Jason Chan of Rakuten Super Logistics: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

by Charles Purdom
Jason Chan of Rakuten Super Logistics: 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 Jason Chan.

Jason Chan is Rakuten Super Logistics’s Vice President of Sales, Marketing and Client Success.  In this role, Chan drives RSL’s growth and culture as it continues to steal market share. Prior to Rakuten Super Logistics, Chan ran CenturyLink’s West Coast marketing and nurtured his entrepreneurial spirit, owning several businesses including car washes, an energy drink company, and a real estate investment group. He has a Bachelor of Arts degree in Economics from the University of Nevada, Las Vegas Honors College.


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?

Jason Chan: I’ve been in sales and marketing for over 20 years ranging from owning my own companies to working in the Fortune 500. My secret sauce is to accurately assess an opportunity, craft a strategy to maximize the success of said opportunity, and then execute that strategy with unrelenting passion. This formula has worked for me time and time again.

As they say, every journey begins with the first step. My first step can be traced to literally flipping candy in school which then become computers, electronics, and eventually any item or service I could make money on

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

Jason Chan: It boils down to filling a need. Ecommerce has grown exponentially over the past two decades and is showing no signs of slowing down. I meet with entrepreneurs daily who are experts of their product as well as at the sales and marketing of that product but lack the skillset and infrastructure to successfully fulfill their orders. My team and I help them solve their real pain points surrounding fulfillment and logistics. I was taught early on that people will pay for pain relief before vitamins, so the future of my business is bright.

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

Jason Chan: Between the binary decision of whether I was born with it or not, I would say I was born with it. However, I think everyone is born with it, but the environment you grow up in, the people you see, and the opportunities that are presented make some people end up more entrepreneurial than others. My family was a large influence because I come from a family of entrepreneurs. From an early age, I luckily had an insider’s view of the hard work, rejection, risk, and passion it took to succeed as an entrepreneur. Later, as I started my own ventures, I had a great network of friends and family who offered support, advice, a soft shoulder, as well as a kick in the pants when I needed it.

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?

Jason Chan: My dad is an entrepreneur through and through and he has invited me to business meetings, negotiations, as well as contract reviews with him since I was 18. By accompanying him, I learned practical skills like how to read a room, how to present, as well as warning signs or concerns that could make a deal go south.

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

Jason Chan: Rakuten Super Logistics stands out for three main reasons: our network, our operational excellence, and our US-based Client Success team. We are a top tier provider with locations across the country. All of this creates an inherent structural competitive advantage that prevents newcomers from copying as it takes time and hard work to build. In a world of chatbots and outsourced customer service, we pride ourselves on the fact that we have humans you can speak to who will address your concerns promptly.

Jason Chan

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?

Jason Chan:

Creativity. If you want extraordinary results, you have to take extraordinary actions which means you aren’t doing what your competition is doing. This often takes creativity to be able to come up with solutions your competition couldn’t even fathom.

Can-do attitude. Everyone can tell you why something won’t work, but it takes a can-do attitude to show everyone why it will work. As you succeed, everyone will see it and the momentum behind your ideas will create more successes, but it all starts with your belief that you can make it happen.

Fun. I like to have fun in everything I do, otherwise, it will just feel like work. This also implies being surrounded by other people who enjoy fun which inevitably builds an environment where people are comfortable with each other , work well together, and will succeed together.

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?

Jason Chan: Have a diversified portfolio and don’t buy Bitcoin. Joking aside, I remind myself that most advice is worth exactly what you paid for it $0.00. It can be valuable to hear other people’s input, but at the end of the day, the decision is yours and all of the advice in the world won’t change that. Make a decision, stick with it, and if you’re wrong, adjust as quickly as possible and learn for next time.

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?

Jason Chan: Take a break. It could be as simple as a walk around the block or a chat with an old friend, but we each need to know how we can ground ourselves and get recharged. I’ve set a culture in my own departments that if it seems like we have hit a wall and aren’t moving forward, we may go get a coffee or ice cream just to change things up so we can come back to the table with fresh heads. Not every problem needs a trip to Bali to solve, but Bali helps too!

