From Broadway Producer To Creative Agency Owner, With Tyler Mount

Authenticity is the heartbeat of successful marketing – embrace who you are, not who you think you should be. In this episode, we have Tyler Mount, the Founder and CEO of Henry Street Creative, to share the glitz and glamour of Broadway to the forefront of the digital marketing landscape. Learn the power of an authentic voice, the art of effective leadership, building viral sensations, and more. Tune in now! 

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcast/tyler-mount

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From Broadway Producer To Creative Agency Owner, With Tyler Mount

Founder And CEO Of Henry Street Creative

My guest is Tyler Mount. As a leading expert in real estate branding and marketing, Tyler has served as a consultant to nearly 1,000 agents spanning fourteen countries worldwide. His experience spans brand development for residential agents, national brokerages, and commercial brokers in addition to new development portfolios valued at over $7 billion.

Tyler is also an industry-leading branding and digital strategy expert and the Owner of Henry Street Creative, an agency that specializes in brand design, content creation, and web development for some of the most esteemed industry professionals. In this capacity, Tyler and his team have partnered with a broad range of companies and individuals.

Tyler’s career has been profiled in dozens of reputable publications, including the New York Times, Ford Magazine, Medium, and Out Magazine. He has also served as a keynote speaker for marketing and real estate conferences across the country. His non-traditional direct approach empowers agents and business owners to take control of their businesses and build empires. He works and lives in New York City. Tyler, welcome. Thanks for doing the show with me.

Thanks so much for having me.

You run a creative agency. Tell us about it.

I am the Founder and CEO of a creative agency in the United States called Henry Street Creative based out of New York City. Our job is to bring first tier consultancy and first tier media assets to individuals around the country. Specifically in the real estate, financial, health and entertainment sectors.

I know you were doing a bunch of things on Broadway, in the theater industry and in videography. How did you decide to open your own agency? When did you start it?

My answer is so similar to so many other people’s answers, which is this was not my plan. It happened by accident. The beginning of my career was rooted almost entirely in Broadway, the Arts and Entertainment. That’s what I went to school for. That’s what I pursued professionally and in New York City for a very long time.

I was fortunate enough to find success there as a stage manager on Broadway. From there, as a content creator then as a producer. From there, as you probably know, the arts isn’t known for a lucrative career. It’s not known for making a lot of money. I had to mitigate at what point is my passion going to, at my own hands, supersede my ability to, for lack of a better term, pay rent here in one of the most expensive cities on Earth.

My experience to date, at that point, did center around content creation, branding, and marketing. I was fortunate enough to work at Playbill, which is the Broadway legacy brand in New York City. That gave me my legs in terms of my ability to work in corporate America. Most importantly, in the digital marketing space and branding space.

From there, I went to multiple corporate jobs from entertainment to real estate. Right around 2020, when this COVID thing was happening. As no one wanted to buy office space in New York City, who would? Consequently, and as a result of that, I was laid off. I had a few freelance clients that turned into a few more freelance clients, which turned into a successful roster. That’s ultimately how Henry Street Creative came to be. It was an accident. It was a byproduct of necessity meeting industry need at the time. We’ve been going strong for the few years.

You mentioned some of the industries that you worked with a minute ago. Do you do the full range of digital and traditional marketing activities or do you focus on particular pieces?

We have our hand in most all aspects of the marketing ecosystem. Our primary focus is digital marketing, specifically that asset creation. What I have found in my career is people, let’s say, know they need to be on social or need a website or potentially they need a logo. The issue then becomes, who do I go to and trust them with this exercise? That’s what we focus on.

I work a lot with individuals. We’re talking about independent and individual salespeople. Think real estate, people who are CEOs, or tech startups. That space where we can move the needle quite nimbly and quickly, versus working exclusively with Fortune 500 companies with a lot of red tape that we typically have to mitigate.

What’s the typical process look like when you engage with one of your clients?

We start with your traditional discovery. Everyone’s needs are unique and most importantly, the nuance within those needs are obviously always going to be unique. The first thing we do is I get my team together with the client and we’re clear. Not what I heard, but directly from the client’s mouth, what they’re looking for and what their metric for success is.

From there, my team goes back and we start creating and iterating. I’m clear with all of our clients from the beginning, the fact that this is an iterative experience. This is something that involves collaboration. If you’re looking for a one-stop fix for any creative service. That doesn’t exist. That would involve mind readers. What I’m looking to do is build a partnership with these clients. Not just to service them but to service them for their careers and for their businesses in totality.

What’s the shape of your firm look like now employees and contractors? How do you think about that and putting your team together that’s got all these different skill sets that you need?

