How We Spend Our Money and Different Ways To Invest Yours

While the title of this article might suggest I want to show you how to spend all your money, it’s really an article about the different ways to invest your hard-earned cash.

Let’s talk about voting with your dollars, living a rich and full life, and understanding the fragility of being a human being*.

*Sorry to all of my mammalian and marsupial readers out there. I’ll have your back next time!

Investment for entrepreneurs

To give you a bit of background, my wife, Caroline, and I spent the past few years aggressively paying off $124,000 in debt.

You can read part 1 of our debt story and part 2 of that story at your leisure. During that time, we made some important changes in our spending habits, one of the most important of which was listing out ALL of our expenses and having a hard look at where we were overspending and needed to make changes. (Pro tip: we do this exercise once every few months to make sure we aren’t falling off the financial wagon.)

One of the questions I’ve received the most after we became debt-free was:

Now what do you do with your money??

That is a great question, and I answered it on an Action Army podcast episode that you can listen to here:

But I’m not just going to drop an embedded podcast episode on you and leave you high and dry. I want to expand upon the title of this article and help you spend your money, or at least explain the thought process behind how we spend ours.

The first step to spending (and growing) money is covering all your bases.

Enough well-off (read: rich) people and non-crusty financial planners repeated the same thing over and over again, so I finally started listening and applying their advice.

What were they repeating? Was it a hot stock tip? A slick investment strategy?

Nope. It was super boring. They were all talking about insurance.

You don’t understand the value of having insurance until you truly need it, and by then, it’s too late.

Car insurance

Sure, almost everyone reading this probably already has car insurance. BUT… Do you have the right amount of coverage? Do you know your deductible if you were to get into an accident (and do you have a buffer of cash saved to cover that deductible)? Most importantly: you may be paying for the cheapest coverage possible, but could you pay just a few extra dollars to have WAY more coverage?

Our GEICO car insurance policy had decent coverage every month for the $78 we were paying. But, upon further inspection, we found that we could quadruple our coverage, cut our deductible in HALF ($5,000 to $2,500), and only spend $9 more per month. Yes, $9. Just based on the $2,500 smaller deductible, that extra $9 is worth it for the next 23 years (2500/9, then divided by 12).

Life insurance

We always assumed life insurance was a complete scam. Guys with slicked-back hair wearing ill-fitting suits, trying to get you to buy something you’d never use. That was, until we were told about Whole Life Insurance* and how it not only builds a policy that your spouse (or family) can benefit from if you pass into the next life, but can also be used as an investment account (netting 3-5% returns annually).

Now, you may be like I was a few years ago and not have a spouse to think about when you die. But I bet you have family members who could benefit from the policy if you took a trip on the No Longer Alive Express. And remember, it’s also an investment.

Find a recommended financial advisor (from a friend) and talk to them about life insurance. Avoid investing in life insurance from anyone who calls you unsolicited.

*I want to point out that Whole Life Insurance can get a bad rap on the Internet. You may also find Term Life Insurance in your searches. Truthfully, for every positive article on Whole Life, I could find a competing negative one. At the end of the day, I trusted the people who recommended this to me (close friends and biz acquaintances), and none of them were benefiting financially. That’s good enough for me.

The Oh-Shit-Everything-Went-Cray-Cray-Fund (aka safety net of savings)

Bring on the “snooze” alert. I want you to know, dear reader, I hate the idea of savings. I really do. You’ll read more about that in a moment. However, I hate the idea of being in a financial stranglehold if something goes wrong in life more than I hate the idea of savings.

When we finished getting out of debt, one of the first things we did was build up a reserve of cash (savings). There’s no tried-and-true rule here, but we wanted three months of expenses saved up as an “oh shit, everything went cray cray” fund. This became the first thing we put money toward after paying off all our debt. We squirreled away every dollar and put it—and this is key—in a bank account that wasn’t at the same bank as our other accounts. This external safety net account is one we rarely see and never touch (and that’s how it should be). The peace of mind we feel having this 3-month cushion is absolutely fantastic and something you must do for yourself.

