Get All Access for $5/mo

How I Transformed My Business Failures Into Strengths I can't regret the handful of companies I've launched that have fallen dead flat, because each taught me something.

By Matt Cimaglia Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.

Rocco Ceselin

Every challenge exists for a reason. And while the challenges will be different for each of us, their core purpose is fundamentally the same: When we are faced with a difficult challenge, we must learn from it and flip it into a strength. In my experience, as an entrepreneur who has failed a fair number of times, all my challenges have eventually led to a spark of innovation.

Related: All Entrepreneurs Face Failure But the Successful Ones Didn't Quit

This is not just a business lesson. It's personal. As we grow our businesses, and grow as human beings, we have to progress and consider our past failures, moments where we slipped up, so we don't repeat them. There's an often passed around quote attributed to Jack Welch: "An organization's ability to learn and translate that learning into action rapidly, is the ultimate competitive advantage."

We sometimes call that accountability. These are the greatest moments of challenge: owning up to your mistakes. Not just showing humility, but believing in it. Every mistake you make will shape a new vision and propel you in a different direction, one where the possibility of repeating your error won't come up again.

Yet, while reflection is one of the most useful tools an entrepreneur can have, regret is an absolute waste. I can't regret the handful of companies I've launched that have fallen dead flat, because each taught me something.

Related: Study These 9 Traps Even Successful Entrepreneurs Have Fallen For So You Won't

How failure can become a business lesson

Back in 2011, I launched BrandCaddy, a digital storage system for brand assets. I'd gotten tired of chasing after clients' logos, images and videos -- which were sometimes the wrong size or file types -- and conceived of a catch-all app that could house it all. It would streamline the process, save my clients time and save me constant headaches.

Nobody was interested. Most companies simply used Dropbox, which, while an imperfect and itself sometimes disorganized solution, is familiar for most brands. Even if they're well organized, I realized, few clients saw brand identity the way I did, with less regard for fonts or file formats. I wanted to force a program onto the world that would make my life easier, but all I'd done was create a dream app for creatives.

And while I was obviously dismayed by this failure, I didn't let it hold me back. For one, I'd learned some things about my clients' values, which helped me service them better. And it taught me that to create a business model, you need to start with an idea people actually want.

Related: This Entrepreneur Explains How He Survived 150 Rejections From Investors

Failing for all the right reasons

So, that's what I did with, a venture I launched just a couple of years ago. It was designed to be a modern finance newsroom, ideally run as an easy, consumer-focused content marketing arm of a major financial institution. The problem was funding. The way I envisioned it, I needed significant support staff.

When I pitched the company to a group of investors, they loved the idea -- they just didn't get why I needed them. My work on the website, branding and early staffing had been so tight, and my market research so spot on (even a competitor launched a similar channel with way more funding already in their pocket), that these investors didn't see why I needed them at all. Instead of pitching the idea, I pitched a nearly finished product.

MarketStream didn't take off the way I wanted it to (although the idea isn't gone completely; some parties are still interested), but it did confirm the power of my brand proposition. It was the most encouraging type of failure: that I could create a brand from scratch that looked so good that investors didn't see where they fit in.

Related: 10 Strategies for Entrepreneurs Dealing With Failure

How my first great rejection became my first great success

But, none of those compared to my first great failure on the road to entrepreneurship -- one which I imagine most of us have faced at some point. This was the failure that transformed me into an entrepreneur in the first place.

I faced this challenge straight out of college, when I was trying to get a job. I was already considered young for the broadcast news industry, and got turned down by more news stations than I care to admit. At one point, my greatest achievement was having landed a temporary, at times abusive internship at a production company.

It was only after I launched my own company -- which grew into the company I've been running for more than 15 years -- that I realized this important lesson: Logic is relative. What one mid-level producer thinks of my talent is by no means a reflection of what I could really achieve. And those failures, all those unanswered cover letters and closed doors, only solidified my passion for this career and showed me the true path I needed to take.

Within its first year, Cimaglia Productions had grown considerably, landing large clients and then a personal contract with NBC. By 21, some of the local news stations that turned me down only a year earlier were taking my direction from the network level.

Related: 4 Ways I Fail Forward on a Daily Basis and Why You Should Do the Same

Deciding where your story ends

Seeing failure as a dead end is the most significant mistake you can make as an entrepreneur, or indeed in your life. It's fine to ditch an idea that isn't working, as long as you learn from it and integrate that knowledge into your next plan. The method is humility, and the enemy is pride.

And after a while, when you've made enough mistakes, you'll stop making them as often. You'll start being able to forecast your failures. That's what I call being mindful in business -- being able to recognize the value of what you have, and not feeling the need to repeat the mistakes of your past. Much like growing wise in years, it's a state of enlightenment (as much as we can hope for, anyway) that comes only after living, failing and continuing to live. I'm not done failing yet, but I'm at a point where I can live beyond regret and work toward becoming a better person.

My journey of mindfulness, which I only realized after making innumerable mistakes, helped me realize that I needed to focus more on my main company -- and myself as a person. By getting distracted by side projects, I'd neglected what helped me reach that point in the first place.

Like most entrepreneurs, I've spent much of my career focused strictly on the future. It's always about rapid growth, next quarter's numbers, meeting targets, new projects. But, it's equally important to recognize what's already in front of you. And once you learn that, you won't need failure to teach you the value of what you have.

Related Video: Former Apple CEO John Sculley Has a Message to Entrepreneurs: 'Don't Be Afraid to Fail'

Matt Cimaglia

Co-Founder of

An award-winning creative director and entrepreneur, Matt Cimaglia is passionate about cutting-edge technology, fine art, nonprofit work and cycling. His motto: Don't follow trends; lead with ideas.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Business Solutions

Increase Productivity with This Microsoft 365 Subscription, Now $25 Off

It can make the entrepreneur life a lot easier.

Business News

Apple Pay Later Is Ending. Here's What's Taking Its Place.

The program was available for less than a year.


This Artist Answered a Businessman's 'Powerful' Question — Then His Work Became 'the Poster Child for Juneteenth': 'Your Network Really Becomes Your Net Worth'

Reginald Adams was the executive director of a Houston-based art museum for more than a decade before he decided to launch his own public art and design firm.


Harvard Business School Professor Says 65% of Startups Fail for One Reason. Here's How to Avoid It.

Team alignment isn't nice to have -- it's critical for running a successful business.

Business News

Here's What Companies Are Open and Closed on Juneteenth 2024

Since it became a holiday in 2021, Juneteenth has been recognized by some major corporations as a paid day off.

Growing a Business

I Hit $100 Million in Annual Revenue by Being More Transparent — Here Are the 3 Strategies That Helped Me Succeed

Three road-tested ways to be more transparent and build relationships that can transform your business — without leaving you feeling nightmarishly over-exposed.