Nestor Villalobos of ‘The Iron Man Entrepreneur’: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

by Christina Gvaliant
Nestor Villalobos of ‘The Iron Man Entrepreneur’: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur  we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Nestor Villalobose.

Nestor Villalobos (aka The Ironman Entrepreneur) is a nationally recognized business leader, mentor, and serial entrepreneur who aims to engage and inspire other business professionals by helping them attain the skills and knowledge necessary to lead full, extraordinary lives.

With BS and MBA degrees from Bentley University, Nestor Villalobose started his career in product management launching hundreds of consumer products for Dell and CompUSA. After escaping the corporate world (with his soul mostly intact), Nestor entered the world of entrepreneurship after launching his own startup. In 2016, Nestor acquired a controlling interest in Sharp Marketing, a struggling 30-year-old promotional products distributor. Under his leadership, the company has now turned around to become one of South Florida’s fastest-growing promo distributors.

Dubbed ‘The Ironman Entrepreneur’ because of his affinity for athletic challenges and his successful completion of the prestigious Ironman Triathlon, Nestor Villalobose believes that many of the same multi-disciplinary training principles employed by elite athletes can — and should — be adopted by all entrepreneurs.

Nestor’s enthusiasm for business and athletics is only surpassed by his passion for mentoring and inspiring the next generation of entrepreneurs. As an Adjunct Professor of Business at Florida International University, Nestor leverages his real-world experiences to inspire hundreds of students in courses including International Business Negotiation, Small Business Management, and Entrepreneurship. Nestor’s latest endeavor is Resale Hero, an innovative B2B startup launching in 2021 with the mission of helping distributors and manufacturers that struggle with the complexities of managing resale certificates.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Nestor VillaloboseWhen my business partner and I originally purchased Sharp Marketing (a promotional products distributor), the entire operation was run using physical files and folders. The previous owner was ‘old school’ and even liked to her print emails. One of the first major changes we made to the business was to move everything digital. This meant adopting an online order management system and leveraging cloud-based accounting and file management software.

The one aspect of our business that we had a hard time finding a solution for was resale certificates. For the uninitiated, resale certificates are documents that our clients supply us when they intend to resell a product to the end consumer. When they provide us with these documents, they become responsible for collecting the sales tax and remitting it to the state government. Therefore, when we sell to them, we do not have to charge them taxes (since they will be the ones responsible for collecting and remitting).

The challenge is that these certificates expire annually. Furthermore, one is required for each state they do business in. As such, every client could potentially have dozens of resale certificates. As you can imagine, keeping these documents current was becoming a huge challenge as we expanded our customer base. The certificates we had on file would lapse and we would forget to request the new ones. If we were ever audited, would be liable for paying all taxes owed plus up to a 100% penalty.

There were a few solutions that existed at the time, but they were very expensive. Others required the replacement of our entire accounting system. The ‘Aha Moment’ came when I asked my business partner if there were no “affordable solutions for small business?”. His response was “No. But there should be”. That same day, we registered the URL “” and the rest is history.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

Nestor VillaloboseAnyone can be an entrepreneur. The difference is that some people have personality traits that allow them to achieve success faster than others. I am of the firm belief that opportunity is directly tied to risk. Entrepreneurs that have a higher risk tolerance level are more willing to put themselves in a position of first-mover advantage. Case in point — Elon Musk with Tesla and electric vehicles, Jack Dorsey with Twitter’s social media platform, and Steve Jobs with the Apple iPhone.

