1789 – Scaling your business with Steven Calascione of Success With Class

In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Founder of Success With Class, Steven Calascione.

Calascione wide

The pandemic has been a catalyst for change for many, and Steve's story is a testament to the resilience and adaptability required in these times. After being laid off from his corporate job in midtown Manhattan, Steve, alongside his wife, made the bold decision to pivot entirely.

They ventured into the world of property management, starting from scratch. With a robust marketing and sales campaign, they rapidly grew their business to a seven-figure revenue stream within two years.

However, Steve's aspirations didn't stop at running a successful business. He discovered a deeper passion for helping other entrepreneurs navigate the real estate sector. This realization led him to sell his thriving property management business and establish Success With Class, where he now serves as a coach and mentor to up-and-coming entrepreneurs.

Steve shared valuable insights from his book, “Service Business Mastery: The Blueprint to Scaling Your Startup to Seven Figures and Beyond.” This resource is a goldmine for service-based entrepreneurs eager to deliver exceptional service and scale their operations. Steve's philosophy centers on over-delivering on promises and fostering long-term client relationships, crucial for repeat business and referrals.

Key Points from the Episode:

  • Steve's journey from being laid off during the pandemic to starting a successful property management business
  • Transitioning to coaching and helping other entrepreneurs in the real estate sector
  • Insights into effective marketing and sales strategies for service-based businesses
  • Growth potential in the property management sector
  • Importance of outstanding customer service and effective marketing and sales strategies
  • Importance of over-delivering on promises and building long-term relationships with clients

About Steven Calascione:

Steven Calascione is a dynamic entrepreneur and coach, steering service-based small businesses towards their first million in revenue. With over a decade of varied business experiences, his approach is a blend of strategic planning, hands-on management, and fostering a growth mindset.

His expertise lies in formulating and executing strategies, leveraging his deep sales, marketing, and event production knowledge. Steven aids clients in designing profitable, scalable, and sustainable business models, focusing on refining business processes, revenue streams, and marketing tactics to thrive in ever-changing markets.

More than just a strategist, Steven enhances his clients' capabilities through sales training, leadership development, and streamlining business operations. His goal is to empower businesses to achieve success and maintain it.

Steven is also the host of the ‘Service Business Success‘ podcast, where he shares insights and interviews successful entrepreneurs, offering practical advice and motivation. As a professional speaker, he spreads his wisdom on entrepreneurship, business growth, leadership, and marketing, aiming to inspire and educate a broader audience.

About Success With Class:

Success with Class, founded by Steven Calascione, is a coaching agency that marks his proudest achievement in a career filled with entrepreneurial success. This coaching agency is Calascione's platform for guiding and inspiring emerging entrepreneurs.

Within just three years, Calascione successfully launched and grew three service-based businesses, each surpassing the million-dollar revenue mark. His mission is clear and driven by his rich experience: to ensure that the entrepreneurial journey of his clients is as exhilarating and successful as his own.

In his agency, Calascione focuses on crucial aspects of business growth, such as the importance of following up with qualified prospects to increase sales closing percentages.

He emphasizes the need for a systematic approach to follow-ups, personalization of communication, and providing value in each interaction, essential for building strong customer relationships and driving sales success.

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Links Mentioned in this Episode:

Want to learn more? Check out Success With Class website at

Check out Success With Class on LinkedIn at

Check out Steven Calascione on LinkedIn at

Check out Steven Calascione on Instagram at

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Josh (00:00:04) - Hey there, thoughtful listener. Would you like consistent and predictable sales activity with no spam and no ads? I'll teach you step by step how to do this, particularly if you're an agency owner, consultant, coach, or B2B service provider. What I teach has worked for me for more than 15 years and has helped me create more than $10 million in revenue. Just head to up my and watch my free class on how to create endless high ticket sales appointments. You can even chat with me live and I'll see and reply to your messages. Also, don't forget the thoughtful entrepreneur is always looking for guests. Go to up my and click on podcast. We'd love to have you. With us right now it's Steve. Steve, you are a seven figure property management exit strategist coach. You are also the founder of success with class. Your website is success with class. Com and you're also the author of a best selling book, Service Business Mastery The Blueprint to Scaling Your Startup to Seven Figures and Beyond.

