In short
Podcast Episode Notes
Podcast Title
The Thoughtful Entrepreneur Description: A daily, commercial-free spotlight show featuring CEOs and founders of 6-9 figure B2B companies. Entrepreneurs share success stories and advice for business growth.
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Episode Title
1789 – Scaling Your Business with Steven Calascione of Success With Class
Episode Overview In this episode, host Josh Elledge converses with Steven Calascione, founder of [Success With Class](https://successwithclass.webflow.io/). Steven discusses his entrepreneurial journey, starting from being laid off during the pandemic to successfully running a property management business and transitioning to coaching other entrepreneurs.
Key Highlights of Steven's Journey
- Pandemic Catalyst: Laid off from a corporate job, Steven pivoted with his wife into property management.
- Rapid Growth: Within two years, they scaled the business to a seven-figure revenue stream through strategic marketing.
- Passion for Coaching: Realizing his passion lay in helping others, he sold the property management business to focus on mentoring through Success With Class.
Insights from His Book
- Title: [Service Business Mastery: The Blueprint to Scaling Your Startup to Seven Figures and Beyond](https://www.amazon.com/dp/B0CKQ33MB2)
- Target Audience: Service-based entrepreneurs looking to deliver exceptional service and scale their operations.
- Philosophy: Focus on over-delivering on promises and building long-term relationships to secure repeat business and referrals.
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Key Points from the Episode
- Steven's Transition:
- Shifted from corporate employment to entrepreneurship during COVID-19.
- Growth in property management sector through effective marketing strategies.
- Coaching Focus:
- Helping entrepreneurs in the real estate sector refine their sales and marketing systems.
- Customer Relationship Importance:
- Emphasis on outstanding customer service and over-delivery to create lasting client relationships.
- Market Dynamics:
- Observations on a shift towards renting due to affordability issues in the housing market.
- Growth potential in the property management sector due to increased demand for rental services.
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About Steven Calascione
- Background: Dynamic entrepreneur with a focus on helping service-based small businesses reach their first million in revenue.
- Expertise: Strategic planning, hands-on management, sales training, and leadership development.
- Podcast Host: [Service Business Success](http://open.spotify.com/show/6aimTRCxX9DliH4fjgtf9E), featuring insights and advice for entrepreneurs.
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About Success With Class
- Description: A coaching agency aimed at guiding emerging entrepreneurs through challenges in service-based industries.
- Core Principles:
- Scaling businesses effectively while maintaining exceptional service quality.
- Focus on building sustainable business models.
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Noteworthy Quotes
- “What you really want is booked appointments to get in front of clients who know, like, and trust you.”
- “We’ve lost the core principle of serving in business; it’s crucial to focus on fulfilling promises.”
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Conclusion This episode emphasizes the importance of adaptability, customer service, and strategic marketing in building a successful business. Steven Calascione's journey and insights serve as an inspiration for entrepreneurs in service industries.
For more information on Steven and his work, visit [Success With Class](https://successwithclass.webflow.io/) and check out his book on Amazon.
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Call to Action If you're interested in being featured on The Thoughtful Entrepreneur or want to connect with the community, visit [Up My Influence](https://upmyinfluence.com).
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Tags
- Entrepreneurship
- Business Growth
- Coaching
- Property Management
- Customer Service
- Marketing Strategies
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:28Hey there, thoughtful listener. million in revenue. Just head to upmyinfluence.com 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 upmyinfluence.com and click on podcast. We'd love to have you.
0:58with us right now it's steve calesoni steve you are a seven figure property management exit strategist coach uh 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 steve thank you so much for joining us 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 a great whole workshop. Ladies and gentlemen, let's get ready to rumble.
1:34I could be that guy. Exactly. Steve, go ahead and give us an overview of your work today and what you do. Yeah, absolutely. So I was an owner of property management business. I started in the middle of COVID after I was laid off from my corporate nine to five 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, 200K, let's say between the both of us to zero overnight. And 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.
2:07I 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 a really kick ass marketing and sales campaign. I grew that from zero dollars. 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.
2:40And 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 enjoy 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, and I came up with success with class. I know what I did is extraordinarily achievable and replicatable. With just the right tools, you can kind of unlock the same success I had.
3:11I know a lot of people want to get into real estate and lack the capital to get into it. So property management is a great way to get started because in essence, you can make anywhere from 8 % to 10%, 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. 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 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, but they didn't have that background of like how to get new clients in the door.
3:48And that was the real specific niche that I'm now focusing on. So what I help entrepreneurs do is particularly in the real estate sector who want to go into property management or vacational 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 service.
4:18It's just a validation of what they already know because you have such a kick-ass 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. Yeah, so maybe someone who's listening conversation right now, understand the difference between a quote unquote lead, which by the way, I don't care for that term, versus, you know, again, something, you know, that's a little bit more meaningful, intimate, you know, higher touch. Can you maybe help delineate that difference a bit more?
