Ever wonder if you should keep running your business or just shut down? When you invest months, possibly years into your business and things are not quite working, it is beyond frustrating. This may cause you to wonder, if I keep going and just make a few changes, will it all turn around or is this a lost cause?  

As an entrepreneur, one of the most difficult decisions you may face is whether to close your business and give up on your dream or keep pushing forward despite an uncertain future. 

Many entrepreneurs have come face-to-face with this gut-wrenching dilemma. On my podcast–  Unmessable— Manny Medina, founder of Outreach.io, a company that’s raised $250 Million and currently employs 350 people, shared his approach on how he decided to double-down on the business after three years of failing to reach product/market fit.

[Listen to full episode here]

Although you can never really be certain of the best course of action, there are early signs when you make the pivot that can signal whether you’re heading in the right direction. Knowing what to look for will give you the insight required to make an educated decision about your next step. 

Here’s the process Medina followed to figure out he should go all into Outreach.io:

Collect lessons learned up until now.

What worked? What didn’t? Was the product over engineered? Did you invest too much money in marketing before you nailed your product/market fit? Is the business model attractive? What part of the product or service did people use most?

Do a deep dive of your analytics to see if there are any anomalies that surface. When you are in the throes of things, gaining perspective can be a challenge, but doing this exercise may help you uncover important information.

Compile a list of hard assets and evaluate whether they have value.

You’ve been at it for months or even years and you have built a bunch of stuff. Inventory all your assets and see whether they have value. Doing this could be a jumping-off point toward a new company direction. 

Listen to your customers. 

Medina, while on sales calls, would repeatedly hear that potential customers didn’t want to use their core recruiting service, but loved a side feature that helped with outreach toward potential candidates. He could have brushed that off, but he listened, and in doing so felt inspired to double-down and spin-off a side feature into his business’s core product. Without this key insight from the very people he was trying to sell to, Medina may have never been able to pivot the way he did or generate millions in revenue later down the line. 

Run through a cost/benefit analysis to help ground you.

Doing a cost/benefit analysis exercise will help you evaluate your options. At this point, you are probably getting a miserable salary (if any at all) and you need to see if continuing to invest your time in this venture is something feasible for you. Go over cost/benefit analysis of what you are foregoing by shutting down and what the alternatives are. If moving forward with your business just isn’t in the cards, you can begin to make peace with this. Alternatively, if the idea of working for someone else or starting over is just not something you want to do, that’s fine, but at least you approached the decision methodically. 

Are you excited enough to keep going? 

This is a critical point because, after a lot of failing, you likely will be demoralized. When that happens, your energy is low, your conviction is gone and you might as well shut down. But if you and your cofounders (if you have some) are aligned and onboard, it’s game time. That’s what happened to Medina. 

While at the Techcrunch Awards, it dawned on him that the side feature could become the core offering of their product, but at this point, the company was in such a cash crunch that they were inventorying computers and selling them to be able to pay outstanding bills. He knew that doing yet another pivot would require his co-founders to be fully onboard and share his new vision for the company. As he stepped outside to call his co-founders, he gave the pitch of his life and managed to get everyone reinvigorated with passion, and eager to try this one last effort before throwing in the towel. And it paid off…big time. This newfound drive led him to build Outreach toward hyper-growth where the business has been growing over 100 percent year-over-year. 

While the path to this was anything but easy, and one riddled with uncertainty and self-doubt, it’s often a rite of passage for entrepreneurs, and one you need to be prepared when you cross that bridge.  

[Listen to full episode here]