Weslie Iza is a jack of all trades who works as a product specialist at a SaaS in Chicago and lives in Uptown. She’s had an untraditional (and exciting) journey; studying abroad in Kenya, beginning her post-collegiate journey as a marketing strategist before teaching ESL in Bangkok, working for the Kellogg School of Management and then completing a 6-month full-stack coding boot camp before transitioning into AdTech/MarTech. Read on to learn the best thing she’s ever taught herself, where she’s traveled she feels she’s learned the most, and what gets her out of bed every day.  

Weslie Iza | Travel and Tech in Chicago

Tell us about your background and how you got to where you are now.

I’ve had quite the untraditional journey. Graduated college after the end of the 2007-9 recession so, while working as a full-time bartender, I took a low-paying hourly job as a marketing strategist for a six-person startup. I ultimately owned their digital content and social media, building an inbound strategy from the ground up. This was when I realized how valuable platforms like IG, Facebook, and influencers, like bloggers, were going to be.

Following this, I moved to Bangkok to teach English as a second language (ESL), returned to Chicago to work for the Kellogg School of Management, and fell in love with the ways tech and software as a service (SaaS) can optimize across the board: efficiency, user experience, accessibility and delivery of products/services, etc. As a result, I took a 6-month full-stack coding boot camp at Northwestern and transitioned into AdTech/MarTech.

What made you want to pursue your profession/area of focus?

An insatiable curiosity and desire to innovate is what initially led me here. Those same traits continue to drive me forward. Passion projects include, but are not limited to: always trying to find a gap or need and determine how I can create something to resolve it. It’s hard to nail down one thing as I’m a jack of all trades. I bounce between many interests. Test – reflect – rest – repeat.

What gets you excited to wake up every day?

Sappiness aside, it’s the simple things. The sun, my fiancé Katy, a good cup of coffee, daydreaming about ways I can generate passive income so I can buy and convert a sprinter van or Volkswagen bus into a mobile boba/ latte/ funky soft serve flavor-of-the-day operation. Don’t get me wrong – I’m a realist, but the idealist in me finds her way to shine daily. 

What’s the best/most important thing you’ve learned or taught yourself? Why?

Setting boundaries and managing expectations. Between these two things, holy sh*t! These can mean so much. Personally, it may mean carving out space for creative hobbies, R&R, finding balance between social time/me time, etc. Professionally, it could be setting an agenda for meetings that too often get derailed, saying no to certain projects, or one that still challenges me: not comparing yourself with others’ limits.

What’s the next thing you’re going to learn or teach yourself? Why?

I’ve always had a strong affinity for healthcare, specifically emergency medical services. Transitioning careers has been on my mind lately, but it may manifest through getting first-aid, first-responder, EMT Basic-certified, or a certification of the like. On a more extreme level, I would love to learn how to fly a sea plane. Speaking practically though, I’d like to expand my understanding of how pay per click (PPC) and bidding strategies work, affiliate marketing, dividend stocks, and possibly blogging (even though writing is far from my thing). 

“An insatiable curiosity and desire to innovate is what initially led me here. That same traits continue to drive me forward. Passion projects include, but are not limited to: always trying to find a gap or need and determine how I can create something to resolve it. It’s hard to nail down one thing, as I’m a jack of all trades. I bounce between many interests.

Test – reflect – rest – repeat.”

Describe a time when you had to ‘throw yourself in the deep end’ and figure it out.

Isn’t that both half the fun and half the battle of life? I can’t say I’ve ever felt like I was being FULLY thrown in the deep end. I imagine this feeling will come over me when we try to have kids. LOL.

Log Rolling - Weslie Iza | Travel and Tech in Chicago

Do you have advice for finding a strong mentor/ building a relationship with one?

Don’t be afraid to ask. When you do ask, be real, and be invested in the relationship. Only you can be held responsible for making it happen. A mentor cannot be expected to provide handouts, be a shortcut to your next job, or keep you accountable.

Favorite resources for ongoing learning?

