Nick DiNatale of ShipPlug On Five Things You Need To Create A Highly Successful Startup

An Interview With Doug Noll

A founder has to be a “good loser,” because when things don’t go your way, which they will at times, you must have the ability to roll with the punches and stay level. The rest of the company feeds off the founder, especially at the outset.

Startups have such a glamorous reputation. Companies like Facebook, Instagram, Youtube, Uber, and Airbnb once started as scrappy startups with huge dreams and huge obstacles. Yet we of course know that most startups don’t end up as success stories. What does a founder or a founding team need to know to create a highly successful startup? In this series, called “Five Things You Need To Create A Highly Successful Startup” we are talking to experienced and successful founders and business leaders who can share stories from their experiences about what it takes to create a highly successful startup. As a part of this series, we had the pleasure of interviewing Nick DiNatale.

Founder of ShipPlug, a data-driven insights and proprietary software company that saves businesses time and money when it comes to their parcel shipping efforts, Nick DiNatale cut his teeth as a FedEx Sales Representative-turned-Sales Manager, where he managed high-profile accounts totaling hundreds of millions of dollars over a 12-year span. While working there, he identified a pain point among customers that didn’t understand the claims process or their pricing contracts, resulting in financial losses. Enter ShipPlug, which has recovered $1 million in refunds for late shipments and generated a total of $12 million in savings for its customers in just two years. Having seen firsthand companies go out of business due to a lack of understanding regarding their shipping costs, Nick is passionate about bringing a level of transparency and clarity to the space, providing customers fair and appropriate price-saving solutions in the process.

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?

I’m a Pittsburgh native, born and raised, and now reside in Miami, FL. Once I graduated college, I fled Pennsylvania winters. I have always had a passion for helping others and talking about business ideas. I kickstarted my career as an accountant, but quickly realized that wasn’t for me. I switched to my first sales job at FedEx, and quickly fell in love with it. During my time there, I discovered there was a huge need for both small and large businesses to understand their shipping costs and simplify the entire shipping process.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

It was actually on my first day at FedEx as a field sales rep in New Jersey. I was speaking with a potential client who didn’t understand his pricing contract. He talked about consistent billing issues he was having with UPS. I showed him my proposal, which included his current average package cost, and compared it to what it would cost at FedEx: it was 40% cheaper and he would save $1.2 million overall if he went with FedEx. He questioned this at first because it was my first day, but after crunching the numbers he realized how much he could indeed save by switching carriers. It was then I realized that even big companies don’t always have the resources or wherewithal to know whether their carrier is pricing them out or overcharging them, so they may not even be aware they’re eligible to file certain claims or receive refunds on their shipping costs.

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?

My college roommate thought I would be a great fit at FedEx, and he ended up getting me in the door there. He eventually went off on his own and started a similar company to the one I run now, and it was really successful. He knew I was capable of doing the same thing, so he inspired and encouraged me to do so. While I was unsure at first, ultimately his belief in me (along with his advice and guidance), made me believe that I could start my own business. So I did. He was very instrumental in helping me get my company off the ground.

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

How much better our software is than that of our competitors. We can tell our customers the best option they should ship with based on their rates. We provide invaluable data that allows them to make the most informed decisions. We also create simple, easy-to-understand agreements. Additionally, we’re significantly faster and better than our competition. Our competitors can take weeks to get valuable data back to customers, whereas it takes us just minutes. We also pride ourselves on our customer service. Our team has 60+ years combined experience working at FedEx, which has prepared us to help with our customers’ supply chain, actively improving their processes and cutting their costs in the process. And with the rate at which shipping prices change, we can always recommend they ship with a low-cost carrier that meets their service requirements. Lastly, our technology flags any time we see a better rate. The same can’t be said for our competition.

How have you used your success to bring goodness to the world?

My brother is handicapped, so I have experience with, and a passion for, working with people who are handicapped, mentally ill, and/or are homeless. There’s a charity in Miami, where I live, called Camillus House, which provides humanitarian services to people who are veterans, poor and/or homeless in Miami-Dade County. Through our customers and fundraising efforts, we’ve been able to give $30,000 to the organization this year alone. Ultimately, I believe we have a responsibility as individuals and a business to help our respective communities.

Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

First, I’m a really “good loser” in that I can handle rejection and adversity well. We all make mistakes, but it’s how you deal with and learn from them that matters. I don’t spend time beating myself up. Instead, I try to understand what may have led to making a mistake, then I move on. For example, I hired someone I knew and believed in, but the individual wasn’t able to deliver. I had to admit that I made a mistake and, while it wasn’t easy letting the individual go, I knew I had to for the sake of the company. Second, relatability, in terms of being able to work with, and manage, all types of personalities (employees and customers). As a leader of a company, you have to stay open so that employees and customers feel comfortable approaching you. Yet you also have to set boundaries, so employees know what’s expected of them. My team knows I have an open door policy, which I think strengthens camaraderie. Third, I consider myself to be someone who is self-aware. I know what I’m good at, as well as what I could use help with. It’s important to remove ego from the process and surround yourself with people who can positively contribute to your business. Launching a startup has its obstacles, but having faith in yourself and others goes a long way toward overcoming them. I’ve made it a point to play a part in the hiring process, as I believe a company is only as good as the people who work for it.

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?

Like others I’m sure, I’ve been told in the past that as long as I keep my nose down and follow all the “rules and instructions” I’m being given, I’ll get to “where I want to be.” While that may be true for some, I had my “aha” moment early on, and had a pretty good understanding of what I needed to do to get to where I am now as a business owner. But I was also a little naive when I first started out, and wasn’t entirely sure I could go off on my own and launch a business… until I was encouraged by my former college roommate. I think one has to be careful who they’re getting advice from, and what the advice is, because what works for one individual may not work for another.

Can you tell us a story about the hard times that you faced when you first started your journey?

I had to let go of an individual who I cared about a great deal, but who wasn’t able to deliver business-wise. I tried making it work, but the situation became untenable so I had to make a tough decision. It was hard because I cared deeply for this person. But these things happen. There may be times where you hire someone you know for any number of reasons, and sometimes it works out; other times it doesn’t. I had another employee who got sick and was in the hospital, but I didn’t know about it until weeks later. I had no idea where the individual was and couldn’t reach them, so I was obviously concerned. Thankfully, the employee ended up being OK, but if you’re a caring boss you’re inevitably going to face hard times because your employees will face challenges outside of the office that can impact the company in various ways.

Where did you get the drive to continue even though things were so hard? What strategies or techniques did you use to help overcome those challenges?

I got my drive from my mom, who was a single mom and raised me and my brothers. She had no help and very few breaks. She did it all, and didn’t “have time” for a bad day. Even if she was sick, she had to gather the strength to go to work then take care of our family. Seeing her do all of this, with an impressively good attitude, inspired and motivated me to push through challenging times. It taught me to be consistent and disciplined on a daily basis, especially with things that are non-negotiable. As far as strategies or techniques, I believe it’s so important to work out and read to stay physically and mentally fit. Staying busy and making checklists helps me stay focused, yet conversely I’ve realized it’s also important to take time to decompress and do nothing. I like planning vacations and spending time with family and friends. I expect the same from my employees, especially those who have kids. Work-life balance is paramount.

The journey of an entrepreneur is never easy and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder”?

Ideally, you don’t want to get too caught up in the highs or lows. The reality is you’re going to win and lose business, so it’s important to cultivate an ability to roll with the ups and downs. I do this by forming plans and doing what I can to stick to them. This helps me stay balanced and focused via routines and checklists. Now, plans can change, so you have to be adaptable, but having a starting point allows you to put processes in place you can stick to and follow. Also, don’t forget to acknowledge day-to-day successes. These small reminders and an overall positive attitude, can sustain you through challenges and setbacks.

Let’s imagine that a young founder comes to you and asks for your advice about whether venture capital or bootstrapping is best for them? What would you advise them? Can you kindly share a few things a founder should look at to determine if fundraising or bootstrapping is the right choice?

