As a companion piece to my last article, on anxiety and masculinity, this is a guest post by a coaching client of mine: .
At the top of my game
It was 2014, and I was working in e-commerce for one of the largest retailers in the world. I was at the top of my game but also working 100 hours a week. People often chuckle about how I could work that much. Think 7 days a week onsite, 13-hour days and phone calls daily or nightly, depending on when I was home. The business lost $30k a day when I wasn’t present — close to $1m a month. I knew how valuable I was to the operation; I was also expected always to be there or to answer the phone when I wasn’t. I worked 112 days with only two days off in between.
At that time, I knew I was in the top 1-5% of operators, beating Ivy League MBAs, and getting promoted every 9 months on a waiver program. I began to realize I should work for myself and capture that ROI for myself, a business, and my family.
I read Rich Dad, Poor Dad that year, and I knew that was it. I would need to build, buy, or invest into something that I could pour my energy into that would provide an income and lifestyle that would support my growing family of 5 (now 8). The real goal was acquiring multiple companies or assets in a holding company.
Over the next 6 years, I would experiment with side hustles, startups, and franchises —until in 2020 I acquired a trucking company with a partner. The goal was to grow the business to where both of us would be full time, then take profits and buy real estate. During 2020-22, Covid made times good. Freight rates were amazing, and profits were reinvested into real estate. The plan was working, and I finally felt like I was hitting my stride. In spite of losing my job where I was working full time, I had a backup income and money in the bank.
“The Lord gave, and the Lord hath taken away”
By the end of 2022, the freight market was turning. We quickly pivoted ahead of the market and put ourselves in a “safe place”. Behind the scenes, I had a manager who wasn’t performing, and I didn’t realize that we were actually losing $10-20k a month, only being held afloat because of the sale of trucks, which was making the financials funky.
By mid-2023, I lost my job for the third time in 3 years, and the logistics industry was in full tailspin. I decided to fire the manager and take the business on full-time. At this point, I didn’t know we were haemorrhaging money monthly. Within 3 weeks, I realized we were in trouble and quit taking a paycheque. My mission: save the business from bankruptcy and my life savings with it.
Now mind you, this is from the highs 8-9 months before when things were rolling. From making maybe $400-500k per year to now making zero AND at risk of losing my house and everything. $1.1m of debt on the business meant I was underwater in a big way. I would wake up every night at 2am and think about ways to solve it and have near anxiety attacks. Depression and anxiety I fought every hour. Once VP of Operations, leading 3k people….now on the brink of failure. The negative stories in my head were real.
At the lowest point, my partner and I went to our accountant to see what he could advise. After 15 minutes, he just stared at us and said, “I’m sorry, guys, you're going to have to shut this down. You probably have 45 days before you can’t make payroll.”
The Cross
I embraced the Cross and prayed every day. Every hour, I would do the next profitable thing. I removed every expense from the budget. I quit paying for tire repairs and bought semi-truck tires then installed them myself. I told everyone that we owed to put me on 6-month terms. I blew up credit cards to pay off loans to improve cash flow. I started consulting on the side. I tried to start a tire-repair business, only to sell it 6 months later. I fought for a free month on a lease payment here and a line of credit over there. I had our largest vendor, that was overcharging us, put on stop payment until they credited us $10k. During the delay, I was able to pay off other bills. Meanwhile, they were threatening to seize our trucks.
Fast forward 9 months, after being laid off from another company, the trucking company still survives. We’ve endured so much and recently cashflow just got worse from a bad insurance renewal where our rates increased 75%. We’ve had incredibly bad luck the past 2 years.
I often wondered if my business was cursed. Regardless of the source, God’s allowed it for my good.
Today, I’m working on consulting on the side. I fired my last manager, and I’m taking on 80% of the workload except for some part-timers. Looks like we’ll have to file Chapter 11 and restructure debt to survive. I’ve successfully whittled down $800k in personal guaranteed loans to $250k, and I’m making $10k ground every month.
Reflecting on the past 4 years has been a humbling experience. I feel fortunate that I’ve been able to absorb 4 job losses with minimal impact on the family. I often think about what I did wrong, and how I’ll do it differently next time. I think that’s important and should be done often.
The first virtue of leadership
However, the more I contemplate the difference between what we perceive as successful vs. unsuccessful, I realise it’s often only God's will. I asked him in prayer recently, “Why No? What did I do wrong? Why couldn’t You allow this?”
We must value our gain in virtue not the value of financial freedom or security. I’ve found virtue in fortitude, courage, and peace with trustful surrender. The first virtue of leadership is obedience, and that starts with the Creator.
Each person has a different level of risk and self-preservation, and many people don’t take risks and start businesses because of my story above. But if I had to do it over again, I would. Why? I’m a better Christian man, husband, and father despite the financial hardships. How? Here are some key takeaways:
Courage - It’s a muscle that needs to be built. If you never test yourself, you’ll become weak. I’m not suggesting leveraging your house like I did; however, taking risks and betting on yourself builds confidence.
Confidence - It motivates me to help others and to continue to fight every hour of the day. It also attracts others. My kids now know that the path to virtue is through daily struggles and hardships. We’re blessed despite our hardships, and they’re welcomed, not avoided.
Obedience - Ultimately, I’m obedient to the Father and His calling for me. I trust that His plan for me is better than mine; therefore, I surrender all the outcomes and obediently show up every day.
Fortitude - When starting on a journey to improve one's position, 99% of the time, you’ll have to give more than even before to get to somewhere you’ve never been before. Doesn’t matter if it’s financially, running a marathon, or learning a new trade/skill. Fortitude is the only answer: iron sharpens iron. Fortitude is simple: you simply don’t quit.
Last but not least, hire a good finance person to double-check your work. I will never make that mistake again.
“As it hath pleased the Lord so is it done: blessed be the name of the Lord.”
I’m a completely different man than I was 12 months ago. I’ve been able to help so many other owners as well. The stripes I’m earning are for heaven and with my family — not zeros in my checking account.
It’s been clear to me that no matter how good I am — how smart my decisions, how well I time the market, the industry, how lucky I get, how good the team I hire is, how well I invest — God holds the cards.
So it’s futile, then? No, that’s the beauty. The outcome’s just not that damn important, it’s just a crucible to find who He’s called you to be.
“Blessed be thy Lord.”
This person’s first mistake was reading ‘Rich Dad Poor Dad’. Kiyosaki’s advice about getting into as much debt as possible is terrible 🤦🏻♂️
Sorry Knowland, but I’m going to side with Benedict XIV here…
Who says: “One cannot condone the sin of usury by arguing that the gain is not great or excessive, but rather moderate or small; neither can it be condoned by arguing that the borrower is rich; nor even by arguing that the money borrowed is not left idle, but is spent usefully, either to increase one’s fortune, to purchase new estates, or to engage in business transactions.”
And I’ll leave you with this quote by Pope Clement V…
Who says: “Anyone who argues that interest isn’t sinful is a heretic”.