Kyle Taylor – Founder & CEO, The Penny Hoarder

While managing massive student loans and debt in 2010, Kyle began to blog about his adventures in making and saving money. Readers responded and this culminated into the launch of ThePennyHoarder.com.

Under his leadership, The Penny Hoarder has grown from a personal blog to one of the largest publications on the web with millions of readers a month. The Penny Hoarder has pioneered a new kind of personal finance media with stories about real people and actionable money tips that make a true difference in our readers’ budgets.

Kyle is active in local politics after spending nearly six years on the road as a campaign worker crafting media strategy, directing field workers, and raising millions of dollars for important causes. He feels passionately that people should earn a liveable wage no matter what their job is. In 2016, the Inc. 5000 ranked The Penny Hoarder the 32nd fastest-growing private company and the No. 1 fastest-growing private media company in the United States.

Tell me about your background.
I moved to Florida when I was thirteen for high school. My parents had just gotten divorced. My dad, who had worked for a credit card company for a long time, quit his job and became a tennis pro, and now teaches tennis all over Colorado. My mom is a phlebotomist. She works in the lab at a hospital. So we moved to Florida, and my passion was always in politics. So after high school, I went to the University of South Florida, for an entire semester, and studied political science. During my first semester, I was offered a job on a campaign, and I dropped out of school. For the next seven years, I worked for political campaigns all over the country, living out of a suitcase.

How did the concept for The Penny Hoarder come about?
The thing about working for campaigns is that you’re always out of a job. When the campaign ends, you’re looking for the next gig. So I was doing side gigs, in-between. I went back to school. At one point, at the end of the seven years, I found myself with over $50,000 in student loan and credit card debt, and so The Penny Hoarder really started, part-hobby and part-lifesaver. It was a way for me to hold myself accountable, so each week I would share how much debt I had paid off, and what side gigs I had to add a little extra income to my pocket.

How did you come up with the name, The Penny Hoarder?
I wish I could tell you that there was some beautiful focus grouping that came up with this great name, but it was really just the first thing that came to mind. It wasn’t a business at the time, but it’s come to be known to us as a way of thinking that if you take care of the pennies, the dollars will take care of themselves.

How was the first year?
I wasn’t making enough money from the site, for it to be more than just a blog. I still worked on the side. I had night gigs on the weekends. My favorite job was as a beer auditor. I got paid to go to grocery stores and gas stations, and see if they would check my ID. I could do twenty to thirty of them in a day. I would do those at night and on the weekends, and these side jobs became the father of what I would write about during the day.

Did you ever raise capital for the business?
So far, I’ve still been able to bootstrap the company. I’ve never gone through a funding round.

What were some of the challenges you faced with growing the business?
Two things. First, monetization. I started monetizing the side with display banner ads. What I found is that I had to have an insane number of readers to make even just a small amount of money with banner ads. Finding a business model that worked was one of the initial challenges. And then, finding a group of readers. When I made the transition, two years in, from hobby to business, obviously growing a reader base was extremely important, and I had never done that before. There were a lot of things I’ve tried, and a lot of failures, to figure out how I would get growth there.

I read, in one of your prior interviews, that you were on the Google AdSense blacklist?
I was. At one point. I did lose my AdSense account, which was devastating, because not only was it my business model, but it was also my rent money. It was definitely one of those moments where I questioned whether I should continue, and I thought about giving up. But it ended up being a blessing in disguise because it put me on a path to find something more sustainable, with higher CPMs.

Do you feel like you have a lot of competition?
I didn’t feel that way when the site first started. I actually think that’s why it took off, because a lot of the personal finance websites were catering towards a different audience, people who already had money. I do think that’s changing, and there a lot of large media companies right now that have started sites this year in the personal finance area, so it is getting more crowded.

What has been your marketing strategy?
We always say that we’re not quite a news site, although we do cover breaking news. And we’re not quite a blog, although we do have a very blog-like tone, so we’re somewhere in the middle, and that’s been part of our marketing strategy. We always say that we’re going to make personal finance fun, interesting, and entertaining, often putting the personal in personal finance, even if it’s someone on our team sharing their story of paying off their debt. But we’re still going to employ the same fact-checking mechanisms like every other news site. So finding that middle ground has really been our marketing strategy.

