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⚡️ Today’s level up ⚡️

Being a Revenue Generator is richly rewarding. Unlike other corporate roles, those in sales are gifted with different types of income (salary, commissions, RSUs, SPIFFs, bonuses, and more). Today’s edition will share ideas on how to easily put that money to hard work using diversification and a system for leveraging and compounding your assets.

Let’s go!

Read time: <7 minutes

The basics (fill your buckets)

I learned fiscal responsibility, and eventually, fiscal abundance, the hard way.

In 2008, I had to personally file for Chapter 11 bankruptcy. It was all on me – I got over my head spending recklessly as a young adult. Before I knew it, a few hundred dollars in debt became a few thousand to eventually over $35K in the hole…plus student loans (when I didn’t even finish college).

Living and trying to make it in an expensive city, like New York, didn’t help either.

Luckily, after meeting Lisi (my girlfriend at the time, and now wife), she introduced me to better money management habits, and when we got married, my father-in-law became a great teacher.

When you file for Chapter 11, it stays on your credit history for seven years, so I had to completely rebuild my credit from scratch. I learned the discipline of proper spending and how to be resourceful because money would not come easily to me (at least from credit cards and banks). This coincided with me going all-in on a career in sales, where I had more control over my financial future.

These two forces gave me a completely new appreciation for the power of money as a tool vs a status symbol.

Here are a few “golden rules” I learned about the various income streams you’re offered in sales.

Note: Nothing I am providing here is financial advice, I am simply sharing what I did for myself and ideas to consider. Consult with a certified financial advisor and CPA before making any financial investments. (Consider this my legal disclaimer that you are responsible for your own financial decisions).

Base Salary

This is what you want to design your life expenses around. If you can keep your living expenses within your take-home pay, you’ll have more options with your additional employer-based income streams.

So, if you are starting out in sales as an SDR on say a $65K base salary and live in Chicago, work on keeping your annual expenses under your full take-home net pay of ~$50K. If you’re a bit more experienced and a strategic AE based in Austin and pulling in a base salary of $175K, try to keep your family’s annual expenses at your take-home net pay of ~$130K.

Use tools like RepVue to negotiate your base salary, and always ask for more than what’s offered when starting a new role.

Savings Plans and Benefits

This is pretty straightforward: You can pay your future self the maximum allotment. While employed by a corporate employer, take full advantage of any 401K contributions and matching benefits.

Since this was “future money I couldn’t touch,” I wanted to max out everything available to me. I would generally automate this so that any matching and max contributions by taxable year could be realized. Also, talk to your CPA about maxing out other contributions, like Roth IRAs and other opportunities.

Commissions

This is the area where you want to have the most clarity and visibility as a seller. Your commissions (granted, plans will always change) will have the largest impact on your financial gains over the long arc of a sales career.

Knowing I could “pay for life” using my base salary, commission earnings is how I made strategic investments for medium and long-term targets. I would ask myself:

→ “What do I value most?” (For me, it was autonomy)

→ “What accelerates my path to what I value?” (For me, assets that free up my time)

→ “What type of life would I be proud living?” (For me, it was staying healthy and learning)

This channeled spending on things like HALE (health, assets, learning, and experiences) vs more stuff or shallow status symbols:

→ Personal training, meal services, specialists (health)

→ Paying for or paying off a house (assets)

→ Courses and coaching (learning)

→ Travel (experiences)

Stock

Granted, a lot of corporate employees can become millionaires from stock, RSUs, and stock options, especially in the tech space, but honestly, I put little stock (pun intended) in this, because I couldn’t control where the company’s stock would go.

Certainly, I would welcome as many stock grants and RSUs as possible, and view these simply as “gravy on top.” However, I wouldn’t go out of my way to work these into my comp structure or overly rely on them, say like engineers have to, because I knew what was more in my control – creating value as a Revenue Generator. Hence, my commissions was where the real power was.

Other

As you progress throughout your career, don’t discount the power of travel benefits. I recommend developing loyalty to a single airline, hotel chain, and rental car company as early as possible.

Yes, even with AirBnB and Uber, it’s hard to match the perks offered by these companies that you can benefit from later in life.

I haven’t traveled for work since February 2020, but I’m still reaping rewards from airline miles, hotel points, and rental car status that I can use in my personal life today (that’s like having thousands of dollars in rewards).

Pro Tip: Get a credit card connected to each one to maximize your miles or points and try to use these cards for your business travel (vs a corporate card) if your employer allows it.

Easily diversify income through automation

With life expenses covered through a steady paycheck I could manage predictably, my future self being paid the maximum amount allowable by law through automatic 401K and Roth IRA investments, and my commissions going to life-enriching investments of HALE, I then had some left over to take strategic bets and be a bit more risk-prone.

After trying some day-trading several years ago (where I got more lucky than good), I decided to auto-invest in stocks using Stash (no affiliation), where I could set aside a monthly or weekly amount, as well as crypto using Coinbase (also, no affiliation), along with other various broker and savings accounts.

Because I viewed these investments as money I was ok losing, it freed me from the emotional attachment of the natural ups and downs that ensue. I certainly looked at the balances daily, but I allowed the automation to do the work rather than me. It all felt like a fun game.

Before I knew it, the accounts amassed a small fortune (I timed crypto fairly well, starting in 2015 and exiting in 2021).

These investments allowed me to further fund strategic investments within my HALE framework by employing coaching with some of the brightest minds in the world, purchasing a second property in downtown Chicago (that now brings us rental income and gives us living optionality in the future), and an RV (named “Winnie”) that we use for business and pleasure.

The next level

Now that I’ve retired from corporate selling to run a micro business (a business that does not require employees or fundraising to scale), I can rely on these diverse income streams to supplement my growth or strike on new opportunities when they present themselves.

They allow me to make purposeful decisions that aren’t money-necessary, meaning I maintain full control over the pace and direction of the business and our life, and not the need for money.

This opens up many possibilities to pursue ideas I’ve been incubating on and maintain long-term thinking, while freeing up my calendar to do the things I choose.

Being diversified allows me to ride out any macro events that I cannot control.

If for instance the stock market experiences a downturn, I can make more investments on “cheap businesses” by using income from my micro business. If I decide I want to spend less time on the business to focus on writing my book, I can use newsletter sponsorship income, rental property income, or stock profits in Stash to keep my HALE full.

The key is having optionality and knowing what I’m spending on and why.

In summary, the helpful framework that keeps me on track is this:

→ Live on steady income (like base salary)

→ Max out contributions to my future self before I splurge on my current self

→ Make (unlimited) strategic investments in HALE (health, assets, learning, and experiences) with additional income (like commissions)

→ Keep everything protected by diversifying income sources

Hope this was helpful.

See you next week!

🐝

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