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Different Channels / Different Tones

There are a few universal truths about content. One being that LinkedIn is an animal of it’s own. I’ve been consistently posting for two years now, and this summer I have easily 5x’d my engagement.

Historically, this is where we found financial advisors to join Habits, but these days it’s slowly creeping up as the #1 channel where users discover us.

This post was for all of you high earners, who still feel the paycheck to paycheck grind. The point being…you’re not alone. Easily my #1 most engaged post of all time.

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What Content Really Takes

Content is a black box.

I’ve gained 10,000 followers in a few months. I’ve also gained zero for months at a time. I’ve posted skits, Q&As, (live) investor pitches, satire, personal finance hacks, financial modeling tutorials, vulnerable rants, you name it! Many have flopped under 500 views. Others took 1min to record/edit and exploded into millions of views.

Through it all, content has brought me investors, users, advisors, brand deals, even employees. But it’s also brutal. It strains relationships, gets you roasted in comment sections, and sometimes makes you question your sanity.

So, let me break it all down and share what I’d do if I were starting today.

Reddit: The Training Ground

I started on Reddit during COVID. Just posting about whatever I felt like: relationship advice, aliens, the Chicago Bears. No agenda, just genuinely trying to entertain myself.

Oddly enough, it forced me to learn how to write hooks, find communities, and deal with feedback. Nobody cared who I was. They cared about whether my post made them laugh, think, or argue.

That’s still the essence of content.

TikTok: The Sandbox

TikTok was where I really exploded. Banking stories, funny finance skits, “building in public” moments, sales calls, investor pitches…I just threw it all out there. I hit 15k followers in about 12mo of posting 3-4x a week.

And it led to surreal stuff. Like after a wedding rehearsal in Charlotte (I had maybe 7k followers at the time) when a group of finance bros recognized me and bought me round after round at the bar. That’s when it hit me: content reaches further than you think.

Similarly, I’ve done guest lectures, travel the country (and most recently the UK), and wild stuff have opened up just due to 18mo of consistent TikTok posting.

But TikTok also showed me how brutal virality can be. My first multi-million-view post was me roasting my younger self, staying late at the office on Fridays, grinding on PowerPoints with a million edits from bankers reviewing PDFs on their phones. My intent was clear: I was making fun of that old version of me. But viewers didn’t care. They saw me as mocking people who work hard. The comments lit me up.

That’s the reality: once you go viral, it’s not about what you meant…it’s about how it made them feel.

@jack_boudreau_

Replying to @. stay curious #graduation #career #jobs #corporate

On a brighter note, the beautiful part about TikTok is you can make videos like the one above. For perspective, I was not earning a paycheck and living in my buddy’s rental property for a few bucks a month. The video performed well because I was well intentioned, shared a strong message, and was authentic. It didn’t matter that I wasn’t recording from a penthouse overlooking Central Park.

LinkedIn: The Grind

LinkedIn was slow. Two years of posting before it “clicked.” Today, blunt posts, satire, and building-in-public updates are what cut through.

In my eyes, whatever type of content you want to share, there is an audience out there. You just have to find the right channel. For us? LinkedIn was obvious. It is one of the few platforms that (from a compliance perspective) allow financial advisors to post. Also, there are some crazy stats out there like the fact nearly 60% of daily users earn more than six figures.

Hence why, despite a slow start, I’ve continued to post on LinkedIn.

But it hasn’t been smooth. I’ve been trolled, stalked, and copied word-for-word.

One competitor’s CRO literally viewed my profile nine days in a row…then two weeks later, his GTM team started posting my lines VERBATIM on paid Meta ads and on Twitter (sorry, I mean X).

Don’t get me wrong, I was furious at first, but afterwards it reaffirmed that if they’re so desperate for results…there’s gotta be something we’re doing right that they don’t understand.

So content can be more than just viewership, a funnel, or a testing ground for messaging. It can be a huge advantage to understand your competitors or other players in the space.

Instagram: The Fear Test

Instagram was the platform I resisted. I had ~600 followers, mostly people I knew in real life. Posting there felt terrifying. TikTok was strangers. Instagram was childhood friends, old coworkers, extended family.

But I forced myself. My first reel on financial modeling got ~3,500 views. Then coincidentally my next post, the following day hit 150k views.

That’s when I realized: Instagram loves new creators, and momentum compounds fast. Today, I’m closing in on 25k followers. But it’s been a long road, don’t get me wrong.

It’s still my “fear test” platform. Every post is a reminder that everyone from my high school friends to my parents’ friends are watching. And I keep doing it anyway.

So…if you want to post content, I wish there was a simple and easy list of suggestions, but the truth is you gotta put yourself out there.

If I Were Starting From Scratch Today

Here’s what I’d do if I had to start from 0 again:

• Reddit: Start here. It’s anonymous, so you can take risks without burning your name. Learn to write hooks. Find communities. Practice taking punches.

• LinkedIn: Post consistently. Don’t obsess over the algorithm, it changes every few months. Sometimes it rewards satire, sometimes photos, sometimes short-form video. Roll with it.

• Threads vs. Twitter: I’d skip X. It’s bots and noise. Threads will eventually pass it, Meta owns the attention game. I’m not active on either right now, but it’s on my list for 2026 to take more seriously.

• TikTok & Instagram: Still the best for reach, but crowded. The only way to win is authenticity, humor, or unique experiences. Study creators you like. Don’t copy them, reverse-engineer why their videos hit.

Bottom line: don’t overthink. Post, learn, repeat.

Going Forward…

We used to remember eras by inventions. Now we remember them by people. Jobs is the iPhone. Elon is Tesla. Most creators have 10x the following of their companies.

That’s why a social following is borderline a requirement if you’re building anything. Tech cycles come and go. Algorithms shift. AI will have its moment. But personal brands compound.

And yes…content is awkward, cringe, and sometimes toxic. But it works. For example, 95% of Habits users came from social in 2023, 2024, and I bet 2025 is a similar figure.

But our feeds aren’t updates anymore, they’re calculated and organized short forms of entertainment. Think Netflix with scroll. The only certainty is that trends move fast. Jump early, ride the wave, diversify, and keep showing up.

Because platforms die. Personal brands don’t.

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