Shay Berman – Founder & CEO, Digital Resource

Shay Berman is the founder and CEO of Digital Resource, a full-service digital marketing agency. Shay’s clear-cut approach has allowed Digital Resource to land on the Inc. 500 list after just four years.

How did the concept for Digital Resource come about?
I was selling digital marketing services for another company door to door and had a few small clients on the side. I was actually thinking of starting a landscaping company when my dad suggested that I try to create a digital marketing company, instead. Landscaping is something I had done for years up in Michigan before I moved to Florida and I thought it would be great to get into again. I’m very happy he convinced me otherwise.

How was the first year in business?
The first year in business was a lot of learning what it was like to have a client for marketing and learn how to anticipate their needs, upsell them on additional services, and manage them to grow my own company, financially. There was a lot of downtime, because if you only have a few clients, there’s not too much to do. But sometimes all the clients will need something at once and it can be overwhelming. Every new client was a big milestone and I took advantage of every opportunity to grow my own company through networking, client referrals, and beginning my website’s search engine optimization process early on.

What was your marketing strategy?
My marketing strategy was mainly search engine optimization, but I knew that it would take some time to pay off so I had to use other avenues in the beginning. I found people who worked with other businesses and I worked with them in giving me referrals. They were happy to refer me as they knew the quality of my work and the success rates I have had with my clients.

How fast did the company grow during the first few years?
The company is really only four and a half years old, but we have had extremely fast growth for the past three years. Things grew pretty quickly from a solo practitioner’s standpoint in the first year and a half. It was impressive on that level but nothing that could be noticed by the public. As soon as we hired our first employee about a year and a half in, things really started to takeoff. I do not think it had anything to do with the hiring, but more to do with the fact that we were becoming more well-known. We went from $100,000 in revenue my first full year of business to $2 million just three years later.

How do you define success?
I typically defined the success of my company by how many people we touch. Whether it be the number of clients we have, the number of partners that entrust us with their clients, or the number of people we employ on our team, the more these numbers go up, the more successful I consider myself and my company.

What is the key to success?
The key to success is to be willing to work harder, longer, and smarter than everyone else you’re competing against, and you are competing against everyone. If you really want to be successful, you must be willing to give up everything and anything in the way of obtaining it. That means putting aside hobbies, relationships, and other things not crucial to the goal at hand, even if that sometimes means sacrificing sleep and other things that most people would consider “needs.”

What is the greatest lesson you’ve ever learned?
The greatest lesson I’ve learned is that owning a business is a massive responsibility. In the beginning, you think of how it can affect your clients if things go poorly, but as you continue to grow, you realize that the people you employ rely on you and the number of people that rely on those people is exponential. One wrong move as a business owner and you can affect the lives of hundreds, or even thousands.

What are some quotes that you live by? 
“There’s always a way” is the number one quote that I live by. I highly believe that there is a way to do anything. Whether by getting it done through pure force, extreme amount of time, or thinking about the problem in a different light to come up with a way to get things done that may be totally out of the box, there’s always a way to do it. Sometimes, what people don’t realize is that the problem at hand is only a small problem to the bigger picture. Finding a solution to the bigger problem can eliminate the need to solve the smaller one.

What are some of your favorite books?
Never Split the Difference by Chris Voss, Go for No!, and The Alchemist are my three favorites. Each one changed my life in their own way.

Tell me about one of the toughest days you’ve had as an entrepreneur.
One of the toughest days I’ve had as an entrepreneur, and these happen more often than you’d imagine, is when everything seems to be going wrong at once. Employees not executing or quitting their jobs, clients leaving, deals not closing, revenue growth stalling, capital needed to get into a new space, training needed for the team, not getting enough sleep, mistakes being made…I could go on and on. But the toughest thing is all of that happening and no one being able to help you. No one knows how it all feels, in your unique situation in your unique business with your unique services, clients, and employees. And no one can give you advice on a situation to which the bigger picture is too large to fathom. So anyone’s help is but a mere guess and you are alone trying to make the best decision on your own. The pressure is real.

When faced with adversity, what pushes you to keep moving forward?
The number one thing that pushes me to continue moving forward is the promises I made to myself and to other people out loud. People always say if you put your goals on paper you’re more likely to achieve them. But when you tell others about them, there’s accountability and people to hold you to those goals. Not having those goals would be a failure in my own eyes and in the eyes of everyone I have ever told. So the thought of failure in my eyes and to the world pushes me forward ever single day.