What is an average workweek like for you?
During the time period when the site was just a hobby, there were weeks when I would work on the site for 10 hours, and then there were weeks when I would work on the site for 80 hours, just like any hobby. When the site became a business, but I was still on my own, I was working a pretty standard 40 to 50 hours a week, and now that I’ve opened an office and hired staff, I would say it’s closer to 80 hours a week.

When did the website start becoming profitable?
I’ve been lucky that it’s been profitable since the beginning. There weren’t any startup costs. When the site first started, I couldn’t even afford a domain name, so I started it at ThePennyHoarder.blogspot.com. So I’ve just been able to reinvest revenue each year into growing the site, and I’ve been lucky that it’s been profitable since the beginning. Although in the first couple of years, it was pretty small profit numbers. It was only during the third year when I was able to start taking a salary.

Fastforward to today, how fast is the business growing?
We were able to more than double revenue and users last year. Last year, we did $20 million in revenue and 12 million visitors a month. This year, we’re on track to doubling those numbers again, and we’ll end up with around $40 million in revenue and, hopefully, somewhere around 20 million visitors a month.

How many employees do you have?
We are at sixty-nine employees, as of today.

How do you organize your day?
My day has definitely changed. The larger the company gets, my tasks change. Now, I don’t really spend as much time on the content side, aside from high-level strategy. A third of my time is recruiting, some of that including press. A third is developing leaders here in the company, and helping our executives, and a third of my time is more high-level strategy. In terms of my specific day, I’m an early riser. I usually start around 5 a.m. So 5 a.m. to 9 a.m., is my time to catch-up and get things done. Read the news. I really try to block that time off every day. And from 9 a.m. to 5 p.m., every day, there’s usually a meeting every minute of that time. Generally, with my team, or with job candidates. I try to go home by 5:30 p.m. every day. I think it’s really important to have a couple of hours to unwind and relax. I’m guilty of checking one more time before bed, around 8:30 p.m., then it’s lights out for me.

What kind of people are you looking to hire?
It definitely ranges. I would say 45 employees are content creators (writers, editors, videographers, social media), and then we have a sales team, consisting of six people. We have two people in HR. This year, we’re hiring a lot more on the video side. We’re building a studio, so we’ll be hiring audio engineers and on-air graphics engineers and producers. We’ll be looking to hire those kind of people later in the year.

What are some of your daily habits that have contributed to your success?
As mentioned, I’m a nerd. I love to read. I think that taking time every day to read is something that’s really important to me. Saturdays are “reading days” in our house. We sit around and read magazines, books, as well as briefs that I didn’t read during the week. Not only does it help me gain new knowledge, but it is almost like meditation to me, and calms my mind into thinking about something different.

What are some quotes that you live by?
One of my favorite quotes is by Steve Harvey. I saw him on The Oprah Winfrey Show a while ago, and he said something like, “Stop telling your dreams to small-minded people.” That stuck with me, because I remember when I first started, and I would tell people about this site, like friends and family, I received such a wide range of reactions. Some people get so excited for you, and some people give you that look, like “Oh, that’s great. Nice.” One of my friends, who I love, but would constantly refer to the site as “The Penny Pincher.” It was just little things like that made me believe that they didn’t believe in me. So I love that Steve Harvey quote.

What are some of your favorite books?
One of my favorite books is only about fifty pages called, The Shift from One to Many: A Practical Guide to Leadership. It’s a really quick book about management. It’s one that I’ve reread constantly, because it talks about the different levels of becoming a manager. In the beginning, you’re making every decision, and then the further you move along the path, it’s more about empowering others to make decisions. I read it constantly to serve as a check on myself, and to continue to grow. I also love biographies. I’ve been reading biographies about other people who have started media companies, recently. I started reading a biography about Rupert Murdoch a couple of weeks ago. I just picked up one by Ted Turner, but I haven’t started that one yet.

How do you define success?
I think success is being able to go to sleep at night, feeling good about what you’ve accomplished that day. I don’t think there’s a measuring stick with money, time saved or anything like that. It’s if you feel good about what you spend your day doing.

What is the key to success?
It’s constantly asking yourself if you’re enjoying what you’re doing. Tim Cook had this great quote. He said that every couple of days he looks in the mirror and says, “Did I like how I spent today?” He said if he gets too many of those in a row, where it was “no, today wasn’t a great day”, then he knows it’s time to make a change, in his career or whatever he’s doing.

