Forever Employable Stories: Stephen Shedletzky, Brand Director and Igniter at Simon Sinek

Posted on June 10, 2020.

In anticipation of the launch of my new book, Forever Employable, I’ll be sharing a series of interviews and stories from people from all different professions who have created a platform for themselves to make them forever employable. In this episode, I speak with Stephen Shedletzky, brand director and igniter at Simon Sinek.

We succeed because of the people around us: how a business school graduate went to the bathroom and bumped into the job he wanted most

By all accounts, when he graduated from college Stephen Shedletzky already had it made. He had been accepted into a management training program at a top firm and was quickly headed into the business world. There was one big catch: Stephen’s definition of “leadership” differed greatly from what his new employer was teaching him. Disillusioned and disappointed, Stephen began looking for alternatives. He quickly discovered the work of Simon Sinek and found it deeply inspiring. Following him and his work, Stephen literally bumped into Simon — in the bathroom. After a brief hello, he returned home to figure out how to engage more with Simon and his work. 

Stephen questioned how he could get a meeting with Simon and be more involved with his mission. The answer, as in many of the Forever Employable Stories, is persistence and perseverance. A cold email he created opened the door for him. In that email he made 5 points:

  • This is how you know me (how we met)
  • Here’s why you inspire me
  • This is my experience of your brand
  • Here’s what I’m inspired to do and advance it
  • Here’s the story I tell myself of how you can help me

Can I buy you a coffee? Can we chat for 15 mins?

That email got a response! From Simon’s auto-responder. Undeterred, Stephen continued to build his network and communicate with Simon — often unilaterally. Eventually, this persistence bore fruit and Stephen has been working with Simon now for 10 years. 

Throughout our conversation, forever employable themes kept surfacing. We’ve already touched on persistence and in addition Stephen points out how self-confidence is something you develop. No one is born with it. He points out that success is never overnight. Give your ideas time to grow roots and bloom and that ultimately, the more you give away the more you get back because it builds your network. 

Ultimately, Stephen says we succeed because of the people around us. Planting a flag and building a platform is a good start but without the network of motivated, supportive and energized people around you it’ll take more time to succeed. Consider that as you watch this engaging interview with Stephen and myself. 


JEFF:    My guest today, all the way from Toronto Canada, is Stephen Shedletzky who is going to tell us all about himself. I’m going to see if we can uncover more ways and more nuanced ways to continue to think through how to build the kind of platforms, networks, and communities that help us become forever employable. Can you give me a little bit of the TLDR of yourself and your career?

STEPHEN:        My career started with pain. I thought I’d be pleased with the first job I got. It sounded great. I got it out of business school recruiting. I won that and it turns out that I neglected to ask them how they defined the term leadership. I joined a leadership development program and I went, “Leadership. I love leadership. I love studying leadership and I love practicing leadership.” To me, the definition of leadership is serving those in your span of care. I thought that was the definition everyone was operating with. It turns out, there is no standard definition of leadership. The first corporation I joined, it was more P&L authority where you white [0:02:34 male?] and had gray hair. Because of pain, I felt uninspired, disengaged, unmotivated. I knew something was amiss. At first, I made myself wrong for it. Like it was the first time in my life I made a choice that wasn’t panning out. I made myself like, “What did I do wrong?” Rather than how is this environment perhaps not for me?” Not an evil entity. Just not a right fit.

Then I was introduced to Simon Sinek’s work and his vision of a more inspired, safe, and fulfilled world and I went, “Uh-huh. That’s what I want.” I knew it already. He just put into clear words for me. I got lucky at the right time, right place. I’d be doing this work of helping people find what inspires and engages them and help them do it; not just for them, but for the people around them. I’d be doing this anyway, but fortunately, I collided with Simon and we’ve been doing this together for over a decade.

