Cofounder Dating Best Practices

Gloria Lin is the CEO of Siteline, was previously head of product at Flipboard and a product manager at Stripe, and is an alumnus of South Park Commons. In the process of starting her company, she developed and hardened a set of best practices to find the right cofounder. They’re detailed in this article on First Round, and it’s a must-read for any future entrepreneurs who might be looking for cofounders. She kindly joined a roundtable with the SPC community to take us through her own process finding “the one” and answer some of our questions.

Before Cofounder Dating

According to Gloria, it’s great if you have a specific idea already, but it’s also reasonable if you are in the pre-idea stage looking to explore with a cofounder. You should have an idea of the skills, experience, and domain knowledge you bring to the table, and think at a high level about what skillsets and qualities you would like to see in a partner. One shouldn’t be too prescriptive — finding someone with chemistry isn’t easy and relationships need to past many tests before evolving. In Gloria’s case, she knew she wanted someone with a background in engineering with strong leadership qualities, and could balance her long-term vision with short-term planning and action.

Remember that intuition plays an important role. You can develop your intuition with coaching, personal development exercises like meditation, and experience. Ideally you can consult with a partner or trusted group of friends to help you with tough calls as well. If you find someone you click with on day 1, that’s great! If it takes longer, remember to just keep swimming. She “dated” for over a year before meeting her now business partner, and was very glad that she waited for the right fit.

Should you pick friends for cofounders?

Not necessarily. Professor Noam Wasserman has written that hiring friends can be smoother in the early stages, but can cause issues once the honeymoon phase is over. It can be more difficult to have those hard but important conversations with colleagues if they’re friends, and these relationships can get distorted by new hierarchies in the company. It’s also not particularly important to want to hang out on the weekend with your cofounders. Remember that it’s healthy to have a life outside of work, and having some separation can help you build great “work friendships” with those around you Monday through Friday. People often say you’re getting “married” to your cofounder; she advises that while the co-founder dynamic is critical, your life partner is probably a still more important one!

How vulnerable should you be with your cofounders?

As you move from your first coffee chat to being more serious about each other, you’ll reveal more details about your personal lives. Her cofounder questionnaire promotes vulnerability — share the results if things are going well after a week or two. It’s okay to have personal boundaries with colleagues, but you should at least share things that are important to build a strong, trusting relationship with your cofounder, and to ensure the company is set up for success. The ability to be open about struggles or uncertainties with a cofounder is a strong and crucial foundation on which to build a new startup.

Scrappy Generalists or Experienced Managers?

Think about roles and skillsets you’d like to have on the team, but don’t think too much about whether a potential cofounder will be able to manage a large organization 5 years down the line. Your first priority is survival, and that often means finding people who are smart, scrappy, and can get things done in the early days. If the company is successful, you’ll see how your early team scales with the needs of the company. Sometimes people are able to grow and mature with the company, and sometimes it’s a better fit for a cofounder to lead a specific area or become a high-impact IC. These conversations will be easier if you’ve built trust with your team, and they know that you have the long-term interests of them and the company at heart.

Testing the Relationship

Prior to commitment, Gloria says you should work together on something that closely resembles the actual work you’ll be doing. Try writing code and build something together. Try to sign up customers and put out marketing and landing pages. It’s okay if the work is created just to have an excuse to work together, the important thing is to get signal on what it will be like working as a team.

Does it make sense to live together? She personally wouldn’t do it, but if it helps you get a feel for compatibility, and you’re brave enough, then it could be a good idea. Should you cofounder date in parallel? She didn’t, but adds she could see how some people could make it work. Overall, each of her cofounder dating periods lasted between 3 days and 3 months. In her case, she discovered it was a fit because they had complementary skillsets, similar levels of prior experience, had built up a lot of trust and openness, and even found that they tend to make very similar decisions with the same information, which led to a high degree of alignment.

Top 3 Lessons Learned

1. Don’t be afraid to pull the plug early if it’s not working out, either because of an explicit decision or intuition.
2. Invest in the other person. Be open, honest, and vulnerable with each other. You need to be able to rely on them 100%.
3. Just keep swimming. It can take time, but as long as you have the personal runway and motivation, keep going!

Equity

She advised that you should wait to have detailed conversations about equity until you’re ready to incorporate and work together. The final number will depend on many factors, including the skills and contributions you bring to the table, each person’s cash needs and others. Generally, a nearly equal split, with a slight imbalance to act as the tiebreaker, is probably a good starting point (try some of the online calculators to help with specifics, like this one from foundrs.com).

Continuing the Partnership

She advises starting off most interactions with her cofounder and team with appreciation. A lot can go wrong in an early stage startup and this really helps to keep everyone in a positive state of mind through it all. She also shared marriage advice from John Gottman for a successful long-term partnership — “Cherish your partner’s dreams”.

So what is SPC? We’re a self-organizing community of technologists, tinkerers, and domain experts based in San Francisco. We are building new (and sometimes unorthodox) ventures — ranging from enterprise startups and consumer apps, to open source ML and civic-tech projects. We come together, virtually and in the physical world, to learn from each other, challenge ourselves, and validate new ideas.

Our members also host a recurring events series. Our goal is to bring new and exciting ideas and technologies into the community as well as valuable learnings from those who have first-hand experience building their life’s work. In the past we’ve hosted Silicon Valley VCs and CEOs like Reid Hoffman and Mike Kreiger, leaders like CEO of U.S. Digital Response Raylene Yung and SF Mayor London Breed, and domain experts like Nobel laureate Dr. Saul Perlmutter, experimental physicist Dr. Rana Adhikari, and Howard Hughes Investigator Wendell Lim, amongst many others.

Our on-the-record talks are posted to the SPC Youtube channel. If you're interested in membership, apply using the application below.