Probably one of my biggest learnings of owning the company and growing the company was right when I got started. I scaled and I scaled quickly out of necessity. I went from it being me to me having about around 32 full-time employees in a matter of six months, which is significant for a creative agency.

During the pandemic.

We were talking right at the beginning of 2020. It was significant. What I found personally is that quality control suffered exclusively because I wasn’t able to manage to the degree that my employees deserved. Beyond that, if employees are trying to manage multiple clients and let’s say maybe their entry level in their careers, it becomes quite difficult to mitigate all of those different nuances.

What I found was scaling back the business was more profitable and alleviated a lot of the stuff and pressure. We moved away from that specific model. I only have three full-time employees and we’re managing contractor roster of 12 to 15. That is a sweet spot. Now, I’m able to hire the best per project. I also don’t have the overwhelm or stress of additional overhead that might not be utilized this month depending on the projects that come in.

I hear that so much from entrepreneur, the world is moving more toward a gig economy and you’ve got more people who are working as independent contractors. If you’re an entrepreneur, as you are, you’ve got the opportunity to bring people in as you need them then you move on to the next thing. You may need somebody different and that’s a model that has grown up. It was huge in tech decades ago, but it’s grown up to a lot of other industries since then. It’s a little bit godsend for entrepreneurs these days.

There are advantages to having certain people be employed. You can ensure working hours, prioritization and work process even. Whenever I’m working with consultants, my clients just want the best. My ability to go to the best and say, “I will need you for this project. Let’s ensure that your fee accommodates the client’s budget.” That’s much healthier. Not only for the business and for the contractor who will make more on that project than they would as an employee. My number one concern is the end client and they get the best results that way as well.

Unintentional Entrepreneur

You were an unintentional entrepreneur.

That’s the case with a lot of us. I didn’t sit down and say, “I’m going to start my own business.” I’ve always been the person who likes leading. I like being in charge. I like commanding the room. All of those things have always been a part of who I am, but I never thought that I could own my own company because that’s something that someone else does. It wasn’t until I was in the thick of it that I realized, “This is something that I can do.”

How have you found the experience overall? Other than the scaling point that you brought up a minute ago, what’s been easiest and the hardest for you?

I love the schedule and the flexibility. What I mean by that is I work longer hours than I did in Corporate America, certainly. I don’t have more free time by any means. My ability to say, “I’m going to go do this in May or I’m going to go on this vacation in November and not have to ask someone.” It’s certainly relieving. I enjoy that but they always say more money, more problems.

I get paid to deal with a lot of the BS that I never had to deal with in Corporate America. That wasn’t my job. I am now managing people’s finances, having legal conversations, and approving contracts. All of those things I didn’t have to do in the corporate arena. I do now and it is incredibly taxing. I find that 30% to 40% of my day centers around those things that aren’t money making activities. I still have to answer the email and submit my taxes, but I was never submitting Playbills taxes or NBC’s taxes. Someone else did that. That’s what I found to be both fun and rewarding and also difficult at the same time.

You get forced into being a jack of all trades.

Yes, you do. That is the truth.

We talked a little bit about this in passing. You had a good run going on Broadway in your various roles. Give us an overview of some of the productions that you were involved in.

My career took many different shapes in the arts. As I told you, I started as a production assistant and stage manager. That is the day-in and day-out operations of the show. Everything from ensuring that all of the production staff is there, to ensuring the calendar schedule, communicating with all departments, and to being at every single show. It’s taxing in terms of time, but I loved that role because I got to be involved in the Broadway community, which was always my passion and dream. I also got to be in charge to some degree. That felt fantastic.

The thing that is a nerving about any arts job is the fact that even at the height of your career, you have to be flexible. The idea that you’re going to work 52 weeks out of the year on a contract on Broadway is very unlikely. Even still, you have to find ways to make additional rent. You can’t spend and live paycheck to paycheck despite you basically needing to in New York City. In between layoffs, which are very common. Even if the layoffs 2 weeks or 3 weeks or 4 weeks, you still are trying to find some creative outlet.

What I did was I started an interview series on YouTube. This was in 2013. This was far before the word influencer existed. I was doing it because I loved my friends on Broadway. I enjoyed doing something that no one else was. That accidentally changed my life. It turned into what is now known as influencing. Twice a week, I would have a famous star come to my living room in New York City, sit on my couch, drink wine, and play a game with me.

People started to take note because it was authentic. It came from a place of, “This is Tyler. Tyler enjoys spending time with these people.” It gave access to so many people around the country. I did that for a long time. It was eventually acquired by Playbill, that Broadway legacy brand, I worked for a while. We hit the ground running. We showed this vlog to over a million people in 168 countries per month.