What advice would you give to young entrepreneurs? 
My one piece of advice to young entrepreneurs is to be sure they love what they do. If you don’t love what you do it will be impossible to overcome all the failures and obstacles that are thrown your way. If you truly want to be successful, you must make sure you start on the right path, by picking what it is you truly want to do, every single day, every single hour, every single minute, every single second, because it will never leave your mind.

Bill Robinson – CEO, Bridgewater Homes

Bridgewater Homes is a fast-growing semi-custom home building company providing distinctive homes in the Northern Colorado area. We are dedicated to quality, service, and craftsmanship.

As Chief Executive Officer for Bridgewater Homes, I lead company strategy and operations, bringing nearly two decades of experience in Real Estate Development and Finance.

Throughout my career, I have been a results-driven professional that seeks out new ways to help businesses work efficiently and effectively. In finance and business operations, it takes diligence and strategic planning to not only deliver quality products and services but also to create aggressive company growth and long-term financial success.

How did the concept for Bridgewater Homes come about?
From the time I graduated at Colorado State University in 1999, I had been in the real estate industry (commercial and multi-family). Then, in 2003, I started at Gehan Homes in Dallas, TX. For a little over a decade, I served as the Vice President of Finance for the company, during the fastest-growing homebuilding market in history, but also during the Great Recession in 2007-2008. So, I was able to see both sides of growth/success and decline/survival for not only a homebuilding company but also for a business, overall. During that time, Gehan Homes was named the fastest-growing homebuilding company in the U.S. in 2010, so we were able to operate decently enough during the downturn to come out of the other side on a positive note.

While we started to be very successful in 2010 for Gehan Homes, it was also the same year we found out my sister was diagnosed with terminal cancer. Growing up, it was just me and my sister, and since she was the closest with my mom, I knew that I would have to build my relationship with my mom since my sister would soon be gone…plus our father had passed in 2006, so it was just going to be me and my mom. Since I lived in Texas, I needed to find a reason to start going back to Colorado on a regular basis without it looking like I was checking in on my mom. So, in 2011, I reconnected with my friend from the late 90’s, Ben Broccoli, who was framing houses in Colorado and we decided to start building 1-2 houses at a time, for investment purposes. This would allow me to have a reason to come up to Colorado often and check in on my mom.

As we built 1-2 houses at a time and sold them to buyers, our houses became quite popular for their quality related to the prices. While we were doing these investments under the name, Brocc Builders, we continued to grow from 1-2 houses at a time to 2-3 houses at a time. Over the next few years, we became busy enough that we had to decide whether to keep this as a side business, or to make this a full time gig. With that said, I stepped away from my full-time job at Gehan Homes and we focused on building houses. In early 2015, we changed the name from Brocc Builders to Bridgewater Homes, in order for it to become a more marketable name.

What was your marketing strategy?
Really, it was getting the houses out to realtor groups so the buyers would come. It has now progressed to become more of a respected brand within the market, so we are spending a lot of time dealing with our website as well as billboards in the area.

How fast did the company grow during the first few years?
2015 – $0
2016 – $12 million in revenue
2017 – $30 million in revenue
2018 – Estimated to be above $50 million in revenue

How do you define success?
Business success is having a strong balance sheet and credibility with all partners (lenders, as well as trades).

Personal success is having fun and overall joy in what you do personally as well as professionally.

What is the key to success?
Find smart, creative, and hardworking people you can grow your company with, and listen to everyone. I’ve learned, from the top to the bottom of any company, everyone has good ideas on how to grow and/or how to save money. So, listening to everyone is essential for success.

What is the greatest lesson you’ve ever learned?
Have fun at work. Yes, there will be days that are hard, but if you don’t like going to work most days, you need to find something else to do.

Tell me about one of the toughest days you’ve had as an entrepreneur.
One of the toughest days is when you have everything laid out, everything you know will work, but don’t have the equity/financing for it. Being on pins and needles with creditors and waiting for their response. For us, when we were trying to put over 100 lots to really get things going back in late 2015, we sold our story to a creditor, but had to wait until they decided to move forward. To our company, it was a no-brainer it would work, but if they didn’t move forward to help us finance what we were doing, we were dead in the water. That was the toughest day we’ve had since really everything relied on their decision to finance us or not.

When faced with adversity, what pushes you to keep moving forward?
I just enjoy the challenge of making a balance sheet grow and get stronger. It’s like a puzzle. It has so many moving parts and so many short- and long-term decisions that can alter it. Really, I have fun doing it so, while there are always ups and downs, it makes it easy for me to keep doing this day after day.

