Managing Fear And Failure With Your Startup

Being a part of the startup community has been an absolute gift. I have been blessed with the opportunity to build Swaag with two amazing people, and have surrounded myself with some of the smartest experts in product, UX, design, user acquisition and customer development.

As lucky as I have been in this community, the fact remains that three of four venture-backed startups are unable to return investors’ capital. Even worse, only 1 in 100 companies receive funding, and of those, 1 in 100 succeed.

The brutal reality is that as smart as you are and as good as your network and product may be, the odds are you are going to fail. Failure may be inevitable, but it is not something to fear.


Fear is constant. Vinod Khosla, founder of Khosla Ventures, put this into a great business context when he said, “Startups deal with unknown products that solve unknown problems at an unknown price point for a largely unpredictable customer. What could go wrong?” 

Instead of pretending like you are not scared, embrace it. Use that fear to motivate you, not cripple you. Rahul Varshneya, entrepreneur and startup coach extraordinaire does a great job of outlining a strong plan for overcoming fear. I have adapted his framework and developed three simple steps:

Dive in! – Tackle the task at hand with a sober, pragmatic attitude. I learned what I was good at, and what I sucked at. For a startup to succeed, you need to be excellent at everything you can control and everything that you’re good at. But you can’t do it by yourself, so surround yourself with talented people who make up for your weaknesses

Put a face to fear. – Fear is a powerful, consuming emotion. It often dominates your decision-making, including taking risks. Instead of being swallowed by fear, put a detailed face to. Determine a few, very specific things that you are worried about, and write them down. My fear was that my company would not be able to accomplish everything we wanted to with the money we had raised.

Plan and source. – After accomplishing steps 1 and 2, you have identified what your strengths and weaknesses as well as what worries you. So how will you take action? This is actually the really fun part! Make a variety of plans, but expect that most will fail. Be relentlessly prepared. Create ten scenarios and ten plans of attack.


One of every two things we tried for Swaag did not work. Whether it was user acquisition, PR or partnerships. The delta between expectations and reality was consistently wide. But with every failure, we learned more. It has been our greatest educational tool for the business.

The framework I use to overcome failure is pretty simple.

1. Make a hypothesis
2. Understand the tools you have at your disposal (talent, resources, relationships, guidance)
3. Make a plan
4. Execute
5. Fail, and understand why you failed
6. Rinse and repeat

Do not forget that some of the greatest businesses of today were at some point on the brink of failure; AirBnB, Blogger, Rovio and FedEx, just to name a few.


Peter is the Founder and CEO of Swaag, a mobile community focused on street wear and sneakers. He’s an entrepreneur with a passion for mobile, ecommerce, building things, sneakers, and running. Say hello to him on Twitter @chunp.