David Pike of New York Trolley Company: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

by Charles Purdom
David Pike of New York Trolley Company: 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 David Pike.

David Pike is the founder and CEO of New York Trolley Company. He is also the author of the book, “The New Startup,” and has been featured in Forbes, The New York Times, New York Post, Good Morning America, CBS Inside Edition, Huffington Post, Business Insider, and VentureBeat, among other outlets. David is a mentor and advisor for startups at Founder Institute as well as a guest lecturer at his alma mater, the University of Michigan, where he graduated with a BSE in Industrial Engineering.

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?

David Pike: I grew up in Chicago and attended the University of Michigan where I earned a degree in Industrial and Operations Engineering. I worked for a few years doing consulting while moving back and forth between Chicago and NYC. On the side, I started several businesses with varying degrees of success. Some of these companies include an apparel company, several ecommerce websites, a mobile app with subscription access to entertainment venues in NYC, and a charter bus company. In 2018, I wrote a book to provide aspiring entrepreneurs with a step-by-step approach to starting a business as well as help them avoid some of the mistakes I made.

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

David Pike: In 2010, I moved to NYC to be a consultant for Accenture. After 6 months of going out and exploring the city, I realized I never once saw a trolley. Back in Chicago, trolleys are everywhere. People book them for weddings and birthday parties. There are 5 trolley companies in Chicago and the largest one has over 40 trolleys. I thought to myself – if this works in Chicago, it has to work in NYC.

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

David Pike: From a young age, I loved starting businesses. When I was 9, I would host garage sales. When I was 12, I started a summer camp for kids in the neighborhood. In high school, I launched a used book sales business. I always knew I wanted to create something and be my own boss.

David Pike of New York Trolley Company: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

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?

David Pike: My uncle is an entrepreneur who started his own landscaping company when he was 20. One summer in high school, I cut lawns for him. They were long days doing hard manual labor. I remember my whole body aching at the end of each day when I would get home. It was really at that point when I decided I was going to work for myself one day.

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

David Pike: I would say our customer service is what makes my company stand out. The charter bus industry is a lot like the cable TV provider industry in that customer service is horrible.  Most charter bus companies could care less about customer service. They don’t respond to emails or calls, their vehicles are late and their drivers are rude. They don’t put the customer first. We pride ourselves on going above and beyond for our customers. For example, at one wedding last summer, a downpour of rain began during the ceremony.  Without asking, our driver drove to a local store and bought umbrellas for everyone in the bridal party so no one would get soaked or ruin their hair.  Another time, we provided transportation for a birthday party.  When the party concluded at 12am, the group exited and headed home.  However, one of the women onboard had left her wallet and keys on the trolley.  Our driver called the party organizer to try tracking down this woman.  He eventually tracked her down around 2am and dropped off her items so she could get into her place that night!

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?

David Pike: Perseverance, being organized, and hard work.  

Things are going to go wrong in your company – wrong hiring decisions, slow sales, etc. As you entrepreneur, you need to stay positive and stay motivated. Perseverance is the key. For me, finding commercial auto liability insurance was a nightmare. I spent 6 months trying to find insurance for my company. Being a startup and operating in a tough and expensive market (NYC), not many insurance carriers (or any for that matter) wanted to cover me. However, through networking, I was able to find a broker in Connecticut who worked with a carrier that would cover me. By staying positive and networking with friends and colleagues, I was able to find a solution. 

Being organized is essential for an entrepreneur. As you launch your venture, you will have many responsibilities to juggle. Stay on top of everything. Google calendar and the iPhone notes app are critical tools to use. 


Hard work goes without saying.  Prepare to work longer and harder than if you worked for someone else. That being said, this work will feel more rewarding. You are building something on your own and you will have pride in 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?

David Pike: When I was thinking about starting one of my first ventures, I received advice saying I should start it with a friend. I followed this advice and brought on a friend as a 50/50 partner. Fast forward 12 months, I was doing 80% of the work but only seeing 50% of the profits.  We ultimately sold the company but our relationship deteriorated because of the business.  If you decide to go into business with a friend, make sure you create an agreement upfront that stipulates responsibilities and earn out percentages.

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?

David Pike: Actually care about your employees. Develop friendships with them. Ask them about their lives. Create an open and transparent culture where employees can come to you if they feel overwhelmed. Celebrate their contributions and welcome their ideas and feedback.

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

David Pike: Deliver what you promise to customers. For example in the charter bus industry, you can read thousands of reviews of companies providing old buses that are dirty and break down. You hear stories of drivers showing up an hour late. Be responsible for your company and that includes your vehicles and your drivers. Make customer service a priority.

Can you help articulate why doing that is essential today?

David Pike: This is essential today because everyone reads reviews. The companies that survive are going to be the ones that treat their customers the best. Today there are more options than ever before and more transparency than ever before. The companies who provide the best customer service are going to be the ultimate winners.

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?

David Pike: The biggest mistake I’ve seen is not doing enough planning before launching a business. I believe that most businesses are doomed to fail before they are ever launched. You need to research the market you are entering as well as your competition. Research your potential customers. Are they going to pay for your product or service? Entrepreneurs need to test their idea before they launch. How can they do that? Set up a website with photos of your product and a shopping cart. See if you can convert sales. If you are providing a service, call potential customers and see if they will pay for your service. Set up a website and see how many leads you get. Create a financial forecast. What are your expenses the next 6-12 months? How much revenue do you expect over that time? Be conservative with your revenue estimate.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

David Pike: Being an entrepreneur is dealing with the unexpected. You are going to have highs and lows. You could experience euphoria if you land a huge deal or get press from a major outlet. On the flip side, you could lose a major customer or have a vendor issue affecting your supply chain. You need to ride the highs and the lows, but most importantly, don’t get too down on yourself when the lows hit. Remember that you are capable to solve these problems and that’s what makes you an entrepreneur. Someone with a “regular job” might have highs and lows as well but it’s completely different because ultimately, the responsibility falls on the shoulders of the CEO. As an entrepreneur, you are the responsible one and the company is a reflection of you.