What advice would you give to young entrepreneurs?
Make sure whatever you want to do, you love the concept. Don’t start a company in an industry, or some type of business, that you don’t love. Yes, there are other businesses I could have probably started that would have been quicker and easier, but I wouldn’t have loved it, nor would have enjoyed the process as much. Start by doing what you love, regardless of the industry, and you can make a ton of money. I tell people about my son’s first grade teacher. Teacher’s get a bad rap sometimes for being underpaid, which they truly are. However, she now makes over seven figures a year due to a teaching concept she turned into a national teaching strategy. So, she did what she loved, and now she is a millionaire. So, start out with what you want to do and love, and you will find ways to succeed at whatever level you want to be at.

Mike McKenna – President, Diamond Assets

Mike McKenna is the founder and president of Diamond Assets, the most trusted Apple hardware trade-up partner. He works with schools and other organizations to maximize the residual value of their Apple devices.

Before joining Diamond Assets, Mike was an Apple account representative, where he worked with school districts throughout Wisconsin to deliver technology to students needed to promote a digital learning environment.

He is a graduate of Eastern Illinois University and resides in Milton, Wisconsin.

How did the concept for Diamond Assets come about?
In early 2014, I was working as an account executive for Apple. I would visit schools and work with districts interested in buying EdTech devices for education. I saw that many of my customers were disposing of their old devices by recycling them and getting just pennies per pound, if that. Most of the devices from Apple were still valuable, but schools didn’t have an easy way to sell them. This is where the idea for Diamond Assets came to me.

How was the first year in business?
The company was founded in 2014, and the focus was on serving schools in the Midwest. Within a year, that expanded nationally. The first year involved a lot of long days traveling to meet with school districts and to validate our business model. Today, we serve schools in every state.

What was your marketing strategy?
Our marketing strategy has mainly been word of mouth and referrals. Our business development reps spend a lot of time meeting with district administrators and school boards to educate them on the benefits of trading up equipment and how they can get the most for their EdTech investment. Because of this educational approach, we have won the trust of many districts. We also have started building important alliances with district administrator organizations, and are working to educate the industry through thought leadership on topics such as total cost of ownership and the optimal time to trade-up devices.

How fast did the company grow during the first few years?
Revenue grew from $217,406 in 2014 to $43 million in 2017. We went from one employee to 120 employees during peak times.

How do you define success?
To me, success is setting audacious goals and then accomplishing them, even if others don’t think it can be done.

What is the key to success?
I believe there are three ingredients to success: passion for what you’re doing, a great product/service, and surrounding yourself with “A players” who are aligned with your vision. This last trait is really important. Our team has decades of experience in educational leadership, as well as former Apple executives and Apple engineers. Since we have this strong background and really care about helping organizations, the team is focused on delivering the best service possible.

What is the greatest lesson you’ve ever learned?
Every day brings new challenges so you can’t get complacent.

What are some quotes that you live by?
One of my favorite quotes is by Steve Jobs: “It doesn’t make sense to hire smart people and tell them what to do; we hire smart people so they can tell us what to do.” I really believe that businesses succeed when they hire really good people with diverse experiences, and provide an environment where their experiences and opinions matter.

Tell me about one of the toughest days you’ve had as an entrepreneur.
Security is very important to us, so we have implemented strong controls in our building and only hire workers who have been background checked. A couple years ago, we contracted with a temporary agency to provide workers to process devices with the promise that all workers would have passed a background check. We had a theft in our cafeteria one day, and were able to quickly access security camera footage to determine that the culprit was one of our temporary workers. I was shocked to learn that this person had a criminal background. We immediately canceled our contract with the temporary agency, as they clearly were not performing the required background checks. While this was upsetting, it also showed me that we had great controls in place to ensure the security of devices and the safety of our workers.

When faced with adversity, what pushes you to keep moving forward?
Now that our staff has grown, I feel responsible for more than just myself. I have staff who have families relying on the company for their livelihoods. That is a great motivator.

What advice would you give to young entrepreneurs?   
Take the leap and don’t have regrets. The biggest regret will always be not trying.

Andrew Josuweit – Co-Founder, Student Loan Hero

After graduating with $74,000 of student loan debt, Andrew Josuweit started Student Loan Hero in 2012 to help consumers figure out the best way to repay their student loans. He led the company as CEO until it was acquired by LendingTree in 2018.

How did the concept for Student Loan Hero come about?
I graduated with $74,000 of student loan debt in 2009, during a terrible job market. Over the next few years, my student loans ballooned to $104k at their peak. During my journey, I received terrible financial advice from my student loan servicers. Student Loan Hero was our solution to help consumers get better student loans and financial advice.

