If you enjoy this letter you can watch it in more depth ​over on YouTube​.

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Every year there are countless videos promising that “This is the best time in history to start YouTube”.

But while each provides a unique take on that same idea, in one way or another they’re all trying to convince you why you’ll absolutely succeed if you start this year.

And sure, maybe they’re right. Many of you will.

But what if I told you the real value isn’t in that promised success at all? That you can still win at YouTube even if your videos and channel fail.

Now I DO believe this year IS the perfect time to start your channel. I’ve seen the same videos as you that appeal to both our ambition and our emotions.

• That content is a great investment in the future.

• That you can earn money on the side.

• That you can meet people who care about the same stuff as you.

• That its a creative outlet.

• That it gives you an excuse to work on the thing you’re passionate about.

Those are all true. But I have a feeling many of you who have seen these videos are still searching for a different reason that will convince you to finally accept the risk, that will silence all of the “what if’s”, and that will finally push you to take the leap.

After twenty years working as a creative - all the way back as a self-taught freelance designer at 15 years old to now leading projects with millions of dollars on the line as a creative director today - I've learned a lot about success and failure at every scale.

But unlike all the traditional videos on this topic, I don’t want to talk about what success looks like - I want to focus on the failures.

Because its not that we can’t recognize the benefits if we succeed on YouTube. We can all see the upside of that outcome. What’s been missing from the conversation is that no one talks about the incredible amount of value that you can still tap into no matter how your videos or channel perform.

Which is why in today’s letter I want to introduce you to three reasons why starting your YouTube and creator business this year is an excellent idea — especially if it fails at the start.

Collect Your Dots

Now I know this sounds a bit counter-intuitive so let’s kick off the first reason with a familiar idea from Steve Jobs. We all know him for his incredible successes, and entrepreneurs and creatives love dissecting his path to “find the formula”.

But one of his most powerful insights wasn't about success - it was about uncertainty and I think it can best be summed up by a quote from his 2005 Stanford University commencement speech where he said:

“You can't connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well-worn path, and that will make all the difference.”

The example he then follows this with was when he dropped out of college after just one semester due to financial reasons. He felt the required courses weren’t valuable enough to justify his parents life savings.

But instead of leaving education entirely he stuck around on campus and audited courses that interested him, specifically calligraphy classes. It was in those courses he learned about typefaces, letter spacing, and what makes typography beautiful.

He admits he had no practical use for it at the time.

But ten years later, that specific knowledge helped Apple revolutionize personal computing when the Macintosh became the first computer with beautiful typography. Something we now take for granted on every device.

I always liked and found comfort in this idea that random or unrelated experiences can end up being crucial to future success and opportunities, and that you can only see the connections in retrospect.

But it wasn't until I was listening to a podcast a few weeks ago with Dharmesh Shah, the co-founder of HubSpot, which is currently valuated at 37 Billion, that I finally realized how to make this idea less of a comforting truth reminding me to trust the process, and more of an actionable insight that I could make use of proactively.

What Dharmesh said was that as entrepreneurs we have to think of ourselves as dot collectors. And that collecting dots could be anything from the skills you learn to experiences to people you meet.

Its a very subtle shift of the same metaphor but that simple reframing of the concept completely changed my life as a creator because what was once more of an emotional comfort, now felt like a tangible, practical strategy.

By approaching YouTube, as a creator entrepreneur with a dot collector mindset, you can more clearly see how every video builds value - whether your channel takes off or not. Even a channel that gets just a few hundred views per video, picks up a couple dozen subscribers, or only convinces one person to join your newsletter.

As a creator you're learning to write stories that hook attention while you develop scripts and analyze retention.

You're learning packaging and persuasion as you craft titles, thumbnails, descriptions and calls to action.

You're experimenting with positioning and how to call someone to action when converting casual viewers into subscribers.

And through all of that, you're building the evergreen skills that will give you leverage no matter what you create next because you’ll know 1) how to command and hold attention, 2) how to build genuine trust with an audience, 3) how to shape an offer that resonates, and 4) how to exchange real value.

And from fine artists to investors, these are the fundamental skills that will drive success - whether that's in two months or two decades.

The Power of Imperfect

This brings us to the second reason. Most of us who decide to start our creator journey on YouTube want to do everything in our power to ensure our first video will be a huge success.

But while I don’t want to dissuade that level of effort, I’d argue that if you were to somehow pull that off, that that very same early success might actually rob you of your most valuable future asset.

I was recently listening to a podcast interview with Amjad, the founder of Repl.it, one of the hottest unicorns in Silicon Valley right now.

As he broke down his background and the decisions that brought him to where he is today, he reflected that whenever he had to make a choice or was at a fork in the road he would just ask himself: "What will make the best story?"

Even the choices that led to temporary setbacks or failures, he still sees as the right call and given the chance, he would make the same decisions despite knowing they led to failure at the time.

Donald Miller shares a similar philosophy in his book "A Million Miles in a Thousand Years" where he talks about viewing life as a story you're actively shaping.

Whenever you're faced with a fork in the road, he urges you to choose the option that will make for a more meaningful narrative.

Emotionally, I think this is a beautiful lens to see life through.

But as creators the reason this is valuable for us is that the most powerful stories aren't about people who got it right from the start – they're about people who got it wrong, sometimes spectacularly wrong, but kept going anyway.

If you succeeded on day one, you'd have a moment to share. But if you failed for a year, picked yourself up, and finally broke through, you'd have a journey to share.

That journey becomes a map for others. Your struggles, while feeling like setbacks in the short term, become the most valuable parts of your story.

