“We think no more of Inco on a Sudbury Saturday night.” – Stompin’ Tom Connors
For much of his career at the Canadian Broadcasting Corporation, Jay Legere moonlighted as a YouTuber. Tapping into his love of the outdoors, Legere’s channel is a mix of camping, cooking, and construction at various cabins he leases in Canada’s remote Northwest Territories. Authentically humble and with an endearing ability to laugh at his own many mistakes, Legere steadily built a loyal audience—us included.
After surpassing 200,000 subscribers in mid-2024, Legere posted a video titled “Quitting My 20-Year Career for YouTube.” For any would-be entrepreneur who aspires to walk a similar path, the opening three minutes of that video are among the most inspirational you’ll find on the internet:
“When I resigned, I told my boss I just need to see what I’m made of. I’m a newsman. I make news every single day. I’ve been making news for over 20 years. Whether it be as a videographer, reporter, video journalist, producer, radio producer, video producer—you name it, I’ve been doing it and I’ve been doing it in the news world. And I’ve had the same employer for 19 years and every day I go in and make sure that deadlines are met, people are on track, scripts are accurate, scripts are factual, we meet requirements, and journalistic standards. It’s been a long time. A long time, doing that.
And I’ve decided I’ve had enough of the same thing, the same 9-to-5 news-making job. It’s been a long time. While I’ve had many ups and downs, I don’t dream about it. I dream about YouTube. I’ve been dreaming about YouTube for a very, very long time—six, seven years now. I dream of being my own boss. I dream of making videos, I dream of challenging myself, I dream of going into the woods, I dream of doing something totally scary and terrifying. In the middle of the night, when I wake up, I think about my next video, I think about camera gear—I love camera gear. I think about going into the woods, I think about doing silly videos, I think about doing solid videos, I think about doing cinematic videos, I think about doing fast-paced videos, I think about changing things up all the time.
And I think, giving it all up—giving up a full career. I have a senior job, right? I’ve climbed the ladder, and I’m giving it up for something that might not make sense whatsoever in the long run. It might be the stupidest thing I ever do—but I gotta try. I have to try, and I can’t achieve the things I want to achieve when I have a Monday-to-Friday, 9-to-5-job career. I’ve achieved everything there that I’ve wanted to achieve. Like I said, I’ve climbed the ladder. I’ve gotten to the top, and I put in a lot of hard work. And I think to myself, imagine if I put those 9-to-5 hours into YouTube.”
Imagine, indeed.
By any measure, Legere’s gambit has been a smashing success. He is posting more often and with higher quality, investing heavily in his channel, and presumably having the time of his life doing it. Since quitting, Legere has grown his subscriber base by over 50%. More importantly, according to the social media tracking site Social Blade, his monthly views have more than doubled on a 12-month rolling average basis. The real risk facing Legere on the day he quit was staying, not leaving.
Legere’s success was all but guaranteed for one powerful and overriding reason: he traded spending his time on things he felt he had to do for things he feels he gets to do. When a talented person has the courage to make such a transition, the sky is truly the limit. Productivity soars, work becomes play, and money almost always takes care of itself. It is staggering how much can get done with no meaningless meetings clogging up your calendar. We call this the “have to/get to” ratio internally, and driving that number to zero is one of the greatest life hacks imaginable.
Perhaps just as importantly, Legere is well on his way to effectively making the transition from labor to capital—the value he creates with his own hands and mind now accrues directly to him and his family. As his channel scales, each hour of work becomes more lucrative. He captures the value of the improvements he makes to his properties while filming, and sponsorships become more profitable as his reach continues to grow. If he isn’t already earning more than his prior salary, it surely won’t be long before he does, and by a wide margin.
The virtuous cycle of compounding your own capital while pursuing only get-to-do activities is an unstoppable force, one we have experienced together as a team over the past four years.
For Doomberg’s co-founder and editor-in-chief, “outdoors in the winter woods” is a quiet room packed with books, preferably written long before everyone was glued to a mobile device. A fierce mother and devotee to the art of craft created with distinctly human brilliance, she could easily get by with a landline phone, proper stationery, and a pantry filled only with ingredients—“packaged food” is an oxymoronic phrase in her kitchen. Her idea of a vacation looks more like walking the Camino with her husband and boys than a week in a big hotel with a nice pool.
To her, the ongoing artificial intelligence boom is an unsettling and unwelcome development, one that only makes it harder to connect with the human spirit. When a large language model (LLM) can spit out the Cliff Notes to all the greatest literature in a matter of seconds, to say nothing of the new “literature” being produced by the same means, the reader is robbed of the get-to-do activity of immersing in the story itself—as the author surely intended.
On September 1, under the nom de voix of Ruby Love, the same Doomberg team that has published more than 400 articles on energy, finance, and geopolitics launched its sister publication—Classics Read Aloud. The name is rather self-explanatory, but here’s a bit more detail on what this new project will entail, from the “About” page:
“Classics Read Aloud is a project of pure joy. As an avid reader in my youth, I lost touch with the practice in my early adult career-building days, and reconnected with it as our family transitioned to homeschooling. There is no downside to spending time in great literature. With a book in hand, no line is too long, no waiting room visit too taxing, no nightly routine left unrestful.
Being read to can be a particularly tranquil way to connect with the stories held between the pages. I hope Classics Read Aloud encourages you to tuck away distractions, get cozy, and be transported.”
Classics Read Aloud will receive the same commitment to excellence, attention to detail, and consistency that we hope have become hallmarks of the Doomberg project. While we recognize that the underlying subject matters are worlds apart, they are not mutually exclusive—many who appreciate authentic analysis politely expressed undoubtedly love a good story well told. If you find yourself in that category—or know someone who is—please subscribe or forward this piece to someone who might.
In her most recent dispatch, Ruby Love reads the iconic Ernest Hemingway’s short story “Big Two-Hearted River.” It is a tale of trout fishing alone in Michigan’s Upper Peninsula, conversing with Mother Nature, and the sustaining invigoration that comes from being isolated in the woods. Jay Legere is, of course, merely walking in the shoes of Nick Adams, and no LLM can ever replace Hemingway’s writing of it—or, dare we say, Ruby Love’s reading of it.
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Doomberg. I just finished a 37 day Camiño de Santiago Frances. I didn’t do it to show anyone including myself or teach anyone a lesson including myself. I did it to find the Holy Grail. Inner Peace. Walking through the Maseta by myself for 220 kms was something out of this world. Listening to my thoughts and watching my responses from outside of myself brought that peace. 45 Celsius for 10 days was a turning point. The FN Camiño is not going to walk itself. Every day no matter what.
Thank you for your penmanship.
In an age of instant summaries and TL;DR culture, we're losing the magic of discovery that unfolds through reading books. As a parent, I made my share of mistakes, but one choice I got right was reading to my kids every night I was home. From bedtime stories to epic novels, we shared those moments until they left for college—and we're all richer for it. AI's rise is unstoppable, but we still wield free will. We can choose to carve out time for the slow, irreplaceable joy of turning pages together....Thank you Doomberg