🟢 Expensive problems are the best
(9.5 min read)
Normally my posts are about my own personal journey and lessons learned.
But recently I decided to do an experiment where I interviewed 3 other writers.
This post is the last of those interviews!
Today’s guest is someone who rigorously analyzes data.
He uses words like “de-risk”, which I love.
And he’s refreshingly, exceptionally transparent.
I’ve appreciated that in his newsletter he tells the truth about 𝕏 and other social media platforms and exposes how people actually attract a following (not just how they say they did).
I’m SO EXCITED to introduce to you… [drumroll 🥁] …
!(P.S. The bold in his answers is mine.)
Interview with of
What’s your “origin story” as an entrepreneur?
What inspired you to take some risks and carve your own path?
Youngling:
Jerry Seinfeld and Louis CK once talked about how they just wanted to be “one of those guys.”
Jerry said that if he could just make enough money to afford a loaf of Wonder Bread and a jar of Skippy peanut butter, he’d be set.
That’s what entrepreneurship has always been like for me.
It’s a vocation – or perhaps a curse is more apt – that chose me more than I chose it.
There’s no pithy, sexy, movie-like moment where I suddenly realized what I needed to do. (Many of those stories are PR fabrications anyway).
But a much more mundane (yet honest) reality that I’ve always just wanted to be independent.
And to me (without passing judgement onto the reader), employment still feels somewhat akin to a parent-child or teacher-student relationship where the former takes care of the latter.
I desperately wanted to be self-sufficient.
Can you share some of the challenges you’ve faced and how you overcame them?
(What pivots did you make along the way to discover founder-business fit and product-market fit?)
Youngling:
Pfew… where to begin. Entrepreneurship is not for the faint of heart and I’ve devoted a non-trivial part of my life to figuring out clever ways to de-risk it as much as possible.
But I made all the mistakes and it nearly cost me relationships and there have been long periods of my life where I’d both wake up and go to sleep fantasizing about ending mine.
A lot of this can be avoided by simply not burning your bridges; the whole no plan B thing.
I went all-in which is okay if it works out… but what if it doesn’t?
I’ve had long stretches of time where I never knew where the next dollar would come from and if I’d be able to pay my bills.
That’s just not conducive to good mental health.
How I overcame them?
Just refusing to quit and staying in the game long enough to get lucky.
But not out of some cool, hero-esque type of mindset… but more because of this curse.
As much as I hated my life, I wanted to succeed even more… and you can’t play the game if you’re no longer here.
What are your favorite ways of earning money right now?
Who is your ideal customer for each of those offers?
What are the main ways they find you?
(I’m particularly interested in both paid and organic customer attraction efforts because I find that getting people’s attention is often far more challenging than offering a high quality product or service.)
Youngling:
My favorite way is to make money by selling my thinking.
I love reading research papers, talking with experts, and making sense of complicated situations.
I love guiding people. So that’s my favorite way.
I enjoy working with beginners and help them monetize their expertise.
But they’re typically broke, so I work a lot with bigger firms where I help them make better, more evidence-based business decisions.
(Also, B2B is just so much easier than B2C.)
You’re right that getting attention is the most challenging problem.
There is no singular marketing channel that works for everyone.
You always have to test.
Not just to see what works for your business but also what matches with your own preferences.
I like cold outreach, content creation (which lets you do warm outreach and can generate inbound), and partnerships.
If you don’t have an audience, can you “borrow someone else’s”?
E.g. I’m currently teaming up with someone who’s got a 60K+ audience to run a masterclass for beginners who want to get into the business of selling expertise.
I think a lot of people forget that, unlike in the gym where you have to do the sit-ups to get the six pack, in business, you can offer the things you’re good at and borrow the things you’re bad at.
You also mentioned paid.
I like sponsorships in that respect.
Especially micro-influencers.
Is there a newsletter who has the customers you wish to serve as well?
In my experience, sponsoring 25 of those instead 1 big one will give you much better results for the exact same marketing budget.
In this journey, what have you been most proud of?
Youngling:
Being able to make enough such that I don’t have to check my bank account.
I can buy groceries, pay bills, and get gas, without ever having to make sure there’s enough money on my bank account.
That, by far, is what I’m most proud of.
A close second is being fully in control of my hours.
If my wife wants us to take a trip in the morning, I have that option.
Oh actually, you know what… From a business POV, I’m really proud of being asked by Meta (Facebook) to give an internal marketing science keynote.
I worked with Noah Kagan and Rob Fitzpatrick.
And I also spoke at the ZeeMELT marketing conference which was televised. (A marketing conference for unorthodox thinkers were mentors of mine like Rory Sutherland and Dave Trott have also been speakers.)
