Paul Weinert – Founder & Principal, GRAYBOX

Paul Weinert has been working with companies to develop their digital strategies for over a decade. Before founding GRAYBOX in 2009, Paul enjoyed a successful career as a user interface designer and eCommerce business consultant. He has helped businesses use digital technologies to increase revenue, streamline operations, and present themselves better, including personally overseeing the launch of 100s of websites and apps.

Paul graduated from the University of Oregon with a Bachelor of Science in journalism in 2006, with minors in computer science, political science, and public speaking. Paul is married to his delightful wife, Lydia, and has two amazing and energetic, young sons: Aaron and August.

Tell me about your early career.
I started my career as a writer, photographer and graphic designer for a newspaper. I was really into page layout and found myself working for various agencies as a freelance graphic designer in college. At one of them, they said they didn’t need a print designer, but they needed someone who could code websites, so I started doing that. I’ve always been a tech nerd and had grown up coding, building computers and helping others with technology problems, so I started designing and building websites as well.

After college, I moved from web design to user interface design, focusing more on the business and how a digital system can solve business problems than on the look and feel of the site or application. I started working at an Internet business consulting at a firm near Seattle and lead their UX, eCommerce and marketing practices for around five years.

How did the concept for GRAYBOX come about?
The company we are today is very different than when we first started. I call them GRAYBOX 1.0 and GRAYBOX 2.0.

For GRAYBOX 1.0, I started the company right at the start of the recession (early 2009) as a way to combine all the super talented and out-of-work marketers, designers and developers that I was meeting all over Portland and Seattle. I figured that if I could get everyone to come together to form a collaborative network that I called GRAYBOX, we could compete with other full-service agencies by providing a better product at a lower cost than everyone else. Basically, using the supply-side excess of the recession to create a competitive advantage.

This worked great for four years, then the recession started getting better in 2012, so I saw my network decimated by everyone taking full-time gigs at the agencies and companies that were hiring up for marketing again. As such, I had to pivot to GRAYBOX 2.0.

This next phase has been us moving into more of a traditional firm model. We have staff and we work with our client partners to solve business problems with digital solutions in both the marketing and operational sides of their businesses. Since we pivoted, our growth has just exploded and we’re in our fifth year of this model.

How was the first year in business?
Rocky. It was hard to get people to talk to me too, so it was all about taking a scrappy approach to finding work, a lot of blind RFP responses, and investing in our long-term marketing presentation. Turns out that focusing on our marketing presentation was a great bet, as we were able to appear larger than we were and had great SEO placement pretty early on.

What was your marketing strategy?
Be everywhere online and track everything.

If you searched for websites or digital marketing, we were there. I was in every company directory, every ad placement or online marketplace I could find. I then tracked EVERYTHING with a granular tagging structure, so I could tie it back to lead volume, lead scoring, and my sales close rate. Everything was a test, and I was ruthless about paring back with what was non-performing and doubling down on what was working well.

For example, when I started using AdWords, I initially paid for 650,000 different keyword combinations, and I was committed to eliminating at least the bottom 50% of them, based on their performance each month. Within a year, we were bidding on only the best 150 best terms. Today, as we’ve expanded our practice, we bid on around 100 terms, but it remains very results-focused.

The best marketing strategy, to me, is one that is measurable and consistently produces effective results.

How fast did the company grow during the first few years?
It was fairly small throughout all of GRAYBOX 1.0. I was the only employee and I did all of the sales, account and project management.

Then, with the shift to hiring employees and operating under a more traditional model, we starting growing very quickly. In the last five years, we’ve grown around 181% annually by headcount, and more than that by top line revenue.

Our first office was 120 square feet. and I had to break my six month lease on that space because we outgrew it so quickly. We had one desk and three of us shared it, and whoever was the last person in, sat on the couch.

Our second office was 900 square feet, and it felt gigantic. We had our own meeting room and I had a private office for a few months. Again, we had to move out of that after eighteen months (breaking another lease) because of our growth.

Our third office was 3,200 square feet, and it felt so luxurious. We had multiple meeting rooms and private offices, but by the time we left two years later, all of the offices were gone because we needed them for meeting spaces, and there was always a queue for the restrooms.

Our current office is massive at 11,000 square feet, and we’ve built it out for 85 people. Currently, we’re at 47, so we expect to be here for a few more years.

How do you define success?
I think a lot about balance and health, lately. I think our success is directly tied to the health of our client partners’ businesses and how our work contributes to that. That’s first and foremost.

