There are two primary levers that you have in your life for financial measures.
1) Income
2) Expense
In choosing the assets you own, you need to consider these levers.
Expenses usually come from the assets you own. If you’re most Americans, your house and cars are the largest expense buckets and most of your wealth is tied up in your home. Anything else is probably in stocks somewhere. That’s fine, and those are also not cash generating assets in the truest sense.
Increasing your income can happen through raises and job changes, but the fastest way to do this is by owning more cash generating assets. Have you thought about this?
Two questions to ask yourself:
1) What is your wealth target?
2) What is your wealth generation strategy?
Vehicles for Growth
Everyone has a wall they hit with growth. The question is what to do once you get there? I’ve found these tools help me a ton as I look for ways to grow.
- Books —> Reading is helpful beyond the information. Training your brain to intake deeper and longer form information is an activity that our society has lost much of, but it’s incredibly necessary.
- Print —> If there are a lot a charts
- Audio —> If it’s a story form
- Podcasts—> Honestly on this, just do it. Too much entertaining content with a low effort bar on the consumption. Even if it’s outside of your normal scope of thought, I’ve never found it harmful to know a little bit about a lot of things. That said, here are the three areas I tend to live in:
- Business —> Generally, but not always, finance. It’s always helpful to understand how finances impact organizational decisions so the more understanding you can get here the better.
- Leadership —> Things like EntreLeadership or WorkLife are very helpful in thinking through how to lead teams.
- Edutainment —> Basically, tons in this area so it’s hard to recommend one in particular. Lately, because of a cyber security interest I’ve been listening to DarkNet Diarires.
- Videos —> YouTube has so much on there. Beyond that, find 3 good movies about something you’re interested in from history. Don’t watch just for entertainment though. See what the diverse perspectives of others can do with the same story.
- Relationships —> The most growth I’ve experienced is from sticking in long term friendships where the other person had enough context to call me when I was lying to myself.
Who is in your orbit that you can trust to challenge you in a safe way?
Can you challenge each other?
Do it!
What are some other vehicles of growth that I’m missing?
High Performers and Self-Feeding
I had a conversation about growth with one of my staff the other day about the fact that he is incredibly smart, talented, and hardworking. That sounds like a good thing and in a vacuum it is. Here’s the thing though, he has currently refused to read books, listen to podcasts, or find other ways to grow outside of picking up things from those in his immediate orbit. I had also struggled with how to communicate the reality of what damage not growing through other mechanisms that aren’t direct experience would cause. Finally, I had the thought. The challenge I presented to him is that at some point he hits his ceiling and then he’ll need to find a way to push past the barrier of his immediate vicinity.
When you get to your capacity there are very few choices of how to grow and at some point you become the ceiling for your team. What do you do in those moments to continue growth? How do you find other people and places that will challenge you with where you’re at? I can say after years of self-feeding I’ve learned to do this for myself. My current challenge is helping others learn this for themselves. How about you? Do you actively or passively pursue growth?
Leveling Up is Your Decision
If you don’t know who Chris Lighty is, that’s ok. Chris was the business manager for most of the large names you would have heard of coming out of the HipHop scene from the late 90’s early 00’s. He was known for his incredible work ethic. The thing is, no one would have known about it if it weren’t for this one moment. There was a point he was in a club with some folks and got into a fight because of some random beef he’d had with folks. From there, someone took him aside and explained to him that they liked him, but also made it clear that he can’t do that anymore. So Chris was faced with a choice to stay the same or up his level.
I constantly have this thought. “Is this my Chris Lighty moment?” Existing in a rapid growth environment will cause you to run into enough people who work extremely hard but, for a myriad of reasons, are in a place where the company might have outgrown them. In those moments, I try to be as clear as possible with those staff members about their ability and my concerns. I’m also certain that everyone has a ceiling. That will come from either ability, or choice. If mine is ability then I hope someone will be gracious enough communicate that to me. If it’s choice, then that’s only something I can know. All roles have a cost. They require too much of the personal end of the life balance. Some roles are simply not worth the transaction cost to achieve the position. The only way to know that is to be clear on your own personal boundaries.
It helps to be clear on those so that you know when to say “I need to change to level up.” or “I’m ok and that’s not worth it.” I’ve found the clearer you are about this, the more comfortable everyone else is with where you’re at. What are your limits before you’ve given too much for a role and where are the areas you need to commit to change and growth?
Technology Business or Technology Enabled Business?
