My Journey (Part 3)

What I learned as an entrepreneur from starting (and shuttering) GiftSimple.

Entrepreneurship was never something I considered. It was for charismatic men who liked to take risks and deliver impassioned speeches to crowds. That was not me—or so I’d thought. However, my first entrepreneurship class opened my eyes to new possibilities.

In addition to writing the financial section for a business plan for fashionable bike helmets with my classmates, I was introduced to other entrepreneurs’ stories through case studies. An academic paper we read, The Accidental Entrepreneur: The Emergent and Collective Process of User Entrepreneurship¹, showed me a different kind of founder—the customer-turned-entrepreneur. I learned that there are many types of founders.

I enjoyed the introductory class so much that I took a second entrepreneurship class. It was in this class that I dreamed up what would become my own company: GiftSimple, a social gifting platform. I grew up saving the money my family gave me on my birthday for some larger purchase I was working toward. I thought others might be doing the same, and I saw an opportunity to make an existing offline behavior easier online: pooling money for a meaningful gift for birthdays, weddings, graduations, and other celebrations. I started GiftSimple in my final semester of business school and decided to spend the following year seeing if I could make it work.

A Crash Course in Building

For the next two years, I had a crash course in starting a company. Nearly everything I tackled was brand new, but I was fortunate to have guidance from my brother Marc, who had product management experience, and folks he trusted, like Jason and Russell. I started by registering a legal business entity and acquiring a domain—simple steps that felt monumental at the time. It was my first time working with a designer on UI/UX wireframes or thinking about how to set up web analytics and tracking—there was a steep learning curve! When the site launched, the focus shifted to customer acquisition. I developed social media campaigns, authored content for the GiftSimple blog, and launched paid advertising through Google AdWords. I’ll never forget the thrill of seeing the very first listing from a customer I didn’t know—it was a small, shining victory.

By the end of the first year, we had built a base of roughly 1,500 registered users, but growth had stalled. Instead of seeking feedback from customers (or potential customers), I doubled down on marketing tactics to reignite momentum. In hindsight, this was a mistake because I hadn’t found product-market fit. It wasn’t until I started preparing to pitch venture capitalists that I could see the flaws through their eyes—what I loved about the idea was also its biggest weakness: social norms around gifting were more deeply ingrained than I had assumed. I spent another year giving everything I had to GiftSimple before ultimately deciding to shut it down. It was a bittersweet decision, but the experience was transformative and taught me lessons that no textbook ever could.

Entrepreneurship isn’t as risky as it seems.

When I first imagined starting a company, I pictured entrepreneurs draining their life savings and living out of their cars. While that may be true for some, my experience was different. I started GiftSimple while in school, leveraging university entrepreneurship programs and a modest amount of startup capital to get it off the ground.

And if that was true then, it is even more true now. With AI, the cost of trying has never been lower. You no longer need the same level of engineering, design, or finance support to test an idea. You can get an MVP to market fast, pressure-test assumptions, and learn whether something has promise before committing years of your life to it.

GiftSimple failed, but so did Lehman Brothers. Nothing in life is guaranteed. The risk of not trying—of never knowing—felt greater to me than the risk of failure.

People don’t always act how you expect or how they say they will.

Social norms around gifting are deeply ingrained. Asking for money feels acceptable for charity or a wedding registry, but for birthdays or graduations? People hesitated. Despite what users told us in research—things like, “I’d love to use this for my next birthday!”—their actions said otherwise. Changing long-standing behaviors is hard, and what people say and what they actually do are not always the same! This lesson has stayed with me: qualitative research tells you what people think they want; quantitative research tells you what they actually do. You need both.

Loving an idea doesn’t make it a good business.

I loved the premise for GiftSimple. It took an existing offline behavior and made it more efficient using the power of social networks. But my excitement didn’t mean it was a good business. Passion is powerful, but it doesn’t automatically translate into a viable business. The VC pitch process was humbling in the best way—it forced me to stress-test my own assumptions and see the idea as an investor would, not just as a founder.

Decisions need to be made faster—and metrics make that possible.

I held onto GiftSimple far too long. Looking back, I knew it wasn’t working after the first year, but my determination and love for the idea kept me pushing forward. The core problem wasn’t just stubbornness—it was that I never set clear metrics or milestones up front. Without them, I had no objective trigger to act on. There was no number I could point to and say: “We said X, we got Y, it’s time to make a call.”

I’ve realized since then that delaying decisions often stems from the absence of a forcing function. When teams lack a clear goal, it becomes too easy for decisions to stall. Setting clear goals at the outset creates the structure teams need to make decisions with confidence. It’s a lesson I’ve carried into every team I’ve built since.

Failure isn’t the end—it’s part of the journey.

When I finally decided to shut GiftSimple down, I felt like I’d failed. As someone who’s always been goal-oriented, it was hard to accept that I’d poured so much into something and didn’t achieve what I set out to do. It felt public and embarrassing.

But over time, I’ve learned that failure isn’t something to hide from. Everyone experiences it in one way or another, and trying to avoid it only limits your opportunities. Failing at GiftSimple taught me that what matters most is what you take away from the experience and how you use it to grow.

What I took away was an operator’s mindset: a bias for action, a respect for data, and an instinct for when to move fast versus when to slow down and get the precise answer.

Those instincts didn’t come from a class or a framework. They came from two years of building something real, watching it struggle, and making hard calls with imperfect information.

As I’ll try to show in future posts, this setback didn’t just build character. It gave me an edge in analytics—and a set of principles I still apply in my work today. In a very real way, that failure became part of the foundation for what came next.

Coming up in Part 4: how I joined DoorDash as its first General Manager, and what I learned about building from zero.

1. Shah, S. K., & Tripsas, M. (2007). The accidental entrepreneur: The emergent and collective process of user entrepreneurship. Strategic Entrepreneurship Journal, 1, 123–140. https://doi.org/10.1002/sej.15