsibly – with Kyle Connor

Hey everybody. It’s Jordan Fleming here with another weekly episode of That Real Estate Tech Guy. I am delighted to say that my co-pilot for today is Kyle Connor from DIY Wholesaling. Kyle, welcome to the podcast. Why don’t you just introduce yourself and DIY Wholesaling?

Yeah, Jordan, I’m happy to be here, man. I’ve been a long time user of smrtPhone. So it’s been a pleasure to be here today. Yeah, Kyle Connor, so I started wholesaling back in early 2020. Funny enough, I joined Tiffany and Josh’s mentorship program. That’s how we were first introduced to Podio. I know they’re big advocates of you guys and smrtPhone. And so, through that, I met another wholesaler within that business. He was a seven-figure wholesaler in Columbus, Ohio, and found a common problem with a lot of the investors that we were working with. And a big thing that we learned with Tiffany and Josh’s program is the power of systems and having processes in place and what that can do to help scale your real estate business. And so we were hearing a lot of problems from investors when we were at networking events, and they just did not understand the systems to do direct-to-seller marketing. And they also couldn’t find outbound or VA talent or good cold-calling towns to do their outbound lead gen. Thus, we created a sort of business in a box with the power of lead generation systems and data management, which is where DIY wholesaling was born. And that’s been sort of our baby since we introduced it in April 2021.

So you obviously started out as an investor yourself. Do you have a technology background? I mean, obviously, going from being an investor to scaling a technology product is quite a different sort of field to play in. So how did that come about?

I started my professional career out of college working for cybersecurity software companies. So I worked in inside sales, and working at Hypergrowth, carrying a bag and closing deals, is where I learned sales development and really understood how to use power dialer, Salesforce, different marketing techniques, leveraging the power of software and tools to help build my software sales business. And so I took that confidence that I was getting working at HyperGrowth startups and started doing what it took to build a business on a very small scale, right on an inside sales level. And that’s what gave me the confidence to say, Hey, you know, this is very relatable to building a wholesaling business, and real estate was just what I had to start to figure out its core to the understanding of real estate, and how I could apply my experience in software sales to the real estate industry. And that’s really how I started to learn the power of sales and operations.

You were talking about lead gen combined with CRM capabilities. Lead gen is obviously a critically important thing for people, particularly if they’re getting off the ground. There are 50,000 ways you can spin the bottle on this one. So tell me a bit about the lead gen part of the business.

Like you said, there are a lot of ways to turn off-market leads into closed deals. That’s the beauty of wholesaling and real estate. It’s not black and white. And so, you know, what stuck well for us, what I was comfortable with was understanding how to do outbound sales. We typically leveraged the power of cold calling and SMS marketing, with a little bit of direct mail mixed in between. And so, again, we’ve built a very solid acquisition engine. And that’s been the core foundation of outsourcing cold calling. So we hire cold callers and manage them in-house, leveraging the combined team of CallTools that we use for our power dialer as well as RooR, which is our outbound SMS marketing product. And that was our bread and butter for a while. And that’s what we’ve been most comfortable with. So that’s been sort of our focus. We wanted to get direct to seller. We wanted to make sure we were cutting out JV partners, although we can talk about the power of JV. And of course, we wanted to make sure that we were building a solid foundation of pipeline and leads that were all direct to seller, and we felt that SMS and cold calling were the best ways to do that.

Is that something that you built out for your own business first and then rolled into the product package? Is that how you saw it working?

We started that with our own business, and we were able to scale to a six-figure wholesale business my first year with my brother as my business partner, and we did that part-time. And then that’s where we met our business partners for DIY Wholesaling, Josh out of Ohio, and Tiffany and Josh. So we’re like, Man, you’ve built a seven-figure business. You’re abusing the power of systems and outbound lead gen, and we’re doing something similar. Let’s package this up, and again, put this business in a box. And let’s bring this to clients and really be an extension of their business. And that’s really again, what we saw as far as value add to the marketplace is that not a lot of people understood how to find good cold calling talent, how to build lead gen funnels for themselves, outbound lead gen funnels, or even how to build systems that all sort of integrated together. And that’s what we’re providing to our clients now.

You also mentioned building a very robust acquisition tool. In your opinion, what do you think goes into making a robust acquisition platform? 