Insurance is boring, so let’s talk about living a rich life and different ways to invest money in your own happiness!

For as long as I can remember, I never believed in saving for retirement. I enjoy the work that I do and want to enjoy my life at the same time. Now, does that mean I don’t make long-term investments? No, but I’m not buying into the same long-term investment plans as other people because I don’t have to. (We’ll get to that in a moment.)

If you knew you were going to die next week, wouldn’t you change everything about your life?

Of course, I’m not going to tell you to spend all your hard-earned money on Faberge eggs, lavish trips, etc. But I will tell you that we live our lives under the idea that human beings are fragile creatures. We get sick easily. We can contract some random illness, and our dreams of a long life can be squashed in a moment.

To me, it’s actually a bit short-sighted to think about living a rich life only when you’re much older. So here are some things we prioritize in our budget:

Travel budgeting

When we finished paying off all our debt, we knew we wanted to do one big trip to celebrate. We called it our “Moneymoon” (clever, I know), and we splurged on a bucket list journey to Tahiti. Yes my friends, over-the-water bungalows and all. This was our only big trip of that year. One trip. The other trips we took were all road trip-based (read: driving in our car to cheap AirBnBs or pet-friendly hotels).

Moorea, Tahiti, Jason and Caroline Zook

(Obligatory Tahiti photo, sorry I’m not sorry.)

As we’ve continued to make a little bit more money each year, our travel budget has increased But we reflect on it each year, and we’re honest with ourselves about our priorities. There was a time our yearly travel budget was $0.00 because we had no money to spend, and it’s likely that could happen again if something more interesting pops up on our radar.

Semi-pro-tip: If you feel like you’re at the $0.00 travel budget place, I’d recommend using a savings app like Acorns. It’s free to use and can round-up your daily/weekly purchases to save little bits of money here and there. You can also set monthly withdrawals (I have $50 on ours). Last year my Acorns account accrued over $1,100 without me even thinking about it! Boom. Travel budget.

Repetitive joy spending (aka monthly entertainment budget)

I believe the reason people (maybe people like you) feel guilty about going out to dinner or movies (or spending money on other discretionary things) is that they don’t budget for it.

When you have an idea of what you can spend on non-necessities, you create a cap for it, and then you don’t feel the guilt of spending it.

We have a $1,000 budget per month for entertainment. That includes:

  • Eating meals out
  • Going to the movies
  • Local coffee shops visits
  • Miscellaneous

Our budget didn’t start out at $1,000. A few years ago, it was something like $150 and included one nice meal and one movie night a month.

Here’s the really important thing about this category of spending: It’s one of the things that brings us the most repetitive joy in our lives. Exploring new restaurants. Seeing works of art on the big screen (or just huge explosions and 360-pans, thanks Michael Bay). We budget this happiness into our lives and are incredibly intentional about it.

I think often of Ricardo Semler’s TED Talk about “terminal days” and how similar it is to the idea of being intentional about how we spend our time. This is a paraphrase of how Ricardo puts it:

“On Mondays and Thursdays, I learn how to die. I call them my terminal days. A lot of people in my family died of melanoma, and I kept thinking that one day, I could be sitting in front of a doctor who looks at my exams and says, ‘Things don’t look very good. You have 6 months to live.’ And I started thinking about what I would you do with this last bit of time I had left. Spend more time with the kids? Visit these places? Go up and down mountains? We all think think we’re going to do all the things we didn’t do when we didn’t have the time. But I decided I’m going to do something different. I’m not going to wait to be diagnosed with a terminal illness. Instead, every Monday and Thursday, all year round, I do what I was going to do AS IF I had received a terminal diagnosis.”

Here’s a novel thought: What if you invested in yourself first?

