Unlock this Playbook
You will gain full access to this playbook - as well as weekly insights to help you learn the material!
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

Automate your investing

The foundations of your business and personal finances are established. Now, it’s time to start investing for the long term and putting your money to work for you.

We’ll set up another automation here, but I want to point out that investment management in itself can never be fully automated and none of this should be considered investment advice.

With that said, the steps to getting started investing are the same for everyone, no matter how much or how little money you have. Here are the steps we are going to walk through:

  1. Identify what you are trying to save for.

  2. Picking the right account for your needs.

  3. Setting up automatic contributions.

  4. Select your investments.

What are you trying to accomplish through saving 

The first step is always to define your goals — whether it’s retirement, college savings, or other goals, you need to know what they are before doing anything else.

Are you investing for the long-term (retirement)? Are you investing for a short-term goal like buying a house or starting a family (3-7 years away)? Or mid to long-term, like a child’s college tuition (18 years away)? 

Your timeline will determine which type of account is the right fit. It'll also influence how you manage your investments.

Pick the best account for your needs

Second, you need to pick your account type. Below is a list of the top accounts designed for retirement investing:

Traditional or Roth IRA

Annual contribution limit: $6,500 in 2023 ($7,000 if age 50+)

What to watch out for: If you withdraw earnings from an IRA prior to age 59½, it's taxed as ordinary income plus a 10% penalty.

The tax advantages: For a traditional IRA, when you contribute, you can write off that year's contributions against your taxable income. Taxes are then paid at retirement. For a Roth IRA, you contribute money that has already been taxed. Then at retirement, you can withdraw contributions and earnings completely tax-free.

Solo 401(k)

Annual contribution limit: In 2023, the contribution limit is $66,000 (additional $7,500 if over age 50) or 100% of earned income — whichever is less.

What to watch out for: If you have full-time employees, you can't contribute to a Solo 401(k).

The tax advantages

  • Traditional 401(k): Contributions are made pre-tax, reducing your taxable income in the current year — withdrawals in retirement after reaching age 59 and a half are taxed.

  • Roth 401(k): Contributions are made with after-tax dollars, meaning no tax breaks in the current year — but at retirement, the money can be withdrawn completely tax-free.

    • Employer contributions to the 401(k) are a tax deduction for the business.


​​Annual contribution limit: $66,000 or 25% of compensation or net self-employment earnings — whichever is the lesser amount.

What to watch out for: If you have employees, you must contribute on their behalf and it must be equal to what you contributed for yourself.

The tax advantages: In general, you can deduct your contributions from the current year's income and withdrawals in retirement are taxed as income.

Taxable Brokerage

Annual contribution limit: Unlimited contribution limits.

  • No income restrictions.

  • No early withdrawal penalties.

  • No required minimum distributions.

What to watch out for: Every time you make trades within the account, it’s most likely a taxable event.

The tax advantages: None — all gains are subject to short-term or long-term capital gains tax.

These accounts can typically be opened at any type of bank or investment company (make sure you research fees and account minimums beforehand), but the two that I recommend are:

Opening an account is similar to a bank account as you’ll need your address, SSN/EIN, banking info, and any other required verification documents. 

Set up automatic contributions

Third, after picking an account and getting it opened, then you'd put money into the account all at once, or make regular automated contributions. Your personal and business finances will dictate how much you’re able to invest, but it’s recommended to aim for 20% of your personal take-home income.

If you’re making $10,000/month, try to save or invest $2,000 each month.

Then, you can use a calculator like this to see what ‌potential investment growth looks like.

Purchasing your investments

Fourth, after you’ve selected an account and deposited money, you need to pick your investments and buy them.

This shouldn’t be considered investment advice, but two of the easiest options for creating an investment portfolio are a Three-Fund Portfolio or Target Date Funds.

There are a million different ways to invest, but I want to quickly break down these two options as they can be done DIY.

Three-Fund Portfolio: The idea is to select three diversified investments for your account and that’s it. The portfolio is commonly created with low-cost ETFs (exchange-traded funds) from Vanguard, like VOO, VTI, or VXUS. If you’d like to learn more about this, I wrote a full article here.

Target Date Funds: You choose when you plan to access the money from the investments, and it manages them for you until you’re ready. For example, you could buy a 2060 Target Date Fund and it’ll automatically adjust your investments over time to match your life stage. These come with higher fees, but make managing investments a little bit easier.

To automate this process, all you have to do is set a regular deposit and once the money hits, after you’ve selected your investments for the first time, it'll automatically invest new money into the same things.

Note: You may have to turn this setting on, but all primary brokerages offer this feature.

All you have to do is select where the money is being transferred from (your personal bank), the frequency, when to start the automation, and how much you’d like to invest each time.

Remember: A standard budget is 50% needs, 30% wants, 20% saving and investing. If possible, try to automate 20% of your take-home income to an investment account to start building wealth or a savings account to build your emergency fund.

Once you’ve gone through the four steps to investing, set your regular contributions, and created your portfolio — you’re “done”. 

As we mentioned in the beginning, investment management can never be fully automated. You need to occasionally check in, adjust, and properly manage your investments to ensure that you’re getting the most value possible.

Get investment advice from an expert

Get help when needed — Paying for quality advice is an investment, not an expense. When you’re just getting started, it makes sense to keep costs as low as possible. That’s what I did. But as you go, you’ll run into situations where paying for professional advice is well worth the cost. For example, I don’t file my own taxes. I’ll happily pay my CPA a few hundred dollars to know that it’s being done right, and so that I don’t have to worry about anything. Here are a few professional recommendations in relation to investments and taxes: 

  • Local accountant - ask local business owners, do a Google search, etc.

  • Bench Accounting - a digital bookkeeping service

  • Hell Yeah Bookkeeping - bookkeeping & taxes for creatives

  • AllStreet Wealth (for Pollen readers - if we’re the right fit, I’ll do any investment management and one meeting per year for 0.25% AUM because Betterment and Wealthfront charge the same for a lower quality, robo service) 

  • Whisper Financial - financial planner for creatives

  • Camp Wealth - financial planner for solopreneurs and content creators

  • BrooklynFI - financial planner for creatives and business owners

Putting it all together 

As we mentioned at the beginning, you most likely won’t have everything automated in a week, each step is a progression and it takes time to figure out what tools and systems work best for you and your workflow. 

The overall framework of automation applies to anyone, but there may be unique aspects of your business that make one step more challenging than others. Test out some of the recommended tools and adjust over time where necessary. 

With this playbook, you have a cash flow spreadsheet, the tools and steps to automate everything, an estimated tax calculator, and real-life examples to get you going in the right direction.

Remember where we started:

Momentum is real. Go get a pen and piece of paper and take inventory of what accounts you have and where money is currently flowing. 

For the first few months of your new system, I recommend weekly check-ins so that you can see where your money’s going. Over time, you can scale back to monthly reviews and check-ins.

Happy automating.

Private network of peers to learn and build with
Education and resources made for independents
The best guidance to move forward
Exclusive data, insights, and deals
Quality programming and events
Seasoned experts to support you
A community of peers building alongisde you
A community of peers building alongisde you
A community of peers building alongisde you
A community of peers building alongisde you
A community of peers building alongisde you
A community of peers building alongisde you
The premier