My Top Startup Lessons And Entrepreneurship Lessons

Since working on our startup, Mason Park, for about a year and a half, one of the most common questions that come up is “What are your top lessons from working on a startup?”

The lessons learned I’ve learned have been numerous and wide ranging – some expected (eg. you have to be resourceful), and some unexpected (eg. there can be too much hustle). With the different categories and ways to look at lessons learned (eg. what were the biggest mistakes? what would advice would I give others?) there are various “top” lessons I could come up with.

However, if I were to think about high level lessons learned and that I continuously re-visit, they’d roll up to:

  1. Go Deep (With Your Customer)
  2. Move Fast
  3. Have Faith

1. Go Deep (With Your Customer)

While it’s common knowledge that any business should listen to their customers, there’s a difference between listening to your customers and going deep and understanding your customers. We learned this the hard way with the release of the first version of Mason Park.

The first iteration of Mason Park focused on the discovery of beautiful local boutiques. We prominently featured profiles of local boutiques, which people could browse by city and neighborhood. Our early research participants told us that discovery of boutiques is a challenge and we had positive responses to our mock-ups.

However, when we released our first version, users weren’t engaging with the features we thought they’d love.

It turns out that users were more interested in browsing and searching for products rather than discovery of brick and mortar boutiques.

Why weren’t users engaging with features they told us they’d like?

The short answer is what people said they wanted and what they actually wanted were different.

There are a variety of reasons for this, which I won’t get into, but the misstep with our features forced us to overhaul our research methodology and dig deeper with our customers.

Ask Why

We asked “why” not only during our research sessions with users, but also among ourselves after we finished observing and listening to our users. Why did the user ask for what they wanted? Why do they like a certain site? Why do they like the products they like?

Only once we got deep enough could we understand the motivations and desires of our customers and thus connect the dots back to what features they truly wanted.

A goal of any business should be to deliver value and delight customers. In order deliver and delight, you gotta go deep with your customer.

Think From Your Customer’s Perspective

Asking “why” put us on a path to understand our customer deeply. Once we understood our customer intimately, we could place ourselves in our customer’s shoes and think from her perspective. What would she want? What does she expect from us? What would delight her?

We’ve since developed a persona for our customer, Aurora, who is a composite of qualities from our research participants and target customers. Once we had a clear picture of who Aurora was, it became much easier to think from her perspective to guide what was necessary and what would delight her.

2. Move Fast

Another common startup-ism is to “move fast,” as one of the primary advantages with a startup can be its speed. A startup has less layers and processes to make decisions, and since the impact of decisions is usually less than with a large company a startup can presumably act and progress faster.

We knew we had to move fast, but here’s what I learned specifically towards moving fast:

Use Data. But You’ll Never Have Perfect Data.

In the startup world, I commonly hear phrases such as “Data wins all arguments” or “Data doesn’t lie.” As techies in Silicon Valley, we certainly subscribed to this point of view, but one of the things we failed to pay attention was the trade-off with speed and getting data. Sure, data is great, but the reality is that there is likely a cost to the data, or sometimes it may not even be attainable.

For example, when we were deciding on the name and logo for our company, we spent months conducting tests and surveys to get the data that would declare the best solution. Sure we feel confident with what we have, but we also had pressing needs at the time in the form of our MVP.  Looking back, we would’ve been better off making our name and logo decision sooner, even if it meant we didn’t have perfect data. Even if we were wrong with our name and logo, with an early startup, we could’ve modified both later on.

Decision making with data is key, but more even more important is making a timely decision with (impartial) data.

Disagree And Commit

With a co-founder coming from Amazon, we are definitely influenced by Amazon’s way of doing things. Disagree and commit is one of Amazon’s 14 leadership principles, introduced to me via my co-founder, and one that I found to be crucial to us in making faster decisions and thus moving faster.

When we first started, we typically debated until both of us co-founders agreed on a decision. This became especially difficult when there was no clear answer and both of us felt strongly about opposing ideas.

While it’s important for people to share their views and stand up for what they believe in, getting complete agreement from everyone involved can be a big time sink and slow the speed of decisions.

What we try to do now is discuss our viewpoints and alternatives, have the right owner make the decision, and then we all commit and move forward.

Debates with no clear answer kills speed. Disagree and commit.

Execute And Adjust

Moving fast includes not only making decisions fast, but also reacting and adjusting to decisions fast. There’s a lot of uncertainty in the decisions we made, and instead of making the perfect decision (which is often impossible anyways) we are better served to make the best decision we can quickly, observe the outcome, and adjust as necessary.

We did this most with our product tweaks following our various rounds of user research. After gathering data on how our customers reacted to what we put in front of them, we quickly developed a hypothesis, deployed a change to test our hypothesis, observed the outcome, and adjusted as necessary.

Making decisions quickly is important to moving fast, but it’s important to remember that observing and reacting quickly is equally important.

3. Have Faith

Entrepreneurship and startups face a massive amount of uncertainty.  In addition to the many things that probably will go wrong, and the many decisions that are probably wrong, there also always seems to be an infinite number of outside opinions on how things should be done instead. One of my favorite quotes from a friend is “everybody knows your business better than you do.”

All of this drives home the importance of having faith. While it’s important to keep one’s mind, eyes, and ears open for clues and information, faith keeps you going:

Faith In The Vision

The vision is why you’re doing the startup and it drives the direction of the startup. We find ourselves going back to our vision constantly. When we debated what features or tasks to prioritize, our vision steered us. But having a vision in place isn’t enough though, belief and faith in our vision motivates us to drive the startup forward.

Faith In The Decision

With so many tasks and domains new, it was easy for me to second guess and delay decisions. Money, time, ego are all on the line. Instead of worrying about or delaying a decision, I found it better to have faith in a decision once it was made. Second guessing or regret are energy drains.

Faith In Yourself

Faith in yourself sounds obvious, and most entrepreneurs probably already have a good level of faith in themselves. However, I think every entrepreneur goes through a roller coaster of wins and losses, confidence and self-doubt, anxiety and excitement, and more. Faith in yourself can both be zapped quickly or slowly drained. I learned to check in once in a while – without the continued faith in yourself, nothing happens.

To summarize the top lessons from the last 1.5 years with a startup:

  1. Go Deep (With Your Customer)
  2. Move Fast
  3. Have Faith

There are still many important lessons and things to remember from multiple domains and I’m sure others would choose different top lessons from their entrepreneurship experience.

But as we’ve continued on, these 3 lessons are ones that I continually remind myself.



Agree or disagree or have your own perspective to share? Let me know!

One response to “My Top Startup Lessons And Entrepreneurship Lessons”

  1. […] wrote about some key learnings from my experience in posts here and here. What I’ll reflect on in this post are some of the fun and not-so-fun aspects of my […]


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