Update #3: Timing the Entrepreneurial Leap

Whoa! Our band of corporate escape artists just pulled off a growth trick, we grew 25% in one week. We've expanded faster this week than my collection of half-finished side projects. I'd investigate why, but I'm too busy trying not to spill coffee on my 'World's Okayest Entrepreneur' mug. Welcome aboard, new rebels - let's turn this corporate matrix inside out!"

Remember, if this newsletter made you snort-laugh even once (and let's be honest, my dad jokes are practically weaponized), hit that reply button. Yep, there's a real live human on the other end - shocking, I know. It's just me, huddled over my keyboard, fueled by hope and off-brand energy drinks. Don't leave me hanging in this vast digital void. Your responses are like XP for my entrepreneurial journey!

The Elusive "Right Time" to Start Up

Picture this: It's Stampede 2024, and I'm at some swanky corporate shindig in downtown Calgary. The craft beer is flowing like PowerPoint presentations, and everyone's LinkedIn profile is glowing brighter than a rare loot drop.

I bump into Chad McSuitface, a big shot from one of those gleaming glass towers. He's decked out in a $500 cowboy hat that's seen less dirt than a hospital operating room. He's got that look – you know the one – like he's perpetually constipated from holding in all his "brilliant" ideas.

"Greg, my man!" he says, clapping me on the back hard enough to make me spill my overpriced craft beer. "Heard you're thinking of starting that development advisory firm. LandLogic, right?"

I nod, bracing myself for the inevitable "wisdom" headed my way.

Chad leans in, his expression a mix of pity and concern that I've seen more times than I've seen "synergy" in a corporate memo. "Look, I'm in the trenches at BigCorp. I see the numbers. The economy's wobbling. Housing market's tighter than a rodeo cowboy's grip. Smart money's waiting it out. Maybe in a couple of years, but not now."

I left feeling like I'd just been told Santa isn't real... again. This guy had insider knowledge, right? If he was battening down the hatches, shouldn't I?

The Economic Rollercoaster

But then I remembered something. Back in 2015, I attended a real estate conference right here in Calgary. The oil crisis had just hit, and the bottom had dropped out of the condo market…to zero, literally 2000 sales per year downtown to zero...probably less than zero, given all the defaults. The conference hall was full of industry veterans, all singing the same depressing tune: "Kid, you missed it. The 2002 boom, the pre-2008 madness, even the 2011 run-up - that was peak real estate. It'll never be that good again."

I almost dashed out to my hermit cave in the Rockies right then and there. Why bother if the best was behind us?

But I stayed. And you know what? The next few years saw:

• A pivot to selling Calgary condos to Toronto investors, who were experiencing their own real estate frenzy

• The explosion of purpose-built rentals and the graph going “up and to the right” on rental rates

• The rise of remote work reshaping residential demands faster than you can say "Zoom fatigue"

• Calgary's downtown revitalization projects kicking into high gear, breathing new life into our concrete jungle

What were those naysayers smoking? Probably the same stuff as the guys who thought the Flames would win the Stanley Cup every year since '89…sorry fans (I should have said the Leafs every year since ‘67).

Here's the kicker: Nobody gets to decide when the good old days happen. Not for real estate. Not for startups. Not for anything.

Since that gloomy 2015 conference, Calgary's been on a rollercoaster that would make the Stampede midway look like a kiddie ride:

• Tech companies setting up shop faster than you can say "diversification"

• Downtown office-to-residential conversion projects popping up like food trucks at the Stampede

• A surge in interprovincial migration that's making U-Haul consider Calgary its second home

• Interest rates dropping faster than ____ at Stampede (choose your own adventure on that one)

And LandLogic? Well, we're not buying private jets or mansions yet, but we're doing pretty damn well for a company that "shouldn't have started now."

This is what I'm getting at...

The good old days are now.

It's never a bad time to ship your ideas into the world.

The truth is that timing your leap into entrepreneurship is unpredictable. You might hit the jackpot on your first try, or you might face some setbacks. But you know what? At least you're in the game.

As a friend of mine texted me the other day, “Build, Scale, Sell”...( ←she is smarter than me, so I am still trying to figure that one out, but it is motivating).

I’ll just say: Shoot your shot…

Side Note

We had a fantastic discussion with Donada.com this week regarding the potential automation of our daily processes using an AI agent. An AI agent is like a smart program that can sense what's happening around it, make decisions, and take action to get things done on its own. It's basically Clippy's revenge - except this time, it looks like you actually need help with that document. More details will be shared in an upcoming update.

For now, let's commend this individual for his entrepreneurial spirit and his recent positive stance on AI:

Entrepreneurial Influencer of the Week

Meet StripMallGuy, the real estate world's answer to Batman - if Batman traded his cape for a pocket protector and his Batmobile for a used Volvo. With a Twitter following that rivals small countries and a knack for making strip malls sound sexier than beachfront property, he's the hero the commercial real estate world never knew it needed. StripMallGuy proves that you don't need to wear a fancy suit to be a property tycoon - just a healthy obsession with parking lot layouts and an uncanny ability to predict the next big thing in food court cuisine. Who knew that the path to real estate stardom was paved with discount shoe stores and questionable Chinese takeout?

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Epic Social Drop

As a corporate escapee, I've discovered the true magic of DoorDash. Picture this: I'm knee-deep in crafting my weekly newsletter, deadline looming, when hunger strikes. No time to cook or even step outside. A few taps on my phone, and voilà! 30 minutes later, you are knee-deep in KFC! Sure, it's pricey (and my keyboard is doused in grease), but can you put a price on uninterrupted workflow and the freedom to prioritize your passion project? To my friend who's never used a food delivery app - welcome to the world of entrepreneurial fuel!

A Word to Fellow Corporate Escapees

Remember, fellow adventurers, in the game of entrepreneurship, we're all just trying to level up. Some of us might be carrying more XP from our corporate quests, but we're all noobs when it comes to starting something new. So grab your startup sword, equip your shield of resilience, and let's go slay some business dragons (yes, I am a nerd).

Stay awesome and keep grinding,

Greg "Still Waiting for My Startup Cheat Codes" Mills

P.S. If this newsletter made you smile, share it with a friend. If it made you roll your eyes, share it with that one coworker who still uses a flip phone. Spread the joy (or the mild annoyance) - it's all experience points in the end!

P.P.S. If you're reading this, congratulations! You're officially more thorough than 99% of internet users. Your attention to detail is both impressive and slightly concerning. Maybe go touch some grass?