Today we’d like to introduce you to Matthew Cleary.
Hi Matthew, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
I attended the University of Alabama after high school but left without a degree. I really didn’t know what I wanted to do in life, career-wise. The thought of spending money, under the pressure to figure it out, just didn’t sit well with me. Fraternities and partying just wasn’t something that motivated me. Instead, I went to work back in the Chicago suburbs while also taking some classes at the local community college. Working has always motivated me since I started delivering newspapers in middle school. I’ve never really been on the traditional path in life and I wouldn’t change it for the world! My story only gets better.
Life then led me to Fort Lauderdale in 1995, at the age of 22. I spent the first few months in Florida teaching myself Microsoft Office, while I searched for a job, and this proved to be a valuable skill to have in my search. I landed a job managing transportation logistics with a Honduran melon importer and goods exporter in Port Everglades, bought my first home at the age of 23 and was doing quite well. But again, I found no motivation for myself. I couldn’t see myself in that industry and wanted something more. This in turn led me to a random conversation with a recruiter; introduced to me by my best friend since high school Adam Parks, currently CEO/President of Trinity Wealth Management in Tampa. She convinced me working in construction as a Project Accountant would encompass much of what I was interested in, while also providing the foundational security I needed to build from.
I started working with an ENR top 400 commercial construction contractor around ’98, who was later acquired by Balfour Beatty. After my first 2 years with the company, I decided to relocate to the Washington, DC area where I continued my work with two more ENR top 400 contractors. Once again, the motivation issue kicked in – I wanted to challenge myself more – so I crossed over to the consulting side of the industry. For the next two years, I was a Senior Litigation Consultant for a boutique consulting firm specializing in construction claims. I worked on some high-profile cases like “The Big Dig” in Boston and a $100M claim associated with the Ritz Carlton hotel in New Orleans. The traveling 40 weeks a year wore on me, especially after 9/11. Then I was recruited by a big consulting firm, quit my job and took a phone call an hour after. I was presented what would be my next opportunity which would be the springboard that led me to where I’m at today. I rescinded my acceptance offer, took a 50% pay cut, and relocated to Raleigh, NC.
My Raleigh, NC experience began in 2002 as I was about to turn 30 years old. I was recruited, by my past managers at my first construction job, to handle project accounting and manage financial risk on a massive, eight-building, dormitory project at NC State University – the largest project of its kind in the US at the time. A monumental shift was also taking place in the industry regarding the delivery method, it was referred to as Construction Manager at Risk (CM@Risk). Two years into the project, a political shift of leaders was happening in the company, and I found myself without cover from those that recruited me. They were forced out and landed at Swedish construction giant Skanska. Shortly after, they brought me over to Skanska and created a position for me focused on risk management. I would spend the next 13 years with Skanska.
It was shortly after the country’s financial collapse in 2007 and 2008 when Russ Johnson, VP of Risk Management at Skanska, my friend and mentor, offered me the opportunity to lead two teams in their risk management efforts nationally. Working on projects across the country that shape our communities today, I expanded my knowledge base and found my true calling.
In 2017 I left my post at Skanska and started my company, ConfidentBuild, focused on Risk Management as a Service (RMaaS) for SMB construction managers and general contractors. I began developing proprietary software called RiskFeed™ which powers both ConfidentBuild and FLOWER.
A product by ConfidentBuild, FLOWER is specifically designed for residential property owners, property managers and contractors; bridging a massive gap between the property owner and contractor relationship. The monumental shift that happened in the commercial industry 20 years prior is now making its way to the residential construction, renovation, and repair industry. I’m spearheading this shift with FLOWER and chose Tampa to launch this groundbreaking effort. This is my story and it’s not over yet.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall, and if not, what were the challenges you’ve had to overcome?
There are reasons why most start-up companies fail and if they were easy – everybody would be starting a company. I’ve had my fair share of challenges both in my personal and professional life while building this company. These challenges have created obstacles and setbacks for which I’ve had to dig deep, problem solve and overcome.