Josh (00:01:20) - Steve, thank you so much for joining us.

Steve (00:01:22) - I really appreciate it. What are your rates? I can hire you just to give my announcements anywhere. I walk into a room because that was great. That was yeah, yeah.

Josh (00:01:30) - Ladies and gentlemen, let's get ready to rumble. I could be that guy. Exactly. Steve, go ahead and give us an overview of your work today and what you do.

Steve (00:01:38) - Yeah, absolutely. So I was an owner property management business. I started in the middle of Covid after I was laid off from my corporate 9 to 5 job. I was working in midtown Manhattan, and my wife was also laid off at the exact same time. So we went from making like 150, 200 K, let's say, between the both of us to zero overnight. And we were I was in the event business and the venue I was working in shut down permanently. So it wasn't like, let's just wait for Covid. And I got my job back. It was like, I need to figure this out immediately to pivot and make a move.

Steve (00:02:07) - I was already into real estate. I had owned a few investment properties and I really enjoyed the hospitality sector, so I wanted to merge my hospitality knowledge and my love for real estate. And I came up with a property management idea and lo and behold, what are really kick ass marketing and sales campaign. I grew that from $0 and within two years we were rocking seven figures a year annually and grow sales. And I kind of catapulted that. I realized pretty early on that my passion wasn't really dealing with tenants or guests checking into an Airbnb. My passion was more in helping other entrepreneurs, and it really crystallized for me when I unfortunately lost my mother a few months ago and I was like, you know, I really want to lead a purpose driven life and not just be about the dollar amounts that I'm making or, you know, expansion. I want to do something I truly enjoyed on a day to day basis. I ended up selling that business. I made a heck of a great profit, and I took some time to think about what I really wanted to do.

Steve (00:03:01) - And I came up with success with class. I know what I did is extraordinarily achievable and replicable. With just the right tools. You can kind of unlock the same success I had. I know a lot of people want to get into real estate and lack the capital to get into it. Property management is a great way to get started because in essence, you can make anywhere from 8 to 10 or 11% of the gross rent, with no really upfront capital risk on your end other than the business side of it keeping the lights on, you know the rent comes in, you take a portion of it, you handle all the tenant issues and maintenance complaints, and it's a really scalable way to trajectory. And I noticed the property management sector in particular was a little bit stagnated when it came to technology and sales. They tend to be really good operators. Um, but they didn't have that background of like how to get new clients in the door. And that was the real specific niche that I'm now focusing on.

Steve (00:03:52) - So what I help entrepreneurs do, particularly in the real estate sector and who want to go into property management or vacation rental management, is get their sales and marketing system and pipelines set up to be effective. Because most people have this idea that I just need leads coming in the door. When you don't really need leads, what you need is booked appointments to actually get in front of clients who know, like, and trust you. And then from there, it's not really a sale. You're not twisting someone's arm to buy your your service. It's just a validation of of what they already know. Because you have such a kickass marketing campaign and it's very teachable. Josh, I'm sure you have. I was mentioned before we started here that you have an amazing marketing side of your own business, so I'm sure you can appreciate some of the values there.

Josh (00:04:33) - Yeah, so maybe someone just listed a conversation right now. Understand the difference between a quote unquote lead, which by the way, I don't care for that term.

Josh (00:04:42) - Yeah. This is you know, again, something you know, that's it's a little bit more meaningful, intimate, you know, a higher touch. Can you maybe help delineate that difference a bit more?

Steve (00:04:52) - Sure. A lead is someone who potentially was just scrolling through Facebook or, you know, they're on social media and they see something that might peg their interest and they just kind of quickly say, yeah, I want to learn more. They're half engaged. They didn't do any research in your company, really. And they either no show for you're an appointment or there's someone who doesn't have the budget or you're not really serving what their specific problem is. What you really want is someone who takes that value and has a specific problem, because your marketing has been so good that you honed in on what their issue is. In my case, it's someone who is dealing with an eviction. Maybe it's someone whose grandma unfortunately passed away, and they just need someone to take care of the home of the asset.