Did you always know you would be successful?
As humbly as possible, yes! I didn’t know I would be in this arena. I’ve always been very competitive and motivated, and so I knew I wanted to achieve big things, but I had no idea i would be running a media company.

When faced with adversity, what pushes you to keep moving forward?
As I mentioned, I’m very competitive. So I think that competitive spirit is where I really draw all my grit from. The idea that I really don’t want to win. I want to finish.

What is the greatest lesson you’ve ever learned?
During the first campaign I’ve ever worked on, which was for an AFL-CIO for the largest labor union, we were working on restoring overtime laws. This was back in 2004. I learned a lot about culture and how important it was to take care of the folks that work for you, during that time. I think that’s been one of things that’s really helped The Penny Hoarder grow so fast, is that we’ve really invested in the folks that work here, and I’m grateful for that campaign for showing me how important that is.

What do you enjoy doing in your spare time?
Besides reading, I do love to play games. I’m a Mario Kart enthusiast. Video games are the way for me to challenge myself and relax at the same time.

What makes a great leader?
I think great leaders are humble and try to spend their time building others up, rather than just building themselves.

Tell me about one of the toughest days you’ve had as an entrepreneur.
One of the toughest things to do is letting someone go. I remember last year, we had someone on our team, who we all absolutely loved to hang out with, but on the performance side, he was struggling. We had tried to intervene many, many times. It just became clear that it was not the right fit. So we had to let him go. It was not only a tough conversation to have, because it makes you feel awful. It was also tough for the rest of the team, who all loved that person.

Did you do anything afterward to make the team feel better about this?
I’m a believer that sunshine is the cure for everything, and that transparency will win in the end. So we were honest with the team, and didn’t hide the fact that we were letting him go. I always hated that at companies, where people would just disappear and everyone was wondering what had happened. So we had an honest chat with people that this is what happened, and it wasn’t because of anyone else. That it is what it is.

What is your vision for the future of The Penny Hoarder?
Personal finance literacy is very important to me. There’s tens of millions of people, and actually, some surveys suggest that almost half of Americans might have less than $1,000 in their bank account, right now. So our vision, and our mission, is to fix that. It’s to put more money in people’s pockets.

What do you think is the most common mistake entrepreneurs make?
Not letting go. It’s one of the more challenging parts of becoming an entrepreneur. The larger the company, and the larger the team gets, the more you have to be comfortable with people making their own decisions.

What advice would you give to young entrepreneurs?
Don’t quit your day job. I want to encourage entrepreneurship, but I believe, sometimes, entrepreneurs have this TV version of what should happen. You go out and raise a bunch of money, quit your job, and go full blast as an entrepreneur. Well, there are other ways to do it. It can start as a side gig, and maybe it will grow a lot slower, but odds are you’ll be able to pay your rent that way.

Tracey Noonan – CEO & Co-Founder, Wicked Good Cupcakes, Inc.

Tracey Noonan is the CEO and Co-Founder of Wicked Good Cupcakes, Inc., the largest shipper of cupcakes in the United States. Tracey co-founded the company with her daughter, Dani. They opened their first retail location in Cohasset, Massachusetts in October 2011. In 2013, a second retail location was opened in Boston’s historic Faneuil Hall Marketplace. Today, Wicked Good Cupcakes has grown into a national, multi-million dollar brand, thanks to an appearance on the Emmy Award-winning show, Shark Tank.

Tracey was a 2015, 2016 and 2017 finalist in the prestigious Ernst & Young “Entrepreneur of the Year” competition. Tracey also mentors female MBA students for Babson College’s Women Innovating Now (WIN) Lab.

Wicked Good Cupcakes was ranked #511 on the “Inc. 5000 List of America’s Fastest-Growing Companies” in 2016. Wicked was also ranked #9 on the “Fast 50” list of the fastest-growing privately-owned companies in Massachusetts, for April 2016 and April 2017. The company also finished building a 21,000-square-foot baking and warehousing facility in Hanover, Massachusetts in July 2016. Their fleet of national, franchised cupcake trucks launch Q3, and Wicked Good is currently in negotiations to enter into international licensing deals in Europe and Australia.

Tell me about your early career.
Earlier in my life, I’ve had several businesses, including in commercial photography (for advertising) and animal wrangling (for print, TV, and movies). I had my human/equine massage therapy license, my real estate broker’s license, and I was also a writer. I did a lot, and learned even more!