First and foremost, I think you need to invest if you’re going to be doing cold calling. And if that’s going to be a foundational piece of your lead gen, you’ve got to make sure you’re investing, and whoever is going to be doing that cold calling, or if you decide to do that for yourself, a good first step is getting a power dialer. That’s what really changed the game for us—getting a power dialer and really getting to do volume and consistency in our marketing. That’s a common theme, I think. If we’re going to bucket everything, I’ll go into the inner workings of it in a second. Being able to have consistency in your lead gen is going to make you successful in any market. So what allows you to do that? It’s having the right people and systems in place to do that at scale. And so what I see a lot of people doing is getting a power dialer, throwing a cold call around there, and then wondering why their leads aren’t coming in or why they’re not getting or generating quality leads. And a lot of that goes to investing in the team and your callers. If you’re not going to be doing the cold calling yourself, you’re going to be outsourcing that, partnering with a third-party group, or managing that in-house. You need to invest in them as if they were your domestic employees. I see a lot of people make that mistake by not continuing to train and invest in their cold-calling talent because that’s what’s going to give you quality leads in any market that you’re dealing with. And so I think I hit on a few points there. But I think that was definitely a big piece is investing in whoever is going to be doing the actual tip of the spear of your marketing and making sure they’re trained and equipped. And then having something like a power dialer or SMS marketing to allow you to do that at scale and do that consistently enough. That’s going to make you successful in outbound lead gen for sure.

Cold calling is not easy, and it can be soul-crushing. So with your cold calling structure, you bring them in-house, and then you hire them out. Is that how it works?

Yeah, we hire them. We have a couple of pockets of areas where we find really good talent. Egypt and Latin American countries are predominantly where we find our talent. And we do that on purpose. There are a lot of businesses with big call centers, Vodafone, AT&T, Amazon—you’ve got big corporations that are putting their headquarters in call centers. And so we find direct talent out there through different funnels on Facebook and other avenues. And then we manage them and hire them in-house because they want me to work for a smaller company. They want to feel like they’re an extension of the business, not a cog in the wheel. That’s what I hear often. And so we’re able to source really good talent in those pockets. And then we manage them in-house. We have a full staff for quality assurance. So that’s really key. If you’re going to build out a call center, do it in-house. You know, make sure you have somebody, if you’re not going to do it yourself, who’s going to be monitoring the quality of their lead gen and the delivery of their day-to-day. And then we have an acquisitions manager who helps to train them on different exit strategies, objection handling, and the real blocking and tackling of the delivery of the role. Whether you have someone in a support role or a quality assurance role that helps to monitor that and track their KPIs and make sure that they’re just giving positive feedback or constructive feedback, rather, on how they’re doing on the calls, then yes, that’s now the lead generation piece. We have a call team that helps fuel the lead gen for our clients in my own business now, as well.

You mentioned the quality assurance element of cold calls as well. You mentioned things like objections or handling different difficult questions. If you were thinking about training for VA around things like active listening, difficult conversations, objections, et cetera, what do you think is a good approach? Is that something you want to reinforce weekly or monthly? What's your take on that?

There are two things that we do. We do consistent training each week with my brother, who handles my acquisitions team in my wholesaling business, and then the acquisitions leader, who handles the team for DIY. And so we do at least two trainings a week with different members that are in the leadership role. And a lot of that is recognizing the common objections that we're getting that week because you're seeing the market changing a lot. Where it used to be, it's hard to find a motivated seller. Now everyone's a motivated seller. Now it's okay, how do we differentiate between a motivated seller and someone that's actually going to come to the closing table and not waste our time and actually have the key indicators that we'll talk about of wanting to actually sell their property to an investor, agent, broker, or wholesaler? And so, we do consistent training each week because the market changes very quickly and new objections come up every single week. And then what we like to do is we have scorecards, a QI scorecard. We actually have a free one on our website, if anyone wants to check it out. It basically helps us look at agents that are underperforming. We've systematized that, and if they need some additional help, then we'll do one on one sessions. With them, we used to do more one-on-one sessions, and as you know, your calendar can fill up pretty quickly. And now it's just a waste of time. So as the team gets bigger, it's really hard for our leadership team to be able to give that type of TLC. So we had to try to find ways to obviously have our group training on new things that are there we needed to adjust in our delivery of the role. And then we have to provide constructive feedback only if it justifies it. If you know how your scorecards, are low numbers, let's sit down and have a one-on-one. So and then we'll go through common themes in team meetings, like, Hey, guys, this isn't to embarrass you or anything, but this is to show common themes that we're seeing amongst the team to help fix.

And I've found historically that most of the teams really enjoy that as well. One of the structures that I've always implemented and that I've implemented in smrtPhone as well for certain teams is that every week, or every two weeks maximum, I like to do it every week, picking three good conversations and three bad ones. That's a structure I've found hugely successful. People engage in that structure.

I was gonna ask you, Jordan. You talk about active listening. That's a really good one. Sometimes regurgitating some of the things that the seller saying it's really helpful in qualifying. What are some of the metrics that you train your team on? What are some things to look for? I know, it's different.