In addition, we want our team to live balanced lives and to achieve success in a way that’s good for everyone involved — partners need a great product and experience, staff needs to feel empowered, challenged and excited by their work, and as a business, we need to be financially healthy.

What is the key to success?
Being good to people. Relationships are the key to everything in professional services. Personally, it feels like I’m dating 100 people at once, between staff and our partners. We earnestly care about our partners and team, and I strive really hard to get my team to truly live out the mission of a servant, to selflessly make our partners’ businesses better.

It sometimes hurts to be super good to everyone, but I’ve found that when you are truly on another person’s side, they feel that care and we can form a great bond that serves everyone better.

What is the greatest lesson you’ve ever learned?
One thing I think about a lot is this quote from Steve Jobs:

“When you grow up, you tend to get told the world is the way it is, and your life is just to live your life inside the world. Try not to bash into the walls too much. Try to have a nice family life, have fun, save a little money.

That’s a very limited life. Life can be much broader once you discover one simple fact, and that is – everything around you that you call life, was made up by people that were no smarter than you. And you can change it, you can influence it, you can build your own things that other people can use. . . . Once you learn that, you’ll never be the same again.”

I love this and it’s very motivating to me. We can change things, build things, and make life better for ourselves and for others.

What are some of your favorite books?
I like to read, and I generally have at least a few books going at a time.

BusinessManaging The Professional Service Firm by David Maister. It’s an older book, but it’s full of wise gems about running a knowledge-based firm.

Nonfiction — Anything about economics, biographies, the environment, or general life lessons. Some of my favorite authors are Michael Lewis, Malcolm Gladwell, and David Sedaris.

Pleasure — Anything that builds a good world and I can get out of my head for a while, including Lord of the Rings, Game of Thrones, Ender’s Game, Harry Potter, and Mistborn.

Tell me about one of the toughest days you’ve had as an entrepreneur.
I don’t have a lot of tough days. I love what I’m doing and our team is amazing. There’s just a lot of crazy days! I’m always pulled in a hundred directions, so it’s always an exercise in prioritization and picking what I will succeed and fail at each day. It’s part of the curse of fast growth for sure, but it’ll get better.

When faced with adversity, what pushes you to keep moving forward?
My commitments to my client partners and my team, no question.

I started the company, but we’re building it together and I owe it to them to keep going and do my part. They trust me and depend on me to get it done. That’s a huge responsibility, and I need to honor that trust and fulfill it. This is true for our team, as well as for our partners who hire us to make their businesses better.

What advice would you give to young entrepreneurs?
Don’t be afraid to dive in and figure it out along the way. Everyone is amazing at a few things and weak in many things. So live off your strengths and shore up your weaknesses one at the time.

I think so much of business comes down to three things:

  1. Be okay taking a calculated risk on a good idea.
  2. Be good to people and be a good citizen in your community.
  3. Be consistently improving your weaknesses.

Arthur Souritzidis – CEO, Momentum Solar

Arthur Souritzidis is the chief executive officer of Momentum Solar, one of the nation’s fastest-growing, privately held solar energy companies.

Arthur joined Momentum in 2010, became a partner in 2011, and then CEO in 2012. He quickly transformed Momentum from a local New Jersey business to a top tier national player. Momentum’s footprint servicing homeowners and business owners now expands into New York and Southern California, with plans for several additional territories earmarked for the near future.

Momentum Solar, which has grown to 550+ employees since its inception, was named on the 2016 Inc. 5000 list of America’s fastest-growing private companies, and was one of Solar Power World’s Top 500 North American Solar Contractors. More recently, Arthur was recognized by Forbes as one of their “30 Under 30 Energy” entrepreneurs. According to Forbes, Arthur stood out as one of “The Best Minds Planning How to Power Our Country”.

A graduate of Montclair State University with a degree in finance, Arthur’s entrepreneurial spirit has been instrumental to Momentum’s rapid growth and the creation of advanced solutions in the clean energy sector. Arthur became a student of the industry, analyzing federal and state solar incentives and quickly identifying proprietary commercial financing solutions, which became the foundation for Momentum’s future success. Arthur believes in the importance of the green energy movement to boost the U.S. economy virtuously by not only creating jobs, but also by serving as a steward for the environment.

Tell me about your early career.
I actually haven’t had much of a career outside of solar; this company, specifically. I was exposed to the industry immediately after college. I had studied finance at Montclair University with the intention of working on Wall Street, but ended up graduating during the depths of the economic recession. The clean energy space, however, was showing growth during this time and it had always peaked my interest.