Over the past few years I’ve had to rethink my understanding of the underlying finances of a business. This is necessary when developing your investment thesis. FinTech is a good example. If you look at the trajectory it shows what people are discovering. A NeoBank that was treated as a SaaS company during ZIRP is being realized as simply a bank because the unit economics support that. This is why so much in a lot of companies needs to be written down.
The prevalence of the thought that “every company will be a tech company” simply isn’t true once you apply the unit economics of the vertical that the business exists within.
Everyone else seeing this same rework to investment thoughts?Technology Business or Technology Enabled Business?
Over the past few years I’ve had to rethink my understanding of the underlying finances of a business. This is necessary when developing your investment thesis. FinTech is a good example. If you look at the trajectory it shows what people are discovering. A NeoBank that was treated as a SaaS company during ZIRP is being realized as simply a bank because the unit economics support that. This is why so much in a lot of companies needs to be written down.
The prevalence of the thought that “every company will be a tech company” simply isn’t true once you apply the unit economics of the vertical that the business exists within.
Everyone else seeing this same rework to investment thoughts?
Extractors and Fillers
Steven Freidkin posted about the tension you find from being in the privileged place of being good at solving problems that also counterintuitively will bring you more problems to solve. Check it out linked below.👇 I’d like to riff off that for a moment.
https://www.linkedin.com/feed/update/urn:li:activity:7206267953606995970/
There’s an old jewish proverb: “if you work with your mind sabbath with your hands and if you work with your hands sabbath with your mind”
Because of the dynamic of never ending problems generated by growth:
-I’ll never not be a dad again
-I’ll never hold a position in a business again where my job will not be to simply look at problems and solve them. (Frankly, I think I’d be miserable if this wasn’t true.)
The work seems never ending and that can be an exhausting thought.
In that i’ve found that if I do something in the opposite realm (flipping from mind to hands) allows me to see something finished. The ability to see a finished work at least one day a week adds rest back in a way that gives me energy for the next round of problems the coming week.
With all the extractors, what is your filler activity that sets you up for the next week, the next round?
Empty Space
How redlined are you?
Empty space is one of the best gifts you can give yourself. Some call it shower time, I think in terms of social gears where this is gear 1. It’s a big deal. It’s in those moments that your brain is able to cycle out and solve some deeper work problems that otherwise wouldn’t be solved by thinking harder about the problem.
Most of us get in a rut, not when we have too little to do, but too much to do. What about life being too full is a bad thing? Think of it like an engine (sorry Tesla fans). The gas isn’t actually what makes the car go. Combustion is what makes the car go. Combustion is the combination of several things. Sure gas is required, but so is oxygen. It’s actually the empty space that makes the engine fire.
Problems to Solve + Empty space = Brilliant Breakthroughs.
It sounds too simple to work, and it simply does. Proven, over and over.
Practicals though: For me, i’m in an extremely full season so it’s difficult to create that kind of space. I’m sure many of you can relate to that. On a ground level in a busy season this is done by two activities. Long runs and a daily creation of the bullet list wherein I must prioritize my daily activities. I’ve found that one gives space for deep thought and the other gives clarity of priorities that move problems closer to solutions.
What about you? What are your activities that help you solve deeper problems and be thoughtful?
TPG and Ntiva
I started with The Purple Guys late last year knowing that our previous PE partner was towards the end of their hold time. That can make some people nervous, but all I’m seeing is greater opportunity invest in others and participate in creating an incredible organization. Since joining TPG I’ve only grown more excited about that as i’ve continued to see an organization that is committed to people, both internally with our team and external with our clients. This event only sets us in a better position to create and scale that incredible organization for the benefit of others.
Very exciting things to come!
Desk Setup
I love the pics insta sends my fees of really slick desk setups. Would love to be one of those people with the really nice. The thing is, I don’t think mine will ever get there. It tends a bit messier than I’d prefer. The reality is mess is where the work happens. So while I’d love a photo worthy desk, I don’t think it’s in the cards for me. Have some work to do.
What about you? Is your desk clean or do you have some projects to roll through?

Automate the Intern Tasks
I’m running an experiment this year. Anytime there is something that is simple and might be delegated, I see if it can be automated by tech instead of given to an intern.
I’ve been hesitant to do this over the past year due to a value for developing others, so i’m also looking for new ways to intro others into a career that involved more valuable and less busy work.
My start on it was a report I get daily. We’re in the O365 platform so I used Power Automate to
1. drop the pdf to Sharepoint
2. archive the email
3. when a new pdf shows up use a trained ai model to pull data
4. add the data to an excel doc
It’s a daily 5 minute task that won’t have to be repeated by anyone ever again. The way I figure it I’m saving about $140 per month on that one task.
AMA.