We were a slightly interesting case because my team is smrtPhone. We don't really have sales in that traditional sense. But quality assurance comes into its own, from my point of view, at the support level, where there are metrics. The only metrics I really care about are how quickly we responded to someone. I've set the bar that, at all times, we should be responding within two minutes to every inquiry. So far, we're averaging around a minute and a half, which is great. But to me, it's time to respond. And then there's the quality control, because how long does something take you in sales? A sale conversation can go quickly. It can go quickly, or it could take a long time. It depends on the person's mood. It depends on whether they like talking, and that depends on all sorts of things. So just valuing the length of the conversation is not necessarily telling you anything. You said the question is, How fast and what was the outcome? Those are the things that matter to me.

Definitely gonna take those notes. Because we are now a newer business, our efforts were outbound sales and new client acquisitions. Now, it's like, Okay, we need to build out a support and client retention program. We need to make sure we are building that side of customer success. And so that's the next iteration of what we're looking into now to have those measures. So I'm gonna make notes of those for sure.

If someone's taken the time to contact you, you jump on that ship, and you jump on it quickly. And you don't let go until they tell you to go away. If we think about the cold calling lead gen and the CRM pieces to your puzzle, at what stage of an investor's lifecycle do you think they'd be looking at or be able to start looking at a system like yours that has such a large lead gen part of it as well?

What you just said is exactly what I try to tell my clients when they come on board. This is why you're successful with us. And this is what's gonna shoot you in the foot and waste your own money, it's you not following up in a timely fashion on the leads that we're generating. It's as simple as that. And so you talk about answering your question about tenure. So we have all that, and that's an interesting thing because we've got such a unique client persona. Right now we have brand new wholesalers and one-person shops, and we also have teams that have 500 units in southern Florida with full acquisition dispositions. And so the cool thing about it is that it's a framework where we dial things up and down depending on the amount of data and marketing budget you have per month to really target. And so we can sort of tailor our marketing strategies. The CRM gives you the foundation. It's a custom Podio version. smrtPhone is what we give to every single client. And that's a part of our custom CRM. And that helps teams of all shapes and sizes, no matter if for 1, 2, 3 man shop or a woman shop versus a fully scaled team. The difference is, and where we throw things up and down, the amount of money they have to spend on the volume of leads you're looking to target and the number of marketing channels they're looking to use because that's where your costs really go out.

You said you're using CallTools and RooR for texting as well. Where do you start doing book elements around that? I think sometimes people get a bit nervous when they're getting off the ground with those sorts of book activities. What do you think? Would you know what's good? What would you say to someone who's coming to you and wants to get started but is hesitant and unsure?

I personally like cold calling, especially if you're new. I love cold calling and SMS because it's the lowest overhead to reach as many people at scale to get a yes or no as quickly as possible. And you know, with direct mail, if you want to do it, it's a great form, but you have to have a lot of money. And you're also not going to get to that yes or no much quicker. It's a very reactive form of marketing. And you've got to do it consistently enough so that people will follow up with you. So for someone who's new, I like cold calling as a first step. Because with the power of the power dialer, if you can't afford to outsource or get someone in-house or someone else to do that for you, at least you can do a high enough volume that you're going to be successful in generating leads, and you just pay for the software for the power dialer and put yourself on there. And then budget enough so that you can outsource that focus to other business activities. And so I really liked that form of marketing to start. It also helps you if you're new. Again, you can't train someone if you haven't done it yourself. So if you're a brand new wholesaler and maybe you haven't had a background in sales, I did have a background in sales. So it helped me be confident being on the phone. I had to learn real estate. But if you're brand new to this whole industry, do it yourself before you can go and hire someone else to train them, because you're not going to be able to train them appropriately. So I think that's really, really key. And that would be your first step. And then just think in the back of your mind, Okay, you're gonna hate it, but you're gonna work your ass off, so you can get out of it and make some money, and then you're gonna be able to train them confidently.

There’s something that we hate to do. So treat yourself as an employee. Take yourself out of the business owner's hat for a moment. And then it becomes less of a thing I don't want to do. Everybody should be starting out, doing cold calling, so that they can understand what it's like and what it's all about.

Agreed. And my last point on that is if you want most people to do this so they can build a company and a team, and I think one thing that helps me out a lot when I'm leading a team is I tell them, Guys, I cold call for nine straight months before I ever kill a gun in a closing role. And then I cold called at the start of this business, and it still does cold calling in my wholesaling. So I use that and I'll get on calls, sometimes get on and we'll battle just to dust the headset off and still get it. But I think it's good because you're able to lead if that's your real goal is to build a business which most people use when they get into this. You're going to be a much better leader, and your team's going to respect you more for it because they know that you went through it as well.

