How I Managed the Disappointment of Not Getting on ‘Shark Tank’

Disappointment is a part of life. This may be a biased comment, but disappointment feels more acute for people like entrepreneurs, who risk everything to make their dreams a reality.

Entrepreneurs quit their jobs, sacrifice relationships with friends and family, cash out their 401(k)s and run head-first into the unknown — that place in the universe filled with possibilities, tremendous joy and fulfillment. But also with lots of disappointment.

I’d like to share how I overcame the disappointment of not making it to the final round of auditions to get my company, WeMontage, on the incredibly popular TV show Shark Tank.

Why I Wanted to Get on Shark Tank

I recently listened to a great audio book by Ben Horowitz called, The Hard Thing About Hard Things. I had one really great takeaway from the book:

When things get hard in your business and you’re not sure if there is anything you can do to make a difference, you ALWAYS have a move.

Let me repeat that. You ALWAYS have a move.

Things have been extremely challenging at WeMontage since we ran out of funding back in the spring. I have a great product with hundreds of happy customers, but the biggest issue for the business is lack of consistent national exposure.

Shark Tank has 20 million viewers. So, while it was a complete long-shot, getting on the show was my move. And doing so obviously would have addressed what I’ve identified as the major issue for the business.

I made it to the next-to-last round of auditions, but did not get the call to go to LA to pitch to the Sharks. Cause for disappointment? Perhaps…

How I Handled the Disappointment of Not Getting on Shark Tank

I initially thought I didn’t make it to the second round of auditions because people in line around me at the audition got their call back and I hadn’t; I was really upset about this because the producer said my pitch was great. I eventually did get the call a few days later and was super-pumped about it.

After I prepared my nine-minute pitch video for the producers and submitted my lengthy application, a funny thing occurred. I made a conscious decision that it didn’t matter what happened next, as I knew I had put forth my absolute best effort. I think that choice was inspired by something Ariana Huffington said in an interview about her new book, Thrive.

Ariana, a super-Type A personality, said she realized she can only control 10 percent of what happens in life, so she does her 10 percent at 100 percent of her ability and trusts the Universe to handle the other 90 percent. So, maybe that’s what I did, too. Or maybe I just released the whole thing because I’ve learned that my greatest disappointments in life have been when I expected a certain outcome and it didn’t come to pass. Or maybe it was some subconscious effort to protect my mental health. I actually think it was a combination of all three of these things.

Surprisingly though, I wasn’t disappointed to learn I didn’t make it to Shark Tank.

Disappointment of Others Who Support You

My wife has been incredibly supportive throughout this entrepreneurial journey. When I didn’t hear back about making it to LA, she was still optimistic it was going to happen. Once the trailers for the new season of Shark Tank started airing, the reality set in that I wasn’t going to be on the show and I could tell she was disappointed. And for the first time in the last three years, she began to question the feasibility of me accomplishing my dream of making WeMontage a household name.

She asked me, “Do you think WeMontage is going to happen.” My answer surprised even me. I didn’t hesitate in my response, “Yes, I do. I don’t know exactly how at this point, but I’m OK with that. I have a few tangible things coming up soon, that should make a huge difference.”

I was grateful she accepted that answer without hesitation. I was even more impressed that I still had the resilience in me to respond so affirmatively and so quickly in that way.

Suggestions for Managing Disappointment

I looked around the Internet to see what others recommend for handling disappointment. I found a few practical, platitude-free suggestions in an article over at Here are six recommendations in the article for how to effectively cope with disappointment.

1. Manage emotion
2. Don’t take it personally
3. Review expectations
4. Take a big picture perspective
5. Try again — or try another tack

I think I’ve used all of these tips during the last three years of chasing my dream. The thing I think I’m best at on this list though is number “6”, which is being resilient.

Resilience Matters

In my experience, the one thing that has consistently kept me moving forward, other than the support of my amazing wife, loving family and friends, is resilience.

There have been plenty of times I’ve wanted to quit, but I haven’t.

I still might quit…

But not today.

