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Tate HackertFebruary 18, 20228 min read

ZZ Culture: How to Mentee

avatar Tate Hackert

Tate is the brain behind ZayZoon, developing the idea of providing access to funds before payday, in 2013. He feels gratified knowing “we get to improve the financial health of people each and every day.” One of his favourite ZayZoon experiences involves a business trip to Selinsgrove, Pennsylvania where he helped film a Holiday Inn Express testimonial video. Wearing a ZayZoon shirt at the local Walmart, someone saw Tate and exclaimed, “Hey, ZayZoon! I use that!"

Networking is something that was ingrained in me. I remember being at Tim Hortons with my dad at 6 am after early morning hockey times and my dad would say, “be mayor”. He would encourage me to go chat with kids I vaguely knew from the other teams - congratulate them, ask them how the game felt for them, or whatever other conversation topic got them comfortable. He knew the value of that saying “It’s not what you know, but who you know” and that the more people you know and interact with, the more you can learn and improve. 

As I got older, I sought out mentorship more than anything. Though truthfully, I’ve always thought of networking and mentorship as somewhat interchangeable. This is because for me personally, my networking is with the goal of connecting with people more accomplished than myself, and/or with thoughts that I can respect and find inspiration or challenge in. “Networking” is a word that has unfortunately become so cringe. Surface-level, transactional interactions that most people approach with a quantity over quality mindset. 

By using the term mentorship instead of networking, I believe it puts an inherent level of respect on each interaction. You begin to view it as it should be — relationship building. 

At the end of the day, the goal is to connect and build relationships with other individuals who bring value and learnings to your life in a positive way, and you to them.


How do you know what you want in a mentor?

The simple answer is that you probably don’t. Like most relationships, it will kinda just form and what you think you wanted, maybe completely different from what you actually appreciate.

In 2010, my second year at the University of Victoria, I knew nothing more than the simple fact that I wanted to learn and have a forward momentum that the classroom wasn’t providing to me. Instead, I started reaching out to every “business” person in Victoria that I could. 

At the time, I was running a side business lending money, mostly through Craigslist sourced leads. I would put an ad up and within hours I would have hundreds of emails needing to be sifted through and run through my own little underwriting algorithm – my brain, heart, and some pen and paper. I started to get quite good at it and even extended my own credit to meet the demands of customers. I didn’t know exactly what I was searching for in a mentor, or what this business could become, but I knew I was onto something and had specific questions about taking the next step that I wanted to get advice on. 

My class schedule quickly changed to scheduled coffee dates, and later, during my final semester of University while abroad at the City University of Hong Kong, I spent much of my time at Meetups and forming relationships with classmates that went beyond partying. Practice really does make perfect. I was quickly able to figure out what I was really looking for and how to navigate a new conversation - a new type of relationship.

During this same time, Tim Ferriss would release a blog post, “How to Create Your Own Real-World MBA”. I didn’t know it at the time, but a lot of what I was doing had this in mind. Being somewhat related, I would encourage you to give it a read. 


I don’t want to be an entrepreneur. Is mentoring still for me?
Of course, it is. Mentorship is just a solid relationship that brings value and learnings to your life, remember?

When seeking a mentor, however, It is good to go in with an idea or interest and be as specific with it as possible. Are you looking to improve your management skills? Trying to navigate your career? Are you at a struggle with your diet and exercise? 

Challenges are good to bring to a conversation because those challenges normally come with a sense of vulnerability, and create space for learning to occur. Having a specific problem set not only helps get the conversation started, but it allows you to riff on something together.

If you engage in a conversation with intent, you’ll find yourself very quickly flowing and likely take away much more than expected or learn you want to dive into a completely different topic than you first had in mind. Still, the start of a topic-less conversation can be intimidating and seemingly awkward. Luckily, there are some prompts that can help you with this. More on that below.


Cool, so I want a mentor. Now how do I find one?

Like any good relationship, you need to put in some time to find mentorship. You’ll want to book a few dates and begin to learn how to navigate this new type of relationship. You’ll need the experience to figure out what you like, and what you don’t. You need to be on the same wavelength as your mentor for it to work, and it needs to be a symbiotic relationship - one where each of you benefits.

