I first became self-employed in the spring of 2013, after quitting a promising consulting job that I could no longer tolerate (that’s a story for another time).

I had no plan and no savings, and for quite a while my only goal was to pay the next month’s rent. Since I didn’t have a clear vision for what I wanted to do, I tried a little of everything: online courses, commissioned writing, paid workshops, corporate trainings, productivity coaching, and a wide variety of other odd jobs for clients.

Eventually, my writing about how to work more effectively with technology started to gain readers. I settled on personal productivity as a niche, and began developing the concept of a “Second Brain” as my calling card. Fast forward 5 years later, my freelance work increasingly resembled a real business, and I began to put in place the foundation I needed to hire a team.

This article describes that journey, including every piece of financial, legal, and employment infrastructure I used to grow Forte Labs to a team of 12. At every stage, I’ve had to “fire” myself from each job and give it to someone else (or to a platform or system). While most people focus on who they want to hire and in what roles, I’ve found that they often forget the foundation that needs to be in place to make sure those hires are successful.

Each project we took on is listed in chronological order by year, including a brief explanation of why we decided to build each one at that time. I hope this serves as inspiration for those who want to follow the same path and grow a team around their work.

Nothing in this article should be taken as advice. Please consult with experts and advisors in each of the appropriate areas to determine the right decision for you.

Forte Labs business systems

Here’s the full list, with each project discussed in detail below:

  1. Hired CPA
  2. Hired bookkeeper
  3. Legal counsel
  4. Hired Certified Financial Advisor
  5. Payroll system
  6. Hired Executive Assistant
  7. Company-wide SOPs
  8. Company-sponsored health insurance
  9. General liability/Worker’s Comp insurance
  10. Company savings and investment accounts
  11. Business Google Suite, Dropbox, and Zoom accounts
  12. Retirement accounts
  13. Customer support system
  14. Hired customer support representative
  15. Hired HR consultants on retainer
  16. HR management platform
  17. Job description/offer letter templates
  18. Employee onboarding checklist
  19. Created Employee Handbook
  20. Workers’ compensation and unemployment insurance account registration
  21. Professional development policy and stipend
  22. Paid Time Off policy
  23. Moved to startup-friendly bank



Hired CPA

Forte Labs was incorporated in 2014, and for the first few years, I put in place only the systems that were strictly necessary for me to do business and not get in trouble with the IRS.

The moment I dreaded most every year was filing taxes. So soon as I had the funds to afford it, I hired a Certified Public Accountant (a tax professional) to prepare my state and federal taxes. He and his team also file quarterly estimated taxes on my behalf so I don’t have to worry about it.

Hired bookkeeper

I soon discovered that without proper financial records, the CPA wouldn’t be saving me much time and couldn’t guarantee the filings were correct. So I had to work backwards and hire a bookkeeper who could turn my bank statements into financial books that were suitable for tax purposes. 

A couple years later, I asked them to prepare quarterly financial statements (specifically, an updated Balance Sheet and Profit & Loss Statement) for me each quarter so I had a better grasp of how the business was doing.

Legal counsel

As I began to work with independent contractors, I hired a lawyer who specializes in intellectual property to prepare Independent Contractor Agreements for me, including Non-Disclosure Agreements. Later on, he also began applying for trademarks in the U.S. and foreign countries and sending cease and desist orders to people who infringed on them. As a creator of intellectual property, the protection I create around that property is paramount. 


Hired Certified Financial Advisor

As my finances started to get more complex in 2018 and I began to have financial reserves for the first time, I hired a financial advisor to help me manage them and plan for the future. 

Together, we created 401k retirement accounts and managed investment accounts for my wife and I. Later on, she helped us create an investment account for business funds, additional retirement accounts to maximize our pre-tax contributions, a college savings account for our newborn son, and advised us on purchasing life insurance as an investment vehicle.


Payroll system

My wife and I began paying ourselves as employees of our business in 2019, which has significant tax advantages over paying ourselves as owners. After a false start using a large, corporate payroll platform used by multi-national corporations, which wasn’t responsive to our needs, we moved over to a payroll system managed by our CPA. This also set the stage for us to begin hiring full-time (known in the U.S. as W2) employees the following year.

