On a cloudy morning in San Francisco, my co-founder and I huddled into a conference room within our work-space. We had recently finished our latest round of user feedback sessions and feature tests and were discussing what was next. On the glass walls of the conference room we were in, we sketched out everything we knew. We listed out all requirements that were still needed and made our best estimates on tasks and risks. After hours of heated debate and discussion, we reached a difficult conclusion: We would cease our efforts with our startup, Mason Park, and shut things down.

Shaken and disheartened, we decided to take a day to reflect and reconvene. When we did, I felt assured of our decision and we immediately focused on the logistics of winding things down.

Why did we decide to shut down Mason Park?

In short, we had still had a lot of effort ahead to get to product-market fit, and also with a significant amount of risk. We were tackling a problem our customers resonated with, we had goods that our customers wanted, but we didn’t have a product our customers loved. Without a product that our customers loved – a product that delighted, a product customers would return to over and over, a product that customers would sing praises of, we knew Mason Park wouldn’t reach its full potential.

Without a product that our customers loved – a product that delighted, a product customers would return to over and over, a product that customers would sing praises of, we knew Mason Park wouldn’t reach its full potential.

Our research and tests directed our product roadmap and unfortunately, we still had a lot of work to do. With an estimated 6-9 months of effort to build, test, and deliver the product our customers needed, and with significant risk, we decided against fundraising and investment and would cease operations.

I 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 experience with a startup.

The Fun

Being Exposed to New (to me) Domains

When I was in the corporate world, there were teams doing many specialized functions. I was able to focus on what I needed to do and could enlist assistance from other functions in the company as needed. Of course in a tiny startup, we’re not only doing everything, but we have to be scrappy, creative, and fast with it. While it was daunting to tread into unfamiliar domains to try and get things done, I had a lot of fun learning about and trying my hand in new domains. While not everything I had to do was fun to me (e.g. legal work, cold calls), I particularly enjoyed user research, UI, and visual design. Utilizing these various aspects together to work towards a useful, simple, and beautiful product was a pretty fun challenge.

Whether You Sprint, Stop, Switch – It’s All on You

In a startup, everything is focused on releasing the right product and building momentum as fast as you can. Time is of the essence, and for a small team every decision can have big impact. We certainly didn’t always make the best decisions and we certainly agonized over some decisions, but I found the daily puzzle of prioritization and decision making to be exciting. Every day was a challenge to decide what and how we were going to focus our very limited resources. We had no idea where the company would go, but we tasked ourselves to make the best decisions we could to take the company where we wanted it to go.

Thinking Big

Before we even started, we had to play fortune teller of where we thought the world was going to go. What changes are happening and where would we fit in? How were we going to impact our chosen domain and customers? Once we decided on a vision of the future, we had to figure out how we’d approach things. During our time with Mason Park, we witnessed first hand the continuing effect of e-commerce on retail and brick and mortar. In our vision of the future, we didn’t see brick and mortar retail disappearing, but rather morphing to a different form that embraces the online and offline experiences as separate, but necessary components to retail.

Technology and the world have been changing at a phenomenal pace, and it’s exciting to think about where the world will go and where the opportunities to add value will be.

The Not-So-Fun

Anxiety and Fear But Everything’s Great

As a startup founder, you have a vision that you’re bringing to life. Enthusiasm and positivity are needed for the vision; whether to motivate the team, to interest partners and investors, to sell to potential customers, or to convince family and friends that you’re doing something worthwhile. Yet a startup is hard. It’s a roller coaster and there are days when anxiety, fear, and demotivation creep in. What makes this hard is that as a startup founder, everything is always great to the outside world. I could be anxious about the future of Mason Park or if we were doing the right things, but to everyone around, we’re working hard, have a plan, and optimistic about where we’re going.

I always found this phenomenon amusing when I spoke with other founders at our workspace. When meeting another founder, the first few conversations were always filled with optimism and the usual startup highlight updates. But after a few more run-ins, somebody would invariably mention the difficulties faced, which would then open the floodgates of founder challenges, anxieties, and amusing rejection stories.

Check Your Ego At The Door

In the corporate world, I had influence and status bestowed on to me by the company I was working for. I traveled the world, had meetings with Fortune 500 companies and humblebragged to friends about the massive impact of my work. Corporate cafeterias, gyms, and salary provided a comfortable lifestyle. In the corporate world, you can be a big shot doing big things.

While the idea of a startup is romantic, the impressed reactions from casual onlookers mean nothing when you’re in the trenches trying to build something from nothing.

While the idea of a startup is romantic, the impressed reactions from casual onlookers mean nothing when you’re in the trenches trying to build something from nothing.

With a startup, we had no status, no influence, and no customers to start with. It’s an uncomfortable experience as everything goes out the door and you’re starting from scratch. Some days I was a door to door salesman pitching an unheard of company to skeptical businesses. Other days I was a customer service agent and courier for every customer order. All of a sudden I was doing tasks I would’ve thought were ‘beneath’ me while in the corporate world. Victories, no matter how small, are cherished. It’s an uncomfortable feeling to set aside years of status and ego.

Money Is A Thang

Money seems obvious, but it’s usually addressed in the context of money required for the business. Less discussed is not only the money just required to live, but also the lost wages from continuing on a corporate path. With a startup, lifestyles have to change and the uncertainty of future income is always a concern. While I made the decision early on to be prepared to spend money and forgo the monetary rewards of a corporate lifestyle, the pressure of income and lost wages consistently loomed in the background. While the burden and anxiety of towards money certainly isn’t fun, I was however required to value money more and learn to still spend, yet with a prioritized and frugal eye.

What’s Next?

Immediately, I wanted to capture my thoughts and learnings from the experience, which this site has enabled me to do.  Even in failure, there’s growth. I’m reminded of one of my favorite quotes, from Randy Pausch:

Experience is what you get when you didn’t get what you wanted

So now that I’ve done it – What did I learn? How will I look back at this time in the future? How has this changed me? I’ve captured much of the initial learnings, yet I suspect I’ll continue to see additional effects of my experience as time goes on.

I’ve been asked if I would do it again. I think doing a startup takes the alignment of several factors in life – family, finances, personal appetite, among others. I certainly would love to take all that I’ve learned and apply it to future endeavors. I still love the dream and thrill of creating something from nothing.

The startup has been an immense challenge that forced massive learning and growth. If there’s one takeaway for future endeavors – it would be to make sure that whatever I take on, I’ll continue to have the opportunity to not only have fun and learn, but to also be uncomfortable and fail.

** Edit: Since deciding to shut Mason Park down, I’ve joined Amazon as part of their International Retail team. It’s quite the change on so many dimensions, but I’m pretty excited to leverage all of my experiences towards a great opportunity for growth and contribution.