When to Walk Away — Lessons from Running a Startup for 4 Years

Our first product shoot in New York, Aug 2014

Even after trying very hard, for a long period of time, sometimes stopping is the best course of action.

After making the gut-wrenchingly difficult decision to step away from my company Popinjay after 4 years, there is a lot to reflect on and share.

I wrote this post for two reasons.

1. To speak to Popinjay’s customers & cheerleaders and answer their questions. Popinjay has always prided itself on its transparency, and this decision is no different
2. To share lessons with the startup community at large — particularly first-time entrepreneurs

The Big Picture

Here they are, upfront, the 4 most critical reasons I made this decision.

1. My Startup Philosophy - ‘Go Big or Go Home’

This isn’t the right approach for everyone, but it is what works best for me — keeps me challenged, fuels my ambition, and helps me perform to my fullest.

I started Popinjay with the vision for it to be a $100M+ company. When I made the decision to step away from Popinjay, we did not have to stop. We had not run out of cash, and stopping was not the only recourse. However, the speed of growth and scale of operation that I feel inspired by had started feeling out of reach, and required raising capital that was several orders of magnitude higher than what we had access to.

2. We Didn’t Get Fundraising Right

Getting funding right meant raising the right amounts, at the right time, and from the right people. I struggled on all three accounts.

I raised a total of a half million dollars in seed funding — roughly half of this was raised in the initial seed round, and the rest as follow-on funding 1.5 years later. The initial seed did allow us — within the first 12 months — to design and manufacture an exceptional product, build a robust supply chain, hire our first 3–4 team members, land our first big retail partnerships (Anthropologie), get our first global press (CNN), and be carried/seen at our first celebrity-studded event (the Emmy Awards).

But amidst the initial frenzy of unexpectedly fast growth (we ran out of stock in our 8th month) and a lack of consensus among the early investors on the right time to re-raise (‘let’s get a bit bigger first’), I waited too long to raise our next round. Ultimately, we fell prey to the notorious chasm between Seed and Series A. Popinjay was still early for venture capital, but too advanced for smaller seed and pre-seed investors with ticket sizes we had already raised.

Note: I feel this is a crucial topic for entrepreneurs, and plan to write a separate post on my fundraising learnings in the coming weeks.

3. Going Solo Was a Deal-Breaker

Startups, particularly those with bigger ambitions, are too much work for one person, in the early days. It’s as simple as that.

In Popinjay’s case, add to that the complication of a physical product (vs. a service), a complicated supply chain spanning multiple countries, teams in two different parts of the globe (Pakistan & US), a vertically integrated business that owned everything — from design, to manufacturing, to marketing & sales —and a saturated, hyper-competitive and often-fickle industry (fashion), and it became impossible to go solo as we scaled up and the stakes got higher.

Most importantly, it severely hampered my ability to effectively fundraise and recruit talent — two things no startup can scale without, ever. Ultimately everything suffered because of not having a co-founder. In retrospect, I would heavily prioritize getting the right co-founder(s) on board, and even delay execution for this.

4. Timing Matters When Pulling the Plug

There is a right time and a wrong time to step away from your startup.

It takes 7–10 years to build something at scale, so you have to be committed to doing the time, and can’t fall into doubt as soon as the going gets tough (which it will — this is unavoidable). At the same time, you have to stay honest and realistic about the future, and regularly assess whether your progress is still aligned with your original vision.

To some of Popinjay’s investors, it felt like a strange time for me to consider stepping away. We had recently received multiple new funding commitments, had an organized PR plan for the first time, our new Creative Director had recently moved countries to join us, and we had secured new sales partnerships in East Asia.

But I also knew that we needed much, much more to truly go big. We needed tens of millions, not hundreds of thousands in funding, and I wanted Popinjay to truly thrive, not survive.

I feel grateful that ultimately this was my decision — not that of the investors, team or market, and not the result of an unavoidable circumstance. It was the result of deliberation, self-awareness and brutal honesty. It was the output of a desire to walk away when there was still value in what the brand had created, versus squeezing it hollow, and leaving because there was no other option left.

