Interview with Entrepreneur Evan Mendelsohn, Co-Founder of Tipsy Elves


On Season 9 of the Real Housewives of Orange County, the ladies gathered with their significant others for an ugly sweater Christmas party.  Those ugly sweaters that you’ve often received as a gift are now considered fashionable during the holidays. They’re great conversation starters and the more outrageous you look, the better.

If you’re interested in the Ugly Christmas sweater, then you may enjoy my interview with Evan Mendelsohn, who is the co-founder of Tipsy Elves.  Evan was kind enough to share his thoughts on his experience as an entrepreneur, discussing the launch of Tipsy Elves, which is a destination for ugly Christmas sweaters and tacky holiday clothing. And, if you’re a Shark Tank fan, then you may have seen the episode with Evan and his business partner and co-founder, Nick Morton, when they go in front of the Sharks. Of course, after you read this interview, you may want to run out and get your ugly Christmas sweater or better yet, buy one for someone special in your life. It’s not too late!

1. How did you and your co-founder, Nick Morton, come up with the idea for Tipsy Elves?

We attended the same college together and found it impossible to find ugly Christmas sweaters for parties we attended.  We ended up having to buy vintage women’s sweaters from the thrift store.  Seeing a need for ugly Christmas sweaters, I used my background in internet marketing to confirm there was also an online demand for Christmas sweaters and that’s when Tipsy Elves was started.

2. When you first launched, how were you using PR and marketing to promote your website?

I was familiar with search engine optimization (SEO) and social media.  Both were essential to help get Tipsy Elves off the ground.  Search engine optimization helped us rank for big search terms like “ugly Christmas sweaters” while social media helped our sweaters go viral and drive engagement and brand awareness.

3. When you wanted to take your business to the next level, you appeared on Shark Tank. Tell us about your experience in front of the Sharks?

Shark Tank was awesome.  It plays out much like what you see on TV, except a 1 hour session is edited down to just 6 or 7 minutes.  It’s pretty scary at first, but once you get into it, you forget you are on camera and it just feels more like an open discussion about your business with a room full of smart and successful business people.  We were exceptionally prepared when we went into “The Tank” and I think this helped us get a deal with Robert Herjavec.  We made sure we knew our numbers and we also waited until our business had of a track record before appearing on the show, which I think helped get the interest of the Sharks.

4. What is the most drastic change you’ve made after receiving an investment from Shark Robert Herjavec?

Using Robert’s mentoring and investment, we decided to expand the product offerings sold by Tipsy Elves.  Not only can you buy Christmas sweaters on Tipsy Elves, but you can now also buy jumpsuits, college sweaters, t-shirts, and other fun and unique apparel items.  These new offerings have been really successful and have allowed us to have more year-around sales.

5. What are the best and worst parts about being an entrepreneur?

I think the best thing about being an entrepreneur is being your own boss and owning your work life – it is true freedom.  I used to work as an attorney at a large firm.  The hours were long, the dress code was strict, and as a service provider, I was aways at the mercy of senior attorneys and clients who could ruin my weekend at the snap of their fingers by giving me unexpected work and fire-drill deadlines.  By contrast with Tipsy Elves, all successes, failures, and stresses are a result of my actions and are self-imposed.  It’s a very liberating feeling to have that level of ownership over your work-life.

The worst thing about being an entrepreneur, at least for me, is finding balance.  It’s very easy to get obsessed with your business, especially if owning and growing a business has been a lifelong dream of yours.  It’s easy to lose touch with friends, fall behind on workout regimens, etc.  You really have to be disciplined and allocate time to things outside of the business or it will eat all of your time and focus.

6. How much do you rely on social media to promote Tipsy Elves?

Social media helped to give us our start and has always been a main driver of exposure and sales for us.  Our products are unique and fun and cater well to social media since they are so visual.  We get a lot of shares and engagement which helps build our brand and drive sales.

7. What advice would you give to an entrepreneur who wants to pursue his / her dreams?

I’d say that you really have to want it.  Being an entrepreneur is not easy and it takes a ton of hard work, long hours and calculated risk.  I’m convinced that no one has a successful business and makes a lot of money without working extremely hard.  If you want it bad enough and if starting your own business is important enough to you, then you will naturally gravitate towards entrepreneurship and be successful at it.

8. What have you learned through your journey and building the Tipsy Elves business?

I’ve learned that growing a business takes hard work but is really rewarding.  It’s hard to imagine what life would be like without having Tipsy Elves (and being back at the law firm).  Starting and growing Tipsy Elves has been my most rewarding and life-changing experience to date.