It was a significant undertaking. It was allowing me to live my dreams like I never thought possible. Ultimately, I was like, “This has played itself out.” I had done it for a few years. I was tired and exhausted. It’s a lot of time and energy for very little income, in my opinion. When I had the opportunity to transition to Corporate America and the paycheck matched. I jumped because my dream role, if it wasn’t on Broadway, it was working at a company like NBC. When I got the opportunity, I obviously left and did my time at NBC.

What I will tell you is when I was leaving the industry or what I thought was me leaving the industry. I was offered a position as a producer. Something I had never done before, but a third party, a fantastic producer named Hunter Arnold and his associate, Kayla Greenspan saw something in me coming from the world of entertainment and being a public figure at the time in this very small niche.

What I found was that they allowed me to do this and that’s where I got my legs of producing. That’s where I’ve been able to achieve my, for lack of a better word, I’ll say production status in terms of the Tony Awards I’ve won or the Grammy or the Olivier’s. That came as a byproduct of me creating and doing what I loved on the vlog.

I want to come back to that, but I’m curious. Your show gets bought by Playbill. You go to Playbill and you’re doing this show for Playbill. You’re the product, then you say, “I don’t want to do this anymore.” How’s that conversation go with Playbill?

Playbill was good in terms of, I’ll say for lack of a better word, they were licensing it. They were paying for all production. I was showing up and doing the show. They were paying me a salary to do so. In addition to other assignments, they would have for me. You’re right, I was the product and they knew that. They were conscientious of that. The conversation that I had with everyone was kind and respectful. They did the same thing for me. We sunset the vlog and they sent me on my merry way. They were good to me. I have nothing but gratitude for my experience there.

You ended up at NBC.

I did.

Describe some of the things you were doing while you were there.

I forgot my specific title. I was head of digital marketing for a specific section of NBC called content commerce, at the time. It was like you could guess the intersection between their first class, first tier content and online commerce potential online. The number one project that I worked with was closely collaborating with the golf channel of all channels, but we did on-screen and in-person promotion that would link to the masters.

We would have on screen shopping. We would have in person activations. Essentially, you’re watching Tiger Golf click here to buy his shirt on a linear activation. That’s what we were working on at the time. It has ebbed and flowed into a new iteration of what it is now past my time at the organization. That’s what we began there and I was proud of the work we did.

Big company. How did you find that?

Massive company, but it’s something I always craved. I loved my ID batch, going into the big office, collaborating, sitting with friends, colleagues, and co-workers and walking to meetings. All of the things that you look for in a 9:00 to 5:00 corporate job NBC had. It was a company that I looked up to for a long time that I still look up to. I loved my experience. It was an incredible opportunity.

You were you at Rockefeller Center?

I was. I was right across the street, technically 12-21 but it all connects. We were in 30 Rock every day.

I used to work in an office over there every now when I go to New York. You feel that 30 Rock vibe.

I love it. It was fantastic.

You have the Today Show out there in the back part of our office. When they would have a live performer, you could not concentrate. You were getting a ticket to that concert whether you wanted it or not.

Let me tell you, the gossip here is that the NBC cafeteria is so good. It’s so good and it was so inexpensive. We loved going there every day. It was a great experience. I loved my time at NBC.

You went into this production role that as you say opened up the opportunity to win the Tony’s, the Grammy’s and Olivier’s. That’s pretty impressive.

I appreciate that. I was in the right place at the right time, but I would be remiss to say, that was all it was. It was that in addition to having mentors and people who believed in me, namely Hunter and Kayla from a company named TBD Theatricals

. They are icons in the production space. The reason they knew of me was exclusively because they knew of me was exclusively because of this vlog. I did myself some favors, but it is because of people like that believing in you and showing you that you could do something that you maybe feel like you couldn’t to move the needle.

It must have been completely on the opposite end of the spectrum relative to working at NBC.

Keep in mind, it was, dare I say, part time. I never quit a job in order to do that full time -time just because it doesn’t pay living wage at the level that I was doing it at. You will find investment for maybe 2 to 3 shows a year. One of which recoups and makes some money. In terms of that, like paying your bills. Not so much. I do that as a venue to continue to stay connected and be a part of the industry I love so much in a new and exciting way.

What was your day-to-day like then?

At the beginning of my producing career, I was at NBC. I would work 9:00 to 5:00 in NBC. At the end of the day, I would have a lot of phone calls with potential investors. I would sit on the phone pitching the show, whatever show I was working on at the time, saying, “This is the show I’m working on. Here’s why I’m working on it. This is why it might be good for your portfolio. Let’s have a conversation about it.”

