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We often correlate the word “mistake” to a negative experience or something undesirable. But there’s no doubt that mistakes are a necessary part of personal growth. The same applies to professional careers, particularly when it comes to being an entrepreneur.


Some mistakes may seem devastating at first, but can provide valuable lessons that lead to better lives. We interviewed some local entrepreneurs from various industries to share their experiences and how it helped them grow. Whether it was a huge financial loss or a minor incident, these short stories provide insight into the life of entrepreneurs from many walks of life.



Bruce Pinchbeck


bruce pinchbeck

Bruce Pinchbeck, VP/Creative of The New Tropic

I used to undervalue my work. It felt like I was an imposter who was pretending and that there were so many better artists out there doing incredible work. Why would anyone possibly pay me more for my work? I’d constantly negotiate myself down from jobs because I was afraid the client would walk away. When all the work was complete I usually ended up with an hourly rate no better than a shift position. Something had to give and it eventually did.


The tipping point for me was that I underbid on a job, dramatically. It turned out when I actually ran the numbers on the project that I wasn’t going to make a penny off the project; so I went back and asked the client for a larger budget. They immediately fired me and moved on; wouldn’t even take my calls.


At the time it felt horrible. I took some time and reflected on what went wrong and realized I needed to ask what I was truly worth so that I could deliver the best possible product to my clients and also sustain my own life. Everything changed when I finally made that leap. An odd thing began to happen where people accepted budgets even faster and found me more professional.


One client actually said to me, “My boss was most impressed that you said, ‘no’ to the project with the smaller budget so he wanted to offer you this [larger] one.”


When I look back on it getting fired from that freelance job was the best thing that could have happened to my professional development as an entrepreneur. It taught me that if you undervalue yourself others will too.



Ryan Stewart


ryan stewart

Ryan Stewart, Founder of

The ‘best mistake’ I’ve made is getting started. I’m not an entrepreneurial person – I didn’t grow up selling lemonade or flipping baseball cards, I was actually a bad introvert. I just really hated working for assholes and helping build a company I didn’t believe in – I wanted more from my life.


So, I had an idea and I chased it. I dove head first into trying to build my idea into a “business”. I failed miserably, in every aspect. Knowing what I know now, I never would’ve pursued it. I’m really glad I did though, otherwise I’d be sitting in traffic instead of my home office.




Lia Figueredo


Lia Figueredo, Principal at Milk Media Co.

Jumping at the proverbial carrot: money. Taking on projects or clients for purely financial reasons always results in a disproportionate amount of stress and anxiety. We must remember, passion drove us towards entrepreneurship and only passion will steer us towards our professional and personal fulfillment.


Omitting no from my vocabulary. Always bending over backwards to satisfy a client’s requests despite how inherently ridiculous or unnecessary they may be. Taking on an inhumane amount of work and failing to delegate for fear of surrendering control. Accepting your own limits, establishing boundaries, and embracing the simplicity of “no” are keys to succeeding as an entrepreneur.





Joey Ricard


joey ricard

Joey Ricard, Co-Founder of

I had no money in my account, and just sold my house via text message because I had no liquidity. There was a time I had a Range Rover but had no money for gas. I remember at a point having just enough money in my account to get half way where I needed.


Entrepreneurship is not meant for the weak at heart. It will test you and you will either give up and get a job, or figure out a solution that changes your reality. The best entrepreneurs are good at condensing information, and absorbing it at high densities. They figure out ways to keep from joining what some very successful entrepreneurs will call “Slave Wage”. They use information to build value.


I have developed some amazing technology projects. One of those technologies was acquired by a publicly traded company. On one project I saw my money trading in the market place up to $1.8M dollars, I was a millionaire, and within six months it sank to nothing. I saw my company piss away over $300k cash in about three months. And I had no say in watching it crumble.


I learned this: Always have access to cash. Build a safety net big enough to cover you for six months. More importantly, never listen to anyone that your gut says not to. You can work with them, but make sure you already have your plans created for when you get screwed. Have your escape strategy planned before you even do business with them. Lastly, you will make it if you actually believe in what you are doing. Don’t just tell yourself, you have to believe; otherwise you will crack and burn out.


Its not the first time I have lost, and not going to be the last. Go lose a million dollars.



John D. Saunders


john d saunders

John D Saunders, Digital Marketing Strategist at 5Four Digital

When I worked at an agency as Marketing Director, I learned quickly how to work with others to delegate the work load and consistently strategize with my team. Once I went off on my own, a lot of the responsibility fell on my shoulders. I was doing a lot of the day-to-day work while running the strategy side simultaneously. It wasn’t until I was maxed out working 20 hour days every day, missing valuable time with my loved ones and suffering from constant pressure on myself to outperform, that I decided I needed help.