The greatest challenge for me was starting a software company without any relative experience other than messing around with computers professionally, and surfing the internet like many people. It’s scary to venture into something, which costs a lot of money, without having the knowledge. The learning curve can be expensive and mistakes definitely cost me. Quitting was never an option when I chose to go down this path. There was a reason I started this venture and it wasn’t about money, it was about making a difference. It was about making a real change that would produce positive results for the stakeholders. It also provided me with a creative outlet which is such an important part of my life.
Many sleepless nights and mentally challenging days are the norm. The first go at it was very costly and did not produce what I was looking for in the end, but I was determined to keep going. Once we were back on track, we ran into the pandemic. Like many businesses, the pandemic created a lot of challenges. As a pre-revenue startup we were not eligible for the government handouts and it was frustrating watching other businesses’ money grab. Many did not need it or they used the funds for other things not for its intended purpose. Delays were costly and time can be costly in the tech world. This was just another challenge we had to overcome.
Even through the challenges, we remain steadfast and 2022 is going to be a breakout year for us.
Thanks – so what else should our readers know about FLOWER?
At FLOWER, we feel homeowners deserve a more sensibler platform to procure contractors for their home construction, renovation, and significant repair needs. Managing risk and quality control are both benchmarks of a successful commercial construction project. We aim to provide a platform that manages risk and holds contractors accountable for their work. In addition, we aim to provide a platform that’s exclusive for great contractors whether they are seasoned, recently entered, or plan on building a business in the industry. We bring the two together – contractors and homeowners – by creating a pathway to success via FLOWER.
While lead generation will be a part of our process, our main focus is on ensuring projects are successful with minimal to no risk to the homeowner. Homeowners need to ask themselves, do they want a construction risk manager helping them achieve success or do they want a lead generation company like Angi/HomeAdvisor, what in my opinion, is a business model selling their information to minimally vetted contractors? As the saying goes, if you are getting something for free – then you are the product!
We accomplish success by avoiding and mitigating risks, by creating tools and providing resources to make sure projects are successful. We do this by weeding out the bad actors, the frauds, the scams, the unethical and by using our experience.
We bring over two decades of knowledge and successful risk management experience, at the highest level, to FLOWER and lead a monumental shift which will create opportunities for our youth, our veterans and anyone looking to build a career in the construction industry. It is an industry desperate for skilled workers and well managed companies. We support and want to create awareness that Trade Schools are a sexy option in lieu of traditional educational paths, in a world of high education costs.
Join our Street Team and help us get the word out. Visit our site to learn more. Interested in a career with FLOWER or ConfidentBuild? We are focused on creating a modern work environment for our employees that inspires both professionally and personally.
As we like to say, Start With FLOWER.
How do you define success?
To make a difference, one must be passionate about what they are doing – regardless of its nature whether personal or professional. Defining success has always been a driving force for me in everything I put my efforts into. If I cannot define success, then I pivot until I do.
To achieve success, one must be inspired. Inspiration can come from many different places. My friends inspire me with their successes. If they can succeed, so can I.
Authors like Marcus Buckingham inspired me during my career while working at Skanska.
My military hero buddies retired Army Major Edward Pulido who is an amputee and co-Founder of the John Daly Major Ed Heart of a Lion Foundation, Wesley Bauguess who overcame the loss of her husband in the war, and retired Navy SEALs: Rob O’Neil who took out the biggest terrorist of our time, Ray “Cash” Care, and Darren “McB” McBurnett founder of Uncommon Grit Foundation inspire me every day. I spend a lot of my non-professional time raising money and creating awareness for helping our military Veterans and their families.
Mike Shinoda from the band Linkin Park inspired me how he overcame the death of his best friend and lead singer Chester Bennington, by writing music and performing it. Watching people do great things inspires me.
Defining success involves passion to reach a goal by breaking down the path into smaller goals. How I define success can be summed up in my motto: “Make a difference and be inspired”.
Contact Info:
- Email: contact@confidentbuild.com
- Website: https://startwithflower.com or https://confidentbuild.com
- Instagram: https://www.instagram.com/matthewdcleary/
- Facebook: https://www.facebook.com/MCleary73/
- Other: https://www.linkedin.com/in/matthewdcleary/