JEFF:    This concept of getting lucky is a really interesting concept. I talk about this in the book. There’s a quote that’s overused but it’s a good quote. It’s the quote from Seneca, the philosopher. He says, “Luck is where opportunity meets preparation.” People will be like, “You’re so lucky you bumped into Simon Sinek.” Or I get, “Oh, you got offered a book deal. You’re so lucky.” It’s about opportunity meeting preparation. Talk to me a little about that. Right time, right place. What was the opportunity and how did you prepare yourself to take advantage of it? Tell me about preparation meets opportunity.

STEPHEN:        I can tell the story of how we met. I experienced pain. I was introduced to someone by the name of James Powell who very quickly became a mentor. It was July 2010. I was miserable in my career and I was searching desperately for answers and a new path. A mentor introduced me to this guy, James and the next day we met for dinner. When does that ever happen? I said to him, “James, I’m afraid to…” I was being moved into a marketing role for this first company I was with and I said, “I’m afraid to move into marketing when I don’t believe what they sell and how they sell it.” He said, “Watch this TED Talk” and he sent me Simon’s TED Talk. I procrastinated for two months and then finally watched it and went, “Oh, everything you say to be true; I haven’t thought about it that way.” Some months later, November, I went to a conference in Toronto to hear Malcolm Gladwell speak, and right before Gladwell, and literally, the cover boy of the conference program was Simon Sinek. I went with some friends and they’re like, “It’s your boy” because I was already drawing golden circles and espousing his work on napkins and any opportunity that I had to speak about this guy Simon because his work represented mine.”

To your point, for sure, luck. I went to go to the restroom after the conference and bumped into him. He was a lot shorter than I thought he would be. He didn’t know me from Adam but I said, “Hey, I was that guy who asked you that question about this.” I asked a question during Q&A. He was very kind, shook my hand. I wrote a little article about him on my blog, I had at the time, for young professionals. I write him a message on LinkedIn. I say, “I’m going to read the book.” He writes back a couple weeks later on LinkedIn. I now lead the team that responds to people who write in on LinkedIn which is hilarious. He said, “I hope you enjoy the book more than the talk.” I was like, “Probably not possible because I don’t like reading that much.” I read this book and I think a big piece of it is there needs to be sincerity. I legitimately care about this guy’s work. If I was just doing it for me and to get ahead myself, he’d see through that at some point. I read his book. Loved it. Started listening to any podcast or interview. I wrote back to him this five point email of, “This is how we know each other. This is why you inspire me.” And if you get this right and they’re legit, they’ll keep reading. If you get it right but they’re illegit, they’ll put it away. And I said, “Here’s what I’m inspired to do because of said inspiration. Now I’m trying to advance what you believe. Here’s how I think you can help. Can I buy you a coffee?” I got a response immediately and it was his auto responder saying, “I no longer respond to professional email.” There were three people listed on who to respond to. The first one was about corporate partnerships. I’m like, “I’m not that big of deal. I’m not going to play that card.” The other two, a guy by the name of David Mead and a lady by the name of Danielle Summers. I wrote to David and Danielle and Danielle wrote back and set up a time for Simon and I to continue the conversation. David wrote back a day later saying, “Sorry, he’s busy.” I’m like, “But no, Danielle told me I could.” I felt I was asking to go to the bathroom in kindergarten. Simon agreed to meet and continue the conversation and I literally asked him, “Why would you give me this time?” He said, “I get the sense that you’re a giver. I get the sense that this isn’t for you. I get the sense that you care about my work and you want to advance it.” That was like 10 years ago and bit by bit I started doing some work with him and his team and now we’re here.

JEFF:    You wrote him a five bullet point email. This is a really interesting tactic. This is how you know me. That’s how we met.

STEPHEN:        Or so-n-so, you know, Eric recommended I reach out. Some sort of a, “I’m not just a random kook.” You can create some form of relationship.

JEFF:    You were a little bit random.

STEPHEN:        Yeah, I think I said, “I was the guy who asked you this question at that event.” He probably did three events that week and had no idea who I was, but some form of credibility.

JEFF:    Here’s why you inspire me. Give me a sense of what that entails.

