Mentor Interview: Shaun Nestor

Updated: Sep 30


Shaun Nestor, Upnotch mentor, is the founder of his own marketing consulting company, Shaun Nestor Brands. He supports smart leaders and entrepreneurs who feel lost, overwhelmed, or frustrated by all the challenges of building marketing campaigns at the same time as running a business.


What is your superpower and why?


I like taking complex problems and breaking them into simple steps to follow.


Have you ever had a mentor?


I have had a mentor in the past, yes. It was very beneficial!


Tell me a little bit about your mentors - who they are or what topics do you like to cover with them?


Currently, I don't have any mentors. When I have had them in the past, one thing I like to talk about was how to scale my business. I have found that when I have a mentor, that's usually when I'm kind of struggling with the scaling portion.


Tell us about a time when a mentor has helped you accomplish a specific goal.


I had a mentor, very, very early in my career. He actually challenged me and said that your web design business will never be anything more than a corner flower shop. At the time, I took that as an offence, and I didn't like it. In the end, it actually challenged me to rethink how I was approaching it and I ended up restructuring it entirely.


How about a time when a mentor pushed you further than you thought was possible or accelerated your career?


I had a mentor a couple of years ago that I was looking at a government project that I thought was well outside of my comfort zone. This mentor challenged me that he believed in me, that he believed that I could do it, and to stretch myself and to reach further. I ended up pitching it and getting the project. And I have him to thank for that.


Any advice your mentor has given you that you want to share?


The one that really stands out as shareable advice, was when a mentor gave me advice that I never wanted to hear. He basically told me that my company would never amount to anything. At the time, I was very offended. But in the end, he spoke the truth. I think a mentor's job is not to sugarcoat the answer, and give the mentee what they want to hear, but it's to deliver some hard truth sometimes.


What would you tell your mentor if they were listening to you right now?


I would tell them that I did it. I don't know if it is in spite of them, or because of them. But I did it.


What makes a great mentee?


A great mentee is made of someone who is willing to listen and apply themselves, but also be open to new paths. So just because your mentor says something, it doesn't mean that is the way. It is a way and a mentee should be open to take it under consideration.


Why do you mentor?


I mentor because, over my career, I've had some very impactful mentors myself. I've reached the point in my career that I can give back and it fuels me and re-energizes me to be able to do the same for others, either earlier in their career, or just looking to overcome an obstacle in their existing career.


What does success mean to you?


Success to me is solving problems. Whether that's in business or personal. A combination of all of that success is looking at the problem and seeing a way out of it, and then moving through.


When did you know you achieved career success?


I knew I achieved career success when I was financially stable. There was a point early in my career, that I literally had $3 in my bank account. When it got to the point that I didn't have to worry about payday, I felt like I had been successful.


What's the secret behind your success?


The secret behind my success is, humbly I would say, that it is to put myself in the position of my clients. Not just to treat them how I want to be treated and work with honor, integrity and respect, but also think about it from their perspective. How am I seen? How is my advice coming through? Am I giving them something that is not achievable to them? I want to think like they are thinking,


Describe a time when you had a breakdown that led you to a break through.


A low point was when I was running a brick-and-mortar business. When I looked at my bank account, I had $3, in my bank account, that was all I had to my name. The business had bills coming in, payroll, rent and I knew that there was no way I could do it myself. Working hard is usually what people would say and how they got out of it. But I swallowed my pride and started telling people the situation that I was in and asking for help. With their help, I was able to make it through.


What steps do you take before you make an important decision?


Before I make an important decision, I will typically try to weigh the pros and cons. Not just in the pros and cons list, but looking at the situation from a couple different angles. Generally my answer I think is hidden, usually I see one or two answers. I think the best one is usually the hidden third, or option C. I think that usually takes just a little bit of perspective shifts in that.


Describe your creative process to get new ideas.


My creative process when I'm feeling stuck, is I go on a walk. I'll usually put my headphones in and start listening to a business podcast or audio book. I live near water, which is very beautiful. Usually by the time I get to the water, I have my I have my breakthrough. That comes from just passively thinking about it. Usually getting my mind off of the problem and distracted by something else and my brain works. Even when I don't think it's working. It's working in the background, and I usually have an answer by the time I hit the water.


As a mentor, what topics do you like to mentor others on?


As mentor? I like helping people pursue their passion. One of my first questions with a mentee is usually, why are you doing this? And it's always interesting to hear their answers. Some people are just doing it for money and they will have a hard path, some people are doing it because it solves a problem in their life. Those are the people I like helping the most because they are invested in an entirely different way.


How would mentees praise you?


Mentees have praised me in the past for being clear, and direct. That was probably the same reason they cursed me, because I will tell them the honest feedback! But mainly it’s the area that I've received a lot of praise in.


Tell us about a time when you helped a mentee solve a big challenge.


One mentee that I helped solve a big challenge... she was looking to start a business, she was relatively young. The reason she wanted to start the business didn't make a lot of sense to me. Napkin math just didn't really pan out. I gave her some hard news, I explained to her, I think you have an uphill battle. I don't think that this is going to work. I think telling somebody that, because it's sort of her dream to pursue this, I really crushed her and it was very hard news to deliver and to hear. I think, ultimately, it was the right choice for her though.


Have you ever had an embarrassing moment, early in your career when you thought “Oh, my gosh, this might be it.”


I would say the most embarrassing point in my career, early in my career, I was delivering a live speech in front of a very large group. I got sick on stage. About a third of the way into my presentation, a presentation I delivered before and I knew it well! But, all of a sudden, I could not remember the next slide. I could not remember my next point. I excused myself, I walked offstage. I ended up getting sick when I got out of the building. That was incredibly embarrassing. I did not want to face those people ever again.


What's the funniest, strangest thing you’ve ever had to do in order to close a deal?


I was working with a regional coffee shop chain. They ended up being super short-staffed for a very large street fair that they were manning. We ended up using my pickup truck to haul the milk up to their mobile coffee stand. While driving up there, the vice president ended up pulling the entire crate of milk off of my truck. He was trying to unload it and lost balance of the palette of milk gallons. We spilled about 200 gallons of milk all over the side of my truck and all over their booth. I did that just to close the deal.


What do you do when you feel stressed or overwhelmed? What advice would you give somebody who's feeling stressed or overwhelmed?


The first thing I do is recognize it. Then I will just write out a bullet list. Usually on my phone in notes. I will just make a bullet list of all the things that are floating around. Inevitably, the list is shorter than I think it is because my mind tends to exaggerate all of the things I need to do. After I write it down, I can look at it, I can manage it. I can triage it and prioritize what needs to be done. That helps me tremendously.


If you had to do it all over again, what would you change?


If I had to do it all over again, there are a couple of tactical things and strategic things I would do. Tactically, I would collect people's email addresses from the very, very, first day. Over the years, I've missed out on hundreds of 1000s of email addresses. In today's climate, email addresses are like gold. Strategically, I would have had a better plan, a more realistic plan. I would have looked earlier for partners that can help me and recognize my own weaknesses and find partners that can help me through that.



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