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

Jason Chan: Be consistent and create a track record for success. A lot of people want to make a splash by trying to hit home runs and inevitably miss. In my book, I’d rather see a single, then a double, and so on to see progressive movement towards putting points on the board than being a one hit wonder who may never score or can’t replicate the past success.

Can you help articulate why doing that is essential today?

Jason Chan: Inevitably, big problems take big solutions which by necessity requires a lot of smart, thoughtful people. If a leader cannot build those traits above, they will turn into a one-person show as they will fail to attract a team who will help them collectively succeed.

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?

Jason Chan: Know what you’re good at and stick with it which also means to outsource or partner on things that you are not good at. All too often, people are a penny-wise, but a pound-foolish trying to conserve money at the cost of growth.

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”?

Jason Chan: Your money, your reputation, your business, and your employees as well as your own livelihood are constantly on the line. You could do things perfectly day in and day out for years growing your business and suddenly a pandemic hits. You suddenly need to scramble to figure out how to protect your employees while still growing the business despite the fact that your vendors may be struggling. At the end of the day, your client is still looking for you to deliver and you must find a way or you’ll be out of business. That’s way harder than clocking in and out.

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.

Jason Chan: The most public was when I was running sales for my company All In Energy Drink. As part of our marketing, we inked a deal to be the official beverage sponsor of the World Series of Poker and eventually sponsored Nascar. These moments were high notes, but they were even more noteworthy as they gave us the visibility and reach to meet new customers and really grow our base. Steps like these allowed us to go public and grow the business to a $50M market cap.

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.

Jason Chan: I once owned a karaoke bar. You need to know 2 more things, I don’t drink, nor do I sing karaoke. You can guess where I’m going, but I was closing down one night at 3 AM knowing that I had to be back at 7 AM to double check deliveries with the team and knew I couldn’t keep going like this. I luckily was able to sell to my #1 customer and moved on with my life

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

Jason Chan: Ignore the sunken cost and make the best decision for any given moment. You can’t get back time and money so focus on moving forward and cut dead weight when you need to. 

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.

Jason Chan: Cherish the highs. Take pictures, film videos, invite people to share in the highs because there will be accompanying lows and you’ll need those memories to remind you why you will persevere and get through it.

Envision the highs. I’m a believer in visualization and affirmations. If you can psych yourself to be “in the zone,” you’re in the zone and nothing can take you out of it.

Know that everyone experiences highs and lows. The difference is how we react to them. Be the one who overcomes the waves instead of the one drowned by them.

If you’re in a low, change things up. Again, doing the same thing will
give you the same results. If you want a different result, do something

Rely on your team. You may be the founder, but everyone can be a part of the success you create. Don’t look at everything as a problem you need to solve. Ask for help, counsel, and a helping hand when you need it.

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?

Jason Chan: Survival no matter the circumstances. People who are resilient are flexible, strong-willed, disciplined, and can even be stubborn.  When everyone is saying you can’t do something or shouldn’t do something, you’ve got to a find a way to push forward if you believe in your vision.

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

Jason Chan: I mentioned my dad earlier. I knew whether we were doing well or not as a kid based on what we ate. When he did well, we’d be eating steaks and lobsters and when business wasn’t so hot, it felt more like rice and beans. Yet, no matter what we ate, he kept working every day to ensure the family had food on the table and that we had more good days than bad. This is oversimplified, but the gist is that I saw early on that winners don’t just fold their cards so to speak. You have to keep showing up, trying your best, and the success will come.

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

Jason Chan: Always. I’d like to think I was born with it. Even if I wasn’t, I’ve never seen negative people thrive, so why would I want that attitude regardless of whether it’s an easy or difficult situation.

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.

Jason Chan: One of my mom’s favorite sayings was to lend your smile in case someone doesn’t have one. Smiles and a positive attitude are contagious. People can’t help but mirror positivity when you display it to them.

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?

Jason Chan: “We find comfort among those who agree with us – growth among those who don’t.” – Frank A. Clark

I’ve seen every kind of attitude, style, etc in the boardroom negotiating. When we agree, deals can be done fast and easily. When we don’t, we really get to know each other to find common ground to get a deal done. If you can’t find a way forward with people who disagree with you, you’re guaranteed to fail. This ability to work with literally anyone allows us to achieve success after success.

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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