5 tips for starting a business with a stranger

When I first thought of the idea for what would become Jobber, I never could have imagined that I would one day be the CEO of a tech company with nearly 100,000 active customers in more than 45 countries. And that I would do this alongside a complete stranger who I met during a chance encounter at a coffee shop.

When you’re first thinking about starting a company, most people would either go at it alone or partner with someone they know, like a friend, family member, or former colleague. Few would consider pursuing their entrepreneurial dream with a stranger. Without proper due diligence, co-founding a company with a stranger can feel like putting a down payment on a new house without opening the front door. While this might not be the right path for everyone, it was absolutely the best move for me.

Jobber is proof that starting a company with a stranger isn’t just doable, it can even be an advantage.

Pursuing a business partnership without a prior relationship has allowed my co-founder Forrest Zeisler and I to be more honest and forthcoming with each other as we worked toward a clear, common objective from the start. The ability to arrive at big decisions and have productive debate without the baggage and bias of a preexisting relationship helped to establish Jobber’s feedback-oriented culture, which is ingrained in the DNA of the company. I attribute our company’s early success to our focus on building a strong and honest business partnership first.

For aspiring entrepreneurs looking to launch a company, I’ve identified five tips that really helped me build trust, camaraderie and mutual understanding with my co-founding partner — a partnership that can withstand intense competition and the test of time.

Start small and aim big

I didn’t know that Forrest would become my co-founder when we first met. As a self-taught developer, I was looking for more sophisticated development help on the project I was working on. During the early stages of our relationship, I would present a problem, such as technical aspects with code, and he would help me with it. Through these initial interactions, it became clear how Forrest’s mind works, and we learned that we worked really well together. At the time, I wasn’t thinking of these tasks as “tests” on compatibility, but in retrospect, they were. If you can’t overcome the small hurdles amicably and efficiently, then how do you expect to take on the big stuff? It’s not a good sign for a long-term business relationship.

Opposites attract

While Forrest and I were both software developers when we started the company, we also brought other complementary skills to the table. Since he was the more proficient developer, Forrest took on more of the core back-end development, while I focused on other components of the product and business that may not have otherwise received the time and attention they needed. I was able to spend time determining our positioning, researching other industries we wanted to serve, and identifying the software features we needed to support small home service businesses. I was also getting on the phone with customers and raising capital. When you have a truly complementary business partnership, you’re able to develop a company with a broader set of capabilities. A co-founding team should be greater than the sum of its parts.

Confront an issue together early on 

The earlier you can discuss important issues, the sooner you’ll be able to determine whether or not you’ll have a successful working relationship. And if, more importantly, your values are aligned. Oftentimes, these issues require more complex problem solving than the technical problems you encounter while getting your business off the ground. Tackling an issue that is more abstract may not always have a right or wrong answer. But even when the debate gets heated, finding common ground is key to building trust.

You’ll never see eye to eye on every business issue that pops up, but as long as your values align and the objectives are agreed upon, it’s entirely possible to “disagree and commit” for the sake of moving forward. When Forrest and I would argue, we reminded ourselves of the greater goal and recognized that these arguments reflected our mutual excitement around what we were trying to achieve.

Expect a degree of give and take in a co-founding relationship. If you’re able to have productive debate, wrestle with an issue, listen to each other’s perspectives and come to decision, you’ll be successful. Develop a muscle for healthy debates early on that services high-quality decision making and biases towards action.

Do your research

When you meet someone who you might want to work with, do some healthy back channeling. Talk to a trusted third-party who may know the person or see if you know anyone in common that can give a recommendation. Think of this process as doing a “reference check,” the same as if you were going through a recruitment process.

When speaking to references, ask questions that go beyond work achievements. Try to get a sense of how your potential co-founder supported company culture or generally interacted with their colleagues. The person you go into business with will play a huge part in establishing your company’s culture. Future employees will inherit the behavioral norms and expectations the founding leaders instilled with each other during the early stages of the company.

Be clear and formalize the arrangement

When I hear about partnership arrangements failing, it’s often because expectations weren’t clearly set out of the gate. Once both partners decide they want to go into business together, the first thing to do is determine the partnership terms. If terms aren’t written down, everyone will inevitably remember verbal conversations differently when it comes time to make a company decision. When two parties are trying to maximize their outcomes, things can get dicey.

When you consider going into business with someone, formalize business arrangements immediately. Have the honest, and sometimes hard, conversations at the start. Make sure you both write down agreed-upon arrangements, even if it’s through something as simple as email. When you have this plan in writing, you eliminate potential problems down the road. It ultimately helps eliminate confusion or uncertainty when it comes to what’s expected.

If you are thinking about starting a company, look beyond your inner circle. While I consider Forrest a great friend now, I believe we’ve remained successful as business partners in part because we didn’t have any personal history weighing us down during the early stages of our company’s development. This allowed us to accelerate early progress that set the tone for many years to come. Remember that the most rewarding and fruitful partnership results, much like everything else in business, happen outside your comfort zone.