I failed at video for 9 months — learn from my mistakes!

It’s a hard game, but worth every minute. I hope.
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Howdy readers!

I’ve talked before about the value of building an audience for your business. It’s hard work, but it makes so many other things easier. So today:

  • 8 lessons I’ve learned from my year of video

Let’s do it!


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Now back to the content…

I spent $96,000 producing videos this last year. 

I gained 2,200 followers.

With some videos getting <100 views.

But I’ve finally figured it out. (I think.) 

Here are the 8 biggest things I’ve learned from a year of failing (and now succeeding) at video:

A little background:

I’ve been hard-core creating on social the past few years.It’s been a huge benefit to my business, makes everything easier, and I enjoy the hell out of teaching.

But last year I realized I was basically only on Twitter. And I started worrying: what if Twitter disappears? I needed to diversify.

YouTube was the next frontier for me. And I realized there was a TON I didn’t know. It was a slap in the face.

So this is a thread of all the stuff I’ve learned in the past year. And hopefully it’s a redemption story, because I feel like we finally figured it out.

1. New platform, new content

Twitter is kind of unique. You can get a big audience with relatively smart, top 20% content. Like, I write threads about QSBS and they actually do well. The average sophistication is WAY higher.

On other platforms, you can’t do that. We all joke about how dumb LinkedIn is. Well, TikTok’s even dumber. You have to dumb stuff down an amazing amount to have it work on these other platforms. 

I’m not saying it’s impossible to build an audience with smart stuff, but it’ll be super niche. 

So that was the big takeaway: the audience needs it simpler than you ever imagined.

2. Don’t start with long-form videos

YouTube has been built on long-form videos for nearly 20 years. 

So there are people with huge established audiences, who are years ahead of you on stuff like thumbnails, hooks, editing, and finding the best ideas for their audiences.

It’s hyper competitive to break into that crowd. 

But short-form content on YouTube is pretty new. It’s more of a level playing field, and it’s a great way to build an audience who aren’t ready to more than 60 seconds listening to a random bald dude on the internet.

3. You start in algorithm jail

YouTube doesn’t let you make one great video and suddenly go viral right out the gate. 

They’re very protective of their audience. They won’t risk exposing their viewers to unknown creators, because then they’ll stop watching.

So you start in YouTube jail. 

At first, none of our shorts could get more than 1,000 views. YouTube would just stop showing it to people. 

A little while ago, we got moved into a bigger jail cell, and we’re getting up to 10,000 views. And it seems like we recently got promoted again, with a couple of videos hitting 25,000.

There’s no way around it. The algorithm takes time to trust you. 

Just keep shipping. Daily.

4. Story is everything

On Twitter and in my newsletter, I write in all sorts of different formats: listicles, explainers, breakdowns… but on video it’s all about a hero’s narrative.

Because success in video is all about retention. 

And the best way to keep people watching is by telling a story they want to hear the end of.

For shorts, every story has pretty much the same arc:

  1. The hook — get attention and tease what the story is about
  2. The setup — set the scene
  3. The complication — introduce conflict, friction, or surprise
  4. The resolution — wrap things up with a bow

The challenge for me is figuring out how to follow these beats while still teaching lessons. All in 60 seconds! 

Have I succeeded? The jury’s still out.

5. Play the hits

When a musical artist first blows up on social media, it’s almost always with a cover of a hit song you already know. It gets you in the door. Then, once you’re interested, you go check out their original music. (Or wait for them to do another cool cover.)

I’m using the same tactic. 

We weren’t doing this at first. I was making all original content about the topics I wanted to cover, in whatever format I wanted.

But the algorithm didn’t like it.

So now we’re trying to “play the hits”. For me, that looks like taking topics and stories that have worked for other people, putting my original spin on it, and rerunning it. 

I resisted this at first. I just wanted to talk about what inspired me. The result was 9 months of me talking to an empty room. Like an idiot.

So I’m still going to make original content. But first, we’re going to play the hits for a while and get some people actually watching my stuff.

6. Editors matter a ton.

Nailing your concept and recording it well is super important. But it only takes you halfway. 

The other half is how good your editor is. You want someone who is focused on you — they get to know your style, and you don’t have to keep making the same revisions over and over. 

It took us a while, but now that we’ve got great editors my content is coming to life like never before. I love it. 

So you want top talent here. Either pay up for the best possible US editors, or get a bargain with somebody overseas. We do the latter, working with the guys at Clipt (HIGHLY recommended).

We’ve been blown away at the quality.

7. Start specific

This one took me a long time to wrap my head around. At first, I was just turning my greatest hits from Twitter into videos — stuff like Mind Hacks for Gen X or breaking down the economics of a parking lot.

I was all over the place. And the algo didn’t know what to do with me.

So now I’m staying focused, and making consistent content in my niche: teaching business basics, through stories about companies that people know well. 

Over time, people are starting to recognize that bald guy who talks about business. And the algorithm is starting to trust me — and put me in bigger and bigger jail cells.

8. Video takes patience

After all this effort, I still don’t even qualify for YouTube monetization. I have earned a total of $0 from my videos.

But I’ve been learning all these lessons. And after months of learning to tell stories, pivoting to short form, investing in editors, and playing the hits — we’re starting to see progress.

I’ve had a short go properly viral now. This gem will hit 1M views soon on Tiktok. (Check it out on YouTube – gotta get those views up!)

My goal is to get a video to a million on YouTube in the next month. And Dylan and Henry have been coaching me to get there.

Once I get an audience, I can start making more of the original content that inspires me.


Here are my takeaways:

1. Different platforms = different content

2. Don’t start with long-form

3. You start in jail

4. Tell stories

5. Play the hits

6. Don’t skimp on editors

7. Start specific

8. Video takes patience

My goal — and what makes me happy — is to teach people at scale. It’s been a fun challenge trying to figure out how to get there.

What’s worked for you? What should I do differently? 

Also — gotta give mad props to the Clipt guys, Dylan and Henry

Everything I know now, they taught me. Give them a follow to learn a TON about video. And they can get you great editors too.

3 things from this week

  • Appetizer: I’ve had software on the brain. Here’s my thread on the 10 reasons I think it’s the greatest business of all time. 
  • Main: Reminder! Next Wednesday is the next chapter in my free HoldCo Lecture Series — join me and Heather Endresen (Viso Business Capital) to learn about how to finance a business acquisition.

    Register here! If you can’t make that time, still sign up and we’ll send a recording afterwards.
  • Dessert: You just can’t argue with that kind of discount!

Have a great week!