What Keeps Startup Founders Up at Night?

Founding and launching a startup is an incredibly stressful venture, even in the best of circumstances. Startup founders have a million things to worry about, a million more to plan, and the ever-present threat of failure hanging over their heads.

As a startup grows, the pressure doesn’t lessen, but it does change as priorities and business needs shift. With each stage of growth, founders have different concerns and challenges to face. Here’s how to face your biggest worries as a founder and overcome the toughest startup challenges.

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Stage 1

In the early stage of every startup, founders stay up at night worrying about finding the right product-market fit. Does your product solve a real, painful problem, and are there enough people with this pain? If the answer is yes to those two questions, you can almost always build a product that solves this pain, and find a market of customers who want to buy it. If you answer no to one of those questions, no matter what you build, it’s just not going to become a sustainable business.

A bad product-market fit is a potentially company-ending difficulty, and is every founder’s number one concern at this stage. In order to really assess the market, you have to constantly speak with your existing customers and get to know their pain. If you find out your product doesn’t exactly address their needs, you need to learn from your failure and quickly pivot to try new ideas. Then you have to reevaluate your product-market fit yet again. But once you find a concept and a market, you will be able to build a product, raise capital, hire people for your team and – most importantly – successfully sell your product.

Stage 2

This is the middle stage for most startups, where you’ve gotten series A funding and started scaling. At this stage, founders are mostly concerned about sustainable growth – going from selling your product to maybe 10 customers to reaching more than 100 customers and beyond. It’s also about growing your team from the core team of maybe 10 people to hiring a large number of new employees. In this phase, cash flow becomes your biggest worry. You’re trying to build a selling machine – but how do you do so effectively and without running out of funds?

There’s a danger that if you go out today and hire 40 new sales reps at once, you won’t have enough leads to keep them busy and your cash burn rate is going through the roof. But conversely, if you don’t hire enough new reps, you won’t make enough revenue to grow quickly. It’s a careful balance between managing the growth in proportion to the cash you have left – you need to grow fast, but you don’t want to grow too fast. The problem is, that balance point between the two is a moving target and you have to continuously reevaluate it as you grow.

Stage 3

In the final stage, you’re well-funded, you have predictable revenue and have found a repeatable sales and marketing process that works for your business. Now, you just have to make sure it continues running smoothly, making minor adjustments along the way and continuing to scale. The danger with this last stage, however, is losing your company’s identity and culture in the process of building the business. In this stage, founders worry the most about maintaining the culture and drive that made the business a success in the first place. You don’t want to have intense political factions developing, like a bad dynamic between marketing and sales, for example.

Founders are constantly tweaking and adjusting the business’ culture in small ways, but as the company grows to more than 100 employees, founders simply cannot control every aspect of the company anymore in this way. The key to maintaining the ideal culture is hiring great people early on who also strongly value the company’s identity, and can act as ambassadors. It decentralizes the effort, so you don’t have to worry that new hires won’t be a culture fit or will change how things are run. You can trust that the business you’ve built will continue to succeed, rather than sink under it’s own weight.


Worry is an unavoidable and necessary part of founding a startup, and as you move through the stages of startup growth, you will see changing priorities and changing concerns. First you’ll worry about your business plan, then you’ll worry about growth, then you’ll worry about culture. But as long as you are aware of these pitfalls and make plans to address them, you’ll see your startup succeed.

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