I ended up meeting Cameron Christensen who was the sole proprietor of a small solar company, and it was then when I identified an opportunity to help bring solar power to the mass market. I joined forces with Cameron and took over the sales process while he focused on operations. I became a student of the industry and helped engineer a profitable product within a few months. With evidence that my financial expertise was enhancing the business, I truly wanted to see the business takeoff, and ended up earning 50% ownership the following year. It’s been an upward climb since.

How did the concept for Momentum Solar come about?
Cameron started what is now Momentum Solar back in 2009, after moving to New Jersey from Utah. He had an extensive background in field operations with some experience in solar, and was literally handling everything from the sale to the permitting, design, engineering, installation and activation of every system he sold. He launched his business after a few years of installing, because he saw the economic opportunity in it.

I met him within that year, and together we established an operational process that remained lean for many years until we were in a financial position to expand the business. In early 2016, we started to steadily grow our workforce, rebranded, and launched Momentum Solar as you know it today. We went from a four-person company to a nationwide solar firm generating nine figures in revenue.

How was the first year in business?
The first twelve months were difficult, to say the least. My partner and I were in a perpetual state of biting off more than we can chew, and quickly learning how to chew it. All of the business’s equity is held among its partner base, which is a great blessing today, but it was cause for an agonizing first year. We fought to compile sales and marketing channels, operational capabilities, and installation capacity strictly with the cash that the business was generating organically.

Truth be told, I worked free for a couple of years. But with determination, inspiration of a better energy future, and careful selection of the right vendors and supply chain, we started seeing results.

What was your marketing strategy?
To be honest, at the time we didn’t really have one. We were reliant on networking and maintaining relationships to coordinate sales appointments. I had some experience in sales prior to solar, and a passion for the product. We depended on what we were selling, how we presented it to the potential customer, and word of mouth.

How fast did the company grow during the first few years?
Our company growth was slow but steady, and eventually we found ourselves in the position to greatly increase our impact on both the environment and our customer base. Our management carefully established operational foundations to fine-tune our business process and position us as a notable solar company in a highly competitive industry. We made the decision to not grow on debt, but rather on previous profits to fuel future organic growth. This kept us grounded and determined to reach our goal. By the end of 2015, we had built a well-oiled machine with the ability to start investing more into sales, marketing, and experienced management. By the end of 2016, we were recognized as one of the fastest-growing private companies in the nation and a top solar contractor throughout North America.

How do you define success?
Success is about aspirations and setting goals to achieve, but it’s also about appreciating the journey to get there. You must always be consciously involved in the ongoing process of reaching your full potential. It’s important for me to be able to look myself in the mirror every day and have no regrets about the path I’ve chosen. When faced with hurdles, do not recognize failure, but rather persevere and have the motivation to keep going.

What is the key to success?
Success in business is about the right thoughts and the right team. Without having your head in the right place or conviction in your platform, you’ll have difficulty finding others to follow your vision. Positive thoughts are paramount, and passion resonates.

What is the greatest lesson you’ve ever learned?
The greatest lesson I’ve learned was outside of the business directly. It’s the simple reality that you have to give in order to receive. There are so many ways you can give, whether it be your time or your money, but really I think it should be a component of both. In business, it’s about helping my employees achieve their goals. In life, it’s about helping the less fortunate. Maybe, it’s a different perspective but I really believe, in a way, that generosity is the key to success.

What are some quotes that you live by?
“If you see it in your head, you’ll hold it in your hand.”

What are some of your favorite books?
Think and Grow Rich by Napoleon Hill was really the foundation of my mental conditioning of which I attribute my success. It’s implied in the title, but the concepts of the book truly help you enforce the power of positive thinking.

Tell me about one of the toughest days you’ve had as an entrepreneur.
I will never forget this. It was my first year in the business, and a significant commercial project with an executed contract somehow slipped back into attorney review. The client’s attorney was dead set on killing the deal. We had already taken possession of the materials, spent all the money we had, and were in the early stages of the development of the product. The distributors were taking a chance on me and I was approved to borrow way more money than the business should have been eligible for. I felt like I had been gutted.

