Hello Dear Friend,
Welcome to the Sunday edition of the Things I Wish I Knew Earlier (TIWIKE) Newsletter!
Don’t get me wrong, every choice matters.
It’s unclear how the effects of even our littlest decisions ripple out into the future. But if we could run an 80/20 analysis on the long-term impact of our choices, we would see that the 20% of our actions accounting for 80% of the effects comes down to a small handful of choices to either go one way or the other. You know, those proverbial fork-in-the-road moments when you have to choose either to go right to march off toward one destiny or hang a left toward a different one entirely.
These are the ones you can’t reverse, or, if you can, it’ll take so much time and effort that the decision to double back becomes another life-altering decision.
In the summer of 2019, I faced one of those scenarios.
I want to tell you that story to share what it taught me about how to evaluate my relationship to risk as an aspiring entrepreneur.
TIWIKE #1: We take risks, then we die
I usually hate unsolicited advice.
But in July of 2019, I was the one seeking out counsel, just not from the person who gave it to me. I had to make a huge decision quickly and felt conflicted. A couple of months before that, I met someone who wanted to become my business partner.
As far as I could tell, his skillset meshed with mine wonderfully.
He was an expert in the investment side of the real estate industry, and I was an expert on the primary market.
Our idea was to build a real estate team to serve both kinds of customers, including clients looking to buy and sell their home and clients looking to buy and sell investment properties. But I didn’t know this guy. Here we were contemplating tying our futures together in a manner that felt eerily like marriage, meanwhile we had met less than 60 days prior.
In the face of these sorts of crossroads, I like to search for different perspectives by getting advice from lots of people I admire.
So there I was in a restaurant with two of my closest confidants, ready to lay it all out for them, and in walks some guy I didn’t know.
Apparently my friends invited him without telling me. I was initially irritated but the more I got to know him, the more I warmed to him. He didn’t say much anyway. He just sat back and listened.
So I laid the entire situation out for them.
The pros, the cons, the aspects that were unclear, and the parts that made me uncomfortable.
When I got done, my friends gave me their thoughts. I made some notes. We ate some good food. And then we began gathering our things to conclude the meeting.
Just as we were getting up, the fellow who joined us spoke up to say something I would never forget.
He said, “You didn’t ask me for advice, but I’m going to give it to you anyway.
I’m an engineer. I like my job and make a good living. I have a beautiful wife and two sons who also have good jobs and families. But my parents were middle class. They raised me to be middle class, and that’s what I am.
I raised my boys to be middle class, too, and that’s what they are.
To be clear, there is nothing wrong with being middle class.
But now I’m 57 years old and set in my ways.
So here is my best advice: take more risks. Give yourself a chance to climb up the socio-economic hierarchy. You don’t get to do that without taking big risks. And here’s the thing I didn’t know as a young man–guys like you, talented and hard-working, will be fine by the time you get to my age regardless of what happens.
You can make massive mistakes and endure what feel like unovercomeable setbacks and put it all together again.
You are stronger than you think.
Besides, we just take risks, then we die, right? So what do you really have to lose?”
I was stunned to silence.
I knew immediately he was right.
I left there, called my potential partner, and committed to going all in. That set in motion a series of events that led to filming and launching a national television show, an experience I never could have secured without that partner. Then it led to discovering my life’s work.
We take risks, then we die.
What a morbid yet profound insight.
TIWIKE #2: The downside isn’t as bad as you think
Fast forward more than five years to the present day.
The results of most decisions will reveal themselves over that timeline. Like all choices, my decision to partner with that person had both good and bad ramifications. We started our team to service both primary and investment clients, called the Apollo Property Group. Over the course of our three-year partnership, here are some notable achievements:
- 300+ closed transactions (the average agent closes five per year)
- $80,000,000+ in closed transaction volume (the average agent never reaches $10,000,000 in their whole career!)
- 13 sales agents, at our largest
- The creation of a real estate investment firm where we renovated 150+ homes, a sister company to APG
The story culminated in our selection to film and launch the first real-estate-based national television show ever produced in Alabama, Flipping Down South on A&E Network, which is an experience I’ll never forget.
We went through multiple rounds of interviews. The network told us they had reached out to 1000+ companies across the nation, NDA’d 500, and ultimately selected three to star in a show of their own, one of which was our company. Two months after our final interview, multiple film crews descended on our downtown Birmingham office like a tornado.
For four months, we filmed multiple days per week.
Toward the end, I was personally filming more than 30 hours per week, which was completely separate from my normal duties running the companies.
It was brutal and illuminating. Pulling back the curtain on the TV business taught me a lot about the entertainment industry. We wrapped filming in August of 2021, then launched the show in March of 2022.
In May of that same year, just two months after launch, my partner and I concluded our business relationship and parted ways.
We had different visions for the companies and different strategies for dealing with the responsibilities we had taken on together.
