My New Long Four Edition Process

Stretch Four Insights Volume 15

Happy Saturday,

While my newsletter began as another way for me to communicate interesting things I am reading, learning, and studying as an entrepreneur. There must always be an evolution. This week I wanted to dedicate volume 15 to explaining how I plan to evolve the newsletter with a new edition called the Long Four. In Long Four editions I will go long and write 1500-3000 word essays on other companies.

This week I wanted to flesh out my plan on how it will work, why I will write about certain companies, and let you all know what to expect, how you can participate, and provide feedback.

Long Four Writing Process

Initially, the plan is to focus on companies in the fintech, tax, and accounting startup areas of focus. In the future, I may expand to other areas.

As launch the Long Four edition of this newsletter which will include more deep dives and long-form posts and essays I want to share my process of how I pick the companies I write about with my readers.

1. I write deep dives on companies that have some form of overlap with what I am building at ModernTax or are early-stage. I want to expose my conflicts ahead of time so here is how I decide if there is an overlap?

   • The companies I will write about are selling into verticals that we are not currently selling into at ModernTax. For example, Column Tax currently is selling into NeoBanks. ModernTax is not we sell to mortgage lenders, insurance providers, and governments.

   • There is a mutual investor, friend, colleague, or person I trust who introduced me to the founder.

   • It helps me understand more about ModernTax and our market

   • It is an interesting company

2. The companies are in verticals that I have a reasonable amount of understanding, expertise, or curiosity in. I write about companies that I have some concept or understanding of how they are being built and what problem they are looking to solve in the market.

3. The company may have products or services that you might use day to day in your job, your personal or business finances, and/or your health. I want to introduce companies that you can learn about early on that you may have not heard about yet in an effort to create efficiencies and streamline processes in our lives.

4. There is something deeper than the company's founding that makes it interesting. Silicon Valley can be an insular place. While anyone can start a company, raise money and be successful, historically the same few people, mafias, and networks continue to compound and create more wealth. This is a controversial topic that does not get as much mainstream coverage as it should even at the earliest stages and I want to shed light on that as an outsider myself. I will tend to highlight companies that are going against the grain with their product in markets that are often overlooked or considered boring from the outside.

What I plan not to do:

• I never write about a company where I have not talked to one of the first 10 employees in an intimate way. In some cases, I like to talk to multiple people and definitely I like to talk to the founder(s).

• I talk to at least one investor in the company and preferably someone who invested in the earliest stages.

• I try and understand the competitive space not only from what the company considers its competitor but also from what the market considers its a competitor.

• I am not writing these as ads, meaning companies are not just coming to me to pay me to write about their company. Generally, I am doing the outreach to learn more about the company, or the founder has been introduced to me through someone else.

• I have, or would heavily consider, investment in the company

I enjoy doing shorter form weekly editions but I am excited about going deeper into different companies so if you are building something new that hits on any of these criteria shoot me an matt@stretchfour.com.