Welcome to Execs And The City, a witty column from the genuine, emotional, and often humorous exploits of coaching executives in Silicon Valley.

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A Personal & Entrepreneurial Reflection On 2022

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The hibernal solstice is once again upon those with the greatest of fortunes to experience and acknowledge its presence. 

Last night in Montana, we endured negative 31-degree mercury. The appropriately named "once-in-a-generation" winter cold front represents the symbolic death and rebirth of the solstice. 

We're at the point of annual introspection and looking forward once again.

Today's article is unique. 

It's the final publication of Execs and the City for 2022. Since we launched in February this year, we have managed to share 48 articles and grow to over 6500 subscribers. More to come in 2023.

Today I share a "state-of-the-union-Esque" format I've borrowed from my days as the CEO of Discover Podium. I'll also include a few personal effects on how I approach the world now.  

I earned notable respect for sharing the interworkings of the business and how I thought about challenges transparently. Perhaps the entrepreneur inside you may value the following musings as well. 

Let's dive in.

 

Weaving Straw Into Gold

What makes 2022 unique is that it wasn't a strategically dialed concerted effort toward success like in prior years. There were no plans. The year revealed itself and transformed from ashes. 

Since Discover Podium's unwinding in late 2021, I needed to detox from 5 years of immutable CEO discipline. Ubiquitous exhaustion is the closest I can get to explaining the sensation of leading a bootstrapped startup through the Pandemic.

I took a product executive (PLG) role with a great friend and former client. A stint in the corporate world and the comfort of a W2 and benefits would be just what the doctor ordered... Ha! 

Unfortunately, the team I joined met an abrupt end in early 2022—as did subsequent staff in a death-by-a-thousand-cuts implosion of poor c-suite management. 

I don't hold any malaise toward the executives at the organization—I cannot stress enough that most people don't understand the pressures that magnify on the shoulders of the CEO, and grace must be our baseline. However, this 'no-hard-feelings' experience is worth mentioning because it triggered a substantial shift in how I view the world and advise career development. 

If the safe play to work for someone else and earn our living isn't safe, what must we do to live the lives we truly want and protect our families? 

You can give your all in your career. Your best years. Your time with family. Your health. Finite resources we consensually trade for money. And in the blink of an eye—get chopped off at the knees and kicked aside. 

Hundreds of thousands have felt this pain through layoffs in 2022. 

For me, the quarter million dollar salary guarantee was gone. But I, fortunately, kept coaching executive clients through all of the turmoil. Maintaining my client rapport eliminated financial fear of what would come in 2022. 

Protip: Diversifying your income and building multiple revenue streams might be the only way to experience financial bliss and drown fear. Making less from several sources is more secure than making a lot from a single high-paying executive job.  

Sure, the coaching business had diminished from the seven-figure glory days of Discover Podium—but the know-how, discipline, and drive to thrive remained. Nothing a little momentum and elbow grease couldn't fix.

Sometimes setbacks are opportunities, especially when your eggs are in multiple baskets.

 

The Great Reset—Now What?

I mentioned that I didn't have strategic foresight for 2022. But it wasn't intentional; I planned on being employed! So my untimely termination—or dumb luck—turned out to be a blessing. 

I didn't have any goals or expectations that needed resetting. I only needed to support my family and have faith. I did, however, strongly reconsider what success meant to me.

I used to think it was hockey-stick growth, VC backing, public approval, and the collective support of a community rallying behind a vision you were passionate about achieving. 

We had glimpses of that success at Discover Podium, which felt intoxicating. I won't conceal that "founder's high" feeling. It's very real, but I believe it happens when it's supposed to and not a "fix" that you should chase.

Now I feel that if your goal is some fabled unicorn tech success, you're probably an addict or moron—or at least grinding away for the wrong reasons. I proactively accept your criticisms of hypocrisy—and voluntarily plead guilty as a recovering ego-driven Silicon Valley founder. 

No. I've decided that sort of success isn't for me. Not this time, muchacho! 2022 has been a great reset. 

I approached this year actively avoiding building a business that would require raising capital—actively avoiding hiring staff—actively avoiding equity and stock and exit strategies and P&Ls—actively avoiding doing things that grow and scale. It was a year of actively avoiding nearly every business strategy pummeled into my fellow Silicon Valley executives and me. 

Instead, I focused on working less and enjoying more. How romantic.