In the preceding weeks, there were times that I felt helpless, hopeless, and had to remind myself to have confidence in my goals. With hard work, diligence, perseverance, and perhaps all else, conviction, I would get through this. I remember driving by the project one day, gripping the steering wheel until my knuckles were white and visualizing that solar panels were on the roof of the property. From that moment, I set my anxiety aside and focused on solutions. Ultimately, we satisfied the attorneys and received the approvals to proceed. It was the hardest time I had ever been through in business and one of which I learned from. It led to one of the most gratifying victories of my career.

When faced with adversity, what pushes you to keep moving forward?
The big picture. With every hurdle that comes with running a business, I am always determined to power through. I realized early in my career that business is largely a series of problems, and those who work hard to achieve a way to solve these problems are the ones who are successful. When you realize this pattern and formula, it’s inspiring as you become aware that there’s a differentiating component to what separates the good from the great — people who do well in life, and others who just skate by.

What advice would you give to young entrepreneurs?
Eliminate doubt from your thought process. Success only exists in the absence of doubt. This is easier said than done, as doubt is an inherit character flaw that we all possess — but we can all overcome it with mental conditioning. When your steadfast convictions and confidence replaces doubt, you will have success. Consider your obstacles as stepping stones towards that success.

A technique that I have found to be helpful when a task felt overwhelming and that day-to-day seems impossible: Focus on your end goal. Have confidence in your goal and what you will achieve, even when you don’t know how to get there. Life has a way of engineering how to reach that goal.

Jerry Brazie – Founder & President, Senvoy

Jerry Brazie is a serial entrepreneur who comes from a very poor and rough upbringing. The seventh child out of nine, Jerry’s family survived on food stamps and government assistance for much of his early childhood. His family (of eleven people) lived in a three-bedroom house, with one bathroom. Jerry’s first job was at eleven years old, washing dishes at a local restaurant, steadily moving up from one job to the next, always leaving for better pay. Surviving violent teenage years, Jerry is fond of saying that at age eighteen, he was certain he would not survive to age twenty-five.

With no education and no prospects for the future, Jerry took a job as a local messenger, delivering packages and paperwork, starting at the age of twenty-one. With a gift for operational efficiency, Jerry was running all of the dispatch operations for the company, and was instrumental in its growth from $2 million to $5 million in revenue within two years. After managing that company for six years, at twenty-eight years old with a infant son at home, Jerry was approached by investors to start a new company.

He took the offer and the company failed within a year, so Jerry went into business for himself. With no education or business training, but street smart, Jerry grew his business to $14 million in revenue within the first four years. Twenty years later, Jerry still operates that business, along with many others. He has owned multiple gas stations, car washes, convenience stores, a real estate development company, has developed 100s of lots that were sold to national builders, built houses, and also owns and personally manages over 130,000 square-feet of commercial real estate in multiple locations in Portland, Oregon. He has a management company, as well as a driver management company. He has purchased four of his competitors over the years, as well as bought and sold multiple other businesses.

Jerry’s newest passion are the daily videos he publishes on YouTube and Facebook. With a lifetime of experience and stories, combined with owning companies that have generated over $330 million in revenue over the last twenty years, Jerry sees this as a way to give back. In the videos, Jerry shares strategies, real life experiences, and advice on how to live a successful life. The goal is to inspire people to reach beyond what they think they are capable of by showing them how to break through barriers, both mentally and physically. He sells nothing and charges nothing, but tries to show what it takes to be a successful business owner, both the good and the bad. Straightforward and direct, Jerry’s story is the epitome of the American Dream.

Jerry has been married for twenty years and is the father of three children. An avid outdoorsman, Jerry hunts all over the world whenever he can.

Tell me about your early career.
I come from a very poor background, and was number seven (out of nine kids). So, when you grow up in poverty, with that many siblings, you do everything you can to get out of the house and work whatever jobs you can find. I started working at eleven years old as a dishwasher at a local restaurant, graduated to IHOP, then McDonald’s, and every job in-between. The key was that I constantly left one job for a better-paying one, until I eventually landed at a courier company, where I was managing the dispatch operations within six months. That’s how I got into the transportation industry.

How did the concept for Senvoy come about?
I was approached to start a new company by an investor. He knew of me because I had worked with many dispatchers in the area, and had helped build the largest company of its kind in Oregon. I remember, clearly, sitting in my office and he sent me a pro forma, and I had no idea what I was looking at. I led this very busy company for years, but only operationally. I knew that side of the business, cold, but had never seen the numbers.