4:52Sure. 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 pique 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 be the no show for your 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.
5:24In my case, it's someone who's dealing with an addiction, maybe it's someone whose grandma unfortunately passed away, and they just need someone to take care of the home of the asset. So I can specifically market that to that pain point. And because you have good marketing, when that appointment, I call a discovery call comes, you know that they're coming with a great or not a great and an 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?
5:56You have the harvesting where people can go on Google type in, I need a plumber, I have a leak. And then the first plumber answers the phone, you got the job because they need to 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 that 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?
6:26That's the pain point that I can then solve for you and then automate. So that's my specific client avatar, if you will. Yeah. So talk just a bit more about the current state of the industry when it comes to property management and like what is that opportunity there? Sure. So I unfortunately think that we're headed to become a renter's nation. I think affordability is 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 the financial situation changes.
7:06Now, I don't necessarily agree with that strategy, but I think that's the reality of what's happening. And because you have a lot of millennials looking to rent where it's not the – they're hopefully not life-term tenants, typically this generation is in tune to turnkey service. So if there is – if 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. as they want to pick up the phone and handle that. And in 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, it's a three, 4 % even, why would you ever give that up on a 30-year fixed mortgage rate?
7:44Right, I know. Hold the property at that point, and now you wouldn't need to 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 up whole communities. So it's not just that idea of like, I'm gonna live in an apartment building.
8:13You have these 35 year old young professionals with a young family who wanna rent a single family home. And they're gonna stay a while in most cases. 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. We have a blueprint laid out to kind of get to the next step.
8:44But 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. 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 to Scaling Your Startup to Seven Figures and Beyond. Sorry, I was looking at an image and then the text got real tiny. But tell me more about, yeah, tell me more about the book.
9:16Congratulations on the success, by the way. 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 in 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. 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 lack of service dips.
9:51So this book is for anyone who wants to become a service-based entrepreneur or already has a service-based business. And through service, I mean, you're not really selling a widget. 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. You're a DJ. You're a property manager. It 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 is set the bar so high that you're going to over deliver on that promise.
10:20And 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 client. 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's going to take you from A to Z. I did it through my own experience of starting my own business. I've started other businesses in the past that have failed horrifically before I found success. And this is kind of like what helped me get through it.
10:51So it's a little bit of a personal memoir, if you will, as well. Yeah, yeah. So I just, I happen to be reading a book or not reading a book. I'm taking a course. I've DJed just on the side. It's just kind of a fun hobby, but I've done it professionally. I've done over a thousand hours in my lifetime. But it's funny because I'm actually taking like a club DJing 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?
11:27Yeah, absolutely. And funny enough, I actually was a DJ for a decade. Oh, my gosh. No kidding. Yeah, I did. I did mainly weddings. But so I can speak to this. Yeah, yeah, same, same. What kind of, what do you use for a deck? So I use it, it's called a DJ SX2. And it was Serato was a software platform that I was using. Oh yeah. And I've been out. I use the Pioneer DDJ 400. So yeah, and I just, you know, again, run it all off the laptop, you know, that sort of thing. So anyway, I'm sorry, Steven, go ahead. 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.
12:03So 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 you going to do bars? Are you going to do corporate events? Whatever that is, hyper-focused and double down on that in your marketing efforts. Someone goes on your website. It has to be, as soon as 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.
12:32You 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 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.
13:01the more specific you can be the greater your level of service is going to be 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 of DJs who want to be that nightclub, you know, DJ Tiesto, for example, but they also want to make side money as a wedding.
13:35And those two typically don't correlate that much. Yeah. Pick a lane, pick a lane for sure. And for a 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 a bride says, Hey, you know, I really love nineties hip hop. I'm all about run DMC and Biggie Smalls and you're playing house techno for three hours, you did the client to disservice 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.
14:18And it just becomes this reciprocity that continues and builds out. And I always advocate to make sure that if you're, say, a wedding DJ, that someone contacts you, 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. 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.
14:54So 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. Oh, I'm keeping out on it. I love it. Stephen Calasone, your website, successwithclass.com. Who needs to be going to your website? And where do folks go from here? Obviously, you know, we talked about the book.
15:23The book is Service Business Mastery, the Blueprint to Scaling Your Startup to Seven Figures and Beyond. BJ's and Beyond. It's on Amazon. It's got a 25-star ratings on it. Yeah, Stephen, where else do folks go from here? 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 book, I'm giving it basically away for free. It's 99 cents.
15:54You 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. I love it. All right, success with class. Stephen Calaschone, it's been great having you as a guest. Thank you so much for the conversation.
16:22It's my pleasure, Josh. Thank you so much.
16:29Thanks 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 upmyinfluence.com slash 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 in Facebook. I'd love even if you just stop 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.
17:13Together, 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. Thanks for listening and thank you for being a part of the Thoughtful Entrepreneur Movement.
From the publisher
In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Founder of Success With Class, Steven Calascione.
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,...

