Small Wins Big Losses: Lessons in Entrepreneurship
- Durva Mathure
- Jul 9, 2024
- 2 min read
Updated: Jul 18, 2024
The journey of entrepreneurship is not an easy one, especially in the early stages. Everyone loves to talk about their victories and achievements, but rarely do we hear about the struggle of getting that first "yes," the challenge of securing that first call, or the effort required to land that first client.
Today, I am going to shed some light on just that while sharing some of the lessons from my business school that are helping me along the way.
Today’s post has two important lessons. The first one is for those building a two-sided marketplace, like Uber or Airbnb: always try to solve for the most challenging side of the market first. In my case, these are the small businesses in tourist-heavy cities that offer classes and experiences but struggle to fill their seats. By focusing on these businesses, I hope to create a solid foundation for my travel tech solution.
So, for the past week, I’ve been trying to get just one person to agree to an interview. This brings us to the second lesson for today, which is one of the most critical insights from business school: the significance of a bottom-up approach in identifying your customer base. This means finding one customer who has a problem you can solve. Just one. Once you validate that this customer has a problem and is willing to buy from you, you can find others who are similar. This approach saves countless pivots and changes that are inevitable with a top-down strategy.
However, no one taught me that the journey to find that one customer would be so challenging. I’m solving a problem at the intersection of travel tech and helping small businesses that offer experiences and classes and are struggling to fill their seats. When I reach out with this proposition and get no reply, I find myself confused. Am I going about it the wrong way? Is this not a problem people have? I’m not so sure right now. But I guess this is the essence of entrepreneurship—charting your path through uncertainty. That’s what makes it all worth it when you finally do succeed. Right?
As I enter the second week of finding a customer, I’m going to change my approach. Instead of emailing and messaging potential customers for an interview, I’m going to try being their customer first. If I claim that my solution will enhance their customer experience, help them fill their seats, and add more value, shouldn’t I experience it first? How else can I expect them to value my opinion?
So, what I’ve discovered today is this: show that you care, don’t just say it. Your customer should sense your care in your actions because words alone are not enough.
Have you faced similar challenges in your entrepreneurial journey? Share your experiences and insights in the comments below!
Keep hustling!

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