How did the concept for Wicked Good Cupcakes come about?
Wicked Good started as a traditional, retail cupcake shop. Shipping our cupcakes in mason jars came about as a way to solve a shipping problem that the other cupcake companies weren’t able to do.

How was the first year in business?
Our first year in business was right around where we had anticipated. We did $320,000 in sales, $75,000 of which being cupcake jar sales. It was during this first year that I also applied to Shark Tank. The following year, sales grew to $1.8 million.

What was your marketing strategy?
To gain customers with as little cost as possible. Thanks to Shark Tank and Kevin O’Leary, our customer acquisition costs have remained very, very low.

How fast did the company grow during the first few years?
The year after we aired on Shark Tank, we grew 600%. We have grown every year since. We have yet to hit our baseline.

How do you define success?
I define success by the number of return customers and word of mouth sales. It’s so much fun to be in another state in the country and find someone who has tried your product or sent your product.

What is the key to success?
Grow smart, not fast. Understand that you don’t know everything. Trust your gut.

What is the greatest lesson you’ve ever learned?
Customer service is the most important aspect of any industry.

What are some of your favorite books?
Delivering Happiness – Tony Hsieh
Life is Good – Bert & John Jacobs
Good to Great – Jim Collins

Tell me about one of the toughest days you’ve had as an entrepreneur.
Some of the toughest days were early on. We didn’t have any money to have a real staff. So that meant Dani and I were working fourteen-hour days, six days a week, and taking zero pay. It was exhausting. I often questioned why I even wanted to have a business in the first place. As we grew, the challenges were still there. They were just different.

When faced with adversity, what pushes you to keep moving forward?
My desire to never fail. This has to be a success. We must constantly take a step back, examine what we’re doing, fix what needs to be fixed, and carry on.

What advice would you give to young entrepreneurs?
1) Understand you’re not going to be rich overnight. For the few this happens to, there are hundreds of thousands of people who struggle to pay their bills.
2) You will be a level of tired as you have never, ever felt before.
3) Understand that you don’t know everything. Be humble enough to accept someone’s help when needed.
4) Understand that mistakes happen. Everyone makes them and everyone must fix them. Once a mistake has been corrected, let it go and move on.
5) Understand that having your own business can be a very long and lonely road. Ask yourself honestly, “Why do you want to start a business?” And then ask yourself if you’re really willing to eat macaroni and cheese for years on end.
6) Starting a business from the ground up is one of the most exciting things you’ll ever do. It’s not a venture to be taken lightly. But once you know you’re ready, go for it. Take a deep breath, take the leap, and enjoy the ride.

Eric Mayville – Founding Partner & Co-CEO, Wondersauce

Eric Mayville leads operations, finance, and culture at Wondersauce, ensuring that the company is run efficiently with an environment that spurs creativity, innovation and respect. A graduate of Ohio University, Mayville’s career saw him commanding a variety of roles within digital firms such as Code & Theory, Razorfish, and AgencyNet. Those roles included motion design, front-end development, visual design, creative strategy, and user experience design and planning. At Wondersauce, his entrepreneurial spirit has been paramount to Wondersauce’s growth and strategy. He was also named one of Business Insider’s “30 Most Creative People in Advertising under 30”.

Tell me about your early career.
I bounced around a lot. It is definitely not something I would recommend to everyone, but NYC afforded me the ability to test the waters with several different companies and several different roles. By the time I found the agency I wanted to stay at for more than six to seven months, I had really seen every role imaginable for producing great work. This was a definite advantage for when we broke off to do Wondersauce. A holistic understanding of any business is critical when thinking about going out on your own.

How did the concept for Wondersauce come about?
Wondersauce was born based on a desire to create our own path and approach to running a service company in a crowded market. We knew we had the ability to deliver quality work for our clients and we had a hunch that if we simplified the experience for clients and ensured that they felt like they were a part of the process, then we could generate the results they were looking for while creating repeat business.

How was the first year in business?
We hit the ground running hard. We scaled from two people in an apartment to about fifteen in our own space. Our clients ranged from start-ups to huge brands, like Stella Artois. All of the work came from word of mouth which really was a testament to our hunch about how to structure our relationship with clients.

What was your marketing strategy?
We relied solely on our clients and personal networks for marketing. Of course, we had our social presence across the different platforms but even our own site didn’t show work. The mystery was helpful in getting into a room with potential clients to own the story of how we may be able to partner with them to help with projects or large initiatives.