If I were smart, I’d keep a running list of these in a Google Sheet. I like Robinhood Snacks, online learning platforms like Codecademy and Coursera. Often companies have great learning resources (HubSpot for example). And the ultimate place to go – YOUTUBE

Related: check out our gigantic list of free & paid online learning platforms in tech, creative + travel here!

What’s your favorite spot where you currently live & why?

First Sip Cafe for an iced latte or Coffee & Tea Exchange for hot coffee. Do-rite for the fried chicken sandwich, paired with a glazed donut. 90 Miles Cuban Cafe for dinner + BYOB. Miko’s Italian Ice for dessert. If I’m in the mood for semi-fancy sit down, I love Fulton Market Kitchen.

Related: check out these murals in Chicagoincluding some at 90 Miles Cuban Café – and find a reason to explore!

What’s your favorite travel memory?

This is just unfair. There are countless. A few that are top of mind:

  1. When I was 19 I studied abroad in Kenya. We were in a market, I was cutting sugarcane with a large pocket knife and it slipped on one of the knots. Immediately wrapped the wound (on my thumb) and applied pressure to it. Our driver, two other students (now friends), and our local professor were taken to what looked like a very remote strip mall. I was thrust into a chair, given a shot of anesthesia directly into the wound, and stitched up. To this day I have a very pronounced scar and it is the weirdest feeling whenever pressure is applied to it. Kind of hard to forget, literally!! 
  2. Philippines: the first place out of the country I travelled to alone. I met a friend there, but getting to her was a journey. It changed me. I’ll always be grateful for the experience.
  3. Indonesia: a sunrise hike to Mt. Batur and Scuba Diving in Amed Bali, 
  4. Hawaii: climbing the Stairway to Heaven, hearing whales sing while diving, and stargazing at night on Mauna Loa & Mauna Kea, watching the sunrise from Haleakalā
  5. Swimming with wild dolphins in Nicaragua while getting Advanced Open Water certified (I guess you can say I like scuba diving a lot).

Out of all the places you’ve been, which has been your favorite and why?

I refuse to pick a favorite… Thailand!! It has everything: good food, good people, culture, shopping, parties, scuba diving, beaches, hiking.

Where have you traveled you feel you learned the most, why?

Europe (Germany, Romania, Poland, Vienna, Hungary) – there’s so much rich history. In some of these countries, the war was so destructive and somewhat recent; so much so that you can almost feel it. The revolution, the overthrow and comeback from communist dictatorship, the rebuild/rebirth of the cities, the economic growth. To think that the Berlin Wall was guarded and didn’t come down until 1989 blows my mind. Especially if you try to imagine what people in the USA were doing at that time? George Bush was sworn into the White House, Nintendo’s Game Boy was released, and Seinfeld and The Simpson premiered.

Setting boundaries and managing expectations. Between these two things, holy sh*t! These can mean so much. Personally, it may mean carving out space for creative hobbies, R&R, finding balance between social time/me time, etc.

Professionally, it could be setting an agenda for meetings that too often get derailed, saying no to certain projects, or one that still challenges me: not comparing yourself with others’ limits.

Where’s the next place you’d like to travel (when we can) and why?

“Hey Google, where are the best places to scuba dive with whale sharks?” Wherever that is (like the Maldives). Following that, Glacier National Park, Italy, or Greece. I don’t post often, but if you are ever interested in where this decision lands me, my IG handle to follow along is @theexchangerate

Bonus: what’s one thing you wish people would ask you?

“If you could become the subject matter expert of one thing (a thing that can’t be commodified by you or used to earn money), without having to put in the work to learn it, what would it be?”

The Lourve, Paris - Weslie Iza | Travel and Tech in Chicago

What’s one thing people may not know about you?

I think the six degrees of separation is fascinating. For example, some of mine: Mark Zuckerberg and Fidel Castro. Not sure how to feel about these two, but it’s WILD.

Learn More about Weslie Iza Here

Instagram: www.instagram.com/theexchangerate | www.instagram.com/izaweslie

Lumberjack Vibes - Weslie Iza | Travel and Tech in Chicago