STEPHEN:        This is what marketing is. It’s people’s experience of your brand. I wrote back to him, “This is my experience of you.” Simon is an open book. He makes it very clear what he’s about. His vision of a more inspired, safe, and fulfilled world, I want to live in that world.

JEFF:    The next  thing you said was, “Here’s what I’m doing with your content.” Did I get that right?

STEPHEN:        Because of said inspiration above, here’s what I’m inspired to do and contribute and advance it.

JEFF:    The last one was meet for a coffee. What was the one before that?

STEPHEN:        Here’s how I make up that you can help me. Like here’s the story I’m telling myself about how you might be able to help me. So oftentimes, I get notes from people that hit the first couple like, “Hi. I’m so inspired by this. Here’s what I’m trying to do. I need your help.” It’s kind of like, “You don’t know me.” It also establishes like, “I’m really attracted to people who are going to be doing this with or without me.” I established, “I’m not expecting your help. I’d love your help but if you can’t, that’s okay, and I’m still going to charge ahead. Like I’m going to strive to be successful on this pursuit with or without you. If it’s with you, great, because you already have momentum on the thing that we both care about.”

JEFF:    Then let’s meet for coffee; the call to action, right?

STEPHEN:        Can I buy you a coffee or can we chat for 15 minutes? You always ask for 15 because if you ask for 30 or 45, it’s like, woah. If you ask for 15 and by minute 14, they’re really enjoying it, they’ll give you another 15 minutes.

JEFF:    Did Simon read this email?

STEPHEN:        I doubt it. Maybe it was shown to him as a glance and he went, “Yeah, let’s do it.” I never asked him that. I reached out in the first couple weeks of January. We had a phone call scheduled for February. It then got pushed out to April. The good news about that was I spoke to him on a Tuesday or Wednesday. That Thursday, I was flying out to New York for a weekend vacation. It was supposed to be with my girlfriend and then it became with my brother because that girlfriend became an ex. I asked him in that phone conversation, “Why did you take this call?” He said, “I got the sense that you’re a giver.” Whether he remembered meeting me or took a scan at my email, but it was these two people, Danielle and David, who took a look. David has since become a best friend and I’m now working closely with Danielle on a new product which is fun.

Two, three days after I spoke with him on the phone, I was going to be in his neighborhood. I said, “Can I buy you that coffee?” I joined him and his family on a charity walk. Apparently, I was the very first fan who was ever invited to do something in his personal life. I had no idea at the time. I was like, “Why did you do that?” It’s been fun.

JEFF:    I like your perseverance. One thing we see throughout all these stories is a level of perseverance. You read the material. You went to see him speak. You sent him an email. You followed up with the people. You didn’t get put off by the auto responder. You followed up with the people who were in the email. You continued to follow up. You got the call scheduled. It got deferred. You got it rescheduled. Then eventually, you made this happen. That’s something that gets lost in a lot of these conversations when you see people’s success you want to emulate. The conversation around perseverance gets lost.

I remember going to Greece to speak in the early days of the Lean Startup movement. He always talked about the montage. The montage was the part where the entrepreneur had the idea; where the idea was successful. In the movies, they do a montage of all the hard stuff in the middle. It’s like 30 seconds of music and sweats and disappointments.

STEPHEN:        That’s the journey.

JEFF:    But that’s the journey. That’s the work. We all too often, we get that montage where that’s the thing we should expand; the beginning and the end less so important is the journey that becomes interesting.

STEPHEN:        The thing I love about Simon is he’s done well and you mentioned his success or people who’s success you wish to emulate. The thing I love about Simon’s success is it’s primarily not about him. There are benefits to his celebrity or fame, but predominantly he’s someone who stands for something bigger than himself. He represents a movement but it’s not all about him.

