The Other Side of Entrepreneurship: Navigating Setbacks & Failures

Entrepreneurship is often made out to look like a highlight reel of overnight successes, even though failures are an essential part of the journey. But considering how low the lows can be, it’s understandable why sharing the setbacks we face along the way can be difficult. At times they can throw you off course, or in the worst case scenarios they can come at the cost of things that are invaluable.?

But on the other side, and over time, many of your setbacks will also have played a role in teaching you something. Or pushing, and maybe even dragging, you in a new direction. Take me for example. While I can still remember how bad different experiences have felt, I can now also appreciate what they’ve taught me, or how they forced me to take on different paths. Some for the better, some not, but ultimately all of which have led me to where I am now - not quite at the peak of where I hope to reach, but enjoying the climb, and able to create opportunities for others around me.

In this piece I’ve tried to share some setbacks from different stages of my journey as an entrepreneur, and what they’ve taught me. Hopefully, they’ll add to your own insights as you forge your own path:

Setbacks from early on (years 1-4):

Funny enough, one of the setbacks I had early on was experiencing success too soon. I launched a digital banner design company - BannersMall - as a solopreneur in 2003 and since there weren’t a lot of people in the space, I started doing really well. So well that I decided to make some real estate investments, including putting money down on a home for my family and a home to rent out. I felt pretty invincible at the time, and it didn’t help that I was all of 21 years old, without a ton of experience under my belt.

Then while running BannersMall, I worked with my brother on launching a computer shop around 2005. It seemed like a business we could grow, given how much demand there was. But we didn’t have the experience or knowledge to do that successfully. And there was so much competition that had launched before or around the same time as us.?

This led to a tough series of losses, both with the computer shop and BannersMall, as I lost customers while trying to juggle everything. By 2007, we had to let the shop go, and shortly after downsized to renting, ultimately selling both properties I’d invested in. On top of this, I had debt to reckon with and was facing criticism about how I’d been too ambitious from those in my extended family/social circles.

After regrouping, and with my family’s support, I turned my efforts to BannersMall with a few lessons in mind.

The takeaways: - Diversifying and generating more revenue streams only works when you’re diversifying in ways that you have the bandwidth for. Stretch yourself too thin and there’s a good chance you’ll wipe out.

- Part of the above is considering your competition, the size of the market and taking calculated risks based on all of that.?

- Your most vocal critics can be a blessing in disguise if you can tap into the desire to prove them wrong.

- One failure doesn’t have to determine your entire trajectory. To that end, neither do 10 or 100. Reflect, reset and launch again each time when you’re ready.

Setbacks while trying to expand (years 6-8)

As I tried to grow BannersMall it became clear that I had more clients than I could keep up with. I needed a team. And as I asked around I came to know that Southern India was a hub for tech and creative industries. So, I hopped on a plane and went off to Kerala to try out my luck. It took me around 2 months to find a solid hire, just when I was on the verge of turning back. From there, my first designer and then 2 additional team members worked in Kerala for nearly 10 months, before heading to Bangalore to follow some leads on more potential hires.

At the time visas only allowed me to be in India for short periods (ranging from 30 days to 2-3 months) and required me to be away for months in between. So I had to constantly be in a cycle of applying and reapplying to be able to see this path through.

Had it not been for the fact that my first few hires were some very solid team members, things could have fallen apart very easily. But in spite of the excellent work they did, and the momentum we started building, the stress did take its toll.?

Managing stress is one of the many things about entrepreneurship that you can’t be taught. You’ve got to experience it and find your footing within it. And I’ve definitely experienced it in many ways. In the early years, trekking back and forth between India and Canada, included difficulty sleeping, feeling anxious about whether things would come together, and a digestive disorder. This combination left me with less energy, made it difficult to focus and made travelling an unpredictable nightmare.?

Ultimately, though I was determined - and stubborn - enough to continue to see things through, it was also a wake-up call. If I wanted to build and grow a team, I was going to have to figure out how to tackle stress and prioritize my health, more effectively.?

The takeaways:

• Stress is inevitable - especially if you’re an entrepreneur. So finding as many ways as you can to manage it are some of the biggest keys to your success.?
• I started putting as much of my focus as I could into what was happening at present/in the near future and was within my control. Considering how much could change over time, I worked on limiting how much I planned down to the detail past a certain point.
• I became more careful with what I was eating and how much sleep I was getting, and over time my body bounced back.

