
From Crash To Thrive - How 2008 Toughened Us Up
It was April 2008, and everything was just as I drew it up.
My wife and I welcomed our first born son John into our family. I really wanted a boy to carry on the family tradition of five “John’s”. My legal name is actually John. When I found out he was a boy, I raised my arms in celebration. Even the doctor said, “Looks like someone wanted a boy!”
We had just moved into our new home. It wasn’t our dream home, but it was a nice upgrade, five minutes from the beautiful Lake Michigan beaches.
After more than a decade of hustle and hard work, our business had reached the coveted Diamond level, which is the top 1% in our company.
Kara quit her teaching job to be a stay-at-home mom.
We thought we had finally arrived.
Everything was working. Everything was perfect… Until it wasn’t.
Come September 2009, every single area of my life crashed. Physically, spiritually, financially, relationally, it all came shattering down.
The 2008 Financial Crash Was Here.
Nothing was safe.
Our business dropped 50% from its high. Our home dropped at least $50,000 in value within six months of buying it. My health crashed - turns out this wonderful home we were so excited to move into was built poorly and full of toxic mold. My incredible relationship with my dream girl suffered. I was not locked into a Church that could help me, nor was I tithing or giving anything charitably.
I know some of you are going through some tough times.
I want to share in today’s issue the steps we took to work through them, survive, and eventually, thrive.
What We Did Financially

The two most important things you can do to build wealth are:
- Live below your means.
- Increase your income.
Not really rocket science to understand. So we went back to the basics. We bought used, reliable, quality cars and kept them for years. I drove around a used Mercedes from 40,000 miles to 140,000 miles and certainly could have afforded new. We rarely ate out at restaurants.We meal-prepped and cooked at home. We didn’t take any vacations that we couldn’t drive to.
Most of our investing was marketing our business. I was 100% focused on increasing our income. Everything we did was focused on generating leads. So we ran ads, joined networking groups, and experimented with different marketing strategies.
We opened up a physical storefront instead of working from home. From 2008 to 2010, I did not invest into anything else. Blinders on, passion on full throttle, and not listening to anyone’s negativity or opinions on what I should be doing with my money. It was a full scale, relentless assault on the marketplace.
Once we had our business generating excess cash flow, we banked it, and then invested it into safe, cash flow producing assets. We converted our prior home into a rental property, bought self-storage, ran stock options, and focused on safe streams of income. I simply did not lose money on any of those things, because they weren’t risky. I would take no chances of losing my principal capital after what happened with my first investment into tech stocks - I had lost $25,000 of the $50,000 I had saved up by age 22 when the dot com bubble burst.
Everything we did was to diversify our income streams, so if 2008-like conditions returned, we would not suffer like before. I wanted to make sure that when the next storm came, and it’s just a matter of time; a matter of when, not if, it came, that we’d be ready with multiple streams of income, and would not be in a position forced to downgrade our lifestyle. All of the strategies we did are in this free guide I’ve shared with you.
This is also the time we hired a tax strategy company to get our taxes as low as humanly possible. I’ll pay my fair share but definitely not more. The tax strategies I shared with you in last week’s newsletter saved me hundreds of thousands of dollars over the past decade. It’s certainly not the most fun thing to learn or do, but it’s probably the highest return on your time you can get.
Finally, we went back to investing into the most important real estate we’ll ever own: Our minds. This was hands down the best decision we could make. I hired a business and financial coach to guide me. Those monthly sessions were critical to develop and hone in my strategies, and to keep me accountable to my plan. Through those sessions I made a bold move and decided to open a new market in Indiana, almost an hour commute one way.
You want to know how to mess up a great plan?
Change it when things get hard.
The first 18 months were very rough, in fact the first brick-and-mortar location I helped open ended up failing. Instead of giving up on the plan and the original vision, I downsized our space and moved into the basement of a gym, converting the hot tub room into a new nutrition coaching office. Eventually I grew an amazing business out of that location, and expanded to many locations across the state.
Not easy, but totally worth it.
What We Did Health-Wise

I was getting sick at least every other month and sometimes literally every week. I’d recover from a cold and then get another one almost immediately. When I went to my doctor, all he told me was that I should “wash my hands more often.
There are times in life when you know deep down that the advice you’re getting is terrible. My instincts told me there was something else going on, but I knew I needed something better.
Luckily, I had a connection to a Functional Health Practitioner, which was a relatively new and alternative way of looking at the core, the root cause of the symptoms. Generally speaking, Western medicine looks at the symptoms and tries to fix those instead of looking at the underlying causes of the distress. My new doc put me on a plan to restore my health, and it really made a difference.
It wasn’t until a couple years ago when I hired a new functional health doctor that we discovered I had a toxic mold exposure back in 2008. She put me on a very aggressive detox plan that has changed my life. I have not been sick in 18 months, which is definitely the longest streak of my life, and of course as I type this I’m on the final stages of a respiratory illness which broke my win streak.
What We Did Spiritually

