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Nicklaus Morton and Evan Mendelsohn of Tipsy Elves: “Be optimistic”

Work Hard! It may sound simple, but nothing happens without a ton of hard work. I’ve known so many extremely smart people who come up with wonderful ideas only see them fail. To be successful in business or any other endeavor you need to work hard — bottom line. The bigger you get the harder you will […]

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Work Hard! It may sound simple, but nothing happens without a ton of hard work. I’ve known so many extremely smart people who come up with wonderful ideas only see them fail. To be successful in business or any other endeavor you need to work hard — bottom line. The bigger you get the harder you will need to work. It’s easy to read stories in the media about overnight success stories but those are few and far between. The vast majority take many long nights and huge team efforts to find success.


As a part of my series about the ‘5 Important Business Lessons I Learned While Being On The Shark Tank’ I had the pleasure of interviewing Nicklaus Morton and Evan Mendelsohn.

Tipsy Elves was started by friends Evan Mendelsohn and Nicklaus Morton in 2011. The former lawyer and dentist created the company after realizing they didn’t have enough festive wear for holiday parties they attended. While on Shark Tank, their business sense and passion for their product impressed Robert Herjavec, who invested 100,000 dollars and owns a 10% stake in the company.


Thank you so much for doing this with us! Our readers would love to “get to know you” a bit more. Can you tell us a bit of the backstory about how you grew up?

We both grew up in medium sized towns (Redding, CA and Sparks, NV). We both spent a lot of time playing sports like hockey, skiing, tennis, soccer, baseball and spent a lot of time outdoors with our families. Eventually, we went to UC San Diego where we met and became friends and roommates. Our similar upbringings made us quick friends and eventually business partners!

Can you share with us the story of the “aha moment” that gave you the idea to start your company?

During college we both always enjoyed dressing up for themed parties and events. We recognized that when we would wear something a little more outrageous it made the people around us a lot more open to new conversations. It also put us in a frame of mind that we were going to have fun, laugh a lot and meet a lot of new people. We loved how social dressing up made us feel. After college Evan became a corporate lawyer and I [Nick] became an endodontist and as we started our careers, we quickly realized that the “day to day” wasn’t for us. We had always dreamed of starting a fun clothing company but weren’t sure where to start. Around that time, we started to see that “Ugly Christmas Parties” were gaining popularity but when we went to attend, we couldn’t find anything other than used sweaters at thrift shops. We felt we could do better and have a lot more fun with it, so we decided to launch our apparel business around the holidays. When we also realized that no company was targeting popular google search terms like Ugly Christmas Sweater, Tacky Christmas sweater we realized that we had a free path to massive marketing reach. Tipsy Elves was born!

Can you share the most interesting story that happened to you since you began leading your company?

One of the most interesting things that happened to us was we appeared on Shark Tank! Back in 2013 Shark Tank was one of the most popular shows on TV — and it still is! Back then any time you started to see a little business success everyone would tell you, “You have to go on shark tank!” So, we felt like “Hey, we have to go on Shark Tank!” We’d actually filled out the application and funny enough right at that time a producer from the show called us. They’d worn one of our sweaters the year before and wrote down our company’s name to contact us the following year because they had such an amazingly fun night when they wore our gear. We were invited to apply and since we already had the application locked and loaded, we sent it right in. Going on Shark Tank was an amazing opportunity. We were able to partner with Robert Herjavec who’s been an amazing partner, advisor and mentor. It really added some fuel to the fire and pushed us forward.

Can you share a story about the most humorous mistake you made when you were first starting? Can you tell us what lesson or take away you learned from that?

When we first started, we had this humping reindeer design on a sweater that we’d drawn ourselves, but we didn’t make it clear to our manufacturers that needed to use our exact design. We thought that was clear. When the first 1,000 sweaters arrived, we realized they used a humping reindeer design that was actually copyrighted and not our own design. We had to trash all 1,000 sweaters! Who would have thought that humping reindeer could cause so many issues?

Are you working on any exciting new projects now? How do you think that will help people?

We have a ton of new things in the works. Tipsy Elves exists to make the world a more fun place to be for everyone, so we are trying to “Tipsyfy” many different categories. We’re expanding our ski collection and relaunching our golf collection and even creating one of a kind scrubs to bring some fun and joy to places like doctors offices and hospitals. Tipsy Elves is all about self-expression and inclusivity and we want to help people to have fun and show the world who they are no matter how they have fun, who they love, what ethnicity they are, etc. 2020 has been a tough year and if we can help to inject some positivity to the world we are on the right path.

Ok, thank you for all that. Let’s now move to the main part of our interview. Many of us have no idea about the backend process of how to apply and get accepted to be on the Shark Tank. Can you tell us the story about how you applied and got accepted. What “hoops” did you have to go through to get there? How did it feel to be accepted?

Like I mentioned above we got pretty lucky because one of the producers actually wore our gear! That being said we still had to apply. First, it was a paper application, then we had to make a video. We decided to create a pretty silly video of Evan and I dancing wearing our sweaters. We figured we needed to be entertaining first and a good business second since it was TV after all. It worked! We were invited to the show to film. At that point, you have one more hurdle to clear which is you need to do your initial pitch to the producers. That was the most nerve-wracking part because if you blew that you may never get into the tank. Once we found out we would be filming a couple of days later we breathed a sigh of relief and the actual filming, while intimidating, actually felt less scary that try out.

I’m sure the actual presentation was pretty nerve wracking. What did you do to calm and steel yourself to do such a great job on the show?