You're now scaling this business as a technology business. You've got your wholesaling business, your real estate business as well. What do you think from a mindset point of view has changed for you as you think about scaling your businesses versus grinding your businesses? If you're now thinking of scaling a technology business, do you feel like anything has been made clear to you or that your mindset has had to shift slightly when you get into scaling mode?

I think the biggest theme for this year for me is slow down so you can go faster. And what I mean by that is that I was a very impatient person. And probably most people in sales RMP. So the difference between when I transitioned to this more service-based model and there are ways to systematize this business with the power of the software and tools we're using. I was humbled this year by going too fast and trying to get too many clients and doing too many new client acquisitions. And what I've realized is needing to basically slow down and scale responsibly. And also make sure I'm leveraging a lot of these technologies that are integrated, that we have internally, making sure I'm using the most that I can out of them. Because that's slowing down, and taking that time is going to allow me to avoid bottlenecks. Being able to go a lot faster. In the long run, you might sacrifice a couple of months of revenue that you're missing out on, but you're going to be able to grow so much faster because of it. And I really learned that lesson the hard way this year. And I was humbled by that.

I and anybody out there thinking of starting out with either a CRM or some other management tool like that, think this is a perfect bit of advice. If you slow down and take the time to thoroughly understand and build a structure, you will fly. If you try and run so fast, if all you want to do is run, you're just gonna be running around like a headless chicken. And that particularly applies to technology like yours.

And then you're fixing the plane while you're flying it. And that's exactly what I've been doing a lot this year. And that's not fun. I'll tell you. So build your foundation bit by bit, and you'll be better off in the long run. 

That Real Estate Tech Guy Fast Five. 

  1. What feature of your technology do you think has the biggest impact on your customers’ businesses?
    So it's going to be a combination. If you will, Podio and smrtPhone have been the best for our clients experiences. The conjoined two. If we're talking about features, Podio's ability to integrate with all of the rest of the technologies that are in our service. And then the smrtPhones ability to help with the drip campaigns, auto follow-ups, click to call. So how it helps bolster what we're doing with Podio being the core CRM?
  2. What is the biggest mistake people make in your technology area?
    The biggest thing I see people make mistakes on is using power dialers as set it and forget it technology. There's science and stuff that you have to continue to monitor when you're implementing a power dialer. And I don't know if you want more detail on that. I know you've got to be quick. But I would just say make sure you're constantly paying attention to your power dialer, and things like abandoned rate, wait time, ghost calls, drop calls, and connectivity rate. There's a science to it. So don't just set it and forget it.
  3. What is your best advice for someone who's starting out and wants to integrate a CRM like yours into their business?
    We had a common problem we provide the entire operation from lead generation data and systems. We need the clients to do the bulk of the part and make sure that they are following up on their leads in a timely fashion. And so the best advice that I can give to anyone that's looking into our Integrated Technologies in our service, make sure that you are diligent and aggressive in your follow-ups because that's what it's going to take to be successful in today's market.
  4. What's one thing you wish everyone knew about DIY wholesaling?
    I wish they knew how much time, headaches, and energy we were taking out of their day-to-day due to some of the back-end work that we're doing with systems and sort of the whole operation. Suitable lead gen systems and data are a very broad topic. It is literally doing all the heavy lifting for our clients. So I really want people to understand when they talk to us, and I'll do a good job of that. My sales pitch is to make them understand how much time and energy goes into the IT side of the house and the operational side of the house so they can focus on doing their deals.
  5. If someone's just starting out as a real estate investor, what are three bits of technology that you would recommend they bring on first?Power dialer, Podio, and smrtPhone. You're going to be in a really good position if you get those three and set up that foundation for your business.

How to reach Kyle

You can follow us at DIY Wholesaling as well as visit us at www.DIYWholesaling.com. You can book a call with us for free consultation. We're also offering a discount for all the podcast listeners 15% off discount for anyone that comes from your team here.

Well, listen, guys, you can go to thatrealestatetechguy.com. And all those links that were just shared by Kyle are going to be there. Please go take a look. And head over to DIY Wholesaling. I really encourage everybody to take a look and take advantage because you've got not only the opportunity to get up to a potential discount here but also someone with a lot of expertise that you can leverage. And that's worth its weight in gold. Make sure you share the podcast across everything you're supposed to do. Everybody knows what they're supposed to do. So do it click the Share, click the like, review. It really does spread the word and the gospel cow. It's been an absolute pleasure. Thank you so much for being on the podcast today.