Making It Through The Startup ‘Trough Of Sorrow’

August 20, 2015

“The Struggle is where greatness comes from.” Ben Horowitz


Startups are hard, but they’re especially hard when things don’t go as planned. And that’s not a distant possibility, no matter how strong of a product/market fit you have. It’s a foregone conclusion that something will go wrong at some point.


That deep period of malaise that can sometimes follow a significant setback, at a time when you most need to be focused, has been described in a few different ways. As seen above, Ben Horowitz called it, “The struggle,” while Y Combinator’s Paul Graham called it the “trough of sorrow” (which the excellent StartUp podcast discusses in its season about Dating Ring). One of our mentors calls it “falling off the startup momentum train.”


Pixlee-visual-marketing-platform-ecommerce


Paul Graham’s Trough of Sorrow


It doesn’t matter how much you’ve fundraised. Getting back on the momentum train after you’ve suffered a setback, like the loss of key team members or the realization that your target customers aren’t satisfied with the current iteration of a product that you’ve spent months developing, can be difficult and demoralizing. While a lot of founders have written about the struggles they face, not enough have described how to climb out of the trough of sorrow and move forward..


Here are some thoughts on that, based on my experiences and stories I’ve heard from other entrepreneurs and investors.


1. Try to maintain a financial buffer to weather a storm


As one of our investors once told me, as long as you stay in the game you still have a chance to win. And you can stay in the game as long as you have money.


For startups, cash is oxygen and you need to be disciplined in how you use it. It’s important to focus spending on what’s critical and find ways to extend your runway, especially during difficult times. Spending more cash won’t solve all of your problems ; often hard work and time are required. For example, time is the main requirement when you’re exploring new ideas or waiting for your market to mature. But having cash on-hand can buy you time.


Satya Patel, a partner at Homebrew.vc, put it well in a blog post when he wrote, “Many times the key to winning is just surviving so that market timing finally lines up with your product or service.”


Of course, there’s a  chance  your market will never take off, but sometimes, over time, a unique opportunity you couldn’t have foreseen will materialize. For example, before Lyft was a billion-dollar ride sharing app, the founders spent five years working on Zimride, a carpooling service designed to help college students share rides back to their homes during the holidays. They eventually pivoted their idea, and as smartphones and the sharing economy took off, so did Lyft’s service.


2. Focus and figure out what your company is uniquely good


Getting through the trough of sorrow doesn’t always require you to do more; often you need to do fewer things, but do them well. One of the most common ways that startups fail is by trying to do too much at once.


At Pixlee, we have an internal saying that a confused buyer will not buy. Customers want to know what value you will provide; thus, having a crisp and singular value proposition that resonates with a customer pain point is incredibly important.


The reason zeroing in on a unique value proposition  is difficult for many entrepreneurs is because it requires you to say no to a lot of appealing opportunities, potential customers and features they want to build. For some entrepreneurs, who spend almost all their waking hours thinking about what their company can be, that can feel like a painful loss. These are opportunities you may have included in your investor pitch deck, but the reality is that without having a focus, it’s going to be extremely difficult to differentiate yourself from the pack.


Having a product that does a lot of things but doesn’t do anything well is useless.  Your goal should be to definitively say that your product is the best  at doing X for market Y. You should ask yourself, “Which customers do I care most about, and what can I do to make their experience better?”


3. Don’t get panicked into a pivot


While there are many successful companies that pivoted, making it through a slump doesn’t always require changing your strategy. Sometimes you just need to roll up your sleeves, get your hands dirty and execute.  There are many factors that go into the fight-or-flight decision, but if you choose the former, you need to be prepared to win a series of small battles through hand-to-hand combat.


Having everyone do his or her job well can be the best recipe for success. Amazing things can happen when the founders set a clear direction, the sales and marketing team hits its numbers, the engineering team hits its deadlines, and the customer support team goes above and beyond the call of duty. If you put together a few good weeks, those weeks can turn into months, and a few good months can turn into quarters. You’d be surprised how quickly you can find yourself back on the momentum train, and you’ll be stronger for having fallen off it.


Making it through the trough of sorrow isn’t rocket science; it’s just about continuing to run your company in a smart and strategic way. What’s hard about it — incredibly hard — is picking yourself back up when your spirits are down. But it can ultimately make your company more innovative  because it forces you to be focused and develop good practices.


You should never hope to experience the trough of sorrow, but if you make it through, you’ll undoubtedly be a better company. And you personally will be a better entrepreneur.

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