JEFF:    In the book Forever Employable I talk about several qualities that help folks become forever employable. My goal is to teach people that the qualities that I’ve discovered in myself that have helped me become forever employable are in them as well. A lot of folks don’t see that in themselves. The qualities I’m specifically talking about are things like entrepreneurialism, self-confidence, continuous learning, continuous improvement, reinvention. A lot of folks don’t see that in themselves. I didn’t see them in myself. I want to take a look at a couple of these different qualities and get your take on your perspective on them. One of the most important things is self-confidence. People hearing your story will say, “This guy has a ton of self-confidence. He’s not afraid to email the guy he wants to work for and the guy who inspires him and persist about that.” Can you share a story that has helped you develop your self-confidence to where you said, “I’m just going to email this guy and persist until I get an answer?”

STEPHEN:        The funny thing about self-confidence is no one is born confident. I think confidence comes from the relationships that we have around us; same with courage. There’s one instance that stands out for me. I have a great relationship with my dad and my dad is not one of these lovey dovey… Every one of us has the same number of emotions and we’re all emotional but some of us are more emotive and some of us are less emotive. I’d put him toward the less emotive. I was still living under my parent’s roof. I remember when I was in my first couple of jobs and miserable. I kind of said to myself, “Oh, if I just moved out and moved into an apartment or condo, then I’d be happy.” Boy, am I glad I didn’t do that.” I ended up leaving corporate and went on my own version of my own MBA which is I was clear on what I wanted to pursue and I chose to live in my parent’s basement to pursue it. I lived under the poverty line based on the income I was pulling in. Fortunately, I had room and board. I was lucky in that regard but I used my luck to pursue something that I cared about rather than just myself.

I remember I was six months into starting out on my own and I thought success would happen quicker than it did. The quality of the people I was meeting and the quality of the conversations, they were great. I knew I was moving in the right direction. I was clear on why but I had no what’s. I knew what step 10 was but I was very clearly at step 1 or 2 and I had no idea steps 3-9. I thought I would just go. I thought I’d have clients, a coaching practice. I thought I’d have consulting gigs and speaking engagements. It just wasn’t happening as quick as I thought it would. Sort of in a moment of vulnerability, I remember one evening saying to my dad, “Dad, what if this doesn’t work out?” My parents were hawking me quite a bit to try to stick on the path. I was with a couple large, successful organizations. I could have built a nice, secure path. “Why don’t you just try an internal transfer, son? Go work in human resources.” I’m like, “Thanks for trying to help.” They don’t have business in their background. They were limited in how they could help me, which was really hard for them.

I remember saying to my dad, “What if this doesn’t work out?” He said, “Give it two years. Anything that you’ve put your mind to, you’ve been successful at. Give it two years.” I get emotional just thinking about it. Here’s this person who I respect deeply. He doesn’t really understand what I’m doing and trying to do but he understands that I care about it deeply that I’m willing to take big risks on my own career path. It was kind of like your investor being like, “I know you’re not seeing returns yet but I believe in you. Give it a bit of time. Six months isn’t a fair sample. Give it two years.” It was so liberating. By the time I hit that two year mark, that’s when I joined forces with Simon and things started moving. It hasn’t been lollypops, sunshine, and rainbows with Simon over these past 9-10 years but it’s been a great growing journey and I’m so delighted where I am in my career right now.

JEFF:    Amazing. It’s really nice to hear you say that because one of the things I talk about in the book is a two-year cycle. If you want to start to establish yourself in some kind of ability in a particular space, my experiences taught me that at least two years is what’s necessary to really start to establish some credentials in that space.

STEPHEN:        And learn.

JEFF:    And learn, exactly. Part of what you do is building a network and really growing a network around an idea, a process, ways of working, a methodology, a vision, or mission in this particular case. What have been some effective tactics in growing the network and why is it important to do that?

