John Matson & Tina Yip, 5to9 Podcast Hosts

We were connected to John and Tina through another friend, Todd. "Do you know 5to9?" We looked it up quickly and realized we have been fans of the podcast already. Game over after that. Every morning after, we incorporated John and Tina's voices into our Morning Routines.

We are so excited to share the creatives and founders of 5to9 on our Spotlight this week: 

Per usual, what were your dreams and aspirations as kids?

John: When I was five, I told my mom that when I grew up, I wanted to be a turtle, so there’s that. I knew that I loved being active and performing. I would put on characters and voices, and singing a lot. As I started to get older, I wanted to be a musician, and started playing drums when I was 10 years old. I thought for certain that I was going to be in some “cool band” when I was older. I was only partially right, and got to play in “cool bands” in my 5to9.

Tina: You know that kid that knew exactly what they wanted to be since they were five? Well, I was not that kid. But I was very curious. I wanted to know a lot of things and I’m grateful that my parents put me in a position to learn them. Growing up in Hong Kong, it’s the norm to have tutors for literally every subject and attaining more than you need to know for class. So I got put into tons of tutoring classes and learnt a lot. By no means I love to study, but I’ve always been very happy with learning and understanding new things. I also got exposed to the performing arts at an early age, and I went HAM at it. I studied theatre for seven years. I was that theatre kid and had the time of my life. But for some reason I never wanted to pursue it. I guess all I knew was that I was comfortable in the spotlight, wanted to soak up info like a sponge and do something that’s very me. I’m sorry I don’t think I answered your question.

You two have similar energies and are both just full of life! Can you tell us a little a bit how you two got “cnnekted” ?

J: Thank you for the compliment! :D Tina and I got connected a couple years back through the NYC startup community and especially our good friends Josh Ness and Peter Crysdale. Tina was running their event series called StrategyChat and I was running marketing for a media startup incubator in Brooklyn. I participated in one of their marketing hackathons and got to know Tina first through that.

T: Omg PUN! I used to host a marketing hackathon called StrategyHack and John participated in one of them. That was three years ago now! Wow! Time flies! We hung out around the same circles and became great friends!

Obviously there was an “ah-ha” moment that inspired you to start the show. John, was your day gig a big influence on this side-hustle break-through?

J: Tina had actually inspired me! She had started a blog named Side and Seek that showcased her friends working on cool projects. She approached me about starting something new that could give it more voice (get it?!). A lot of the “ah-ha” moment came though from when we were starting to brainstorm around the concept more. Not only did I realize that this was a concept that I felt extremely close to, it was something that I advised people on a daily or weekly basis. Many of the entrepreneurial concepts I would get pitched were… well-half-baked, and really needed some more time in the oven - which is what side projects can be for! I was also doing two bands on the side, which made me connected to finding creative outlets that allowed me to expand my horizons, skill sets, and friendships in a completely different way - which is something ELSE that side projects can be used for! I was tied to the concept of self-fulfillment and cross-experience education in everything I did. 5to9 in itself is a way to do that, one to share the power of that concept with others, but also continuously learn from our guests on our show and the amazing people we meet who connect with the idea of fulfilling themselves with creative passions.

Tina, you’re the newest strategist at a very notable agency. How impactful is your day job when it comes to your off-hours hustle? Is there any correlation between the two?

J: Heyoooo, Tina, waddup?!

T: I like to think of work-life balance as more work-life integration. I’m grateful to be at a job where I’m constantly learning from people around me and through the work I do. I often use the frameworks that I learnt at work in my side projects and vice-versa. Instead of separating the two, it’s a win-win to find ways to benefit both sides. Of course, I’m respectful of my employer and will never work on my side projects during work hours, but it’s common for me to use the soft skills that I’ve attained or connections that I’ve made on the side to help my full-time job.

Can you two share some of your favorite advice from your interviewees and memorable moments?

J: Some of the more actionable advice that I found really interesting was in our episode with Chris Baker, Creator of He says that people can get themselves to get their projects off the ground by considering themselves “producers.” Once you start pooling together the skills of others, you can do a lot more, a lot faster, and a lot better. I think that particular shift in mindset can alleviate some fear of knowledge gaps, and help incentivize people to get things started right away. Another piece I keep with me a lot is from our episode with Allison Esposito, founder of Tech Ladies. She talked about drawing parallels in your life and in the knowledge and skills you develop. I can think of both very tangible activities, like project managing branding projects, to be very transferable from one project to another, but there are also intangible skills, like working with artists and the creative process, that I felt comfortable with only because of my time in the bands I played in. There’s a lot to the concept developing yourself as a person through these projects that allows you to see who you are and who you are becoming.

T: I’m paraphrasing, but here are my favs:

  1. “Whenever you feel stuck, change up your routine. You never know where you can find inspiration” - Lianne Sheffy, Ep. 4

  2. “Think of your projects as sand mandalas. It’s about the process, not the result.” - Ariel Viera, Ep. 8

What about your advice to those dreaming of starting a 5to9?

J: Make your first deadline first thing, and rely on someone else to make you accountable for it. The “just do it” piece is really consistent across people we speak with, but some people need techniques to get their wheels turning. Just make a to do list and then a deadline for when you have to get that first task done, and work towards that to start. Don’t be afraid of baby steps, you’d be surprised how momentum can snowball!

T: Start a 30-day project to kickstart your ideas. If you don’t know where to start, listen to Episode 5 of 5to9 where we interview Chris Baker. He talks about the key to starting side projects and where he gets his ideas from. Oh, and read Mark Manson’s Do Something principle. To start anything, JUST DO SOMETHING. ANYTHING.

You will find it and get to what truly draws you along the way.

What’s next for you two both personally and professionally? That may be an obvious question, but are these moves being made with the intention to turn this 5to9 into your 9to5?

J: Doing 5to9 full-time would be amazing, but to be honest, I’m really happy with my 9to5 right now, and all the projects I’m involved with, for that matter. I believe in Voyager’s mission, and the people on my team making it all happen, and what Startup Grind does to bring people together, and what the NYC Innovation Collective can mean to NYC-based entrepreneurs. They are definitely more involved roles than a typical 9to5 right now haha! To me, it is very important that we grow what 5to9 stands for and get people making things that they care about, and thus making themselves happier! If that turns into more involvement, than I’m I’ll be ready for it. :)

T: I’m very happy with 9to5 and 5to9s right now, but who knows where they will lead me. The vision is to keep growing 5to9 and inspire as many people as possible. Too many people forget about the value of their 5to9 time. They mindlessly scroll through their social feeds and abandon their passions or dig deeper into things that they’re curious about. Take that time outside of work and make something for yourself. We’re so much more than our jobs and work does not equate our identities. It’s not even about starting a side project.

It’s about giving more shits about yourself and finding self fulfillment.


To listen and learn more about 5to9 podcast, you can click here and follow them on instagram. You can also talk John here and Tina right here. 

Introduction by Chary, Interviewed by Chary + Emily