And that is when I had an epiphany. I was twenty-eight years old and had been managing employees much older than I was, for years. I was the hotshot, operationally, but I had no idea what I was looking at. I had never heard of a P&L or a balance sheet, and I certainly did not know how to read them. So, I was sitting there and it hit me. I thought to myself, “I had better shut up and listen, or I am going to be doing this for the rest of my life.” Right then, I started buying every book on business, I ditched a bunch of my friends, I started hanging out with people who were smarter than me, and I took the investor up on the job offer.

How was the first year in business?
We did $3 million the first year, but the investor did not have the money to finance the cash flow. I was learning on the fly and was not experienced enough to figure out what was happening. I sold like crazy, but I wasn’t making any money. I learned that it is easy to sell, but very difficult to make money. One year to the day, the investor fired me.

Not one to back down, and armed with a bit of experience, I made plans to start my own company. However, I had no money, so I used what I did have: an excellent reputation as a straight shooter. So, I used that as currency, and I went to my five largest clients and told them what had happened and asked if they would prepay me for the first year. I was five for five. This is why I tell people all the time that the only answer to a question not asked is no. I have never been afraid to ask.

What was your marketing strategy?
Me. I had all the contacts, so I went to all of them and made sales. Most of the work came from the company that had fired me. I was a bull in a china shop, and I never hesitated for a minute to ask customers for their business.

How fast did the company grow during the first few years?
So, I started my own company with my customer’s money, and I did $3 million, $6 million, $10 million, and $14 million, during the first four years. It was at this point when we had to learn to make money, because I was bleeding at $14 million. So, I cut it down to $8 million, got our hands around it, and here we are, twenty years later.

How do you define success?
Learning. I come to work every day, knowing that we can go out of business because of the decisions I am about to make. So, I try to learn something from every situation. I am successful because of my adaptability, introspection, and lack of emotion. If someone can learn all three things, they are successful.

What is the key to success?
Easy. Hustle and outwork everyone, every time. There are a lot of hardworking people digging ditches, so you have to hustle for the business as hard as you work for it. I work fifteen hours a day, and have for twenty years. But I will outwork every competitor, no questions asked. I am also patient and think long-term. I also didn’t quit when it got hard. And finally, no emotion. I do not get up or down throughout the day. I enjoy the wins, and hate the losses, but that is for just the quickest of moments and then I move on. You can’t get too high on yourself or else you are heading for a fall.

What is the greatest lesson you’ve ever learned?
Independence. The understanding that no one was going to help me and I was on my own. I was sixteen years old or so, and had gotten in a fight at a local mall with four guys. They put it to me pretty good, breaking my nose and leaving me under a bus stop bench. It took me two buses and a one-and-a-half mile walk to get home. About a third of the walk home, I was holding my nose and I remembered I had little to go home to, because we had nothing, and then I had the first of many hard lessons. I learned that no one at home was going to help me anyway, and if I wanted to survive, I had to do it on my own. To this day, I can still remember the feeling I had when I came to that realization. It guides me to this day.

What are some quotes that you live by?
“Don’t be afraid of change. You have to burn the ships and move on.” “Run, don’t walk, to a problem. Seek it out, pound it into submission, and dare it to happen again.” “The answer to every question never asked is always no.”

What are some of your favorite books?
Washington: A Life by Ron Chernow
The Great Bridge by David McCullough

Tell me about one of the toughest days you’ve had as an entrepreneur.
Easy. In 2004, my partner who had helped me start and grow the company, and who also kept the books, decided that the company was going out of business because we were struggling. So, he quit collecting money, quit paying the bills, and took a job with my largest competitor at the time. Two days after suddenly quitting, I received a call from his boss, the owner, telling me that he understood the company was in trouble and offered me pennies on the dollar for it. I hung up, went to the office, told my management group what had happened, and all of us dedicated ourselves to fixing the company. Why? Because fuck him, that why. We weren’t going to lose, so I worked twenty-hour days, we pushed our collections and negotiated our payables, and we brought the company back from the edge within six months.

That was 2004. Jump forward to 2013, and I participated in the bankruptcy auction for that company. Sucks to be him.

When faced with adversity, what pushes you to keep moving forward?
I refuse to lose. I know that is a cliche, but some of us live it every day. I climbed out of the gutter, with no education, stealing food to eat as a kid, have seen four murders and three suicides by age twenty-one, worked twenty small-time jobs, all to get where I am. Adversity? It’s easier than stealing food and fixing a broken nose. I hate to lose and I never lose perspective.

What advice would you give to young entrepreneurs?
Three things:

1) Know your numbers, know your numbers, and lastly, know your numbers. Pay attention only to the bottom line. Sales are easy, but making a profitable sale is hard. So, don’t get all excited when that top line grows, get excited when the bottom one does.

