Interview with A Founder: Conor McLaughlin (Co-founder of 99.co)
By David Wu (AppWorks Associate)
Conor McLaughlin was previously the Co-founder and CTO of 99.co, the real estate marketplace in Singapore and Indonesia. He spent six and a half years at the startup, whose backers include Sequoia Capital, 500 Startups, and Facebook co-founder Eduardo Saverin, helping to grow it into a $100 million company. As a member of AppWorks Accelerator #21, he is currently working on his next big project, a yet-to-be-named language learning startup.
【What advice do you have for first-time founders?】
First, you need to decide: do I want to run a sprint or a marathon? For a sprint, you may be open to acquisition from the beginning, delay non-startup aspects of your life, give yourself two years where you drop everything to test an idea, choose to raise more money earlier on and thus be more diluted, or do anything else that implies a shorter time horizon. Typically 1-5 years - this can lead to a major boon in a short period of time if executed well. If you decide you are in the sprinting business, you will most likely be pushed toward binary outcomes because of how many investors and employees you have on your cap table. As a first-time founder, you need to be clear with yourself on what you are willing to put on the line. As Reid Hoffman says, it’s like jumping off a cliff and building a plane on the way down… hopefully you build a plane in time.
If you are running a marathon, you are deciding that your competitive advantage is consistency over intensity. You are in this for 10, 15 years. With this time horizon, you will realize you need ways to metabolize stress and maintain emotional, spiritual, and mental health. You need to maintain relationships with friends, family, and romantic partners. When you are looking at this 10 year period, you realize the people around you can only put up with so much. Unfortunately, while work is something people can generally bounce back from, there are many things in life where you cannot - an example is your relationship with your partner. If you’re going to run a marathon, you need to be clear with yourself about what time you have for other aspects of your life and what time you have for your company. Eventually you need to learn what the right speed is where you can run as long as possible. It’s amazing how often it is that those people that keep going, assuming you have chosen the right problem to solve, eventually find daylight. Part of that is just lasting long enough.
Second, you need to revisit and continually ask yourself: should I still be running a sprint or a marathon? Circumstances change. Maybe you sprinted for the first two years to secure interesting results and funding; now it's time to transition to a marathon and clean up the life debt a bit. Or inversely, maybe you're finally leaving the trough of sorrow and it's time to sprint for a bit. Most founders will be in a long distance race with periodic sprinting. From my observation, founders most often stop because of two reasons: They either A) run out of money or B) run out of energy. There’s plenty of advice out there for scenario A (hint: don’t). But in my experience, scenario B is far more pernicious and dangerous to would-be successful founders. If you are in a marathon but fail to pace yourself and run it like one long sprint, you are unlikely to make it to the end.
Much founder advice speaks to this: Don’t let your startup make you fat. Exercise 5-10% of the time. Pick up a hobby outside of your startup. Go home for holidays. All of it leads back to one thing: You need to take care of yourself. Because injury will be far worse for your progress than being a little slower. “Slow is smooth, smooth is fast”, as the US Navy Seals say. This is surprisingly difficult advice for intrinsically motivated founders to follow, because in the event of failure, it makes them vulnerable to the thought, “Well, you didn’t work hard enough.” But for those that already have the hustle, your job is to avoid the moment of epiphany where you look in the mirror and think, “This isn’t worth it.”
All founders will have to sacrifice some things. The point is to not sacrifice everything. It will make you more resilient. Not less. It will give you the space to see situations more objectively and make better decisions. And most importantly, it will let you love what you do because it will remind you that the work isn’t just in service of yourself, it’s in the service of others. I do not think you can judge hard work over a day, or even a year, but I do think you can judge hard work over 5-10 years. Hard work is not just about the next 1-2 months. There will be times when you need to run as fast as possible, but if that is happening all the time you are probably not being smart about the situation. So don’t hurt yourself, be consistent, keep disciplined, and keep going.
Lastly, focus on your metaskills. Public speaking, reading, writing - skills applied in every aspect of your life. Generally what they reflect is learning how to think better. As a founder you need to think about - how can I think more clearly, be more creative, rigorous, analytical? As Warren Buffett and others have said: I have never seen a successful person that did not read as often as they could. Actual books and long form scare a lot of people. That’s your competitive advantage. Read blog posts from smart people, follow smart people on Twitter, listen to podcasts. Always be focused on how you can develop yourself to think better. Fostering the habit of improving your thinking will foster discipline in yourself. And discipline will let you turn that rigorous thinking into action.
【I imagine running the “race” has been especially tough this year. How have you gotten through 2020?】
I have leaned on routine and community. I’ve spent a lot of time trying to foster discipline in myself. I make my bed every morning, meditate every morning, make sure that I go to the gym 3-4 times a week. There’s so much uncertainty in both the world and the entrepreneurial space. Keeping certain things consistent gives me a spine to my life that I can fall back on. If I’m not feeling well, my discipline takes over and I’ll go to the gym. That helps me relieve stress - falling back to routine and having some mainstays of consistency and structure.
And community - it’s been the big mental health zeitgeist of this year. Everyone is recognizing that without the people around us, our mental health diminishes. Joining AppWorks was very intentional so I could surround myself with like-minded people who could question me, hold me accountable, and inspire me. And also just forming personal connections where I felt that I was still taking care of my mental health by connecting with others. Being a founder is an incredibly lonely journey. In the early days, there’s not a lot of people around. Later, when you do hire lots of people, you need to be the boss, the leader - for certain things, you can’t tell the employees everything, and even if you do, there will always be a bit of distance. You need people to relate to - people want to be seen for who they are, and appreciated for what they give. When you are a founder, sometimes it’s hard to feel that you are seen. So I intentionally put myself in situations where I can be inspired, be held accountable, and more importantly connect with others, and feel that I’m not alone. And that me and my co-founders are part of a communal journey with those around us.
【When you talk about how to run the race, I get the sense that you’re drawing from previous experiences and, perhaps, mistakes. What are the mistakes you’ve made in your founder journey and the takeaways?】
I think you could take a calendar, point to a random week, and we could list out all the mistakes from that week (laughs). I do subscribe to Steve Jobs’ philosophy: mistakes will happen, but mistakes happening means we are making decisions. Not making decisions is perhaps the biggest mistake. It’s often the reason for frustration, loss of speed, loss of momentum - so many of the issues you encounter in startups. Not making enough mistakes is probably the #1 mistake that I’ve made.
Second, going back to my advice to first-time founders, is not understanding what game I’m playing. Not understanding that all the money in the world is not going to be worth it if your spouse or partner decides to leave you because you have relegated them to a second-class citizen in your life. I think I forgot that at points. There is more to life than just the company.
Third, be careful about who you choose to work with. At minimum, if you’re doing a standard 8-9 hours at the office five times a week, that’s a lot of time with those people. You want to like the people that you work with - you want to know they’re high integrity, you want to respect their values, and you want to have common values. Choosing the right people that give you energy rather than take it away just makes running the marathon so much easier.
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