Steve (00:05:32) - So I can specifically market that to that pain point. And because you have good marketing, when that appointment, I call it discovery call comes, you know, that they're coming with a great, um, or not a great and unfortunate issue that they need resolved. And you are the solution. So you're providing that answer that they seek. And the way you do that is really having that effective marketing campaign. And there's two different types of companies out there, right. You have the harvesting where people can go on. Google type in. I need a plumber. I have a leak. And then the first plumber is is the phone. You got the job because they need the shut off the water. The pain point is extraordinarily high. But in the instance of service, in some cases they might not know they have an issue until it is revealed to them. And that's what really makes it. Key is for my purposes as a business coach. Now I'm revealing that. Are you stuck in a hamster wheel? Do you feel like you're not able to grow your property as a business because you're too engaged in the operations, and you have time to respond to those leads? That's the pain point that I can then solve for you in an automate.

Steve (00:06:30) - So that's my specific client avatar, if you will.

Josh (00:06:33) - Yeah. So talk just a bit more about the current state of the industry when it comes to property management and kind of like what is that opportunity there?

Steve (00:06:43) - Sure. So I unfortunately think that we're headed to become a renters nation. I think affordability as an all time low. I think that for first time homebuyers, the millennial generation, which is my generation, are finding it harder than ever to make that first step and buy their own property. And a lot of these people are opting to rent until either interest rates change or or the financial situation changes. Now, I don't necessarily agree with that strategy, but I think that's a reality of what's happening. And because you have a lot of millennials looking to rent where it's not the they're not hopefully not life term tenants, typically this this generation is in tune to turnkey service. So if there is, you know, a painting falls off the wall. They want someone to rehang it. If there's a slight leak, they're not going to fix themselves.

Steve (00:07:28) - They want to pick up the phone and and handle that and and concurrence with this. You have the baby boomer generation. That is if they're opting not to sell because a lot of people now, if they locked in a low interest rate, I'd say three 4% even. Why would you ever give that up on a 30 year fixed mortgage rate? Right?

Josh (00:07:44) - I know, hold.

Steve (00:07:45) - The property at that point and now you wouldn't need the rent. So you have the demand coming from both sides now. And I see this not changing for a decade at least. And with that need is a lot of people who don't know how to handle that tenant relationship dialogue and know how to deliver outstanding customer service. So I see the property management sector growing, and you see this with companies like Blackrock who are buying up these single family homes and then renting them out. They're buying a whole communities. So it's not just that idea of like, I'm going to live in an apartment building. You have these 35 year old young professionals with a young family who want to rent a single family home, and they're going to stay a while for in most cases.

Steve (00:08:21) - So if you can deliver outstanding service, your business will scale like wildfire. And again, it's not that difficult. You have a problem that someone needs solved. So the scalability approach is there. Obviously you need the right systems in place. You need to have a really great back end office that can handle maintenance. You need to have great contractors. You know, that's something that we could all that's very again, very teachable. And we have a blueprint laid out to kind of get to that next step. But again, it's not really rocket science to scale this business. And I see this happening across the country. It's not specific to say just Phoenix or New York City. It's happening from west to East Coast for sure.

Josh (00:08:55) - Yeah. So, Stephen, tell me about your book in particular, who should be reading this book and who should we be recommending this book to as well? It's called Service Business Mastery The Blueprint. Oh, and then the image. I was like, the blueprint is scaling your startup to seven figures and beyond.

Josh (00:09:10) - Sorry, I was looking at an image and then the text got real tiny. So but but tell me more about. Yeah, tell me more about the book. Congratulations on success, by the way.

Steve (00:09:18) - I appreciate that. Yeah. So I found the need when it comes to the level of service. Right. And this kind of takes me back to the word samurai. And I know this doesn't make any sense initially, but I'll unpack it. So the word samurai in the Japanese language is translated to serve. They would serve their master at all costs. And I think we've lost that. And across the board where we just get, you know, great sales tactics, get the client and the fulfillment drops off the face of the earth. And I'm sure anyone listening has experienced this, where someone's super responsive. And then as soon as they get paid, they're gone or their their lack of service dips. So this book is for anyone who wants to become a service based entrepreneur or already has a service based business.