Getting told no 95% of the time but then getting those few yeses, which is exactly what you’re looking for. Day to day, it was working job one and depending on the season, going to, I’ll say, job two for an hour or two each night trying to get caught up on my email and make sure that I had all of my production things in line as well. Depending on the season, there would be some weeks I didn’t do any work. There would be some seasons I would do that five hour a day.

You left it?

It’s a little convoluted. The answer is yes overarchingly. There are a few projects that come across my desk that I’m like, “This will be easy and I want to be involved.” I’ll do something like that. We opened Hades Town, the Broadway musical in the West End. We were just nominated for my second Olivier, which is fantastic. Unless it’s something like that, it has to be an killer project for me to say, “It’s worth my time coming on.” Not because I’m looking for a massive payday, but because my day to day here at the agency and as a business consultant is so taxing 8:00 AM to 6:00 PM with very little break.

Trust The Process

I can’t imagine being an entrepreneur for most people is a pretty all-in experience and theater. There’s parts of it that aren’t quite as time sensitive, but there is a show to put on every day. I’m sure you’ve gotten good at time management over the years.

I certainly have. If nothing else, I’m efficient, which is my superpower so I love that.

The real estate experience, how did that come into play for you?

Again, through happenstance. I’ve always loved real estate. The glass ceiling doesn’t exist there. We can have untapped earning income theoretically on paper. Whenever I was in college in Austin, my dad knew someone who got me a job working minimum wage and filing at a real estate office when filing was still a thing. Not to date me, but through a strange series of events that company dissolved and the top agents from that brokerage and they were and still are.

Many of them, the top agents in Austin started a new organization and was fortunate enough to be brought along for the journey. I did that. That’s where I got my understanding, my initial understanding of real estate and how to do it. When I moved to New York City, I pursued Broadway but then after that, I have always loved real estate. It’s what I excel at. I understand the industry and I understand the personal branding component, too, and now the marketing component.

That’s where I sit most of my day is heavily in the real estate niche. Exclusively because I’m licensed. I don’t transact. I have zero desire to sell real estate. I say that because it’s helpful. That’s where I sit most of my day working with the top, let’s say 1% to 2% of brokers and real estate agents in their given market.

Go back, you went to college at St. Edward’s. You majored in Theater Arts. What did you foresee yourself doing professionally when you finished school back then?

My answer is simple. I knew that in order for me to be happy, achieve my dreams and do everything that I want to do. I was going to be a Broadway actor and so many people think. I had the dedication and the passion to do it. I’m motivated but those two things doesn’t necessarily buy you your leading role. What I found very quickly is that I dreaded it.

I hated the business of acting on Broadway. I didn’t want to audition. I didn’t want to be compared all the time. This just in, that is the business. You can’t overlook that. What ultimately ended up happening is me finding different venues in order to be involved that were more suited to my skills, but most importantly got me excited to be involved. That’s how I transitioned into stage management.

It’s funny, I tell this story all the time. The things that I wanted whether it was a Tony Award or to be known in this industry or be able to meet, I’ll call them my idols who I grew up wanting to meet eventually and become. All came true just not by me trying to dictate how they came true. I followed my authentic truth which was me creating this web series. Through a strange series of events, I got those Tony Awards. I got to meet all of the people I wanted to meet.

That showed me an important fact, which is, as long as we know where we’re going, we don’t necessarily have to know every single turn in order to get there. That is what I continue to remind myself, even in moments where I feel down as an entrepreneur. Am I doing the right thing? Am I moving in the right direction? I have to remember that I’ve always been moved in the right direction. I just have to continue to trust the process.

Nobody’s career is linear and I certainly hear all the time. One of the questions I often ask people is, how much of your career has been intentional? How much of it’s been opportunistic? Most people will say that the vast majority of things that have come up have been opportunistic. Very few people. I had one person I interviewed who decided that she wanted to work at the World Bank or the International Monetary Fund. I can’t remember when. She was like twelve. She ultimately did work there, but that’s rare.

Very rare.

For most people, you don’t know. When you’re in college, you don’t know what you’re going to like and the reality of what can you make money at. You’ve described that at several points in the conversation thus far. It factors in. You have to come to this intersection of passion and enough profit that you can make the living you want to make.

I couldn’t agree more. Imagine if you had to stick to exactly what you wanted to be when you were eighteen years old and you could not deviate from that. How miserable people would be? What weird jobs we would all be having now? I would be destitute as a failed Broadway actor. We do have to remember and this is what I always remind myself, dreams change and that’s okay. Giving up on your dream that you love is different than saying, “I woke up and I don’t enjoy doing this anymore.” That’s not giving up on your dream. That’s saying, “My dream is shifting,” and figuring out and identifying what that next thing is.