How fast did the company grow during the first few years?
We doubled and tripled our staff, revenue, and profits nearly every year. The response to our offering and the team was incredible and led to all of the growth that we saw. The client roster stayed super diverse with work coming in from all types of sectors which helped us grow as well.

How do you define success?
Success is building a company with a culture focused on accountability and trust. That empowered our team to forge great relationships and trust with our clients. We wouldn’t be here today if it wasn’t for the team feeling that they had the ability to push themselves and be owners of their ideas and creative deliverables.

What is the key to success?
Trust, trust, trust. You don’t earn trust, you lose it. Giving someone the ability to own the work that they are assigned to complete and not getting in their way is tough as you have to skirt the line of overseeing and giving out sharp advice with micromanaging.

What is the greatest lesson you’ve ever learned?
Being an entrepreneur means that you are responsible for the livelihood of every single employee that takes the chance to work with you. That is an immense stress but the reward for creating a place that people are proud to come into everyday and give it their all is unlike anything I have experienced professionally before starting Wondersauce.

What are some of your favorite books?
The Hard Thing About Hard Things is a book that EVERY entrepreneur needs to read. Read it now, especially if you are a year or so into your journey. Ben Horowitz has an incredible way of sharing stories that are completely relatable no matter what industry you might work in.

Tell me about one of the toughest days you’ve had as an entrepreneur.
Every day is tough and wonderful at the same time. If you’re coasting, then your business is dying. Tough days can be ones where you sign five projects at the same time or tough days can be when you lose five projects you were pitching for. How you handle yourself to get through either scenario is what defines your success.

When faced with adversity, what pushes you to keep moving forward?
If this was easy, then everyone would do it. Adversity drives an entrepreneur. It gets you firing on all cylinders to come up with a solution to whatever the problem is. If this doesn’t sound like you, then you may want to reconsider your path.

What advice would you give to young entrepreneurs?
Start now. Don’t wait because the hardest thing to do is start, but you will never learn how to succeed and move forward if you don’t start.

Drew Millard – Founder & Principal, 33 Realty

Left to right: Eric Weber, Susan Beyler, and Drew Millard

A Professional Engineer (P.E.), Drew graduated from the University of Illinois with a degree in civil and environmental engineering. Drew spent the first eight years of his career, post-college, working in the engineering consulting field, while simultaneously building the infrastructure to launch a real estate operation. Drew managed and worked on some of the largest civil engineering projects around the country such as the Dan Ryan Expressway, Tri-Level Interchange in St. Louis, Monfayette Expressway in Western Pennsylvania, and I-80 throughout Northwest Indiana. Managing these billion-dollar engineering projects helped Drew develop superior skill sets in the areas of diligent project management and analytical assessments.

Starting with his foundation in project management and analytical assessments and drawing on his passion for real estate, Drew founded 33 Realty in late 2008. Drew’s vision of an integrated real estate services model, where clients can obtain all their real estate needs, has been accomplished as the company provides “Best in Class” services in the areas of leasing, property management and brokerage operations.

Drew is primarily responsible for the company’s property management operations. He is also uniquely focused on the company’s infrastructure to ensure that service levels remain impeccable as the company continues to grow. Drew understands that to stand apart in the relatively-saturated real estate industry, you must provide impeccable service and employ the most talented and professional individuals.