Hired Executive Assistant

In late 2019 I hired an Executive Assistant to help me manage the incoming flow of communication and the administrative systems that had begun to require significant attention. I had hired a couple of assistants before, but this was the first one who I felt was committed for the long term. She was initially hired part-time as an independent contractor through an assistant matchmaking service called Great Assistant, and we soon shifted her to full-time employment.

Company-wide SOPs

One of the first responsibilities my new assistant took on was to document the processes and procedures we used as a company. Inspired by books like The E-Myth and Traction, I decided that we needed to systematize how we worked if we were ever going to build a team. I didn’t want to hire people to run inefficient processes and expect them to clean up my mess. I wanted to onboard them onto well-documened workflows from day one.

I had to admit that I wasn’t the best person to create SOPs – Standard Operating Procedures – because I was too close to the work and couldn’t see it objectively. Luckily, it turned out my assistant was the perfect person. I began training her how to complete common tasks via a series of Zoom calls, and she would rewatch the recordings and turn them into checklists stored in a table in Notion. As of this writing, we have over 200 SOPs that anyone in the company can search for and follow.


Company-sponsored health insurance

2020 was the year we began hiring in earnest, with our first full-time Course Manager joining on Jan. 1. Along with that came the responsibility of providing a full set of employment benefits. We started with generous company-sponsored health insurance. Later on this became significantly more complex when we began to hire beyond California. We had to work with a health insurance broker to find a selection of plans that could cover all 50 states.

General liability/Worker’s Comp insurance

We were required by California law to purchase Workers’ Compensation insurance, which protects the company from claims related to disability compensation programs. We took the opportunity to add a general liability policy, since we were going to have employees interacting with customers on our behalf for the first time.

Company savings and investment accounts

2020 was a year of significant growth in the business, which justified the creation of new systems but also necessitated the creation of savings and investment accounts controlled by the company. This allowed us to invest funds without taking them out of the business, and to think about and plan for longer time horizons.

Business Google Suite, Dropbox, and Zoom accounts

We waited as long as possible to purchase enterprise or team versions of the software we use as a business, because they are significantly more expensive and often charge on a per-seat basis. But in 2020 we bit the bullet and moved our small team of 4 people to company accounts for Google Suite, Dropbox, and Zoom.

Retirement accounts

Since we are based in California, taxes are always a concern, and we do whatever we can to minimize taxes within the bounds of the law. One of the best ways to do so is to contribute to employee retirement accounts with pre-tax funds, which significantly lowers the amount of revenue we are taxed on. 

I don’t fully understand all the details, but the dollars we contribute to these accounts serve as a form of profit-sharing for our staff while also coming at around a 50% discount compared to after-tax cash compensation. This gives us a way to minimize our tax burden while also rewarding our employees as the company grows.


Customer support system

As we significantly expanded the size of our Building a Second Brain cohorts in 2021, the incoming volume of customer inquiries and questions became completely unmanageable. We decided to adopt a customer support platform called HelpScout, which includes support tickets, FAQs, and a website badge for people to contact us.

Hired customer support representative

We hired our first customer support rep in the Philippines, and he has since joined full time to help document answers to the most frequently asked questions and respond to messages in a timely, friendly way.

Hired HR consultants on retainer

Up until this point, we had managed all the details of the systems described above on our own, but in 2021 I felt we needed outside support. I hired a Human Resources consulting firm that offers a service for small companies to “outsource” HR before they are big enough to do it in house. 

This has been a very fruitful relationship, as they have extensive experience on everything from hiring and recruiting best practices, to titles and compensation benchmarks, to advice on culture and internal policies, to regulatory and compliance matters, and more. I don’t know if we will ever be big enough to necessitate an internal HR department, but this outsourced arrangement works quite well for us now.

HR management platform

As part of upgrading our HR practices, we adopted a platform called BamhooHR on our HR partners’ recommendation. It’s an all-in-one platform including job postings and applicant tracking, onboarding workflows, and documentation and compliance. It significantly leveled up our internal staff experience and ensured we’re meeting a high standard of professionalism throughout employees’ tenure.