Digital Marketing And The Personal Brand

I want to talk a little bit about digital marketing if that’s okay. It’s a topic that people are super interested in. It’s booming. More of the marketing spaces has moved online. What are the things that you would describe as your specialties?

The number one thing that I specialize in is becoming more and more popular, but it’s this idea of what I call personal brand. I don’t care about brand marketing or product marketing as much as I do the individuals who are selling the product. My work with even Fortune 100 CEOs has centered around them and the ethos they bring the organization.

What I want to stress very matter of fact is let’s take real estate for an example. If you are an individual real estate salesperson, your ability to write a contract doesn’t make you special. Your ability to pull a listing doesn’t make you special. Anyone on Earth could do that. that. There are rocks who shouldn’t have the real estate license who do this.

However, the differentiator, the thing that makes you different than the other person is you. My job is to harness what makes you authentically showcasing that to make you human and to make people want to shop with you. We want to know and trust you. You hear that all the time, but it’s so important when we’re talking about entrepreneurship. People come to my agency not because we’re the only people on earth who can build a website. There are thousands, if not millions of website providers.

They come because they want to work with me. I understand that and I leverage that. The same way, is this the only entrepreneurial show on Earth? No, if someone else wanted to read an entrepreneurial show, they could go to many other places. People read to yours because of you. If we only focus on the show, versus focus on the person whose lens the show is being told through. That is a big disconnect.

What I find and what I have found time and time again, is that me seeing a glimpse of your human life makes me want to leverage you and your product more than you telling me about the product because that’s lifeless. My specialty is focusing on every single individual’s personal brand, how we harness that to inevitably make more money.

I would imagine that’s a big part of the initial going. It’s helping them figure out what is their personal brand because probably, most people don’t come to you and say, “I’ve got it. Here it is. I just need you to help me market it.”

Not at all. The most toxic word I believe in business is should. All the time I hear multiple times a day, “I did it because I should or I should be doing this or I should be looking like this or acting like this or wearing this or marketing this way.” I say, “Says who?” There is no rulebook. Instead, you doing what you think you should be doing versus what you feel is authentic is a major misstep. Why? It’s because there is someone out there authentically doing the thing you think you should be doing. It’s going to get every one of your clients because it’s not authentic to who you are.

What I focus on is let’s identify the brand, label the brand and define the brand. All of those things are true. Beyond that, once we understand what the brand is or what we want the brand to be, how do we create an ecosystem so that consumers perceive it to be that as well? The number one thing I always say is user perception is truth. Not accurate, but if we perceive Gucci to be elevated and luxurious, versus a cheap knockoff brand. We are consequently willing to pay more for it.

The good news for all people is that we have an uncanny ability to affect people’s perception immediately, regardless of your product and of your ability or your experience. That’s why focusing on the website, on the logo, the way that your brand looks and the tonality or what we call the positioning of your company. You in your brand is the most important thing we can do.

How did you learn all this? You didn’t go to school to major in marketing.

I did not major in marketing. I do have a postgraduate certificate from MIT in social media management. I did do that, but I will also say, I’ve been fortunate to work with some incredible leaders. Whether it was my boss’s boss at NBC, who was Linda Yaccarino who’s now the CEO of Twitter. I have personally rep Spencer Rascoff who invented Zillow, John Legere who was CEO of T-Mobile and the president.

Through this work, I have worked alongside exceptional people and that teaches you far more than a Marketing 101 course ever could. I’m a lifelong learner. I would be lying if I said that I attend class every day, but I certainly am constantly trying to learn because people who were marketing legends in the ‘90s who didn’t learn, don’t have jobs now. That’s important to me as well.

Coming back to digital marketing, what are the things that are most important to get right?

Number one is an authentic voice of who you are. Not who you think you should be. That is difficult for a lot of people. You think of legendary entrepreneurs like Gary Vee or Grant Carter or any of these more popularized household name entrepreneurs. Whether they know it or not, they are exceptionally authentic. Whether you like their authenticity. That’s not for debate and doesn’t affect me.

Instead, Gary always talks about, “I have the mouth of a sailor. If you don’t want me to curse, I get it. I’m not offended. I’m not the right person to show up for this marketing conference or I’m not the right company for you to employ as a creative agency.” What we start to find is the need first and foremost to be authentic in your space. Finding, harnessing, and embracing that is exceedingly difficult, especially for more legacy providers. People who have been doing this for a long time, it’s quite difficult.

