I Failed with 2 Startups in 1 Year… And I’d Do It Again

Daniel Tracey Holloran
The Startup
Published in
4 min readDec 4, 2017

Anybody who’s ever worked with a startup knows the risks associated with it. It’s a dog-eat-dog world when you’re trying to create a product or service that has never been seen before. You have no idea who will buy it, if they’ll buy it, or where you should be selling it. All while convincing people to buy a product or service that has never been built, you have to compete in a global market with large competitors who can outspend you at every corner. It can be overwhelming, scary, exciting, and dang fun! I worked at two startups in the past year which both ran out of funding and I loved every second of it. I wanted to share some insights into what you’ll be feeling, some of the things I learned along the way, and how I became a better, more positive person because of it.

Step 1: Misbelief & Surprise

If you’ve ever been laid off, you’ve experienced this feeling. Before you feel any type of anger, confusion, or do I daresay — happiness (depending on your situation), the first thing you’ll feel is surprise. You’ll be surprised that, starting tomorrow, you no longer have a job. You’ll feel shocked that you’ve seen your co-workers day in and day out, but now you don’t know the next time you’ll see them. It was this latter realization that led me to the first lesson I learned.

Lesson 1 — As your shock wears down, you can offset a number of your initial concerns by focusing on the positives. I realized quickly how much I had enjoyed my career because of the people I worked with. I made sure to say a heartfelt goodbye and also made a valiant effort to get contact information, etc. so we could stay connected. More than ever I felt that life is made by the people in it, not by what you do.

Step 2: Fear and Uncertainty

I’m only 25 years old and have worked pretty much paycheck to paycheck my whole career. So, needless to say, I faced a lot of fear and uncertainty. At a time in my career where I needed to be building confidence and job skills, I had been out of work twice due to a company’s bank account running dry. I would assume this step is a little easier with more financial security, but I know it will always be the hardest part. You don’t know where or when you will find your next source of income and you don’t know if you will enjoy what you do. Just make sure that you don’t let the fear and uncertainty cripple you from moving forward.

Lesson 2 — Use fear and uncertainty as a tool. You’ll find out how strong you really are when your back is up against a wall. I felt scared in this situation even as a young man but if I had a family to support, I know my drive would’ve been even greater. You learn the most about yourself and your strengths during this phase. Use this time for introspection to help you figure out how to leverage your interests and skills to move toward your next opportunity.

Step 3: Belief & Pride

Yes! We’ve made it to the best part of the whole thing! After being shocked and scared, you are slowly finding yourself. You have done some introspection and discovered the best aspects of your past experiences and are building confidence in yourself. You begin to feel proud of yourself for attempting something new and you believe in yourself more than ever before because of your efforts. The lessons you’ve learned and the people you’ve met throughout the process give you peace of mind and make you smile. Now, use everything you’ve learned and all of the confidence you’ve gained to keep moving forward!

Lesson 3 — Be patient, do something you love, and enjoy the journey. This experience has shown me that happiness does not come from money or job security but in constantly pursuing something you love. I know it’s cliché, but I would rather have failed at two startups with great people doing something I enjoy, than succeeded at a startup with awful people doing something I hated. Don’t search for success, search for happiness.

Everybody Should Work in a Startup At Least Once

I know, I know… Everybody says this about every industry. But I’m not talking about career development and networking and all that jazz. I’m talking about finding yourself. I’m a firm believer that struggle makes muscle. A slab of stone must be chipped and chiseled before it becomes a resounding statue. My journey helped me to trust my intuition, discover what I like, discover what I’m good at, and l got to collaborate with a whole lot of great people along the way. Without failure, there cannot be success. Trust yourself to go out and fail, at least once.

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Daniel Tracey Holloran
The Startup

Writer, Storyteller. Content & Product Marketer creating a better world, one word at a time! @DanHolloran