How have you dealt with disappointment as it relates to being an entrepreneur? Are there things you can share that might help others? Please do so in the comments.

James Oliver, Jr. is a husband to an amazing wife, Ayana, and co-founder of the world’s cutest twins, Thaddeus and Zoe. James is a tech entrepreneur who successfully raised private investment capital for his startup, WeMontage, the world’s only website that lets you turn your photos into large collages on removable wallpaper. James graduated Phi Beta Kappa from Morehouse Collage and has an MBA from the Kenan-Flagler Business School at UNC-Chapel Hill. Follow @jamesoliverjr on twitter and via treplifedad on Facebook and G+. You can connect with James via his lifestyle blog for parent

A Conversation with Danielle Hester, Digital Editor of ArtInFact Magazine

Q: Where are you from originally?

Q: What is AIF? What does it represent?
AIF is a content and community platform for people doing creative things in New York City outside of the traditional 9-to-5 work structure. We cover a range of entrepreneurs and startups, independent artists like filmmakers, fashion designers and musicians, and local community projects.

But we also cover mainstream topics from an underground perspective. While the Internet is buzzing about the new Trey Songz album, we’re more interested in the person who shot the photography. What’s his story? And more than likely it’s a freelance photographer who would appreciate the press coverage.

Our goal is to bring the behind-the-scenes creative process to the forefront. We’re fascinated with telling the stories of people you wouldn’t necessarily hear about in mainstream media. AIF represents the millennial who has taken action to pursue their creative endeavors. The brand represents us, its creators, who started a brand because we wanted to produce quality content about topics we care about. This concept is how we came up with the name ArtInFact magazine. We believe there’s always an art element to the facts you know about, and some facts to the artistic work you see.

Q: What inspired this idea for AIF?
I run AIF with three amazing editors who I met during our time at Columbia J-School. The initial idea to start an independent magazine came from our managing editor Semmi W. She approached me, Ashley and Angel with the idea, and the overall concept of AIF was conceived collectively.

We were all recent graduates working as freelance writers, copy editors and fact checkers, but were somewhat unhappy with the kinds of stories we were asked to do over and over again. We were battling with having to produce overly saturated, SEO-driven content.

We would get together and find ourselves obsessively talking about the types of stories we wanted to write and the influencers we loved to follow on social media who we wanted to know more about. So, we decided to create our own magazine and tell the stories we wanted to tell and that we felt were interesting and important.

We wanted to give people the facts behind the art (creative person) they loved. At first, AIF was just a passion project. We had no business plan, no real direction for the site. We ran the site very independently. Each editor would publish whatever we wanted, whenever we felt like it, kind of like a blog. But it was very important to us early on not to look like a blog site. We wanted the site and our work to reflect the technical training we had received at Columbia.

But that required so much. We were putting in a lot of time interviewing and writing stories while working full-time jobs. After a while, the process started to feel pointless without any real editorial or business direction.

Around this time, Semmi W. and I got invited to attend a business development workshop in the Hamptons that was hosted by Dell. While there, we listened to entrepreneurs talk about their successes and failures. One of their biggest concerns was that there was a disconnect between entrepreneurs and their access to quality media coverage; that it was hard for them to get media coverage about their startups and creative projects.

That’s when we made the pivot to focus on the projects and creative processes of entrepreneurs, indie artists and influencers living in NYC. It became our goal to feature these unknown people and package the content in the same way you would see it in New York Magazine or Vanity Fair.


Q: What do you believe makes AIF different from other online publications?
AIF has such a unique focus in which we serve to fill a need for a specific group of people who work hard to make their passion projects come to life, but feel ignored by mainstream media outlets. There’s a loyalty that comes with our content because we, too, are in the same boat as the people we cover.

So, when we write an in-depth profile about a startup and promote it on our social media pages, they appreciate it, and in return will help to promote AIF, too. We’re not a news-breaking website. That’s not our purpose. What makes AIF different, in a sense, is that we are building long-lasting relationships with our subjects. We want to help them build their press coverage. It’s all about using our skill sets to help a fellow creative reach their goal, and they’ll use their resources to help ours.