The second thing I would stress here is you have to look at your ecosystem unbiasedly. It is so easy to think you have the best product. It’s so easy to think that it’s easily communicated. I want you to think if you were a consumer who didn’t know who you were or didn’t know what your product was, am I going to hit your website? Worse, Google your name or your product and think, “This is the best product or this is the best person for the job?” If the answer is maybe or maybe not, you’re already doing yourself. What’s the word?

I’m in the circus.

Thank you. The answer is quite clear. If you can’t say that your ecosystem conveys that you’re the best in the business at whatever it is you’re doing. It is a massive misstep.

What are some of the other things that people get right and wrong?

We always talk about content strategy. How can I get in front of people consistently? It’s important to remember, it takes me an hour to have an hour-long conversation with you. Versus me recording a 15 to 30 second reel, putting it online and 3,000 people getting to see it. Does that mean we’re going to have the same level of intimacy or connection that you and I have talking one-on-one for an hour? Certainly not.

I will tell you that 3,000 people thought of me and that’s what’s important to remember. We try to be so precious with a lot of this stuff, “All of my social has to be perfect.” No, it doesn’t. People are looking at it on average less than one second. If they watch it, they’re watching 50% of it. Give me a reason to remain top of mind with the consumer. That’s important.

As long as you don’t go to a level of saying something stupid or doing something stupid.

That’s different. You don’t want to be remembered for being an idiot. The idea that your social has to be the most groundbreaking and viral sensation every time you post it is a misnomer.

Tyler Mount: The idea that you’re social has to be the most groundbreaking viral sensation every time you post it as a misnomer. It’s not going to happen.

It’s not going to happen.

Never. It’s physically impossible.

Agency Leadership

For people who are interested in getting into this space, what advice would you give to them?

There are two sides to this space. There’s the side where people do what I do, which is helping people go to the next level, which is rewarding to me. I would say if that’s the side you’re looking to explore, showing up as a human being, being kind and courteous and on top of your life and on top of your work product is important. These people are spending a significant investment for you to help them.

Showing up prepared, showing up, answering their emails promptly and treating their business like they treat their business is important. If you are a business owner or an entrepreneur and you’re thinking, “Personal brand doesn’t affect me.” If you’re saying, “My content is fine enough.” You need to rethink that because I guarantee you if I were to search your first and last name or your company’s name. I would bet statistically speaking, almost 100% of my clients come to me with an incomplete ecosystem. Whether it doesn’t look good or everything is outdated.

I was working with a top real estate agent and this woman is closing hundreds of millions of dollars of real estate per year. She’s in the top 1% of her market and her LinkedIn hadn’t been updated in years. It said she was a grocery store manager. I said, “I understand you still live in a mansion. I’m not arguing that but we can’t agree that there is at least been one person who has googled your first and last name and LinkedIn’s the number two head.

Gone there, seen an outdated profile without a profile photo that says you work at a grocery store and probably didn’t call you.” That could be a small million-dollar deal that’s $30,000 you just lost from not updating the LinkedIn. That’s ultimately what we work on together, how can we ensure the integrity of the ecosystem because we can’t control how people find you. We can only control the narrative once they’re there.

You’re a founder, a CEO and in a leadership position. How would you describe your leadership style?

I love delegation. I have no qualms letting someone take the wheel. That’s helpful because I’m so busy and so are so many people. I’m not alone in this, especially in today’s world. If I hire an art director, I am never overseeing what that art director does until I need to. I am always here in order to give feedback, answer questions and give you my opinion. If I have to tell you how to design, I hired the wrong person. The same thing with operations and sales.

I’m trusting at the beginning. Through owning a business, I’ve learned that sometimes you have to be a little bit more stern in a kind and respectful way and be like, “This isn’t the little standard of excellence that I’m looking for here. We have to change it or we have to find someone who can do the work.” Delegation is key. I look to my team to keep me updated and to tell me what’s happening in their departments. I will always jump in and be in the weeds with them if they need it. Leaders who also say, “I’m going to delegate,” but then try to micromanage and do all of the work. Not helpful at all.

How does that translate into that culture that you want to establish?

My team knows that I trust them implicitly. I adore them. They always have autonomy. They understand that I write the check and I’m the boss per se. For a lot of my employees, I’ve had to reteach what it’s like to be in a traditional corporate setting. The only thing I mean by that is, I’ve exclusively worked for individuals in Corporate America that I had disagreements with or didn’t feel like I was working in the most advantageous of cultures.