Tell me about your early career.
I went to school and earned a degree from the University of Illinois in civil and environmental engineering. Upon graduation, I went into engineering consulting, designing $1 billion+ roadway projects. While I have a ton of respect for my fellow engineers, I quickly realized this wasn’t going to be a lifelong endeavor for me. Then I read the book that forever changed the way I thought and frankly changed my life. Who knew Rich Dad Poor Dad would have such an impact? Shortly thereafter, I went out and bought my first investment property and things started to snowball. After buying that property I said to myself, “I know I can be a better real estate agent than the agent that helped me.” So I rushed out and got my license. While still working as a consultant, I would help my friends and colleagues find homes or investment properties and then I would turn around and buy more buildings with the money I was making on the side. Yes, the money was important to me but that was not my driving factor. The driving force was my passion for real estate. My wife knew how much I loved my second career so she called me every day at work asking me, “Have you quit yet?” So with a brand-new house, no insurance and a 2-month-old baby, I made the plunge. Looking back now, it actually seems a bit crazy but I had a foolish confidence at the time. With input from my wife and my future partner, Eric (who was my longtime broker partner), I wrote the business plan at my kitchen table and I am proud to say that seven years later, the full business plan has been realized. We are now a vertically-integrated firm, but we had to start building the individual business lines based on the economic climate at that time and with limited manpower. With the vision to have an investment real estate brokerage, leasing, construction, property management, and distressed real estate consulting business, we did the logical thing and concentrated on the business lines that would thrive in the collapsed real estate market of 2008. Leasing and distressed real estate consulting were the business lines that made sense to build because there was NO construction or investment sales happening in the continental United States. As my wife, Marta, and I were building those businesses, we knew we had to hire extremely-talented people which is extraordinarily hard when you don’t have an office, a website or any money. The only way to convince good people to “take the plunge” was to sell the vision which is now 33 and Cubed Construction. I look back to a pivotal moment in the business when a former investment banker applied to be a leasing agent at 33. I will never forget where I was, and I remember reading Susan’s resume on my phone. I remember thinking, “Why would a former banker specializing in M&A want to be a leasing agent?” There must be something wrong with her. Well, we met at an Italian restaurant for lunch the next day and we had a three-hour conversation about building the business, the vision for 33, our goals and how she would fit into the organization. It was obvious from that first lunch that we both shared the passion for building businesses and real estate. Of course, I couldn’t pay her to do any of this, so she helped build the infrastructure of the business with me while working as a real estate agent only making commissions. I literally didn’t pay her for the work and she was not a partner yet. Wow. Who does that? I thank God that we crossed paths because our firm would be light years behind where we are today without her selfless attitude. As our business grew and the economic climate started to change, it was time for my long time brokerage partner to take the plunge as well. Eric left a high-paying consulting job to follow his passion in real estate, just like Susan and me. There is a very common thread there. We all love what we do. With all three partners in place, we were off to the races. I look back at that moment as another pivotal moment to accelerate the growth of 33. Eric brought a tenacious drive, a refined attitude, and would accept nothing but the best. All together we had the manpower to launch our construction and investment brokerage business lines to complete the vertically-integrated concept. With all the business lines running in full force and providing cross selling opportunities for our firm, we started to experience exponential growth of our business. It definitely hasn’t been easy but I was proud to say that in 2016 we were featured in the “Inc. 500” as one of the fast-growing companies in the nation and one of the top 10 fastest-growing companies in Chicago. I look back at my career thus far and feel lucky that I was able to align myself with amazing people who share the same passion for building something special.

Where did the concept for 33 Realty come about?
I love real estate and I knew I wanted to have a real estate business. However, who would start a real estate business during one of the biggest real estate crashes in recent history? (A funny side note. My mom was scared to tell her friends that I quit a “safe” engineering job to start a real estate company during these times. She was sure all her friends would talk behind her back that I was fired or had lost my marbles.) During these times, I saw some of the most successful real estate tycoons of the time, who were singularly-focused, lose everything. By everything, I mean hundreds of millions of dollars worth of property and cash. It was horrible and I knew there was a way that I could create a business that could sustain and actually thrive in different economic environments. The strategy is such that the property management business is our annuity that will always keep the lights on and people employed. It’s a tough business but it is 100% necessary to accomplish the overall mission. The investment brokerage and construction platforms are very cyclical but provide a tremendous amount of the overall revenue when times are good. Then to further hedge our risk, we take our distressed real estate business very seriously because if we were to experience another 2008, the banking institutions trying to work through their distressed portfolio can keep all of our business lines stable. The other vision of the vertically-integrated model is to be a “one-stop shop” for real estate investment funds to buy, renovate, lease, manage and sell or hold a large volume of investment properties. We now have seen a full life cycle from the trough of the real estate market to the peak and are happy to report that our business model worked.

How was the first year in business?
The first year in any business has its trials and tribulations and mine was no different. In fact, I remember a very humbling conversation with my mom that I might have to sell my house if I don’t get an $800 transaction to the finish line. That is how thin I was running year one. I guess you could say ignorance was bliss back then because I do not recommend starting a business with little to no reserves! The good news is that I got to keep my house.

