On this week's episode, I got to speak with Shaun Gold. Shaun is a living polymath. 2x best-selling author, entrepreneur, speaker, startup mentor, screenwriter, Jeopardy contestant, and former nightlife ninja. In this episode, we talk about his most significant learnings from previous ventures and dive into the growth behind his latest endeavor Youtopian Journey. (Also @Shaun hope you like the intro music I picked for you)

Admittingly I struggled with how to approach summarising notes from a guest post like this. There was so much rich content spanning such different topics. Rather than write an essay about the conversation I decided to test using a sort of Tweetable type summary. The written part of this post is intended to act as something you can scan through to find topics that interest you most.

Before we dive in, if you enjoy these insights, here are some links where you can follow Shaun for more.

LinkedIn (Make sure to add a note to the connection request)
Substack
Twitter
OpenVC

Before Youtopian Journey there was the Nightlife Ninja

Shaun’s entrepreneurial journey began when he became one of the biggest nightlife promoters in Miami.

Target demographic: 21 -25 college crowd
The hardest part: Dealing with the ‘30k Millionaires’. The most successful people tend to be the most down-to-earth.
The best part: Getting to the tipping point where the same or bigger outcomes could be achieved while working fewer hours.
Pivot trigger: Someone being too young to understand a ‘Van Wilder’ reference.

The Three-Year Grind

The first 2-3 years of anything will suck unless you are lucky and find lightning in a bottle.

Bootstrapping = watching your burn rate constantly
VC route = grinding to find investors that want to invest in you.

The key to breaking past the Silicon Valley of Death is experimentation. If you can’t handle that uncertainty, this may not be the game for you.

Deciding whether to stop or keep going isn’t easy, but learning to accept the process is key.

“A man who has been through bitter experiences and travelled far enjoys even his sufferings after a time”

―Homer, The Odyssey

Don’t be discouraged by failure. Take pride you did something that most have not even attempted.

The purpose of life is to be defeated by greater and greater things

- Rainer Maria Rilke

Every journey has unseen destinations for the traveler. You never know where one path may lead you to.

YouTopian Journey

YouTopian Journey is the world’s first graphic novel for self-help, mental health, and self-improvement. It was created during the pandemic from a desire to create something of value for the world. Shaun’s interest in philosophy, psychology, and graphic art made this a natural project to create.

Progress to date:
- Two years later and there are over 100 issues with 200k+ words written.
- A lot of big names in the mental health space supporting it
  - Collaboration with many of the leading research groups, including Kings College London
Venture size: Doesn’t cost a lot to do, makes money but is not quite enough to be VC-backed.

Market research and product development:

Spent six months writing it out and getting feedback. After sending the artwork to a random sampling of people, there was a mix of positive and negative responses to it.
- Lots of negative feedback, “none of this makes sense,” and “can’t relate.”
- The people that liked it tended to be more successful in their fields.
- Feedback was filtered by taking what was valuable and discarding the rest.
- Some people are right because they are incapable of being anything else - You need to remove these people from your feedback loops.

Go to market:

Doing ads, Substack writers’ hours and partnerships with other newsletters, eventually led to the growth.
- Thought Instagram was going to be the big thing, but Substack was the big thing
  - Substack was the funnel for Instagram.
  - Reddit, LinkedIn, and Quora are where people find these newsletters
- TikTok is not a reliable funnel for conversions. The problems with TikTok are;
  - Nobody knows what’s real or what’s fake. Have you got an engagement rate above 1%? There is no easy way to tell that unless you manually dig into the numbers.
  - Tried collaborations, getting people with 100ks followers to add the link in their bio, but it doesn’t work, only getting 5-7 signups per each of those accounts.
- Jay Clouse talks about how short-form content isn’t what builds a following.
  - Shorts, reels TikTok is too passive, and you don’t build that long-term engagement and following.
  - Much easier to build a true community with longer-form content
Tech landgrabs can be key for early-stage growth.
- Takes a lot of time to pick another new channel, so be intentional with it.
- Be early on a platform and maximize your effort there.
  - Polywork is great right now, but it has six months before it becomes Craig’s list. For example, Lunchclub was excellent for eight months, but the quality dropped completely.
- Bring your work to the new worlds that are still evolving.

Growth Milestones

It took five months to get 1k subs. Insights about getting to paid.
- No guarantees, very hard to get paid - very rare to get 10% paid
- Avg paid newsletter writer has 20 people paid subscribers
- Nobody tells you about churn and how many people leave
First paid subscriber - 20 k subscribers
- Can never tell who is reading. When you go into Substack, the 5-star people who open every issue you think will be the ones who pay, but it’s not. The people who pay don't comment, share, like, or engage. Big visible supporters don’t pay as they believe the way they support is by liking and sharing.
Reader feedback
- Comments like “this made me quit my job” or “ this helped me start a company” have been the biggest milestones.
- People of all ages are reading this, which was a surprise.
- This led to opportunities like discussing mental wellness on the syllabus with the Georgetown MBA program.

Every journey has unknown destinations

The extinction of ideas

The average substack writer doesn’t have the skills to promote and market it. The first two years are going to suck, great writers are going to get discouraged.
The trouble is there will be a mass extinction of ideas - not because they aren’t good but because people expect instantaneous feedback, but that’s not how it was done historically. If Da Vinci had TikTok, would he have given up after the first drawing didn’t go viral? Who cares about instant feedback - honestly, most people just haven’t even seen it.
Don’t let anyone tell you it’s a stupid idea - just take what’s valuable from it.

Advice for readers at each milestone

Group 1 - Idea stage, 0 subscribers

Write one word at a time - writing is the hardest part.
- Worst comes to worst is you learn you don’t enjoy it, and you lose a bit of time. We can live in this state of anxiety of should or shouldn’t I do something. You can be your own editorial director, you make the rules.

Group 2 - 100 subscribers

Going to office hours on Substack and start sharing with other writers.
Best advertising was going to Upwork to get people to promote - without promotion, something terrible happens. Nothing. “I spent years of my life rotting away expecting something extradoniary to happen; the only years where something extraordinary happened was when I made it happen”.
You have to put in the work - 99% of people will say yes to helping
- (Recommended links - communities for writers - maybe send the link to Seans)

Group 3 - What Shaun is going to do next at 22k subscribers

Occasionally do Reddit support
Not at a loss for content
Movie
Physical comic and an e-commerce store (all of which will be an experiment)
- See what people care about because you never know.

If the highest aim of a captain were to preserve his ship, he would keep it in port forever. - Thomas Aquinas

If you enjoyed these insights, here are some links where you can follow Shaun for more.

LinkedIn (Make sure to add a note to the connection request)
Twitter
OpenVC

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