These signs mean it’s time to let go of your startup (but moving on is never easy)

“Hey John, it is good seeing you on social media and how your company X has progressed thus far these few months,” I said encouragingly during a regular meetup with an entrepreneur I had mentored for a year.

John (not his real name) had posted about the developments of his company on social media and had recently raised a good seed round with quality VCs.

“Yes, but I have something more exciting for you,” he smiled. “I got a new idea which I am thinking of starting off with some new co-founders. Do you think I can get funded on this?”

My face turned grim. “What do you mean new idea with new co-founders? Aren’t you moving along with your company and getting ready to grow it with your new funding?”

John shrugged and sighed, “It is just not the thing I am excited about anymore,” he said. After I prodded him gently, John began to share the struggle he faced. He no longer believed in the product he had set out to create. The product had become a commercially viable and scalable one, but the transition was not what he expected. He clashed often with his co-founder-who was also the CEO of the company-and dreaded going to work. He was even bothered by how “the new hire that just joined the team walks strangely.”

Not all is good like what the news reports

In the last six years, I have mentored many entrepreneurs, some of whom I have kept up with on a regular basis. But recently, more entrepreneurs like John have been asking me whether they should continue with their respective startups or not. Some act as if everything is fine, but are actually in denial that they want to quit or close down the business.

Despite posting about their expansion plans on social media and looking excited on the outside, they are actually demoralized internally. The spark and honeymoon period have gone away and reality has sunk in, where building a company and getting back returns has become an obligation more than anything else.

Signals that you might be wavering

So what are the signs that you might be wavering? Here are some of the stories that have been shared by entrepreneurs.

A business is going faster than you can keep up

One entrepreneur was passionate about his SaaS product and expanded his business to two other countries. As the business grew, he found himself trying to learn new aspects of managing a group-level business. However, he lost his first love, which was to build his product and give personalized customer service to his clients.

Things got messy, and he hired a CEO to manage the company operations. Despite the company being profitable and growing, the entrepreneur felt lost in strategic planning and finally exited his company. He shared that he was not a natural leader and had found the business growing too fast for him to keep up.

Sometimes, we have to consider whether we are able to handle the onslaught of growth in a business. Many may eagerly embrace the challenge, but it takes a toll on others and affects their ability to perform.

Are you losing your family and yourself?

Have you been neglecting your loved ones-the foundation and purpose of what you do?

Some entrepreneurs can juggle both family and work well. In fact, I have seen loved ones who have been very encouraging. However, there are those who struggle.

A man in his 40s shared how he built his business at the expense of his marriage-his wife had walked out on him, taking his only daughter along. Even though he is now a successful man, he wishes time could be reversed so he could choose his family over his business.

Is the business going anywhere?

Is your business going the way you expected it? Or has it stalled or lost steam?

During our pay-it-forward days, I have advised and helped over 1,600 startups in 1-to-1 advisories. Yes, there were those we were proud of that raised follow-on rounds and are now growing, but there were also businesses that weren’t going in a specific direction. We had to be frank with the founders and we encouraged them to move on and take what they’d learned from this valuable experience forward.

Is working in the company an obligation rather than a vision or a passion?

Are you passionate about the business you run? Or are you just feeling obliged to run it?

F&B entrepreneur Jay (not her real name) and her co-founder came together to set up a patisserie, but both had different opinions on what products should be made. Eventually, Jay gave in to her partner who created the products while she ran the operational aspects of the business, which was not her forte.

She felt miserable, but she had given her promise and had committed her money. She was continuing out of obligation and her passion had been lost. If you met her, you could sense a sadness around her.

Is your mind wandering off to do other things?

I have seen entrepreneurs who are part of a successful team and are growing a good startup. But like John, these entrepreneurs inform me of new ventures and startup ideas they’ve had. I find it a common occurrence now that entrepreneurs tend not to focus on one startup but want to be involved in multiple ones at the same time.

While entrepreneurs find they can juggle a few startups, it is not healthy, as sacrifices will be made. It may be fine if you owned each startup fully, but it is different if there are other shareholders involved. VCs are also very wary of multiple startup entrepreneurs, who are part-time in one startup and part-time in another. It gets confusing and interests misalign.

Removing emotions and making the right decision

Quitting a startup is a decision which should only be considered when other options have been exhausted. Usually, if it is a business viability problem, I encourage the founders to pivot. If it is a founder related issue, it is best to find common ground to resolve matters.

But even when they’ve made the decision to let go, it is emotionally tough to do it. Speaking as someone who’s had to shut down my businesses, it does not get any easier.

Many startup entrepreneurs have become associated with the startup brand they’ve built. They have branded themselves with their posts on social media and by wearing their company t-shirts on a daily basis. It is not easy to give it all up.

Entrepreneurs may also feel obligated to their fellow founders, team members, clients, partners, and investors who have placed their faith into the startup. The pressure to face the music can be intense and horrible when you decide to break the news.

Ending thoughts

Leaving a startup is not an easy topic to talk about, especially when much has been invested. Most importantly, entrepreneurs have to recognize the signs that things are not working out, and they must remain positive as one chapter of life closes and new opportunities open up the next.

This is the fifteenth article of the “This article first appeared on Tech in Asia. Startup Advisory Clinic” series.

Originally published at on February 24, 2017.


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