2) Outwork everyone. There is no work/life balance for entrepreneurs. You have to work harder than your competition. There are no shortcuts around this. If you are not willing to sacrifice and put in the time, don’t do it. Nothing will come to you. You have to hustle.

3) Money follows, it does not lead. Don’t let it. Do the right thing, take care of your people, and operate with integrity.

Kevin Gelfand – Co-Founder & President, Shake Smart

Kevin Gelfand is co-founder and president of Shake Smart. During his junior year at San Diego State University, Kevin and his business partner, Martin Reiman, came up with the idea for Shake Smart, which started as a way to just learn how to start a business. Six years later, the company has 130 employees, eight locations stretching from California to Texas, and large expansion plans for 2018.

Kevin enjoys living an active and healthy lifestyle and thrives off competition, problem solving, and innovating. He is married to his wife, Jazmine, who has supported him with Shake Smart since the inception. Throughout his time as president of Shake Smart, he has received valuable mentoring throughout the community, and is determined to pay it forward to aspiring, career-driven individuals. He serves as a mentor to the Lavin Entrepreneur Program at SDSU, and spends significant time mentoring some of his leadership team to further enhance their skills as leaders and young professionals.

Tell me about your early career.
Well, I am not too deep into my career, as I started Shake Smart when I was a junior at San Diego State University. Prior to that, I was a waiter since I was fifteen years old. Before I started Shake Smart, I did have a few business ideas that never came to fruition, which I think all lead me to Shake Smart. I wanted to start a hybrid taxi service company, which failed because I didn’t have the capital required to start it (and I’m glad because Uber would’ve crushed me). Then I wanted to start an alcohol delivery service so people wouldn’t drink and drive. I quickly learned that you can’t start an alcohol business when you’re not of the legal age to drink. My last idea before Shake Smart was to start a discounted package deal where you get one of each major sporting event ticket from the city you are located in (i.e. Lakers, Dodgers, Chargers, and Kings) which would be a great gift for a girlfriend, boyfriend, husband, brother, or daughter. This idea failed because I couldn’t get a buy-in from the Lakers.

How did the concept for Shake Smart come about?
I was a student at San Diego State University, and an avid gym-goer. I had moved further from the campus, but still wanted to exercise at the campus facility. It’s important to get protein within 30 minutes of finishing a workout and I realized by the time I finished by workout, got to my car, drove home, and made a shake, it was outside of this 30-minute window. That was when the “Aha!” moment came, to combine the customization and convenience of the blended drink industry with the innovative benefits of the nutrition industry.

How was the first year in business?
A big learning experience! I was working 80 hours a week in the store, while also going to school full-time. My partner and I would tag each other in-and-out for class every day. We didn’t even know what we were doing, so it was tough to have staff there alone when we had nothing to train them off of. Year one was the “figure it the f*ck out year.” Every year has been a different emphasis for us.

What was your marketing strategy?
Convenience and affordability. It was important for us to be located right outside the gym so that it was convenient for people to purchase, and around the same price for them to do it themselves. If we can align those two components, why would anyone get their post-workout nutrition anywhere else? We spent almost nothing on marketing and still don’t, to date.

How fast did the company grow during the first few years?
After the first six months, Shake Smart quickly became one of the most popular options on campus. After the first year, it went from being a way for us to learn how to start a business, to a business we could actually grow. Our second year was dedicated to systematizing everything for growth. Our third year, we opened three locations in three months and spent a lot of time fine-tuning the system, learning from different customer types, figuring out our exact growth strategy, etc. By the start of year four, we were confident we had a fine-tuned, well-branded company that was ready for a much larger expansion.

How do you define success?
Trick word. I don’t think I am successful yet and won’t ever think I am successful. I believe the word success aligns with stagnation. We are always reaching to be successful. If you ever actually grab it, then what motivates you next?

What is the key to success?
The key to success is to always be trying to get to that point, and to always try and get to that point, you must be always enhancing. The earth moves at a rapid rate (literally and physically). Everything around us is improving and enhancing and if we don’t do the same, we will get left behind. Never settling, that is the key to success.

What is the greatest lesson you’ve ever learned?
Hard to pinpoint one. I have learned (and am still learning this) to understand what is in my control and what is not. You can only control what you can control, so stressing about the other things will only drive you crazy. I have learned that surrounding yourself with the right people from an employee standpoint and an advisor standpoint is the only way you will truly achieve greatness. I have also learned that being a truly good and genuine person is always going to take you farther, whether that is on a business level or on a personal level, with how you look back and see how you achieved what you achieved.

