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Tips From The Top: One On One With Evan Mendelsohn

I spoke to Evan Mendelsohn, co-founder of Tipsy Elves, about his journey and best advice

Adam: Thanks again for taking the time to share your story and your advice. First things first, though, I am sure readers would love to learn more about you. What is something about you that would surprise people?

Evan: A lot of people don’t know that I was a lawyer before starting Tipsy Elves. I used to practice corporate law at a large law firm.  

Adam: How was your experience on Shark Tank? Can you walk readers through the process, from how you made onto the show to your appearance to the investment and how the show has impacted your business? What advice do you have for those interested in getting on Shark Tank?

Evan: Shark Tank has been an incredible experience for us. We were fortunate enough to have one of the show’s producers reach out to us because she was personally familiar with our brand and products. We still had to go through the application process, but this definitely gave us an edge in the process. Once we got accepted, we had about a month to prepare for the show; we spent most of this time watching old episodes of the show and getting a better feel for the kinds of questions we might be asked. We wanted to make sure we felt prepared and knowledgeable on the show.  

We made a deal with Robert Herjavec for 10% of our company. It’s been an amazing partnership, and Robert has been able to coach us through a lot of key strategic decisions. He’s been a consistent mentor and a friend since we first made our deal with him back in 2013. 

The show has been a great platform for us. Even after spending millions of dollars on online advertisement, we still see that Shark Tank is one of the top ways that customers have heard of Tipsy Elves. It’s such a popular show and it exposes your story and products to millions of interested viewers. We’re so grateful that we have been able to be part of the Shark Tank family.  

For those aspiring to be on Shark Tank, I’d advise them to make sure they have a unique angle and are doing something different. The show gets so many applicants now (and is now on it’s 10th Season) that they are really looking for unique businesses that will interest their viewers. And if you are able to make it to the next step and get a filming, make sure you know your numbers really well. The Sharks are quick to discredit entrepreneurs who don’t know their financials inside and out.  

Adam: What experiences, failures, setbacks or challenges have been most instrumental to your growth? What are your best lessons learned?

Evan: It’s hard to pinpoint specific challenges, but we’ve learned that every business, including ours, is going to have unexpected surprises. It could be a bad fulfillment company, it could be an unstable website, it could be a bad marketing decision, or not ordering enough units of a top seller.  

I think the lesson here is that all businesses are going to have surprises. Sometimes you don’t know what these will be until they happen, but we’ve learned it’s possible to anticipate a lot of these issues in advance with proper planning. To get ahead of these, we have several “check in” meetings throughout the year where we make sure we are anticipating our biggest sources of risk and taking measures to prevent these things from happening. We literally ask ourselves, “what are the top things that could go wrong this year?” and we plan accordingly so that these things don’t happen. 

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

Evan: We try to lead by inspiring our team with our vision of the company. We truly believe that there is tremendous opportunity ahead with Tipsy Elves, so we do our best to share our enthusiasm and vision with our team so they are always aware of the things that are most important to me and Nick Morton (our other co-founder). This leads to a healthy culture where the entire team is able to work towards a shared vision.  

Beyond this, we like to create a transparent environment where we share both the good and the bad. We lead with a pretty open book so that our employees are always aware of what’s going on at Tipsy Elves. We feel that the more informed our team is about the inner workings of the company, the more we will all be aligned.  

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?

Evan: The three tips that come to mind are:

1) Test before you go all in – I think it’s important to test your business model before you refinance your house, quit your job, and put you and your family at risk by “betting it all” on an idea.  For me, I tested the Tipsy Elves concept while I was still working as a full time lawyer. It meant I had to work some very long days spending the full day at the law firm and working on Tipsy Elves at night. But it allowed me to test the concept and make sure it was successful before I decided to quit my job and go “full time” on the business.

2) Pick your co-founder wisely – I have a great relationship with my co-founder Nick Morton. We are best friends and we have a really healthy communication style. Do we disagree? Absolutely. But we align on the important things and we have a similar appetite for risk, a similar enthusiasm and optimism for the business, and a similar vision and goal. And we know how to work through disagreements in a healthy manner. It’s not always easy to know these things before choosing a co-founder, but I think the more you can assess these things the better off you will be.

3) Align yourself with strong mentors – One of our best mentors has been Robert Herjavec from Shark Tank. He has helped us navigate some really important strategic decisions. One of the best benefits of a mentor is to help you avoid costly mistakes. We’ve been in business for almost 10 years and have made countless mistakes. Luckily, we’ve been able to avoid the big ones by having solid mentorship. At the end of the day, when you start a business you are figuring things out as you go. There is no formal training for how to navigate entrepreneurship. Luckily, a good mentor can provide the training that can help you avoid the big mistakes.  

Adam: What are your three best tips specific to entrepreneurs in the ecommerce space?

Evan: The three tips that come to mind are:

1) Control your marketing spend – The advertising platforms like Google and Facebook make it so easy to blow through money without really understanding your ROAS, which ads are working and which aren’t. Have your metrics dialed in well before you start increasing your spend on these channels.

2) Find an ecommerce platform that is reliable – We went through years of unstable websites that would crash during peak volumes or couldn’t handle our Shark Tank airings. You don’t realize how stressful it is to have a site crash during peak sales periods until you experience it first hand.  

3) Deliver a high quality product – We see so many companies try to skimp on quality just to get a few extra dollars of margin. We’ve seen the benefits of delivering high quality products that wow our customers. The payoff has been an increase in brand loyalty, and our customers come back and buy from us over and over again. 

Adam: What is the single best piece of advice you have ever received?

Evan: I think the best advice I’ve heard is to “trust your gut.”  This really impacted me when deciding to quit my law job to pursue Tipsy Elves on a full time basis.  After spending eight years in college and grad school and getting the law job that most law students dream of having, it was easy to question my doubts about my law career.  I wasn’t passionate about it and the idea of spending my life drafting and negotiating legal contracts was daunting. My gut knew that law wasn’t for me, but I’d still question my gut and tell myself things like, “everyone feels this way about their job,” “just suck it up and stick with it,” or “you’re just feeling this way because this is your first job.”  And of course, my parents were also nervous about my decision to quit my job.  At the end of the day, I trusted my gut and quit my job and it was one of the best decisions I ever made. If I ignored my gut and let myself rationalize my decision to stay in law, I might still be working as a lawyer today and I can’t imagine what my life would look like today if I hadn’t started Tipsy Elves and pursued it full time.  

Adam: What is one thing everyone should be doing to pay it forward?

Evan: I always try to be pretty open when giving business advice to friends and people in my circle. We’ve had a lot of help and mentorship along the way, and I think one of the best ways for us to pay it forward is to give advice and help people who are in entrepreneurial endeavors. I’ve been in the position where one piece of advice has been tremendously helpful, so I try to remember this when helping others. 

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