You Can’t Always Win by Just Playing the Short Game: Interview with Entrepreneur Ajay Yadav

I recently went one-on-one with Ajay Yadav, founder of Simplified and Roomi.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?

Ajay: I think the experience that was most instrumental to my growth was moving to a new country by myself at age 17, not speaking English, and living in the middle of nowhere, trying to learn and fail by myself. I actually failed the 12th grade twice in India. That’s how I ended up in the US for undergrad, where I failed again and never graduated. However, these failures taught me that I didn't really fit into the school system like I thought. With no support system in the country, I had no “Plan B,” no option other than to succeed. So, instead, I shifted my focus to building companies.

I always loved solving problems, so I got into engineering for tech, built early companies like dev shops, and helped people build websites. During that time, I learned a ton about customers and managing a team. Once I started my second company, I learned more about venture backing – what happens when you raise money and how the business changes. 

As a solo founder of my first two companies, I had to do everything myself. I didn’t know many people in the country, so I couldn’t just ask someone for help. I had to start from scratch and hoped that if I just started building, I would maybe learn something along the way.

Adam: How did you come up with your business ideas? What advice do you have for others on how to come up with great ideas?

Ajay: In the early stages, I tend to come up with ideas when I’m facing a problem. For example, I thought of Simplified because my previous companies had marketing teams of designers, video editors, copywriters, and social media managers passing files back and forth without a good way to communicate in real-time. I found it to be very disconnected and thought there had to be a better way to produce content faster. That's what Simplified is.

When considering these ideas, I try to think beyond my own personal problem to analyze the market size for the product or solution. Instead of thinking, “Hey, I experienced a problem,” you have to think about who else is experiencing the same problem.

Adam: How did you know your business ideas were worth pursuing? What advice do you have on how to best test a business idea?

Ajay: I like to do my research. Typically, I look online and find places where people are discussing the problem itself. For Simplified, I went to Fiverr to see what people were saying about design apps. Maybe people were struggling with design or had projects online for design and video tools.  Basically, it’s about going to places where you can find real customers talking about the problem. That’s how you can determine the validity: by sharing, learning, asking and reading.

Adam: What are the key steps you have taken to grow your businesses? What advice do you have for others on how to acquire customers and take their businesses to the next level?

Ajay:  I love this question; I was just reading about it. First-time founders typically chase after growth, while second-time founders are more likely to go after money (like revenue). With Simplified, we knew that we had to grow profitably and sustainably, and we have kept that in mind since day one.

As we grew the product, we also built its growth engine, which was mostly organic using Google and Bing, allowing us to find users at little or no cost and granting us a larger profit from any sales. It serves its purpose – we show up when people search for the problems that we solve. It's a win-win. We create value for users by keeping our costs down to acquire them.

That said, it’s a long game. It takes a couple of years to get that engine up and running, but we were willing to sacrifice and be patient with the process because we knew that we didn't have to burn capital just to grow a user base that is not going to pay us or it's too expensive to be profitable.

My advice to others is to really think about revenue from Day One. If you don't think of revenue right away, you risk burning money without thinking about how you will make it back. That’s why it’s important to invest in long-term growth engines instead of hoping that short-term growth will last forever.

Adam: What are the most important trends in technology that leaders should be aware of and understand? What should they understand about them?

Ajay: One big question that I see a lot from both employees and leaders at companies is, “Wow, so AI is here, and we cannot ignore it. How can I actually use it?”

The reality is that the future of technology is changing and we need to be ready for the technology now by involving ourselves in the learning process, remaining open to ideas, and exploring so we can stay ahead of the game. Instead, you could wait, watch, and be the last one to adopt the technology, but then it’s kind of too late. Then, you face tough competition from similar players and whatever else is in the market. So, we’re seeing leaders seriously looking at how they can learn faster and be open to these new technologies as they apply to our companies and industries.

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

Ajay: I was a really bad manager in my early companies. I was quite young and had no formal experience or training in management and leadership.

Now, things are going much better. Our team members love working with us and love working for Simplified. We put our team members first and keep a very flat structure. As a leader, I’ve found that it’s important to be a good listener and a team player because, in the end, we are all playing the same game. That’s why personal accountability as a leader is also so important.

My best advice for aspiring leaders is not to compromise culture for people. If you stick to your cultural values and filter new hires through that lens, you often find people who fit nicely. It creates a team where everyone is part of one big mission and culture, and I think it's much easier to manage teams like that.

Adam: What is your best advice on building, leading, and managing teams?

Ajay: Listen to your team members. You can’t be a hands-on leader without rolling up your sleeves and getting to work. It’s hard to stay connected to an organization if you are just barking orders. Always check in with yourself and ask what you’re doing to actually help the team.

Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?

Ajay:

  1. Look at the data as-is, and don’t lie to yourself. If numbers aren’t growing, that is feedback you need to pay attention to.

  2. Optimize speed over everything. In today’s world, anyone can start a business, especially now that AI is in play. What makes you special is the ability to execute and out-execute everyone else.

  3. Level the playing field and be open to learning. Just because you did something great does not mean that you will do it again.

Adam: What is the single best piece of advice you have ever received?

Ajay: The life of a founder seems glamorous to the outside world, but in reality, it’s not. A piece of advice I received on one of my tougher days was – This is your story. If you’re going to write one, it better be good.

To me, this means riding the waves. You're going to struggle through ups and downs, but writing a good story means staying in the game as long as you can still play. Then, hopefully, you write a story that people want to read.

Adam: Is there anything else you would like to share?

Ajay: Being an entrepreneur is about being patient. Building a company takes time. It will take a year or even a decade to get there, but you can’t count on getting lucky. You have to play the long game because you can’t always win by just playing the short game.


Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

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Adam Mendler