Those experiences were very rewarding and validating.
Some people feel alive—they feel that their lives are fulfilling and interesting.
Others don’t. They could be feeling overwhelmed, uninspired, or disconnected.
Maybe they’re 35 years old and have thrived in the corporate world but feel burned out and don't like the rat race.
What should they do?
Youngling:
START SMALL! For the love of Zeus, start small. Don’t quit your job.
And if you already have, get a part-time gig or do something to make sure that even if you earn $0, your bills are paid. That’s step 1.
Step 2. would be to pick an audience you seek to serve.
Ask yourself who has the audience I wanna serve as well?
Step 3. is to go to that person’s audience and reverse-engineer their EXPENSIVE problems.
Step 4. is to create a value proposition.
And step 5. is to pitch it to 100 leads/day for 1 week.
By the end of the week you’ll either have pre-sold your idea or you won’t.
Now here’s the hard part… If you didn’t sell enough, kill it and try something else.
ALL my hardship can be traced back to trying to make businesses work that didn’t take off. (I call these uphill businesses.)
What if someone wants to buy?
Send them a Wise/PayPal/Stripe/Gumroad/Lemonsqueezy/Paddle link and create AFTER you sell.
You can be totally upfront about this.
“I’m looking for 20 people to make sure I’m not wasting my time. If I can’t find them, I’ll refund you.”
Also, leave money on the table. Your first idea should be <$100. You shouldn’t be optimizing revenue.
You should be trying to reject your null hypothesis:
H0 = There is no market for this idea.
(Notice how failing to reject it doesn’t necessarily imply H0 is true but just that it wasn’t downhill so you’re moving on. There is no certainty in this game. It’s Bayesian all the way down. Act accordingly.)
If you wanna see this in real-time, look at how I’m launching my First Sale Masterclass right now.
Many of us find it difficult to make friends after college.
With technology and society the way they are, what advice do you have for making friends these days?
Youngling:
I’m not exactly a social butterfly but I’m equally comfy being alone as I am being in a crowd or with friends.
If you’re struggling to make friends after college, it’s not because of your age (correlation) but because of your environment (causation).
You’re likely spending way too much time being alone, either literally or figuratively (alone in a crowd).
Go out of your way to make friends.
Chat with strangers even if you find it uncomfortable.
Reach out first is another good tip.
I was a big fan of Ogilvy’s Vice Chairman Rory Sutherland (like many people).
But instead of sitting on my hands, I reached out and he became a mentor-figure.
The same is true for all the marketing Professors I’m close with.
They’re all Professors at some of the best business schools that I just became friends with by “going first”.
If you go first, put a little effort into it, and stay consistent, it’s actually not that hard to make friends.
If you could wave a magic wand and reprogram your mindset in a certain way, what might you change?
Youngling:
Being less stubborn.
I have a tendency to be too iron-willed and that causes me to stick with ideas way, way longer than I should.
If you keep running into a wall and eventually it gives, people write news articles about you and invite you to their podcasts.
But if that wall is made out of steel, your failure remains unseen.
The survivorship bias problem.
However the honest answer is that I don’t know if I’d use that magic wand.
My psychological makeup is probably a complex adaptive system, so if you pull one string, who knows how that would affect the spider web that is me.
And I’m pretty happy with ‘me’.
If longevity escape velocity doesn’t happen in our lifetime, and eventually you’re on your deathbed reminiscing about your life, what would you like to feel about it?
Youngling:
To be perfectly honest, I don’t care.
I’m more of a day-by-day kinda guy.
Hence, my “Chop wood & Carry water” aphorism.
I look up to people like Michael Jordan, Kobe Bryant, Khabib Nurmagomedov, Chef Jiro, Louie C.K., Jerry Seinfeld, Steven Pressfield, etc.
People who’re completely obsessed with the craft.
I view myself as a simple blacksmith or carpenter.
I just want to do the best possible job I can.
Complete devotion to my craft. That’s where my focus lies. The input.
By the way, if you resonate with that, I highly recommend the show The Bear about a Chef obsessed with the craft.
Consider your dream life.
What would an amazing [day/week/month/year] look like for you?
If your current life differs in any way: How so? How do you think you’ll move towards the life you want?
Youngling:
Pretty much what I’m doing right now.
I’ve just started working on my YouTube channel so I suppose it would be nice to have YT be a successful top of funnel…
You know, actually… what would be cool is a bigger audience.
I’d love to be able to share my ideas with more people.
How do I think I can move towards that? I think YT is a good first step.
Perhaps a book deal if I can make it happen one day?
In an average month, what are your revenues, expenses, and profit?
How many hours per week do you work?