As a young child, and later as an adult, my favorite activities included triathlons, water & snow skiing, skydiving, scuba diving, motorcycle riding, and piloting airplanes. I believed that if there isn’t any risk involved, the payoff for mastery isn’t as sweet. I love finding opportunities where I can learn something new. This why I believe you see so many successful business leaders become ‘serial’ entrepreneurs. Once mastery is achieved, they often look for the next big thing.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

Nestor VillaloboseMy father was a big inspiration for me. Ever since I was a kid, I remember him waking up early, working all day then still coming home with the energy to raise two (hyperactive) children. I was six or seven when he took me to visit one of his factories. It was a large contract manufacturer that assembled apparel items for some of the big brands including Dockers, Banana Republic, and Gap. After I was given a factory tour and learned how jeans were made from start to finish, I was fascinated. I begged my father to allow me to work at the factory that summer which he did. When other kids my age were at summer camps I was in the factory learning about operations and human resources. I knew that one day I wanted to own my own factory.

What do you think makes your company stand out? Can you share a story?

Nestor VillaloboseResale Hero stands out because our product/market fit is very specific. For the most part, our competitors have focused on building very large, complex systems that include a ton of other features that may be important to large businesses but would be superfluous for much smaller ones. By cutting out all these features and solely focusing on one aspect of the business (resale certificates), we have carved out a very interesting niche.

Another feature that makes us stand apart is that no other competitors were offering ‘freemium’ access to their platforms nor would they allow anyone to sign up and use their software immediately. Instead, they required the customers to be onboarded by one of their customer service representatives. Knowing this, we took the opposite approach. Free and immediate access to our platform with no human interaction required. Once a client reaches a pre-determined threshold of customers, we then start charging for the service and scale the pricing based on client count. This makes it a zero-risk proposition in terms of capital and time investment to the customer.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Nestor Villalobose

Crave Learning — I like to remind my students that education does not end with a college degree. As an entrepreneur, it is important to keep abreast of industry trends and changes. One of the easiest ways to do so is by reading. Audible is an amazing audiobook service owned by Amazon that allows me to ‘find time’ when driving to read the latest business books. By doing so, I am constantly being fresh ideas to my businesses and keeping abreast of the latest industry developments which help prevent competitors from getting ahead of me.

Unafraid of Taking Risks — Nothing great was ever achieved without risk. At Sharp Marketing my team members take this to heart. Every week we have ‘postmortem’ sessions where the entire company spends a few minutes going over any issues or failures from the previous week. The end goal is to first understand what the mistakes were and then adopt new policies or procedures that allow us to move forward as an organization. This fosters a collaborative environment where team members aren’t afraid to make mistakes.

Be Ironman Committed — The Ironman Triathlon is one of the most grueling competitive events out there. It features a 2.4-mile swim, a 112-mile bike ride, and a full 26.2-mile marathon. To complete one takes an almost god-like amount of discipline in three distinct fields — nutrition, physical exercise, and mental toughness. In my case, I used to train for at least 20 to 30 hours a week on top of my full-time job. Many of the people I trained with were successful business entrepreneurs. I quickly came to realize that they applied the same level of training intensity for triathlons as they did for their own businesses.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

Nestor VillaloboseI had always believed in the expression, “if at first, you don’t succeed, try and try again”. I took this a bit too far in my 30’s when I was running a startup that was teetering on the edge. I ended up plowing my life savings as well as all credit I had available to me to ‘save’ the company. This ultimately resulted in my declaring personal bankruptcy. In hindsight, I should have known when to cut my losses and move on to the next project. These days, I go by the mantra expressed in Kenny Roger’s song The Gambler:

You’ve got to know when to hold ‘em

Know when to fold ‘em

Know when to walk away

And know when to run

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

Nestor VillaloboseIn their excellent book “Built to Last”, authors Jim Collins and Jerry Porras coined the term BHAG, or Big Hairy Audacious Goal. By establishing one of these, organizations can create a clear purpose and vision that aligns everyone in the organization. Once the BHAG is established, the next step is to set up

bite-sized achievable milestones that bring them closer to the BHAG. When one of these milestones is hit, it is important to celebrate these small wins as a company. Case in point, when I was at TigerDirect, their BHAG was $1 Billion in sales a year. Every time they hit a new weekly milestone ($1 Million in sales, $5 Million, $10 Million) they would print out “I was there” t-shirts and give them to everyone in the organization and host a party.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Nestor VillaloboseTo build trust, credibility, and authority in your industry there are two things you need to do. The first is to give back to the community. The second is to build an audience. I have always enjoyed teaching, so becoming an adjunct professor at Florida International University was my method of achieving both. If that’s not an option, entrepreneurs should consider volunteering at a local business-networking organization. This could be the regional chamber of commerce, Mastermind group, Rotary Club, or any other relevant networking group. By volunteering, you are putting yourself in a position of authority which helps to establish yourself as a leader among your peers.