I think it depends on the entrepreneur, as there are pros and cons for both. If you bootstrap it, there’s a lot of pressure due to the constant money crunch. You have to pay people first, be able to survive on your own, while also spending money on the business. So you have to make sure you don’t run out of money. That being said, you have the ultimate decision-making freedom, as no one is micromanaging your books, questioning your hires, etc. When you take money from others, there’s less of a money crunch, but you have to constantly check in with investors and run most of your decisions by them. If you can handle certain pressures, I think bootstrapping is the way to go.

Here is the main question of our interview. Many startups are not successful, and some are very successful. From your experience or perspective, what are the main factors that distinguish successful startups from unsuccessful ones? What are your “Five Things You Need To Create A Highly Successful Startup”?

1 . A founder has to be a “good loser,” because when things don’t go your way, which they will at times, you must have the ability to roll with the punches and stay level. The rest of the company feeds off the founder, especially at the outset.

2 . Have a high level of emotional intelligence. You need to know what you do really well for starters, and continue to assess this moving forward so you can hire people who can help with certain things you might not be great at. I only want to hire “A-level players,” because you need a team filled with people who are at, or close to, the top of their game.

3 . You always want to make an effort to coach, train and/or mentor people. Even if you have a team filled with “A-level players,” it’s important that everyone has the opportunity to give and receive active feedback. Not only does this offer direction and information about what’s expected of them, but it helps avoid problems or issues which can arise. Most people want the opportunity to be heard, and if everyone is allowed to speak their truth, I believe this often leads to improvement in performance. Ultimately, the culture you establish as a founder can make or break your business.

4 . You have to have a plan and vision of where you’re going and how you’re going to get there. Again, this plan can change over time, but having a roadmap at the start sets the tone for a startup moving forward.

5. Luck. Along the way you’re going to have to have some of it. You can create your own luck too, of course, but timing is everything. For example, Netflix went from people having to buy a DVD player to DVD players essentially being included in TVs. For Facebook, having apps be available on phones made their platform accessible to everyone, which wasn’t the case when they first launched. Most companies have had a crazy stroke of luck that led them to where they are today. In our case, we had an amazing FedEx salesman who got fired for an absurd reason, so we hired him, which changed the trajectory of our company. If he doesn’t get fired, it’s highly unlikely we’d ever get him.

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?

I’ve seen a bunch of founders who couldn’t take feedback from inside their company, or externally. If your team is afraid to give you feedback, it can lead to stagnation or complacency. Encourage feedback and be able to take it well, even if you don’t agree with it. You never know where a good idea can come from, so it’s important to encourage an open dialogue.

Startup founders often work extremely long hours and it’s easy to burn the candle at both ends. What would you recommend to founders about how to best take care of their physical and mental wellness when starting a company?

Working out and reading (about an hour a day). Make it a priority, so your mind and body stay sharp, which can lead to new ideas. It also helps with stress and pressure. It’s almost impossible to keep up the grind without it. I think most founders who become successful, at some point realize the importance of this. Our company pays employees for gym memberships if they go at least four days per week.

If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

A movement that fights and fixes corruption, especially within politics and venture capitalism. It’s rampant throughout the world, and I think it speaks to a deeper problem that mankind faces in the 21st century. Part of it starts with raising our youth to be morally and ethically sound, but as a society, especially in the US, we often equate a sense of self-worth with obtaining a certain level of money, power, and/or fame. By raising and encouraging people to be compassionate and empathetic, and give more than they take, this, combined with creating and enforcing laws to protect those who are most vulnerable, are steps towards reducing the corruption that exists.

We are blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

DJ Khaled. As part of our culture at ShipPlug, when someone closes a deal and brings aboard a new client, we share DJ Khaled memes. We love his confidence and the uplifting, humorous, and inspiring ways in which he connects with his audience.

How can our readers further follow your work online?

You can learn more about ShipPlug and even request a demo by visiting www.ShipPlug.com.

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