It was then, I took time to leverage skilled freelance marketers and developers to delegate responsibilities. Using the formula I used at the agency, I dissected each job and delegated accordingly, providing benchmarks for high-level KPIs to the team. I freed up enough time to focus on the strategy side and building content that I could share with business owners. The mantra, of course, is to fail fast and keep it pushing.






Dan DiMassa


dan dimassa

Daniel DiMassa, Founder of Die Epic

When you are a cash strapped start up, there are no words to describe the pain when you see something went to print, a thousand times, wrong. My heart sunk and to make it worse it was all my fault. For those unfamiliar with our adrenaline junkie brand, Die Epic, we put a concussion checklist in every purchase so extreme sport athletes can keep it in their gym bag. The checklist part of the card was correct, the back had a thank you message and a Goal Tag (which is an empty box on our products to write-in a short goal).


The Goal Tag was supposed to say: Happy Customers. After seeing the mock up with fake handwriting font in it, I decided that wasn’t good enough. Seemed fake and insincere. I decided to use my own handwriting and jot it in before making the 1,000 copies. But due to constraints of the print shop closing soon and an unusable design file, it didn’t happen.
A week later, I opened a box of 1,000 misprinted cards, realized my goof up, and probably let out some words not fit for print. As any first month startup will tell you, there was not budget to reprint and isn’t fair to the environment.


But then months passed and something beautiful happened. We started seeing pics on social media of customers hanging the cards in their office with their own handwritten goal facing out – for them and the world to see everyday. A startup is one big adventure of rolling with the punches, sometimes you get a unexpected win.



Chris Gonzalez


chris gonzalez

Chris Gonzalez, CEO of Skyline Technology Group

When I first started as an entrepreneur, I had a lot of time on my hands. I had no other jobs and my only “work” for the day was what I decided it was going to be. Looking back on those days, I wish I had been as organized and diligent as I am now; waking up every morning at 6:30 AM to get a jump start on the stock market and news; catching up on emails and the other necessities before most people’s alarm clocks go off; planning my day and week to make the most out of every minute; going to the gym every afternoon to break up my long days; spending that last bit of my day reflecting on how it went and how it could have gone better.


Getting into a routine and sticking to it was probably the best thing I could recommend to anyone (entrepreneur or otherwise). If you find yourself with a lot of “down time” you need to make the most of it. If you feel like you are busy all day but have nothing to show for it, then you need to make a change. Architecting a daily routine that not only makes you more efficient but one that you love is critical to success. Firefighting every day leads to a quicker burnout and almost always results in non-strategic “work” taking the stage when you should be focusing on the projects that will have the most return for your time.



JennyLee Molina



JennyLee Molina, Principal at JLPR

It has been over 10 years since I took the leap of faith and started JLPR. I’ve had a lot of great successes that I’m eternally grateful for, but I’ve also made my share of bad calls. Everyone says, “learn from your mistakes,” but you can’t begin to learn from your (sometimes tragic) mistakes if you don’t take the first step in acknowledging them.


In public relations, you get rejected often and you don’t have complete control over it. We are at the mercy of editors who have the final say on the content they put out for their audiences. In Miami, there isn’t a shortage of news, we are all in the same pit competing for coveted coverage. Some clients get this, some don’t — but now I make sure I work with clients who understand the news cycle and manage expectations accordingly. We can’t win them all, but you better believe we absolutely try.


I used to think my pitches had to be perfect, I’d spend hours on crafting the perfect pitch note to the point where my hesitation would turn into nervous procrastination. I had to become fearless. I’m not afraid of getting “no’s” anymore but beyond that, I’m not afraid to make the ask. I used to cry over Deco Drive declining coverage. I experienced serious anxiety when I’d email the Miami Herald and never get a response.


Then, I got smart. I grew up. I learned that if you get refused at the door, you might still be able to go through a window with another story angle. I developed great relationships with media and continue to work hard to a be a resource to them. Being polite and persistent goes a long way. Patience over perfection. Today, I enjoy the ride and the meaningful friendships I’ve developed with great colleagues.


On another note, if you’re not buying what a potential client is selling, chances are neither would an editor. I learned that it was more important to enthusiastically believe in what your client has to offer than anything else. Sometimes it just wasn’t the right fit. I took on clients I had a “gut feeling” about that it just wasn’t going to work out. Some thought I could wave a magic wand and get them on the front page of the Miami New Times and there were others I didn’t vibe with but went along with it anyway. I’ve learned to only work with those I feel aligned with and can truly value (and compensate) my work. In life, it should either be a resounding “yes” or a straightforward “no.” If you’re not enthusiastic about a project, take it as a sign and move on. No dollar amount should convince you otherwise. Being authentic in everything you do is “major key.”


Next time you make a mistake, instead of trying to justify it, make it a point to address it head on and be honest with yourself. Sometimes our greatest mistake is fear of rejection, sometimes it’s taking on projects you know aren’t meant for you. It’s up to us to turn our rookie mistakes into valuable learning lessons. You got this!