How was the first year in business?
Our first year was exciting, and exhausting. We were accepted into a business incubator called Start-Up Chile and received $40,000 USD equity free as part of the program. Our time in Chile was spent on competitive research, launching a minimum viable product, business development, and generally trying to find product market fit. By the end of year one, we were running out of cash, so I moved to New York City to raise an angel round. We failed to raise money due to low revenue traction, and we soon turned our efforts to ramping up internal marketing efforts, which ultimately allowed us to bootstrap our growth.

What was your marketing strategy?
Our primary strategy was content marketing. By 2018, we had 20 plus full-time employees on our editorial team producing financial education and content for our blog. Secondly, we further developed our marketing fly-wheel by spending millions of dollars on our paid, social, and email marketing efforts, as well as conversion optimization. At the end of the day, our high level marketing strategy was to provide consumers with the best tools and resources to quickly answer their financial questions.

How fast did the company grow during the first few years?
Our first year, in 2012, we made less than $10,000 USD. Our second year was around $40,000. After year three our growth was exponential, growing into eight figure revenues before we were acquired by LendingTree in 2018.

How do you define success?
Success to me is when you build a team that is engaged and excited about your purpose and journey. When you have a great team in place, you can produce great products and services that truly solve problems.

What is the key to success?
Working hard everyday, testing things, learning from mistakes, taking time to understand your customers, and keeping an open mind.

What is the greatest lesson you’ve ever learned?
You can be great at anything you want, it just takes time and energy. Most people don’t achieve their goals because they don’t put enough time and energy into achieving their desired outcome.

What are some quotes that you live by?
Work hard, have fun, and be kind.

What are some of your favorite books?
The Untethered Soul, The Alchemist, The Daily Stoic, and Scaling Up.

Tell me about one of the toughest days you’ve had as an entrepreneur.
A co-founder left the business in our second year, when we were failing and about to run out of money. We had to make a decision on whether to continue our journey and keep pushing the business, or to give up and quit. It felt like we not only lost a co-worker, but also a friend and a general belief in our company mission.

When faced with adversity, what pushes you to keep moving forward?
Fear of failure and mediocrity.

What advice would you give to young entrepreneurs?
Success doesn’t happen overnight – be patient, work hard, and try lots of things. I believe new businesses take 1-2 years to get early traction, and 6 years or more for significant returns.

David Barnett – Founder & CEO, PopSockets

In 2010, David Barnett was looking for a way to stop his earbud cord from getting tangled, and he achieved this by gluing two buttons to the back of his phone and wrapping the earbud cord around the buttons. As ugly as the buttons were, they worked. In the course of improving on the idea, he developed about 60 different prototypes, making the buttons expand and collapse via an accordion mechanism, so that they could function as both a stand and a grip.

In 2012, Barnett launched a KickStarter campaign for an iPhone case that would have two PopSockets grips integrated into the case. In addition to getting successfully funded, the KickStarter campaign enabled Barnett to show the world his dancing prowess. Two years later, in 2014, Barnett launched the business out of his garage in Boulder, Colorado, and has subsequently sold over 40 million PopSockets grips around the world.

How was the first year in business?
I launched the business out of my garage in Boulder in 2014.

What was your marketing strategy?
I had no money for advertising, so my strategy was to get as many PopSockets grips into people’s hands as possible, regardless of my profits, in order to create a critical mass of evangelists for my product. It worked.

How fast did the company grow during the first few years?
In 2014 we sold roughly 30k grips, then 300k in 2015, 3M in 2016, and 35M in 2017. This year, we’ll sell around 50M. We’ve grown to 170 employees in offices in Boulder, San Francisco, Finland, and Singapore.

How do you define success?
By the amount of positive impact we make in the world.

What is the key to success?
Think outside the box. Question conventional wisdom. And hire great people.

What is the greatest lesson you’ve ever learned?
Focusing is overrated. I prefer the shotgun approach to see what sticks. I would never have had the success I’ve had if I had focused on solid colors in year one, then graphics in year two, then customs in year three. The business would have failed. I started out of the gate with customs and plenty of graphics, and that’s what resonated, I learned.

What are some of your favorite books?
I’ve read few books in my life, none on business. Perhaps my favorite is Bertrand Russell’s The Problems of Philosophy.

Tell me about one of the toughest days you’ve had as an entrepreneur.
One summer day in 2014 when we had around $8,000 in the bank, I’d spent all my savings and all my investors’ money, and we received our third consecutive order of 100% defective product.

When faced with adversity, what pushes you to keep moving forward?
Some sort of illness/obsession, I suppose.

What advice would you give to young entrepreneurs?
Find the right level of confidence, enough to keep you going in the face of failure and skepticism, but not so much that you’re deaf to what the world has to say about your product and your business.