(Consider the past few months.)
Youngling:
Mean revenue is 23K with profit being around 80%.
I work 4 hours, 7 days a week.
Deep work from 11-15.
Before that, I’m playing with my 1yo and going to the gym.
After that, I’m cooking and general life stuff.
I don’t count surface-level work.
But there’s a lot of stuff like content creation on X, engaging with other creators, reading research, and sales interviews, that I don’t include.
I think that I’m probably working around 60 hours in total but it really depends on Goodhart’s Law.
Like I said… I have this curse.
So if you give me time, I’ll spend it all on my craft.
But if we’re at my in-laws and doing a bunch of other stuff, I could just do my 4 hours of deep work.
Where have you found the most effective coaching, insights, inspiration, and encouragement?
(E.g. which masterminds or communities do you recommend?)
(What has been rocket fuel for you?)
Youngling:
I’ve learned a lot from my mentors.
Marketing academics like Professor Tom Elmer, Bruce Clark, Alan Charlesworth, and many others.
And industry professionals like Rory Sutherland and Dave Trott.
But I never bought coaching. That’s 1 thing I deeply regret.
I could’ve prevented fucking around for years on my own and it cost me hundreds of thousands in actual costs + opportunity costs.
I can’t really recommend any masterminds because I only have experience with my own group coaching program, but I’d definitely consider not being stingy with coaching.
There’s a ton of noise, but it’s too cynical to pretend it’s all noise.
I believe that I’m signal, for example.
So find someone you look up to and don’t let a few bad experiences convince you paying for help is a scam.
Remember that even in something as binary and easily testable as fighting, there was all kinds of fake martial arts for decades before there were legit MMA gyms.
If you were starting over from scratch, what would you do differently when designing your life and business?
Youngling:
Kill ideas if they’re not downhill during 1 week of trying to make it work.
Pay for coaching immediately. Treat it like a career path.
People go to school for many years and are willing to pay a ton to become a doctor.
That exact same mindset should be adopted if you want to become a solopreneur.
Trying to succeed with a budget of $0 and giving yourself 2 months is so ridiculous that it makes me want to smack those people.
But seriously though, it’s the sign of an Amateur capital A (to use Steven Pressfield’s terminology).
If you can’t bear the thought of this taking time and having to invest even a penny (just like literally ANY other profession), then you can save yourself a world of pain by just getting a job instead.
What are you up to next?
What habits do you plan to have going forward that will help you improve your business and life?
Youngling:
Currently working on my YouTube and trying to grow my X as top of funnel channels.
So that’s my main focus at the moment.
As for products, I’m focused on growing my group coaching program where I help people get into the business of expertise.
This year, I’m going to be shifting away from the beginner market more here and focus instead of people who’re already in the game and offer a service but want to get out of “hands” work and into “brain” work.
Where can we follow you, cheer you on, and support you?
Youngling:
You can follow me on 𝕏 at http://x.com/rj_youngling and subscribe to RJY’s Newsletter here on Substack:
Thanks for answering these questions,
!👀 Caught my eye this week
My favorite part of this recent Alex Hormozi video was where he talked about the powerful concept of “YOU are the niche”:
“There’s a difference between telling people what they should do and sharing the things that you know.
It’s subtle.
But one is preaching.
One is teaching.
And you want to be the teacher, not the preacher.
I think one of the things that [Joe Rogan’s example] has given me permission to do is talk about all the things that I am interested in.”
With this newsletter, I’ll probably talk about various topics that I find interesting:
solopreneurship / business strategy / lifestyle design
technology / the future / longevity / eVTOLs / driverless cars / drones / robots
mindset / personal development / emotional wellness / positivity
veganism
investing
If I were trying to maximize profits, I’d never choose that mix of topics.
But if people do continue to keep subscribing to my newsletter even though I talk about the topics that *I* care most about, how cool will that be?
In the years to come, my interests will evolve, but I won’t have pigeonholed myself into any one topic.
The flexibility will mean I’ll never get bored.
start at 30m03s:
🕙 What we learned in recent posts:
🟢 What I learned managing $210 billion
🟢 Design your work around your ideal life (not the other way around)
🟢 How to be top 1% on Upwork within the first 24 hr of signing up
🟢 Alternative to following some else’s dream
📣 Special thanks to:
of . Nate is a rare find. I recommend subscribing and exploring what he offers. He has helped me think deeper about certain questions that I’d been avoiding.
And if you've got a moment, I'd love to hear what you thought of this email.
Send me a quick message — I reply to every email ❤️
Hey, I know that guy!
A very interesting read. I may not get around to reading when they are freshly published, but I do get there eventually! :-) Have signed up to RJ's newsletter too.