STEPHEN:        We’re a tribal species. We succeed because of the people around us. I look at every success I’ve had in my life and I think there is a very strong correlation between people taking risks on me. Trust. The very reason we’re having this conversation is because of networking. A mutual friend, Bryan Wish, he’s someone who wrote into our company website at the time I was doing customer service. He was in college at the time and struggling with what does he do with his life? Should he go the path more traveled or should he follow his instinct and gut and go stray? He knew his answer. He just needed some permission to go do it. He thought finding his why, his purpose would help. Here’s someone who writes in and quite frankly, I read his email and I saw myself in him. I went, “I can help this guy.” My j-o-b dictated that I should write him back a response but I said, “Hey, do you want to hop on a call? I’d be delighted to chat.” I helped him out. I gave him access to our online Why Discovery course. He found his why. I mentored him a little bit and was just a listening ear and reflected back what he already knew but sort of gave him permission to forego the high paying corporate job and go do the thing that he was so passionate about while he could. I kept showing up and supporting this guy because I have a value of feeding the hungry. I really want to help people who want to be helped. I find it so attractive. If you want to improve, I’ll keep showing up for you if you keep showing up for yourself. That was 6-8 years ago. He would always ask me, “What can I do to pay you back?” I would say, “Pay it forward. You will meet someone, at some point, who you see yourself in them. Just help them.”

Bryan has gone on to build a very successful career. He started his own firm. It’s coming along. Now he has all of these press and media opportunities and whenever he has a client that’s great or he does an interview himself, he always sends me an email saying, “Stephen, I think you’d be great for this.” I help this guy, not for me, but for him. He’s asks me, “How can I repay you?” It’s like, “If I ever have something that I need from you, I will ask, but I’m not doing this to get something back from you. I’m doing this because I believe in you.” We formed this great friendship, even brotherhood. He is constantly looking to send opportunities my way just because we believe in each other. That’s networking which is really making friends and particularly when you share similar values and beliefs.

JEFF:    We’re living in weird times. Global shutdowns, pandemics, Coronavirus. Forcing people to really look deeply at their core value and finding new channels for distributing or sharing that value. What have you been doing during the lockdown to stay connected, to keep improving, to keep work moving forward in the face of the reality we’re facing right now?

STEPHEN:        When I was in my early-20s and I became very clear on the work I wanted to do, I made a conscious choice and I said, “I’m willing to struggle for 3-5 years instead of climb the ladder that others think I should climb. I’m just going to make my own.” Such that, in 5-10 years from now, I’ll be known as the guy who helps people feel more inspired, safe, and fulfilled at work. Build a brand around it. What’s fun is, as the years have gone on, people have been reaching out to me for the right reasons. I’m talking about people that I haven’t spoken with in like 3-5 years and they’re asking me to do the work that I love doing which is fun.

To answer your question head on with the Corona times, when this started in March, the vast majority of our revenues came from hopping on planes and going and doing live events at conferences with organizations. That all shriveled up. We’ve not let go of a single person. We’ve not done furloughs. We’ve kept everyone’s salary the exact same. We pivoted. We’re still doing a little bit of B2B work and it’s coming along but it’s not as rampant as it was. We’ve pivoted into B2C. We know there are people who believe in this work and want this work for themselves. We’ve not done a great job of serving them in the past, quite frankly, because we didn’t need to and now we need to. We’ve always been very open source and provided our tools for free or reasonably priced so people can get stuff, but we’ve never really built B2C.

We pivoted and opened up live online classes. We took what we did in the live room and made it on Zoom. We have these live classes. You can come on. You can find your why. You can figure out how to live your why. You can work on your leadership. You can work on building trust. We’ve built this new marketplace where anyone can come on their own or with their team and work with us and work with peers. We pivoted with purpose. The definition of pivot is to move around one central thing. The thing we’ve chosen to move around is what now can we do to help advance our vision of a more inspired, safe, and fulfilled world?

JEFF:    Thank you so much for your time. This has been amazing. Your stories are super great.

One thought on “Forever Employable Stories: Stephen Shedletzky, Brand Director and Igniter at Simon Sinek

  1. This has been a very timely and relevant. This made me feel knowing both of you for long time that enable me to reflect and understanding how survival is all about. Having a real purpose is easy to be said by all but what is your heart desire that enable you to find a true meaning and happiness is a journey that we all should be taking along the the way. Thank you

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