Actually, filming is really scary! You walk through the 2 sets of double doors like you see on TV with a camera guy walking backward and the music playing. Once the second set of double doors opens you immediately see all 5 sharks right in front of you. Then you stand there waiting to start the pitch for 45 seconds while the cameramen make sure they have all the cameras set up correctly. This 45 seconds feels like 10 minutes having a staring contest with the sharks. Then a voice from above (the producer) yells, “Begin!” and you start your pitch — talk about scary! That being said, Evan and I have always been optimists and it’s a core value at Tipsy Elves. We told ourselves that the worst-case scenario is we totally bomb but 8 million more people learn who Tipsy Elves is. That’s a pretty great worst-case scenario and knowing that helped us power through. Thankfully the outcome was even better.

So what was the outcome of your Shark Tank pitch. Were you pleased with the outcome?

We ended up making a deal with Robert Herjavec for 100,000 dollars for 10% of the company. We were and still are extremely happy with the deal. Robert’s an awesome human being and a very shrewd businessman. He was instrumental in giving us the confidence to expand beyond Christmas apparel and on a personal level very encouraging to me to leave my career as an endodontist to focus on Tipsy Elves full time. He’s also a great advocate and promoter of Tipsy Elves and is always available for advice.

What are your “5 Important Business Lessons I Learned While Being On The Shark Tank”? (Please share a story or example for each.)

  1. Be entertaining. When you are on TV or giving a presentation or talk it’s important to entertain or at least be interesting to the audience. It doesn’t matter if you are saying something incredibly groundbreaking and insightful if you are boring, no one is listening to you anyways!
  2. Be Respectful. When we went on Shark Tank, we made sure to be polite and respectful and we try and treat others the way we want to be treated. The old Golden Rule. That doesn’t mean be a pushover or not fight for what you need or believe in, but it means that you are honest, fair, and polite. After being on Shark Tank and meeting many of the other entrepreneurs you see a wide range of approaches and personalities. I think a big part of our success both on Shark Tank and beyond is we are easy to work with. If people enjoy being around you, they will want to work with you and that is usually a good thing.
  3. Be optimistic. Starting and running a business is one of the most difficult things you can do. There are going to be a ton of roadblocks to overcome. You can’t ignore them but even more importantly you can’t dwell on them. You have to focus on the opportunities, visualize the positive outcome you are going for and then go and get it. Evan and I are realistic optimists and it has allowed us to stay calm and power through tough times.
  4. Be Detail Oriented. It’s important to step back and see the big picture but the small details do matter. When it comes to design the type of font you choose or the color scheme or the copy can completely change the feel of the final product. When it comes to contracts and pricing every detail matters and can put you on a path to financial success or disaster. Avoid micromanaging but do cultivate a team of people who are uncomfortable settling for second best.
  5. Work Hard! It may sound simple, but nothing happens without a ton of hard work. I’ve known so many extremely smart people who come up with wonderful ideas only see them fail. To be successful in business or any other endeavor you need to work hard — bottom line. The bigger you get the harder you will need to work. It’s easy to read stories in the media about overnight success stories but those are few and far between. The vast majority take many long nights and huge team efforts to find success.

What advice would you give to other leaders to help their team to thrive and avoid burnout?

I think having Evan as a business partner has been huge in avoiding burn out. There are many people who warn against starting a business with a friend, but I couldn’t disagree more. You just need to make sure you start your business with the “right” friend. You need to have different strengths and weaknesses and ideally, you think about things differently too. However, you must also be able to communicate effectively especially during stressful times. If you can do those things, it’s great for the business but also keeps the day to day fun. If you don’t have a business partner, then I’d recommend connecting with other entrepreneurs in your area. Having someone to complain to or discuss new ideas can be very powerful. It can get really lonely as a business owner especially if you are a solo business owner so get off the island and connect! The last thing I would say is that Evan and I both had “traditional” careers that we didn’t particularly care for prior to starting Tipsy Elves and that perspective combined with coming to work each day with a wonderful and talented group of people makes us feel very lucky and blessed.

You are a person of great influence. If you could inspire 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. 🙂

Our hope is we can continuously inject positivity, fun and optimism into the world. This has been a really tough year for just about everyone. We recognize how tough this year has been and it’s not over yet, but we also recognize the power of positive thought and how important it is to find areas to be thankful for. We feel it is extremely important, maybe now more than ever, to find reasons to still celebrate, to express ourselves, and to have fun. We want to be an example of a company and a group of people who understand the hardships in the world and still chooses to focus on the positive and our hope is by doing that we can make the world a more fun place to be.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I can give you two: “Focus on the opportunities, not the obstacles” and “Make the hard choices today, so you are lucky tomorrow” Tipsy Elves has gone through a lot of ups and downs. From the highs of appearing on Shark Tank to exponential growth to the lows of huge fulfillment issues, financial troubles, and the shutdown of most in-person gatherings and more. We’ve found that throughout the past 10 years staying disciplined and “doing the right thing” both financially and ethically has opened up unexpected opportunities down the road. When times are tough it’s easy to cut corners but staying positive and sticking to the right path has always proven to be the path to the best long-term outcome and that has allowed us to weather the current storm of 2020 in an extremely positive way.

We are very blessed that some of the biggest 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 with, and why? He or she might just see this if we tag them 🙂

Nicklaus Morton: I think I’d like to have breakfast with my grandpa. He was an entrepreneur in his own right and really believed in Tipsy Elves very early on way before we really showed any signs of success. We actually tried to do a friends and family round after our first year in business and not a single person wanted to invest except for him. Unfortunately, he passed away before Tipsy Elves really took off and I think it would be really fun to talk to him today to share all that is going on and get his insights and feedback on where we are. It would be a really fun conversation and I’m sure he’d have some sage advice!

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