I’ve done this by nature for as long as I can remember, but my friend Greg Hartle explained it to me in ways that made more sense as a business owner. I’m paraphrasing, but he said some version of this…


“Invest your money in your own projects because unlike stocks, bonds, and other standard investments, you can usually enjoy 100% of the returns (or more!)”


This mindset of investing in myself has drastically shifted my thinking, especially when I start to evaluate taking on a new project. Yes, new projects are shiny and fun and give you all kinds of dopamine responses, but they also come with pressure, stress, and a whole heap of work. Work that you aren’t sure will pay off.

Invest in projects that are already working: A Teachery Case Study and Growth Plan

For me, Teachery is one of these projects that I keep investing in and look to as my own long-term investment. If you don’t know, Teachery is an online course software that I co-founded in 2014, and it’s always been a side project.

Recently, however, I’ve started to think about creating more predictable monthly income, and Teachery was the logical place to start (especially when using the “invest in yourself first” mantra).

Here’s how the numbers break down when it comes to investing time and energy (which is another form of currency) into Teachery:

  • Current time spent per week working on Teachery (support/dev): 3-5 hours
  • Current monthly revenue (aka MRR): $6,000 (ish)
  • Current monthly paying customers: 120 (ish)
  • Investment in a second developer to beef up our features: $18,000*
  • Investment in a designer to spice up our look: $3,000
  • Investment of my time: 2-3 additional hours per week

Goal: Increase Teachery monthly recurring revenue (MRR) by 3-4x in the next year

Our investment of time and money into Teachery will be recouped in four months if absolutely nothing changes. But I know things will change, because the money we’re spending is on things our potential customers are asking for (but that we don’t currently offer, so we’re losing their business).

At a 3-4x increase in customers and revenue, we’ll go from $6,000 MRR to $18,000 – $24,000 MRR (or $72,000 annually to $216,000). There isn’t a stock or fund you can put your money in that creates a potential increase of 300%! Plus…

One of the best things about investing a project of your own (like Teachery) is that no one can pull it out from under you.

You own it. You control it. It’s your playground, and no one can steal your bouncy ball.

Do you have a project that’s already generating revenue that needs some love? Maybe a small investment and some time could propel your business forward?

*The $18,000 was hiring a second developer for six months. We could have done all the work ourselves, but due to our limited time investment, this accelerated our roadmap immensely!

Investing in new and bigger ideas: BuyMyFuture (now BuyOurFuture) Case Study

You may not have a software product like Teachery to invest in, but you may have a big idea that’s nagging at your thoughts day in and day out. I’ve had a few of these over the years, but most recently, BuyOurFuture was that project.

The initial idea behind BuyMyFuture was to provide maximum customer value to me for my projects ($1,000 per customer) and maximum “Jason’s projects value” to my customers (pay me once, get all my current AND future stuff).

When I started running the numbers on what it would take to make BuyMyFuture a reality, the expenses racked up. How much, you ask? Just shy of $9,000. That included:

  • Website design and development
  • Promo video
  • Legal fees
  • Promotional items
  • Software (podcast hosting, website hosting, etc)

Even though that $9,000 was a scary number to spend, I knew it would be an investment of my own idea that I’d get 100% of the returns from.

So, what happened?

  • In the first launch of BuyMyFuture, I made $178,000 in revenue.
  • In the second launch, I made $123,000 in revenue.
  • In the third launch (BuyOurFuture), we made $107,000 in revenue.

That first investment of $9,000 ended up bringing me over $408,000* in just two years. Show me a stock, mutual fund, or any other typical investment that has this type of immediate return.

Now, of course, not all ideas pan out and end up bringing in hundreds of thousands of dollars. I’ve chased after ideas that barely broke even. I’ve had ideas that ended up in the red. But the important way to look at this is that you don’t put all your eggs in one basket (diversify, as they say), and that you are doing things that YOU actually control the outcome (to some degree).

I’ll take investing in my own ideas over investing in ones where I have no control any day of the week.