Because nobody relates to perfection.

They relate to the person who faceplanted in front of their first audience, who uploaded videos to single digit views, who wondered if they were fooling themselves – but did it anyway.

Those are the stories that give others permission to start their own journey, with all the messiness that entails.

Robert McKee, one of the most respected experts on storytelling, captured this perfectly when he said:

"What ATTRACTS us to story is the desire to experience that which we have not experienced. But what HOLDS us in story is the experience of that which is recognizably human - and the more difficult the experience, the greater the story."

Joseph Campbell's framework for writing referred to as The Hero's Journey reinforces this in that it proposes the hero must face trials and failures.

These struggles are what make the journey meaningful.

But what's important to recognize here is that this isn't just true for books or movies; because as Donald Miller reminded us a few moments ago… your life is a story you're actively shaping.

So when you reach success, the failures are a multiplier for how much people will care.

You can see this with any successful creator, entrepreneur, or celebrity who interviews well. The most likeable ones never hesitate to point back and laugh with their audience about their early mistakes.

But this isn't an accident or act of humility. They know the power these early failures hold.

And the most effective examples are when they can point to those early failures and you can go see it for yourself.

This proves they are real and tangible, not just some fabricated story to appear relatable which is something that those who reached success without much friction often do because these early pitfalls hold an incredibly powerful psychological effect that is able to humanize them.

The best way to connect with people, whether they're your fans or customers, is to be relatable.

Relatability drives people to root for your success and trust you to help them succeed.

If successful creators and celebrities find it so valuable that they often fabricate these failures, there's no reason to avoid genuinely making them yourself.

If you don't have failures, you haven't taken enough swings yet. If you don't have embarrassing stories of your failures, those swings weren't big enough.

If you're afraid of what people today will think of you, remember that your future fans will find gold in today's painful, relatable failures.

The Identity Shift

The third reason why starting your channel is valuable even if it fails comes down to how we think about identity and success in creative fields.

Naval Ravikant has this great quote where he says:

"We're still socially hardwired to not fail in public under our own names. The people who have the ability to fail in public under their own names actually gain a lot of power."

When we say we want to be a creator, what we're really saying is we want to be a successful creator.

That silent qualifier isn't inherently wrong - of course we want to succeed. But it creates a paradox: because we can't become successful at something we never start.

I want you to look at this through two different lenses that reveal something fascinating about how we think.

In gaming for example, no one waits until you beat a game to call you a gamer. Dying in a game doesn't revoke your gamer card - it's literally part of the experience.

The identity comes from engaging in the activity, not from mastering it.

Or let's take something more universal as an example, with science in general. A scientist isn't less of a scientist when an experiment fails.

That would fundamentally contradict the scientific method itself - failure is built into the process of discovery.

When an experiment fails, we don't question the scientist's identity. We recognize they're actively practicing science, because failure and iteration drive understanding forward.

Creative work is no different: just like scientists experiment and gamers play, creators create.

But for some reason we've turned titles like creator, artist, and YouTuber into nouns - achievements to unlock or identities to earn.

When in reality, they're verbs. They're the work we do, practices we engage in, skills we develop through action.

The moment you pick up a camera and upload content, you're a creator. Not waiting to become one or attempting and failing to be one - you're actively practicing AS a creator.

Think about what being a YouTuber means in practice. You observe what works in your niche. You form a hypothesis about what might resonate with your audience. You create a video to test that hypothesis.

You study the results - not just views and engagement, but comments, feedback, what made people click away. You take all of that learning into your next video.

That's not just similar to the scientific method - it's exactly how innovation happens in any field.

But, we still get caught up in treating "YouTuber" like it's some final form, some achievement to unlock. I've seen this play out for twenty years in creative fields.

Talented creatives waiting for permission to refer to themselves as something in fear of being called out as not a "real designer, artist, or whatever title" because they simply don't yet earn an income from the practice or use specific tools, or approach work in a certain way.

This is a result of very real gatekeeping and stigmas that stifles more potential than any lack of talent ever could.

But this isn't limited to just artists or designers, we see this manifest in any field rich with imposter syndrome - and YouTube is a perfect example.

Those of us who have reached certain milestones try to gatekeep that success to protect our identity because it feels fragile.

We define ourselves by metrics - subscribers, views, income - rather than by the actual practice of creating.

Which brings us to the fundamental truth of this lesson that: success isn't a prerequisite for identity - it's an outcome of consistent practice.

As a creator, your task is to observe, form hypotheses, create content against those hypotheses, study how an audience responds, learn from those responses, and move forward with new knowledge.

That cycle of failing, learning, and iteration isn't just preparation for the job - it is the job. The metrics are simply milestones along the way.

99% of would-be creators never start because they worry about that first viewer who might see their work fail.

They fear that if someone discovers their early attempts, that the viewer won't subscribe, that the opportunity will be lost forever.

But this completely inverts the process. By failing now, you initiate the cycle that leads to better work.

And when those future videos pick up traction, if that same person comes across your new video and somehow remembers your early attempts, the only question they'll ask themselves is how they could have been so wrong the first time around about the value you have to offer.

But the truth is, while those first videos may have not actually been valuable to them, they were incredibly valuable to you.

Because you were in your era of collecting your dots, of developing a story others would relate to in your success, and were taking your first real steps of establishing the practice of what it means to be a creator.

You were capitalizing on the failure, rather than remaining at the starting line, trying to avoid it.

If you enjoyed this letter you can watch it in more depth ​over on YouTube​.