Q: Choose three words to describe your professional journey and why?
1. Progressive: I’m not the same writer or editor I was five years ago, or three years ago, or even a year ago. I am always trying to progress and build my skill sets. I am always looking for new things to learn about my craft. I’m so far away from my initial dream of being a magazine editor. Now, I’m on the digital production side, and I love it!

2. Goal-driven: I always set goals. I tend to focus more on short-term goals because I am the type of person who is always open to trying new things, and long-term goals feel like they box me into one idea. Nevertheless, I’ve always had some sort of goal, whether it was to grow a certain skill set or start a passion project with three friends. I think this has definitely helped me in my professional development because I am able to identify what I want to gain from a project or job position.

3. Patience: I came out of undergrad in 2008 when the economy was in really bad shape. The publishing industry still struggles with not having enough resources to hire full-time staffers with reasonable pay and health coverage. I’ve had to be very patient with my career. I’ve had to take many contract jobs and freelance positions, even after I got my master’s in journalism. But I’ve met and worked with some amazing writers and editors along the way who gave me opportunities I am so blessed to have had.



7 Things to Do Before Becoming An Entrepreneur

So, you want to be an entrepreneur? Well, like most things in life, it’s not for everybody. There’s a quote that says, “Entrepreneurship is living a few years of your life the way most people won’t, so you can spend the rest of your life living the way most people can’t,” and for the most part that’s true.

Since entrepreneurship is not for the weak or the weary,  we give you seven things to consider before you decide to make the plunge.

Be Passionate About Your Product

For some, it may be easy to work a 9 to 5 job that you aren’t passionate about, but if you’re an entrepreneur launching a product or service, how do you expect consumers or investors to be excited about your product if you aren’t?

As your own boss, you become the chief salesperson and your enthusiasm has to make others believe in you. Another reason you must believe in your product or service is because entrepreneurship has many peaks and valleys and you’re going to need determination to get you through unpredictable times.

Cleanse Your Social Media Profiles

Prospective employees are often told to clean up their social media profiles, but entrepreneurs must do the same especially when they are taking meetings with potential investors.

Sometimes it’s not enough to dress the part, you also have to take into account that people will check your Linked In profile, Facebook, Twitter and Instagram pages. You have to be mindful of the photos you post since they could be misinterpreted.

Have a 12-Month Plan

If you’re not organized or don’t like to plan, then entrepreneurship may not be for you.

Be prepared to write your business plan more than once and it will need to be looked over by professionals and trusted colleagues. Your 12-month plan should include your personal and business budget.

In the calendar section of your business plan, you need to include vacation, medical appointments and important events.

Know Your Finances

Finances are a large part of being an entrepreneur and you’ll need to take care of any outstanding debt before pursuing your goals.

Downsizing and creating a monthly budget are effective ways to pay off debt. As an entrepreneur you may not get your first paycheck for months, so you will need to have 12 months of savings to pay your bills.

Know That You Can’t Stop At Just One Product

An entrepreneur is essentially an innovator, and as an innovator, you have to keep, well, innovating.

This basically means that after you launch a product or service, you have to keep up the momentum and stay ahead of the innovation curve. To consistently develop products means that you’ll have to spend money. Companies rarely, if ever, survive with just one product.

Be Good at Making Decisions

If you’re indecisive or can’t make decisions without the input of others, you might want to rethink becoming an entrepreneur.

Entrepreneurs are responsible for the successes and failures of their businesses. They have to make decisions about working from home or leasing office space, hiring employees, targeting high-end clients or selling to the masses, advertising, borrowing money, using savings and more.

The decisions become more complex after employees are hired and the company starts succeeding.

Maintain Balance 

Entrepreneurs don’t take days off and working nonstop often means neglecting your life outside of work, which can cause burnout and a subsequent decline in business.

While maintaining a personal life with family, friends and hobbies, you must also know how to limit distractions from entrepreneurial pursuits.

Balance is all about maintaining good health and mental welfare, while still working toward your goals.