*I share revenue numbers, because they’re obviously bigger and more awesome. However, the profit numbers are worth sharing for transparency’s sake: total expenses for all three BuyMyFuture launches equal $105,000. Total profit is then $303,000.

The last thing I want to touch on when spending all your money is the idea of voting with your dollars.

This topic has become more and more important to me as I’ve been in the entrepreneurial game longer.

If you’re being completely honest with yourself, do you really want to see more big box stores out in the world? More huge companies that squeeze as much profit out of their employees and products? Or would you rather spend your money supporting world-changing businesses, industry-disrupting entrepreneurs, or maybe just a hand-crafteded brand run by one guy and his family?

Why I have an “Ugmonk Budget” and why you should have a similar budget too.

Jeff Sheldon started a simple apparel company around the same time I started my IWearYourShirt idea in 2008. The idea behind his company, Ugmonk, was to create well-designed and high-quality apparel (instead of contributing to the fast-fashion world that makes things as cheap and mediocre as possible).

Every year since Ugmonk started, I’ve purchased something from Jeff. Whether it was a t-shirt, a mousepad, a Chemex coffee collar, or one of his anniversary sets, I have an annual Ugmonk budget.

(Not only do I spend money on Jeff’s products, sometimes I also create content about them because I want more people to know about it – a la his current Kickstarter for “Gather.”)

As a minimalist, I don’t often need the things Jeff is creating/selling, but I want the Ugmonk brand to continue to exist. I want to do what small part I can to try to ensure Jeff continues to create beautiful, functional, and meticulously crafted goodies. That is why I have an Ugmonk budget* and why I will continue to have one for as long as Jeff is running Ugmonk.

Ask yourself this question: What do you want to see more of in the world? Spend your money on that.

*The best thing about my Ugmonk budget is it’s $200 per year. That may not make a huge impact on Jeff’s bottom line, but it makes a big impact for me to know I’m supporting Jeff on an annual basis.

And of course, let’s not forget charitable giving…

Donating to various charities is something I’ve done since I was running my first business in 2006. Sure, I didn’t have a ton of extra money to donate, but as a small business owner, I knew how much of an impact a small amount of money could make.

I’m not one of those people who likes to brag and share every time I make a donation. Yet it’s an important part of my money-spending mantra to carve out a chunk of change that goes to folks who are doing good in the world.

Investing is great. Building a nest egg is great. But much like supporting businesses (like Ugmonk) with your dollars, it’s important to support the causes you believe in. Much like anything else that has to do with spending money, if you budget for and prioritize charitable giving, it doesn’t have to become an afterthought (or worse, the first expense you cut when money gets tight).

  • Start with a budget of $100 this year.
  • Next year, double it.
  • Then double it again the following year.

In a few years, you’ll be donating thousands, and it will have turned into a positive habit that you can’t live without.

Let’s recap and wrap up these different ways to invest your money.

There’s a lot to chew on here and I love focusing on taking action. Here’s your quick-hit list of what to invest in and where to spend your money:

  1. Get your insurances in order (car and life)
  2. Build up your “oh shit savings” in a separate bank account
  3. Start a travel budget
  4. Create a repetitive joy budget
  5. Figure out if you have a current project you can invest in right away
  6. Look for bigger opportunities to take risks (and see bigger payoffs)
  7. Define your “Ugmonk budget”
  8. Set aside money for charitable giving

It’s my firm belief that we live in a time when you can always make more money. You can always work more. But if you aren’t actually enjoying your life, then what is it all for?

I wanted to touch on long-term investments before putting a pin in this article. I absolutely believe in “safe” long-term investments (like Index Funds, et al). At this moment in time, I don’t have the excess cash that makes sense to put towards long-term investments. It’s absolutely on the list—it’s just not the highest priority for our money-spending strategy (plus, that Whole Life Insurance does count as a long-term investment).

Then again… maybe I’ll never have a boring long-term investment because I’ll always be creating stuff of my own I want to invest in?