Living my life, as it were—but still stoking the flames of excitement that flood me when I help someone overcome a period of immense expectations and challenge. 

Many executives reading this will relate to the enormous pressures they experience daily. Add on being forced out of work, and you have the recipe for an authentic soul-searching adventure. That's the good stuff, and those conversations fuel my work.

I took the following notable actions in 2022. 

I... 

  • Restructured my life priorities. 
  • Took days off between hectic client work; and a month off at once.
  • Cooked and ate more meals with my family. 
  • Walked my dogs. 
  • Traveled the country.
  • Transformed consumerism to essentialism and lived more frugally. 
  • Admired, supported, and observed the transformation of my pregnant wife. (What an Earth-tilting experience, by the way).
  • Stopped drinking alcohol. (355 days and counting) (Cutting added sugar is next)
  • Journaled (through the blog). 
  • Began coaching solopreneurs and small businesses.
  • Started multiple revenue streams to ease stress and diversify my financial independence.
  • Entertained partnerships I'd previously avoided. 
  • Launched CORE Connect.
  • Invested in self-learning, primarily via book summaries and YouTube.
  • Studied and applied financial strategy. 
  • Prayed (much) more and grew in faith.
  • Practiced more gratitude and grace.
  • Learned how to eat healthy (again). 
  • Prepared to be a father.
  • Focused on being a more attentive and reliable friend.
  • Went outside to golf—a lot. 
  • Slept through the alarm when my body needed rest.
  • Broke the boundaries of client relationships to make a more meaningful impact in their lives.
  • Turned my phone off. Stripped down the stranglehold of toxic politics and media.

And the results on my business, life, and relationships were notably better—more rewarding, more satisfying, and more intentional. 

How could that be? And what are the dollars and cents of it all?

In short, I was less anal about business objectives and forcing success. 

Again, contrarian to the KPI OKR QUARTERLY REPORT-driven world we lead as executives. 

Sure, I made certain I could pay the mortgage and support my family. The physiological and safety needs for survival always hold firm as the foundation of Maslow's Hierarchy of Needs.  

Still, I didn't arbitrarily point to another successful business and base my happiness—or self-actualization—on doing better than them. Comparison is the thief of joy.

In 2022—I didn't need to see 25% MoM growth or investor attention—or more PR accolades. I needed to build a life where I could see my kids grow. I needed to create the conditions where I could become a great father. I needed to be the husband my wife could lean on during her first pregnancy. If all of that is out of sorts—what's the point? 

That's a key for me—and maybe you too. 

I want to be clear that I am not bashing high-performance leaders, their methods, or their teams. There is a time and context when you must lead with steadfast discipline and hyper-concentration on driving business metrics. 

2022 was a different time for me. And that's okay.

 

2022 By The Numbers

Being that I can't quite shake my wretched Silicon Valley scoundrel core, I did evaluate the business metrics. I may be youthfully naive and inspired by an idyllic Millennial lifestyle, but I've yet to go entirely mental. 

I simply didn't tackle the ThinkWarwick P&L until roughly six weeks ago. And I actually love working on P&L. Talk about a year of lollygagging. 

I had been curious about the business performance but afraid to look because I spent the year taking action and experimenting more than paying attention. So I was surprised at what I found. 

ThinkWarwick managed approximately 1/3 of what Discover Podium made in its best year. When presented like that, it sounds like a significant step backward. 

However, let's look deeper.

Staffing Requirements

TW: 1 

DiscoPod: 20+

Revenue Sources

TW: 7 

DiscoPod: 2

Weekly Hours Worked

TW: ~30/wk 

DiscoPod: ~80/wk; 100+ during the Pandemic.

Clients Supported (Impact)

TW: 185/yr

DiscoPod: 522/yr

Now you may look at that data and say, "Jacob, you must be a shit manager to get those results with so much staffing support." —and there may be some truth to that; however, I've found that there is always so much more than meets the eye when you dissect the impact of a business. And what success really means to you.

And for me, 2022 was the most fulfilling and successful year to date. Though 2023 may mean creeping back to those performance goals and paying more attention to growth as the foundation of ThinkWarwick continues to gain momentum. But let's leave that to January.

Thanks for reading and sharing Execs and the City this year. Here's to eliminating any 2022 ruts that you're in—and creating fresh tracks in 2023! See you soon.

Want to speak directly with me about your career? Contact me below.

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