Can you help articulate why doing that is essential today?

Nestor VillaloboseWith today’s global economy, it is becoming harder and harder for business leaders to stand out from the crowd. As such, they need to focus on growing their social currency. Many folks use social media to achieve followers, likes or comments. However, smart business leaders are using these tools to educate, inspire and motivate others. Since people trust and prefer to interact with people and not brands, it gives the business leader a leg up on the competition.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Nestor VillaloboseMany business owners feel that they need to start a business in an area that they are passionate about. This is a mistake that is highlighted in great detail in the book “The E-Myth: Why Most Small Businesses Don’t Work and What to Do About It” written by Michael E Gerber. Essentially, individuals who understand the technical work of a business dupe themselves into thinking they can successfully run the business that actually does the technical work.

As an example, if someone is very good at baking cakes, before they start their own bakery, they should first understand the fundamentals of running a business. These include understanding financial statements, business operations, marketing, sales, and human resources. Many businesses have failed due to the owners not having the technical skills necessary to handle these aspects of the organization. This is why knowing one’s limitations and finding business partners that fill those gaps is an important consideration.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

Nestor VillaloboseFunny enough, the day I made my first million dollars caught me by total surprise. For weeks, I had been working on a major deal with a new client. Getting the deal done required a significant amount of logistical prep work and negotiating. After one especially grueling phone conversation, we finally got the green light from the client. I was still exhausted from the negotiation process to realize what that ultimately meant for me financially. It wasn’t until later that evening that the funds hit my business account that I remember calmly informing my fiancé (now wife) that we had just made a million dollars. It truly didn’t even register with me until she asked me to repeat what I had just said. When I did so, I vividly remember a huge weight being lifted off my shoulders. Whoever said money can’t buy you happiness lied.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

Nestor VillaloboseOne of my previous startups failed in a very spectacular fashion. A number of years ago, I had raised over $1.3 million in investor capital for a food-related business. In just 3 short years, the entire business imploded. I ended up declaring personal bankruptcy since my own finances were so intertwined with that of the startup. It was my biggest failure by far and many, many people found out about it. I thought there was no coming back from that and even considered going back to the corporate world with my tail between my legs.

Based on your experience can you tell us what you did to bounce back?

Nestor VillaloboseLuckily, the truth is that my idea of failure was much harsher than what it really was. I found incredible support from my family, friends, and even the very investors who had lost money in the endeavor. Once I realized that they were rooting for me to succeed and (and not just the business), I was able to dig myself out of the emotional grave I had put myself in. It’s through their support that I had the opportunity to find and fund my next endeavor which turned out to be very profitable for all those involved.

What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

Nestor Villalobose

Perspective — I like to remind my entrepreneurship students of perspective. For the most part, unless you are in the medical field, the decisions you make as an entrepreneur will have little to no effect on whether people live or die. It’s important to keep this in mind as there will be failures. No matter how bad those failures are, no one is really going to kick the bucket.

A Supportive Network — Whether it’s family members, friends or mentors, seek out individuals that can support you on your entrepreneurial journey. When times get tough, these are the folks that can help you ride through the lows. Individuals that bring you down have no place in your social circles.

Optimism — Being an optimist helps business leaders succeed as they are able to focus their positive energy towards creative solutions that might otherwise be ignored by someone solely focused on the consequences.

