Finding a Co-Founder is Hard

What I didn’t know and what I learned along the way building Grubsquad

Written with Shin Wang

You often hear “finding a co-founder is a lot like finding the right person to marry”. Well, not everybody has or will cross that bridge. A more relevant metaphor is: “Finding a co-founder is like finding a partner to help paddle your canoe.” You and your partner will share the workload; however, you’ll often be doing different things. How the canoe steers past the obstacles that you encounter is dependent on how you cooperate and compromise while you both work towards a common goal.

At Grubsquad’s inception, I wanted to focus on quickly validating my ideas about restaurant food delivery in the Houston area. My day-to-day tasks ranged from hiring delivery drivers to on-boarding new restaurant partners and reaching out to customers. While I was able to cover a lot of ground on my own, I got help from friends, family, and yes, even strangers. Throughout the pre-launch stage and the very early days of GrubSquad, I frequently consulted with a good college friend, Glenn. Over the previous years, Glenn had made his own transition from oil and gas finance into the startup world through a couple of accelerator programs. This experience along with his familiarity with the restaurant industry provided me a lot of insights in building relationships with restaurants, as well as “designing” an MVP that would have a decent user experience. I knew he was a hardworking hustler — we had spent countless nights studying accounting and finance in college together. After dozens of consultations with Glenn, I felt that he was the right person to bring onboard to double our efforts and accelerate GrubSquad’s growth. Having similar operational backgrounds, this helped us build momentum and structure early on in the company. We added restaurants faster, significantly grew our customer base, and started strategizing GrubSquad’s future. However, we soon realized that our overlapping skills were not the best thing for the company in the long-term. Looking back, what we should have done instead was to have one person run the operations while the other devoted more time towards finding the missing resources we needed to build out our logistics technology.

In our case, I decided to hire well-vetted local contract developers and designers to build GrubSquad’s web application. While things mostly worked well with contractors, in order to build and test features quickly, we needed a dedicated person who could manage technical aspects and lead the product-build. Despite not having this crucial piece on our team, we pushed forward and continued to grow while the laundry list of new features we desperately needed got longer and longer.

As GrubSquad evolved, needs changed, vision differed and new opportunities came. Glenn decided to pursue new opportunities back home in New Orleans. About the same time, we knew we had gotten to a point where we needed to revamp our web application and turn our focus on mobile. This included streamlining our menu selection, order flow, payment system, and a new group order feature to cement our pivot to B2B (much more on this later). At this point, I knew that what Grubsquad needed was not just a technical overhaul, but someone who could competently navigate and oversee the entire process. This was a tough challenge. Since I had not raised money, I could not afford a high salary for an engineer. Having grown the company for some time now, it was risky to give up a significant piece of it to someone that quickly. No one likes to work for free and giving someone part of your company’s value is a big deal. A convenient compromise to the situation came in the form of a contract-to-hire/advisor position. Going back to the marriage metaphor, we gave ourselves the opportunity to date before getting hitched.

After a vacation with some close family friends, I was introduced to my next co-founder, Ismail. He had a great reputation among friends and the people he had previously worked with. He was very technical, but he was able to break down technical jargon into plain English. He took the time to understand our business and customers. This allowed us to work and produce the product that we needed. After months of comfortably working together and seeing that we were able to push ourselves to be better at the things we were individually good at, we agreed to make Ismail co-founder and CTO. This gave GrubSquad the flexibility to test and launch new features quicker, collect and analyze order data more efficiently and deploy a better product for our customers, delivery agents and restaurant partners.

While this was how my journey to finding a co-founder went, it is by no means gospel. I’ve probably heard of at least 20 different ways founding teams have successfully come together. In hindsight, I learned that, just as it is in marriage, when looking for the “right partner”, it’s important to do everything you can to prepare yourself to be the right partner.. While you are looking for the person that checks all the boxes you’ve identified, you have to tirelessly do your own homework. As a business side founder, spend time figuring out your business model (how you’re going to make money), digging into your financial model, and learning and executing the best strategies to grow your business.

I wanted to share a number of traits to look for in a technical co-founder. Here are my top 5 (not in order of importance).

  1. Technical competence. This is a trait that would complement yours. If your go-to-market strategy or even product revolves around a web or mobile application, then do your homework. This does not mean you need to go learn how to code. What it DOES mean is that you’ll have to take every opportunity to attend meetups, networking events, hackathons, tech communities events to familiarize yourself with the space. This way, you will be able to learn about what’s possible so you know what to look for in your potential technical co-founder. You will need to get your idea out there; ask lot of questions to figure out why and how other people would do what it is that you need; and listen to what they have to say. Find out what kind of work has he/she done before and how relevant it is to what you are looking to build. At the same time, this person doesn’t have to know every framework out there. What helps is that your potential co-founder does know how to build the key parts of your product and guide it from inception to production.
  2. Ability to communicate in a common language. A good engineer is well versed in his or her technical domain. A great engineer is one that is able to translate his technical depth and explain concepts using simple analogies. You will learn more and more of the tech jargon over time and you will probably use it incorrectly for some time. Similarly, for an engineer who doesn’t have a business background, the same approach is needed when explaining financial models. As an aside, it is also important that your technical co-founder is interested and willing to understand the business model and fundamentals of the company, with a desire to bring alignment with the product or service. There’s a NAVY Seals slogan: “slow is smooth, smooth is fast.” In the marriage of co-founders, developing and aligning a common language allows the team the chance to develop fundamentals from the beginning. It won’t be easy in the beginning, but once you have it, you will gain momentum.
  3. Empathy for the user and passion for the mission. Building features on top of features may be easy and it may seem productive. However, it is up to the both of you to figure out why you’re building it in the first place and decide what to build first. It’s easy to imagine the user as yourself, but that’s working from under a rock. The way to figure out why and how an end-user uses or does not use your product is to go talk to them. A technical co-founder shouldn’t just agree with everything the user is saying. A great technical co-founder will help you figure out what’s feasible and help you prioritize.
  4. Accountability and grit. The challenge that I experienced with my co-founder was the logistics of working in two different time zones and having slightly different working styles. We agreed to meet twice a week via video conferencing, consistently followed up daily using a tool called Slack and kept ourselves accountable using Trello. Due to our limited resources, we proceeded in a manner that allowed significant flexibility. Ismail was gracious and we agreed that he would be able to pick up side projects when needed, to ensure he was taken care of financially. While this made things quite challenging at times, we obviously did this out of necessity, but I would not recommend this. If you can afford to have a technical co-founder who spends 100% of his time and skills building your company, I would recommend that. I say this most importantly because building a company is very tasking mentally, emotionally and physically. The early days of exclusive focus is vital to rapid growth. The entire team NEEDS to be devoted to shipping code, growing your company and resting whenever you can.
  5. Resourcefulness. While you’re busy managing customers and employees, your co-founder will need to share the burden. He or she may be privy to tools and processes that will enhance the productivity of the team, the product, and experience of the customer. He must constantly be on the lookout suggesting tools for process and product improvement.

I know there are many more traits I could discuss but these are the ones I found most vital in my GrubSquad experience. I would love to hear what other traits you think are important when seeking the right co-founder. Thanks for reading.

You can check out the other posts in this blog series:

I. Introduction to this Blog Series on Startups

II. Who’s My Customer Anyway