My primary focus wasn’t on growth at that time, even though the temptation was there because I was financially struggling. I learned early on that building infrastructure within a company that is already scaled could lead to a disaster. It’s really hard to go backwards and create systems after people are stuck in their inefficient ways of doing things. Our goal was build the launching pad in year one, and while it was scary at times, I am happy I did.

What was your marketing strategy?
Our marketing strategy is much like our business model. We use an integrated approach with digital, direct marketing, PR, print, signage and social media. The real key here is to understand the allocation of dollars between business lines given the economic forecast. Another strategy that we employ with success is cross-selling our business lines, as they all play well off each other.

What was growth like in the first few years?
We often grew at 200-300%, year after year, but when revenues are that low, it wasn’t all that impressive, honestly. Again, our primary focus was creating the plan and installing the systems so we were ready to scale. In 2012, with all partners in place, we started seeing some real growth in revenue.

What is the key to success?
A couple of things really jump out at me. First is a positive mind frame and vision for your company. Even when I went through the toughest of times in business, I did everything in my power to remain positive. A positive outlook and attitude is our primary core value. Second, I learned a lesson from my grandpa while doing landscaping for him as a young man. He was so wise and would tell me, “Anddddyyyyyy, work smarter not harder. Let the tools work for you, don’t work for them.” I took that life lesson from my grandpa and I try to apply that to everything I do. Of course I work hard, but if you work hard and smart, it’s a great combination for success. Let your tools, process, money, buildings, etc. work for you, not vice versa. Passive income is a beautiful thing.

What is the greatest lesson you’ve learned?
I still have a lot to learn, but you must approach different situations with different individuals in different ways. The people aspect of business is critical and the best entrepreneurs learn to master this. We’ve had consultants come in to work with our executive team, I’ve gone to seminars and I’ve read books. I’ve learned to shut up once in a while and really think about our approach with people to get the best results for the business. I’m an emotional guy so that isn’t always easy, but it’s necessary.

What are some of your favorite books?
I read a few hours every weekday so I have a lot of books that are on the top of my list, but here are the four that stand above the rest for me:
1. Rich Dad Poor Dad – As I said earlier, this book is what gave me the courage to start my own business.
2. Think and Grow Rich – There are many lessons in this book, but my primary take away was that you can accomplish anything with a positive mind frame, as the mind is a VERY powerful tool.
3/4. Fearless and Lone Survivor – Both Navy SEAL books and I greatly respect their drive, determination and selfless attitudes with their teammates.

What are some of the toughest parts of your day?
There is no question in my mind that my toughest days revolve around days when I am not getting along with my partners. Ugh! That is a mental and physical drain. This is why I say one of the best lessons learned in business is how to approach and read different individuals. I think we are all getting better at this and I am thankful. We still disagree with each other at times, but we work it out quickly and move on.

When faced with adversity, what pushes you to keep moving forward?
There are two motivations that really push me, and it’s centered around being a team. First and foremost, I am competitive and like to win. Nothing is more fun than winning after pushing through a tough moment in life. I’ve searched the recesses of my brain for the next answer as I’ve asked the question, “Why do I do this?” Beyond the passion for what I do, my main driver is that I never want to let anyone down. I will get through adversarial situations because I couldn’t live with myself if I let down my staff, partners or family.

What advice would you give to young entrepreneurs?
I could go on for days about advice for young entrepreneurs, but I’ll give a few key factors that helped me:
1. Value relationships over transactions – I work in one of the largest real estate markets in the world, but somehow we all know each other. When someone makes an unethical decision and burns a bridge, we all hear about it. Do the right thing, even though it might not be the most profitable for you in the short term. It will help you accumulate 10x more profit over your career.
2. Planning – I know this is MBA 101, but I can’t believe how many people don’t properly plan. They need to rush into a business or major decision because they lack patience. Seriously, sit down and take the countless hours to get your business plan together. Really think about it and the impacts of different economic climates. You don’t want to start the planning after you have a hundred employees and are burning the candle at both ends.
3. Don’t be selfish – A smaller piece of a bigger pie is much better than a big piece of a tiny pie.
4. Life balance – You are going to have to work a ton of hours, in the beginning, to build your enterprise. However, don’t forget about a little balance. Have some fun along the way and make sure not to lose sight of the really important things, like your family and friends.

Dave Meltzer – Co-Founder & CEO, Sports 1 Marketing

David Meltzer is the Co-Founder and Chief Executive Officer (CEO) at Sports 1 Marketing, where he utilizes his relationship capital and situational knowledge to secure diverse business opportunities for all of their clients and partners.