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.

David Pike: A few years ago, we landed a big booking with Ralph Lauren. They wanted all 3 of our trolleys to shuttle VIP guests around between NYC Fashion Week shows. Our drivers arrived early and were ready to great guests as they boarded. Well, one of the guests turned out to be Martha Stewart and she chatted with our driver for 10 minutes! Overall, we received stellar reviews and great press from the booking.

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.

David Pike: In 2012, I was parking all my trolleys in Hoboken, NJ. It was a random weekend in October and a big storm was predicted over the next few days. Thinking nothing of it, I continued with business as usual. Well, that storm turned out to be Hurricane Sandy. It rained down on the NJ/NY area for several days and there were tidal storm surges in the area. I came to check the trolleys after the storm settled down and they were parked in 5 feet of standing water. It took 4 days for the water in the parking lot to drain. I lost all of my trolleys to the storm. I thought my business was finished. However, I persevered and was able to replace the vehicles within a few months and keep the future bookings I had.

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

David Pike: I brainstormed all my potential options and wrote down what each scenario would look like. Do I fix the waterlogged trolleys? Do I buy new trolleys? Do I cancel future bookings? Do I partner with another company in the interim until I have operating vehicles again?  Ultimately, I repaired two of the trolleys and cancelled bookings in the short-term until they were fixed. Customers were very understanding as many of them had been affected by Sandy as well. By staying organized, being creative, and not being too hard on myself, my company was able to bounce back.

Ok super. Here is the main question of our interview. 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.

David Pike:

1) Have a positive outlook

As an entrepreneur, you are guaranteed to hit rough patches. Stay positive. When my trolleys were totaled in Hurricane Sandy, I was devastated. However, I quickly stopped feeling sorry for myself and started to brainstorm solutions to get me out of this mess.


2) Persevere

Things are going to go wrong. You may lose your largest customer. Your best employee might leave you. Don’t give up. Stay calm. Be creative and believe in yourself. You started a business. You can get through this.


3) Surround yourself with positive people in your life

 Whether it’s your family or friends, make sure you have a good group of people to celebrate the wins but more importantly, support you during the lows.


4) Always have multiple balls in the air

This can really help you ride the lows. I’ve found it’s helpful to have several big initiatives in the oven or likewise have multiple sales proposals out there. If any one of them fails, it won’t be such a big deal since you have other opportunities. 


5) Be grateful

Look at how far you’ve come. This is all because of you. You created a company. That is a major accomplishment. We are all lucky to be alive. We are lucky to live in a country where we can create a business.


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?

David Pike: Resilience is being able to bounce back. You are going to face setbacks and challenges as an entrepreneur. By keeping a positive attitude, you can weather these storms. Resilient people are optimistic and self-confident. Resilient people can stay calm when disaster strikes. They are problem solvers who thing outside of the box.

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

David Pike: In 2013, my girlfriend (now wife) and I were on vacation on an island off the coast of Panama. We rented a small motorboat for the day so we could explore some of the surrounding uninhabited archipelago. We motored from island to island exploring beaches and swimming. I drove the boat out a bit to the west so we could see an unobstructed view of the sunset before heading in. I turned off the engine and the sun sank below the horizon. I went to start up the engine and it wouldn’t start. I kept trying it and trying until it was flooded. We were a few miles from our island, it was getting dark, and we had no radio, flares, or cell phone service. We were drifting out farther into the open Pacific. As we counted down the hours, I had to stay calm and be positive. We huddled in the open boat overnight as the temperature dropped and the waves were building.  Around 4am, I managed to jump the engine with a screwdriver to get it started.  I motored us back to shore at 5am.  This experience left me extremely grateful, but also reminded me of the power of creativity and the importance of keeping a clear and positive mind.

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

David Pike: Keeping a positive attitude is essential. When I encounter a difficult situation, I remind myself of a few of my favorite mantras. Be grateful. You are lucky to live where you do and have your own company. This difficult situation will pass. Relax and spend time thinking about potential solutions. Reach out to colleagues, mentors, and friends for advice.

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.

David Pike: Your enthusiasm and zest are contagious. They go a long way in helping to fix a less-than-ideal situation. I recall one wedding where a small ceremony was to take place in Central Park. It was pouring rain outside and our trolley drove the bridal party and guests to the park. Everyone was reluctant to get off the trolley, and the bride was in tears. I suggested to the officiant and groom about hosting the ceremony onboard the trolley. I had my driver run out quickly to buy some decorations and a few bottles of champagne. The officiant held the ceremony on the trolley and afterwards, we drove them to their post-ceremony restaurant. The bride emailed me a few weeks later, saying that we saved the day.

Ok. Super. We are nearly done. 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?

David Pike: “Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma — which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.” – Steve Jobs


When I first started my trolley company, people rolled their eyes and thought it was a joke. Not many of my friends believed it could be successful. But that didn’t stop me. I ignored them and continued to build the company each year. I went with my gut and in the end, it worked out.

How can our readers further follow you online?

David Pike: Readers can send me a message at NY Trolley

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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