Be aspirational. Seek out someone you idol. Try and connect with someone that is doing something that interests you.

 A few ways to get the ball rolling:

  1. Talk to your existing relationships about your challenges and ask them if they know anyone else they think would be great work for your challenge.
  2. Ask people in your existing network for an introduction to a specific person. 6 degrees of separation is a powerful concept. You’d probably be surprised who knows who.
  3. Send messages on LinkedIn, Facebook, Twitter, email… be shameless. One of ZayZoon’s current board members was a relationship that started 9 years prior from numerous LinkedIn and Facebook messages. It was also the same person that put me and Darcy together. Another ZayZoon board member can be traced back to Twitter messages and twice removed connections.
  4. Attend meetups, go to co-working spaces, “be mayor”. When you put a positive vibe out into the world and treat each interaction with quality instead of quantity, you might be surprised by what you get back.

Like most things, just starting is half the battle. Once you do though, it snowballs on itself. You might have a conversation with someone you don’t particularly connect with, but if you approach the interaction genuinely looking to learn and with an eagerness to improve and challenge yourself, chances are it will lead to something else.

It’s funny like that. One thing leads to another. Just get started.


But wait, If I’m trying to connect with people more accomplished than myself, what value do I bring?


First, “accomplished” is a broad term. Just because someone has found business success or success in X doesn’t mean it’s the only blueprint. It does not mean they have all the answers. It doesn’t mean what they did 10 years ago would work in the same way today. 

Second, be confident. You’re a driven, smart, and accomplished individual yourself. If you weren’t, would you be having a conversation with this person? You’ll bring viewpoints, information, and interesting questions that engage the other side of the conversation. Step out of your way and drop the imposter syndrome. 

Third, people love to help people. It makes them feel good. It strokes their ego. It gives them purpose. Sometimes giving back is enough. 

Alright, so what are some tactics for messaging and first conversation?

Never ask someone, “Can I pick your brain?”.

Don’t be too general, and try to be concise. 

Focus on the specific problem set or aspirations you have. 

For me in University, when I was trying to connect with people in fintech, my (cold) emails went something like this:

“Hey X, I’m a student at Uvic that has been lending money and now wants to dedicate my full energy into a fintech business. I’d love to speak with you about your career up until founding X, some ideas that I have around getting people paid quicker, and get any advice you may have for a young individual such as myself.”

It wasn’t perfect, and obviously, quite niche in subject and in timing, but there are a few key points that make it work. 

  • Concise and to the point
  • Provides credibility and shows effort and initiative prior to getting advice
  • It’s aspirational 
  • It offers a potentially new perspective for them

Lastly, make it easy for them to say yes. This is sales 101. Provide them times to pick from. “I’m available Monday, Thursday, and Friday at 11 am and 2 pm. What time and day works best for you?”

How do you navigate the conversation once you get to the meeting? 

  • Be open and vulnerable, if you don’t have something specific you’re trying to figure out, tell the person that. Tell them you don’t really have an agenda but really are just having difficulty with X or wanting to challenge yourself with Y.
  • Listen, really listen. Don’t worry about notes beyond the odd point. Just have a conversation. Write your thoughts afterward.
  • Have them tell you their story. This is a great opportunity for you to interject with questions. The learnings you will get just from this will be plenty.
  • Share your challenges. Dig into them. 

What about ongoing conversations?

  • Do your homework. If your mentor gives you a takeaway, make sure to take action on it quickly so it’s part of your follow-up conversation.
  • Meet on whatever schedule makes sense. I normally would try to meet every 3 weeks. Sometimes it would be 1 week, sometimes it would be 3 months. No real rhyme to it. Whatever feels natural, however, if you think you’re being annoying or bothersome, you probably aren’t. Most successful people can set clear boundaries and will tell you very clearly if they need some breathing space.
  • This is a mutually beneficial relationship, so share learnings back as well. That podcast episode you listened to that reminds you of some topics you covered? Send that with some notes and time stamps. Best case scenario it is a learning for them. Worst case scenario is it showcases your eagerness and coachability. Your mentor will want to dedicate even more time to your relationship. 

Just get started

Hopefully, that helps. This is largely speaking from my own experiences and biases. I’m most interested to hear from you, how have some of your best relationships formed?