What are some quotes that you live by?
“Luck is when preparation and opportunity collide.” – Seneca
“Enjoy the journey.”
“Think different.” – Steve Jobs
“Here’s to the crazy ones — the misfits, the rebels, the troublemakers, the round pegs in the square holes. The ones who see things differently — they’re not fond of rules. You can quote them, disagree with them, glorify or vilify them, but the only thing you can’t do is ignore them because they change things. They push the human race forward, and while some may see them as the crazy ones, we see genius, because the ones who are crazy enough to think that they can change the world, are the ones who do.” – Steve Jobs

What are some of your favorite books?
Hands down, my favorite book is How to Win Friends and Influence People. I also love The 4-Hour Workweek, Good to Great, and Built to Last.

Tell me about one of the toughest days you’ve had as an entrepreneur.
For one of our newest locations, I hired a contractor who I thought was an honest person and who would do the job the right way. Out of good faith, I gave him the last installment early as he “needed it” to order final supplies. After I paid him, he bailed on the project and left me with a half-finished store that was supposed to open in seven days. I spent almost an entire week of sleepless nights trying to get it finished. I also spent $50,000 over budget because of the things the contractor did/didn’t do, and I felt I let down the campus that we had partnered with because they knew of all the issues that came up. Once I got through the fire, I realized a few things. It was a great learning experience (an expensive one) on how to better vet partners and follow standard procedure, and I felt my relationship with the university actually got stronger from it all because they saw how committed we were to staying on schedule and not letting such a terrible thing stop us from moving forward.

When faced with adversity, what pushes you to keep moving forward?
Accomplishment. I love the feeling of problem solving, so I think about that feeling when I am in the weeds to help drive me to get out.

What advice would you give to young entrepreneurs?
Determination, think differently, and always, always enhance.

Jim Prendergast – Founder & CEO, 317 Ventures

Helping others realize their full potential – whether as an entrepreneur, a young person in the business world, a father, a husband or a friend – Jim Prendergast admits that his favorite moments are those spent coaching, guiding and inspiring others. Leading with experience, heartfelt inspiration and a desire to share his life’s most teachable moments, Jim founded 317 Ventures in January 2017, marking a new chapter in his long business career.

After founding HealthiestYou, an innovative digital health company in 2011, that he sold in June 2016 to Teladoc, the nation’s leading provider of tele-health services, in a deal exceeding $155 million, Jim is now taking his experience as a serial entrepreneur and his personal passion for improving people’s lives to a new level. By helping position young, startup companies for success, Jim started 317 Ventures to use the business lessons he learned along the way, and is channeling his penchant for personal and professional coaching to fulfill his lifelong dream of helping others fulfill theirs. The company also leverages Jim’s 20+ years of building his own businesses – in financial services, insurance, employee benefits, and healthcare – to connect
innovative health and wellness companies with investors and financial opportunities to help them grow and prosper.

Throughout his years as a budding entrepreneur, Jim built his companies by focusing on creating a positive company culture and shaping entrepreneurially-minded teams that were invested in their own success to help the company succeed. That approach, a key factor in his business success strategy, is one that he applies now to help grow his clients’ companies. Along with building a people-first workplace culture, Jim’s personal investment in the success of others has built his reputation nationally as strong and compassionate business leader.

In June 2016, Jim was named a finalist in the Consumer Technology category in the Ernst & Young Entrepreneur of the Year Awards for 2016. His company was also recognized with accolades, such as the Arizona Central “Top Company to Work for in Arizona” award and the Phoenix Business Journal “Best Places to Work” award. He also took HealthiestYou’s national ranking from #846 in the Inc. 5000 list of America’s Fastest-Growing Companies in 2015, to #397 on the Inc. 500 list in 2016, as well as to #34 on the exclusive 2016 Entrepreneur360™ list of the Best Entrepreneurial Companies in America as determined by Entrepreneur Magazine.

Jim speaks at health industry and leadership events nationwide. He has been featured on an episode of “Men’s Health Live,” the Radio Network of Men’s Health Magazine, and was a guest on the ShiftShapers’ podcast hosted by industry thought leader, David Saltzman. He previously was a speaker on a national, business success tour, as well as a regular on the “Extreme Money Makeover Tour,” and the co-host of a major market radio talk show.

