Case Study: Paragon CTO Ishmael Samuel Reflects On How He Chose His Cofounder

Choosing a cofounder is one of the greatest decisions you will have to make for your startup.

Jun 22, 2020

Executive Summary:

The Problem - Picking Someone You Can Work With For 10+ Years

One of the most important choices made in a startup is choosing your cofounder(s) (if you’re not solo). The challenge goes beyond finding someone who has the skills you don’t to be successful but choosing someone you can get along with and improve you as a founder and a person.
Action Item: Think deeply about who would best compliment not only your skill set but also your personality as well when thinking about potential cofounders.
The Solution - Thorough Due Diligence And Network Building To Find A Co-founder

Ishmael found his network invaluable in helping him find a cofounder. On top of leveraging his network, his thorough due diligence helped him narrow his choices.
Action Item: Your cofounder may only be a connection away by navigating your network. Make a list of initial colleagues and friends and begin reaching out to see if they mesh well with you, or if they know someone who might.
The Takeaway - Focus On A Potential Co-Founder’s Track Record And Personality

Ishmael said it well: “Most importantly, be the awesome partner you want to find. You are what you attract, so elevate yourself, and the quality of what you attract will also rise.”
Action Item: The best way to attract a great cofounder is to be a great founder. Elevate your own standards and you’ll attract individuals who exceed them.

Today, every company is a software company or needs to be to some degree, yet not every company or entrepreneur has the technical expertise to build software or access to top software development talent. Building software is also incredibly complex and time-intensive, even for the best developers. Every company that needs to integrate with a 3rd party API, build an API, or automate processes. The rapid app development market is growing 43% year-over-year and is expected to be $46B by 2023.

Paragon is a visual workflow and API builder. It allows technical and non-technical users to create infinitely scalable production applications without having to write code, manage infrastructure, or develop integrations. Paragon was founded by Ishmael Samuel and Brandon Foo. They previously founded CTRL LA together, a software development agency, and built products for Uber, Universal Studios, and countless other startups and enterprises.

Paragon cofounder and CTO Ishamel Samuel.

The Problem: Picking Someone You Can Work With For 10+ Years

What was the core challenge of selecting your cofounder before starting Paragon?

When starting a company, you should go into it with the belief that you’re going to be working on this thing for the next decade. Every day, you’re going to have to make hundreds of tiny decisions, each moving you forward or backward towards this distant destination.

Additionally, considering that you’ll likely be working with this person 10+ hours a day for at least the next few years and the financial outcome of the business affects literally every other aspect of your life, I believe it’s the most impactful decision you can make throughout a company’s lifespan, potentially your entire life.

With that in mind, I asked myself, “Who can I work with for the next ten years that I can trust to navigate these situations with me?”

What was your initial thought process in selecting a cofounder?

Before starting Paragon, I ran a software development agency called CTRL LA. Being in both a founder and sales role, I had built a strong network and kept a spreadsheet of interesting people I’d met over the course of my career that I’d worked with, referred my business, or had coffee or a phone call with along with notes on what they were working on, industry, location, previous interactions, etc.

I had tags for who I thought would make good hires, founders, investors, etc. I updated this list periodically and ordered them by my willingness to work with them and confidence in a successful, healthy relationship. When it came time to choose a cofounder, I looked to this list.

Describe the governing factors related to choosing a cofounder. What are the critical constraints?

Over the course of my consulting, I had sold over a million dollars in contract building software and learned that in the service industry there are seven factors in what makes someone buy from you. They are aware of you, understand what you do, interested in what you have to offer, respect that you are credible, trust that you have their best interest at heart, able to gather or have the resources needed to work together, and the timing is aligned.

These were the same factors I used in picking a co-founder, along with their temperament, values, and ambitions. The most important factor for me was temperament.

With that in mind, I asked myself, “Who can I work with for the next ten years that I can trust to navigate these situations with me?”

The Solution: Thorough Due Diligence And Network Building To Find A Co-founder

How did you evaluate your initial choices before choosing?

People who displayed a positive temperament excelled in their careers and took pride in both their work and learning initially stood out. There were a number of people who were employed at companies but took up extracurriculars learning how to code or picked up contracts on the side that I thought may make good cofounders or early hires. Additionally building and maintaining strong networks were great signs of sociability.

The biggest barriers to working with people who were on the list were risk aversion or obligations at full-time jobs with no plans or desire to leave any time soon.

When you were thinking through your choices, what else did you discover that either confirmed you were on the right track or opened your eyes up to a new consideration related to selecting a cofounder?

I did some due diligence in talking to people that had worked with the people I was considering to confirm they were who I thought they were. Healthy relationships, previous successes, and a strong work ethic were signs of good choices.

One option I considered was going solo and continuing to work on my agency while continuing to recruit. Being in a service business in the software industry positioned me very well for growing my network and continuing to find potential partners or business ideas.

When did you realize that you arrived at the right choice?

Over the course of the first few months of starting Paragon with my cofounder, we booked meetings with potential users of the product. Seeing the breadth of our shared network, the professionalism in conducting the meetings, and how quickly the takeaways morphed into product strategy were the first positive signs in our ability to work together.

Our first round of funding also came together very quickly and on great terms. In a matter of weeks, we had moved into an office, were adequately funded, and had a product vision we were executing on. While ideas, funding, and rent overhead don’t necessarily equate to traction, it showed me we could move quickly.

The greatest early sign to me was our weekly 1-on-1s. Every Friday we reflect on the week, give each other feedback, and figure out what we can do to improve the upcoming week. I’d been doing 1-on-1s for some time, and our ability to speak candidly and tactfully as well as our mutual respect for each other was the highest I’d experienced and gave me the confidence I’d made the right choice.

Seeing the breadth of our shared network, the professionalism in conducting the meetings, and how quickly the takeaways morphed into product strategy were the first positive signs in our ability to work together.

The Takeaway: Focus On A Potential Co-Founder’s Track Record And Personality

How did you then approach the potential person to ask them to be your founder?

I’d been subscribed to Brandon’s investor updates email newsletter at his last company Polymail. When I heard he left the company, I reached out to him for lunch and told him I wanted to work together.

We got drinks near his place and I shared with him a list of maybe 50 business ideas I had and another 100 hundred companies that I had done some research on that had been successful. My thinking was that we could work on anything on the list or something else entirely and have a good shot at creating an awesome company. It was more important to me who I worked with than what we worked on.

What is your general advice for founders on how to think through choosing a cofounder?

Build your network and pay attention to the track record of what people do and say. Stay away from temperamental individuals, as you may eventually be on the receiving end. Don’t take on rescue projects or people whose only redeeming factor is that they’re available or hungry for it. That’s the floor, not the ceiling.

Instead, seek out those who are better than you in aspects that compliment your skill sets and that you can learn and grow from. Seek out individuals who specifically want to build a company and have experience doing so in the past as opposed to someone who wants to just tag along for the ride. Use their previous accomplishments as a rough measuring stick, and ponder whether this person will succeed with or without you and if they’re a positive or negative force multiplier.

Ask yourself, “Would I want to work with ten people like them?” They’ll recruit others like them, and so if it’s not a no-brainer, don’t do it.

Most importantly, be the awesome partner you want to find. You are what you attract, so elevate yourself, and the quality of what you attract will also rise.

It was more important to me who I worked with than what we worked on.

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