Jeffrey thinks you can't do it twice

Happy Sunday! Here are a few things on my mind...

Why is it hard for founders to be successful a second time?

In the latest Mostly Technical episode, Ian Landsman asks Jeffrey Way (founder of Laracasts) why he hasn't tried building a second product.

Jeffrey:

No, because I feel like it just never works. It's almost as if you can launch something and make money; it's like hitting a jackpot in a weird way.

And you see it all the time: incredibly successful people try to do it a second time, and it doesn't work.

There's this weird combination of being in the right place at the right time with the right idea at the right stage of your life, and then to try to replicate that is really hard.

(Listen to the audio version here)

Jeffrey is right: it's rare for a founder (who has found success) to start a subsequent project that becomes more successful.

I can think of a few:

Adam Wathan was successful with courses before he launched Tailwind.
Rob Walling had Hittail before he launched Drip.
Nathan Barry had a good book/course business before ConvertKit (Kit).

But Jeffrey's point still stands: it's hard to have a second act that exceeds your first.

Why is that?

I spoke at my son's high school entrepreneurship class

On Friday, I gave a 20-minute talk to my son's Entrepreneurship class, and then hung out with students afterwards.

Here's a photo of me practicing the talk beforehand. You can watch a video of my practice talk as well:

This was a significant experience for me on some big levels:

I reflected on who I was and what I knew when I was 17-18. It was surprising to remember how small my worldview was back then. I was living in a small town in Alberta, and all I knew was what was around me.
I thought deeply about which events had the biggest impact on my entrepreneurial journey. Putting on a rave in high school, starting a snowboard shop, and getting my first job in tech were significant events.
Hanging out with the kids after the talk reminded me how important it is for young people to have accessible role models in their lives. When I was 17, I didn't know what was possible. What changed my life was meeting key figures who expanded my worldview and helped me see opportunities I didn't know existed.

As I told my story, I pointed out numerous times where "I got lucky." Luck plays a big part in any success story, but I also emphasized that you can increase your luck surface area.

Click here to see my talk, see the handout I made, and see all these hilarious planning documents I made in 1998 (when I was 17, and planning the rave).

You only get 12 shots in life.

This is good. Personally, I would assign a different “relative importance” to each dynamic listed here, but directionally, this feels correct.

Read the blog post

Why do you never have enough time?

My wife sent me this podcast episode. This part resonated with me:

80% of Americans today say that they are time starved and despite having more tools available to make more use of our time than we've ever had. What's going on with that?

What's really happening is that it's usually about emotional overwhelm.

Time scarcity is almost always a response to stress.

Listen to the episode

Thoughts? Let me hear them!

Cheers,
Justin Jackson – Bluesky

PS: On the latest episode of The Panel, we had Aaron Francis join us!