Job description/offer letter templates

We ramped up hiring in 2021, growing from 4 full-time staff to 10. Recruiting each new hire currently takes several months and requires many manual steps. In an attempt to streamline and speed up that process in anticipation of more hiring in 2022, we created a set of templates for job postings and offer letters so we don’t have to start from scratch each time, and we can make sure we’re following best practices.

Employee onboarding checklist

Aligned with the above, we created our first-ever comprehensive onboarding checklist for new hires. It includes over 30 items, from signing paperwork and creating logins to signing the employee handbook and opening retirement accounts. BambooHR keeps track of this entire process with email reminders at each step.

Created Employee Handbook

We also created our first official Employee Handbook, which outlines what we expect of our people, our policies and values, and serves as a useful reference for common questions about how our company operates. We expect to iterate on this over time as new needs arise and we formalize how we do things.

Workers’ compensation and unemployment insurance account registration

Once we started hiring in multiple states, we began receiving a steady stream of forms, notices, and bills from each of the states where we have staff. We have to create accounts in each of those states for Workers’ Comp and unemployment insurance, plus a seemingly endless number of forms that have to be reviewed, and archived or responded to. This is our single biggest pain point right now, and I’m looking for a platform or service that centralizes all this paperwork under one roof. 

Professional development policy and stipend

We created a professional development policy for our staff, which reimburses them for courses, workshops, and subscriptions related to their ongoing professional growth and development. We pay for half of their educational expenses up to a maximum of $3,000 per year, on the condition they report back and share what they learn with the team.

Paid Time Off policy

We also instituted our first official PTO policy, which includes up to 4 weeks, or 20 working days, of paid time off per year. We chose to lump together all the different kinds of PTO into one bucket to avoid detailed tracking. And we don’t track PTO days closely so it’s a loosely enforced policy by design. As long as our people are completing their duties and making progress on their goals, I don’t care when and for how long they work.


Moved to startup-friendly bank

After almost a decade using Wells Fargo, and putting up with a wide variety of limitations and unexpected fees, we finally made the move to a startup-friendly bank called Mercury Bank. They’re far more modern and streamlined, with the option of creating multiple cards for different departments, each with their own spending limits and tracking. Best of all, wire transfers are free!

For the near future

Here are some of the business systems we’re working on in 2022, which we hope to roll out in the near future, sorted more or less by priority:

  1. Company Mission, Vision, Operating Principles
  2. Performance evaluation system and compensation framework
  3. IT Security policies
  4. Reimbursement/expensing policy and tracking system
  5. 401k investment committee
  6. Remote worker management platform

Creating systems “just in time”

The list above represents 23 distinct business systems we built over 7 years, including new accounts, hires, external consultants, new documents, and policies. 

I never set out to create so much infrastructure, but each one became necessary to solve a particular problem at each stage of the business’ evolution. The main advice that I have to share from this experience is to create the smallest, simplest business systems you can get away with, and keep them small and simple for as long as you can.

That’s because each of these systems represents a major investment. Each one is a project demanding an initial amount of time and money to research, design, and deploy, followed by an ongoing expenditure of resources to maintain, update, and communicate to the team. Not to mention the opportunity cost of spending time building internal systems that don’t impact the top or bottom line.

In other words, by creating these systems you are creating a bureaucracy. There is no way around it. No matter how simple and streamlined you make them, each one adds to the maintenance overhead that you or your team have to sustain year in and year out.

It’s tempting to create some of this infrastructure before you need it, because it feels like what a “real company” should do. Every consultant and advisor will tell you that you need more policies and procedures. But only you can look out for the most important element to keep your business going: profitability. 

You can have the most elaborate, sophisticated company structure in the world, but if it doesn’t make you more profitable, there will soon be no business to keep that structure intact. Having good business systems is necessary at a certain scale, but it’s not sufficient to keep a business viable.

Focus on creating unique kinds of value through your work, and once you can afford it, hire the experts that know how to create such infrastructure and have done it before. There is one thing no expert can tell you and that is up to you alone: How to create a product or service that people want, are willing to pay for, and that you’re uniquely positioned to provide.

Follow us for the latest updates and insights around productivity and Building a Second Brain on Twitter, Facebook, Instagram, LinkedIn, and YouTube. And if you’re ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.