That taught me how not to lead as well. I find that’s the case with a lot of people. Whenever I ask a question and people are like, “I’m so sorry that I did that wrong.” I’m like, “No, you’re misunderstanding. I’m not mad. If I was mad, I would tell you I was mad. I’m just wondering why you made that decision because it’s probably outside of your control or it’s a process issue that we can fix.” I’ve been working and we’re not a good spot. They know unless I tell them or missed the mark or my questioning and my questions are to improve the process. They know that. I trust them implicitly.

What do you look for when you hire people? I know you have a huge number of employees, but in the past, what do you look for?

That’s taught me a lot. I will say the number one thing I look for is a good attitude and that might seem so easy. It might seem like a no-brainer, but I would rather have someone with “less talent” who shows up and is, “Okay.” That’s not what I was planning for. Not in terms of the job description. I’m talking about, “This client deliverable didn’t get the feedback I was expecting. Let me pivot and let me make it right.” Instead of complaining about it and not doing the work I was having to have three meetings about it. I need someone who can be solution oriented, do the work and have a good attitude about it.

As an entrepreneur, we pivot all the time. I had 30 employees. I now have three. I had a lot of contractors. I have more contractors now. We offered this service. Now, we offered that service. We changed names. Especially in startup culture, we need a group of people who are positive and who can roll with the punches and be solution-oriented ultimately.

Tyler Mount: We need a group of people who are positive and who can roll with the punches and be solution-oriented.

You’re still in the early part of your career, but you’ve done a lot of different things already. When you look back on the things that you’ve done, what have been the consistent strengths that you’ve drawn on?

I am efficient. I am quick. I would also say, that’s also a con of mine as well. I’m very fast. My ability to talk to a client and get them the answers they need quickly is unmatched. I think at the end of the day, I am relationship based. I love people. I love talking to people and building close personal connection with people and my clients. That is why people want to work with you.

My ability to genuinely love a potential client or want to continue to build a relationship with a future client always comes from a sincere place. They feel that and oftentimes, it’s reciprocated. My real strengths here are not only efficiency but also being motivated and wanting to build relationships with people to better them and better their lives.

What have you had to work on developing?

Personally, like internally, I have a terrible habit of becoming apathetic when I’m overwhelmed. As an entrepreneur, you are constantly overwhelmed. At some point, you’ve reviewed so many contracts or you have so many things going on that you’re not going to take care anymore. You have to remember, it’s not just your livelihood. It’s other people’s livelihoods and you have to get back on board.

We’re having our weekly financial call that we always have. I’m like, “I don’t know the answer here. Can someone decide?” I catch myself being like, “No, I do have to think about this and make this decision. It’s my company.” Even when you don’t feel like you want to be on the train, you have to be on the train. That’s something that makes entrepreneurship difficult and not for everyone. Here I am on the train now, so we’re making it work.

Have you had any particular failures that you look back on that you feel were big learning opportunities for you?

My career and like so many entrepreneur’s careers are riddled with failures. I would say that having to downsize my company from 30 to 3 employees is what many would count as a failure. Was it a pivot? Yes. Was it intentional? Yes. I have 150 employees and we’re billionaires. Sure, of course. The ego obviously wants that but that allowed me to focus on my priorities and quality versus quantity. All of those things in life, things that I would have counted at the time as a massive failure or a massive misstep have led me to exactly where we are now. I’m thankful for that.

As somebody said, “There’s success and there’s learning.”

I love that. You’re failure are tons of learning. I’ve made many mistakes in my career and I will continue to make mistakes. I’ll make more mistakes now. We just have to learn from them and continue to better ourselves. That’s the mindset I try to keep myself in.

You’ve probably hinted this a bit, but are there particular routines or habits that are important to how you operate?

I am very hippie-dippy woo-woo as I like to call myself. I love the idea of the law of attraction. I love my affirmations in the morning. I try to sit with myself and prioritize my goals for the day. I have my to-do lists, which I follow relentlessly. They’re so incredibly valuable to me in terms of prioritization. I have my daily rituals and my daily habits, which are important to my success and the success of my team. I make sure to maintain those.

Is there a time of day that you’re most productive?

I am a morning person through and through. Right around 1:00 or 2:00, put me in bed. I could sleep for the rest of the day but 7:30 or 8:00 before my team logs on, I’m already on prioritizing. Not because I work harder by any means. It’s just that’s when I work well. My operations manager loves working after dinner. She’s like, “I love sitting in,” and mindlessly watching television and handling her administrative work. She logs on later because of that. Be my guest. I’m not picky about any of it. I just want to provide a conducive working environment for everyone who works with me.

What do you do to recharge your battery and keep yourself energized?