Steve (00:09:56) - And through service, I mean, you're not really selling a widget. You're not. You don't have a Shopify or an Amazon account. You're selling an in-person thing that's tangible. You're a photographer, you're a videographer, your DJ, your property manager takes place in person. And this builds upon the foundation of how to get clients and more importantly, how to fulfill the promises that you've delivered. And what we want to do was set the bar so high that you're going to over deliver on that promise. And this book kind of walks you through, step by step of how to engage a client, how to make them into a really long term relationship, and then ultimately how to get repeat business from that same clients and more importantly, how to get referrals, because that's the golden ticket as opposed to spending thousands on your ad campaigns. So it's really, again, that blueprint that that's going to take you from A to Z. And I did it through my own experience of starting my own business. I started other business in the past that had failed horrifically before I found success.

Steve (00:10:48) - And this is kind of like what helped me get through it. So it's a little bit of a personal memoir, if you will as well.

Josh (00:10:54) - Yeah, yeah. So I just I happen to be reading a book or not reading book. I'm taking a course I've, I've made just on the side. It's just kind of a fun hobby. But I've done it professionally. I've done over 1000 hours in my lifetime. But it's funny because I'm actually taking like a club deejaying course right now, and I'm like, I'm like, I got to go back and like learn some of these more advanced DJ tricks. But so I'm listening to podcasts on the topic. So how would be so for example, like let's say a DJ reads your book, how might it look if they were to implement some of the practices that you discuss in your book?

Steve (00:11:27) - Yeah, absolutely. And funnily enough, I actually was a DJ for a decade.

Josh (00:11:30) - Oh my gosh, no kidding.

Steve (00:11:31) - Yeah, I did, I did.

Steve (00:11:32) - Mainly weddings, but. So I can speak to this. Yeah. Yeah. Same same.

Josh (00:11:36) - Same what? What kind of. What do you use for a deck.

Steve (00:11:39) - So I use it. It's called a DJ two and it was Serato was a software platform that I was using.

Josh (00:11:45) - Oh, yeah.

Steve (00:11:45) - With um, and I.

Josh (00:11:47) - I use the, the pioneer DJ 400, so. Yeah. And I just, you know, again, run it all off the laptop, you know, that sort of thing. So anyway. Sorry Stephen. Go ahead.

Steve (00:11:57) - No no no. Yeah. No problem. So you're a DJ, right? I would say focus really specifically on what client base you're serving. So are you going to be the bar mitzvah expert? Are you going to be the wedding person? Are you going to be the nightclub DJ? Are going to do bars? Are you going to do corporate events, whatever that is hyper focused, and double down on that and your marketing efforts.

Steve (00:12:16) - Someone goes.

Josh (00:12:17) - Brilliant.

Steve (00:12:18) - Yeah, you has to be. As soon as they someone goes on your website, it is immediately apparent who your client base is. And some people are like, oh, I don't want to lose the business of a bar mitzvah. It's okay, that's not your client base. If that's not the need you want to serve and that's not fulfilling to you, you want to be the number one wedding DJ, for example, in your state or your county. And if you can really extrapolate that and hone in on what a bride and groom wants, and that's your marketing of like, hey, let's really focus on your first dance. Let's really, really, how important is your father daughter dance? Do you want your your wedding to be a nightclub? Do you like country music? And the more you can really, really cater with specific questions, the better delivery you're going to have at this event. And this can be a photographer. Like if you want to be a wedding photographer, whoever it happens to be, the more specific you can be, the greater your level of service is going to be.

