Hey Reader!
My wife and I made a quick trip up to Seattle to see Justin Timberlake live last night. She’s loved him since his N*Sync days and I enjoy his music, so that works out well.
This week on the podcast, one of the most interesting writers of the Substack-pandemic era joined me as my guest. Packy McCormick is the most optimistic man on the internet and writes (very) deep profiles on the most promising companies at the frontiers of technology.
Listen here:
- Apple Podcasts
- Spotify
- YouTube
- Show notes
If you enjoy this episode, please share it with a friend by text and then leave a rating and review.
If you prefer to only get emails about the podcast, click this link and I’ll exclude you from the Saturday newsletter going forward. The link is automagic so don’t worry when it just takes you to the podcast site.
Let’s get to it.
A quote to make you think from a book worth reading
“A job […] is a way to pay the bills, a career is a path toward increasingly better work, and a calling is work that’s an important part of your life and a vital part of your identity.”
-Cal Newport referencing Amy Wrzeniewski’s research in
So Good They Can’t Ignore You
Newport goes on to say the following:
“the strongest predictor of [a research subject] seeing her work as a calling was the number of years spent on the job. In other words, the more experience an assistant had, the more likely she was to love her work.“
This isn’t to say: suck it up and stay put. It is to say that it takes time to build the skills, relationships, and foundational knowledge necessary to find a calling. This is true of the most successful and mission-driven entrepreneurs I know as well.
Three links to encourage deep thought and breakthrough growth
1 Reading Well (2023) by Simon Sarris | Read time: 6min
“Reading is letting someone else model the world for you. This is an act of intimacy. […] And after finishing a very good book one is driven a little mad, forced to return from a world that no one nearby has witnessed.”
To read well is to lead well. This applies more broadly — great leaders curate what they consume with intentionality.
Simon is the rare individual who is both an engineer by trade and what I would call a romanticist by taste. His advice on reading well mirrors much of my own thinking on what makes something worth reading.
The top quality: what you read must be of personal interest above all else.
Questions to consider as you read: Are you reading well? If not, what shift could you make to begin?
2 The Gift of Ambition by David Heinemeier Hansson (2024) | Read time: 4min
“[…]what is ambition, exactly? To me, it’s a leap of faith. A belief in the possibility of success without all the evidence to justify it a priori. A trust that whatever challenges we’ll face between here and there, we’ll be able to figure them out.”
Also known as “DHH,” the author plays an obnoxious character on the internet, strategically using outrage to drive attention to his products and ideas. Yet under the surface I find a strategic thinker who has worked hard through the years to build opinionated products to serve a clear group of customers.
Here his take on ambition is a good reminder that while every great quality has a shadow side, we don’t need to throw the whole concept out to avoid the shadow. Ambition is a good quality. Embrace it.
Question to consider as you read: Are you being ambitious enough right now? What scares you about your ambition? How could you be ambitious and centered?
3 Schopenhauer’s Advice On How to Achieve Big Things by Arthur Brooks (2024) | Read time: 9min
“Go out of your way to be around smart, interesting, ambitious people. Work for them and hire them (in fact, one of the most satisfying parts of work is forging deep relationships with really good people). Try to spend time with people who are either among the best in the world at what they do or extremely promising but totally unknown.”
Big projects designed to create impact take a long time to complete. Maintaining the right mindset and outlook — especially when you’re in the messy middle when nothing is assured other than more hard work — is critical.
The title is trite, the advice is simple, and yet it’s a reminder that what is simple is not easy. Do big things. Do them one chunk of work at a time. Understand the long-term vision. And use each day to get closer.
Questions to consider as you read: What is the big thing you’re working towards right now? What impact will it have on the world if it works?
A Short Essay Based on My Work with Founders
If you’re past the point of your first hire, this may not apply to you, but please do give it a read and send me your advice for others who are considering making their first hire. I’ll compile the advice and share it in a future edition.
Decide On Your First Hire
The scariest hire you’ll ever make is your first hire. Your budget will feel tight, you won’t know what you’re doing, and the process will feel overwhelming. I’d like to try to make it less scary and more matter-of-fact.
Your first hire should serve one of two purposes. They both come back to revenue. They will:
- directly make your business more money
- take things off your plate so that you can focus on making more money
If a hire can’t more than pay for itself through one of those two ways, you shouldn’t make the hire.
Your Hire Should Have Clear ROI
A good benchmark is that any hire you make should have the potential to drive 1.5-2x their all-in cost in revenue.
So, if you hire a $50,000 employee who receives $20,000 in benefits, then that person should help you earn another $105-140k in revenue.
In your mind, you should plan for them to hit that mark 18 months after being hired at the latest. You should also plan for them to have very little productive value to the business in their first six months. At six months, they should be able to do the job without receiving daily direction from you.
In months 7-12, you should act as a coach, helping them reach their potential in the role. In months 12-18, they should be full speed ahead and driving revenue or freeing you up to drive revenue.
That’s your mindset, but you should push for faster execution in reality. If at any point, you know for certain that they can’t hit that timeline, you should let them go. And when you hire, you should look for qualities in the person you hire that will cut the timeline in half.
Break Your Company Down Into Roles
You should be crystal clear on what your first hire is for. What is the business need? The books Predictable Success by Les McKeown and Traction by Gino Wickman both have good processes for understanding the needs of the business and turning them into roles.
Basically:
- Write down every process that must happen in order for your business to run
- Highlight the ones that drive revenue in green
- Highlight the ones that support revenue activities in yellow
- Group the processes into functional areas (these are typically product, marketing/sales, operations, and support)
When making your first hire, you’re almost certainly going to hire someone to own a functional area. As your company grows, each functional area will get further broken down into additional roles.
Ask yourself: Which functional area am I least effective in? Which functional area can drive the most additional revenue? Now, which of those are you going to hire for?
Write The Simplest Job Description Possible
The job description, at least initially, should be as simple as humanly possible. Why? Because simple = you being clear on what you need from this person. Here’s what it should include:
- One primary metric that you’ll use to evaluate this person’s contributions
- Two secondary metrics that support the primary metric and give higher fidelity evaluation potential
- Three core responsibilities
That’s it. If you can’t get that clear on what the job it, you’re not ready to hire. Recruiting and running a hiring process
A quick aside on the most common, but mistaken role people hire first
I most commonly see people hire for customer support first. If that’s your inclination, ask yourself:
- What is the volume of customer support requests you get each week/month?
- How much time, in reality, do those requests take to respond to?
- Given that it is almost certainly not 40 hrs/wk, what else would a customer support person do?
- Since customer support isn’t revenue-generating, will that role really free up enough of your time and mindshare for you to generate 2x their cost in additional revenue?
Customer support feels like the right place to start because it feels stressful if you are handling requests from your customers without a good system. But 9 times out of 10, it’s the wrong first hire to make.
You should instead focus on creating an efficient system to handle your own customer support requests in as little time as possible. The key is to prevent yourself from seeing the requests as they come in, either through a separate inbox or an automatic filing system.
Much love and respect,
If you enjoyed this newsletter, forward it to a founder friend. You can also recommend me to a founder or creator as a coach.