Dave has spent the last 25 years as an entrepreneur and executive in the legal, technology, and sports and entertainment fields with expertise across many industry verticals. He launched his career in sports at the world’s most notable sports agency, Leigh Steinberg Sports & Entertainment, serving as CEO, where along with Leigh and Warren, negotiated over $2 billion in sports and entertainment contracts.

Dave is an author and sought after motivational speaker. His books include Connected to Goodness and Compassionate Capitalism, both of which became international bestsellers. He sits on numerous boards including JUST Capital, OCTANe business incubator, Celebvidy, Rose Bowl Foundation, Transformational Leadership Council, Unstoppable Foundation, among several others.

Tell me about your early career.
I actually began my career in technology, working for companies like West Publishing, Accenture’s Everypath, and also worked in telecom as the CEO of Samsung’s first smartphone division. After my success in tech, I briefly retired and shifted my focus to investing. Unfortunately, I made some bad decisions, resulting in me losing everything and declaring bankruptcy.

Due to my technology background, I was asked to join Leigh Steinberg Sports & Entertainment as COO then CEO, where myself, along with super sports agent Leigh Steinberg (played by Tom Cruise in Jerry Maguire) and Pro Football Hall of Fame quarterback Warren Moon, negotiated over $2 billion in sports and entertainment contracts.

How did the concept for Sports 1 Marketing come about?
While working at Leigh Steinberg Sports and Entertainment, my business partner Warren Moon and I realized some of the shortcomings that occur in the agentry business. The business is very competitive and scarce, and when we started S1M we wanted to create a business that operated from the principle of abundance.

How was the first year in business?
When we started, we had a team of just three people: myself, Warren, and Scott Carter, an agent who we had worked with at LSSE. The first year was not easy and took a lot of hustling from all of us in order to get things done.

What was your marketing strategy?
We based our strategy on two things: situational knowledge and relationship capital. After my career in technology and Warren’s career in sports, we both had a wealth of relationship capital, giving us one degree of separation from any athlete, team, or business. We wanted to help bring together the right companies, people, and projects in order to make a lot of money, so that we could help a lot of people and have a lot of fun.

How fast did the company grow during the first few years?
One of the best bits of advice I got from Leigh helped the company to grow. Leigh always talked about the importance of being kind to your future self, and I took this idea and created an internship program around it. We helped to train future leaders in the sports business and our interns helped us to grow.

How do you define success?
I think success happens when you are truly enjoying the pursuit of your potential. Being inspired and enjoying the process of working towards a goal is success, no matter if you reach that end-goal or not.

What is the key to success?
I believe there are four principles that are key to both success and happiness: gratitude, empathy, accountability, and effective communication. Gratitude gives you a positive perspective on life. Empathy encourages you to forgive yourself, because you cannot give something to others that you do not have. Accountability empowers you to deal with anything that comes your way in life. Finally, effective communication helps you to connect to people and inspiration.

What is the greatest lesson you’ve ever learned?
The biggest lesson I’ve learned is the importance of asking for help from others. Be radically humble and ask people who are in a position that you want to be in for guidance. Unfortunately, I learned this lesson the hard way, losing millions of dollars simply because I was too full of myself to ask for help.

What are some of your favorite books?
Napoleon Hill’s Think and Grow Rich is probably my favorite book of all-time. I used to say that each time I read it, I made another million dollars. When it came time to write my own books, I went to the Napoleon Hill Foundation’s Greg S. Reid for help, resulting in two bestsellers so far.

Tell me about one of the toughest days you’ve had as an entrepreneur.
I think my most difficult day as an entrepreneur was when my wife confronted me about how I had changed and become entitled, telling me that she wasn’t happy anymore. If was also one of the most rewarding days of my life, and helped put me back on the right track.

When faced with adversity, what pushes you to keep moving forward?
I have always been a person who believes that what you’re made of comes out when you are under pressure. Besides, there’s only one person who can stop you, and that person is you.

What advice would you give to young entrepreneurs?
The first order of business for any entrepreneur is simple: do what you need to do everyday to stay in business. If your doors are not open, you cannot succeed. It is also important to surround yourself with the right people and the right ideas. Find the people that have the situational knowledge or relationship capital that you need and ask them for help. Most people will help you if they are able.