Get the flu so that I don’t have an option but to lay down. No, I joke. I had the worst flu and I haven’t been sick in a long time. In all seriousness, I find myself very hot and cold. I’m either 100% working or I’m 100% out whenever I log off for the day and that varies. I’m never logging off before 6:00. Not that’s good or bad, it’s a fact.

I have dinner plans around 6:30. Starting at 6:30, there’s very little that could get me back online. I do try to balance these things. Even on Saturday or Sunday. If you email me on a Saturday, I’m probably not running out of time, I’ll read it. If it’s urgent, I’ll reply, but that’s what like Sunday evenings are for me. I try to set boundaries in the traditional sense to give myself that space.

I just had to start saying no to a lot more things which is difficult for me. No, I don’t have time to take that meeting. No, I don’t have time for that podcast. No, I don’t have time to pitch our services. It has to go to a sales team member. Ultimately, that is where I’m trying to the best of my ability and not always successfully try to finesse my time.

That’s especially hard when you’re an entrepreneur.

It’s nearly impossible, one might say.

What’s one thing that you wish you had known at the beginning of your career journey?

I don’t regret this, but I would say that good things take time. When things get hard, you shouldn’t quit necessarily. I’m glad that I transitioned in the way that I transitioned from career to career. I am because I’m here for a reason. I often do look back and go, “What if I hadn’t have left Playbill? Would I be like a global superstar now?” I don’t know. There’s no way to tell.

Tyler Mount: Good things take time and when things get hard you shouldn’t quit necessarily now.

The same thing, “What if I hadn’t left real estate sales when I was in college? Would I be a billionaire now?” I don’t know, but the thing that I now know, not to sound cliche, but everything happens for a reason. In the moment, those things that you think are awful or you think you’ll never come back from or are completely derailing you and your life are oftentimes massive blessings and they’re for a reason. To end those moments instead of being distraught by it, be like, “Thank goodness that this is happening. I don’t know why, but thank goodness because it’s leading me to something better.”

There’s a million different times in the course of a day. Let alone a week, a month, or a year, where you face a decision. Your life takes a turn. I’ve always loved that movie, Sliding Doors. It’s a great and simple example of how life can change depending on one simple event. We face that all the time. If you continue to think back on all those things, you’ll make yourself crazy.

The reality is, we have no idea. Could I have been much more successful doing that? Maybe. I also could have been hit by the subway going to my next assignment. We could play this game forever. That’s what is important, trust your gut, follow and don’t regret the things you did.

Keep looking forward.

Recognizing things takes some time.

Last question, are there any last career lessons that you would want our audience to take away?

I’ve worked with fantastic people. I’ve worked with horrific people like everyone has. I will tell you that I’ve tried to dedicate my career to this concept of that lighting someone else’s candle doesn’t extinguish your own. My ability to help someone, even if I don’t get a paycheck from it because it takes me ten minutes, doesn’t extinguish my value or how important I am. Instead, it can lift someone else up and that has been helpful to me in my career. Not only to justify, why am I spending an hour doing this or 30 minutes doing that? Most importantly, beyond that, it’s always come back to me tenfold. That’s where I try to live my business philosophy through that lens.

Some good lessons there. Thanks for doing this. I enjoyed our conversation.

Thanks so much for having me.

Have a good rest of your day.

I appreciate it. You too. It’s great to meet you, JR.

I want to thank Tyler for joining me to discuss his creative agency, his work on Broadway, some of his earlier career activities, and the things that he’s learned thus far in his career. If you’d like to make the most of your career, visit PathWise.io and become a member. Basic membership is free. You can also sign up on the website for the PathWise newsletter and follow us on LinkedIn, Facebook, YouTube, Instagram, and TikTok. Thanks.

Important Links

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• Gary Vee
• Grant Carter – LinkedIn
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About Tyler Mount

Today my guest is Tyler Mount. As a leading expert in real estate branding and marketing, Tyler has served as a consultant to nearly 1000 agents spanning 14 countries worldwide. His experience spans brand development for residential agents, national brokerages, and commercial brokers, in addition to new development portfolios valued at over $7 billion.

Tyler is also an industry-leading branding and digital strategy expert and the owner of Henry Street Creative, a creative agency specializing in brand design, content creation, and web development for some of the most esteemed industry professionals. In this capacity, Tyler and his team have partnered with a range of companies and individuals.

Prior to starting Henry Street, Tyler was a Broadway producer and influencer. His productions have won Tony, Grammy, and Olivier Awards. His career has been profiled in dozens of reputable publications, including The New York Times, Forbes Magazine, Medium, and Out Magazine. He has also served as a keynote speaker for marketing and real estate conferences across the country. His non-traditional, direct approach empowers agents and business owners to take control of their businesses and build empires. He works and lives in New York City.