Life After High School: Interview with Jesse Schenk

Jesse Schenk and family

We conclude chapter 3 of my blog-to-book project, Life After High School: Secrets To A Successful Life By Those Who Have Had Twenty Years To Think About It (or) What They Didn’t Teach Us Gen Xers In High School, with a great Jesse Schenk interview. If you missed the last post, click here, otherwise, you can start at the beginning here.

Jesse Schenk

Stanwood, WA

My Life In High School

Jesse Schenk 1996

Who were you in High School and how did you feel about it?

I would have to go with the nerd. Pretty good—I still play video games, just make more money now.

What did you think your life would become when you graduated?

Something to do with money and investing.

My Life After High School

Jesse Schenk and family

What happened in your life to you, for you, and by you in the last twenty years (how have you used your time and who have you become)?

Getting engaged and married is obviously pretty important, followed closely by the birth of 3 children. When we had our first boy Preston I was at the tail end of a career as a professional online poker player. While previously we had done very well, the laws changed and made it very difficult to make good money. When Preston was born I felt the need to not let that little guy down—he needed someone to go kick some butt for him. Since at the time we were living in a garage… that probably wasn’t a high point. I was 27 at the time, no degree, little experience, spent most of my time previously being a top international gamer, but that wasn’t enough money to do anything. My lowest and highest point was probably having ($7.00) in checking and on that day winning $23,000 at poker.

Move on a few months and I landed my first real corporate gig at an aerospace company in Bellingham called Heath Tecna. The first week I had no money for lunch, but it happened to be the week before Christmas so there was food all over, otherwise I probably would have starved. My first paycheck showed up right before Christmas, Preston was 6 months old at the time and $1,200 seemed like a massive fortune. So we moved out of the garage, rented a house up in Bellingham, and I completed a degree in marketing (can’t pass up free schooling).

Three years into this career I started to really grow my skills, right about the time layoffs hit the company. After four rounds I was the lowest man on the totem pole, we had just bought a newer Touareg, oh and added baby number two, my second son Gunnar. So with no job, a few prospects, and a new baby, my wife and I decided to take an offer down in Longview, Washington at a paper mill.

I exceeded all expectations placed upon me during my time at Kapstone. My bosses boss did the first evaluation and told me he would have given me perfect scores across the board except that had never occurred in the companies history (his words not mine). But Longview is no place to raise a family, in my opinion, just too many drugs. So I turned down a massive raise (seventy-five percent boost) to come back north and back into aerospace.

During this time my wife and I only had one car, we had no furniture, we slept on an air mattress while the kids had beds, new clothes, anything. My wife Danielle and I would sacrifice anything for the kids, although we made quite a bit more money than the median income for the area. So we packed up and headed north, the day we moved I for some reason didn’t eat, or drink and by the time we got to our new house in Arlington, Washington and I drank some water out of the tap; it was the most delicious water I had ever tasted. A new chapter had begun.

Working for B/E Aerospace my skills in finance and Excel become well known in the company of five-thousand. Often I was seen as the expert to solve any financial program problems, being a wizard with Excel (all seemed pretty simple to me but others were impressed). So with things going well we decided to buy our first house. So in 2010 we found a brand new foreclosure that had never been lived in and we snatched it up. Our broker felt it was one of the best deals he had seen in twenty years (we learned later our deal ruined a few other sales for houses the were smaller and more expensive than what we had bought).

Still, with B/E I got promoted way up the ladder to take over as the acting controller for a new $1B lavatory program for Boeing. But the higher up I got in aerospace I realized the less I enjoyed the work. Meetings, closings, power points, meetings, closings, power points, blah blah blah, boring. Through a few connections, I got offered a COO position with another smaller aerospace company. It wasn’t more money, but the title was an upgrade from being a Manager of Contracts. I should have never taken this position, the company was a nightmare and the CEO couldn’t handle being wrong. Despite bringing in record levels of profit and savings I was fired (something that had never really happened).

Oh, let’s mention we just had a new baby girl right before getting fired. Yes every time I have a child I have a career setback, but now the factory is closed so no worries. So we had some severance coming (always make sure to negotiate for this guys) and we took some time off. I had new job offers in aerospace but at this point, I really wanted to say, screw it, let’s do something else. So I joined a small tech firm as a Financial Analyst (never be afraid to take a step back to take more steps forward). How messed up that company was I could write an entire book, but after basically saving the company from financial ruin I was offered a CFO position. Sweet we are back on top, and the game continues.

I currently reside in the CFO position, I just completed a new Series C for the company, I have 3 kids, happily married. Just completed another BS in Accounting (I guess CFO’s should have this hahaha), probably going to knock out an MBA. Looking to sell the house (big financial crisis coming, ask me why anytime). Gearing up for my next adventure with a health care startup that I am founding.

My Life Lessons

What were the major life lessons and wisdom that you gained during your journey over the last 20 years?

In my family, we live by a few simple phrases, and something I like to instill in my kids. Our children are going to grow up and work in a very unfriendly world. It will be much more difficult to get ahead in that world than like anything we have seen. There will be opportunities for the haves, but there will be more of the have not’s.

Phrase 1: Go big or go home. If you are going to do something make it spectacular, either a massive failure or a massive success either is fine.

Phrase 2: When the lion wakes up in the morning it has to run faster than the slowest gazelle or it starves. When the gazelle wakes up in the morning it has to run faster than the fastest lion or it gets eaten. The point is when you wake up, you have to start running or you will starve, or get eaten yourself.

Phrase 3: Compassion above all. Striving to be great means helping those along the way. You do not need accolades, or thank you’s. You do it because it is the right thing to do.

Letter To My High School Self

If you could write your 18-year-old self (or however old you were when you graduated) a letter, and send it back in time, what would you say? What lessons, wisdom, encouragement, or warnings would you give yourself?

Let’s see, first off when you get offered to go play Starcraft in Korea and represent the United States but you let your dad cancel your ticket… DUDE GOO!!!! Who knows what adventure you would have had.

Second, you’ll learn this in a few years, but you don’t have to be a smart asshole all the time. Be the dumbest guy in the room—you get a lot more information this way. Go find a company called Amazon in Seattle, put all of your money into them, in February of 1999 sell all your shares, then in 2000 buy back in and you’ll make millions. Oh and then go find another company called Google… invest BIG!!! Make sure to track down Danielle Sprehe, she’s amazing and the only one that will put up with your crap—marry this girl.

Hey it’s 20 years later and we are doing pretty good, you have some kids (I know crazy right). Go have some fun. You worry and think about the future too much, and money isn’t everything. Not everyone is as lucky as we are. Help those along the way, give credit to others, and remember that a rising tide lifts all boats… Think about that you little punk.

Thank you, Jesse Schenk. That’s it for Chapter 3. Next time, we’ll dive right into Chapter 4: Teacher’s Pet.


Are you from Generation X? I want to hear what you think! Please comment below and participate in the conversation about What They Didn’t Teach Us Gen Xers In High School. What do you wish someone told you when you were eighteen?


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