I was raised by two loving, hard working Christian parents. My Mom was raised on a farm so she drilled me on work ethic. “Many hands make light work”, she’d often say. She also used to say,“Make hay while the sun shines.” And my favorite, because my Mom didn’t cuss much: “Shit or get off the pot.”
In other words, make a decision, kid, and stick with it. My Dad was a professional at an insurance company, raised by a workaholic father, he decided to always be there for us, and left his work in the office.
It was required in my house to go to Church on Sunday. The problem was, it was really fucking boring. The Church was traditional and conservative. So my view on Church was that I went because I was forced to, it was stiff and boring, and I’d stand up and sit down as and when I was told to. When I hit my college days, I was free, so I never attended Church once on my own accord. When I married Kara, I went to her Church and it was much the same. I’d look for any excuse to not go.
But then, life changed.
I kept getting invited to Road to Life. It was modern, with a band, led by a witty, relevant, and driven Pastor, who was also a very successful entrepreneur. I learned that what mattered most was a personal, direct relationship with my Creator. I learned how to tithe and put God first with my money. I’m honestly not sure where I’d be or if I’d even be alive if I hadn’t found it. Some of the things that have happened I wouldn’t have been equipped to deal with.
I’m not here to direct anyone on their spiritual life or religious choices. I’m merely here to tell you what helped me through some very dark times when it seemed there wasn’t much hope. My wealth has multiplied twenty times since we found our Church. I’m a much more empathetic person, and I can guarantee I’d never have started Indestructible Wealth because I would have been busy chasing more money and success.
What We Did Relationship-Wise

I’ll never forget the day. I was sitting down with one of my mentors, Brad Harris, and explained the challenges that some of my team were giving me.
I can’t believe what he said to me.
He said, “Jack, you’re have a relationship problem.”
“Uhm Brad, did you not hear what I said? This person acts like this, this one does this, and then they do that!”
“Yeah Jack, but there’s always one person at the scene of the crime.”
Damn.
That hurt.
But the truth does hurt sometimes, doesn’t it?
So I went to work on building more effective relationships. What I discovered was that those doing business with me felt like I didn’t care about them. Even though that was far from the case, that was their perception.
And in business, perception is everything.
So I went to work on that, and my business started to grow again. I’m sure many would say I have a lot more growth to do in that area, but I’m much farther along.
How To Cultivate Mental Toughness

Do I regret the tough times?
Well actually, I’m grateful for those times. I don’t want to go through them again, but I recognize them for their incredible life lessons. I’m most grateful for the mental toughness I developed.
Mental toughness is defined as “a measure of individual resilience and confidence that may predict success in sport, education, and the workplace”.
I guess that’s great and all, but what I believe it really means is simply the ability to stay positive and hopeful under negative circumstances.
An entrepreneur has to develop mental toughness to get through Stage 1. As a brief reminder, Stage 1 of Entrepreneurship is where you work 10 units but you get 1 unit of pay. I call it the “It’s NOT worth it stage.” (Stage 2 is 10 units of work for 10 units of pay, and Stage 3 is 10 units of work for 100+ units of pay).
If I hadn’t developed mental toughness, I would have quit Indestructible Wealth many months ago. I’ve done over 100 podcasts, 400 Instagram posts, and 20 blogs with not a lot to show for it to be honest. I’ve made so many mistakes I can’t even see straight.
It doesn’t matter though. I can work for five years straight without seeing a reward, because of the strength I developed back in 2008.
I’ll just keep putting out as much value as I possibly can, to the very best of my ability, and just keep trying to get better. I’ll stay positive (oh I’ll have my days, that’s for sure) and hopeful that I’ll catch fire at some point. I always believe success is just around the corner.
And it’s this hope that’s keeping me going.
Many years ago, my Uncle asked each family member to bring their favorite quote to Thanksgiving. This was mine, and to this day, I lean on it when things get tough. It’s by Napoleon Hill, author of the best selling personal development book of all time, “Think & Grow Rich”:
“With every adversity, every failure, every heartbreak, carries with it the seed of an equal or greater benefit”.
It’s not like things have been great for me. Many of my businesses and investments are down. I’m grateful I have so much of my assets in cash flow producing businesses and assets, but at the same time, it is a bit painful to see the ones that aren’t. And it’s likely to persist for most of 2023.
Does this make me a bad investor? Does this make you bad (guessing many are in the same situation)? No, of course not. There is simply no way to grow your businesses and your wealth in a straight upward trajectory. It will have many pullbacks, many head scratching times where you just couldn’t possibly see how you would lose.
And it’s okay.
In 2008, it was not predictable what happened. Even if it was, not many thought it would happen so soon.
What I do know from the past is that eventually I’ll look back on and say I’m grateful for the lessons I learned. It’s only through adversity that I really learn and make changes. I know I’ll get there but in the meantime, I’m locked into simply doing the best that I can.
These are tough times for some, but eventually they’ll be the best of times. When you look back and share your own story of how you got through the tough times, you’ll know it was all worth it.
Thanks For Coming This Far
There isn’t a call to action on this one. If you’re going through some tough times, feel free to share it with me. I’ll be happy to provide my perspective.
And if I never hear from you, never meet you, and you silently consume my content and it makes your life better, well then, it was all worth it.