Outlet — It’s very important for business leaders to engage in productive activities that are unrelated to a venture. These can include sports, continuing education, music, or even gardening. Physical exercise is especially important since it has the benefit of improving circulation, boosting brain power, and releasing endorphins. All of these hobbies have one thing in common — they all allow individuals to meet and achieve goals. Doing so provides a positive mental outlook for achieving other goals in the business world.

Vision — Ultimately, entrepreneurs need to visualize what success looks like. By doing so, they are able to establish clear goals and milestones. These are important since success doesn’t happen overnight. By having clearly defined markers on the path to success, we can look back and see how far we have come.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Nestor VillaloboseI define resilience as the act of dealing with an unpleasant situation and not letting it bring you down. The most important character trait for resilient people is mindfulness There are many non-productive ways to distract oneself from unpleasant situations. These can include drugs (both legal and illegal), overeating, TV, and video games. They are non-productive since they don’t actually help to solve the problem. By being mindful or being in the moment without judgment or distraction, one can heal quicker and move on with a new perspective.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

Nestor VillaloboseAs a kid, I was a late bloomer and used to get picked on constantly by the other boys. One memorable beating I received left me with a nasty black eye. Most parents would try to get involved either by contacting the school or reaching out to the other parents. Mine was a little different and suggested that I join a gym. After going every day for a year, I gained a solid understanding of weight training as well as mixed martial arts. Once the other boys realized that I was not going to be an easy target, they decided to leave me alone. I really appreciate that my parents gave me the opportunity to solve my own problems instead of getting involved.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

Nestor VillaloboseThere is one piece of advice that I typically give my undergraduate students on the very first class of the semester that leaves them in shock. “I want you to fail”. After I say this, I pause for effect. Most students look at me as if I had said a four-letter word.

Most college students (and, I dare to say, most people) have never been told to fail. Much less from a college professor that is potentially standing between them and their coveted “A” in class. For all their lives, they have been brainwashed to believe that success only happens with the absence of failure. I do not believe this is the case. Success happens because of failure.

The most important inventions were made because there were a few entrepreneurs that were not willing to stop after they ‘failed’. Thomas Edison tested 6,000 different filaments before he identified a carbonized cotton thread that ultimately produced the light bulb. Edison believed so much in his invention that he was willing to fail…..Six. Thousand. Times. The lesson? Be willing to accept failure knowing that success is just on the other side.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

Nestor VillaloboseI have a strong belief in the idea of positive and negative energy and its compounding network effect in a business. If a leader gives off a negative vibe while at the office, it will eventually get picked up and multiplied by employees. They, in turn, will then broadcast this negative energy to both vendors and customers alike. This also works both ways. If a client brings negative energy to a business, it can maneuver its way all the way up to the top of the corporate ladder.

Not too long ago, I had a problematic customer come back to place a reorder. From the minute he called into our office, he was rude to our receptionist and then again to the account manager that had been assigned to him. Since this wasn’t my first time hearing about this client, I knew it was a repeating pattern. Ultimately I decided to ‘fire’ him. I did so by explaining that we were no longer focused on his industry (which was mostly true) and felt he would be better served by one of my competitors.

I was willing to give up the client as I knew that his negative attitude would have a magnifying effect throughout or organization. By doing so, my employees actually applauded my efforts and expressed how important it was that I took their ‘side’ instead of believing in the ‘customer is always right’ mantra. This ultimately improved the bond between myself and my team members.

What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

Nestor VillaloboseI often hear the phrase “it is what it is” which always riles me up. Most people use this as an excuse to give up and accept what fate has dealt them. For me, it has the exact opposite effect. Whenever I hear it, I have the deepest desire to jump into action, changing my fate, or re-evaluate my perspective.

The last time I heard this phrase was with a close friend. This person had been working at a major public company for years and had been passed up for promotion for the third time. I knew how dedicated she was to her career and profession and how much it meant for her to advance. Instead of just accepting her off-handed comment, I offered to help her brush up her LinkedIn profile and seek out a headhunter. Within a few weeks, she was offered a higher-level position at a competing firm for 30% more pay.

This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!

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