Ajay Yadav, CEO and founder of roommate connection app Roomi, also stresses the importance of building strong relationships.
8 min read
Editor’s Note: Entrepreneur’s “20 Questions” series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.
Moving, with all the attendant logistical headaches and emotional investment, can be one of the most stressful things you can experience. When your living situation is in flux, it can affect every aspect of your life. And that’s before you factor in trying to find a stranger, or an untested friend or acquaintance, to split the costs with you.
This is the problem that Ajay Yadav wants to solve with his company Roomi. He founded the startup in 2015 to help people looking for roommates connect with people who actually are who they say are. Users of Roomi sign up for the service by completing a background check that includes ID verification and social media accounts. If the prospective roommates think they have a match, they can plan to meet through a secure in-app messaging platform.
Since launching in New York City three years ago, the company now operates in more than 20 cities, acquired four companies, raised $17 million in funding and has a user base of 2.4 million.
We caught up with Yadav to ask him 20 Questions and find out what makes him tick.
1. How do you start your day?
I usually wake up at around 5 or 5:30 a.m. I meditate for 30 minutes and read a book for an hour. Then I take Caleb, my puppy, for a walk in the park and workout before I head to the office for a 10 a.m. start.
2. How do you end your day?
I try to have as many evening meals as possible at home with my fiancee Brittany, but before that, I usually take coffee chats with young entrepreneurs seeking guidance and help, making introductions and offering advice where I can. Pay it forward is one startup mantra I try to live by.
3. What’s a book that changed your mind and why?
Zen and the Art of Happiness by Chris Prentiss. The book teaches you that anything that happens in any given moment is the best thing that is happening to you in that moment. Once you accept that, it completely alters how you react to things, bringing more calm to any given crisis or more joy to any given happiness.
4. What’s a book you always recommend and why?
The Hard Things About the Hard Things by Ben Horowitz. People often think running a company is so glamorous, but this book also talks about the harsh realities and challenges associated with setting up and growing a company, which prepares your mind for every eventuality, especially when you might want to give up.
5. What’s a strategy to keep focused?
I have noticed that I am more focused each day that I start with the self-discipline of waking up at 5 a.m., following my morning ritual and sticking to my daily schedule as much as I can. It’s not always possible in a startup [environment]. You have to keep 20 percent of your day aside to address something new and unplanned — but I think I have the ratio down by now.
6. When you were a kid what did you want to be when you grew up?
I definitely did not think I would have my own business. I thought I would work a 9-to-5 job, buy a house and settle down.
7. What did you learn from the worst boss you ever had?
I’ve always worked for myself so I haven’t had the pleasure. But on the flipside I am my own worst critic and I set very high standards and expectations for myself, which I am learning to manage better and sometimes frame as ambitious stretch goals to drive me, instead of drown me.
8. Who has influenced you most when it comes to how you approach your work?
My fiancee reminds me to be grateful every day and asks me to remember the company vision and why I am building the company. We believe that very few decisions are more important than selecting your home environment since it directly impacts your wellbeing. That’s why it’s so important to get it right. Also my dad has taught me to never give up, as long as you are solving the right problems.
9. What’s a trip that changed you?
I have been working since I was 17-years-old without much of a break, but two years ago I backpacked across Asia, while working remotely. Witnessing so many different cultures and communities that live so differently to how I was used to in New York gave me a creative boost I didn’t know I needed. It was life-changing.
10. What inspires you?
Working towards making shared housing affordable around the world and less scary when moving from city to city. I also get inspired by community participation. I am involved in a nonprofit called Immigranted in L.A., mostly advising them on fundraising efforts. Coming from an immigrant background myself, this is very close to my heart.
11. What was your first business idea and what did you do with it?
I had the idea of building websites for small businesses when a friend at school introduced me to someone who was looking to build their own website. After learning how to build and deliver one website successfully I was naturally driven to help others to do the same. I formed a small team in India and together we built over 200 sites in three years.
12. What was an early job that taught you something important or useful?
I worked in a motel. I was the front desk manager, but I also cleaned rooms, helped people check in and booked rooms over the phone. I realized that when you accept a role you have to give 100 percent to do what you can in order for you and the business to be successful. That may mean sometimes you have to work outside of the box and regular responsibilities of that role.
13. What’s the best advice you ever took?
Remain as focused as possible to the overall problem you are solving. Concentrate on getting that one thing right and then everything else will fall into place. Try not to get distracted with things outside of the target area and instead manage your time and resources very carefully.
14. What’s the worst piece of advice you ever got?
That you have to work 24/7 [and the idea that] by working more it means you achieve more. In reality that’s just not true because your productivity goes down. You can get a lot done by managing your time better.
15. What’s a productivity tip you swear by?
Sometimes taking a step back from any given situation or problem really adds value in order to fully assess how you should engage next. But also figure out what environment works best for you to tackle different tasks and find your own zone. [Ask yourself,] do you work better in a shared office space, in a coffee shop or a cubicle or brainstorming solutions and plans with your colleagues?
16. Is there an app or tool you use in a surprising way to get things done or stay on track?
A good old-fashioned notebook. I write everything down and cross it all off one by one as [the task] gets done. It never fails and it still feels good to see what you have managed to cross off by the end of the week.
17. What does work-life balance mean to you?
Being able to spend time with loved ones and also with yourself while managing to tick at least two things off your daily task list.
18. How do you prevent burnout?
I travel. It’s important to take a break and to see a new city and fully take in its culture, by living like a local for a few days. Whether that’s asking locals for their recommendations or hanging out where they do as opposed to the usual tourist traps.
19. When you’re faced with a creativity block, what’s your strategy to get innovating?
I perform my best under stress. The more stress and pressure I have the more I am able to accomplish. [I’ve also found that a] simple whiteboard [brainstorm] session with my team leads to greater innovation.
20. What are you learning now? Why is that important?
The importance of a visible company value system and vision which unites your team internally is just as important as building something for the external world to benefit from. In terms of acquiring a new skill, I can’t swim and that’s always bothered me, so I’m taking swimming lessons in my spare time.