Steve (00:13:05) - Because now the expectation is, I understand what you need, I understand what you want, and this is my delivery. And oh, by the way, here's all my client testimonials I'm going to integrate that have these glowing reviews at the end of the night, where they're almost in tears because they've had such an emotional connection to the music in this instance. So the more you can be that specific, the better it is going to be at the end product. And I can't tell you how many times I've encountered DJs who want to be that nightclub. You know, Deejay Tiesto, for example. But they also want to make side money as a wedding, and those two typically don't correlate that much.

Josh (00:13:37) - Yeah, pick a lane, pick a lane for sure.

Steve (00:13:40) - And for DJ purposes, you don't want the music to be about how cool you are. You know, you don't want to be the coolest kid on the block. You want to cater to that event. Like if bride says, hey, you know, I really love 90s hip hop.

Steve (00:13:51) - I'm all about Run-DMC and Biggie Smalls, and you're playing house techno for three hours. You did it. The client did the service because you wanted to hear the music. You're not paying attention enough. So that's we go into a little bit on the book as well about really, really focusing on on that, those key points. Because if you can deliver an outstanding level of service or someone is in tears at the end of it, in a way you've done your job and then you can sit back and I promise you, people who are at that event are going to come up to you to book their events. And it just becomes this reciprocity that continues and builds out. And I always advocate to make sure that if you know, you're, say, a wedding DJ that someone contacts you, sends, submits a form for more information. All of your marketing emails leading up to that appointment or discovery call conveys that you are a wedding DJ and it's not selling yourself. It's saying, hey, here's the five great tips to make your wedding day spectacular.

Steve (00:14:43) - Or here's the top five songs or father daughter dances, whatever it is. Because what your industry insights are, your expertise you take for granted, this is someone's hopefully first marriage. So for them, it's going to be like they're new to this. They don't really know the process as well. So if you can kind of hold their hand and guide them through it, you're not doing a sale at that point. You're basically it's just a validation of all the marketing that came right before that appointment setting. So that's the long winded answer to your question, Josh, of how to really kill it.

Josh (00:15:12) - And oh, I'm getting out on it, I love it. Stephen. Tony, your website success with Who needs to be going your website and where do folks go from here? Obviously, you know, we talked about the book. The book is service business mastery. The blueprint is scaling your startup to seven figures and beyond, BJ's and beyond. Go get this book. It's on Amazon.

Josh (00:15:31) - Uh, it's got a 25 star ratings on it. Yeah. Stephen, where else do folks go from here?

Steve (00:15:37) - Yeah, absolutely. So if you want to learn more, I'm offering free consultation on your service business, ideally in the real estate sector. No obligation, of course. We just will unpack what's underneath the hood and see if we can potentially help each other out. Also, if you're ever interested in actually getting the ebook, I'm giving it basically away for free. It's $0.99. You can go on my website success with class. Get the Kindle version. It's the cheapest I can. Made it. I hope you find a tremendous amount of value at that price point. And I'm also a paid speaker, so I've done events, particularly in the hospitality industry. I'm actually going to Barcelona very soon to give a speech. So if you ever have a corporate event and you want to learn about service and sales mastery, happy to indulge in that conversation as well.

Josh (00:16:15) - I love it. All right.

Josh (00:16:16) - Success with class Stephen. It's been great having you as a guest. Thank you so much for the conversation.

Steve (00:16:22) - It's my pleasure. Josh, thank you so much.

Josh (00:16:29) - Thanks for listening to the Thoughtful Entrepreneur show. If you are a thoughtful business owner or professional who would like to be on this daily program, please visit up my influence common Guest. If you're a listener, I'd love to shout out your business to our whole audience for free. You can do that by leaving a review on Apple Podcasts or join our Listener Facebook group. Just search for the Thoughtful Entrepreneur and Facebook. I'd love, even if you just stopped by to say hi, I'd love to meet you. We believe that every person has a message that can positively impact the world. We love our community who listens and shares our program every day. Together, we are empowering one another as thoughtful entrepreneurs. Hit subscribe so that tomorrow morning. That's right. Seven days a week you are going to be inspired and motivated to succeed. I promise to bring positivity and inspiration to you for around 15 minutes each day.

Josh (00:17:34) - Thanks for listening and thank you for being a part of the Thoughtful Entrepreneur movement.

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