When he’s not inspiring leaders or building businesses, he is busy coaching and mentoring youth, and is a board member for the National Center for Fathering, an organization that was created to respond to the social and economic impact of fatherlessness in America. Jim has been involved with Little League, and the youth organization, Ambassadors of Compassion. In addition, Jim serves on the Northridge Community Church Board in Scottsdale, Arizona. To help the church raise funds, Jim purchased Saddlecreek Coffee Company that he operates for the church. In addition to donating 100% of the proceeds to the church, his other goal with the coffee shop is to help teach entrepreneurship to the church’s youth. He also supports and works closely with Partners in Action, a 30-year-old Scottsdale, Arizona-based nonprofit organization operating orphanages and other humanitarian projects in 27 countries.

Tell me about your early career.
I started my career in finance: mortgage banking, investments, and insurance. I sold my first company in November 2006.

How did the concept for HealthiestYou come about?
I was introduced to the concept when a start-up, tele-medicine company was raising money in 2007. The more I got involved, the more I realized that the future was bright for tele-medicine, but that their model was not going to change healthcare.

How was the first year in business?
The first year was exciting, optimistic and energizing. What could possibly go wrong? 🙂 It’s after the first year when you’re hit in the face with reality. Businesses take time and lots of pivots to find the right product, pricing, messaging, and market fit.

What was your marketing strategy?
I was heavily influenced by blue ocean strategy. We looked to go where no one else was going. We essentially did the opposite of our competition. They had a low utilization, low priced (commodity) product focused on large employer groups. We built a high utilization model with a price that could sustain that utilization and focused on small- to mid-sized groups. No one could on board and administer small groups efficiently, so they were forced to focus on large blocks of business. We set our sights on the ten million small businesses and how we could make a difference for them through employee retention, reducing health care premiums, absenteeism, etc.

How fast did the company grow during the first few years?
Year 1: $300,000
Year 2: $700,000
Year 3: $1,300,000
Year 4: $3,000,000
Year 5: $10,000,000
Year 6: $20,000,000

How do you define success?
Professionally: When a company’s core values are represented by every employee in every situation, resulting in consistency and profitability.

Personally: The choice to use your time how you want and not how others want you to. For me, it’s about truly living out my priorities of God and family, before chasing power and wealth.

What is the key to success?
Persistence, Passion, People and Pivoting. I believe everyone can be successful if they stay in the game long enough, surround themselves with good people, and are willing to listen to what the market wants and needs, and make those changes, no matter how many there are.

What are the greatest lessons you’ve ever learned?
There are two:

1) EVERYTHING happens for your own good, if you view it as a learning experience and not as a distraction or failure. Every time we had a setback, we realized it was a set up for something bigger. That mindset is critical to surviving as an entrepreneur.

2) Money doesn’t make you happy. The day I saw my bank account with all the zeroes in it, I felt nothing. Although I have a large home and can do/buy whatever I want, there is little to no joy in that. People should never sacrifice time with their loved ones for material wealth.

What are some of your favorite books?
Business: The Four Agreements, all of Patrick Lencioni’s books, Blue Ocean Strategy, Traction, and Three Feet from Gold.

Personal: Shadow Divers, Endurance, Unbroken, and Confidence Game.

Tell me about one of the toughest days you’ve had as an entrepreneur.
1) Many times, I could not make payroll. Having to tell your team that you will be late paying them is gut-wrenching.
2) Being told by investors that promised to send money that they changed their mind.
3) When a large payer made an offer to buy us at a time when I was dead broke. I had to turn it down, although it would’ve been good for me personally/financially. The deal didn’t make sense for my investors or employees. I was devastated, but believed something better was coming in the future. We sold two years later for 10x more.

When faced with adversity, what pushes you to keep moving forward?
1) Belief – You have to KNOW that you will make it. I have a mantra, “The harder the struggle, the bigger the reward.”
2) Family/wife – I believe your spouse must be 100% behind you, at all times.

What advice would you give to young entrepreneurs?
1) It’s all about the story. Figure out your story and then find a compelling way to tell it so everyone can easily understand it.
2) It will take a lot longer than you think and cost 5x more than you think, but you can do it.
3) Everything happens for a reason.
4) Don’t lose sight of your priorities.
5) 99.9% of all your large deals will fall through. Don’t count on any of them.
6) Find the blue ocean and hit a lot of singles. The homers will come in due time.
7) Don’t quit. You’re three feet from gold.