On Ego, Fear & Guilt

Deliberating on this decision was emotionally and mentally taxing for me in ways that even running the startup hadn’t been.

I had to overcome fear, doubt, guilt, and ego. It took a Herculean effort to be honest with myself. To ask myself the right questions and to answer truthfully. It required removing emotions from the equation. It required letting go — something I am not good at.

There were endless conversations with teammates, investors, board members, mentors, and customers. It’s hard to explain how tough it was to think about moving on from what had become synonymous with my name (“Oh you’re the Popinjay girl.” or “Hey, you’re Saba Gul Popinjay!”). In my head, my own identity was inextricably linked to Popinjay. I had lived, breathed, dreamt it for so many years. I had quit my job in the US and moved to Pakistan for it. I had pushed every single boundary for it — physical, emotional, mental, health, relationships, financial. How could I stop?

Making this decision required courage and conviction, particularly because there wasn’t consensus among the investors at first.

It required recognizing that I was more than my startup.

How Do You Know It’s Time to Stop?

This was the million dollar question I had to ask myself — and get right. Was it just a crisis of confidence or something more?

As a founder, your risk tolerance and persistence can keep you from seeing things clearly. How do you balance seeking criticism with weeding out the noise and the haters?

Two tell-tale signs that helped me:

1. You cross over from persistence to stubbornness.

Persistence is necessary for success, and stubbornness is a roadblock to it. I knew some introspection was in order when I started feeling I had crossed over from one to the other.

The challenge is judging when you’ve done that. How do you know?

For me, a big part of it was trusting my own gut on this (versus going by others’ intuition, which I had often done). Paying attention to that deep-down feeling, that voice in your head, that says ‘you know what to do.’

The other part was listening. Listening in particular to advisors that encouraged me to regularly take stock of my startup, to ask the right questions and stay honest, to have a time boundedness to anything I tried, and to think about the opportunity cost of my time. It meant paying attention to reactions, results, metrics, feedback, patterns and trends.

2. You start running around in circles, solving the same problems

The second tell-tale sign that it might be time to stop is that you find yourself butting heads with the same problems over and over.

I still remember the moment in Pejman Nozad’s Bay Area office, when he asked me where I wanted to be in 1 year, prompting me to go home that evening and make a list of Popinjay’s 1-yr goals. And then — the feeling of dread when I looked back at my list 12 months later.

While it’s more common than not for startups to miss their goals, and things always take longer than expected, I realized I was grappling with some of the same fundamental issues in the business, and asking myself the same questions today as I was ~2 years ago.

So, How Do I Feel?

This is the question every person I shared the news with asked me.

Letting go of something I had given my heart, blood, sweat & tears to for 4+ years, that I had sacrificed my health, relationships, and well-being for, is no doubt very difficult.

I was devastated at first. This journey had given me some of the best relationships, experiences and learnings of my life. There was a sense of loss.

Thinking of myself the person, and Popinjay my company as two distinct entities helped. Below are some of the things I feel as I reflect on this decision:

1. I feel fiercely proud of what I built. At first, this decision brought guilt — of disappointing my artisans, team, and customers. I felt fear — of how the decision will be perceived, how I will let go & what I’ll do next. I even felt shame — so many young people look up to what I’ve built; will I be breaking their hearts? But I now fully appreciate the beauty of what I was able to build with Popinjay and recognize that it made an everlasting difference to thousands. I am reminded of it by my artisans, customers and teammates, all of whom Popinjay impacted in exceptional ways. For our customers across the globe, Popinjay will live on in their hearts and on their arms as they continue to carry our products (and pass them on to their daughters, as many have told me they plan to). I feel proud because I know I did not arrive at this crossroads for want of trying, for lack of hard work, or for a lack of persistence or commitment.
2. I learned to be imperfect & became truly fearless. I am a perfectionist. And there is no better way to get over perfectionism, than being imperfect. My friends thought I was fearless when I quit my job in the US, and got on a plane to Pakistan on the promise of an idea. But it’s when you pull the plug on your work of several years that you actually let go of fear.
3. I am walking away with the lessons of a lifetime. This is something I am immensely grateful for. This blogpost is testament to the learning. In 4 short years, I learned so much, about so much. Everyday, I had to reinvent myself, tackle new challenges, tread new paths, and accomplish new things I was completely unqualified for. The person I was in 2014 is not the person I am today. My objectives, inspirations and world view has changed, fueled by the chaotic experience of building a startup. Maybe that’s why VCs love funding serial entrepreneurs. The battle scars make for a very, very thick skin. The lessons learned along the way are invaluable.
4. Popinjay gave me some of my most meaningful relationships. From our artisan women who taught me about resilience, hard work and an indomitable spirit, to customers who showed me what it means to be kind, generous and live your values, to my team that regularly surprised me with their motivation and obsession for creating change, Popinjay gave me friends that I will cherish for life. It made people reach out to me, get vulnerable with me, and extend offers of time, money, expertise to me.
5. I learned to trust my own gut. As a first time entrepreneur, I had a tendency to take advice — particularly my board’s — very seriously. They’ve successfully built & scaled businesses, I would think. They must be right. But the truth is, every business is unique, and you’re the one closest to your business, not your investors or board. No one can really tell you what to do. There’s no playbook you can follow, and no mentor you can always rely on. You have to figure it out yourself as you go. On my investors’ advice, I did many things I shouldn’t have, especially in the early days. I waited too long to re-raise (“let’s hit some bigger milestones first”), tried to bootstrap, tried to switch market focus, tried to hire the wrong people, tried to go too long without paying myself. And ultimately, I learned to trust my own gut.
6. I can never be anything but an entrepreneur. Popinjay taught me how much I enjoy building things that create positive impact. I associate deeply with startup communities everywhere, and now have a better understanding of what they need to thrive. I will always be committed to advancing entrepreneurship and championing ideas that create impact for our world.

The Biggest Lessons — Professional

1. Don’t go solo. Find a co-founder, even if it means waiting to execute.
2. Get fundraising right — right timing, right amount, from the right investors
3. Invest in people. You can never spend too much time on this
4. Watch for that fine line between persistence and stubbornness.
5. Taking too much advice can kill you too. Trust your own gut before that of others’
6. Plan around your business’ weaknesses

The Biggest Lessons — Personal

1. Your home run may not come the first time you try something. Entrepreneurship is a life long journey.
2. You are more than your startup. Don’t get too emotionally attached to your startup. The lines between the founder and the company should stay distinct.
3. Take care of yourself during the journey. It’s a long road.
4. Ask for help. People’s generosity will surprise you.
5. Listen.
6. Nothing is in vain.

Popinjays Dotted Around the World

Popinjay existed and touched lives because of everyone that ever bought a product from us, worked for us, invested in us, or even just cheered us on from the sidelines. Thank you from the bottom of my heart.

Recently, a loyal Popinjay customer, Salma Hasan Ali, ran into one of our brand ambassadors in New Jersey. Two women that were complete strangers started a conversation because each recognized the Popinjay bag the other was carrying. Salma wrote to me:

“Popinjays, dotted around the world, will continue to connect.”

That is more than I had hoped for, or dreamt of when I started Popinjay. I know our mission will live on through our customers as they continue to carry their Popinjay products with love and pride.

What Am I Doing Next?

While I don’t yet know the exact problem I’ll work on next (though I do have lots of ideas!), I know that I will continue to build things that solve big problems and create impact. I am particularly excited about solving problems with regional relevance to Pakistan (where I live), Asia Pacific, & the Middle East.

If you’re cooking up the next big idea for this region, and looking to find partners, get in touch!

Meanwhile, I will continue to share updates on the future of the brand itself, as and when they become available.

Our website www.popinjay.co will stay operational and we will continue to ship for now.

More where this came from

This story is published in Noteworthy, where thousands come every day to learn about the people & ideas shaping the products we love.

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