Setbacks that led to a pivot (years 14-16)

After a great run, BannersMall and Doto, the design agency that our operations expanded to include, started hitting obstacles from around 2017 onward.?

BannersMall had essentially the same service model, with a few tweaks and website updates, since its start. But our share of the market and client base was dwindling down over time as competing services, with more innovative solutions, cropped up and picked up steam.

And by this time we’d come to specialize in services for one niche at Doto (real estate and development), and this in turn made things volatile when clients hit roadblocks all at once due to the market.??

While we dealt with a financial crunch, we still had bills to pay with the physical footprint of an office space, a team of full-time employees and a pivot to figure out. After months of trying to figure out and implement steps, many of which crashed and burned, our new subscription-based design service finally took off (KIMP).

The takeaways:?

• It’s not over til it’s over. There will be many times when you feel like you’ve gotten knocked to the ground as an entrepreneur. As long as you can get up again, you’ll find a way to pivot or take an alternative approach.?
• One of the blessings in disguise with setbacks and failures is that it’ll truly show you who’s got your back, even when you’re down. There will always be a lot of fanfare when things are looking up, but the team members that stand by you when you’re down are worth their weight in gold.
• Innovate or get left behind. There are very few industries which don’t undergo changes and require service providers to adapt accordingly. If you’re not keeping up with competitors and clients, there’s a good chance that you’ll be left behind as well. And let me tell you, no matter how stressful or even impossible it may seem to branch out in what you’re doing - it’s a 100X harder to play catch up once it becomes clear that you have to.

Setbacks in a global pandemic (year 17)

Just past the year mark at KIMP, we were thinking about scaling our team and operations. And then the Covid-19 pandemic struck.?

We had just recently completed a trip to Sri Lanka where we’d done some hiring and scoped out an office space to serve as our hub there. After things finally lined up in one location, they suddenly fell through a few weeks before the full impact of Covid-19 became clear.

Then by the end of March, the office space where most of our team had been working from had to shut down. We had to scramble to set up workflows for everyone to be able to continue working from home as the first of many lockdowns was about to take effect.

The height of the pandemic was horrible. There’s no two ways about that. We lost a beloved team member, many team members got sick and were caring for loved ones who contracted the illness, and it was difficult to maintain a sense of connection, forcing everyone to continue working with varying degrees of isolation.?

But in the aftermath, as things slowly started to find a semblance of normalcy, there were some silver linings. The pandemic had forced our operations to go entirely remote. And with that we managed to expand, and create job opportunities, in new regions like Sri Lanka with the remote workflows we had to set up due to the lockdowns. Many of our team members stepped up to help one another, and our clients, adapt to working, and collaborating remotely.

And many of our clients stuck with us through all the uncertainty, leaning on us to help keep their workflows going.?

The takeaways:

• You cannot prepare for every possible scenario. Sometimes things will just go wrong without any rhyme or reason. All you can do is keep taking the next most strategic step, and the next one after that.
• There’s always more ways to reach a destination than the one or two that you may be aware of. When one door closes, try to see if there’s a window or back door open. There might just be an alternate route waiting for you, if you would just step away from Plan A.

Besides the specific takeaways I’ve tried to highlight above, there are a few other things I hope you’ll take away from this piece:

1) Don’t try to avoid setbacks and failing. They’re necessary parts of your journey and you’re only hindering yourself, and your team, if you try to avoid them. They teach you your current limits and help you find your way forward. They hurt, no doubt. But they’re a lot less painful when you and your team face them head-on.

2) Whenever possible try to share the experiences of your setbacks and failures with your team to normalize them and to help foster a culture in which you can share these experiences and find ways forward together.

3) Your support system is crucial. So be mindful of who you lean on. Whether that be your immediate family as in my case, or friends, colleagues or mentors. Being an entrepreneur can be very isolating at times, and will force you to regularly have to dig deep to find your why. This is true even when you have a team, investors, and more. When you’re pulling yourself back up after the millionth time of being knocked down, and you’re second-guessing yourself and your ideas, the faith and support of the people who see the best in you, even when you can’t, will help you keep putting one foot in front of the other.????

4) Everything has the potential to compound; this includes your setbacks and failures, if you don’t take the opportunities to reflect and learn that they can create. That choice will always be yours.