Nothing like the weight of a national TV show to expose the cracks in your enterprise. It took fully two and a half years, which takes us to the present day, to disentangle from one another. Full business partnerships are like marriages from a legal perspective. And it got ugly, like it usually does.
Over the duration of time between our decision to part ways and today, I have endured pretty much every kind of emotional and financial hardship that stems from this sort of thing.
The journey has been dark and challenging.
There were times when I didn’t think I was going to make it. Yet here I stand, stronger than ever, and that’s the point here. I remember looking around at my life when I was at the lowest point and realizing…I was fine. Sure, things were stressful. Far less than ideal. But my bills were paid. My marriage was good. My health was in order. We had food on the table. I was fine.
And that is the dirty little secret.
Death is the only permanent setback.
You are stronger than you know. And however horrible you think the worst-case scenario is, it isn’t as bad as you think. Not because the experience of it is better than you expect but because you can endure far, far more than you think.
It is easy to not take the risk when you obsessively focus on the potential downside of a decision.
But that is keeping you from ever feeling the warm light of the upside.
It is keeping you from living out the glorious destiny you are designed for. It is keeping you from rising up the socio-economic ladder, like my friend said. Humans weren’t put on Earth to live in fear. We were put here to go for it, give it our all, leave all our blood, sweat, and tears on the battle field of life, and take risks.
The downside isn’t as bad as you think.
TIWIKE #3: The upside could be greater than your wildest dreams
The upside deserves the attention you are giving the downside.
Most choices don’t have huge upside or downside, but every now and then you find yourself staring down a split in the road where the destination of one is as far away from the destination of the other as you can imagine. I think that’s the whole idea behind Heaven and Hell, imagistic representations of the very best and very worst possible destinations.
Here I am five years later.
I learned a tremendous amount from the entire experience.
I learned about investment real estate, leadership, relationship management, the TV business, the power (for both good and bad) of partnership, among many other things. But the most important lesson involved the sort of business I want to build, which had lots to do with the sort of life I want to lead. Up to the Apollo era, I thought the pathway to my life’s work was by building up a business, hiring in a team to run it, stepping out to receive lots of passive revenue, and THEN beginning the real work of my life.
But that is not the way, at least for me.
I dismantled the sales team at the end of December, 2022, to focus on two primary projects:
- Jump starting my personal sales business, which had taken a backseat to building Apollo, with as few expenses and few responsibilities as possible. After learning about every crevice of the real estate industry, helping my friends and family buy and sell real estate was really easy for me, and fun, too.
- With responsibilities taken down to the most manageable level, I reclaimed a substantial amount of time, which I dedicated to learning about my next venture, which I wanted to be my life’s work rather than something I needed to finish before beginning my life’s work.
Now here we are kicking off December of 2024, a full two years after dismantling the sales team and beginning this most recent leg of the journey.
My sales business is thriving, with 2024 being one of my best years an agent (despite it being a terrible year for the industry).
And I am on the back-end of 18 months worth of research and development to discover my life’s work. My biggest dream has always been to run a business (or portfolio of businesses) that (1) I love to run so much that I spring out of bed each morning to attack the day, (2) changes the world for the better through the problems it solves and the increasingly large amount of profit it generates (which can be invested into world-changing initiatives), and (3) is structured for exponential growth, which means it grows at an accelerating rate over time.
The biggest upside of the risk I decided to take in 2019 is that it led directly to the discovery of my life’s work, which I have been in search of for 15 years.
I have summed it up in what I call my Life’s Work Statement, which goes like this:
My life’s work is to make the dream of full-time, world-changing entrepreneurship accessible to anyone willing to put in the effort, by educating, inspiring, and connecting aspiring founders to discover their life’s work and transform the world with it.
I plan to pursue this life’s work in two primary ways:
- The creation of Bad Plan Academy, an online academy for aspiring founders who dream of full-time, world-changing entrepreneurship like me.
- The launch of the Cody J. Cummings Show, a daily live show exploring human flourishing, where I plan to share stories, frameworks, and lessons I learn, as well as interview people I admire, with an ever-growing audience.
I am in the final stages of building the foundation of both of these pursuits and plan to launch them in tandem in the beginning of this coming February.
I will of course continue helping family and friends buy and sell real estate.
This is my dream business and passion project, work I am perfectly suited to do. And since it will operate online, I will be just a viral post or two from the exponential growth I desire. The upside of the decision to partner in 2019 and the decision to launch these two projects in 2025 could very well be greater than my wildest dreams. But I don’t know…I have some pretty outrageous dreams.
We will know more in five years, so stand by.
Thank you so much for being part of this journey with me. It is a true honor that you read this newsletter every week. I am laser focused on bringing far, far more value to you in the coming year, so stick around.
If you are facing one of these fork-in-the road decisions right now, my advice is to trust your gut, to deeply consider the upside, to solicit counsel from lots of people you admire, and to bet on yourself. After all, if you won’t bet on yourself, why would anyone else?
The upside could be greater than your wildest dreams.
Question of the Week
What risks are you currently avoiding that could potentially have massive upside?